JP3024020B2 - Disinfectant composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a germicidal disinfectant composition, and more particularly to a germicidal disinfectant composition used for fingers, body skin, face, hair or body hair of livestock and animals, body skin, clothing, tableware and the like. About.

[0002]

2. Description of the Prior Art Conventionally, a disinfecting and disinfecting detergent composition for fingers, face, body skin and hair has been used as an anionic surfactant and a nonionic surfactant as main components for washing. An activator and a mixture thereof are used, and triclosan, trichlorocarbanite, and the like are blended as the main components of the disinfecting and disinfecting detergent composition. However, germicidal disinfectant components such as liclosan and trichlorocarbanite lack a rapid effect on bacteria, and due to this factor, they cannot exert sufficient bactericidal activity within the washing time.

[0003] On the other hand, quaternary ammonium salts have excellent bactericidal activity against bacteria, and also have excellent fast-acting efficacy, and have been used in a wide range of fields such as medical care, quasi-drugs, cosmetics, environment, food factories, and wood corrosion. Used. However, when mixed with an anionic surfactant such as, for example, alkyl sulfate, the quaternary ammonium salt is feared for its bactericidal activity,
I couldn't demonstrate enough power. From these facts, there is a demand for a germicidal disinfectant that makes use of the bactericidal activity of the quaternary ammonium salt, has a high fast-acting effect on bacteria, and exhibits a sufficient effect even within the washing time.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to provide a sterilizing / disinfecting composition which exhibits a bactericidal activity quickly and has an excellent detergency.
When a quaternary ammonium salt is used, and a phosphate ester-based anionic surfactant and an alkyl glucoside that is a nonionic surfactant are blended, the bactericidal activity of the quaternary ammonium salt is sufficiently exhibited, Furthermore, they have found that they exert a quick effect even within the washing time, and have completed the present invention.

That is, the present invention is represented by the general formula (I)
It contains (a) a quaternary ammonium salt, (b) a phosphate ester-based anionic surfactant and (c) an alkyl glucoside represented by the general formula (II) as a washing component, and is particularly suitable for disinfecting skin and hair. And a disinfectant composition.

[0006]

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(Wherein at least one of R ₁ , R ₂ , and R ₃ is a linear or branched alkyl or alkenyl group having 8 to 30 carbon atoms, and the rest is a methyl group, an ethyl group, a benzyl group,

[0008]

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Halogen, phosphate ester, phosphonic acid,
It is a sulfonic acid or a sulfuric acid ester having 7 or more carbon atoms or an anionic oligomer or copolymer having a degree of polymerization of 3 or more. )

[0010]

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Wherein R ₅ represents a linear or branched alkyl or alkenyl group having 1 to 30 carbon atoms, n represents an integer of 1 to 15, m represents an integer of 0 to 20, Has 2 to 4 carbon atoms
Represents an alkylene oxide. ).

Hereinafter, the configuration of the present invention will be described in detail.

Specific examples of the cation moiety of the quaternary ammonium salt represented by the general formula (I) include, for example, monoalkyltrimethylammonium, monoalkenyltrimethylammonium, dialkyldimethylammonium, dialkenyldimethylammonium and monopolyoxyalkylene. Alkyltrimethylammonium,
Monopolyoxyalkylenealkenyltrimethylammonium, monoalkylbenzyldimethylammonium,
Monoalkenylbenzyldimethylammonium and the like. At least one of R ₁ , R ₂ and R ₃ has 8 to ₃ carbon atoms.
0, preferably 8 to 20 linear or branched alkyl or alkenyl groups.

