Use of oxime esters as activators for inorganic peroxy...

Details Use of oxime esters as activators for inorganic peroxy... Use of oxime esters as activators for inorganic peroxy...

1998-05-04

2001-07-10

Weddington, Kevin E. (Department: 1614)

Compositions

Oxidative bleachant, oxidant containing, or generative

Composition containing a stabilizer or a product in the form...

C252S186400

Reexamination Certificate

active

06258295

ABSTRACT:

The present invention relates to the use of certain mono- and bisoxime esters as activators for inorganic peroxy compounds, in particular as cold bleach activators or optical brighteners in detergents, cleaners and bleaches, and in disinfectants. The present invention furthermore relates to certain industrial formulations which contain these oxime esters.
In efforts concerned with energy-saving washing, cleaning and bleaching processes, recently temperatures in the lower temperature range, for example for textile laundering distinctly below 60° C., in particular below 45° C., have become increasingly important. However, at such temperatures, the effect of the known activators for inorganic peroxy compounds, this system being responsible for the bleaching or cleaning action, showed a distinct decline. This is why there has been no lack of attempts to develop activators which are more effective for this temperature range, but no convincing success has emerged to date.
EP-A 028 432 (1) discloses textile detergent formulations which contain, inter alia, acylated oximes such as acetyloximes, propionyloximes, lauroyloximes, myristoyloximes or benzoyloximes, or corresponding derivatives of dioximes, eg. diacetyldimethylglyoxime or phthaloyldimethylglyoxime.
EP-A 267 046 (2) describes bleach formulations which contain, inter alia, oxime esters, eg. octanoyloxydimethyloxime esters.
It is an object of the present invention to improve the bleaching, oxidizing and cleaning action of a system of activator and inorganic peroxy compounds in the lower temperature range, in particular from 15 to 60° C.
We have found that this object is achieved by using oxime esters of the general formula I
where
L
1
is an oxime moiety of the formula
where
R
1
and R
2
are hydrogen, C
1
-C
30
-alkyl, C
2
-C
30
-alkenyl, C
5
-C
8
-cycloalkyl, C
7
-C
18
-aralkyl or C
6
-C
18
-aryl or -hetaryl, where aliphatic radicals can additionally be functionalized by one to five hydroxyl groups, C
1
-C
4
-alkoxy groups, amino groups, C
1
-C
4
-alkylamino groups, di-C
1
-C
4
-alkylamino groups, chlorine atoms, bromine atoms, nitro groups, cyano groups, carboxyl groups, sulfo groups, carboxy-C
1
-C
4
-alkyl groups, carbamoyl groups or phenyl, tolyl or benzyl radicals, where aromatic, cycloaliphatic and heteroaromatic structural units can likewise be substituted by said radicals, or be interrupted by one to eight non-adjacent oxygen atoms, amino groups, C
1
-C
4
-alkylamino groups or carbonyl groups, and
z
1
is 1,3-, 1,4-, 1,5-, 1,6-, 1,7- or 1,8-alkylene groups with 3 to 30 carbon atoms, which can additionally be functionalized by one to five hydroxyl groups, C
1
-C
4
-alkylamino groups, di-C
1
-C
4
-alkylamino groups, chlorine atoms, bromine atoms, nitro groups, cyano groups, carboxyl groups, sulfo groups, carboxy-C
1
-C
4
-alkyl groups, carbamoyl groups or phenyl, tolyl or benzyl radicals, where aromatic nulcei can in turn likewise be substituted by said radicals, or be interrupted by one or two non-adjacent oxygen atoms, amino groups, C
1
-C
4
-alkylamino groups or carbonyl groups,
L
2
is a second oxime moiety L
1
or
(a) an acyloxy radical of the formula
(b) a carboxamido radical of the formula
(c) a phenoxy radical of the formula
(d) a vinyloxy radical of the formula
—O—CR
1
═CHR
2
(e) a sulfonamido radical of the formula
(f) a n imidazolyl radical of the formula
(g) a hydantoin residue of the formula
(h) a cyclic carbamate residue of the formula
(j) a hydroxylactone residue of the formula
 or
(k) a lactam residue of the formula
 where
R
1
and R
2
have the abovementioned meanings,
R
3
is hydrogen, a carboxyl group, a sulfo group, a phosphono group or the alkali metal or ammonium salt thereof,
