JPS6024762B2 - Bacteriostatic and bactericidal compositions - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention consists in the use of long-chain N-aminoalkylaminoalkanols as antibacterial substances.

Alkylamines and alkyldiamines having alkyl groups having 8 to 18 carbon atoms are antimicrobial active substances known in the literature.

However, compounds of this type have the disadvantage that because of their dermatologically unfavorable properties and their strong amine odor, they can only be used to a limited extent as antimicrobial substances. By the way, the formula: [In the formula, R represents an alkyl group having 8 to 18 carbon atoms,
It has been found that the compounds and their salts in which x is from 2 to 6 are outstanding bacteriostatic and bactericidal substances and do not have the above-mentioned disadvantages.

The N-tested aminoalkanols which can be used according to the invention are prepared in a generally known manner by reacting the corresponding 1,2-epoxyalkane with an excess of diamine at elevated temperature, for example at the reflux temperature of the diamine. Manufactured.

As 1,2-epoxy alkanes, mention may be made in particular of those prepared from unbranched Q-olefins.

It is reacted in pure form or as a mixture of 1,2-epoxy alkanes of different chain lengths. However, it is also possible to use mixtures of epoxy alkanes which result from the preparation of Q-orphine. Amino/alkanols that can be used according to the invention are therefore, for example, 11 (2
1-aminoethylamino)-decanol-2, dododecanol-2, 1-heptadecanol-2; 1-(3-aminoethylamino)-dodecanol-2, hexadecanol-2, -octadecanol-2; 1 1-(4-amino-butylamino)-undecanol-2, -tridecanol-2, -bentadecanol-2, -heptadecanol-2; 1-(5-amino-bentylamino)-decanol-2 , -butladecanol-2, -octadecanol-2, -eicosanol-2;1-(6-ami/-
hexylamino)dodecanol-2, monohexadecanol-2, -heptadecanol-2 and -octadecanol-2.

1-(-amino-alkylamino) with different chain lengths/
)-Alkanol-2-compounds can likewise be used according to the invention.

Mixtures of this type include, for example, mixtures of 1-(2-aminoethylami/)dodecanol-2 and 1-(2-aminoethylami/)-tetradecanol-2, or mixtures of 1-(2-aminoethylami/)-tetradecanol-2, or A mixture consisting of minnowpropylamino)-tetradecanol-2-hexadecanol-2 and -octadecanol-2, or 1-(6-amino-hexylamino)-pentadecanol-2, one hexadecanol/one lu 2, -heptadecanol-2, -octadecanol-2 and -nonadecanol-2. N-based aminoalkanols and acids, especially aliphatic carboxylic acids having from 2 to 18 carbon atoms, such as acetic acid, lauric acid, stearic acid, sorbic acid, laurooleic acid,
Salts with oil acids are produced by conventional methods.

For use in antimicrobial agents, the N-aminoalkyl-aminoalkanols can be incorporated into liquid, pasty or solid preparations such as suspensions, milk solutions and solutions in organic solvents.

Antimicrobial agents of this type can be used in various fields, for example as cleaning agents, disinfectants and skin preservatives for textiles, floor coverings, hospital equipment, baths and industries such as the brewing and laundry industries. Preparations with antimicrobial action contain from 0.1 to 10% by weight of the substances which can be used according to the invention, based on the total product;
It is preferably used in an amount of 0.5 to 5% by weight. Furthermore, aminoalkanols are used to preserve industrial products that are subject to attack by bacterial or fungal or other microbial destruction, such as starch pastes, gelatin, disperse dyes, cutting oils and drilling oils. For use for this purpose, additions of 0.1 to 2% by weight, based on the material to be stored, are generally sufficient. The substances according to the invention are characterized by an excellent bacteriostatic and bactericidal action, which not only inhibits the growth of bacteria, but also has an advantageous use when used in low concentrations within an acceptable time to kill bacteria. can do.

Another particularly significant advantage of the materials that can be used in accordance with the invention is that they have good dermatological compatibility compared to long mirror fatty amines and fatty diamines.

Next, the present invention will be explained in detail based on Examples, but the present invention is not limited thereto.

■ Production Example 1 In a Class 2 flask equipped with a thermometer, a reflux condenser, and a rope frame machine, about 118 ml of ethylenediamine (8 mol) was added.
Heat to reflux temperature in °C.

184 kg (1 mol) of 1,2-epoxydodecane are added dropwise within 1 hour.

To complete the reaction, the mixture was further stirred at reflux temperature for 3 hours. The excess ethylenediamine is then distilled off under standard pressure. The resulting alcohol, 1-(2-amino-ethylamino)dodecanol 2, is separated from the high-boiling components by distillation. The yield is 214 kg of substance A, % of the theoretical value.
corresponds to Boiling point: 140℃/0.1 Hg, melting point: 7
4°C, amine number Actual value: 448 Calculated value: 457. It was also possible to prepare the following substances which can be used according to the invention in a similar manner. The data are summarized in Table 1:
Table 1 N-substituted aminoalkanols according to the invention prepared 1
) Freezing point 2) Non-distilled products The commercially available epoxide mixtures used in the preparation of several substances had approximately the following chain length distribution: 'a'C,2 to C,4
-epoxide mixture (wt%) C,2-olefin, terminal position 55C,4-olefin, terminal position 31C,2-olefin, internal position or branch position 5C,4-olefin, internal position or branch position 8'b-C. 5-C,8-epoxide mixture (wt%) C,5-olefin, terminal position
28C,6-olefin, terminal position
28C,7-olefin, terminal position
25C,8-olefin, terminal position
14 Example 2 The following salts were prepared by mixing the corresponding aminoalkanols with an amount of acid calculated from the amine number at room temperature: Table 2 Examples of the use of high 'B' in the amino alkanols prepared Example 3 In order to investigate the antibacterial action of several substances listed in Tables 1 and 2, the inhibitory action against the following test bacteria was determined:

