Antimicrobial detergent composition

Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – With halogen – nitrogen – oxygen – or phosphorus containing...

Reexamination Certificate

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Details

C510S130000, C510S131000, C510S382000, C510S391000, C510S504000

Reexamination Certificate

active

06436890

ABSTRACT:

The present invention relates to antimicrobial detergent compositions which can be used for the purpose of removal of microorganism and deodorization of washings and sterilization and antibacterialization etc. in food factories, hospitals etc. and more specifically relates to antimicrobial detergent compositions which can be used favorably as detergents and softeners used for washing, detergents for cleaning, detergents used for walls, floors etc. of food factories, hospitals etc.
Clothes, bed sheets etc. used in the clinical spots used to be contaminated with blood, fluid, fat etc. and further with pathogens, viruses etc. For these clothes, bed sheets etc. detergents containing bactericide should be used to conduct not only washing but also such treatments as sterilization, antibacterialization, removal of microorganism, deodorization etc. Moreover, in cleaning, a bactericide is used usually with detergents to prevent clothes from contamination and keep them in a hygienic condition.
Recently, perhaps from cleanliness-oriented tendency, removal of microorganism and odor of clothes, bed sheets etc. are conducted also at general household together with washing and therefore detergents, softeners etc. containing bactericide appear on the market. Among these antimicrobial agents for washing, however, there are antimicrobial agents which appear adaptation of bacteria when used for longer period of time and lose effects of removal of microorganism, deodorization etc.
Infection of drug-resistant bacteria such as MRSA (Methicillin-resistant
Staphylococcus aureus
) to weak inpatients in hospitals has become a big social problem and it is desired to use detergents containing bactericides, which do not produce drug-resistant bacteria, as detergents to be used for walls, floors etc. Moreover, the existence of not only drug-resistant bacteria but also bacteria themselves matters in food factories and therefore there are desired highly safe antimicrobial agents which not only produce no drug-resistant bacteria but also have a wide antimicrobial activity spectrum.
The object of the present invention is to provide a highly safe antimicrobial agent which not only produces no drug-resistant bacteria but also has a wide antimicrobial activity spectrum even in case it is used for a longer period of time contained in detergents, softeners, detergents for cleaning and detergents used for walls, floor etc. of food factories, hospitals etc.
The present inventors have been intensively studying to solve the above-mentioned problem. As a result, this time, they found that bis-quarternary ammonium compounds represented by the following general formula (I) are suitable to be used for a longer period of time contained in detergents, softeners, detergents for cleaning and detergents used for walls, floor etc. of food factories, hospitals etc. (in the present specification they are collectively called as “detergent composition”), because they are highly safe to human body and natural environment, have a wide antimicrobial activity spectrum, produce no drug-resistant bacteria even in case of use for a longer period of time, and show effects against MRSA at a low concentration and completed the present invention.
Thus, according to the present invention, there is provided an antimicrobial detergent composition characterized by containing, as an antimicrobial agent, at least one bis-quaternary ammonium compound of the general formula
wherein the two R
1
may be the same or different and each represent an alkyl group of 1 to 18 carbon atoms or an alkenyl group of 3 to 18 carbon atoms; the two R
2
may be the same or different and each represent a hydrogen atom, a halogen atom, a hydroxyl group, an amino group, an alkyl group of 1 to 6 carbon atoms or an alkoxy group of 1 to 3 carbon atoms; R
3
represents an alkylene group of 1 to 18 carbon atoms, an alkenylene group of 3 to 18 carbon atoms or a phenylene or xylylene group which may optionally be substituted by an alkyl group of 1 to 18 carbon atoms, an alkoxy group of 1 to 6 carbon atoms or an alkoxycarbonyl group of 2 to 6 carbon atoms; Y
1
represents —NHCO—, —CONH—, —NHCS—, —COO—, —COS—, —O— or —S—; Y
2
represents —CONH—, —NHCO—, —CSNH—, —OOC—, —SOC—, —O— or —S—; and X represents anions.
The antimicrobial (i.e., antibacterial or antifungal) detergent compositions of the present invention will be more specifically described hereinbelow.
As used herein, the term “alkyl group” denotes a straight-chain or branched alkyl group, and examples thereof include methyl, ethyl propyl, isopropyl, butyl, isobutyl, sec-butyl pentyl, isopentyl, sec-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl isodecyl, dodecyl, tetradecyl, hexadecyl and octadecyl etc. From the viewpoint of antibacterial power, the alkyl groups represented by R
1
are preferably ones having 8 or more carbon atoms.
The term “alkenyl group” denotes a straight-chain or branched alkenyl group, and examples thereof include allyl, methallyl, pentenyl hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, hexadecenyl and octadecenyl, etc.
The term “alkoxy group” denotes an alkyloxy group in which the alkyl moiety has the above-described meaning, and examples thereof include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec- butoxy and tert- butoxy.
The term “alkylene group” preferably denotes a group of the formula &Parenopenst;CH
2
&Parenclosest;
n
. In this formula, n is preferably in the range of 2 to 18 and more preferably 3 to 8.
The term “alkenylene group” comprehends, for example, —CH═CH—, —CH═CH—CH
2
— and —CH
2
—CH═CH—CH
2
—.
The term “alkoxycarbonyl group” denotes an alkyloxycarbonyl group in which the alkyl moiety has the above-described meaning, and examples thereof include methoxycarbonyl and ethoxycarbonyl.
The term “halogen atom” comprehends fluorine, chlorine, bromine and iodine.
The term “anion” comprehends inorganic anions such as halogen ions (e.g., Cl

