Biocidal polystyrene hydantoin particles

Details Biocidal polystyrene hydantoin particles Biocidal polystyrene hydantoin particles

2001-09-06

2003-04-15

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Solid synthetic organic polymer as designated organic active...

Nitrogen heterocycle

C424S405000, C424S078370, C424S489000, C424S497000

Reexamination Certificate

active

06548054

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the manufacture, product, and method of using a highly crosslinked polystyrene N-halamine biocidal polymer. The biocidal polymer is produced under heterogeneous conditions due to its highly crosslinked nature, and in one instance can have pores.
BACKGROUND OF THE INVENTION
While a variety of biocidal polymers (e.g., quaternary ammonium salts, phosphonium materials, halogenated sulfonamides, and biguanides—see
Trends Polym. Sci.
4:364 (1996)) have been synthesized and tested for biocidal activity, a relatively new class known as cyclic N-halamines has been shown to have far superior properties including biocidal efficacy, long-term stability, and rechargability once the efficacy has been lost. Such a material is poly-1,3-dichloro-5-methyl-5-(4′-vinylphenyl)hydantoin which is an inexpensive derivative of poly-styrene, and which was first described in U.S. Pat. No. 5,490,983, now incorporated herein by reference. Subsequent disclosures of its biocidal properties for use in disinfecting applications for water filters have recently occurred [see
Ind. Eng. Chem. Res.
33:168 (1994);
Water Res. Bull.
32:793 (1996);
Ind. Eng. Chem. Res.
34:4106 (1995);
J. Virolog. Meth.
66:263 (1997);
Trends in Polym. Sci.
4:364 (1996);
Water Cond
. &
Pur.
39:96 (1997)]. The polymer is effective against a broad spectrum of pathogens including
Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, Klebsiella terrigena, Legionella pneumophila
and rotavirus, among others, causing large log reductions in contact times of the order of a few seconds in water disinfectant applications. Furthermore, it is effective at pH values at least in the range 4.5 to 9.0 and at temperatures at least in the range 4° C. to 37° C., and it is capable of action even in water containing heavy chlorine demand caused by bioburden.
This biocidal polymer is insoluble in water and organic compounds and will thus not migrate in liquid media. It is stable for long periods of time in dry storage (a shelf life of at least one year at ambient temperature) and can be produced on an industrial scale. Furthermore, all evidence obtained to date suggests that the material is non-toxic and non-sensitizing to humans and animals upon contact.
A variety of microorganisms such as certain bacteria, fungi, and yeasts are capable of aiding the decomposition of bodily fluids such as urine and blood, or in the formation of biofilms, which produce undesirable odors in otherwise useful a commercial products. For example, bacteria such as
Bacterium ammoniagenes
and
Proteus mirabilis
are known to accentuate the decomposition of urea to form noxious ammonia gas through a urease enzyme catalysis mechanism (see for example U.S. Pat. No. 5,992,351). The same polymer mentioned above (poly-1,3-dichloro-5methyl-5-(4′-vinylphenyl)hydantoin) has been shown to be effective at inactivating
Proteus mirabilis
and thus minimizing the undesirable odor created by ammonia gas (U.S. patent application Ser. No. 09/685,963, herein incorporated by reference). Also, the polymer is insoluble in bodily fluids so as not to migrate to skin surfaces, rendering it useful in applications such as disposable diapers, incontinence pads, bandages, sanitary napkins, and pantiliners.
However, the composition of poly-1,3-dichloro-5-methyl-5-(4′-vinylphenyl)hydantoin and use as a biocide for water-filter applications described in U.S. Pat. No. 5,490,983 and its use for odor control described in U.S. patent application Ser. No. 09/685,963 involved a form of the material which was a fine powder with a noticeable chlorine odor. In this form the material exhibited a tendency to cause excessive back-pressure in a water filtration application thereby slowing down flow rates, and the fine particles could potentially be aerosolized in an industrial setting causing concern for workers handling the material. Thus it was deemed necessary to find a method of creating the material as larger particles with less chlorine outgassing, while maintaining its biocidal efficacy.
SUMMARY OF THE INVENTION
The present invention relates to the manufacture, product and the use of novel highly crosslinked biocidal hydantoins in water and air filters and mixed with absorbent materials or as a coating for the prevention of noxious odors caused by the decomposition of organic materials contained in bodily fluids, on carpets and textile fibers, and in air filters or the like.
One embodiment of the invention is directed to a novel method of making highly crosslinked biocidal hydantoins from highly crosslinked polystyrene. A suitable amount of crosslinking is greater than 5%. In this form, the hydantoin is manufactured as particles rather than as a fine powder. In one embodiment the particle can include pores to increase the biocidal efficiency. Because of the highly crosslinked nature of the polymer, the reactions can proceed under heterogeneous conditions. In another embodiment the halogen loading can be controlled by either adjusting the pH or the halogen concentration during the halogenation step.
Another aspect of the invention is a novel highly crosslinked biocidal hydantoin. The hydantoin has polymeric chains having the following chemical formula:
wherein,
X and X′ are independently chlorine (Cl), bromine (Br), or hydrogen (H), provided that at least one of X and X′ is Cl or Br; and
R
1
is H or methyl (CH
3
). The amount of crosslinking is greater than 5%. In one embodiment of the invention, the hydantoin can be provided as a particle, wherein the particle shape is in the form of a bead. However, other embodiments can provide highly crosslinked hydantoin in any other shape. In one instance the bead is greater than 100 &mgr;m or from about 100 &mgr;m to about 1200 &mgr;m. In another embodiment, the present invention can have pores, wherein the average of the pore size is greater than about 10 nm or from about 10 nm to 100 nm. The biocidal hydantoin made in accordance with the invention has novel highly crosslinked N-halamine polymers of poly-1,3-dihalo-5-methyl-5-(4′-vinylphenyl)hydantoin, poly-1-halo-5-methyl-5-(4′-vinylphenyl)hydantoin, and the alkali salt derivative of the monohalo species, and mixtures thereof, wherein the halogen can be either chlorine or bromine.
A biocidal particle made in accordance with the invention can be used in ways to provide numerous advantages. By providing a plurality of biocidal particles into a collection, such as a filter device, a suitable method of inactivating pathogenic microorganisms and viruses contained in water or air streams by contacting the water or air streams with the filters is provided. The biocidal particles, or beads, will prevent or minimize noxious odors by inactivating microorganisms upon contact which enhance, through catalytic enzymology, the decomposition of organic matter in bodily fluids to ammonia or other noxious materials. In one instance, the biocidal beads can be mixed with an absorbent material to form a mixture. The mixture is then introduced into any article that will contact bodily fluids and the mixture will inactivate halogen sensitive organisms. A biocidal bead made in accordance with the invention, prevents or minimizes noxious odors on air filters by inactivation of microorganisms such as those which cause mildew and molds, as well as those odors emanating from any liquid or aerosol which might contact the surface of the beads.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
The present invention may be understood more readily by reference to the following detailed description of specific embodiments and the examples included therein.
As used herein, “biocidal polymer” refers to the novel N-halamine polymers named poly-1,3-dihalo-5-methyl-5-(4′-vinylphenyl)hydantoin, poly-1-halo-5-methyl-5-(4′-vinylphenyl)hydantoin, and the alkali salt derivative of the monohalo species, and mixtures thereof, wherein the halogen can be either chlorine or bromine, although this is not mean

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