Monsanto Company

Charles J Upton

Marvin M Crutchfield

Victor D Papanu

Kent P Lannert

The alkali metal, ammonium and alkanol ammonium salts of polymeric acetal carboxylates are stable detergent builders under laundry use conditions but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams. Such polymeric acetal carboxylates can now be made by a process which comprises bringing together in a reaction zone under polymerization conditions an ester of glyoxylic acid and a molecular sieve, and adding an alkyl vinyl ether to the resulting polymer in the presence of the molecular sieve to stabilize the polymer against rapid depolymerization in alkaline solution. The preferred alkyl vinyl ether is ethyl vinyl ether.

Preparation of polymeric acetal carboxylates using molecular sieves

Ether carboxylates represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 are individually selected from the group consisting of alkyl containing up to 20 carbon atoms, and M.sup.1, M.sup.2 and M.sup.3 are individually selected from the group consisting of alkyl containing up to about 4 carbon atoms, are useful as intermediates to prepare the corresponding acid or alkali metal, ammonium and alkanol amine salts, which are useful as chelants, sequestrants and detergent builders.

Ether carboxylates containing three carboxylate groups

Ether and acetal carboxylates useful as detergent builders to replace sodium tripolyphosphate (STP) in detergent formulations are known to the art. Certain polymeric polycarboxylates are also known to the art but all of these products suffer from either having poor builder properties or they are not readily biodegradable. According to the present invention, a method is provided for preparing new and novel polymeric acetal carboxylates which are stable under laundry use conditions, but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams.

Method of preparing polyacetal carboxylates

1,3-Dioxolane and 1,3-dioxane polycarboxylates, and precursors thereof

Ether carboxylates represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of alkyl containing up to 20 carbon atoms and M.sub.1 and M.sub.2 are individually selected from the group consisting of alkyl containing up to about 4 carbon atoms, are useful as intermediates to prepare the corresponding acid or alkali metal, ammonium and alkanol amine salts, which are useful as chelants, sequestrants and detergent builders.

Ether dicarboxylates

Detergent formulations containing tetrahydropyran or 1,4-dioxane

Alkali metal salts of polymeric acetal carboxylate are stable detergent builders under laundry use conditions but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams. According to the improved process of the present invention, an ester of a polymeric acetal carboxylate is brought together in a reaction zone with a sufficient amount of an alkali metal base having a normality of at least 5 normal, and preferably at least 10 normal, to saponify at least 50 percent of the ester groups. In the preferred embodiment, the ester is contacted with a solvent to remove color-producing impurities.

Process for preparing polymeric acetal carboxylate salts

1,4-Dioxane polycarboxylates

This disclosure concerns: (a) compounds having the molecular structure represented by the formula ##STR1## wherein M is 0 or CY.sub.2, where Y is H or lower alkyl (C.sub.1 to C.sub.4), X is selected from the group consisting of H, lower alkyl (C.sub.1 to C.sub.4), or COOZ, Z represents H, R or a salt forming ion from the group alkali metal, ammonium, or trialkanolammonium, and R is an alkyl group (branched or straight chain) having up to about C.sub.20 in the chain. (b) a process for producing the compounds of (a) by the basic carboxylation of compounds represented by the formula ##STR2## wherein M, X and R are as described in (a), (C) SOLID AND LIQUID DETERGENT COMPOSITIONS COMPRISING COMPOUNDS OF (A) AND (d) washing processes employing the compounds of (a) and/or the compositions of (c).

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Ballwin, MO, United States of America

Charles J Upton