An antimicrobial caries-detecting composition, which comprises(i) water, a water-miscible solvent or a combination thereof, (ii) a dye capable of staining the caries-infected portions of teeth, and (iii) at least one antimicrobial agent.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The present invention relates to an antimicrobial caries detecting 
composition for use in the odontological treatment of caries-infected 
teeth, which composition selectively stains the portion of a tooth which 
is infected with carcinogenic microbes, prior to removal of the infected 
dentin of the tooth, thereby facilitating the removal of the infected 
portion of the tooth. More particularly, the present invention relates to 
a composition which is capable of sterilizing and staining the infected 
portions of teeth at the same time. 
2. Description of the Background 
In the conventional treatment of tooth caries which removes the dentin 
infected with cariogenic microbes, the infected portion is selectively 
stained so as to clearly differentiate the infection from the non-infected 
portions, thereby removing the infected dentin as completely as possible. 
In order to achieve this objective, Japanese Patent Application (JPA) 
Kokai No. Sho-51-38428 discloses a "caries-detecting composition" which 
comprises a basic fuchsine and a mono- or polyalcohol, and shows some 
effectiveness. However, even with the development of such a 
cartes-detecting composition and its wide-spread commercial use, there is 
still no end to the reports of pulp irritation after caries treatment, 
which is a serious problem in the field of dentistry. 
On the other hand, in order to prevent caries, JPA Kokai No. Sho-51-38427 
discloses as its objective, a "dental plaque or calculus-detecting 
composition", which is used to stain the dental plaque or the like which 
adheres to the tooth surface thereby causing caries. JPA Kokai No. 
Sho-56-96700 discloses a "caries activity-indicating composition", which 
is used with sufficient daily teeth brushing and thereby provides an 
evaluation of the degree of danger of dental plaque. The former 
composition comprises a dye which is dissolved in a polyalcohol and/or 
water, while the latter composition comprises a pH indicator which is 
dissolved in an aqueous solution of a water-soluble polymer to which is 
added an antibiotic or preservative selected from chloraphenicol compounds 
and sodium azide compounds. 
The cause of the dental pulp irritation, which has been discussed in those 
proposals, most probably is attributable to the penetration of the 
restorative component into the dental pulp. Various studies have been made 
on this penetration. However, it has been found that even if the 
restorative component itself is embedded adjacent to dental pulp, no 
serious irritation results. In this regard it has been recently proposed, 
as a component of the theory of bacterial cariogenesis, that the secondary 
invasion of oral bacteria into a cavity and the failure to remove the 
carcinogenic microbe-infected portion of a tooth, causes dental pulp 
irritation. In fact, recent studies into the prevention of secondary 
invasions of oral bacteria into cavities have been directed to increasing 
the adhesiveness between the dental pulp and the restorative material 
applied thereto in order to improve the sealing the margin of the 
restorative material. As a result, recent advances have achieved a very 
high level of adhesion between the dentin and the restorative material. 
Accordingly, cases of dental pulp irritation have decreased in recent 
days. However, it can not be said that there have been no reports of 
dental pulp irritation after caries treatment. 
The cause of dental pulp irritation which appears to remain is the failure 
to remove all of the caries-infected dentin and the contamination of 
cleaned cavity with caries-infected tissue pieces that have just been 
removed from the cavity before the application of a restorative material 
thereto. 
In the work leading to the present invention, the present inventors have 
assiduously studied various materials which would enable the complete 
removal of the carcinogenic microbes-infected portions from teeth and/or 
elimination of the contamination by the once-removed infected dentin from 
the cleaned cavity. The following has been found. 
(1) A caries-detecting composition can not completely penetrate into the 
deepest portion of the caries-infected portion of teeth by one 
application, if the infected portion is thick. Therefore, a dentist 
repeatedly applies the caries-detecting composition to the affected area 
of a tooth to confirm the infected part, and then bores a cavity in the 
affected part. However, if the dentist has failed to finally stain the 
infected portion in the last test for infected matter, it is probable that 
carcinogenic microbes have not been completely removed. 
(2) At the point at which the removal of the infected dentin is almost 
finished, it is often difficult to determine whether or not the dentin had 
been stained, so that removal of the infected dentin is often incomplete. 
In the case the cavity bottom is too thin, the cutting tool used would 
often penetrate the dental pulp. In order to prevent this problem, the 
operating dentist would often stop the removal of the seemingly slightly 
stained part. 
(3) A so-called smear layer comprising powdered dentin is inevitably formed 
on the surface of the dentin from which the infected portion has been 
removed. It is likely that bacteria will remain in the smear layer. 
