KR101754644B1 - Antimicrobial Surfactant type preservative compounds and living chemical goods compositions comprising the same - Google Patents

Abstract

The present invention relates to a surfactant-type preservative compound and a biochemical product containing the same for the purpose of preventing spoilage and preserving physical properties in products containing water used for washing or smelling products, ≪ / RTI > The surfactant-type preservative compound of the present invention contains a surfactant compound having a hydrophobic group of an alkylamino or alkylamido structure as a preservative and a hydrophilic group of a dihydric alcohol group at a terminal thereof, thereby effectively controlling bacteria and fungi.

Description

TECHNICAL FIELD The present invention relates to a surfactant-type preservative compound exhibiting microbial control activity, and a biochemical composition containing the same,

The present invention relates to a preservative compound in the form of a surfactant and a biochemical product containing the same for the purpose of preventing water spoilage and preserving physical properties in products containing water used for washing or smelling products, ≪ / RTI >

All products containing water are essentially preservatives because microbes are easily propagated. Preservative is a medicine that prevents the decay of a material. It is a preservative to prevent the vegetable organic material from decaying due to the action of microorganisms, and the preservative is a preservative. In particular, detergent products containing a large amount of water essentially contain a preservative to prevent microbial decay in order to maintain quality for a long time. These products have a very long shelf life and are very likely to come into contact with microorganisms in their use and storage methods. Preservative components are essential in that various carbon sources and nitrogen sources are blended and the moisture content necessary for microbial growth is high .

Recently, there has been controversy about the human health of the preservative. However, when the preservative is not used or the preservative is weak, the risk of the deterioration of the product and the contagion of the pathogen are large, and the use of the preservative Is inevitable.

Isothiazolinone-based ingredients such as methyl isothiazolinone, chloromethyl isothiazolinone, and benzyl isothiazolinone are still used for preservation purposes in the clothing or dish or residential area cleaning or fragrance product line, Sodium benzoate, phenoxyethanol, octanediol and the like are used as low-molecular substances. Isothiazolinone is the most widely applied because it is economical and powerful, but it can be used as a carcinogen, and its regulations are expanding. Sodium benzoate, which has recently been used up, has been reported to cause hypertension, asthma attack, and kidney disease , There is a concern about safety due to the announcement that the mitochondria are inactivated to induce cell malfunctions. Phenoxyethanol is also synthesized by using phenol, which is a problem of residual phenol. Of these, octanediol is known to be relatively safe, but is used only in some of the consumer products due to its price / performance problems.

In recent years, preservatives have an impact on public health, and regulations are being strengthened in each product group in Korea. The regulations on the use of wet wipes as cosmetics legislation have been designated by the Korea Food and Drug Administration as the type of ingredients used and the limits of use of raw materials for kitchen detergents. A new economical yet safe preservative is required.

The inventors of the present invention have contemplated a method of controlling microorganisms in a different manner without using conventional preservatives harmful to the human body by various routes and it is believed that the mechanism of action of some microbial control components can be realized as a surfactant And that such cases have already been commercialized. However, most of the surfactant type preservatives have problems in that they are limited by ionic properties or easily hydrolyzed in liquid form when stored for a long period of time.

The present inventors have invented a surfactant-type preservative compound having an alkyl group starting from a plant component, that is, a fatty acid or a fatty alcohol as a hydrophobic group, thereby imparting solubilization and emulsifying ability and preventing damages , And found that the preservative effect can be imparted by selecting dihydric alcohol as a hydrophilic group.

The present invention relates to a surfactant-type preservative compound represented by the following general formula (1) or (2). 0.1 to 10% by weight of at least one compound selected from the group can be contained in the chemical composition.

[Chemical Formula 1]

(Wherein R ₁ is _one of H, CH ₃ and CH ₂ CH ₃ , and R ₂ as a hydrophilic group is an alkyl or alkenyl group having 6 to 18 carbon atoms.)

(2)

(Wherein R ₁ is _one of H, CH ₃ and CH ₂ CH _{3 and} is an alkyl or alkenyl group having 5 to 17 R ₃ carbon atoms as a hydrophilic group.)

In view of the molecular structure in the above-mentioned chemical structure, it is preferable to use a 3-alkylamino-1,2-propanediol compound wherein R ₁ of H is H, R ₁ of CH ₂ is CH ₃ , -N- (2,3- dihydroxy-propyl) alkyl amine compound, R ₁ in R ₁ of formula 2 is to color alkyl glycine in the H-dihydroxy, [Chemical formula 2] CH ₃ a, N- methyl (2,3-dihydroxypropyl) alkylamide compounds can be used for microbial control relatively effectively, and the alkyl group length of the hydrophobic moiety can be reduced by using a palm or palm-based material having a structure of 8 carbon atoms Friendly nature, and the emulsification and solubilizing effect of the surfactant structure was also excellent, and thus it was evaluated as a highly efficient structure.

