Process for treating textile materials

Details Process for treating textile materials Process for treating textile materials

2001-04-13

2002-07-02

Del Cotto, Gregory (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

For cleaning a specific substrate or removing a specific...

C510S372000, C510S376000, C252S186330, C502S167000, C502S200000, C502S324000

Reexamination Certificate

active

06413926

ABSTRACT:

The present invention relates to a process for preventing the redeposition of migrating dyes in wash liquors comprising a peroxide and a manganese catalyst, to manganese catalysts suitable for the process, and to detergent formulations comprising these catalysts.
It is already known that some manganese complexes of the salen type are suitable catalysts for oxidations with peroxygen compounds, especially as part of a washing process. The salen complexes involved are exclusively symmetrical. It has also been described before that certain other manganese complexes possess a pronounced bleaching effect on dirt and dyes in wash liquors.
It has now been found that certain asymmetric manganese complexes of the salen type exhibit a much greater specific action as catalysts for preventing the redispositon of migrating dyes in wash liquors without notably damaging either dye or fibre. Complexes are termed asymmetric when they come about through the reaction of 2 mol of two differently modified salicylaldehydes or o-hydroxyphenyl ketones with 1 mol of ethylenediamine or another modified diamine building block and so possess two differently substituted aromatic radicals.
The present invention therefore provides a process for preventing the redeposition of migrating dyes in a wash liquor, which comprises adding to the wash liquor, which comprises a peroxide-containing detergent, from 0.5 to 150 mg, preferably from 1.5 to 75 mg and, in particular, from 7.5 to 40 mg per liter of wash liquor of one or more compounds of the formula
in which
n is 0, 1, 2 or 3,
m is 1, 2 or 3,
A is an anion;
Y is a linear or branched alkylene radical of the formula —[C(R
5
)
2
]
r
—, where r is an integer from 1 to 8 and the R
5
radicals independently of one another are hydrogen or C
1
-C
4
alkyl;
—CX═CX—, in which X is cyano, linear or branched C
1
-C
8
alkyl or di(linear or branched C
1
-C
8
alkyl)-amino,
—(CH
2
)
q
—NR
4
—(CH
2
)
q
—, in which R
4
is hydrogen or linear or branched C
1
-C
4
alkyl and q is 1, 2, 3 or 4; or
a 1,2-cyclohexylene radical of the formula:
or a 1,2-aryl radical of the formula
in which
R
9
is SO
3
H, CH
2
OH or CH
2
NH
2
,
R and R
1
independently of one another are cyano, halogen, OR
5
or COOR
5
, in which R
5
is hydrogen or linear or branched C
1
-C
4
alkyl, or are nitro, linear or branched C
1
-C
8
alkyl, linear or branched, partially fluorinated or perfluorinated C
1
-C
8
alkyl, NHR
6
or NR
6
R
7
in which R
6
and R
7
are identical or different and are each linear or branched C
1
-C
12
alkyl or in which R
6
and R
7
, together with the nitrogen atom connecting them, form a 5-, 6- or 7-membered ring which may include further heteroatoms, or are linear or branched C
1
-C
8
alkyl-R
8
, in which R
8
is a radical OR
5,
COOR
5
or NR
6
R
7
with the above definitions or is NH
2
, or are —N
⊕
R
4
R
6
R
7
, in which R
4,
R
6
and R
7
are as defined above,
R
2
and R
3
independently of one another are hydrogen, linear or branched C
1
-C
4
alkyl or unsubstituted aryl, or aryl substituted by cyano, halogen, OR
5
or COOR
5
, in which R
5
is hydrogen or linear or branched C
1
-C
4
alkyl, or by nitro, linear or branched C
1
-C
8
alkyl, NHR
6
or NR
6
R
7
in which R
6
and R
7
are identical or different and are as defined above, or by linear or branched C
1
-C
8
alkyl-R
8
, in which R
8
is a radical OR
5
, COOR
5
or NR
6
R
7
with the above definitions or is NH
2
, or by —N
⊕
R
4
R
6
R
7
, in which R
4,
R
6
and R
7
are as defined above, with the proviso that R and R
1
do not have the same definition if n and m are identical.
In the compounds of the formula (1) in which n is 2 or 3 the radicals R can have the same or different definitions. With respect to the radicals R
1
the same applies to compounds of the formula (1) in which m is 2 or 3.