(4) Since dentinal tubules are found in the surface of the dentin which has 
been drilled for the removal of the infected portion of the tooth, the 
smear layer is pressed into the dentinal tubules thereby forming a plug. 
It is said that the smear plug remaining in the opening of the dentinal 
tubules has an important role in protecting dental pulp from the 
components of restorative materials. It is likely, however, that the plug 
may be infected with carcinogenic microbes. 
(5) Another possible source of contamination is the highly-contaminated 
dentin pieces which are scattered around the infected tooth during removal 
of the infected portion. This material is mixed with body fluids such as 
saliva, and likely again contaminates the affected portion. No attempts 
have been made to solve the possible problem of item (5). 
The failure to remove any infected dentin must be solved. However, even if 
the infected dentin can not be completely removed or even if the infected 
dentin contaminates the affected portion, such should not cause 
cariogenesis if the bacteria existing in the infected dentin are 
inactivated. In order to achieve inactivation, if the cavity formed in an 
infected tooth is treated with a microbiocidal solution which is effective 
against cariogenic microbes, the object of the invention can be attained. 
Some trial reports have been introduced at various meetings of dental 
societies and in various odontological journals. However, even if carious 
cavities are treated with a microbicidal solution, the question of whether 
or not the microbiocidal solution penetrates throughout the entire region 
of the infected dentin depends on the thickness of the infected dentin. 
The pulp cavity has its own inner pressure, and the inner fluid in 
dentinal tubules flows from the pulp to the surface of the tooth. 
Therefore, even if a microbiocide is applied to the surface of the 
infected dentin, it is in fact difficult for the microbiocide to 
effectively penetrate into the inner depth of the infected dentin. 
Accordingly, if the infected dentin is thick, it is likely that the 
microbiocide applied thereto is often ineffective. After having made 
repeated studies to solve the above-mentioned problems, the present 
inventors have reached the following conclusions: 
(1) When a caries-detecting composition is used to stain infected dentin 
while simultaneously sterilizing the dentin, the powdered dentin formed 
during a subsequent step of removing the dentin is sterilized. Therefore, 
the danger of dental pulp irritation, because of contamination of the 
powdered dentin in the affected portion, is greatly reduced, and even the 
danger of contamination of the adjacent teeth and the gums is reduced. 
Further, the possibility of infection from the tools that may induce 
additional cariogenesis is also greatly reduced. 
(2) Where the infected dentin is removed and is simultaneously stained for 
caries detection and sterilization, the infected dentin is well-sterilized 
while its thickness is reduced. Here, even the bacteria existing in the 
depths of the affected portions can be effectively killed. In particular, 
after the last staining for the final confirmation, no infected dentin 
exists in the cavity. Even if some bacteria have readhered to the affected 
portions, they shall be completely free of bacteria. Under these 
conditions, therefore, satisfactory treatment is ensured. On the basis of 
these findings, the present inventors have made the following studies in 
order to find an antimicrobial caries-detecting composition. 
The microbiocide which is employed in the present invention may be any and 
every known type that has been used in detergents and microbicidal 
compositions for dental use. However, (1) preferred microbiocides are 
those which are capable of killing 99% or more of 10 thousands of bacteria 
per 1 cm.sup.3 with a solution having a microbicidal concentration of 1000 
.mu.g/ml for 10 seconds, wherein said bacteria include Mutans streptococci 
I and Lactobaclli, which are said to be cariogenic bacteria, Streptococcus 
mitis, and Actinomyces viscosus, which are said to be bacteria that may 
have cariogenicity, and strictly anaerobic bacterias which are said to 
cause dental pulp irritation. 
(2) The microbiocides must be soluble in water and/or water-miscible 
solvents. 
(3) When stored in the composition of the invention, the microbicides must 
be stable for a long period of time, and must not discolor the dye which 
is essential to the composition. 
Among conventional microbiocides, preferred are cationic microbiocides, 
biguanide-type microbiocides, halogenated diphenyl ethers and analogues 
thereof, as suitable microbiocides for the present invention. Of these 
compounds, more preferred is at least one compound selected from the group 
consisting of cetylpyridinium hydrochloride, chlorhexidine, trichlosan and 
irgasan, or a mixture of two or more of these compounds. 
