Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1996-02-22
2003-06-10
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S770000, C514S772000, C514S970000, C514S975000, C514S241000
Reexamination Certificate
active
06576633
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to anhydrous, liquid antimicrobial suspension compositions of quaternaries prepared from hexamethylenetetramine and certain halohydrocarbons in admixture with an anhydrous carrier liquid and a thixotropic material. These compositions are chemically, physically and color stable when stored over extended time periods of at least six months.
BACKGROUND OF THE INVENTION
Quaternaries prepared from hexamethylenetetramine and halohydrocarbons are old and well known antimicrobial agents as disclosed in
Applied Microbiology
, Volume 10, pages 211-216, 1962. For example, 1-(benzyl)-3,5,7-triaza-1-azoniaadamantane chloride is prepared from the reaction of hexamethylenetetramine with benzyl chloride; 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride and the cis- and cis-trans isomers thereof are prepared from the reaction of hexamethylenetetramine with 1,3-dichloropropene; 1-(&agr;-(2-xylyl))-3,5,7-triaza-1-azoniaadamantane chloride is prepared from the reaction of hexamethylenetetramine with &agr;-chloro-2-xylene and 1-(methylacetyl)-3,5,7-triaza-1-azoniaadamantane chloride prepared from the reaction of hexamethylenetetramine with methylchloroacetate.
The compound 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride is commercially available from The Dow Chemical Company under the trademark DOWICIL™ 200, hereinafter referred to as the “cis-compound,” and the various cis-/trans-mixtures of said compound containing from about 50 to 99.5 percent cis-isomer and about 50 to 0.5 percent trans-isomer are commercially available from The Dow Chemical Company under the trademarks DOWICIL™ 100 and DOWICIL™ 75.
The quarternary compounds are particularly effective antimicrobial agents and have been used in products such as, emulsified cutting oils, latexes, latex and emulsion paints, printing inks, glues and adhesives, coatings, sizings, hydraulic fluids and paper pulp dispersions.
Many antimicrobial agents used in cosmetic and personal care formulations, for example, are sold in the form of powder compositions. Formulators who use antimicrobial powder compositions in cosmetic and personal care formulations find themselves further faced with the many handling concerns associated with powders such as dust and mixing problems during product formulation. Many of the known quarternary compound powder compositions cannot conveniently be used in certain personal care products such as hand creams, lotions, shampoos and hand soaps because of mixing and stability problems.
It is therefore often desirable to employ the quarternary compound antimicrobial agents in the form of liquid concentrates since in many situations, liquids are more convenient to handle, and the inherent concerns associated with the use of powders, as mentioned hereinabove, are avoided. Such liquid compositions should be both chemically and physically stable over extended time periods of at least six months under a variety of storage conditions while maintaining their antimicrobial activity. Such compositions should also remain substantially color stable under said storage conditions.
Previous efforts to develop liquid concentrates of quarternary compounds which are homogeneous, color stable, and chemically and physically stable for extended periods of time have been generally unsuccessful. For example, 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride and its various cis- and trans-mixture are initially antimicrobially active in the presence of water and many other polar solvents, they do not however possess sufficient stability in such polar solutions to remain stable when held under conventional storage conditions for long periods of time.
The known liquid compositions of the cis- or cis/trans-isomers of 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride have not been found acceptable for commercial use as many of the solvents or carrier liquids employed in these compositions do not provide sufficient stability for said compositions. For example, many organic solvents such as methanol, dimethylformamide, dimethylsulfoxide, monoethanolamine and, propylene glycol methyl ether, and the like, when in a solution, suspension or slurry with the cis-compound or the cis/trans-compounds over a short time form a marked darkening of the color of the composition. This characteristic is particularly unsuitable in the cosmetic industry, latex industry or any other such industry where color is an important parameter.
It is also well known that the quarternary compounds and specifically the cis- and the cis/trans-isomers of 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride compounds when present in greater than 10 percent by weight in aqueous compositions will darken in color and lose much of their antimicrobial activity after a time period as short as one month. For example, a conventional 30 percent aqueous solution of either the cis- or the cis/trans-compound degrades in color in less than 24 hours after admixture and shows about a 30 percent chemical degradation within one month.
It would be therefore desirable to provide homogeneous, color stable, and chemically and physically stable liquid concentrate compositions containing quarternary compounds and specifically 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride and its cis- and cis/trans-isomers as active ingredients.
SUMMARY OF THE INVENTION
This invention relates to stable liquid suspension concentrate compositions comprising quaternaries from the group consisting of 1-(benzyl)-3,5,7-triaza-1-azoniaadamantane chloride, 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride and the cis- and cis/trans isomers thereof, 1-(&agr;-(2-xylyl))-3,5,7-triaza-1-azoniaadamantane chloride and methyl 1-(3,5,7-triaza-1-azoniaadamantane chloride)acetate in admixture with an anhydrous carrier liquid and a thixotropic material as an anti-settling agent.
This invention further relates to stable liquid suspension concentrate compositions comprising a 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride compound in either the cis or cis/trans-isomer form in admixture with an anhydrous carrier liquid and a thixotropic material as an anti-settling agent. The above compositions are substantially stable to color or chemical degradation and to changes in their physical makeup when they are stored under conventional storage conditions for time periods of up to six months or more.
The suspension compositions of the present invention containing the quaternaries in admixture with the anhydrous carrier liquid and the thixotropic material are liquids which remain substantially color stable for extended periods of at least six months under conventional storage, packaging, and handling conditions.
The liquid suspension concentrate compositions of the present invention are also chemically and physically stable and contain the quaternaries in an amount from about 0.9 to about 75 percent by weight, preferably from about 30 to about 50 percent by weight; the anhydrous carrier liquid is present in an amount from about 25 to about 99 percent by weight; and the thixotropic material is present in an amount from about 0.1 to about 10 percent by weight, preferably from about 0.2 to about 6.0 percent by weight, most preferably from about 0.3 to about 3.0 percent by weight.
As used herein, the term “anhydrous” describes a material composition wherein the color thereof remains substantially the same for the above defined time period having a water content of less than 2.0 percent by weight.
As used herein, the term “color stable” describes a composition wherein the color thereof remains substantially the same for the above defined time period.
As used herein, the term “chemically stable” describes a composition wherein there is substantially no chemical degradation thereof and/or loss of antimicrobial activity for the above-defined time period.
As used herein, the term “physically stable” describes a composition wherein there is substantially no particle separation or settling for the above-defined time period.
The suspension c
Brondsema Philip J.
Young Tracy L.
Pak John
The Dow Chemical Company
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