Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – With halogen – nitrogen – oxygen – or phosphorus containing...
Reexamination Certificate
2001-05-15
2003-12-16
Boyer, Charles (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
With halogen, nitrogen, oxygen, or phosphorus containing...
C510S112000, C510S382000, C510S391000, C564S281000, C564S282000, C564S290000, C564S305000
Reexamination Certificate
active
06664224
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a novel quaternary ammonium salt and a process for the preparation thereof. The compound according to the present invention is useful as an antimicrobial agent such as preservative for eye drop.
BACKGROUND OF THE INVENTION
A quaternary ammonium salt having an antimicrobial activity has long been known and is now widely used. However, conventional quaternary ammonium salts are normally disadvantageous in that they show deteriorated sterilizing power and antimicrobial power due to the effect of saccharides, protein and lipid or in an acid range having a low pH value and have no effect on cellular spore.
As solutions to the foregoing problems, a compound having two structural units called quaternary ammonium per molecular has been proposed, which unit is capable of having four alkyl groups or other groups connected to one nitrogen atom, e.g., the antimicrobial agent comprising quaternary ammonium salt in JP-A-6-321902 (The term “JP-A” as used herein means an “unexamined published Japanese patent application”) and JP-A-10-114604. The compound disclosed in these published applications has methyl or ethyl groups connected thereto in a proportion of 2 or more per one of nitrogen atoms constituting the quaternary ammonium. Accordingly, this compound has a high antimicrobial activity and thus is a good compound from the standpoint of antimicrobial properties. This compound has been actually used as an antimicrobial agent. This compound has a high antimicrobial activity but it has been desired to improve the safety of this compound to human.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide a novel compound which exhibits a high antimicrobial activity and a wide antimicrobial spectrum and can be used as an antimicrobial agent having a high safety to human.
The other objects of the present invention will become apparent from the following detailed description and examples.
The present invention lies in a quaternary ammonium salt represented by the following general formula (1):
wherein R
1
and R
2
each represent a C
4-12
alkyl group and may be the same or different; R
3
represents a C
1-2
alkyl group; k represents an integer of from 0 to 4; X represents an inorganic or organic anion group; n represents the valence of the anion group X which is selected from 1 and 2; and m represents an integer of 2 when n is 1 or 1 when n is 2.
The compound of the invention can be obtained by the following reaction [I], [II] or [III]:
Reaction [I]
In the general formula (6), k represents an integer of from 0 to 4, and Y represents a chlorine atom, bromine atom or iodine atom.
In the general formula (7), R
1
and R
2
each represent a C
4-12
alkyl group, and R
3
represents a C
1-2
alkyl group.
Reaction [II]
In the general formula (8), R
1
and R
2
may be the same or different and each represent a C
4-12
alkyl group, and k represents an integer of from 0 to 4.
In the general formula (9), R
3
represents a C
1-2
alkyl group, and Z represents a chlorine atom, bromine atom, iodine atom or a group represented by any one of the following general formulae (10) and (11):
wherein R
6
represents a C
1-2
alkyl group; and
wherein R
7
and R
8
each represent a hydrogen atom, C
1-2
alkyl group or carboxyl group.
Reaction [III]:
In the general formula (12) R
1
represents a C
4-12
alkyl group, R
3
represents a C
1-2
alkyl group, and k represents an integer of from 0 to 4.
In the general formula (13), R
2
represents a C
4-12
alkyl group; and J represents a chlorine atom, bromine atom, iodine atom or a group represented by the general formula (11).
DETAILED DESCRIPTION OF THE INVENTION
A. Novel Compound
The present invention relates to a novel quaternary ammonium salt represented by the following general formula (1):
wherein R
1
and R
2
each represent a C
4-12
alkyl group and may be the same or different; R
3
represents a C
1-2
alkyl group; k represents an integer of from 0 to 4; X represents an inorganic or organic anion group; n represents the valence of the anion group X which is selected from 1 and 2; and m represents an integer of 2 when n is 1 or 1 when n is 2.
