Polymeric fibers and methods of making

• US 7,939,578 B2
• Filed: 08/30/2007
• Issued: 05/10/2011
• Est. Priority Date: 02/23/2007
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Buchholz, Jessica M., Ali, Mahfuza B., Olson, Linda K. M., Svarovsky, Michael J., Walter, Richard L., Haddad, Louis C., Stepanova, Narina Y., Scholz, Matthew T., Wolk, Diane R., Zhang, Yifan, Wright, Robin E., Ylitalo, Caroline M.
• Primary Examiner(s): McClendon; Sanza L
• Application Number:
  US11/847,397
• Publication Number:
  US 20080207794A1
• Time in Patent Office: 1,349 Days
• Field of Search: 522/71, 522/74, 522/84, 522/104, 522/150, 522/153, 522/178, 522/181, 522/182, 524/800, 524/804, 524/832, 524/845, 428/357, 428/364, 428/392, 428/394, 428/395, 427/496, 427/457, 427/508, 252/182.11, 252/182.12, 252/182.13, 252/182.18, 252/182.23, 252/182.27, 523/300
• US Class Current: 522/181
• CPC Class Codes: D01D 5/00 Formation of filaments, threads, or the like
• CPC Class Codes: D01D 5/38 Formation of filaments, threads, or the like during polymerisation
• CPC Class Codes: D01F 1/103 Agents inhibiting growth of microorganisms
• CPC Class Codes: D01F 6/16 from polymers of unsaturated carboxylic acids or unsaturated organic esters, e.g. polyacrylic esters, polyvinyl acetate
• CPC Class Codes: D01F 6/28 from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: Y10T 428/29 Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
• CPC Class Codes: Y10T 428/2913 Rod, strand, filament or fiber
• CPC Class Codes: Y10T 428/2964 Artificial fiber or filament
• CPC Class Codes: Y10T 428/2967 Synthetic resin or polymer
• CPC Class Codes: Y10T 428/2969 Polyamide, polyimide or polyester

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

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.

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.

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.

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.

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.

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.

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.