[1] Staphylococcus aureus (2 x 1 bacteria per 1 inch)
Escherichia coli (1 [2 x 1 bacteria per unit] [3] Pseudomonas aeruginosa (1)
Kite (6 x 1 bacteria per liter) Candida Candida (5 x 1 bacteria per ml) The inhibitory concentration of the test product is ``Deutschen Gesellschaft Fuer Hyggine und Microbiologie'' (Deschen Wsellsc) Side f
tfmHygene skin dMikrobiology)
(1967) using a dilution test based on the testing procedure for biological disinfectants.

The desired test concentrations were prepared by mixing precisely measured solutions of the substances of appropriate concentration with the broth in sterile small tubes, the total volume being 10' in each case. Subsequently test the canaliculi for the bacterial concentration of the bacterial suspension 0.1
I was vaccinated with him. The inoculated tubules were incubated at 370° C. for 3 days in a 900° C. oviduct. It was subsequently determined to what extent the concentration of substances added to the culture medium was able to completely inhibit bacterial growth. The value thus confirmed was shown as the inhibitory concentration. Tests were performed at the following concentration levels: 500 legs, 2 breasts, 10 capes, 5 capes, 2 breasts, breasts, 5 legs, and 1 treated skin. In this dilution test, the inhibitory concentrations shown in Table 3 below for each of the above bacteria were confirmed for the individual products.

Table 3: Test side perspiration (ppm) From the above table, it is clear that the aminoalkanol and its salt according to the present invention have a very good inhibitory effect on bacteria and fungi.

Example 4 The bactericidal action of some of the substances listed in Table 1 was confirmed using a suspension test.

This test method is called ``Deutschechen Gesellschaft Für Higgine un,t Microbiologie'' (DC
utsChen snake sellsc also forHyge
ne side d Mikrobiologie) (196g King)
Based on the chemical disinfectant testing procedures described in . According to this procedure, the following bacterial suspension 0.1 [1]
Pivet measurements were made within the test at temperatures between 8 and 21°C. ○' Staphylococcus aureus (2 x 1 bacteria per 1) ■ Escherichia coli (1
[Bacteria per 2 x 1 pi]■ Pseudomonas aeruginosa (bacteria per 1M 6 x
1b) For this purpose, 100 test substances according to the present invention were diluted with 10 parts of tap water (German hardness: 16) and used.

1 minute, 2.5 minutes, 5 minutes, 10 minutes, 20 minutes, 30 minutes, 60 minutes
After an action time of 1 min and 12 pm, the material was removed from the test tube with a platinum loop and 3% Tween 80 was added.
and 1 o of culture solution containing 0.3% lecithin as a deinhibitor.
WZ was inoculated.

Cultures inoculated with bacteria were incubated at 370 °C. Cultures were macroscopically evaluated for growth after 6 days and bacterial time was determined in this way.

The results are summarized in Table 4 below. Table 4 Suspension test, germicidal pass test (min) It is clear from the above table that the substances according to the invention have a very good bactericidal action against bacteria.

Example 5 To test the topical synergism of several aminoalkanols according to the invention, a group of white rabbits were bottled with a small amount of a 2.5% solution of the test substance in olive oil into the conjunctival sac of the eye.

The reaction of the mucous membrane of the eye is expressed using Draize's dot diagram ["
“Safety Evaluation of Chemicals in Food, Drugs and Feed” (Ap.
tyof chem to praisalofthesa
icals ln fM illusions, drugs
and domestics), Ass. ofFooda
MDrug Officials of the United States. S, 49th
~52 pages (195 monochromes)] at 2 hours, 1 day, 2 days, 4 days, 6 days and 8 days after application.

The results of the mucosal compatibility test are shown in Table 5 below. Table 5 Mucosal Compatible Substances Concentration Compatibility A 2.5% Slight conjunctival reaction, observed in bed 2 days later D
2.5% slight thigh bulge 6. No findings after 1 day F 2.
5% moderate conjunctival reaction, 2 days later no lacrimal findings. 2.5% moderate conjunctival reaction, 4 days later, almost 7 years of discharge.

Significant conjunctival reaction, maximum level still 1% after 8 days
Example 6 The use according to the invention of N-aminoalkyl-aminoalkanols follows some examples of antimicrobial agents incorporating substances according to the invention.

Preservative and detergent in the laundry industry: Sodium sulfate, alcohol, and oil Part by weight of blood Sodium tripolyphosphate 32. Part by weight of sodium carbonate 9. parts by weight of sodium sulfate
13. parts by weight of water glass
5. Part by weight of sodium carboxymethyl cellulose 1. parts by weight

Claims (1)

[Claims] 1 Formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R represents an alkyl group having 8 to 18 carbon atoms,
x is 2 to 6] and a salt thereof. 2. A bacteriostatic and bactericidal composition according to claim 1, which contains a compound of formula (I) in an amount of 0.1 to 10% by weight, based on the total preparation, in the antibacterial agent. 3 0.1-2 for all products to be stored for storage
A bacteriostatic and bactericidal composition according to claim 1, comprising a compound of formula (I) in an amount of % by weight.