# US 2002/0165110 A1 · Use of transition metal complexes having oxime ligands as bleach catalysts

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- Number: US 2002/0165110 A1
- Document ID: US20020165110A1
- Status: Published application
- Kind: A1
- Application number: 10/052,123
- Filed: 2002-01-17
- Published: 2002-11-07
- Earliest claimed: 2001-01-19
- Assignees: Clariant GmbH
- Inventors: Gerd Reinhardt; Michael Seebach; Nicole Reichardt; Laszlo I. Simandi; Tatiana M. Simandi; Gabor Besenyei
- Web page: https://patentgrep.com/patent/US20020165110A1

## CPC

- C11D 3/3932: {Inorganic compounds or complexes}
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

Transition metal complexes used as bleach catalysts of the formula (1) M(L)nXm (1) where M is a metal atom from the group Mn, Fe, Co, Ni, Mo, W, L is a ligand of the formula R1 R2C═N—O(H)z R1 is C1-C22-alkyl, C2-C22-alkenyl or C5-C24-aryl, R2 is H, C1-C22-alkyl, C2-C22-alkenyl, C5-C24-aryl or 1 where z=0 or 1, X is a neutral or anion ligand from the group consisting of pyridines, imidazolines, methylimidazoles, picolines, lutidines, chloride, bromide, nitrate, perchlorate, citrate, hexafluorophosphate or anions of organic acids having C1-C22 carbon atoms, n is a number from 2 to 4 and m is a number from 0 to 4.

## Claims

### Claim 1

A process for increasing the bleaching action of peroxygen compounds comprising combining a transition metal complex having oxime ligands as a bleach catalyst with the peroxygen compounds, wherein the transition metal complex has the formula (1)
M(L)nXm (1)
where
M is a metal atom selected from the group consisting of Mn, Fe, Co, Ni, Mo, and W,
L is the oxime ligand of the formula
R1R2C═N—O(H)z
R1 is C1-C22-alkyl, C2-C22-alkenyl or C5-C24-aryl,
R2 is H, C1-C22-alkyl, C2-C22-alkenyl, C5-C24-aryl or
6
where z=0 or 1,
X is a neutral or anion ligand selected from the group consisting of pyridines, imidazolines, methylimidazoles, picolines, lutidines, chloride, bromide, nitrate, perchlorate, citrate, hexafluorophosphate, and anions of organic acids having C1-C22 carbon atoms, n is a number from 2 to 4 and m is a number from 0 to 4.

### Claim 2 (depends on 1)

The process of claim 1, wherein the peroxygen compound is selected from the group consisting of organic peracids, hydrogen peroxide, perborate and percarbonate, and mixtures thereof.

### Claim 3 (depends on 1)

The process of claim 1 further comprising incorporating the transition metal complex and peroxygen compounds into a cleaning composition.

### Claim 4 (depends on 3)

The process of claim 3 wherein the cleaning composition comprises from 0.0025 to 1 weight percent of the transition metal complex.

### Claim 5 (depends on 3)

The process of claim 3 wherein the cleaning composition comprises 0.01 to 0.1 weight percent of the transition metal complex.

### Claim 6 (depends on 3)

The process of claim 3 further comprising combining the cleaning composition in an aqueous solution to provide a textile washing product or to provide a hard surface cleaning product.

### Claim 7 (depends on 3)

The process of claim 3 further comprising combining the cleaning composition with an aqueous solution to provide a bleaching compound for colored soilings.

### Claim 8

A process for increasing the bleaching action of a peroxygen compound comprising combining a transition metal complex having oxime ligands as a bleach catalyst with a bleach activator, wherein the transition metal complex has the formula (1)
M(L)nXm (1)
where
M is a metal atom selected from the group consisting of Mn, Fe, Co, Ni, Mo, and W,
L is the oxime ligand of the formula
R1 R2C═N—O(H)z
R1 is C1-C22-alkyl, C2-C22-alkenyl or C5-C24-aryl,
R2 is H, C1-C22-alkyl, C2-C22-alkenyl, C5-C24-aryl or
7
where z=0 or 1,
X is a neutral or anion ligand selected from the group consisting of pyridines, imidazolines, methylimidazoles, picolines, lutidines, chloride, bromide, nitrate, perchlorate, citrate, hexafluorophosphate , and anions of organic acids having C1-C22 carbon atoms, n is a number from 2 to 4, and m is a number from 0 to 4.

### Claim 9 (depends on 8)

The process of claim 8 wherein the bleach activator is selected from the group consisting of polyacylated alkylenediamines, acylated glycolurils, acylated trizine derivatives, acylated phenylsulfonates, acylated polyhydric alcohols, acylated sugar derivatives, and open-chain or cyclic nitrile quats.

### Claim 10

A transition metal complex of the formula (1)
Mn(L)nXm (1)
where
M is a metal atom selected from the group consisting of Mn, Fe, Co, Ni, Mo, and W,
L is a ligand of the formula
R1R2C═N—O(H)z
R1 is C1-C22-alkyl, C2-C22-alkenyl or C5-C24-aryl,
R2 is H, C1-C22-alkyl, C2-C22-alkenyl, C5-C24-aryl or
8
where z=0 or 1,
X is a neutral or anion ligand selected from the group consisting of pyridines, imidazolines, methylimidazoles, picolines, lutidines, chloride, bromide, nitrate, perchlorate, citrate, hexafluorophosphate, and anions of organic acids having C1-C22 carbon atoms, n is a number from 2 to 4, and m is a number from 0 to 4.

### Claim 11 (depends on 10)

A cleaning composition comprising the transition metal complex as in claim 10.

### Claim 12 (depends on 11)

The cleaning composition as claimed in claim 11, which comprises 0.0025% by weight to 1% by weight of the transition metal complex.

### Claim 13 (depends on 11)

The cleaning composition as claimed in claim 11, which comprises 0.01% by weight to 0.1% by weight of the transition metal complex.

### Claim 14 (depends on 11)

The cleaning composition as claimed in claim 11, which, in addition to the transition metal complex, comprises from 1% to 10% by weight of a bleach activator.

### Claim 15 (depends on 11)

The cleaning composition as claimed in claim 11, which, in addition to the transition metal complex, comprises from 2% to 6% by weight, of a bleach activator.

### Claim 16 (depends on 11)

The cleaning composition of claim 11 wherein the transition metal complex comprises
c) [bis(cyclohexanone oxime)bis(cyclohexanone oximato)bis(pyridine)-manganese(II)], or
d) [bis(diphenylglyoximato)bis(pyridine)manganese(II)]