Anti-microbic agent

Details Anti-microbic agent Anti-microbic agent

2000-01-19

2002-06-11

Levy, Neil S. (Department: 1617)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Wearing apparel, fabric, or cloth

C424S078180, C424S405000, C424S407000, C424S411000, C424S414000, C424S430000, C424S431000, C523S111000, C523S122000

Reexamination Certificate

active

06403113

ABSTRACT:

This application is a 371 of PCT/US98/14690 filed Jul. 16, 1998.
This invention relates to the use of certain copolymers and derivatives thereof as anti-microbic agents.
Many applications exist where it is necessary or at the very least an advantage for agents to be present which demonstrate anti-bacterial, anti-mycotic activity or both, resulting in the control of bacterial and/or fungal growth. For example, an apparatus or article as a whole or in part may have the property of suppressing bacterial and fungal growth. Control of bacterial and/or fungal growth may be through the prevention or inhibition of the growth of such microbes.
U.S. Pat. No. 4,248,685 discloses random interpolymers which can be used as superabsorbent materials prepared by the polymerization in aqueous medium of (A) a mixture of monomers comprising (1) up to about 90% by weight of an ester of an a, &bgr;-olefinically unsaturated carboxylic acid and a monohydric or polyhydric alcohol having a terminal quaternary ammonium group and (2) at least one a, &bgr;-olefinically unsaturated comonomer, in the presence of (B) a crosslinking agent comprising a difunctional monomer derived from an a, &bgr;-olefinically unsaturated carboxylic acid, which is bacteriostatic and is capable of adsorbing large multiples of its own weight of water.
WO92/09289 teaches an improved method for treating diaper rash of neonates, infants, children and incontinent adults which entails applying to the site of diaper rash a composition comprising 15-40% of a copolymer or a derivative thereof, of a lower alkyl vinyl ether and maleic acid dispersed in a semisolid ointment base.
U.S. Pat. No. 4,381,784 discloses an absorbent device designed to absorb blood or blood-like fluids such as a sanitary napkin which is combined with a blood gelling agent which includes, amongst others, maleic anhydride copolymers.
It has now been found that certain copolymers can be used to control or prevent the growth of microbic agents such as bacteria and fungus. It has further been found that certain derivatives of these copolymers also have anti-bacterial and anti-mycotic properties. The finding that the copolymers of the invention and derivatives thereof which are preferably of high molecular weight can be used as anti-bacterial and/or anti-mycotic agents provides many advantages over anti-microbic agents of the prior art, in particular, due to the large molecular weight and polymeric character of the anti-microbic agents of the invention. Furthermore, the copolymers or derivatives per se or blends of said copolymers or derivatives can be formed into articles or incorporated into articles in the form of films, fibers, adhesives etc.. The copolymers of the invention have a low toxicity due to their high molecular weight and possess intrinsic anti-bacterial and anti-mycotic activity. The use of the copolymers of the invention in the manufacture of certain articles may avoid the need to incorporate a separate constituent part to impart anti-microbic properties into an article. Moreover many anti-microbial substances available in the prior art are unsuitable for use in contact with humans and animals due to their toxicity. This applies both to non-polymeric and polymeric substances. Most of the polymers already known to possess anti-bacterial activity, show an inverse proportionality between molecular weight (and so toxicity) and anti-bacterial activity. Hence while such substances possess high biological activity at low molecular weights (insufficiently high in particular to avoid significant toxic effects on humans and animals), their activity is rapidly lost or become too low, when the molecular weight increases towards the range of real polymers and consequently, also their toxicity for superior organisms decreases. Hence, there is a need to combine suitable polymeric properties required for effective formation of a part or the whole of an article with inherent anti-bacterial and/or anti-mycotic properties to provide an article having the necessary physical parameters but demonstrating anti-microbic activity also.