More preferably, the caries-detecting composition of the invention still 
has some additional activity even in the stage of treatment after the 
removal of the caries-affected portion. Specifically, a polymerizable 
antimicrobial compound having both an antimicrobial group and a 
polymerizable group in the molecule does not interfere with the subsequent 
application of a dental adhesive to the surface of the tooth, even though 
it remains on the surface of the dentin, and, in addition, the 
antimicrobial compound copolymerizes with the adhesive to reinforce the 
adhesive layer during the restorative operation. Being different from 
other antimicrobial compounds that do not polymerize but remain as they 
are, the present polymerizable antimicrobial compound remains in the 
restorative material while being chemically bonded to the material after 
the dental treatment. Considering adhesion durability, therefore, the 
polymerizable antimicrobial compound is expected to exhibit remarkably 
safe effects. In addition, a compound of this type is further expected to 
modify the surface of the dentin so that it is more compatible with dental 
adhesives. The present inventors have found that, as an antimicrobial 
compound of this type, preferred are one or more polymerizable 
antimicrobial compounds having a (meth)acryloyl or styryl group and a 
quaternary ammonium salt group in the molecule, which are represented by 
formula 1 through formula 4. 
SUMMARY OF THE INVENTION 
Accordingly, one object of the present invention is to provide an 
antimicrobial caries-detecting composition. 
Briefly, this object and other objects of the present invention as 
hereinafter will become more readily apparent can be attained by an 
antimicrobial caries-detecting composition which comprises water and/or a 
water-miscible solvent, a dye capable of staining the caries-infected part 
of teeth, and at least one dentally effective antimicrobial agent.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS 
In one aspect of the antimicrobial, caries-detecting composition the 
antimicrobial agent is selected from the group consisting of cationic 
microbiocides, biguanide microbiocides and halogenated diphenyl ether 
microbiocides. 
In a second major aspect of the invention the antimicrobial agent is at 
least one polymerizable antimicrobial agent selected from the group 
consisting of compounds having a (meth)acryloyl or styryl group and a 
quaternary ammonium salt group in the molecule and is represented by the 
following formulas 1, 2, 3 and 4: 
EQU H.sub.2 C.dbd.C(R.sup.1)--C(O)--X--R.sup.2 --Y 
wherein 
R.sup.1 =H or CH.sub.3, 
R.sup.2 =alkylene group of C.sub.2 -C.sub.18 carbons, 
X=O, S, or NH, 
##STR1## 
wherein R.sup.3 =H or a C.sub.2 -C.sub.18 alkyl group; 
R.sup.4 =CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CH.sub.2 OH; 
Z=F, Cl, Br, or I; 
EQU (H.sub.2 C.dbd.C(R.sup.5)--C(O)--X--R.sup.6 --).sub.2 --Y' (2) 
wherein 
R.sup.5 =H or CH.sub.3, 
R.sup.6 =alkylene group of C.sub.2 -C.sub.12, 
X=O, S, or NH, 
##STR2## 
wherein R.sup.7 =H or alkyl group of C.sub.1 -C.sub.18 ; 
R.sup.8 =CH.sub.3, CH.sub.2 CH.sub.3, or CH.sub.2 CH.sub.2 OH; 
Z=F, Cl, Br, or I; 
EQU H.sub.2 C.dbd.C(R.sup.9)--C.sub.6 H.sub.4 --R.sup.10 --Y (3) 
wherein 
R.sup.9 =H or CH.sub.3, 
R.sup.10 =alkylene group of C.sub.2 -C.sub.12, 
Y=the same as Y in formula (1); 
##STR3## 
wherein R.sup.11 =H or CH.sub.3, 
R.sup.12 =alkylene group of C.sub.1 -C.sub.12, 
R.sup.13 =alkylene group of C.sub.1 -C.sub.12, 
R.sup.14 =alkyl group of C.sub.12 -C.sub.22, 
A=O, S, or NH, 
B.sup.1, B.sup.2 =the same or different groups selected from --CO--, 
CO.sub.2 --, --O--, --S--, --OCONH-- and --NHCO.sub.2 --, 
Z=F, Cl, Br, or I. 
Suitable examples of the microbicides which are useful in the antimicrobial 
caries-detecting composition of the invention include cationic 
microbiocides of various quaternary ammonium salts, of which is preferred 
is cetylpyridinium hydrochloride. Also preferred are biguanide 
microbiocides, of which more preferred are various salts of chlorhexidine. 