The counter ion portion of the quaternary ammonium salt represented by the general formula (I) includes, for example, Cl, Br and I in the case of halogen. Esters, monoalkenyl phosphoric acid, dialkyl phosphoric acid, dialkenyl phosphoric acid, polyoxyalkylene alkyl ether phosphoric acid, sugar phosphate ester, glycerin phosphoric acid, sulfate ester, etc., and the alkyl group or alkenyl group of the phosphate ester. The carbon number is 7-30, preferably 8-20. Further examples of the phosphoric acid ester include polyoxyalkylene alkyl or alkenyl ether phosphoric acid, and the number of moles of ethylene oxide, propylene oxide, etc. added is 60 or less, preferably 20 or less.
It is as follows. Among them, sugar phosphates include glucose-phosphate, glucoseamine phosphate, maltose-1-phosphate, sucrose phosphate, and the like, and are not limited to these sugars. Examples of glycerin phosphate include phospholipids such as phosphatidic acid. Further, as the sulfate, those having a total carbon number of 7 or more are used. Specific examples include lauryl sulfate, myristyl sulfate, palmityl sulfate, stearyl sulfate, oleyl sulfate, linole sulfate, cetyl sulfate, higher alcohol / ether sulfate, resin acid alcohol sulfate, and the like. As the sulfonic acid, one having a total carbon number of 7 or more is used. For example, alkyl benzene sulfonic acid, higher alkyl sulfonic acid, sulfonic acid of higher fatty acid ester, sulfonic acid of higher alcohol ether, alkyl naphthalene sulfonic acid, sulfosuccinate, alkyl phenol sulfonic acid, alkyl sulfonic acid of higher fatty acid amide, alkyl allyl ester sulfonic acid , Alkyl diphenyl ether sulfonic acid, alkyl benzimidazole sulfonic acid, and the like.

Further, as the anionic oligomer and the anionic copolymer, those having a degree of polymerization of 3 or more containing one or more selected from the following (1) and (2) are preferable. (1) Polymer having styrene sulfonic acid as an essential constituent monomer (2) Formalin condensate of sulfonated polycyclic aromatic compound which may have a hydrocarbon group as a substituent The above compounds (1) and ( A specific example of 2) will be described below. (1) Water-soluble or water-dispersible polymer containing styrene sulfonic acid as an essential constituent monomer Styrene sulfonic acid homopolymer is easily produced by polymerizing styrene sulfonic acid or sulfonating polystyrene. be able to. The polymer of styrene sulfonic acid has a skeleton represented by the following formula.

[0016]

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The molecular weight is at least 1,000, preferably from 1,000 to 500,000. Also, the copolymer of styrene sulfonic acid and other monomer is obtained by copolymerizing styrene sulfonic acid and other monomer or sulfonating the copolymer of styrene and other monomer. It can be easily manufactured. Copolymerization partners include hydrophobic monomers such as alkyl acrylate, alkyl methacrylate, vinyl alkyl ether, vinyl acetate, ethylene, propylene, butylene, butadiene, diisobutylene, vinyl chloride, vinylidene chloride, acrylonitrile, and styrene. And acrylic acid, methacrylic acid, maleic acid, fumaric acid, maleic anhydride, vinyl alcohol, acrylamide, methacrylamide, diacetone acrylamide, N-vinylpyrrolidone, 2-acrylamide-2-methylpropanesulfonic acid, methacrylsulfonic acid , Xylene sulfonic acid,
A hydrophilic monomer such as naphthalenesulfonic acid is used. Preferred copolymers include (meth) acrylic acid-
Styrene sulfonic acid copolymer may be mentioned. The molar ratio of (meth) acrylic acid styrene sulfonic acid in the copolymer is 1
/ 10 to 10/1, preferably 1/3 to 4/1. The average molecular weight is 1,000 to 100,000, preferably 1,000 to 500,000. Also, sodium salt, potassium salt, ammonium salt, diethanolamine salt, triethanolamine salt, monoisopropanolamine salt, diisopropanolamine salt, triisopropanolamine salt, 2-amino-2-methylpropane-1 to the extent that performance is not impaired. , 3 −
There may be a neutralized portion of a salt such as a diol salt. (2) a formalin condensate of a sulfonated polycyclic aromatic compound that may have a hydrocarbon group as a substituent.Specifically, a petroleum sulfonic acid derivative, a lignin sulfonic acid derivative, a naphthalene sulfonic acid derivative, a xylene sulfonic acid derivative, It is a formalin condensate such as an alkylbenzenesulfonic acid derivative. The compound (2) which is a counter ion of the compound represented by the general formula (I) according to the present invention includes, for example, naphthalene, alkyl-substituted benzene, alkyl-substituted naphthalene, anthracene, alkyl-substituted anthracene,
It can be obtained by sulfonating lignin, those having an aromatic ring in a petroleum residue, etc. by a general method, followed by formalin condensation. In this case, the degree of condensation is preferably 3 or more, more preferably 3 to 30. here,
When the degree of condensation is 2 or less, the effect of the condensation is small, causing a practical problem. As the aromatic compound to be used, various compounds can be used.Preferably, lignin, xylene, toluene, naphthalene, or an alkylnaphthalene having 1 to 6 carbon atoms may be used. Good. Further, amine ammonium salts and the like may be used as well as alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and the like to such an extent that the performance is not hindered.