The invention relates to the use of a copolymer comprising at least two different ethylenically unsaturated monomers A and B or a derivative of said copolymer as an anti-bacterial, an anti-mycotic agent or both wherein monomer A is according to the formula:
R
1
—CH═CH—R
2
and wherein monomer B is according to the formula:
R
3
—C(R
1
)═C(R
2
)—R
4
wherein R
1
and R
2
are independently selected from hydrogen; hydroxy; halogen; carboxy; sulfo; phenyl; phenoxy; C
1-6
alkyl, C
1-6
alkoxy, C
1-6
aminoalkyl, C
1-6
haloalkyl wherein the halogen is selected from chlorine, bromine, iodine, and fluorine, preferably chlorine; C
1-6
alkylphenyl; amino and C
1-6
alkylamino, R
3
is an acidic group or a derivative thereof and R
4
is a group selected from any of the definitions given hereinbefore for R
1
, R
2
or R
3
, with the proviso that neither monomer A nor monomer B is an ester having a quaternary ammonium compound.
According to an embodiment of the invention, monomer A is according to the formula:
R
1
—CH═CH—O—R
2
wherein R
1
is as defined hereinbefore and R
2
is selected from phenyl, C
1-6
alkyl, C
1-6
aminoalkyl, C
1-6
haloalkyl, C
1-6
alkylphenyl, and C
1-6
alkylamino. More preferably, R
1
is hydrogen and R
2
is C
1-6
alkyl.
According to a further embodiment, monomer B is a dibasic acid according to the formula:
R
3
—C(R
1
)═C(R
2
)—R
4
in which R
3
and R
4
are both carboxyl and R
1
and R
2
are as defined hereinbefore, and according to an embodiment of the invention both R
1
and R
2
are hydrogen.
It is preferred that when the copolymer of the invention is comprised of more than two monomers, monomers A and B form at least 90% in moles of the total copolymer. It is further preferred that the molar ratio of monomers A and B is from 60:40 to 40:60, it being most preferred that the copolymer comprises a substantially equal molar content of monomers A and B.
According to a further embodiment, the copolymer is substantially an alternate copolymer where monomers A and B alternate according to the structure:
—A—B—A—B—A—B—A—B—
The copolymer of the invention may further comprise monomers C, which may form up to 10% in moles of the total copolymer and individually, may form up to 5% in moles of the total monomer. The additional monomers may be any ethylenically unsaturated monomer provided that they are polymerisable with monomers A and B. The additional monomer may occupy any position in the polymer chain, but preferably the additional monomers are homogenously dispersed, more preferably according to one of the following structure:
—A—C—B—
—A—C—A—
or
—B—C——.
According to a further embodiment of the invention, R
3
in monomer B is a sulfo or carboxy group or a derivative thereof and R
4
is an acidic group or a derivative thereof, preferably also a sulfo or carboxy group or a derivative thereof. When two contiguous carboxy groups are present in the copolymer of the invention, the cyclic anhydride derivative may be also usefully employed.
The acidic groups of monomers A and B can be defined as meaning that all the acidic groups of the monomers may be present either as free acidic groups or as corresponding anhydrides or alternatively, as derivatives or as derivatives that can be formed from said free acid groups or corresponding anhydrides, for example, esters, salts, amino-ammonium salts, amides, imides, complexes with inorganic and organic compounds etc, by reaction under suitable conditions conventionally used.
Specific examples of monomer A include, but are not limited to: alkyl vinyl ethers selected from vinyl methyl ether, vinyl ethyl ether, vinyl propyl ether, vinyl isopropyl ether, vinyl n-butyl ether, vinyl isobutyl ether, vinyl n-amyl ether, vinyl n-hexyl ether; and alkoxy alkyl vinyl ethers selected from methoxyethyl vinyl ether, ethoxyethyl vinyl ether, propoxyethyl vinyl ether, butoxyethyl vinyl ether, methoxyethoxyethyl vinyl ether, ethoxyethoxyethyl vinyl ether, butoxyethoxyethyl vinyl ether.
The m

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