BIOCIDAL PARTICLES OF METHYLATED POLYSTYRENE

• US 20100029797A1
• Filed: 10/05/2009
• Published: 02/04/2010
• Est. Priority Date: 10/31/2002
• Status: Abandoned Application

• Current Assignee: Auburn University
• Original Assignee: Auburn University
• Inventors: Chen, Yongjun, Worley, Shelby D.
• Application Number:
  US12/573,336
• Publication Number:
  US 20100029797A1
• Time in Patent Office: Days
• 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 method of making a crosslinked and porous methylated polystyrene bead, comprising:

reacting an insoluble functionalized crosslinked and porous methylated polystyrene bead with a N-halamine precursor and an alkali metal base to produce a crosslinked and porous methylated polystyrene bead having pendant N-halamine precursor groups, wherein the reaction is performed heterogeneously in a medium.

2. The method of claim 1, wherein the functionalized methylated polystyrene bead is a crosslinked poly(chloromethyl)styrene.

3. The method of claim 1, wherein the N-halamine precursor is a hydantoin, an imidazolidinone, an oxazolidinone, or an isocyanurate.

4. The method of claim 1, wherein said reacting occurs for from about 12 to about 96 hours at a temperature of from about 70°

to about 120°

C.

5. The method of claim 1, further comprising halogenating the crosslinked and porous methylated polystyrene bead having pendant N-halamine precursor groups to produce a biocidal crosslinked and porous methylated polystyrene bead having pendant N-halamine groups.

6. The method of claim 1, wherein the alkali metal base is an alkali metal carbonate.

7. The method of claim 1, wherein the alkali metal base is an alkali metal hydroxide.

8. The method of claim 1, wherein the alkali metal base is an alkali metal hydride.

9. The method of claim 1, wherein the alkali metal is sodium or potassium.

10. The method of claim 1, wherein said medium is dimethylformamide.

11. The method of claim 1, wherein said medium is dimethylsulfoxide.

12. A method for making a crosslinked and porous methylated polystyrene bead, comprising:

reacting a N-halamine precursor with an alkali metal base to produce an alkali metal salt of the N-halamine precursor; and

reacting the alkali metal salt of the N-halamine precursor with an insoluble functionalized crosslinked and porous methylated polystyrene bead to produce a crosslinked and porous methylated polystyrene bead having pendant N-halamine precursor groups, wherein the reaction with the functionalized crosslinked and porous methylated polystyrene bead is performed heterogeneously in a medium.

13. The method of claim 12, wherein the functionalized methylated polystyrene bead is a crosslinked poly(chloromethyl)styrene.

14. The method of claim 12, wherein the N-halamine precursor is a hydantoin, an imidazolidinone, an oxazolidinone, or an isocyanurate.

15. The method of claim 12, wherein said reacting of the N-halamine precursor with the alkali metal base occurs for from about 15 minutes to about 2 hours at a temperature of from about 25 to about 100°

C.

16. The method of claim 12, wherein said reacting of the alkali metal salt with the functionalized crosslinked and porous methylated polystyrene bead occurs for from about 4 to about 96 hours at a temperature of from about 70°

to about 120°

C.

17. The method of claim 12 further comprising halogenating the crosslinked and porous methylated polystyrene bead having pendant N-halamine precursor groups to produce a biocidal crosslinked and porous methylated polystyrene bead having pendant N-halamine groups.

18. The method of claim 12, wherein the alkali metal base is an alkali metal carbonate.

19. The method of claim 12, wherein the alkali metal base is an alkali metal hydroxide.

20. The method of claim 12, wherein the alkali metal base is an alkali metal hydride.

21. The method of claim 12, wherein the alkali metal is sodium or potassium.

22. The method of claim 12, wherein said medium is dimethylformamide.

23. The method of claim 12, wherein said medium is dimethylsulfoxide.