Next, the phosphate ester-based anionic surfactant used in the present invention will be described. In the present invention, a generally known phosphate ester salt-based anionic surfactant is used. Specifically, the following general formula (I
II)

[0019]

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(Wherein R ₆ and R ₇ are the same or different and at least one is a straight-chain or branched-chain alkyl group, alkenyl group, polyoxyalkylene alkyl ether, sugar alcohol residue, sugar residue Group, a glycerin derivative, the rest being H 2 and alkali metals, alkylammonium, hydroxy-substituted alkylammonium.
Y represents H, an alkali metal, an alkyl ammonium, or a hydroxy-substituted alkyl ammonium. A phosphoric acid ester-based anionic surfactant composed of the compound represented by the formula (1) is used. In the general formula (III), at least one of R ₅ and R ₆ is a linear or branched alkyl group, alkenyl group, polyoxyalkylene alkyl or alkenyl ether group, sugar alcohol residue, sugar residue, glycerin derivative Etc., which may be the same or different. The carbon number of the alkyl group or alkenyl group is from 8 to 30, preferably from 8 to
20. The polyoxyalkylene alkyl or alkenyl ether has an addition mole number of ethylene oxide, propylene oxide, etc. of 1 to 60, preferably 3 to 30, and the alkyl group and alkenyl group have 1 carbon atom.
~ 30, preferably 8 ~ 20. Examples of the sugar residue include glucose, glucoseamine, maltose, sucrose and the like. One of R _{5 and} R ₆ is substituted with hydrogen or an alkali metal such as Na or K, an alkylammonium such as tetramethylammonium or tetraethylammonium, or a hydroxy-substituted alkylammonium such as tri (hydroxyethyl) amine. No problem. Y 1 includes hydrogen or an alkali metal such as Na or K, an alkylammonium such as tetramethylammonium or tetraethylammonium, or a hydroxy-substituted alkylammonium such as tri (hydroxyethyl) amine.

The phosphate ester-based anionic surfactant used in the present invention can be used alone or in combination of two or more, and is not limited thereto.

The alkyl glucoside represented by the general formula (II) used in the present invention is a nonionic surfactant, and R ₇ in the general formula (II) has 1 to 30 carbon atoms, preferably It is a linear or branched alkyl or alkenyl group having 8 to 20 carbon atoms. Further, n is an integer of 1 to 15 and is derived from glucose or an oligosaccharide having glucose as a unit. In the case of an oligosaccharide, the bond between glucose may be α or β or a mixture thereof. AO is an alkylene oxide having 2 to 4 carbon atoms, and is preferably ethylene oxide or propylene oxide alone or as a mixture. The average number of added moles m is 0-20.

