The Clorox Company

Basf Aktiengesellschaft

Mid-america Commercialization Corporation

Kevin A Klotter

James E Deline

William L Smith

Lafayette D Foland

Alfred G Zielske

Michael J Petrin

Thomas W Kaaret

James W Arbogast

Martin J Phillippi

Clement K Choy

Aram Garabedian

Klaus Mundinger

Ulrich Annen

Sarah A Perkins

Michael M&uuml;ller

David A Peterson

Rudi Widder

James D Mitchell

Alfred Ruland

William P Sibert

Martin Scholtissek

Vincent E Alvarez

Martin A Phillippi

Michael Sch&ouml;nherr

Susan P Huestis

Michael M Ott

Ulrich Brockel

Gregor Sch&uuml;rmann

Victor M Casella

Wolfgang Sch&auml;fer

Josef M&uuml;ller

Hans Peter Seelmann-Eggebert

N-alkyl ammonium acetonitrile salts, methods therefor and compositions therewith

A process is provided for the preparation of a compound having the structure of Formula I

Process for preparing N-alkyl ammonium acetonitrile compounds

An improved synthesis for preparing a tetraamido-macrocyclic ligand, such as 5,6-Benzo-3,8,11,13-tetraoxo-2,2,9,9-tetramethyl-12,12-diethyl-1,4,7,10 -tetraazacyclotridecane, H.sub.4, in greatly improved yield and in a commercially viable manner, comprising the steps of dissolving a quantity of a 1,2-bis(2-aminoalkanamido)benzene in a solution comprised of ethyl acetate and methylene chloride to yield a first reaction solution; dissolving a quantity of a malonyl dihalide in an ethyl acetate solution to yield a second reaction solution; adding the first reaction solution and the second reaction solution to a reaction vessel containing a third reaction solution comprised of refluxing ethyl acetate solution and an acid scavenger to form a reaction mixture; and isolating a solid product comprised of the tetraamido-macrocycle directly from the reaction mixture by filtration.

Synthesis of a tetraamido macrocycle ligand

The invention provides liquid cleaning or bleaching compositions containing compounds having the structure of Formula I ##STR1## wherein A is a saturated ring formed by five atoms in addition to the N.sub.1 atom, the five saturated ring atoms being four carbon atoms and a heteroatom, the substituent R.sub.1 bound to the N.sub.1 atom of the Formula I structure including either (a) a C.sub.1-24 alkyl or alkoxylated alkyl where the alkoxy is C.sub.2-4, (b) a C.sub.4-24 cycloalkyl, (c) a C.sub.7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C.sub.2-4, or (e) --CR.sub.2 R.sub.3 CN where R.sub.2 and R.sub.3 are each H, a C.sub.1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C.sub.2-4, the R.sub.2 and R.sub.3 substituents are each H, a C.sub.1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C.sub.2-4, and wherein Y is a generally anionic counterion and Z is in the range of 0 to 10. Additional, adjunct materials commonly found in liquid cleaning and bleaching compositions can be added.

Liquid compositions containing N-alkyl ammonium acetonitrile salts

Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts.

N-alkyl ammonium acetonitrile bleach activators

Granules are provided that are useful for oxidizing applications when the granules are dissolved in the presence of an active oxygen source. These granules include a salt having the structure of Formula I ##STR1## wherein A is a saturated ring formed by a plurality of atoms in addition to the N.sub.1 atom, the saturated ring atoms including at least one carbon atom and at least one of O, S, and N atoms, the substituent R.sub.1 bound to the N.sub.1 atom of the Formula I structure including either (a) a C.sub.1-24 alkyl or alkoxylated alkyl where the alkoxy is C.sub.2-4, (b) a C.sub.4-24 cycloalkyl, (c) a C.sub.7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C.sub.2-4, or (e) --CR.sub.2 R.sub.3 C.tbd.N where R.sub.2 and R.sub.3 are each H, a C.sub.1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C.sub.2-4, the R.sub.2 and R.sub.3 substituents being each H, a C.sub.1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C.sub.2-4, Z is in the range of 0 to 10, and wherein Y is a counterion. The salt is carried by, coated with, or admixed with a solid particulate such as silica gel, silicic acid, silicate, aluminum oxide, clay, aluminum silicate, or mixtures thereof.

Granular N-alkyl ammonium acetontrile compositions

Bleaching compositions are provided that comprise two nitrile groups where each nitrile is bonded to a quaternary nitrogen through a methylene unit. The quaternary nitrogens are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitriles for bleaching applications.

Dimeric N-Alkyl ammonium acetonitrile bleach activators

Nitrile activators, such as N-alkyl ammonium acetonitrile activators, are combined with a source of active oxygen as cleaning and bleaching compositions. Preferred activator embodiments of the invention include salts of N-methyl morpholinium acetonitrile, N-butyl morpholinium acetonitrile, N-hexyl morpholinium acetonitrile, and N-octyl morpholinium acetonitrile. A particularly preferred activator embodiment is an N-methyl morpholinium acetonitrile salt. The nitrile and active oxygen react to form a bleaching agent which is applied to a stain on an article. The treated stain is contacted with dense gas so as to provide substantially non-aqueous stain removal. One embodiment is a composition in which the nitrile and active oxygen are disposed in the dense carbon dioxide.

N-alkyl ammonium acetonitrile activators in dense gas cleaning and method

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Livermore, CA, United States of America

Kevin A Klotter