The surfactant-type preservative compound of the present invention exhibits a wide range of microbial control ability, and it is possible to solve problems such as human toxicity and skin irritation caused by preservatives.

It was confirmed that when the components invented by the present inventors were included in products of various formulations, emulsification and solubilization were supported in accordance with the surfactant characteristics, while the antimicrobial activity was excellent and exhibited a broad antibacterial spectrum. In addition, the surfactant-type preservative compound of the present invention exhibits a wide range of applications because it can be widely used in anionic surfactant-based compositions and cationic surfactant-based compositions.

1 is a graph showing the MIC (minimum inhibitory concentration) of the preservative compound of the present invention and other preservative agents against bacteria.
2 is a graph showing the MIC (minimum inhibitory concentration) of fungi of the preservative compound of the present invention and other preservatives.

Hereinafter, preferred embodiments of the present invention will be described. However, the embodiments of the present invention can be modified into various other forms, and the scope of the present invention is not limited to the embodiments described below.

The preservative of the present invention is a surfactant-type compound having the structure of Chemical Formula (1) or (2), and 0.1 to 10% by weight of one or more selected compounds may be contained in the chemical product.

[Chemical Formula 1]

(Wherein R ₁ is _one of H, CH ₃ and CH ₂ CH ₃ , and R ₂ as a hydrophilic group is an alkyl or alkenyl group having 6 to 18 carbon atoms.)

(2)

(Wherein R ₁ is _one of H, CH ₃ and CH ₂ CH ₃ , and is an alkyl or alkenyl group having 5 to 17 R ₃ carbon atoms as a hydrophilic group.)

Preferably R ₁ in Formula 1 the R ₁ is H, 3-alkyl-1,2-propanediol compounds, [Formula 1] of the compound is CH ₃ a, N- methyl -N- (2, (2, 3-dihydroxypropyl) alkylamine compound represented by the formula (2) wherein R ₁ is H, dihydroxyethylalkylglycine, and R ₁ is CH ₃ , 3-dihydroxypropyl) alkylamide compounds can be effectively used for the purposes of the present invention, and the alkyl group length of the hydrophobic moiety can be reduced to a more natural-friendly structure using palm or palm- And the emulsification and solubilizing effect of the surfactant structure was also excellent.

In the following examples, the representative four derivatives of the present invention were synthesized, and the data of the test were selected by selecting a compound having the most effective lauryl alkyl group among them. However, the present invention is not limited to the lauryl group .

Test results comparing the four representative surfactant-type preservative compound structures synthesized by the present invention with the MIC concentration (minimum microbial inhibitory concentration) of phenoxyethanol and sodium benzoate, which are widely commercialized, are summarized in FIG. 1 and FIG. 2 .

As shown in the test results, all four of the compounds of the present invention are present in the form of a mixture of conventional phenoxyethanol, sodium benzoate, sodium benzoate, Eight inhibited microorganisms at lower concentrations. Especially for fungi.

Hereinafter, the present invention will be described in detail with reference to the preferred embodiments. The present invention is applied to a variety of life chemical compositions to be easily carried out by those skilled in the art. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

[Examples 1 and 2 and Comparative Examples 1 and 2] Liquid detergent composition for clothes

Constituent content(%) Example 1 Example 2 Comparative Example 1 Comparative Example 2 Laurel-7 15.0 - 15.0 - Alkylbenzenesulfonic acid salt - 20 - 20 Sodium laureth-2 sulfate (70%) 3.0 7.0 3.0 7.0 Protease 0.1 12.0 0.1 12.0 Lipase 0.1 0.1 Coco fatty soap 2.5 2.5 Sodium xylenesulfonate (30%) 2.0 2.0 2.0 2.0 Spices 0.15 0.12 0.15 0.12 room
part
My Benzyl isothiazolinone - - 0.2 - Methyl / chloromethylisothiazolinone - - - 0.05 3-laurylamino 1,2-propanediol 0.2 - - - N-Methyl-N- (2,3-dihydroxy
Propyl) laurylamide - 0.2 - -