Where Y is a 1,2-cyclohexylene radical it may be present in each of its stereoisomeric cis/trans forms.
Preferably Y is a radical of the formula —(CH
2
)
r
—, where r is an integer from 1 to 8, or of the formula —C(R
5
)
2
—(CH
2
)
p
—C(R
5
)
2
— in which p is a number from 0 to 6 and R
5
is hydrogen or C
1
-C
4
alkyl.
In particularly preferred compounds of the formula (1) Y is a radical of the formula —(CH
2
)
r
—, where r is an integer from 1 to 4, or of the formula —(CR
5
)
2
—(CR
5
)
2
—, in which R
5
independently at each occurrence is hydrogen or methyl.
Halogen is preferably chlorine, bromine or fluorine, with particular preference being given to chlorine.
If n or m is 1 the groups R and R
1
are preferably in position 4 of the respective benzene ring except when R or R
1
, respectively, is nitro or COOR
5
. In this case the group R or R
1
, respectively, is preferably in position 5.
If n or m is 2 the two R groups or R
1
groups are preferably in positions 4 and 6 of the respective benzene ring except when R or R
1
, respectively, is nitro or COOR
5
. In this case the two R groups or R
1
groups, respectively, are preferably in positions 3 and 5.
If R or R
1
is di(C
1
-C
12
alkyl)amino the alkyl group can be straight-chain or branched. It preferably contains from 1 to 8, in particular from 1 to 4 and, especially, 1 or 2 carbon atoms.
The radicals R and R
1
are preferably hydrogen, nitro, OR
5,
COOR
5
or N(R
5
)
2
, with R
5
being hydrogen or C
1
-C
4
alkyl, especially methyl or ethyl.
The radicals R
2
and R
3
are especially hydrogen, methyl, ethyl or unsubstituted phenyl.
Aryl is, for example, naphthyl or especially phenyl.
If R
6
and R
7
together with the nitrogen atom connecting them form a 5-, 6- or 7-membered ring this ring is especially a pyrrolidine, piperidine, morpholine or piperazine ring. The piperazine ring can be substituted, by alkyl, for example, on the nitrogen atom that is not joined to the phenyl radical.
Examples of suitable anions are halide, such as chloride, perchlorate, sulfate, nitrate, hydroxide, BF
4
−
, PF
6
−
, carboxylate, acetate, tosylate and triflate. Preference among these is given to chloride, acetate and carboxylate.
The present invention also provides the compounds of the formula
in which
n is 0, 1, 2 or 3,
m is 1, 2 or 3,
A is an anion;
Y is a linear or branched alkylene radical of the formula —[C(R
5
)
2
]
r
—, where r is an integer from 1 to 8 and the R
5
radicals independently of one another are hydrogen or C
1
-C
4
alkyl;
—CX═CX—, in which X is cyano, linear or branched C
1
-C
8
alkyl or di(linear or branched C
1
-C
8
alkyl)-amino,
—(CH
2
)
q
—NR
4
—(CH
2
)
q
—, in which R
4
is as defined above and q is 1, 2, 3 or 4; or
a 1,2-cyclohexylene radical of the formula:
or a 1,2-aryl radical of the formula
in which R
9
is SO
3
H, CH
2
OH or CH
2
NH
2
,
R and R
1
independently of one another are cyano, halogen, OR
5
or COOR
5
, in which R
5
is hydrogen or linear or branched C
1
-C
4
alkyl, or are nitro, linear or branched C
1
-C
8
alkyl, linear or branched, partially fluorinated or perfluorinated C
1
-C
8
alkyl, NHR
6
or NR
6
R
7
in which R
6
and R
7
are identical or different and are each linear or branched C
1
-C
12
alkyl or in which R
6
and R
7
, together with the nitrogen atom connecting them, form a 5-, 6- or 7-membered ring which may include further heteroatoms, or are linear or branched C
1
-C
8
alkyl-R
8
, in which R
8
is a radical OR
5
, COOR
5
or NR
6
R
7
with the above definitions or is NH
2
, or are —N
⊕
R
4
R
6
R
7
, in which R
4,
R
6
and R
7
are as defined above,
R
2
and R
3
independently of one another are hydrogen, linear or branched C
1
-C
4
alkyl or unsubstituted aryl, or aryl substituted by cyano, halogen, OR
5
or COOR
5
, in which R
5
is hydrogen or linear or branched C
1
-C
4
alkyl, or by nitro, linear or branched C
1
-C
8
alkyl, NHR
6
or NR
6
R
7
in which R
6
and R
7
are identical or different and are each linear or branched C
1
-C
12
alkyl, or in which R
6
and R
7
, together with the nitrogen atom connecting them, form a 5-,6- or 7-membered ring which may include further heteroatoms, or by linear or branched C
1
-C
8
alkyl-R
8
, in which R
8
is a radical OR
5
, COOR
5
o

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