Surface active N-Halamine compounds

Details Surface active N-Halamine compounds Surface active N-Halamine compounds

2000-11-10

2002-10-22

Solola, T. A. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06469177

ABSTRACT:

FIELD OF THE INVENTION
The following invention relates to disinfectant compounds that act as biocides to an array of microorganisms. The biocides are comprised of cyclic N-halamines that are biocidal when they come in contact with hallogen-sensitive organisms for a specific contact time. This is achieved by coating the N-halamine on a substrate; such as, but not limited to: glass, metal, wood, plastic, concrete, and fabric.
BACKGROUND OF THE INVENTION
Current surface contact biocides for the use of producing a sterile environment such as for medical tables, surgical equipment, fabric materials, gloves, catheter tubing, piping, industrial and commercial surfaces, swimming pools, floors, can and bottle liners, food production equipment and liners, and various medical and dental applications do not exist or are severely limited in their biocidal abilities. Most commonly used water-soluble disinfectants which contain free halogen have severely limited lifetimes, produce adverse reactions to their environment, and produce toxic by-products. Disinfectants which do not contain free halogen, such as quaternary ammonium and phenolic compounds, are only effective towards specific organisms, are water soluble, and can cause skin and eye irritation. Commercially employed hydantoins, cyanurates, oxazolidinones (Kaminski et al., U.S. Pat. Nos. 4,000,293 and 3,931,213), imidazolidinones (Worley et al., U.S. Pat. Nos. 4,681,948; 4,767,542; 5,057,612; 5,126,057), and polymeric N-halamines (Worley et al., U.S. Pat. Nos. 5,490,983 and 5,670,646) are much more stable than free halogen, ozone, and chlorine dioxide, and are more versatile than phenolic and quaternary ammonium compounds.
Currently only a few disinfectant surfaces have been prepared, most of which focus on quaternary ammonium compounds (quats) anchored on polymer backbones (Hazziza-Laskar et al.,
J. Appl. Polym. Sci.,
50:651 (1993); Nurdin et al.,
J. Appl. Polym. Sci.,
50:663 (1993); Nurdin et al.,
J. Appl. Polym. Sci.,
50:671 (1993); Hazziza-Laskar et al.,
J. Appl. Polym. Sci.,
58:77 (1995)) which are then cast as films. Although these films are biocidal, their limitations are that they need long contact times to kill the organisms, the surface cannot be reactivated once the biocidal activity is lost, the films are relatively expensive to make, and the films are partially water soluble. Other types of surface active disinfectants are polymeric phosphonium materials (Kanazawa et al.,
J. Polym. Sci.,
Part A:
Polym. Chem.,
31:1467 (1993);
J. Appl. Polym. Sci.,
52:641 (1994)), modified polyesters, polyethers and benzimidiazoles (Oh et al.,
J. Appl. Polym. Sci.,
52:583 (1994);
J. Appl. Polym. Sci.,
54:859 (1994); Cho et al.,
J. Macromol. Sci., Pure Appl. Chem.,
A32:479 (1995)) which are resistant to several types of microorganisms, but the biocidal moiety cannot be regenerated once exhausted, the films are costly to make, and they can be water soluble.
Therefore, there is a need for a surface active biocide that is inexpensive to manufacture, can regenerate its biocidal activity, is water insoluble when necessary, can kill a broad spectrum of microorganisms, does not affect its environment unfavorably, and requires relatively short contact times to inactivate microorganisms when necessary. There is also a need for the contact biocide to be applied to numerous substrates such as glass, wood, metal, fibrous materials, and concrete to maximize the applications for its use.
SUMMARY OF THE INVENTION
The present invention relates to a monomer and its corresponding polymers and copolymers comprising a cyclic N-halamine unit, wherein the cyclic N-halamine unit comprises: a 5-membered ring wherein 3 members of the ring are carbon, 1 member of the ring is a nitrogen heteroatom, and 1 member of the ring is oxygen heteroatom; wherein one carbon member comprises a carbonyl group; wherein one non-carbonyl carbon member is attached to an acryloxymethyl linkage which is substituted with moieties R
