DK151363B - DISINFECTIVES AND CONSERVATORS - Google Patents

Description

in 151363

The invention relates to disinfectants and preservatives based on aldehydes or aldehyde decomposers and phenols.

Aldehydes are characterized by good water solubility and good effect in their use as surface disinfectants. However, they are disadvantaged with the fact that in suspension experiments these require relatively long action times, so that a higher concentration of germs must be used for rapid killing, which results in a risk of irritation of the mucus obstructions. In addition, mixtures containing aldehyde or aldehyde-releasing substances, at higher concentrations, frequently have an unpleasant odor and have poor skin and material compatibility. Furthermore, a disadvantage is that their effect on fungi and yeast at the usual concentrations is unsatisfactory, since aldehydes 1 o show a lack of effect.

In contrast, phenols "are distinguished by short action times in suspension experiments. However, these exhibit only poor water solubility and frequently do not meet the requirements of a good surface disinfectant. An additional disadvantage of phenols is that they can only be readily biodegradable. particularly concerning the frequently used pentachlorophenol or sodium pentachlorophenolate, already used in admixture with aldehydes, to mitigate the lack of action of aldehydes against fungi and yeast, according to the guidelines of the German Society of Hygiene and Microbiology ( DGHM), cf. the Guidelines for the Study of Chemical Disinfectants, Third Revised Edition, Gustav F i sche ~

Verlag, Stuttgart, must kill a surface disinfectant within a period of 6 hours. This assumes that in the suspension experiment, at the same concentration, a killing is achieved within 30 minutes. For the surface test, test for 1, 2, 4 and 6 hours at the suspension trial after 1 \, 5, 15 and 30 minutes. A shorter time than 2½ minutes is not planned, as errors in the experiment would then be too large in relation to the 1 t idea.

Conducting the suspension test and the surface trial with formaldehyde. nlnt-arrHaTrliahv / rl nn nlvnval \ / icfA fnr fniMna 1 2 151363 and glyoxal in the suspension experiment a markedly weak effect.

Extremely high aldehyde concentrations must be used, which in practice due to the aforementioned are not possible. The results of the surface trial, on the other hand, are more advantageous. While the effect of the glutaraldehyde in the suspension experiment is better, this aldehyde has so far been unable to find further use due to its unpleasant odor.

Table 1 20 -: -----

Aldehyde Suspension test Surface test

Formaldehyde more than 3¾ 1% 15 Glutard in aldehyde 0.5¾ 0.5¾

Glyoxal more than 3¾ 0.2¾ In contrast, by disinfectants based on 2q of germicidal phenol are obtained in levels known in e.g. from U.S. Pat. Commercially available disinfectants contain up to 30¾ phenol and should generally be used in 2Vig solution to achieve a safe effect against staphylococci while the effect in the suspension experiment is achieved by

c

substantially lower concentrations.

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Table 2

Phenol Suspension Test Surface test 2-phenylphenol 0.2% more than 2% 4-chloro-3 - phenyl phenol 0.2¾ more than 2¾ 2,6-dibromo-4-methyl1 phenol 0.2¾ more than 2¾ 4-bromo ~ 2, 6-dimethyl phenol 0.2¾ more than 2¾10

Experiments with a combination of aldehyde · with phenols have so far been contemplated that condensation occurs between these compounds, so that the effect of such mixtures decreases substantially.

It has now surprisingly been found that certain phenols, which in themselves exhibit good anti-microbial activity, can be combined with aldehydes without the occurrence of an undesired condensation reaction. By adding conventional emulsifiers, storage-stable disinfectants and preservatives are obtained, which in themselves combine the benefits of both compound classes and also have a good effect and a broad spectrum of effect.

The invention thus relates to disinfectant and preservative agents.

O JT

Clays based on aldehydes or aldehyde decomposers and phenols containing phenols of the general formula

OH

3 ° .Of R 3 j R1

V

R 1, wherein R 1, R 2 and R 3 are the same or different and represent straight-chain or branched alkyl groups having 1 to 8 carbon atoms or chlorine or bromine.