[Examples 3 and 4 and Comparative Example 3] A fabric softener composition

Constituent content(%) Example 3 Example 4 Comparative Example 3 Dihydroxyethyl chilled dialkyl ester ammonium methyl sulfate (90%) 18.0 18.0 18.0 Cetearyl alcohol 0.5 0.5 0.5 Laureth-20 0.5 0.5 0.5 Silicone defoamer 0.03 0.03 0.03 Spices 0.4 0.4 0.4 room
part
My Alkylbenzalkonium chloride - - 0.2 Lauryl amino 1,2-propanediol 0.2 - - N-Methyl-N- (2,3-dihydroxypropyl)
Laurylamine - 0.2 -

[Examples 5 and 6 and Comparative Examples 4 and 5] The kitchen detergent composition

Constituent content(%) Example 5 Example 6 Comparative Example 4 Comparative Example 5 Sodium laureth-2 sulfate (28%) 52.0 3.0 45.0 52.0 Alpha olefin sulfate (35%) 12.0 3.5 12.0 12.0 Amine oxide (30%) 7.0 - 6.6 7.0 Alkyl polyglucoside (50%) 12.0 - - 12.0 Alkylbenzenesulfonic acid salt - 12.0 - - Sodium xylene sulfonate (30%) 2.0 - - 2.0 Citric acid 0.7 - 0.2 0.7 Spices 0.2 0.2 0.2 0.2 room
part
My Benzoate - - 0.7 - Methyl / chloromethylisothiazolinone - - - 0.05 N-Methyl-N- (2,3-dihydroxy
Propyl) laurylamide 0.2 - - - Dihydroxyethyllauriliacein - 0.2 - -

[Examples 7, 8 and Comparative Example 6] A bathroom cleaner composition

Constituent content(%) Example 7 Example 8 Comparative Example 6 Alkyl polyglucoside (50%) 5.0 5.0 5.0 Lauryl amine oxide (30%) 2.0 2.0 2.0 Dipropylene glycol n-butyl ether 3.0 3.0 3.0 Diethylene glycol monobutyl ether 2.0 2.0 2.0 Caustic soda 1.0 1.0 1.0 Sodium xylene sulfonate (30%) 2.0 2.0 2.0 room
part
My Diphenyldimethylammonium chloride - - 0.5 N-Methyl-N- (2,3-dihydroxy
Propyl) laurylamine 0.5 - - N-Methyl-N- (2,3-dihydroxy
Propyl) laurylamide - 0.5 -

[Example 9 and Comparative Examples 7 and 8] Wet tissue stock solution composition

Constituent content(%) Example 9 Comparative Example 7 Comparative Example 8 Natural extracts 0.1 0.1 0.1 room
part
My Hexanediol / octanediol / propanediol - 0.3 - Phenoxyethanol - - 0.5 3-laurylamino 1,2-propanediol 0.3 - -

[Example 10 and Comparative Example 9, 10]

Constituent content(%) Example 10 Comparative Example 9 Comparative Example 10 Spices 0.3 0.3 0.3 Hydrated castor oil-40EO 0.4 0.4 0.4 Dipropylene glycol 0.4 0.4 0.4 room
part
My Benzyl isothiazolinone - 0.7 - Phenoxyethanol - - 0.5 3-laurylamino 1,2-propanediol 0.3 - -

For the above Examples and Comparative Examples, a challenge test was conducted for each of bacteria and fungi as in Test Method 1 below.

[Test method 1] Challenge test

For each of the daily chemical compositions prepared according to the examples and comparative compositions, 10 ml of water was added to each of 5 test tubes and the respective products were added. The water-insoluble components were first added to the dipropylene glycol and then added.

Three mixed bacteria and two mixed fungal cultures were added to each of the five test tubes (about 10 ⁶ to 10 ⁷ cfu). The three mixed bacteria were Escherichia Coli), Staphylococcus aureus (Staphylococcus Aureus), Pseudomonas aeruginosa (Pseudomonas The Aeruginosa), mixed fungi is Candida (Candida Albicans), black Aspergillus (Aspergillus niger).

Bacteria were inoculated into NA (Nutrient agar) medium, and fungi were inoculated into PDA (Potato dextrose agar) medium and cultured in an incubator at 30 ° C. for 24 hours. In addition, the composition samples, that is, the composition samples of Examples and Comparative Examples were allowed to stand for 3 days, then inoculated into NA medium and PDA medium in the same manner as above, and cultured in an incubator at 30 ° C for 24 hours, Were measured. Thereafter, the maintenance of the sterilizing power of the composition was confirmed in units of 1 day, 2 days, 3 days, 7 days and 14 days.

