N-halamine vinyl compounds and their polymeric biocides

Details N-halamine vinyl compounds and their polymeric biocides N-halamine vinyl compounds and their polymeric biocides

2000-03-24

2004-07-27

Stockton, Laura L. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S301400, C548S317100

Reexamination Certificate

active

06768009

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to heterocyclic vinylic amines reagents useful for the preparation of biocidal polymers. The biocidal polymers are usefull for generating medical and hygienic-use textiles.
BACKGROUND OF THE INVENTION
Contamination of polymeric materials by microorganisms such as pathogenic bacteria, odor-generating bacteria, molds, fungi and viruses is of great concern in the medical industry, the food and restaurant industries, as well as in consumer products. Survival of microorganisms on polymeric materials and transfer of these microorganisms between patients and health care workers (HCWs) has been demonstrated, and it is widely accepted that hospital gowns, patient drapes, carpeting and bedding materials, etc., can be elements in cross-infections. (see, Lidwell, O. M. et al.,
J Appl. Bact.
37:649 (1974)); Rubbo, S. D. and Saunders, J.,
J Hyg. Camb.,
61:507 (1963); Ransjo, U.,
J. Hyg. Camb.,
82:369 (1979); and Hambraeus, A.,
J. Hyg. Camb.,
71:799 (1973)). Medical gowns and uniforms currently in use provide barriers for HCWs, but have proven to be ineffectual in studies by numerous researchers. (see, for example, Beck, W. C. and Collette, T. S.,
Am. J. Surg.,
83:125 (1952); Smith, J. W. and Nichols, R. L.
Arch. Surg.,
126:756 (1991); Lovitt, S. A. et al.,
Am. J. Infect. Control,
20:185 (1992); Quebbeman, E. J. et al.,
Annal. Surg.,
214:614 (1991); Granzow, J. W. et al.,
Am. J. Infect. Control,
26:85 (1998)).
The occurrence of contaminated cleaning cloths in domestic applications has also been investigated. Results from several different studies indicate that more than half of the investigated dish cloths and cleaning cloths were contaminated by one or more of the following organisms:
Escherichia coli, Staphylococcus aureus, Streptococcus faecahis
and
Clostridium perfringens
(see, Scott, E. et al.,
J. Hyg. Camb.,
89:279 (1982); Tebutt, C. M.,
J. Hyg. Camb.,
97:81 (1986); and Scott, E. et al.,
J. Appl. Bact.,
68:271 (1990)). Further studies show that wiping hard surfaces with contaminated cloths can result in contamination of hands, equipment and other surfaces. (see, Mackintosh, C. A. and Hoffman, P. N.
J. Hyg. Camb.,
92:345 (1984)).
These findings suggest that biocidal properties should be an effective feature of medical and related healthcare and hygienic-use textiles. In general, hygenic-use textiles are made of synthetic polymers, and polymeric biocides have been reviewed by several researchers recently. (see, Vigo, T. L. (R. B. Seymour and R. S. Porter, Eds.),
Manmade Fibers: Their Origin and Development,
Elsevier Appl. Sci., p. 214 (1992); Vigo, T. L. (Gebelein, C. and Carraher, C., Eds.),
Biotechnology and Bioactive Polymers,
Plenum Press, p. 225 (1994); Worley, S. D. and Sun, G.,
Trends Polym. Sci.,
11:364 (1996)).
Among the currently investigated biocidal materials, N-halamines have been shown to provide almost instant and total kill of a wide range of microorganisms. (see, Worley, S. D. et al.,
Trends Polym. Sci.,
11:364 (1996)). There are many advantages associated with using N-halamine structures. First, they are stable in long-term use and storage over a wide temperature range. Second, they are regenerable when activity is lost due to normal use patterns. (see, Sun, G. et al.,
Polymer,
37:3753 (1996); Worley, S. D. et al.,
The Polymeric Materials Encyclopedia,
1, A-B, p. 550 (1996); Sun, G. et al.
Water Res. Bull.,
1996, 32:793 (1996)). More recently, N-halamine materials have been incorporated into cellulose-containing fabrics. (see, Bickert, J. R. et al.,
International Conference on Safety
&
Protective fabric '
98, 1998, p 1; Sun, G. et al.,
Textile Chem. Colorist,
6:26 (1998); Sun, G. et al.,
Textile Chem. Colorist,
