Polyacetals, preparation thereof and use thereof in detergents

Details Polyacetals, preparation thereof and use thereof in detergents Polyacetals, preparation thereof and use thereof in detergents

1993-08-20

1995-03-21

Cain, Edward

Compositions

Water-softening or purifying or scale-inhibiting agents

25217421, 25217422, 25217424, C11D 300

Patent

active

053992865

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to polyacetals which as characteristic feature contain copolymerized units of the formula ##STR3## where R is hydrogen, C.sub.1 -C.sub.4 -alkyl or COOM, group, and the presence of initiators, and the use of the polyacetals as additives in low-phosphate or phosphate-free detergents.
EP-B 0 001 004 discloses polymeric acetal carboxylates obtainable by polymerizing glyoxylic esters in the presence of initiators. These polymers contain as characteristic feature at least 4 units of the formula ##STR4## where M is an alkali metal, ammonium, C.sub.1 -C.sub.4 -alkyl or alkanolamine group.
These polymers are used as builders in detergents in amounts of at least 1% by weight. The known polymeric acetal carboxylates hydrolyze relatively rapidly in an acid medium to form components which are biodegradable. However, the polymers are not easy to prepare, since the monomers, ie. the formyl esters, must first be prepared by heating the hemiacetal ester of glyoxylic acid in the presence of phosphorus pentoxide and purified. The esters are then polymerized using suitable initiators, such as strong Lewis acids or the sodium salt of diethyl malonate. The resulting polymers are capped at the end groups with structures which impart to the polymer the stability in alkaline media required for use in detergents.
The polymerization of .beta.-methoxycarbonylpropionaldehyde is known from Polm. Sci, Polymer Chemistry Edition 17 (1979), 2999-3007, and from Macromolecular Syntheses 7 (1979), 23-25.
It is an object of the present invention to provide novel detergent additives.
We have found that this object is achieved by the use of polyacetals containing copolymerized units of formula ##STR5## where R is hydrogen, C.sub.1 -C.sub.4 -alkyl or COOM, group, and from the group consisting of the C.sub.1 -C.sub.10 -aldehydes, C.sub.2 -C.sub.4 -alkylene oxides, epihalohydrins, epoxysuccinic acid and compounds of the formula ##STR6## where R' is C.sub.1 -C.sub.4 -alkyl, as copolymerized units, and having K values (determined by the method of H. Fikentscher on the sodium salt in 1% strength by weight aqueous solution at 25.degree. C. and pH 7) of at least 8.5, as additives in low-phosphate or phosphate-free detergents in amounts of from 0.1 to 30% by weight, based on the respective formulations.
The compounds of the formula II are known. Formyl esters of the formula II can be prepared for example by hydroformylation of monoethylenically unsaturated carboxylic esters with carbon monoxide and hydrogen at elevated temperatures and pressures; cf. for example J. Falbe, New Syntheses with Carbon Monoxide, Springer Verlag 1980, or J. Wender and P. Pino, Organic Synthesis via Metal Carbonyls, J. Wiley & Sons, 1977.
Preferred polyacetals contain units of the formula I where group. least one comonomer selected from the group consisting of the C.sub.1 -C.sub.10 -aldehydes, C.sub.2 -C.sub.4 -alkylene oxides, epihalohydrins, epoxysuccinic acid and compounds of the formula ##STR7## where R.sup.1 is C.sub.1 -C.sub.4 -alkyl, as copolymerized units. The polyacetals which contain copolymerized units of the formula I have K values (determined by the method of H. Fikentscher on the sodium salt in 1% strength by weight aqueous solution at 25.degree. C. and pH 7) of at least 8.5. Depending on the purity of the monomers which are used in the polymerization and the polymerization conditions, the polyacetals obtained have K values of up to 200 or higher. The number n of monomer units of the formula I in the polyacetals is at least 4 and can be up to about 500, and is preferably within the range from 4 to 120.
The polyacetals are prepared by polymerizing compounds of the formula ##STR8## where R.sup.2 is preferably methyl or ethyl, R is preferably hydrogen, and m is preferably 1-4, polymerization is carried out in the absence or presence of a solvent. Suitable solvents are for example halogenated hydrocarbons, such as dichloromethane and trichloroethane, aromatic hydrocarbons, such as benzene, toluene, isopropylbenzene and xylene, ethers such

REFERENCES:
Journal of Polymer Science, Polymer Chemistry Edition, Bd. 17, Nr. 9, 9 Sep. 1979, New York, US pp. 2999-3007; K. Hashimoto E. A.: `Equilibrium Anionic Polymerization of Beta-Methoxycarbonylpropionaldehyde`.
Macromolecular Syntheses. Bd. 7, 1979, New York US, pp. 23-25; K. Kbayashi E. A.: "Poly(Carbomethoxy-Ethyloxymethylene)".

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