Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-03-01
2002-08-06
Pryor, Alton (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C424S405000
Reexamination Certificate
active
06429220
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an antimicrobial composition. More particularly, the present invention relates to an antimicrobial composition which comprises an isothiazolone compound, suppresses decomposition of the isothiazolone compound and reduces irritation of skin caused by the isothiazolone compound.
BACKGROUND ART
Isothiazolone compounds such as 5-chloro-2-methyl-4-isothiazoline-3-one as a typical example exhibit an excellent antimicrobial property and are widely used as slime control agents, bactericides, algaecides and fungicides in various systems such as cooling water systems, paper and pulp industry, coating materials industry, adhesive materials industry, treatments of cutting oils and sewage treatments. However, isothiazolone compounds are very unstable and stability of agents containing these compounds must be improved in order to use the agents effectively. Therefore, various studies have been conducted on the improvement.
For example, in the specification of Japanese Patent Application Publication Showa 54(1979)-23968, complexes of isothiazolone compounds with metal salts such as calcium chloride and zinc chloride are proposed as a complex which have the activity for killing organisms, are useful for controlling various types of organisms, particularly microorganisms, and not easily decomposed in the presence of ordinary additives or contaminating substances or in severe conditions and show excellent heat stability. In the specification of the U.S. Pat. No. 3,870,795, it is reported that isothiazolone compounds can be stabilized by suppressing decomposition by addition of metal nitrates such as calcium nitrate and magnesium nitrate or metal nitrites such as sodium nitrite and calcium nitrite to solutions of isothiazolone compounds.
In the specifications of Japanese Patent Application Laid-Open Nos. Showa 61(1986)-56174 and Showa 61(1986)-212576, stabilized solutions of isothiazolone compounds prepared by addition of metal salts such as copper chloride, sodium chloride, magnesium chloride and copper nitrate to solutions of isothiazolone compounds such as 5-chloro-2-methyl-4-isothiazoline-3-one in propylene glycol, 1,5-pentanediol or benzyl alcohol, are proposed.
However, the above agents and solutions had drawbacks in that stability of the isothiazolone compounds markedly deteriorates when the agents and solutions are further diluted with water or organic solvents. In the specification of Japanese Patent Application Laid-Open No. Heisei 5(1993)-124917, a method for protecting isothiazolone compounds from decomposition using compounds containing sulfur such as L-cystine in combination with isothiazolone compounds is proposed. However, this method has a drawback in that L-cystine has a small solubility in water and hydrophilic organic solvents and it is difficult to mix L-cystine with isothiazolone compounds. Therefore, an antimicrobial compound which suppresses decomposition of isothiazolone compounds and shows excellent stability has been desired. Isothiazolone compounds often irritate skin and agents containing isothiazolone compounds must be handled with sufficient care. In the specification of Japanese Patent Application Laid-Open No. Heisei 5(1993)-246807, compositions containing polycation compounds such as polylysine and isothiazolone compounds are disclosed. However, it is known that these compositions do not show the effect of suppressing decomposition of the isothiazolone compounds.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide an antimicrobial composition which comprises an isothiazolone compound, suppresses decomposition of the isothiazolone compound and reduces irritation of skin caused by the isothiazolone compound.
As the result of extensive studies to achieve the above object, it was found that specific aminocarboxylic acids and derivatives thereof exhibit the effect of stabilizing isothiazolone compounds and reducing irritation of skin caused by isothiazolone compounds. The present invention has been completed on the basis this knowledge.
The present invention provides:
(1) An antimicrobial composition comprising an isothiazolone compound represented by general formula [1] or general formula [2] and an aminocarboxylic acid represented by general formula [3] or a derivative of the aminocarboxylic acid:
wherein R
1
represents hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, X and Y each represents hydrogen atom or a halogen atom or form a benzene ring in combination with carbon atoms at 4- and 5-positions of the isothiazolone compound, M represents a cation of an alkali metal, an alkaline earth metal, a heavy metal or an amine, Z represents an anion forming, in combination with the cation represented by M, a compound having a sufficient solubility to form a complex compound, a represents 1 or 2 and n represents an integer required for the anion represented by Z to satisfy a valence of the cation represented by M;
wherein R
2
represents hydrogen atom or an alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with carboxyl group, R
3
represents a linear or branched alkylene group having 1 to 5 carbon atoms, R
4
represents hydrogen atom or an alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with carboxyl group, carbamoyl group, hydroxyl group, phenyl group, hydroxyphenyl group, ureido group, methylthio group or 4-imidazolyl group, R
2
and R
4
form a heterocyclic group unsubstituted or substituted with hydroxyl group or oxo group in combination with N—(R
3
)
b
—C and b represents 0 or 1; and
(2) An antimicrobial composition according to (1), wherein the derivative of the aminocarboxylic acid represented by general formula [3] is a metal salt of the aminocarboxylic acid represented by general formula [3]; a compound having a structure in which the aminocarboxylic acids represented by general formula [3] of one or more types are bonded to each other through a peptide bond or a metal salt of the compound; a compound having a structure in which the aminocarboxylic acid represented by general formula [3] is bonded to a different aminocarboxylic acid through a peptide bond or a metal salt of the compound; an N-acetyl compound of the aminocarboxylic acid represented by general formula [3] or a metal salt of the compound; or an amide of the aminocarboxylic acid represented by general formula [3].
Preferable embodiments of the present invention include:
(3) An antimicrobial composition described in any of (1) and (2), which comprises 0.1 to 10% by weight of the isothiazolone compound represented by general formula [1] or general formula [2]; and
(4) An antimicrobial composition described in any of (1), (2) and (3), which comprises the aminocarboxylic acid or the derivative thereof represented by general formula [3] in an amount by mol 0.1 to 50 times the amount by mol of the isothiazolone compound represented by general formula [1] or general formula [2].
THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
The antimicrobial composition of the present invention comprises an isothiazolone compound represented by general formula [1] or general formula [2] and an aminocarboxylic acid represented by general formula [3] or a derivative of the aminocarboxylic acid.
In general formula [1] and general formula [2], R
1
represents hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, X and Y each represents hydrogen atom or a halogen atom or form a benzene ring in combination with carbon atoms at 4- and 5-positions of the isothiazolone compound, M represents a cation of an alkali metal, an alkaline earth metal, a heavy metal or an amine, Z represents an anion forming, in combination with the cation represented by M, a compound having a sufficient solubility to form a complex compound, a represents 1 or 2 and n repres
Usui Urara
Yagi Minoru
Frishauf Holtz Goodman & Chick P.C.
Kurita Water Industries Ltd.
Pryor Alton
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