2
, R
3
, and R
4
, which moieties are selected from the group consisting of hydrogen, C
1
-C
4
alkyl, benzyl, substituted benzyl, phenyl and substituted phenyl; wherein said non-carbonyl carbon member is also joined to a moiety R
1
selected from the group consisting of hydroxyl, C
1
-C
4
alkyl, benzyl, substituted benzyl, phenyl and substituted phenyl; and wherein the nitrogen heteroatom is joined to a moiety X selected from the group consisting of chlorine, bromine or hydrogen. The general structure for one embodiment of the monomer is shown below.
wherein X is chlorine, bromine or hydrogen; R
1
is selected from the group consisting of hydroxyl, C
1
-C
4
alkyl, benzyl, substituted benzyl, phenyl and substituted phenyl; R
2
, R
3
and R
4
are each independently selected from the group consisting of hydrogen, C
1
-C
4
alkyl, benzyl, substituted benzyl, phenyl and substituted phenyl. A method of using the monomer of structure I for producing a biocidal material or coating through halogenation with chlorine or bromine is also disclosed. The biocidal material can be applied as a coating or film onto a plurality of substrates useful for their disinfectant properties. The biocidal properties can be regenerated by renewed halogenation in chlorine or bromine solutions.
The present invention also relates to biocidal polymers comprising a cyclic N-halamine unit linked at a carbon atom to a second N-halamine unit via acryloxymethyl linkage wherein each N-halamine unit comprises a 5 membered ring, wherein 3 members of the ring are carbon, 1 member of the ring is nitrogen heteroatom, and 1 member of the ring is oxygen heteroatom; wherein 1 carbon member comprises a carbonyl group; wherein 1 non-carbonyl carbon member is linked to the second N-halamine unit via acryloxymethyl linkage, which linkage is substituted with moieties R
2
, R
3
and R
4
each of which are independently selected from the group consisting of hydrogen, C
1
-C
4
alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl; wherein said non-carbonyl carbon member is also joined to an R
1
substituent selected from the group consisting of hydroxyl, C
1
-C
4
alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl; and wherein the nitrogen heteroatom is joined to a moiety X selected from the group consisting of chlorine and bromine.
The invention also relates to biocidal copolymers comprising a cyclic N-halamine monomeric unit linked at a carbon atom by an acryloxymethyl linkage to a second monomeric unit, wherein the second monomeric unit is any polymerizable olefin, e.g., acrylic acid, vinyl acetate, vinyl chloride, styrene, acrylonitrile, propylene, or ethylene; wherein the N-halamine monomeric unit comprises a 5 membered ring, wherein 3 members of the ring are carbon, 1 member of the ring is nitrogen heteroatom, and 1 member of the ring is oxygen heteroatom; wherein 1 carbon member comprises a carbonyl group; wherein I non-carbonyl carbon member is linked to the second monomeric unit via acryloxymethyl linkage, which linkage is substituted with moieties R
2
, R
3
and R
4
each of which are independently selected from the group consisting of hydrogen, C
1
-C
4
alkyl, phenyl, substituted phenyl, benzyl and substituted benzyl; wherein said non-carbonyl carbon member is also joined to an R
1
substituent selected from the group consisting of hydroxyl, C
1
-C
4
alkyl, phenyl, substituted phenyl, benzyl and substituted benzyl; and wherein the nitrogen heteroatom is joined to a moiety X selected from the group consisting of chlorine and bromine.
The invention also relates to biocidal grafted copolymers comprising a cyclic N-halamine unit linked at a carbon atom by an acryloxymethyl linkage to a polymer backbone wherein the polymer backbone is any commercial polymer, e.g., poly-vinyl chloride, poly-acrylonitrile, poly-vinyl acetate, poly-vinyl alcohol, poly-styrene, cellulose, and cellulose blends with polyester, rayon, spandex, and poly-urethanes; wherein the N-halamine unit comprises a 5 membered ring, wherein 3 members of the ring are carbon, 1 member of the ring is

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