Asymmetrical mannich base derivatives and the production and uses thereof
AssigneeEthyl Corporation
InventorJohn T. Loper
Life of this patent
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Abstract
Compounds are described in which a polyamine moiety is linked to a phenolic moiety by a Mannich base linkage involving one of the amino groups of the polyamine moiety, and in which an aminoalkylene-poly(oxyalkylene) moiety is linked to the phenolic moiety by a Mannich base linkage involving an amino group of the alkylene-poly(oxyalkylene) moiety. Compounds of this type have been found to be highly effective in controlling the formation of intake valve deposits in internal combustion engines.
Claims43
A compound in which a polyamine moiety is linked to a phenolic moiety by a Mannich base linkage involving one of the amino groups of the polyamine moiety, and in which an aminoalkylene-poly(oxyalkylene) moiety is linked to said phenolic moiety by a Mannich base linkage involving an amino group of the alkylene-poly(oxyalkylene) moiety.
A compound of the formula:
- A--L--R--L'--R'
- wherein A is a polyamine group having 2 to 10 nitrogen atoms, and is derived from a polyamine;
- R is a phenolic group derived from a hydroxyaromatic compound;
- R' is an alkylenepoly(oxyalkylene) group derived from an amino-substituted alkylenepoly(oxyalkylene) compound, and in which the alkylene groups can be the same or different and contain from 2 to 20 carbon atoms each;
- L is a methyleneamino linkage in which the amino nitrogen atom is one of the nitrogen atoms of the polyamine group;
- and L' is a methyleneamino linkage in which the nitrogen atom of L' is a nitrogen atom of an amino substituent in the alkylenepoly(oxyalkylene) group.
A compound formed by reacting in the first stage a phenolic compound having at least two unsubstituted ortho positions or at least one unsubstituted ortho and one unsubstituted para position with an aldehyde and either (i) a polyamine having at least one primary or secondary amino group capable of undergoing a Mannich condensation reaction with said phenolic compound, or (ii) an alkylene-poly(oxyalkylene) compound having at least one primary or secondary amino group capable of undergoing a Mannich condensation reaction with said phenolic compound in proportions to form an intermediate Mannich condensation product enriched in mono-substituted Mannich condensation product, and then reacting said intermediate Mannich condensation product in a second stage Mannich condensation reaction with an aldehyde and whichever of (i) and (ii) was not used in the first stage.
Dependencies are inferred from the claim text.