Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1994-05-19
1996-07-09
Gupta, Yogendra N.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544200, C07D25154
Patent
active
055346243
DESCRIPTION:
BRIEF SUMMARY
The invention relates to 1,3,5-triazine-2,4,6-tris-alkylaminocarboxylic acid amino esters, biocidal and biostatic agents containing such amino esters and methods of preparing them. The abovementioned compounds are called "amino esters of the invention" below.
The triazinetricarboxylic acids on which the amino esters of the invention are based, that is to say the 2,4,6-tris(omega-carboxyalkylamino)-1,3,5-triazines, called 1,3,5-triazine-2,4,6-tris-alkylaminocarboxylic acids below, are described in J. Prakt. Chemie, 23 (1963), pages 173 to 185, and in EP-B 0 046 139. EP-B 0 046 139 furthermore relates to the use of the triazinetricarboxylic acids mentioned and alkali metal and mono-, di- or triethanolammonium salts thereof as corrosion inhibitors in aqueous systems. EP-B 0 046 139 furthermore describes the mono-, di- and triethanolammonium salts of these triazinetricarboxylic acids, which can be employed as corrosion inhibitors in aqueous systems; an analogous use of these compounds in aqueous systems, for example cooling liquids, cooling lubricants, paints or cleaning agents, is disclosed in EP-A 0 262 086.
Biocidal or biostatic agents have to be added to aqueous systems of the abovementioned type for prevention of attack by bacteria, yeasts and/or fungi. Halogen-containing compounds and, for example, boric acid and reaction products of boric acid with alkanolamines have been used to date as agents which are suitable for this purpose, see Ullmanns Encyklopadie der technischen Chemie (Ullmann's Encyclopaedia of Industrial Chemistry), 4th edition, Volume 8, Verlag Chemie, Weinheim 1974, pages 653-655. In other cases, formaldehyde or formaldehyde derivatives have been added as the biocide. However, for various reasons, halogen-containing compounds, boric acid and boric acid derivatives and also formaldehyde and derivatives thereof are undesirable. There is therefore an increasing need for biocidal agents which can be used in aqueous systems and are free from halogen-containing compounds, formaldehyde, formaldehyde derivatives, boric acid or boric acid derivatives.
It has now been found that the amino esters of the invention display excellent biocidal or biostatic properties when used in aqueous systems of the above-mentioned type even in low concentrations.
The invention accordingly relates to 1,3,5-triazine-2,4,6-tris-alkylaminocarboxylic acid amino esters of the general formula ##STR1## in which n denotes a number in the range from 4 to 11 and R.sup.1 denotes a radical of an alkanolamine of the general formula three of the groups R.sup.2 have the above meaning, the other groups R.sup.2 are hydrogen.
A preferred embodiment of the invention relates to amino esters of the general formula I in which n denotes the number 5.
The alkanolamines of the general formula II contain primary, secondary or tertiary amino groups and free hydroxyl groups. In the reaction of alkanolamines containing primary or secondary amino groups with carboxylic acids, both amides and esters which are in equilibrium with one another can be formed, see "Surfactants in Consumer Products", editor J. Falbe, Springer-Verlag, Heidelberg 1987, page 96. For clarity, the reaction products of 1,3,5-triazine-2,4,6-tris-alkylaminocarboxylic acids with alkanolamines to give compounds of the general formula I in which R.sup.1 is the radical of an alkanolamine of the general formula II are shown here only as amino esters. However, it can readily be seen by the expert that the corresponding alkanolamides also fall under the 1,3,5-triazine-2,4,6-tris-alkylcarboxylic acid derivatives thus defined.
Typical examples of hydroxyalkyl groups having 2 to 4 carbon atoms which can form the group R.sup.2 are 2-hydroxyethyl, 1-methyl-2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl, 4-hydroxybutyl and 2-methyl-2-hydroxypropyl groups; typical examples of hydroxyalkyl-oxyalkylene groups having in each case 2 to 4 carbon atoms in the hydroxyalkyl and oxyalkylene radical are hydroxyethyl-oxyethylene, hydroxypropyloxyethylene, hydroxyethyl-diethyleneoxy, h
REFERENCES:
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Nestler, H., et al., "Preparation of N-(1,3,5-triazinyl)amino acid derivatives", Chemical Abstracts, vol. 60, Abstract No. 4145e, Col. 4144 (1964).
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Lesmann Jorg
Schafer Hermann G.
CG-Chemie GmbH
Dreger Walter H.
Gupta Yogendra N.
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