Other preferred microbiocides are halogenated diphenyl ethers and their 
analogue compounds, of which especially preferred are trichlosan, irgasan, 
hexachlorophene, anmd the like. Other suitable microbiocides of the 
invention include thymol, clove oil, homosulfamine, nitrofurazone, 
sulfonamide preparations, nitrofurazone derivatives, acridine-type dyes, 
formalin preparations, alexidine, cetapron, metafen, sulfonamide, and the 
like. Among those especially preferred are trichlosan, irgasan, 
chlorhexidine and cetylpyridinium hydrochloride. 
Suitable examples of the polymerizable antimicrobial agents for use in the 
invention include quaternary ammonium salts having a (meth)acryloyl group 
or a styryl group, as those of formula 1, and polymerizable antimicrobial 
compounds having a (meth)acryloyloxy group and a pyridinium salt group, as 
those of formula 2. The term, quaternary ammonium salt as referred to 
herein includes quaternary ammonium salts in the narrow sense and 
pyridinium salts. 
Especially preferred compounds are: methacryloyloxydodecylpyridinium 
bromide, methyacryloxyocadecylpridinium bromide 
methacryloyloxyhexadecylpyridinium bromide, 
methacryloyloxydodecylpyridinium chloride, 
methacrylolyloxyoctadecylpyridinium methaoxyloyloxyhexadecylpyridinium 
chloride, N,N-dimethacyloyloxyethyllaurylbenzylammonium bromide, 
N,N-dimethacyloyloethyllaurylbenzylammonium chloride, methacryloyloxyethyl 
[4-N-octadecylpyridinylmethyl] succinate bromide, 
methacryloyloxyethyl[4-N-octadecylpyridinylmethyl] succinate chloride, 
methacryloyloxyethyl [4-N-hexadecylpyridinylmehyl] succinate bromide, 
methacryloyloxyethyl[4-N-hexadecylpyridinylmethyl] succinate chloride, 
methacryloyloxyethyl[4-N-dodecylpyridinylmethyl] succinate bromide, 
methacryloyloxyethyl[4-N-dodecylpyridinylmethyl] succinate chloride, 
hexadecyl[4-3-(5-methacryloyloxy)valeroyloxy)propyl]pyridinium bromide, 
hexadecyl[4-(12-methacryloylamino)dodecanoyloxymethyl]pyridinium chloride, 
and the like. 
Other suitable compounds include 4-vinylbenzylmethyldodecylammonium 
chloride, 4-vinylbenzylmethylhexadecylammonium chloride, 
2-styrylethylmethyldodecylammonium chloride, 
2-styrylethylmethylhexadecylammonium chloride, and the like. 
However, antibiotics of some types such as sodium azide, phenol, cresol, 
hydrogen peroxide, iodoform, hypochlorous acid and the like, as 
microbiocides, are unsuitable for the composition of the invention, since 
they easily decompose in the composition or will decompose or denature the 
dye existing in the composition. Further, when they remain on the surface 
of the dentin, they will probably interfere with the subsequent 
polymerization of the radical polymerizable composition. 
The dye which is used in the antimicrobial caries-detecting composition of 
the invention must be soluble in the solvent(s), and is capable of 
visually indicating the portion of the tooth into which the composition 
has penetrated. In addition, the dye must not be removable from the 
portion of the tooth it penetrates, even when the portion is rinsed with 
water. Preferably, the color of the dye is clearly differentiated from 
that of the natural dentin, and is capable of forming a striking contrast 
between its color and the color of the natural dentin. Accordingly, 
preferred are deep color dyes such as red, blue, violet or black dyes. 
Examples of such dyes include basic fuchsine, eosine, erythrosine, acidic 
fuchsine, safranine, rose bengale, Phloxine BK, acid red, fast acid 
magenta, Phloxine B, Fast Green FCF, Rhodamine B, gentian violet, sodium 
copper chlorophyll, laccaic acid, cochineal, and shisonin. One or more of 
those dyes are usable in the invention. 
It is noted that Phloxine BK has the CI number 5410 and is also known as 
Acid Red 92. Phloxine B has the same designation. Fast Green FCF, has the 
CI number 42053 Rhodamine B has the CI number 45170. The CI number is the 
Color Index number. 
The dye concentration in the composition preferably ranges from 0.1-2% by 
weight, more preferably from 0.1-1% by weight. If it is less than the 
defined range, the dye does not satisfactorily stain the intended region. 
However, if it is greater than the defined range, the dye stains even the 
second decalcified layer and even further the healthy area, which 
obviously makes the determination of the infected area more difficult. 