31:21 (1999)). Results indicate that as little as 1% (wt) add-on of halamine structures provides powerful biocidal efficacy (6-7 log reduction) against the most common pathogens, at a contact time of two minutes.
U.S. Pat. No. 5,882,357, issued to Sun et al., on Mar. 16, 1999, discloses durable and regenerable microbiocidal textiles and methods for preparing the same. The microbiocidal textiles are prepared using a wet finishing process to covalently attach a heterocyclic N-halamine to a cellulose-based material or other polymeric material. The biocidal activity of the textiles can be regenerated by washing with a halogenated solution. In addition, U.S. Pat. No. 6,020,491, issued to Wonley et al., on Feb. 1, 2000, discloses cyclic amine monomers and polymers that are used to form biocidal N-halamine polymers. The polymers are useful as disinfectants for potable water, swimming pools, hot tubs, industrial water systems, cooling towers, air-conditioning systems, and the like.
In spite of the advances in the prior art, there remains a need for new monomeric units useful for generating polymers having microbiocidal activity. Polymers that can be used to generate microbiocidal fabrics, rubbers, plastics, paints, coatings, and articles are also needed. The present invention fulfills these and other needs.
SUMMARY OF THE INVENTION
In certain embodiments, the present invention provides heterocyclic vinylic amines that can be readily polymerized with most acrylic, substituted-acrylic and vinyl monomers. The polymers thus generated exhibit biocidal efficacy after exposure to a halogen source, such as chlorine bleach. Moreover, their antibacterial properties are durable and regenerable. As such, the present invention provides a compound having the formula
In Formula I, A is a functional group including, but not limited to, NH, N—R
8
and CR
1
R
2
, wherein R
8
is a halogen R
1
and R
2
, in Formula I are each a functional group including, but not limited to, optionally substituted (C
1
-C
6
)alkyl, optionally substituted (C
2
-C
6
)alkenyl, optionally substituted (C
2
-C
6
)alkynyl, optionally substituted cycloalkyl, optionally substituted (C
1
-C
6
)alkoxy, optionally substituted aryl and optionally substituted heteroaryl.
In an alternative embodiment, R
1
and R
2
and the carbon to which they are bound, join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring.
In Formula I, Q is a functional group including, but not limited to, C(O), NH, N—R
9
and CR
3
R
4
, wherein R
9
is a halogen. R
3
and R
4
, in Formula I are each a functional group including, but not limited to, optionally substituted (C
1
-C
6
)alkyl, optionally substituted (C
2
-C
6
)alkenyl, optionally substituted (C
2
-C
6
)alkynyl, optionally substituted cycloalkyl, optionally substituted (C
1
-C
6
)alkoxy, optionally substituted aryl and optionally substituted heteroaryl.
In an alternative embodiment, R
3
and R
4
and the carbon to which they are bound, join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring.
In Formula I, X is a functional group including, but not limited to, C(O)—NR
5
and CR
6
R
7
, wherein R
5
is a functional group including, but not limited to, hydrogen, halogen, optionally substituted (C
2
-C
6
)alkenyl and optionally substituted (C
1
-C
6
)alkyl. R
6
and R
7
, in Formula I, are each a functional group including, but not limited to, optionally substituted (C
1
-C
6
)alkyl, optionally substituted (C
2
-C
6
)alkenyl, optionally substituted (C
2
-C
6
)alkynyl, optionally substituted cycloalkyl, optionally substituted (C
1
-C
6
)alkoxy, optionally substituted aryl and optionally substituted heteroaryl;
In an alternative embodiment, R
6
and R
7
and the carbon to which they are bound, join to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring.
Z, in Formula I, is a functional group including, but not limited to, optionally substituted (C
1
-C
3
)alkylene, C(O), or a single bond. When Z is a single bond, a vinyl group is bonded directly to the ring nitrogen.
In another embodiment, the present invention provides a polymer comprising a mixture of monomeric units having the formulae
In Formula II, A is a functional group including, but not limited to, NH, N—R
8
and CR
1
R

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