Henkel Kommanditgesellschaft Auf Aktien

Henkel & Cie G.m.b.h.

Henkel Kommanditgesellschaft Auf Aktien (henkel Kgaa)

Deutsche Gold- Und Silber-scheideanstalt Vormals Roessler

Karl-Heinz Worms

Helmut Blum

Walter Ploger

Peter Christophliemk

Wolfgang Friedemann

Manfred Schmidt-Dunker

Christian Gloxhuber

Gunter Jakobi

Hans-Ulrich Hempel

Christian Heine

Gerald Schreiber

Edmund Schmadel

Bruno Blaser

Hans-Gunther Germscheid

Ernst Vaeth

Klaus Wollmann

Norbert Schindler

A process for the preparation of a .omega.-amino-1-hydroxyalkylidine-1,1-biphosphonic acid of the formula ##STR1## wherein n is an integer from 3 to 5, consisting essentially of the steps of reacting an aminocarboxylic acid of the formula

Process for the production of

A process for the preparation of 3-amino-1-hydroxypropane-1,1-diphosphonic acid having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and lower alkyl, consisting essentially of the steps of reacting a .beta.-alanine compound selected from the group consisting of .beta.-alanine and lower alkylated .beta.-alanine with a phosphonating reactant selected from the group consisting of:

Process for the production of 3-amino-1-hydroxypropane-1,1-diphosphonic

Hydroxyalkane diphosphonic acids having the formula ##STR1## wherein X is a member selected from the group consisting of ##STR2## and their water-soluble salts; as well as the process of preparing the same. The compounds are excellent sequestering agents, especially for alkaline earth and earth metal ions. They are stabilizers for percompounds and are useful in the delaying of the setting times for gypsum. In addition, the compounds are useful in cosmetic preparations, such as toothpastes and mouthwashes where they prevent formation of tartar and plaque and are useful in therapy in the treatment of diseases related to the abnormal deposition or dissolution of difficultly soluble calcium salts in the animal body.

Hydroxyalkane diphosphonic acids

An appetite curbing preparation comprising an alginate and diphosphonic acid or a nontoxic pharmacologically acceptable water-soluble salt thereof as an inhibitor of the precipitation of calcium salts. This preparation is useful for curbing the appetite of a warm-blooded animal.

Appetite curbing preparation containing an alginate and a diphosphonic

Diphosphonoalkane carboxylic acids having the formula ##STR1## wherein R is H or --CH.sub.2 --CH.sub.2 --COOH; as well as their water-soluble salts. The compounds are excellent sequestering agents, especially for alkaline earth and earth metal ions. They are stabilizers for percompounds and are useful in the delaying of the setting times for gypsum. In addition, the compounds are useful in cosmetic preparations, such as toothpastes and mouthwashes where they prevent formation of tartar and plaque and are useful in therapy in the treatment of diseases related to the abnormal deposition or dissolution of difficultly soluble calcium salts in the animal body.

Diphosphonoalkane carboxylic acids, process of preparation and methods

A process for the production of a low-iron zeolitic alkali metal aluminosilicate from iron-containing, optionally previously activated, mineral aluminosilicate raw materials comprising subjecting the iron-containing, optionally previously activated, mineral aluminosilicate raw material in a charge of suitable molar ratios of

Process for the production of low-iron zeolitic aluminosilicates

A process for the production of 1-hydroxy-alkane-1,1-diphosphonic acids comprises reacting 1-amino-alkane-1,1-diphosphonic acids with nitrous acid, halides of nitrous acid or a substance forming nitrous acid under the reaction conditions.

Production of 1-hydroxy-alkane-1,1-diphosphonic acids

1,3-Di-amino-alkane-1,1-diphosphonic acids having the formula ##STR1## wherein R.sub.1 and R.sub.2 are members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms, and R.sub.3 is a member selected from the group consisting of hydrogen and methyl; as well as their water-soluble salts. The 1,3-diamino-alkane-1,1-diphosphonic acids are excellent sequestering agents especially for alkaline earth metal ions. The compounds are useful in pharmaceutical preparations for treatment of disturbances of calcium or phosphate metabolism or cosmetic preparations such as toothpastes or mouth washes for the prevention of tartar and plaque depositions.

1,3-Di-amino-alkane-1,1-diphosphonic acids and salts

A process for the manufacture of acylation products of a phosphorous acid having at least two phosphorus atoms in their molecules, which consists essentially of the steps of mixing one mol of phosphorus trichloride with from 2.5 to 3 mols of a mixture of carboxylic acid plus water, said acid being selected from the group consisting of an aliphatic monocarboxylic acid having 2 to 12 carbon atoms and benzoic acid; the share of said water in said mixture being from 1.2 to 1.5 mols; at a temperature up to 80.degree. C; heating the reaction blend thus obtained, after completing of said mixing to 100.degree. C to 160.degree. C and recovering said acylation products.