The results of the tests are shown in [Table 7] to [Table 10]. As shown in the test results, it was found that the compositions containing the compound of the present invention effectively controlled bacteria and fungi as compared with commercial products.

Tables 7 and 8 are the results of the bacterial and fungal challenge test for Examples 1 to 10, respectively.

time Example
One Example
2 Example
3 Example
4 Example
5 Example
6 Example
7 Example
8 Example
9 Example
10 Day 0 TNTC 620 530 420 TNTC TNTC TNTC TNTC 440 420 Day 1 712 220 0 0 430 380 220 418 35 60 Day 3 0 0 0 0 80 48 0 20 0 0 Day 7 0 0 0 0 0 0 0 6 0 0 Day 14 0 0 0 0 0 0 0 0 0 0

time Example
One Example
2 Example
3 Example
4 Example
5 Example
6 Example
7 Example
8 Example
9 Example 10 Day 0 TNTC TNTC 430 390 TNTC TNTC TNTC TNTC TNTC TNTC Day 1 440 320 0 0 380 375 410 380 310 260 Day 3 20 60 0 0 80 48 70 20 20 80 Day 7 0 0 0 0 0 0 4 6 0 0 Day 14 0 0 0 0 0 0 0 0 0 0

Tables 9 and 10 show results of the bacterial and fungal challenge test for Comparative Examples 1 to 10, respectively.

time Comparative Example
One Comparative Example
2 Comparative Example
3 Comparative Example
4 Comparative Example
5 Comparative Example
6 Comparative Example
7 Comparative Example
8 Comparative Example
9 Comparative Example 10 Day 0 TNTC TNTC TNTC TNTC TNTC TNTC TNTC TNTC TNTC TNTC Day 1 420 180 82 TNTC 270 270 180 TNTC 300 TNTC Day 3 86 0 0 48 62 62 28 60 62 120 Day 7 0 0 0 6 0 0 0 0 0 0 Day 14 0 0 0 0 0 0 0 0 0 0

time Comparative Example
One Comparative Example
2 Comparative Example
3 Comparative Example
4 Comparative Example
5 Comparative Example
6 Comparative Example
7 Comparative Example
8 Comparative Example
9 Comparative Example 10 Day 0 TNTC TNTC TNTC TNTC TNTC TNTC TNTC TNTC TNTC TNTC Day 1 450 122 TNTC TNTC 420 TNTC TNTC TNTC 410 TNTC Day 3 136 30 280 48 89 298 300 105 50 160 Day 7 30 0 78 6 0 4 90 24 0 38 Day 14 0 0 6 0 0 0 0 0 0 0

Claims (8)

A microorganism consisting of Escherichia Coli , Staphylococcus Aureus , Pseudomonas Aeruginosa , Candida Albicans and Aspergillus niger , which contains a compound represented by Chemical Formula 1 or Chemical Formula 2, Surfactants to control.
[Chemical Formula 1]

(Wherein R ₁ is _one of H, CH ₃ and CH ₂ CH ₃ , and R ₂ as a hydrophilic group is an alkyl group or an alkenyl group having 6 to 18 carbon atoms.)
(2)

(Wherein R ₁ is _one of H, CH ₃ and CH ₂ CH ₃ , and R ₃ as a hydrophilic group is an alkyl or alkenyl group having 5 to 17 carbon atoms.)
The method according to claim 1,
The compounds are surface active agent characterized in that [Chemical Formula 1] R ₁ is an H, 3-alkyl-1,2-propanediol.
The method according to claim 1,
Wherein said compound is N-methyl-N- (2,3-dihydroxypropyl) alkylamine wherein R _{1 in the} formula (1) is CH ₃ .
The method according to claim 1,
Wherein said compound is dihydroxyethylalkylglycine, wherein R _{1 in} Formula 2 is H.
The method according to claim 1,
Wherein said compound is N-methyl-N- (2,3-dihydroxypropyl) alkylamide wherein R ₁ in CH ₂ is CH ₃ .
A liquid-based biochemical composition comprising water, characterized by containing the surfactant of claim 1.
The method of claim 6,
Wherein the surfactant is contained in an amount of 0.01 to 10% by weight based on the total weight of the composition.
The method of claim 6,
The water-containing liquid household chemical composition may be selected from the group consisting of laundry detergents, fabric softeners, dishwashing detergents, dishwasher detergents, residential space cleaners, wet tissues, deodorants, air cleaners, indoor fragrances, odorants, multipurpose cleaners, disinfectants, Wherein the composition comprises at least one of the following components:

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