IP Library › Granted Patent US 7,939,578
Granted Patent B2
US 7,939,578 · App. 11/847,397 · Granted May 10, 2011

Polymeric fibers and methods of making

Assignee: 3M Innovative Properties Company
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Quick Facts
Patent No.
US 7,939,578
App. No.
11/847,397
Granted
May 10, 2011
Kind
B2
Abstract

Polymeric fibers and methods of making the polymeric fibers are described. The polymeric fibers are crosslinked hydrogels or dried hydrogels that are prepared from a precursor composition that contains polymerizable material having an average number of ethylenically unsaturated groups per monomer molecule greater than 1.0. The polymeric fibers can contain an optional active agent.

Claims (45)

1. A method of making a polymeric fiber, the method comprising:

providing a precursor composition comprising:

a) at least 5 weight percent polar solvent based on a total weight of the precursor composition, wherein the polar solvent comprises water and is not reactive in the precursor composition; and

b) polymerizable material capable of free-radical polymerization and having an average number of ethylenically unsaturated groups per monomer molecule greater than 1.0, wherein the polymerizable material is miscible with the polar solvent;

forming a stream of the precursor composition; and

exposing the stream to radiation for a time sufficient to at least partially polymerize the polymerizable material and to form a first swollen polymeric fiber having an aspect ratio greater than 3:1, wherein the first swollen polymeric fiber is a hydrogel swollen with the polar solvent.

2. The method of claim 1 , wherein the polymerizable material comprises a poly(alkylene oxide (meth)acrylate) having an average number of (meth)acryloyl groups per monomer molecule equal to at least 2.

3. The method of claim 2 , wherein the poly(alkylene oxide (meth)acrylate) has a weight average molecular weight no greater than 2000 g/mole.

4. The method of claim 1 , wherein the method further comprises

removing at least a portion of the polar solvent from the first swollen fiber to form a dried fiber.

5. The method of claim 1 , wherein the precursor composition further comprises an active agent.

6. The method of claim 5 , wherein the active agent comprises a bioactive agent.

7. The method of claim 1 , wherein the precursor composition further comprises a photoinitiator and the radiation comprises actinic radiation.

8. The method of claim 1 , wherein the method further comprises

removing at least a portion of the polar solvent from the first swollen fiber to form a dried fiber; and

contacting the dried fiber with a sorbate for a time sufficient for the dried fiber to sorb at least a portion of the sorbate to form a second swollen polymeric fiber, wherein the sorbate comprises at least one active agent.

9. The method of claim 8 , wherein the method further comprises drying the second swollen polymeric fiber.

10. A method of preparing an article comprising a polymeric fiber, the method comprising:

providing a precursor composition comprising

a) 5 weight percent to 85 weight percent polar solvent based on a total weight of the precursor composition, wherein the polar solvent comprises water is not reactive in the precursor composition; and

b) 15 weight percent to 95 weight percent polymerizable material based on the total weight of the precursor composition, the polymerizable material being capable of free-radical polymerization and being miscible in the polar solvent, the polymerizable material comprising a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl functionality groups and having at least 5 alkylene oxide units; and

forming a stream of the precursor composition; and

exposing the stream to radiation for a time sufficient to at least partially polymerize the polymerizable material and to form a first swollen fiber having an aspect ratio greater than 3:1, wherein the first swollen fiber is a hydrogel swollen with the polar solvent.

11. The method of claim 10 , wherein the method further comprises

removing at least a portion of the polar solvent from the first swollen fiber to form a dried fiber.

12. The method of claim 10 , wherein the precursor composition comprises less than 1 weight percent anionic monomer based on the weight of the polymerizable material.

13. The method of claim 10 , wherein the poly(alkylene oxide (meth)acrylate) has a weight average molecular weight less than 2000 g/mole.

14. The method of claim 10 , wherein the precursor composition further comprises an active agent.

15. The method of claim 14 , wherein the active agent comprises a bioactive agent.

16. The method of claim 10 , wherein the precursor composition further comprises a photoinitiator and the radiation comprises actinic radiation.

17. The method of claim 10 , wherein the method further comprises

removing at least a portion of the polar solvent from the first swollen fiber to form a dried fiber; and

contacting the dried fiber with a sorbate for a time sufficient for the dried fiber to sorb at least a portion of the sorbate to form a second swollen polymeric fiber, wherein the sorbate comprises an active agent.

18. The method of claim 17 , wherein the active agent comprises an ethylenically unsaturated group and a photoinitiator, the method further comprises exposing the second swollen polymeric fiber to actinic radiation.

19. The method of claim 17 , wherein the method further comprises drying the second swollen polymeric fiber.

20. An article comprising a polymeric fiber having an aspect ratio greater than 3:1, the polymeric fiber comprising a free-radical polymerization reaction product of a precursor composition comprising

a) 5 weight percent to 85 weight percent polar solvent based on a total weight of the precursor composition, wherein the polar solvent comprises water and is not reactive in the precursor composition; and

b) 15 weight percent to 95 weight percent polymerizable material based on the total weight of the precursor composition, the polymerizable material being capable of free-radical polymerization and being miscible in the polar solvent, the polymerizable material comprising a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl groups and having at least 5 alkylene oxide units,

wherein the polymeric fiber is a hydrogel or a dried hydrogel.

21. An article comprising a polymeric fiber having an aspect ratio greater than 3:1, the polymeric fiber comprising:

a) a free-radical polymerization reaction product of a precursor composition comprising polymerizable material being capable of free-radical polymerization, the polymerizable material comprising a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl groups and having at least 5 alkylene oxide units; and

b) an active agent.

22. The method of claim 1 , wherein the polymerizable material comprises an alkoxylated di(meth)acrylate, alkoxylated tri(meth)acrylate, alkoxylated tetra(meth)acrylate, or alkoxylated penta(meth)acrylate.

23. The method of claim 10 , wherein the polymerizable material comprises an alkoxylated di(meth)acrylate, alkoxylated tri(meth)acrylate, alkoxylated tetra(meth)acrylate, or alkoxylated penta(meth)acrylate.

24. The article of claim 20 , wherein the polymerizable material comprises an alkoxylated di(meth)acrylate, alkoxylated tri(meth)acrylate, alkoxylated tetra(meth)acrylate, or alkoxylated penta(meth)acrylate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2007
From: WRIGHT, ROBIN E.; ALI, MAHFUZA B.; BUCHHOLZ, JESSICA M.; HADDAD, LOUIS C.; OLSON, LINDA K.M.; SCHOLZ, MATTHEW T.; STEPANOVA, NARINA Y.; SVAROVSKY, MICHAEL J.; WALTER, RICHARD L.; YLITALO, CAROLINE M.; WOLK, DIANE R.; ZHANG, YIFAN
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 019772/0937 →
Continuity (3)
Provisional Application 60891260 · Feb 23, 2007
Provisional Application 60946745 · Jun 28, 2007
Related Publication 20080207794A1 · Aug 28, 2008