Process for the manufacture of acylation products of phosphorous acid

A process for the production of zeolitic alkali metal aluminosilicates by the reaction of aqueous alkali metal silicate solutions with an aqueous alkali metal aluminate solution containing sulfate anions at temperatures of 0.degree. C to 110.degree. C under a shearing type of agitation and conversion of the amorphous precipitate to crystalline forms by maintaining an aqueous suspension of the amorphous form at temperatures of 40.degree. C or over for a time sufficient to effect crystallization, whereby formation of substantial amounts of inactive nosean are avoided.

Process for the production of zeolitic alkali metal aluminosilicates

1-Hydroxy-3-amino-alkane-1,1-diphosphonic acids having the formula ##STR1## wherein X is a member selected from the group consisting of ##STR2## and ##STR3## wherein R.sub.1 is a member selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms and R.sub.2 is alkyl having 1 to 3 carbon atoms; as well as their water-soluble salts. The 1-hydroxy-3-amino-alkane-1,1-diphosphonic acids are excellent sequestering agents especially for alkaline earth metal ions. The compounds are useful in pharmaceutical preparations for treatment of disturbances of calcium or phosphate metabolism or cosmetic preparations such as toothpastes or mouthwashes for the prevention of tartar and plaque depositions.

1-Hydroxy-3-amino-alkane-1,1-diphosphonic acids and salts

Process for the preparation of 1-aminoalkane-1,1-diphosphonic acids of the formula ##STR1## in which R.sub.1 represents a member selected from the group consisting of alkyl with 1 to 20 carbon atoms, phenyl, phenylalkyl with 7 to 12 carbon atoms, alkylphenyl with 7 to 12 carbon atoms, and in which R.sub.2 represents a member selected from the group consisting of hydrogen and alkyl with 1 to 4 carbon atoms, consisting essentially of reacting adducts of a hydrogen halide selected from the group consisting of HCl and HBr to a corresponding carboxylic acid amide of the formula

Process for the preparation of 1-aminoalkane-1,1-diphosphonic acids

A process for the production of 1-aminoalkane-1,1-diphosphonates of the formula ##SPC1## Wherein R.sub.1 is a member selected from the group consisting of hydrogen, lower alkyl and phenyl, R.sub.2 and R.sub. 3 are members selected from the group consisting of hydrogen, alkyl having 1 to 22 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, phenyl, alkylphenyl having 7 to 18 carbon atoms, phenylalkyl having 7 to 18 carbon atoms and together with the nitrogen atom, piperidino, pyrrolidino and morpholino, and X is a member selected from the group consisting of hydrogen, alkali metal, ammonium, pyridinium, guanidinium and mono-, di-, and tri-lower-alkanol-ammonium with the proviso that at least one of R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, which consists essentially in reacting a phosphorus trihalide selected from the group consisting of phosphosus trichloride and phosphorus tribromide with a monocarboxylic acid amide of the formula ##SPC2## wherein the molecular weight of said carboxylic acid amide is over 46 and R.sub.1, R.sub.2 and R.sub. 3 have the above assigned meanings, at a temperature of from 0.degree. to 75.degree.C, subjecting the resultant reaction product to hydrolysis, and recovering said 1-aminoalkane-1,1-diphosphonates. The 1-aminoalkane-1,1-diphosphonates, some of which are novel, are capable of forming complexes with heavy metals.

1-Aminoalkane-1,1-diphosphonic acids and their salts

Washing agent compositions and washing assistant compositions containing from 0.5% to 70% by weight of a phosphonopolycarboxylate having the formula ##EQU1## WHEREIN Me is H, alkali metal, or H.NR.sub.3, R.sub.1 is H or CH.sub.3, R.sub.2 is H, alkyl having 1 to 4 carbon atoms or --CH.sub.2 --CHR--COOMe, R.sub.3 is H, alkyl or alkylol having 1 to 6 carbon atoms, and X is a direct bond or the groups ##EQU2## from 0 to 96.5% of other sequestering and non-sequestering, preferably phosphorus-free builders, and from 3% to 45% by weight of at least one surface-active compound of an anionic or non-ionic nature, whereby a 1% aqueous solution thereof has a pH of between 6 and 11.5. Preferably said phosphonopolycarboxylate sequestering agents are present as water-soluble salts capable of complex formation with alkaline earth metal ions. The invention also resides in the process of sequestering alkaline earth metal ions using aqueous solutions of the washing agent composition.

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Dusseldorf, Germany

Karl-Heinz Worms