Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-05-19
1998-07-07
Kulkosky, Peter F.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
62184, A01N 4368
Patent
active
057769346
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP92/02248 filed Sep. 29, 1992.
The invention relates to 1,3,5-triazine-2,4,6-tris-alkylaminocarboxylic acid derivatives, their use as biocidal or biostatic agents in aqueous systems and cooling lubricants comprising these. The triazinetricarboxylic acids on which the derivatives 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.
An anticorrosion agent which comprises an imidazoline, one of the triazinetricarboxylic acids mentioned and at least one mono-, di- or trialkanolamine and water is described in EP-A 0 262 086. The corrosion inhibitors according to EP-B 0 046 139 and EP-A 0 262 086 are added to aqueous systems, for example cooling liquids, cooling lubricants, paints or cleaners, which in turn contain further additives, for example biocides. Additives which have been used to date are halogen-containing compounds and, for example, boric acid and reaction products of boric acid with alkanolamines, see Ullmanns Encyklopadie der technischen Chemie (Ullmann's Encyclopedia 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 biocide. However, halogen-containing compounds, boric acid and boric acid derivatives and also formaldehyde and derivatives thereof are undesirable for various reasons. 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 1,3,5-triazine-tris-2,4,6-alkylaminocarboxylic acid derivatives of the general formula ##STR1## in which
n denotes a number in the range from 4 to 11 and
R.sup.1 has one of the following meanings:
a) an alkali metal atom, one molar equivalent of an alkaline earth metal atom or an ammonium ion derived from an alkanolamine of the general formula atoms in the hydroxyalkyl and oxyalkyl radical or other groups R.sup.2 are hydrogen, or one of the groups R.sup.2 has the abovementioned meanings, the second is an alkyl group having 1 to 6 carbon atoms and the third is hydrogen,
b) a straight-chain or branched alkyl or alkenyl group having 1 to 23 carbon atoms,
c) a cycloalkyl group having 5 to 6 carbon atoms in the cyclic radical, which is optionally substituted by an alkyl group having 1 to 4 carbon atoms or by several groups,
d) a radical of a polyol having 2 to 15 carbon atoms and 2 to 6 hydroxyl groups, including addition products of ethylene oxide and/or propylene oxide onto the abovementioned polyols,
e) a radical of an addition product of ethylene oxide and/or propylene oxide on straight-chain or branched alcohols having 6 to 22 carbon atoms,
f) a radical of a polyethylene, polypropylene or mixed polyethylene/polypropylene glycol, the free hydroxyl group of which is optionally substituted by an alkyl group having 1 to 4 carbon atoms,
g) a radical of a hydroxycarboxylic acid having 2 to 18 carbon atoms,
h) a phenylalkyl group having 1 to 4 carbon atoms in the alkyl radical
i) a radical of an alkanolamine of the general formula II
According to a preferred embodiment of the invention, 1,3,5-triazine-2,4,6-tris-alkylaminocarboxylic acid derivatives of the general formula I in which n denotes a number in the range from 4 to 8, preferably the number 5, are used.
Alkali metal atoms can be lithium, sodium or potassium. Alkaline earth metal atoms can be magnesium or calcium.
The alkanolamines of the general formula II contain primary, secondary or tertiary amino and free hydroxyl groups. Both amides and esters, which are in equilibrium with one another,
REFERENCES:
patent: 4824845 (1989-04-01), Gehret et al.
Nestler, H., et al., "Preparation of N-(1,3,5-triazinyl)amino acid derivatives", Chemical Abstracts, vol. 60, Abstract No. 4145e, Col. 4144 (1964).
Chemical Abstracts, Registry Handbook--Number Section, (1986) Columbus US, pp. 2992, CAS RN 103479-85-2.
Chemical Abstracts, Registry Handbook--Number Section, (1982) Columbus US, p. 156, CAS RN 80584-91-4.
Chemical Abstracts, Registry Handbook--Number Section, (1982) Columbus US, pp. 156, CAS RN 80584-92-5.
Chemical Abstracts, Registry Handbook--Number Section, (1991) Columbus US, p. 3274, CAS RN 135043-68-4 & 135043-69-5.
Lesmann Jorg
Schafer Hermann Georg
CG-Chemie GmbH
Dreger Walter H.
Kresnak Mark T.
Kulkosky Peter F.
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