Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-08-16
2001-07-03
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S373000, C514S385000, C514S386000, C514S387000, C514S389000, C514S390000, C514S391000, C514S392000, C514S393000, C514S394000, C514S395000, C514S396000, C514S397000, C514S398000, C514S399000, C514S400000, C514S401000, C514S499000, C514S500000, C514S694000, C514S697000, C514S698000, C514S970000, C514S971000, C514S973000, C424S630000, C424S631000, C424S632000, C424S633000, C424S634000, C424S635000, C424S637000
Reexamination Certificate
active
06255331
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to stable biocidtal compositions containing combinations of certain imidazole iodines and 3-isothiazolones. The present invention also relates to the use of low concentrations of copper salts to stabilize such compositions.
Microbicides are used commercially to prevent the growth of microbes in a variety of loci, such as cooling towers, metal working fluid systems, paints and cosmetics. One of the more important classes of microbicides is 3-isothiazolones. Many 3-isothiazolonies have achieved commercial success because they are very effective in preventing microbial growth under a wide variety of conditions and in a variety of loci. Among the most important 3-isothiazolones are 5-chloro--methyl-3-isothiazolone (“CMI”), 2-methyl-3-isothiazolone (“MI”), and mixtures thereof.
Although 3-isothiazolones are highly effective microbicides, some suffer from being unstable under certain conditions. Without the presence of a stabilizer, many 3-isothiazolones chemically degrade and lose microbicidal efficacy. Much research has been devoted to stabilizing 3-isothiazolones. A variety of stabilizers for 3-isothiazolone solutions are known and are described, for example, in U.S. Pat. No. 5,461,150 (Gironda et al) and U.S. Pat. No. 5,312,827 (Bayer et al).
Imidazolidines (which include hydantoins) are another class of Microbicides, and have been used for years in a variety of loci. The most well-known microbicide of this class is 1,3-dimethylol-5,5-dimethylhydantoin (“DMDMH”). DMDMH is generally provided as an aqueous solution, an anhyhdrous powder, or a solution in glycol. DMDMH is sold under various names, including Glydant®. These types of compounds are storage stable as supplied and do not require stabilizers to prevent chemical degradation.
STATEMENT OF THE INVENTION
The present invention is directed to stable biocidal compositions comprising at least one formaldelehyde-releasing imidazolidine, at least once 3-isothiazolone, a stabilizing amount of copper ion and solvent.
The present invention is also directed to a method of stabilizing a biocidal composition containing at least one formaldehyde-releasing imidazolidine and at least one 3-isothiazolone by the addition of a low level of copper ion.
DETAILED DESCRIPTION OF THE INVENTION
As used in this specification, the term “antimicrobial agent” refers both to a compound capable of inhibiting microbial growth (a preservative), and a compound capable of reducing microbial concentration (a disinfecting agent), within a given system. The term “antimicrobial activity” refers to the activity of the antimicrobial agents to eliminate, inhibit or prevent the growth of microorganisms. The terms “microbial organism,” “microbe” and “microorganism” are used interchangeably and refer to microorganisms such as, but not limited to: fungi, bacteria, and algae. The term “locus” or “loci” refers to all industrial system or product subject to contamination by microorganisms. The following abbreviations are used throughout this specification: AI=active ingredient, nmL=milliliter; g=grams. Unless specifically identified otherwise in this specification, percentages are by weight, ranges are to be read as inclusive, and ratios are weight ratios.
The present invention is based in part on the unexpected discovery that addition of 3-isothiazolones to imidazolidine compositions results in destabilization of the imidazolidines. A further unexpected discovery is that such combinations can be stabilized using low levels of copper ion.
Any 3-isothiazolone compound is useful in the compositions of the present invention. Suitable 3)-isothiazolone compounds include, but are not limited to: 5-chloro-2-methyl-3-isothiazolone; 2-methyl-3-isothiazolone; 2-ethyl-3-isothiazolone; 5-chloro-2-ethyl-3-isothiazolone; 4,5-d ichloro-2-methyl-3-isothiazolone; 2-n-octyl-3-isothiazolonie; 4,5-dichloro-2-n-i-octyl-3-isothiazolone; 1,2-benzisothiazolone; 4,5-trimethyleiie-2-methyl-3-isothiazolone; and mixtures thereof. When mixtures of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone are used, the weight ratio of 5-chloro-2-methyl-3-isothiazolone to 2-methyl-3-isothiazolone is generally 991 to 1:99, preferably 90:10 to 70:30.