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Preferred phenols are those in which R 1 and R 3 are similar, where particularly good results are obtained with phenols in which R 1 and R 3 represent bromine or a lower alkyl group having 1 to 3 carbon atoms, i. the methyl, ethyl or propyl residue. Also advantageous are phenols of the formula set forth, in which at least one of the substituents in the compounds R 1, R 2 and R 3 is chlorine and especially bromine. The brominated phenols are preferred over the chlorinated ones, especially because they have a more pleasant odor and are more easily biodegradable.

10

Examples of suitable phenols are 4-bromo-2,6-dimethylphenol, 4-bromo-2,6-diethyl phenol, 2.6-dibromo-4-methylphenol, 2.6-dibromo-4-ethylphenol, 2.6-dibromo-4 -neopentylphenol, 2,6-dibromo-4-octylphenol, and 4-chloro-2,6-dimethylphenol.

Of these, 2,5-dibromo-4-methylphenol and 4-bromo-2,6-dimethylphenol have been found to be particularly suitable.

The aldehydes used for use in the disinfectants and preservatives and their bactericidal action are known. Examples of such aldehydes which may additionally be used in intermediate

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thing with each other are: a) aliphatic aldehydes of 1-12 carbon atoms, i. formaldehyde for dodecanal; b) aliphatic dialdehydes having 1-5 carbon atoms, i. glyoxal 30 to glutardialdehyde, or c) g of ayolyl acid esters of aliphatic, cycloalic fatty or aryl-lifatic alcohols, and d) glyoxylic acid. 1

As aldehyde-providing compounds, e.g. hexamethylene tetramine and hexahydrotriazine as well as 0-acetals, such as the condensation product of acetal aldehyde and ethanol, are considered.

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The disinfectants of the invention may contain additional common additives, which include first and foremost emulsifiers as well as organic solvents.

Suitable emulsifiers are sodium alkyl sulfonate, sodium lauryl ether sulfate, triethanolammonium lauryl sulfate and sodium cumole sulfonate. In particular, solvents such as isopropanol, triethylene glycol and methylglycol can be used as solvents.

The disinfectants and preservatives according to the invention show excellent effect both in the suspension experiment and also in the surface disinfection, where the effective concentration in the suspension experiment differs slightly from that in the surface experiment, although the individual constituents of the composition are in lesser quantities than would be necessary. 15 if these are used alone to obtain comparable results in the suspension and surface test, as compared to the following Table 3 with the tables 1 and 2 set forth above.

Table 3

Phenol + aldehyde Suspension test Surface test 2 5 4-bromo-2,6-di methyl phenol + formaldehyde 0.5% 1% 4-bromo-2,6-dimethyl phenol + glutard in aldehyde 0.5% 1% 4-bromo -2,6-dimethylphenol + glyoxal 0.2% 0.2%

With an effective concentration of the disinfectants and preservatives of the invention of 0.2 to 1% in the surface test, these agents are a commercially available agent under the designation "Tego 51" which is clearly superior, as the subsequent test results show.

Surface Experiment 6 151363

Concentration Staff. E. coli _ on PVC lacquered PVC lacquered

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"Tego 51" wood wood 0.5¾> 6 h> 6h> 6h> 6 h 1%> 6 h> 5 h> 6 h> 6 h 10 2%> 6 h> 6 h 4 h 1 h

According to this, a concentration of 2¾ of the known agent in the surface test is not sufficient, however a concentration, as shown above, of 0.2¾ of a mixture consisting of 4-bromo-2,8-di methyl phenol and glyoxal is.

Comparative experiments with formulations of the invention (1 to 4) and known formulations (5 to 8), the composition of which is stated in wall 4 of the following Table 4, yielded the values given in Tables 5 and 6.

