Biocidal particles of methylated polystyrene

• US 8,598,246 B2
• Filed: 10/25/2011
• Issued: 12/03/2013
• Est. Priority Date: 10/31/2002
• Status: Expired due to Fees

• Current Assignee: Auburn University
• Original Assignee: Auburn University
• Inventors: Worley, Shelby D., Chen, Yongjun
• Primary Examiner(s): ROGERS, JAMES WILLIAM
• Application Number:
  US13/280,529
• Publication Number:
  US 20120035284A1
• Time in Patent Office: 770 Days
• Field of Search: None
• US Class Current: 521/147
• CPC Class Codes: A01N 59/00 Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• CPC Class Codes: C08F 112/08 Styrene
• CPC Class Codes: C08F 8/24 Haloalkylation
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups

Abstract

Methylated polystyrene having pendant N-halamine and N-halamine precursor groups. Biocidal particles have been prepared by reacting highly crosslinked methylated polystyrene beads as starting materials with various N-halamine precursor compounds. The resulting polymer beads are halogenated with chlorine or bromine. The porous beads will be useful in disinfection applications as well as for sanitization and controlling noxious odor when mixed with absorbent materials in items such as disposable diapers, infant swimwear, incontinence pads, bandages, sanitary napkins, pantiliners, mattress covers, shoe inserts, sponges, animal litter, carpets, and fabrics.

Claims

1. A porous polymer bead comprising a methylated polystyrene having pendant N-halamine precursor groups, wherein the N-halamine precursor groups comprise imidazolidinone groups, isocyanurate groups, oxazolidinone groups, or 3-hydroxyalkylhydantoin groups, wherein each N-halamine precursor group is pendant from a methyl group at the para position of a phenyl group of the methylated polystyrene, and the methylated polystyrene is about 3 to about 10 percent crosslinked.

2. The methylated polystyrene of claim 1, wherein the polystyrene is crosslinked with divinylbenzene.

3. The methylated polystyrene of claim 1, wherein the polystyrene is from about 5 to about 8 percent crosslinked.

4. A porous polymer bead comprising a biocidal methylated polystyrene having pendant N-halamine groups, wherein the N-halamine groups comprise imidazolidinone groups, isocyanurate groups, oxazolidinone groups, or 3-hydroxyalkylhydantoin groups, wherein each N-halamine group is pendant from a methyl group at the para position of a phenyl group of the methylated polystyrene, and the methylated polystyrene is about 3 to about 10 percent crosslinked.

5. The biocidal methylated polystyrene of claim 4, wherein the polystyrene is crosslinked with divinylbenzene.

6. The biocidal methylated polystyrene of claim 4, wherein the polystyrene is from about 5 to about 8 percent crosslinked.

7. A porous polymer bead comprising a polymer having a repeating unit, said unit having the formula:

8. The polymer of claim 7, wherein R has the formula:

9. The polymer of claim 8, wherein R₁ and R₂ are methyl.

10. The polymer of claim 7, wherein R has the formula:

11. The polymer of claim 10, wherein R₁ and R₂ are methyl.

12. The polymer of claim 7, wherein R has the formula:

13. The polymer of claim 12, wherein R₁, R₂, R₃, and R₄ are methyl.

14. The polymer of claim 7, wherein R has the formula:

15. The polymer of claim 14, wherein R₁, R₂, R₃, and R₄ are methyl.

16. The polymer of claim 7, wherein R has the formula:

17. The polymer of claim 16, wherein R₁ is methyl or ethyl.

18. The polymer of claim 7, wherein R has the formula:

19. The polymer of claim 18, wherein R₁ is methyl or ethyl.

20. The polymer of claim 7, wherein R has the formula:

21. The polymer of claim 7, wherein R has the formula:

22. A porous polymer bead comprising a methylated polystyrene having a N-halamine precursor group bonded to at least some of the benzene rings of the polystyrene by a methylene group, wherein the N-halamine precursor group is an imidazolidinone group, an isocyanurate group, an oxazolidinone group, or a 3-hydroxyalkylhydantoin group, wherein each N-halamine precursor group is pendant from a methyl group at the para position of a phenyl group of the methylated polystyrene, and the methylated polystyrene is about 3 to about 10 percent crosslinked.

23. A porous polymer bead comprising a methylated polystyrene having a biocidal N-halamine group bonded to at least some of the benzene rings of the polystyrene by a methylene group, wherein the N-halamine group is an imidazolidinone group, an isocyanurate group, an oxazolidinone group, or a 3-hydroxyalkylhydantoin group, wherein each N-halamine group is pendant from a methyl group at the para position of a phenyl group of the methylated polystyrene, and the methylated polystyrene is about 3 to about 10 percent crosslinked.