Polyurethane diacrylate compositions as carrier for pharmacological agents

• US 4,439,585 A
• Filed: 09/02/1982
• Issued: 03/27/1984
• Est. Priority Date: 11/12/1980
• Status: Expired due to Fees

• Current Assignee: Tyndale Plains-Hunter, Ltd.
• Original Assignee: Tyndale Plains-Hunter, Ltd.
• Inventors: Johnston, Christian W., Gould, Francis E.
• Primary Examiner(s): Cockeram, H. S.
• Application Number:
  US06/414,273
• Time in Patent Office: 572 Days
• Field of Search: 525/127, 525/454, 525/455, 528/75, 528/904, 521/905
• US Class Current: 525/127
• CPC Class Codes: A61K 9/2031 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
• CPC Class Codes: A61L 15/24 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: A61L 17/04 Non-resorbable materials
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 283/00 Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
• CPC Class Codes: C08F 299/065 from polyurethanes with side or terminal unsaturations
• CPC Class Codes: C08G 18/6674 with compounds of group C08G18/3203
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: H01M 50/414 Synthetic resins, e.g. thermoplastics or thermosetting resins
• CPC Class Codes: H01M 50/489 Separators, membranes, diaphragms or spacing elements inside the cells, characterised by their physical properties, e.g. swelling degree, hydrophilicity or shut down properties
• CPC Class Codes: Y02E 60/10 Energy storage using batteries
• CPC Class Codes: Y10S 521/905 Hydrophilic or hydrophobic cellular product
• CPC Class Codes: Y10S 528/904 Isocyanate polymer having stated hydrophilic or hydrophobic property

Abstract

Polyurethane diacrylate compositions are obtained by reacting a diacrylate in the presence of from about 65 to about 95 weight percent of a hydrophilic polyurethane resin. The compositions will form a hydrogel upon immersion in water and are permeable to gases, ions and other low molecular weight species. The hydrophilic polyurethane diacrylate compositions may be molded to form shaped products that are dimensionally stable after repeated exposure to boiling water and exhibit memory. The compositions are useful as carriers for pharmacologically active agents in forming an oral delivery system.

Claims

1. An oral delivery system comprising a pharmacologically active agent and as a carrier vehicle therefor a hydrophylic polyurethane diacrylate composition which will form a hydrogel upon immersion in water and is permeable to gases, ions and other low molecular weight species, which composition is dimensionally stable and exhibits memory, said polyurethane diacrylate composition comprising from about 90 to about 65 weight percent of a hydrophilic polyurethane resin characterized by terminal hydroxyl groups and from about 10 to about 35 weight percent of a diacrylate.

2. The oral delivery system of claim 1 wherein said diacrylate is a dimethacrylate.

3. The oral delivery system of claim 1 wherein said diacrylate is diethylene glycol diacrylate.

4. The oral delivery system of claim 1 wherein said diacrylate is about 20 weight percent of said composition.

5. The oral delivery system of claim 2 wherein said diacrylate is a polyethylene glycol dimethacrylate having an average molecular weight of about 1586.

6. The oral delivery system of claim 1 wherein said diacrylate is a polyethylene glycol diacrylate having an average molecular weight of about 508.

7. The oral delivery system of claim 1 wherein said hydrophylic polyurethane resin is derived from a mixture of polyols and a diisocyanate.

8. The oral delivery system of claim 7 wherein one of the polyols in said mixture is diethylene glycol.

9. The oral delivery system of claim 7 wherein one of the polyols in said mixture is a polyethylene glycol having an average molecular weight between about 400 and 1450.

10. An oral delivery system comprising a pharmacologically active agent and as a carrier vehicle therefor a hydrophylic polyurethane diacrylate composition which will form a hydrogel upon immersion in water;

is permeable to gases, ions and other low molecular weight species;

is dimensionally stable and exhibits memory;

obtained by the reaction of from about 10 to about 35 weight percent of a diacrylate having the formula;

##STR3## wherein R is selected from the group consisting of hydrogen and the methyl radical and n is a whole number, such that the average molecular weight of the diacrylate is no greater than 1586;

in the presence of from about 90 to about 65 weight percent of a hydrophylic polyurethane resin.

11. The oral delivery system of claim 10 wherein said diacrylate is a dimethacrylate.

12. The oral delivery system of claim 10 wherein said diacrylate is about 20 weight percent of said composition.

13. The oral delivery system of claim 10 wherein said diacrylate is diethylene glycol diacrylate.

14. The oral delivery system of claim 11 wherein said diacrylate is a polyethylene glycol dimethacrylate having an average molecular weight of about 1586.

15. The oral delivery system of claim 10 wherein said diacrylate is a polyethylene glycol diacrylate having an average molecular weight of about 508.

16. The oral delivery system of claim 10 wherein said hydrophylic polyurethane resin is derived from a mixture of polyols and a diisocyanate.

17. The oral delivery system of claim 16 wherein one of the polyols in said mixture is diethylene glycol.

18. The oral delivery system of claim 16 wherein one of the polyols in said mixture is a polyethylene glycol having an average molecular weight between about 400 and about 1450.