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Table 4 Forms 12345678 5

Phenol 4-bromo-2,6-dimethylphenol 10.0 10.0 10.0 10.0 10.0 4-Chloro-3-methylphenol 23.0 2-phenyl phenol 4.0 10 4-chloro-2 - benzylphenol 3.0

aldehyde

Glyoxal 8.0 4.0 6.0 8.0 G1utardia 1dehyde 7.5 5.0 5.0 Formaldehyde 7.5 3.0 3.6

Glyoxylic acid 0.5

Tr in all cool ami ii acetate 5.0

Sodium refrigerated sulfonate 25.0 25.0 30.0 25.0 30.0 25.0 25.0

Sodium lauryl ether sulfate 2.0

Tr in Ethano-1-ammon in umauryl sulfate 5.0 5.0 5.0 5.0 5.0

Sodium cumol sulfonate 2.5 2.5 2.5 2.5 2.5 2.5

Na 2 HPO 4 4.3 Isopropanol 15.0 15.0 15.0 15.0 15.0 15.0 15.0

Tr in ethylene glycol 10.0 10.0 10.0

Methylglycol 5.0

Water 34.5 25.0 20.0 20.5 20.0 42.5 78.6 44.5 3 0

The effect of surface disinfection was investigated according to the guidelines of DGHM section C II 3.

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Table 5

Surface disinfection 5

Wife. Staphylococci E. coli PVC lacquered PVC lacquered wood 10

Formula 0.5% 2 hours 4 hours 1 hour hourly call 1 1% 1 hour 1 hour 1 hour 1 hour 2% 1 hour 1 hour 1 hour 1 hour

Formula 0.5% 6 hours> 6 hours 4 hours 6 hours 15 ring 5 1% 4 hours 6 hours 2 hours 2 hours 2% 2 hours 4 hours 1 hour 1 hour

Formula- 0.5%> 5 hours> 6 hours 4 hours 6 hours call 6 1%> 6 hours> 6 hours 1 hour 2 hours 20 2%> 6 hours> 6 hours 1 hour 1 hour

Formula 0.5%> 6 hours 6 hours 2 hours 4 hours call 7 1% 4 hours 2 hours l hours 2 hours 2% 1 hour 1 hour 1 hour 1 hour 25

Formula 0.5% 6 hours> 6 hours 4 hours 6 hours ring 8 1% 4 hours 4 thaws 2 hours 2 hours 2% 1 hour 1 hour 1 hour 1 hour 3Ό The results clearly show the superiority of formulation 1 of the invention in comparison with formulations 5 and 6, which contain phenols alone, especially for the effect on staphylococci.

The effect of the suspension experiment was investigated in accordance with the guidelines of DGHM section C III 3a. Pipette 10 ml of the suspension to be tested each time into 0.2 ml of a seed suspension in a glass dish. After 2.5; 5; For 15 and 30 minutes, samples are taken by means of a swab and transferred to 10 ml of nutrient broth or oblique agar. After the standard incubation period, the test tubes are read. In the following Table 6, indicate how many minutes the growth was inhibited.

These results also show the superiority of Formulation 1 of the invention in comparison to Formulas 7 and 8, which contain aldehydes alone.

10 151363

Table 6

Suspension trial 5 Wife. Staf. E. coli Pseud. Proteus

Formula 0.25% 2.5 '5' 30 '15' ring 1 0.5% 2.5 '2.5' 30 '2.5' 10 1% 2.5 '2.5' 2.5 '2.5'

Formula 0.25% 30 '30' 60 '> 60' ring 7 0.5% 5 '15' 15 '30' 1% 2.5 '2.5' 5 '15' 15 Formula 0.25% > 30 '> 30'> 30 '> 30' ring 8 0.5%> 30 '> 30'> 30 '> 30' 1%> 30 '> 30'> 30 '> 30'

Formula 0.25% 15 '15'> 60 '30' 20 ring 5 0.5% 5 '2.5' 15 '2.5' 1% 2.5 '2.5' 2.5 '2, 5 '

Formula 0.25% 15 '15'> 60 '15' ring 6 0.5% 2.5 '2.5' 30 '2.5' 1% 2.5 '2.5' 2.5 '2 , 5 '

Furthermore, the beneficial effect of formulations of the invention which contain as active ingredients formaldehyde, glutaraldehyde or glyoxal and 4-bromo-2,6-dimethylphenol, as compared to those which contain only these aldehydes or phenols as active substances, The test results in Tables 8 and 9. The composition of the formulations studied is given in Table 7.