In the general formula (1), the alkyl group represented by R
1
or R
2
there may be used an alkyl group having from 4 to 12 carbon atoms. In order to balance between antimicrobial properties and safety to human, the number of carbon atoms in the alkyl group is preferably from 5 to 10, more preferably from 6 to 8. R
3
may be either methyl or ethyl but is preferably methyl to exhibit higher antimicrobial properties.
In the general formula (1), X represents an inorganic or organic anion group. Preferred examples of such an inorganic or organic anion group include iodine ion, bromine ion, chlorine ion, fluorine ion, iodic acid ion, bromic acid ion, chloric acid ion, periodic acid ion, perchloric acid ion, chlorous acid ion, hypochlorous acid ion, nitric acid ion, nitrous acid ion, sulfuric acid ion, hydroxyl group ion or an anion group represented by any one of the following general formulae (2) to (5).
The number (m) of anion groups X connected to the compound of the general formula (1) is such that the product of n and m is 2 wherein n is the valence of the anion group X. For example, when the valence of the anion group X is −2, m is 1. When the valence of the anion group X is −1, m is 2.
[R
4
COO
⊖
] (2)
wherein R
4
represents a C
1-7
alkyl or alkenyl group which may have one or more hydroxyl group or carbonyl group;
[
⊖
OCO—R
5
—COO
⊖
] (3)
wherein R
5
does not exist (the two groups COO are directly bonded to each other) or represents a C
1-8
alkyl or alkenyl group which may have one or more hydroxyl group;
[R
6
SO
4
⊖
] (4)
wherein R
6
represents a C
1-2
alkyl group; and
wherein R
7
and R
8
each represent a hydrogen atom, C
1-12
alkyl group or carboxyl group.
B. Process for the Preparation of Novel Compound
The quaternary ammonium salt represented by the general formula (1) can be prepared by any one of the following processes.
B-1. First-class Preparation Process
The first embodiment of the process for the preparation of the quaternary ammonium salt represented by the general formula (1) involves the reaction of a halogen compound represented by the following general formula (6) with a tertiary amine represented by the following general formula (7):
wherein k represents an integer of from 0 to 4; and Y represents a chlorine atom, chlorine atom or iodine atom; and
wherein R
1
and R
2
each represent a C
4-12
alkyl group; and R
3
represents a C
1-2
alkyl group.
Examples of the compound represented by the general formula (6) include halogen compounds such as &agr;, &agr;′-dichloro-o-xylene, &agr;, &agr;′-dichloro-m-xylene, &agr;, &agr;′-dichloro-p-xylene, &agr;, &agr;′-dibromo-o-xylene, &agr;, &agr;′-diodo-m-xylene, 3,6-bis(chloromethyl)durene, 2,4-bis(chlorometh)-dimethylbenzene and 2,5-bis(chloromethyl)toluene.
Examples of the compound represented by the general formula (7) include tertiary amines such as N,N-dipentyl-N-methylamine, N,N-dihexyl-N-methylamine, N,N-diheptyl-N-methylamine, N-butyl-N-hexyl-N-methylamine, N-pentyl-N-hexyl-N-methylamine, N-hexyl-N-octyl-N-methylamine, N,N-dipentyl-N-ethylamine, N,N-dihexyl-N-ethylamine and N-pentyl-N-hexyl-N-ethylamine.
These reactions can be effected at a temperature of from 50° C. to 120° C. in a proper organic solvent. The proportion of the tertiary amine of the general formula (7) to the halogen compound of the general formula (6) may be not less than 2 mols, e.g., from 2.0 to 2.3 mols per mol of the compound of the general formula (6).
As a reaction solvent there may be used an alcohol such as methanol, ethanol and n-propanol, mixture of water and alcohol or aromatic organic solvent such as benzene, toluene and xylene. The reaction temperature may be not lower than 80° C. At
Harada Katsuyoshi
Kourai Hiroki
Kume Masayoshi
Shibata Shigeyuki
Boyer Charles
Toagosei Co. Ltd.
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