T is hydrogen or C
1
-C
4
-alkyl, and
Z
2
to Z
4
are 1,2-, 1,3-, 1,4- or 1,5-alkylene groups with 2 to 20 carbon atoms, which can additionally be functionalized by one to three hydroxyl groups, C
1
-C
4
-alkoxy groups, amino groups, C
1
-C
4
-alkylamino groups, di-C
1
-C
4
-alkylamino groups, chlorine atoms, bromine atoms, nitro groups, cyano groups, carboxyl groups, sulfo groups, carboxy-C
1
-C
4
-alkyl groups, carbamoyl groups or phenyl, tolyl or benzyl radicals, where aromatic nuclei can in turn likewise be substituted by said radicals, or be interrupted by one or two non-adjacent oxygen atoms, amino groups, C
1
-C
4
-alkylamino groups or carbonyl groups,
A is a chemical bond or a C
1
-C
18
-alkylene group, a C
2
-C
18
-alkenylene group, a C
5
-C
32
-cycloalkylene group, a C
7
-C
30
-aralkylene group or a C
6
-C
18
-arylene group or -hetarylene group, where aliphatic structural units can additionally be functionalized by one to five hydroxyl groups, C
1
-C
4
-alkoxy groups, amino groups, C
1
-C
4
-alkylamino groups, di-C
1
-C
4
-alkylamino groups, chlorine atoms, bromine atoms, nitro groups, cyano groups, carboxyl groups, sulfo groups, carboxy-C
1
-C
4
-alkyl groups, carbamoyl groups or phenyl, tolyl or benzyl radicals, where aromatic, cycloaliphatic and heteroaromatic structural units can likewise be substituted by said radicals, or be interrupted by one to eight non-adjacent oxygen atoms, amino groups, C
1
-C
4
-alkylamino groups or carbonyl groups, and
m is 0 or 1,
as activators for inorganic peroxy compounds.
Suitable meanings for the R
1
and R
2
radicals, which can be identical or different, are, besides hydrogen, the following:
examples of suitable linear or branched C
1
-C
30
-alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl or n-eicosyl; C
1
-C
12
-alkyl groups are preferred, especially C
1
-C
4
-alkyl groups;
examples of suitable linear or branched C
2
-C
30
-alkenyl groups are vinyl, allyl, 2-methyl-2-propenyl or the appropriate radicals derived from oleic acid, linoleic acid or linolenic acid; C
2
-C
6
-alkenyl and C
16
-C
22
-alkenyl groups are preferred;
particularly suitable C
5
-C
1
-cycloalkyl groups are C
5
-C
10
-cycloalkyl groups, eg. cyclopentyl, cyclohexyl, 2-, 3- or 4-methylcyclohexyl, 2,3-, 2,4-, 2,5- or 2,6-dimethylcyclohexyl, cycloheptyl or cyclooctyl;
particularly suitable C
7
-C
18
-aralkyl, especially C
7
-C
12
-aralkyl, groups are alkyl-substituted phenylalkyl groups, eg. benzyl, 2-, 3- or 4-methylbenzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 2-, 3- or 4-ethylbenzyl, 3- or 4-isopropylbenzyl or 3- or 4-butylbenzyl;
examples of suitable C
6
-C
18
-aryl groups are phenyl, 2-, 3- or 4-biphenylyl, &agr;- or &bgr;-naphthyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 3- or 4-isopropylphenyl, 3- or 4-butylphenyl or 3- or 4-(2-ethylhexyl)phenyl; C
6
-C
14
-aryl groups are preferred, especially phenyl and alkyl-substituted phenyl;
particularly suitable C
6
-C
18
-hetaryl groups are five- or six-membered C
6
-C
12
-hetaryl groups with one or two heteroatoms from the group of nitrogen, oxygen and sulfur, and examples thereof are:
examples of suitable aliphatic radicals interrupted by oxygen or amino groups, especially NH or N(CH
3
) groups are the following structures:
with p=2 to 8 and q=2 to 5.
The variable Z
1
in the cyclic oxime moieties L
1
can be, in particular, C
3
-C
12
-alkylene groups of the following structure:
where the variable Z
1
can be functionalized or interrupted as stated.
The variables z
2
to Z
4
in the heterocyclic systems (h), (j) and 5 (k) can be, in particular, C
2
-C
10
-alkylene groups of the following structure:
where in the case of asymmetrical alkylene groups both possibilities of incorporation into the rings are possible in principle. The variables Z
2
to Z
4
can be functionalized or interrupted as stated.
Particularly suitable acyloxy radicals (a) for L
2
are:
Particularly suitable carboxamido radicals (a) for L
2
are:
Particularly suitable phenoxy radicals (c) for L
2
are:
and the relevant sodium or potassium salts.
Particularly suitable vi

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