Radiopaque polyurethanes and catheters formed therefrom

• US 4,722,344 A
• Filed: 05/23/1986
• Issued: 02/02/1988
• Est. Priority Date: 05/23/1986
• Status: Expired due to Term

• Current Assignee: Medex Incorporated (Smiths Group International Holdings Ltd.)
• Original Assignee: Critikon, Inc.
• Inventors: Cambron, Ronald E., Mills, Kevin M., Silverwood, Hartley A., Dempsey, Donald J.
• Primary Examiner(s): Yasko, John D.
• Application Number:
  US06/866,606
• Time in Patent Office: 620 Days
• Field of Search: 604/265, 604/280, 128/658, 524/44, 524/83
• US Class Current: 600/435
• CPC Class Codes: A61L 29/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 29/18 Materials at least partially X-ray or laser opaque
• CPC Class Codes: C08G 18/3802 having halogens
• CPC Class Codes: C08G 18/773 halogens
• CPC Class Codes: C08L 75/04 Polyurethanes

Abstract

Catheters formed from polyurethanes containing sufficient halogenated moieties in the polymer structure to make the polyurethanes radiopaque are disclosed. Such polyurethanes can be prepared by employing halogenated diols and/or halogenated diisocyanate reactants. In preferred cases, the catheters are optically transparent in addition to being radiopaque.

Claims

1. A catheter formed from a polyurethane containing sufficient halogenated moieties in the polymer structure to make the catheter radiopaque.

2. A catheter of claim 1 wherein said polyurethane contains at least 10 weight percent halogen.

3. A catheter of claim 2 wherein said polyurethane contains said halogenated moieties in its backbone.

4. A catheter of claim 3 wherein said halogenated backbone includes a halogenated diol.

5. A catheter of claim 4 wherein said halogenated diol comprises a brominated diol.

6. A catheter of claim 5 wherein said brominated diol comprises a mixed ester of tetrabromophthalic anhydride with diethylene glycol and propylene glycol.

7. A catheter of claim 5 wherein said brominated diol comprises dibromoneopentyl glycol.

8. A catheter of claim 3 wherein said backbone includes a halogenated diisocyanate.

9. A catheter of claim 3 wherein said backbone includes a halogenated diol and a halogenated diisocyanate.

10. A catheter of claim 1 which is optically transparent.

11. A catheter of claim 3 which is optically transparent.

12. A catheter of claim 5 which is optically transparent.

13. A polyurethane containing sufficient halogenated moieties in the polymer structure to make the polyurethane radiopaque.

14. A polyurethane of claim 13 wherein said halogenated moieties are contained in the polymer backbone.

15. A polyurethane of claim 14 containing at least about 10 weight percent halogen in the polymer structure.

16. A polyurethane of claim 15 wherein said halogenated backbone moieties are formed from a halogenated diol.

17. A polyurethane of claim 16 wherein said halogenated diol comprises a brominated diol.

18. A polyurethane of claim 17 wherein said brominated diol comprises a mixed ester of tetrabromophthalic anhydride with diethylene glycol and propylene glycol.

19. A polyurethane of claim 17 wherein said brominated diol comprises dibromoneopentyl glycol.

20. A polyurethane of claim 15 wherein said backbone includes a halogenated diisocyanate.

21. A polyurethane of claim 13 which is optically transparent.

22. A polyurethane of claim 17 which is optically transparent.

23. A radiopaque polyurethane comprising the reaction product of:

(a) a diisocyanate; and

(b) a diol selected from the group of low molecular weight diols, high molecular diols, or a combination of both;

at least one of said diisocyanate and said diol being halogenated and present in a sufficient quantity to make said polyurethane reaction product radiopaque.

24. A polyurethane of claim 23 wherein said diol includes an amount of a brominated diol sufficient to provide said polyurethane with at least about 10 weight percent bromine therein.

25. A shaped article formed from a polyurethane containing sufficient halogenated moieties in the polymer structure to make the shaped article radiopaque.

26. A radiopaque optically-transparent chateter formed from a polyurethane comprising a reaction product of a brominated diol and a diisocyanate, said polyurethane containing at least about 10 weight percent bromine in its backbone.