Biocidal particles of methylated polystyrene

a technology of methylated polystyrene and biocidal particles, which is applied in the field of biocidal particles of methylated polystyrene, can solve the problems of difficult preparation of poly-1,3-dichloro-5-methyl-5-(4′-vinylphenyl)hydantoin as uniform particles, and noticeable chlorine odor, so as to achieve reasonable biocidal efficacy, less chlorine outgassing, and less steps

Inactive Publication Date: 2010-02-04
AUBURN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0018]One embodiment of the invention relates to the disinfection and control of odor in bodily fluids in applications such as disposable diapers, infant swimwear, incontinence pads, bandages, sanitary napkins, pantiliners, and the like.
[0019]Biocidal compounds made according to the present invention using chloromethylated polystyrene beads as a starting material require fewer steps to synthesize and produce less chlorine outgassing than the previously produced N-halamine polymer of U.S. Pat. No. 5,490,983 to Worley et al., while maintaining a reasonable biocidal efficacy. Chloromethylated polystyrene beads have been utilized in the past to prepare ion-exchange resins and weakly biocidal polyquaternary ammonium salts (U.S. Pat. No. 4,349,646 and U.S. Pat. No. 4,826,924), but have not been functionalized with potent biocidal N-halamine moieties.

Problems solved by technology

However, the preparation of poly-1,3-dichloro-5-methyl-5-(4′-vinylphenyl)hydantoin as uniform particles is tedious, requiring a three-step synthesis and the use of reagents such as potassium cyanide and carbon disulfide, as well as a high-pressure reactor in one of the steps.
When fully chlorinated, the polymer binds about 20% by weight chlorine, which causes a noticeable chlorine odor.

Method used

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  • Biocidal particles of methylated polystyrene
  • Biocidal particles of methylated polystyrene

Examples

Experimental program
Comparison scheme
Effect test

example 1

A Representative Preparation of Chlorinated Methylated Polystyrene Hydantoin Beads

[0037]Porous beads of 5.6% crosslinked chloromethylated polystyrene (containing 20.85% by weight chlorine) obtained from Suqing Group (Jiangyin, Jiangsu, PRC) having particle sizes in the range 180 to 425 μm, but undetermined pore sizes, were cleaned by soaking them in acetone (400 mg / mL) for 30 minutes at 25° C. and then by passing 3 portions of acetone (0.5 mL per g) through them in a filter funnel. Following drying to constant weight under vacuum at 50° C., 20.3 g (about 0.12 mole of active chlorine) of the beads were suspended in 150 mL of anhydrous DMF in a 250 mL flask fitted with a condenser. Then 16.5 g of anhydrous potassium carbonate (0.12 mole) and 15.4 g (0.12 mole) of 5,5-dimethylhydantoin were added, and the mixture was stirred for 72 hours at 95° C. After cooling the mixture to 25° C., suction filtration was used to isolate the beads. The beads were then soaked in 500 mL of boiling water...

example 2

An Alternative Representative Preparation of Chlorinated Methylated Polystyrene Hydantoin Beads

[0039]The potassium salt of 5,5-dimethylhydantoin was prepared by reacting 25.6 grams (0.2 mole) of 5,5-dimethylhydantoin with 11.2 grams (0.2 mole) of potassium hydroxide in 100 mL of boiling ethanol with stirring. The ethanol and product water were removed under vacuum to obtain the white salt. The salt was added to 200 mL of anhydrous DMF and heated to 95° C. until all of the salt dissolved. Then 8.12 grams (about 0.048 mole of active chlorine) cleaned chloromethylated polystyrene beads were added and the mixture was heated with stirring at about 100° C. for 12 hours. The unreacted potassium salt of the hydantoin and the DMF were recycled for further use, and the beads functionalized with hydantoin groups were washed and dried under vacuum at 85° C. until constant weight as in Example 1. The weight of the beads prepared in this manner was 11.0 grams (35.5% by weight add-on). Chlorinatio...

example 3

Representative Preparation of Brominated Methylated Polystyrene Hydantoin Beads

[0040]Methylated polystyrene hydantoin beads (5.0 grams) prepared as described in Example 1 were suspended in a solution containing 40 mL of 10% sodium hypobromite and 40 mL of water. The pH was adjusted to 7.0 using 2 N acetic acid. The mixture was stirred for 1 hour at 25° C. The brominated beads were removed by filtration, washed with three 100 mL portions of water, and dried under vacuum until constant weight was obtained. The bromine content determined by sodium thiosulfate / iodometric titration was 8.2% by weight. An infrared spectrum of a small sample of the beads (crushed to a powder) in a KBr pellet exhibited prominent bands at 1714 and 1776 cm−1 consistent with the presence of a monobrominated hydantoin functional group.

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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.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This application is a division of application Ser. No. 10 / 287,449, filed Oct. 31, 2002, which is herein expressly incorporated by reference.FIELD OF THE INVENTION[0002]The present invention relates to the use of highly crosslinked, porous N-halamine biocidal polymers for inactivating pathogenic microorganisms and viruses in water and air filtration applications, thereby rendering the water and / or air safe for human consumption. The invention also relates to the use of these polymers for inactivating microorganisms such as bacteria, fungi, and yeasts that can cause noxious odors and infections in commercial products, such as disposable diapers, infant swimwear, incontinence pads, bandages, sanitary napkins, pantiliners, sponges, mattress covers, shoe inserts, animal litter, carpets, fabrics, and air filters, thereby rendering the products free of noxious odors and pathogenic organisms under normal use conditions.BACKGROUND OF THE INVENTION[...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F212/08A01N59/00C08F8/00
CPCA01N59/00C08F8/30C08F8/24C08F112/08C08F8/02A01N25/00
Inventor WORLEY, SHELBY D.CHEN, YONGJUN
Owner AUBURN UNIV
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