In the present invention, the total amount of the quaternary ammonium salt represented by the general formula (I), the phosphate ester-based anionic surfactant and the alkyl glucoside represented by the general formula (II) is as follows: It is 2 to 50% by weight, preferably 5 to 30% by weight in the product. The balance of the composition of the present invention is optional components and water. The weight ratio of (a) a quaternary ammonium salt represented by the general formula (I) / (b) a phosphate ester-based anionic surfactant / (c) an alkyl glucoside represented by the general formula (II) Is (a) / (b) / (c)
= 1/1 to 100/1 to 100, preferably 1
/ 2 to 50/2 to 50. If the weight ratio is out of the above range, sufficient bactericidal activity of the quaternary ammonium salt cannot be obtained, or the stability of the preparation tends to decrease.

In the quaternary ammonium compound represented by the general formula (I), when the counter anion X ^- is a phosphate ester, and in the phosphate ester compound represented by the general formula (III), Y is an alkyl ammonium compound. Identical compound (ammonium phosphate)
In some cases, a better effect can be obtained. In this case, the mixing ratio with the compound represented by the general formula (II) is [weight of [total amount of ammonium phosphate salt: total amount of (I) + (III)] / (II) = 0.10-
99.1 / 99.1 to 0.1, preferably 70 to 95/30 to 5.

The composition containing a quaternary ammonium salt represented by the general formula (I), a phosphate ester salt anionic surfactant and an alkyl glucoside represented by the general formula (II) used in the present invention can be used for the skin. And can be used as a disinfectant cleaning agent for hair, for example, hand cleaning agents,
It can be used for body shampoos, shampoos for hair, facial cleansers, scrub cleaners, makeup cleaners for cosmetics and the like, and further can be used for animal skin and body hair cleaners. JP-A-1-168613 discloses a detergent composition containing a phosphate ester-based anionic surfactant and an alkyl glucoside which is a kind of nonionic surfactant. However, this detergent composition relates to a detergent for the purpose of improving foam quality and reducing skin irritation, and the present invention mainly aims at maintaining the bactericidal activity of quaternary ammonium salts and at the same time as having a rapid effect. And a germicidal disinfectant composition.

In using the germicidal disinfectant composition of the present invention, salts, phosphate ester salt anionic surfactants used in the present invention and salts within the range that do not impair the effects of the present invention, if necessary, are included in the preparation. A surfactant other than the alkyl glucoside, a water-soluble thickener, and the like may be used in combination. Examples of the salts include succinic acid, malonic acid, citric acid, gluconic acid, carboxylic acid metal salts such as glutaric acid, tripolyphosphoric acid, hexametaphosphoric acid, phosphoric acid compound metal salts such as phosphoric acid, Na ₂ SO ₄ , MgSO _{4 and the} like. Inorganic salts and the like. These can be used alone or in combination. Examples of the surfactant include a nonionic surfactant other than the alkylglucoside represented by the general formula (II), an anionic surfactant other than the phosphate ester-based anionic surfactant, and an amphoteric surfactant. Nonionic surfactants other than the nonionic surfactants according to the present invention include, for example, polyoxyethylene (hereinafter referred to as POE) alkyl (C6 to C22) ether, POE alkyl (C0 4-18) Nonionic surfactants such as phenol ether, polyoxypropylene polyoxyethylene (block or random) alkyl ether, POE phenyl phenol ether, POE styrenated phenol ether, and POE tribenzyl phenol ether. Examples of anionic surfactants other than the phosphate ester-based anionic surfactant according to the present invention include lignin sulfonate, alkylbenzene sulfonate, alkyl sulfonate, POE alkyl sulfonate, POE alkylphenyl ether sulfonate Anionic surfactants such as salts, POE phenyl phenol ether sulfonate, naphthalene sulfonate, and naphthalene sulfonic acid formalin condensate are exemplified. These can be used alone or in combination. Its content in the fungicide is 0 to 20% by weight, preferably 1 to 10% by weight.
Examples of the amphoteric surfactant include alkylaminotrimethylglycine, alkyldimethylamine oxide, and alkyldiaminoethylglycine hydrochloride. As the water-soluble thickener, any of natural, semi-synthetic and synthetic water-soluble thickeners can be used.For natural mucilage, microorganism-derived xanthan gum, xanflow, plant-derived pectin, gum arabic, guar gum, and the like, Methylated, carboxyalkylated, hydroxyalkylated (including methylcellulose, carboxymethylcellulose, hydroxymethylcellulose, etc.), sorbitol, etc. of cellulose or starch derivatives for semi-synthetic mucilage, and polyacrylate, polymaleate for synthetic mucilage , Polyvinylpyrrolidone, pentaerythritol ethylene oxide adduct and the like. The water-soluble thickener is present in the germicidal disinfectant composition in an amount of about 0-3.0% by weight, preferably about 0.
It is blended in an amount of 05 to 0.5% by weight.

