Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – For cleaning a specific substrate or removing a specific...
Reexamination Certificate
2000-11-28
2002-07-16
Hardee, John (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
For cleaning a specific substrate or removing a specific...
C510S329000, C510S518000
Reexamination Certificate
active
06420330
ABSTRACT:
BACKGROUND OF THE INVENTION
Microbicidal agents are generally used to stop microorganisms from proliferting or to destroy them altogether. Hitherto, quaternary ammonium compounds, such as benzalkonium chloride or cetyl trimethyl ammonium chloride, have been successfully used as microbicidal agents. Unfortunately, it has been found that such compounds are not readily biodegradable in sewage treatment plants. Accordingly, there is a need for microbicidal compounds which are comparable in their performance with the quaternary ammonium compounds, but which have distinctly improved biological degradability.
U.S. Pat. No. 3,910,971 describes quatemary carboxylic acid alkanolamine ester salts obtainable by reaction of 2-dimethylamino-2-methyl-1-propanol with fatty acids and subsequent quatemization as microbicidal agents. However, these compounds are largely ineffectual against the gram-negative bacterium Pseudomonas aeruginosa which is a disadvantage in view of the commonly occurring waterborne germ which leads above all to product contamination.
European patent application EP 0 461 419 describes poly(oxy-lalkylene)aminoalkanol esters and ammonium compounds thereof which are also said to show microbicidal activity. However, these compounds have to contain at least one hydroxyisopropyl group and bear a methyl group at the nitrogen atom. No mention is made of the effectiveness of these compounds against bacteria, particularly against the commonly occurring bacterium
Pseudomonas aeruginosa.
The problem addressed by the present invention was to provide microbicidal compounds which would be comparable in their microbicidal activity with conventional quaternary ammonium compounds. Above all, the compounds would also be microbicidally active against the commonly occurring bacterium
Pseudomonas aeruginosa.
In addition, the compounds would show better biodegradability than the conventional quatemary ammonium compounds.
BRIEF SUMMARY OF THE INVENTION
The present invention includes the use of quaternary carboxylic acid alkanolamine ester salts as microbicidal agents, more particularly in detergents, disinfectants, preservatives, fabric softeners, cosmetics, cooling lubricant emulsions and in coating compositions. The present invention also relates to detergents, fabric softeners, disinfectants, preservatives, cosmetics, cooling lubricant emulsions and coating compositions containing these quaternary carboxylic acid alkanolamine ester salts.
It has been found that special quaternary carboxylic acid alkanolamine ester salts satisfy this requirement.
Accordingly, the present invention relates to the use of quaternary carboxylic acid alkanolamine ester salts corresponding to general formula (I):
in which
R
1
CO is an acyl group containing 2 to 18 carbon atoms,
R
2
and R
3
independently of one another represent an alkyl group containing 1 to 16 carbon atoms or a group with the formula CH
2
—CH
2
—O—R
5
,
R
4
is an alkyl group containing 1 to 4 carbon atoms,
R
5
is hydrogen and/or R
1
CO and
X
−
is an anion,
as microbicidal agents.
DETAILED DESCRIPTION OF THE INVENTION
The quaternary carboxylic acid alkanolamine ester salts are compounds known from the literature which are often also referred to as “esterquats”. They are generally prepared by esterification of the alkanolamines with carboxylic acids in the presence of hypophosphorous acid, passing air through the reaction mixture and then quatemizing the esterification product. U.S. Pat. Nos. 3,915,867, 4,370,272, EP-A0 239 910, EP-A-0 293 955, EP-A0 295 739 and EP-A-0 309 052 are cited here are representative of the abundant prior art available on the subject.
