IP Library Granted Patent US 11,911,524
Granted Patent B2
US 11,911,524 · App. 17/469,385 · Granted Feb 27, 2024

Biomedical foams

Inventors: Catharina Everdina Hissink (Groningen, NL); Theodorus Adrianus Cornelius Flipsen (Groningen, NL); Johan Zuidema (Groningen, NL); Linda Joan Gibcus (Groningen, NL)
Assignee: Stryker European Operations Holdings LLC
A61L15/26A61L15/425A61L15/64A61L24/0036A61L24/046A61L26/0085C08G18/10C08G18/14C08G18/3206C08G18/4018C08G18/4277C08G18/73C08L75/04C08G2110/0083C08G2230/00
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Quick Facts
Patent No.
US 11,911,524
App. No.
17/469,385
Granted
Feb 27, 2024
Kind
B2
Abstract

The invention relates, generally, to porous absorbent materials which are suitable for packing antrums or other cavities of the human or animal body. More particularly, it relates to hydrophilic biodegradable foams, which may be used e.g. in the form of a plug or tampon, for instance for controlling bleeding, wound closure, prevent tissue adhesion and/or support tissue regeneration. The invention provides an absorbent foam, suitable for packing antrums or other cavities of the human or animal body, comprising a biodegradable synthetic polymer, which polymer preferably comprises —C(O)—O—groups in the backbone of the polymer, for instance polyurethane and/or polyester units combined with polyethers.

Claims (33)

1. A foam comprising a phase-separated polymer including an amorphous segment and a crystalline segment, said polymer having the formula:

—[R-Q 1 [-R′—Z 1 —[R″—Z 2 —R′—Z 3 ] p —R″Z 4 ] q —R′-Q 2 ]- n   (I),

wherein:

the amorphous segment comprises R, and at least one R comprises (i) a hydrophilic segment, the hydrophilic segment being derived from polyethylene glycol, polypropylene glycol, or polybutylene glycol, and (ii) a polyester segment based on lactide and ε-caprolactone,

R′ and R″ are independently C 2 -C 8 alkylene, optionally comprising S, N, P or O in the C 2 -C 8 alkylene, wherein the C 2 -C 8 alkylene is optionally substituted with C 1 -C 10 alkyl or C 1 -C 10 alkyl groups substituted with protected S, N, P or O moieties,

Z 1 -Z 4 are each urethane,

Q 1 and Q 2 are independently urea, urethane, amide, carbonate, ester or anhydride,

n is an integer from 5-500, and

p and q are independently 0 or 1, provided that when q is 0, R is a mixture of at least one crystalline polyester, polyetherester or polyanhydride segment and at least one amorphous aliphatic polyester, polyether, polyanhydride and/or polycarbonate segment.

2. The foam according to claim 1 , wherein R′ and R″ are independently C 2 -C 8 alkylene.

3. The foam according to claim 1 , wherein R′ is (CH 2 ) 4 , R″ is (CH 2 ) 4 , or both R′ and R″ are (CH 2 ) 4 .

4. The foam according to claim 1 , wherein Q 1 and Q 2 are each urethane.

5. The foam according to claim 1 , wherein the at least one R comprises lactide and ε-caprolactone in a content of 20-50 wt. %.

6. The foam according to claim 1 , wherein the at least one R comprises lactide and ε-caprolactone in a 1:1 molar ratio.

7. The foam according to claim 1 , wherein the at least one R comprises polyethyleneglycol in a content of 20-50 wt. %.

8. The foam according to claim 1 , wherein the at least one R comprises: polyethylene glycol in a content of 10-60 wt. %; and lactide and ε-caprolactone in a content of 5-60 wt. %.

9. The foam according to claim 1 , wherein the at least one R has a molecular weight between 1,000 and 4,000 and comprises about 25 wt. % lactide, about 25 wt. % ε-caprolactone, and about 50 wt. % of polyethyleneglycol.

10. The foam according to claim 1 , wherein the at least one R comprises a first polyester segment based on lactide and ε-caprolactone, a central hydrophilic segment based on polyethylene glycol, and a second polyester segment based on lactide and ε-caprolactone.

11. The foam according to claim 10 , wherein the at least one R comprises: polyethylene glycol in a content of 10-60 wt. %; and lactide and ε-caprolactone in a content of 5-60 wt. %.

12. The foam according to claim 1 having a fluid absorption capacity of 1500-2500% based on a dry weight of the foam.

13. The foam according to claim 1 having a fluid absorption capacity of 0.5-0.99 g/cm 3 .

14. The foam according to claim 1 having a density of 0.01-0.2 g/cm 3 and/or a porosity ranging from 85 to 99%.

15. The foam according to claim 1 further comprising a drug.

16. The foam according to claim 1 further comprising a haemostatic component.

17. The foam according to claim 1 having an initial elastic modulus of from 30-120 Mpa, a tensile strength of 10-45 Mpa, and an initial elongation at break from 500-1200%.

18. The foam according to claim 1 having a complete fragmentation time ranging from 1 to 10 days.

19. A foam comprising a phase-separated polymer including:

(i) an amorphous segment comprising:

(a) a hydrophilic segment comprising a polyalkylene glycol comprising the reaction product of ethylene glycol, propylene glycol, butylene glycol, and combinations thereof, and

(b) a polyester segment comprising the reaction product of lactide and ε-caprolactone; and

(ii) a crystalline segment comprising urethane groups.

20. The foam according to claim 19 , wherein the amorphous segment further comprises a second polyester segment based on lactide and ε-caprolactone.

21. The foam according to claim 20 , wherein the amorphous segment comprises: polyethylene glycol in a content of 10-60 wt. %; and lactide and ε-caprolactone in a content of 5-60 wt. %.

Assignments (5)
NUNC PRO TUNC ASSIGNMENT Recorded Feb 2, 2023
From: STRYKER EUROPEAN HOLDINGS I, LLC
To: STRYKER EUROPEAN HOLDINGS III, LLC
Reel/Frame 062634/0564 →
CHANGE OF NAME Recorded Feb 2, 2023
From: STRYKER EUROPEAN HOLDINGS III, LLC
To: STRYKER EUROPEAN OPERATIONS HOLDINGS LLC
Reel/Frame 062634/0668 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2021
From: HISSINK, CATHARINA EVERDINA; FLIPSEN, THEODORUS ADRIANUS CORNELIUS; ZUIDEMA, JOHAN; GIBCUS, LINDA JOAN
To: POLYGANICS IP B.V.
Reel/Frame 057440/0690 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2021
From: POLYGANICS B.V.
To: POLYGANICS IP B.V.
Reel/Frame 057441/0351 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2021
From: POLYGANICS IP B.V.
To: STRYKER EUROPEAN HOLDINGS I, LLC
Reel/Frame 057441/0595 →