[0027]

The germicidal disinfectant composition of the present invention does not impair the excellent bactericidal activity of the quaternary ammonium salt, has a sufficient bactericidal effect within the washing time, and has a sufficient detergency. That is, according to the present invention, a germicidal disinfectant composition that satisfies both bactericidal power and detergency, which was not satisfied by the conventional germicidal disinfectant, can be obtained.

[0028]

Next, the present invention will be described specifically with reference to examples, but the present invention is not limited to these examples. In the examples, "%" means% by weight.

The compound No. 1 of the present invention used in the examples
No. 7 and No. 7 and Comparative Example Compounds No. 1 and No. 2, formulation examples using these compounds, and comparative formulation examples are shown below.

<Compound of the Present Invention>

[0031]

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[0032]

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<Comparative compound>

[0034]

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Further, the following compounds were used as the phosphate ester salt-based anionic surfactant (phosphate ester) and the alkylglucoside represented by the general formula (II).

[0036]

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[0037]

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<Formulation Example> Formulation Example 1; Compound 1 of the present invention 1.0% Phosphate ester 20.0% Alkyl glucoside 10.0% Formulation Example 2; Compound 2 of the present invention 1.0% Phosphate ester 20.0% Alkyl glucoside 10.0% Formulation Example 3; Inventive compound 3 1.0% Phosphate ester 20.0% Alkyl glucoside 10.0% Formulation example 4; Present compound 4 1.0% Phosphate ester 17.0% Phosphate ester 3.0% Alkyl glucoside 10.0% Formulation example 5; Inventive compound 5 1.0% phosphoric acid Ester 17.0% Phosphate ester 3.0% Alkyl glucoside 10.0% Formulation Example 6; Compound 6 of the present invention 1.0% Phosphate ester 17.0% Phosphate ester 3.0% Alkyl glucoside 10.0% Formulation Example 7; Compound 7 of the present invention 1.0% Phosphate ester 20.0 % Alkyl glucoside 10.0% <Comparative Formulation Example> Comparative Formulation Example 1; Comparative Compound 1 1.0% Phosphate 20.0% Alky Glucoside 10.0% Comparative Formulation Example 2; Comparative Compound 2 1.0% Phosphate ester 17.0% Phosphate ester 3.0% Alkyl glucoside 10.0% Comparative Formulation Example 3; Compound of the present invention 1 1.0% Phosphate ester 20.0% Comparative Formulation Example 4; Compound 2 2.0% CH ₃ (CH ₂ ) ₁₁ -OSO ₃ -Na 19.0% Comparative Formulation Example 5; Phosphate ester 20.0% Alkyl glucoside 10.0% Comparative Formulation Example 6; Phosphate ester 20.0% In each of the above formula examples The rest is water.