According to the invention, the quaternary carboxylic acid alkanolamine ester salts are prepared by methods known per se, alkanolamines corresponding to formula (II):
in which R
2
and R
3
are as defined for formula (I), with the proviso that, where R
2
and/or R
3
represent(s) the group CH
2
CH
2
OR
5
, R
5
is hydrogen, being esterified with carboxylic acids corresponding to the formula R
1
COOH. The alkanolamines corresponding to formula (II) may also be transesterified with esters of the described carboxylic acids to give the compounds of formula (I) used in accordance with the invention. Suitable alkanolamines are dialkyl ethanolamines (R
2
, R
3
=alkyl group containing 1 to 16 carbon atoms), such as dimethyl ethanolamine, methylethyl ethanolamine, diethyl ethanolamine, methylbutyl ethanolamine and/or methylhexyl ethanolamine, monoalkyl diethanolamines (R
2
=CH
2
CH
2
OH; R
3
=C
1-16
alkyl group), such as methyl diethanolamine, ethyl diethanolamine and/or butyl diethanolamine, and/or triethanolamines (R
2
, R
3
=CH
2
CH
2
OH). Monoalkyl diethanolamines and/or triethanolamines are preferably used.
Suitable carboxylic acids R
1
COOH are aliphatic saturated and/or unsaturated carboxylic acids, more particularly aliphatic saturated carboxylic acids, such as acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid, pelargonic acid, lauric acid, myristic acid, palmitic acid and the technical mixtures thereof obtained, for example, in the pressure hydolysis of natural fats and oils. Aliphatic saturated carboxylic acids containing 8 to 12 carbon atoms are preferred so that R
1
CO in formula (I) is preferably an aliphatic saturated acyl group containing 8 to 12 carbon atoms.
The quantity ratio of carboxylic acids or carboxylic acid esters to the alkanolamines is determined by the required degree of esterification of the free hydroxyl groups of the alkanolamines. In the case of the preferred monoalkyl diethanolamines and triethanolamine, all or only some of the free hydroxyl groups can be esterified with the carboxylic acids. If the hydroxyl group is not esterified, R
5
in general formula (I) stands for R
1
CO. The esterification may be complete or partial. Where esterification is partial, the average degree of esterification of the—overall—free hydroxyl groups in the case of the monoalkyl diethanolamines is preferably in the range from 1.2 to 1.7 and, in the case of the triethanolamines, is preferably in the range from 1.2 to 2.5, i.e. mixtures of mono-, di- and optionally triesters of the di- or triethanolamines with carboxylic acids are present. According to the invention, at least two of the free hydroxyl groups in the triethanolamine are esterified with carboxylic acids. Instead of the carboxylic acids, ester derivatives thereof with the alkanolamines may also be reacted.
The subsequent quaternization is carried out by the methods known in this field and leads to the quaternary carboxylic acid alkanolamine ester salts corresponding to general formula (I). Compounds with the formula R
4
X, where R
4
is as defined for formula (I) and preferably stands for a methyl group, are used for the quaternization. Where X in general formula (I) stands for formate, acetate, tartrate, dicarboxylate, citrate, halide, sulfate or nitrate, the usual quaternization was followed by an anion exchange.
According to the invention, it is particularly preferred to use compounds of formula (I) in which R
2
is a group CH
2
CH
2
OR
5
and R
3
is a methyl group and/or in which R
2
and R
3
stand for a group CH
2
CH
2
OR
5
where R
5
is as previously defined. Examples of particularly suitable compounds are dimethyl diethanolammonium dicaprylic acid ester methosulfate, methyl triethanolammonium tricaprylic acid ester methosulfate, methyl triethanolammonium dicaprylic acid ester methosulfate and dimethyl diethanolammonium dipelargonic acid ester methosulfate.
According to the invention, the described compounds are used as microbicidal agents. In the context of the invention, microbicidal agents are understood to be chemicals which are capable of destroying, or preventing the proliferation of, bacteria, yeasts, fungi, viruses and protists.
Microbicidal agents corresponding to this definition may be used in any products where a corresponding effect is required. They are preferably used in detergents/cleaners, for example in manual dishwashing det
Stelter Norbert
Uphues Guenter
Cognis Deutschland GmbH
Drach John E.
Ettelman Aaron R.
Hardee John
LandOfFree
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