1. Field of the Invention
This invention relates to initial Mannich condensates prepared from a phenol, formaldehyde and an alkylamine containing internal propoxy groups and, optionally, ethoxy groups and to alkoxylated derivatives of the initial Mannich condensates that also contain hydroxy-terminated alkoxide side chains depending from the amino group of the initial Mannich condensates; such initial and/or alkoxylated Mannich condensates being useful as surfactants, corrosion inhibitors, water repellent agents, paint adhesion promoters, and as intermediates for the preparation of surfactants with a wide range of cloud points and detergency.
More particularly, this invention relates to initial Mannich condensates that are prepared by reacting formaldehyde with phenol or a phenol substituted in the ortho or para position with a hydrocarbon group and also with an alkylamine wherein the alkyl group is separated from the amine group by one or more propoxy groups or by a mixture of ethoxy groups and propoxy groups to thereby provide a new class of chemicals having a wide variety of useful properties. The preparation of the Mannich condensates of the present invention is illustrated by the following equation: ##STR1##
Where a equals 1 to 5, b equals 0 to 2, c equals 1 to 3, d equals 2 to 4; and Wherein: R represents an alkyl, an aryl and/or an alkaryl group; R' represents an aryl, arylalkyl or an alkyl group containing 1 to 20 carbon atoms; PO represents an oxypropyl group; EO represents an oxyethyl group; m is a number having a value of 1-50; and n is a number having a value of 0 to 50.
It is to be noted that in the equation given above, one phenolic hydrogen atom that is ortho or para to the phenolic hydroxyl group is replaced for each Mannich group that adds to the aromatic ring so that, in the final product, H.sub.d equals H.sub.a minus c.
This invention also relates to alkoxylated Mannich derivatives prepared from the initial Mannich condensates. The alkoxylated Mannich derivatives are prepared by reacting the initial Mannich condensate with an alkylene oxide feed stock comprising ethylene oxide, propylene oxide, 1,2-butylene oxide or a mixture thereof to thereby provide hydroxy-terminated groups derived from the alkylene oxide feed stock which are attached to the amino nitrogens of the initial Mannich condensate and to the phenolic hydroxyl group. In this fashion it is possible to convert an initial Mannich condensate having an initial utility to an alkoxylated derivative having an enhanced initial utility or a different utility. The formation of the alkoxylated Mannich condensates is illustrated by the following equation: ##STR2##
Wherein R" represents H, or methyl or ethyl; Z represents a positive integer having a value of 1 to 50; and Z.sub.a +Z.sub.b equals Z.
2. Prior Art
The Mannich reaction is a well known reaction which has been extensively reviewed in the literature. See for example, "The Mannich Reaction", Org. Reactions1, 303 (1942) and "Advances in the Chemistry of Mannich Bases", Methods in Synthetic Organic Chemistry - Synthesis, Academic Press, pp. 703-775, 1973.
A representative patent illustrating the manner in which the Mannich reaction can be utilized to prepare useful products is Schmitz U.S. Pat. No. 4,310,592. Schmitz reacts an aliphatic amine and formaldehyde with phenol to provide an ortho substituted Mannich base condensate which is useful for increasing the water repellent properties of materials treated therewith.