, Br

and I

) and nitrate ion (NO
3

); and organic acid anions such as acetate ion (CH
3
COO

) and propionate ion (C
2
H
5
COO

).
Among the compounds represented by the above formula (I), a preferred group of compounds are those of formula (I) in which the two R
1
may be the same or different, and each represents an alkyl group of 8 to 18 carbon atoms; the two R
2
may be the same or different, and each represents a hydrogen atom or a chlorine atom; R
3
represents an alkylene group of 3 to 8 carbon atoms, a phenylene group or a xylylene group; Y
1
represents —NHCO—, —CONH—, —COO— or —S—; Y
2
represents —CONH—, —NHCO—, —OOC— or —S—; and X represents a halogen ion or an acetate ion.
Specific examples of the compounds of the above formula (I) used as antimicrobial agents in the composition of the present invention are as follows:
N,N′-Hexamethylenebis(4-carbamoyl-1-decylpyridinium bromide) (“Dimer 38”; manufactured by INUI CORPORATION),
N,N′-hexamethylenebis(4-carbamoyl-1-decylpyridinium acetate) (“Dimer 38A”; manufactured by INUI CORPORATION),
4,4′-(tetramethylenedicarbonyldiamino)bis(1-decylpyridinium bromide) (“Dimer 136”; manufactured by INUI CORPORATION
4,4′-(tetramethylenedicarbonyldiamino)bis(1-decylpyridinium acetate) (“Dimer 136A”; manufactured by INUI CORPORATION),
1,4-tetramethylenebis(4-carbamoyl-1-hexadecylpyridinium bromide),
1,6-hexamethylenebis(3-carbamoyl-1-dodecylpyridinium bromide),
1,8-octamethylenebis(3-carbamoyl-1-tetradecylpyridinium bromide),
3,3′-(1,3-trimethylenedicarbonyldiamino)bis(1-decylpyridinium bromide),
4,4′-(p-xylyldithio)bis(1-octylpyridinium iodide),
3,3′-(m-xylyldithio)bis( 1-tetradecylpyridinium bromide),
N, N′-(p-phenylene)bis(4-carbamoyl-1-octylpyridinium bromide),
N,N′-(m-phenylene)bis(3-carbamoyl-1-dodecylpyridinium bromide),
4,4′-(p -phthalamido)bis(1-octylpyridinium bromide),
3,3′-(m-phthalamido)bis(1-octadecylpyridinium iodide),
4,4′-(1,8-octamethylenedioxy)bis(1-dodecylpyridinium bromide),
3,3′-(1,6-hexamethyl

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