The solvent for the composition of the invention must be so selected that 
not only does it dissolve the dye and the microbiocide in the composition, 
but also reduces the viscosity of the composition to facilitate the 
penetration of the composition into the infected dentin. Preferred 
solvents include those which are water-miscible solvents which are easily 
miscible with water in any ratio to give a uniform solution. Desirably, 
the water-miscible solvent compound has not more than 10 carbon atoms, has 
a polar group, and has a viscosity of not larger than 20 cps. Especially 
preferred are organic mono-, di- or tri-hydroxy compounds having from 2 to 
10 carbon atoms. These solvents enhance the penetration of the dye into 
the caries area to promote the clear coloration of the caries area. 
Suitable examples of solvent compounds include ethanol, ethylene glycol, 
n-propanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, 
1,2-butanediol, 1,3-butanediol, 1,4-butanediol, isobutyl alcohol, n-amyl 
alcohol, isoamyl alcohol, diethylene glycol, triethylene glycol, 
tetraethylene glycol, ethylene glycol monomethyl ether, ethylene glycol 
monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol 
monoacetate, diethylene glycol monoethyl ether, diethylene glycol 
monobutyl ether, diethylene glycol monoacetate, triethylene glycol 
monomethyl ether, triethylene glycol monoethyl ether, glycerin, and the 
like. Of these, preferred are propylene glycol and triethylene glycol, 
since they produce good results. 
Other organic solvents useful in the invention include tetrahydrofuran. 
dimethylformamide, dimethylsulfoxide, dioxane, acetone and 
dimethoxyethane. Phenol cannot be used in the invention, since it is too 
toxic. Organic amines, despite their good ability to fix dyes, are 
unsuitable for the invention, since they emit an offensive odor and they 
are harmful to the human body. Hydrocarbons are also unsuitable, since 
they poorly dissolve dyes and their ability to fix dyes is much inferior 
to the dye-fixing ability of water. 
As has been mentioned herein above the organic solvents may be used in 
combination with water, and one or more of them may be used in a mixture. 
The blending ratio of the solvents may be suitably determined, depending 
on the solvents which are blended. 
The composition of the invention can be prepared easily. For example, a 
predetermined amount of the dye and a predetermined amount of the 
microbiocide may be added to the organic solvent, distilled water or a 
mixture thereof, and the combined materials are stirred and dissolved at 
room temperature or under mild heating. Alternatively, an excessive amount 
of the dye and an excessive amount of the microbiocide are first dissolved 
in the organic solvent, distilled water or a mixture thereof, and then the 
organic solvent, distilled water or mixture thereof is added to the 
resulting solution to dilute it to a desired concentration just before its 
use. Depending on the combination of the microbiocide and the solvent, the 
microbiocide may be difficult to dissolve in the solvent. In such a case, 
any known conventional surfactant may be added to the mixture to give a 
uniform composition. 
To apply the antimicrobial caries-detecting composition of the invention to 
the cavity of the caries-infected tooth of a patient, the composition is 
placed in a container equipped with a thin long nozzle, and a small amount 
of the composition is dropped onto the cavity through the nozzle. One to 
10 seconds after this application, the cavity is rinsed with water. By 
this simple operation, just the first ring of decalcified layer is clearly 
stained with the composition, while the second decalcified layer and the 
non-infected dentin are hardly stained. As a result, the portion infected 
with cariogenic microbes can be accurately detected, while, at the same 
time, the bacteria existing in the infected area are killed or 
inactivated. 
By using the antimicrobial caries-detecting composition of the invention, 
caries-infected dentin can be removed from the teeth while preventing the 
cavity and the area around it from being contaminated with highly 
contaminated tissue pieces that may be scattered during the removal of the 
infected portion. Accordingly, the antimicrobial caries-detecting 
composition of the invention provides safer treatment of caries by not 
allowing failure to remove infected dentin and by not allowing 
re-contamination of the treated tooth with the removed infected dentin. 
Having now generally described the invention, a further understanding can 
be obtained by reference to certain specific examples which are provided 
herein for purpose of illustration only and are not intended to be 
limiting unless otherwise specified. 
Various types of dyes, antimicrobial agents and organic solvents usable of 
the Invention are mixed and stirred at room temperature to prepare various 
detecting compositions as shown in Table 1. These compositions were 
applied to the cross-section of caries infected teeth extracted from 
patients, and tested for their stain differentiability and 
microbiocidability. 
For stain differentiability, each sample was applied to the cross-section 
of the caries-infected tooth. About 5 seconds after application, the 
applied area was rinsed with water and observed as to whether the 
caries-infected portion could be clearly differentiated from the healthy 
dentin portion on the basis of the intrinsic color difference and the 
difference in hardness between the two parts. From these data, the samples 
were evaluated in accordance with the following criteria: 
++: The caries-infected portion was clearly stained. 