35 11 151363

Table 7 9 10 11 12 13 14 15 16 17 18 19 5

Formaldehyde 20- - 10- - - - -. -

Glutard in aldehyde - 20 - - 10-

Glyoxal -20-10-10 2-phenyl phenol ----- 20 ---- 4-chloro-3-methylphenol ______ 20 --- 2,6-dibromo-4 methylphenol -------- 20 - 15 4-bromo-2,6-di - methylphenol - - - 10 10 10 - - - 20

Propanol-2 20 20 20 20 20 20 20 20 20 20 20

Alkyl aryl polyglycol ether sulfate 20 (Na salt) 20 20 20 20 20 20 20 20 20 20 20

Dl of sodium ammonyl alcohol polyglycol ether sulfosuccinate 88888888888 Tr in ethanol amine n-lauryl sulfate 22222222222

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Further experiments were carried out with the following trisubstituted phenols: 2,6-dibromo-4-methylphenol 5 2,4,6-trimethylphenol 2.4,6-trioctylphenol 4-chloro-2,6-dimethyl phenol 4-chloro-2,6-dioctylphenol 4 -bromo-2,6-dioctyl phenol 2,6-dibromo-4-ethylphenol 2,6-dibromo-4-octylphenol 4-bromo-2,6-diethyl phenol

The formulations prepared with these phenols are listed in Table 10, the results obtained with these formulations in the suspension experiment 15 are listed in Table 11 and the results obtained in the surface study in Table 12.

The results show, as already stated above, that the trisubstituted phenols meet the requirements of the suspension study, but not the surface study. However, the effect of the surface study was quite surprisingly improved when additional formaldehyde, giutardialdehyde or glyoxal were added to the trisubstituted phenols. The corresponding formulations are listed in Table 13, the results obtained in the suspension study in Table 14 and the results obtained in the surface study in Table 15.

17 151363

Table 10 Formulation 5 20 21 22 23 24 25 26 27 28 2.6-dibromo-4-methylphenol 20 2.4.6-trimethylphenol 20 10 2,4,6-trioctylphenol 20 4-chloro-2,6-dimethylphenol 20 4-chloro 2,6-dioctylphenol 20 4-bromo-2,6-dioctylphenol 20,6-dibromo-4-ethylphenol 2,6-dibromo-4-octylphenol 4-bromo-2,6-diethylphenol 20

Propanol-2 20 20 20 20 20 20 20 20 20

Alkyl aryl polyglycol e thersulfate (Na salt) 20 20 20 20 20 20 20 20 20.

Disodium lauryl alcohol polyhydric alcohol ether sulfosuccinate 888888888 Triethanolamine lauryl sulfate 2 2 2 2 2 2 2 2 2

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Furthermore, the disinfectants and preservatives according to the invention are extremely durable. With regard to the storage stability of Formulation 1 of the invention, the following values were obtained by experiments carried out immediately and after 1 year of storage:

surface Disinfection

Staphylococci E. coli PVC lacquered wood PVC lacquered wood 10

Immediately 1 lh Ih lh lh 2 lh lh lh lh 15 After 1 year 1 lh lh lh lh 2 lh lh lh lh 20

Suspension in Wed trial

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These show that the effect persists even after prolonged storage.

Claims (5)

151363 Patent Claims. 1. Aldehyde-P disinfectant and preservative or aldehyde decomposing agents and phenols, characterized in that they contain phenols of the general molds 1 OH 10 r3 I; R 1, R 2 15 wherein R 1, R 2 and R 3 are the same or different and represent straight or branched chain alkyl groups having 1-8 carbon atoms or chlorine bromine. Disinfectants according to claim 1, characterized in that it contains phenols of the general formula I wherein R 1 and R 3 are the same. Disinfectants according to claim log2, characterized in that it contains phenols of the general formula 2ς I wherein R 1 and R 3 are the same and represent bromine or an alkyl group having 1-3 carbon atoms. Disinfectants according to claims 1 to 3, characterized in that they contain phenols of the general formula I, wherein at least one of the substituents R 1, R 2 and R 3 is chlorine or bromine. Disinfectants according to claims 1 to 4, characterized in that it contains as aldehydes one or more of the group 35 a) aliphatic aldehydes of 1-12 carbon atoms, b) aliphatic dialdehydes of 1-5 carbon atoms, POOR 151363 c) glyoxylic acid esters of aliphatic , cycling and the like in fatty or ara-lifatic alcohols, and d) glyoxylic acid.