Example 1 The samples of Formulation Examples 1 to 7 and Comparative Formulation Examples 1 to 6 were adjusted as quaternary ammonium salts to various concentrations shown in Tables 1 and 2, and then cultured in a liquid medium in advance. Escherichia coli (Esc
herichia coli), Staphylococcus aure
us) and Candidaalbicans for 5 minutes at room temperature. Thereafter, the cells were collected, planted in a new medium, and allowed to stand for a certain period of time. The production state of these cells was evaluated according to the following criteria.
The results are shown in Tables 1 and 2. <Evaluation>-Does not grow (no colony formed) ± Slightly grows (less than 5 colonies) + Shows growth (5 or more colonies)

[0040]

[Table 1]

[0041]

[Table 2]

Example 2 Hand sterilization and washing test using the preparations prepared in accordance with the above-mentioned 1, 2, 6 and the following prescription examples 7, comparative prescription examples 6 and the following comparative prescription examples 7 and 8 made. <Formulation Example> Formulation Example 7: Compound of the present invention 4 1.0% Phosphate ester 17.0% Phosphate ester 3.0% Alkyl glucoside 10.0% Here, alkyl glucoside is a compound having the following structure.

[0043]

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<Comparative Formulation Example> Comparative Formulation Example 7; Comparative compound 2 1.0% Phosphate ester 20.0% Alkyl glucoside 10.0% Here, the phosphate ester is a compound having the following structure.

[0045]

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Comparative Formulation Example 8 Phosphate
20.0% Alkyl glucoside 10.0% 5 ml of the above-prepared preparation was placed on the palm of the hand, rubbed for 1 minute, and then washed with sterile running water for 30 seconds. After washing with water, the water was gently removed, and the palm of the hand was gently pressed onto the SPCLD medium, followed by culturing at 28 ° C. for 48 hours. The number of colonies generated after the culturing was counted to determine the number of surviving bacteria. Table 3 shows the results.

[0047]

[Table 3]

Example 3 The preparations prepared according to Formulation Examples 1, 2, 6 and 7 used in Example 2 and Comparative Formulation Examples 6 to 8 were used as shampoo compositions, the hair was washed, and a sterilization washing test was performed. . 10 ml of each formulation was applied to the hair which had been sufficiently moistened with sterile water, washed and sterilized for 2 minutes, and then washed with sterile running water for 30 seconds. After rinsing with water and gently draining the water, immerse the head in 1 liter of sterilized water, massage and extract the bacteria extracted in 1 liter of sterilized water.
The cells were inoculated into SPLCD medium and cultured at 28 ° C for 48 hours. The number of colonies generated after the cultivation was counted to determine the number of surviving bacteria. Table 4 shows the results.

[0049]

[Table 4]

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁷ Identification code FI A61K 31/66 A61K 31/66 31/70 31/70 31/715 31/715 (56) References JP-A-2-218605 ( JP, A) JP-A-2-97592 (JP, A) JP-A-1-168613 (JP, A) JP-A-1-144497 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , (DB name) A01N 33/12 101 A61K 7/02 A61K 7/075 A61K 7/50 A61K 31/14 A61K 31/66 A61K 31/70 A61K 31/715

Claims (2)

(57) [Claims] (1) a quaternary ammonium salt represented by the general formula (I); (b) a phosphate ester-based anionic surfactant; and (c) a compound represented by the general formula (II). Disinfectant composition. Embedded image (In the formula, at least one of R ₁ , R ₂ , and R ₃ is a linear or branched alkyl or alkenyl group having 8 to 30 carbon atoms, and the rest is a methyl group, an ethyl group, a benzyl group, It is a halogen, a phosphoric acid ester, a phosphonic acid, a sulfonic acid or a sulfuric acid ester having 7 or more carbon atoms, or an anionic oligomer or copolymer having a degree of polymerization of 3 or more. ) (Wherein R ₅ represents a linear or branched alkyl or alkenyl group having 1 to 30 carbon atoms, n represents an integer of 1 to 15, m
Represents an integer of 0 to 20, and AO represents an alkylene oxide having 2 to 4 carbon atoms. ) 2. The weight ratio of (a) a quaternary ammonium salt represented by the general formula (I), (b) a phosphate ester-based anionic surfactant and (c) a compound represented by the general formula (II). The disinfectant composition according to claim 1, wherein (a) / (b) / (c) = 1/1 to 100/1 to 100.