+: The caries-infected portion was stained. 
+-: The caries-infected portion was slightly stained. 
-: The caries-infected portion was hardly stained. 
For the microbiocidability, each sample was applied to the caries-infected 
portion of the tooth. Ten seconds after the application, the tooth was 
rinsed with water, and the stained portion and the portion deeper than the 
stained part were ground with a carbide bar attached to an air turbine. 
The resulting powdered teeth were placed in a germ-free BHI (brain heart 
infusion) broth medium, and the resulting material was treated with 
ultrasonic vibrations for 10 minutes, and incubated therein overnight. The 
growth of the cariogenic bacteria was observed by the light absorbance of 
the resulting culture. From the data thus obtained, the samples were 
evaluated in accordance with the following criteria: 
++: The growth of bacteria in the stained powdered teeth was inhibited, and 
no bacteria grew in the non-stained teeth. 
+-: The growth of bacteria in the stained powdered teeth was inhibited, but 
bacteria grew in the non-stained teeth. 
--: The growth of bacteria in the stained powdered teeth was not inhibited 
at all, and bacteria grew in the non-stained teeth. 
Table 1 
[Advantages of the Invention] 
Table 1 below shows that the antimicrobial caries-detecting composition of 
the invention is effectively useful in the dental treatment of caries for 
the removal of cariogenic microbes that may be left in the cavity of 
caries-infected teeth. Even if some cariogenic microbes are left in the 
cavity, the antimicrobial caries-detecting composition can completely kill 
the remaining microbes, thereby effectively inhibiting the dental pulp 
irritation and the secondary caries which are caused by the remaining 
microbes. 
TABLE 1 
__________________________________________________________________________ 
Microbicidal 
Agent Stain 
Dye (1%) Solvent (1%) Differentiability 
Microbicidability 
__________________________________________________________________________ 
Example 1 
Phloxine 
Propylene 
Trichlosan 
++ ++ 
BK Glycol 
Example 2 
Acid Red 
Propylene 
Trichlosan 
++ ++ 
Glycol 
Example 3 
Fast Acid 
Ethylene 
Trichlosan 
+ +- 
Magenta 
Glycol 
Example 4 
Phloxine B 
Ethylene 
Trichlosan 
+ +- 
Glycol 
Example 5 
Fast Green 
Propylene 
Chlorhexidine 
+ +- 
FCF Glycol * 
Example 6 
Rhodamine 
Propylene 
Chlorhexidine 
++ ++ 
B Glycol * 
Example 7 
Rhodamine 
Triethylene 
Chlorhexidine 
++ ++ 
B Glycol * 
Example 8 
Basic Ethanol/Water = 
Pyridinium 
++ ++ 
Fuchsine 
50/50 Salt ** 
Example 9 
Eosine 
1,3- Pyridinium 
++ ++ 
Hexanediol/ 
Salt ** 
Water = 
50/50 
Example 10 
Acidic 
Ethylene 
Pyridinium 
++ ++ 
Fuchsine 
Glycol Salt ** 
Example 11 
Basic Propylene 
Pyridinium 
++ ++ 
Fuchsine 
Glycol Salt ** 
Example 12 
Basic Propylene 
MDPB *** 
++ ++ 
Fuchsine 
Glycol 
Example 13 
Basic Propylene 
APSM-16 **** 
++ ++ 
Fuchsine 
Glycol 
Comparative 
Basic Aqueous None ++ -- 
Example 1 
Fuchsine 
Ethanol 
Comparative 
None Aqueous Irgasan 
-- ++ 
Example 2 Ethanol 
Comparative 
None Propylene 
Trichlosan 
-- ++ 
Example 3 Glycol 
__________________________________________________________________________ 
*: Chlorhexidine Acetate 
**: Cetylpyridinium Hydrochloride 
***: Methacryloyloxydodecylpyridinium bromide 
****: Methacryloyloxyethyl (4N-hexadecylpyridinylmethyl) succinate bromid 
The disclosures of priority Japanese Application Nos. 9-38681 and 9-45634 
filed Feb. 24, 1997 and Feb. 28, 1997 respectively are hereby incorporated 
by reference into the present application. 
Obviously, numerous modifications and variations of the present invention 
are possible in light of the above teachings. It is, therefore, to be 
understood that within the scope of the appended claims, the invention may 
be practiced otherwise than as specifically described herein.