The imidazolidines useful in the compositions of the present invention are any formaldehyde-releasing imidazolidines, particularly those of formula I and oligomers thereof:
wherein:
R
1
and R
2
are independently selected from: H; CH
2
OH; C
1
-C
4
alkyl, C
1
-C
4
alkenyl or C
1
-C
4
alkynyl optionally substituted with 0, S or N; provided that at least one of R
1
or R
2
is CH
2
OH; and
R
3
and R
4
are independently selected from: H; OH; halogen; C
1
-C
3
alkoxy; NR
5
C(O)NHR
6
; C
1
-C
4
alkyl, C
1
-C
4
alkenyl or C
1
-C
4
alkynyl optionally substituted with O, S or N; and
R
5
and R
6
are independently selected from: H; CH
2
OH; C
1
-C
4
alkyl, C
1
-C
4
alkenyl or C
1
-C
4
alkynyl optionally substituted with O, S or N.
Preferred imidazolidines include diazolidinylurea, imidazolidinyl ureas and the mono- and di-methylol 5,5-dimethylhydantoins. Most preferred is 1,3-dimethylol-5,5-dimethylhydantoin.
In general, a greater amount of imidazolidine than 3-isothiazolone will be present in the compositions of the present invention. Ratios of imidazolidine to 3-isothiazolone will vary greatly depending on the particular application, but will typically be between 1:1 and 800:1. It is preferred that the imidazolidine to 3-isothiazolone ratio be between 10:1 and 400:1, and most preferably between 75:1 and
A wide variety of copper salts are known in the art. Any copper salt which is sufficiently water soluble to provide the desired level of cupric ion in solution may be used. Suitable examples include, but are not limited to: copper sulfate, copper acetate, copper chloride, copper bromide, copper chlorate, copper perchlorate, copper nitrite and copper nitrate. Copper sulfate and copper nitrate are preferred. The copper salts are generally commercially available, for example, from Pfalz and Bauer (Waterbury, Conn.) and may be used without further purification.
The amount of cupric ion useful in the compositions of the present invention is typically 10 to 2500 ppm. The amount of cupric ion is preferably 10 to 1000 ppm, most preferably 10 to 100 ppm. Less cupric ion is needed where there is a lower concentration of 3-isothiazolone. As the concentration of the 3-isothiazolone is increased, proportionally more cupric ion is required to achieve the same stability. In general, the ratio of copper ion to 3-isothiazolone will be between 1:150 and 2:1. It is preferred to have a copper to 3-isothiazolone ratio between 1:75 and 1:1, and most preferably, between 1:15 and 1:5.
The solvents used in the compositions of the present invention can be water, organic solvent, or mixtures thereof. Any organic solvent is suitable as long as it is compatible with the end use and does not destabilize the antimicrobial agent. Suitable organic solvents include, but are not limited to: aliphatic and aromatic hydrocarbons, such as xylene anti mixtures of alkylbenzenes; halogenated aliphatic and aromatic hydrocarbons, such as ethylene dichloride and monochlorobenzene; alcohols, such as monohydric, dihydric, and polyhydric alcohols; aldehydes; ketones, such as acetone, methyl ethyl ketone, and methyl iso-butyl ketone; ethers; glycol ethers; glycol ether acetates; saturated and unsaturated fatty acids having at least four carbon atoms; esters, such as ethyl acetate, butyl acetate, glycol esters, and phthalate esters; and phenols. Preferred organic solvents are glycol ethers; glycol ether acetates; aliphatic and aromatic hydrocarbons; and alcohols. It is more preferred to utilize a mixture of glycol ethers or glycol ether acetates with water. Most preferred is water.
The compositions of the present invention may also include other stabilizers, such as metal nitrates, iodic acid or its salts, and various other inorganic salts and their like, which will not materially affect the performance of the combin
El A'mma Beverly Jean
Nagahashi Susan Lynn
Crimaldi Kenneth
Pak John
Rohm and Haas Company
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