Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – With oxygen or halogen containing chemical bleach or oxidant...
Reexamination Certificate
1999-08-04
2002-06-25
Boyer, Charles (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
With oxygen or halogen containing chemical bleach or oxidant...
C510S276000, C510S286000, C510S302000, C510S311000, C510S312000, C510S313000, C510S314000, C510S367000
Reexamination Certificate
active
06410497
ABSTRACT:
The invention relates to the use of carbonates, such as oxime carbonates and hydroxyimide carbonates, hydroxyimide esters and polymers thereof, as activators for inorganic per compounds, and to detergent formulations comprising them.
The use of particular hydroxyimide esters as bleach activators is known. EP-A-0 267 046 describes bleach compositions which comprise peracid precursors. Compounds cited include N-hydroxyimides, for example N-hydroxysuccinimide, N-hydroxyphthalimide, N-hydroxyglutarimide, N-hydroxynaphthalimide, N-hydroxymaleimide, N-hydroxydiacetylimide and N-hydroxydipropionylimide. These N-hydroxyimides are used in the form of esters with carboxylic acids, especially with octanoic acid. Use is also made of oxime esters which are formed from oximes of aldehydes or ketones with carboxylic acids, especially octanoic acid. Of these, preferred oximes are acetone oxime and methyl ethyl ketoxime.
It is an object of the present invention to provide further activators for inorganic per compounds which have an improved action especially in the case of hydrophobic bleaching.
We have found that this object is achieved by the use of carbonates of the formula (I)
A—O—CO—OR
3
(I)
where
A is a radical (Ia)
R
1
R
2
C═N— (Ia)
or A is a radical (Ib)
where R
1
, R
2
, R
3
, R
4
and R
5
independently are straight-chain or branched C
1-30
-alkyl, C
2-30
-alkenyl, C
5-18
-cycloalkyl, C
7-18
-aralkyl or C
6-18
-aryl or -heteroaryl, it being possible for aliphatic radicals to be functionalized additionally by 1 to 5 hydroxyl, C
1-4
-alkoxy, amino, C
1-4
-alkylamino, di-C
1-4
-alkylamino, nitro, cyano, carboxyl, sulfo, carboxy-
1-4
-alkyl or carboxamide groups, chlorine or bromine atoms or by phenyl, tolyl or benzyl, it likewise being possible for aromatic, cycloaliphatic and heteroaromatic structural units to be substituted by these functions or to be interrupted by 1 to 8 nonadjacent oxygens or amino, C
1-4
-alkylamino or carbonyl groups, and
R
1
and R
2
, furthermore, can be hydrogen or together form a 1,3-, 1,4-, 1,5-, 1,6-, 1,7- or 1,8-alkylene group of 3 to 33 C atoms which can be functionalized additionally by 1 to 5 hydroxyl, C
1-4
-alkylamino, di-C
1-4
-alkylamino, nitro, cyano, carboxyl, sulfo, carboxy-C
1-4
-alkyl or carboxamide groups, chlorine or bromine atoms or phenyl, tolyl or benzyl, and where aromatic radicals in turn can likewise be substituted by these functions, or can be interrupted by one or two nonadjacent oxygens or amino, C
1-4
-alkylamino or carbonyl groups,
and, if A is a radical (Ia), R
3
is not a vinyl which can be substituted by a carboxylic, sulfonic or phosphonic acid group or an alkali metal salt or ammonium salt thereof and is not a vinyloxy radical —O—CR
1
═CHR
2
in which R
1
and R
2
are as defined above,
and R
3
can be a radical (Ib) if A is a radical (Ib), especially if R
4
and R
5
together form a 1,2-phenylene ring (phthalimide derivative) or 1,2-ethylene ring (succinimide derivative),
and R
4
and R
5
, furthermore, can together form a 1,2-, 1,3-, 1,4-, 1,5- or 1,6-alkylene group of 2 to 30 C atoms, which can be substituted like the above alkylene groups, or
R
4
and R
5
together form a 5-, 6-, 7-, 8- or 9-membered carbon ring which is attached to the carbonyl groups by way of 2 adjacent C atoms, where one or more double bonds can be present in the ring or the ring can be aromatically unsaturated and where one or more C atoms in the ring can be replaced by heteroatoms, and 2 C atoms in the ring can be attached via a heteroatom or a C
1-3
-alkylene or C
2-3
-alkenylene radical, or
R
4
and R
5
can form the above carbon ring from 2 carbonate molecules together, which ring is attached to the carbonyl groups of the two imide structures by way of in each case two adjacent C atoms (see for example the tricyclic diimide structures of the formula VI below), or hydroxyimide esters of the formula (II)
where R
3
is as defined above and R
6
and R
7
together form a 5-, 6-, 7-, 8- or 9-membered carbon ring which is attached to the carbonyl groups via two adjacent C atoms, where one or more double bonds can be present in the ring, one or more ring positions can be replaced by heteroatoms, and 2 C atoms in the ring can be connected via a heteroatom and a C
1-3
-alkylene or C
2-3
-alkenylene radical which is attached to the carbonyl groups of the two imide structures by in each case 2 adjacent C atoms,
or R
6
and R
7
can form the above carbon ring from 2 hydroxyimide ester molecules together, which ring is attached to the carbonyl groups of the two imide structures via in each case two adjacent C atoms (see for example the tricyclic diimide structures of the formula VI below),
or polymers which can comprise C
2-8
, olefin comonomer units and comprise base units of the formulae (III), (IV) and/or (V)
where R
8
is a radical R
3
or —OR
3
with the abovementioned definition
as activators for inorganic per compounds.
The activators according to the invention can be used in detergents, cleaning products, bleaches and disinfectants, for example as cold bleach activators.
According to one embodiment of the invention the compounds are oxime carbonates, if A is a radical (Ia) R
1
R
2
C═N—. In this case R
1
and R
2
, in addition to hydrogen, are, for example, linear or branched C
1-30
-alkyls, such as 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. Preferred alkyls are C
1-12
-alkyls, especially C
1-4
-alkyls; in particular, R
1
and R
2
are ethyl groups.
The radicals R
1
and R
2
can also be linear or branched C
2-30
-alkenyls, such as vinyl, allyl or 2-methylprop-2-enyl, or radicals derived from oleic, linoleic or linolenic acid. Preference is given to C
2-6
-alkenyl and to C
6-22
-alkenyl radicals.
It is also possible to use C
5-18
-cycloalkyl radicals, preferably C
5-10
-cycloalkyl radicals, such as cyclopentyl, cyclohexyl, 2-, 3- or 4-methylcyclohexyl, 2,3-, 2,4-, 2,5- or 2,6-dimethylcyclohexyl, cycloheptyl or cyclooctyl.
Other radicals that can be used are C
7-18
-aralkyl radicals, preferably C
7-12
-aralkyl radicals, especially alkyl-substituted phenyl radicals such as 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
6-18
-aryl groups are phenyl, 2-, 3- or 4-biphenylyl, alpha- or beta-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. Of these, preference is given to C
6-14
-aryl radicals, especially phenyls and alkyl-substituted phenyls.
C
6-18
-heteroaryl radicals are preferably 5- or 6-membered C
6-12
-heteroaryl radicals having one or two heteroatoms from the group consisting of nitrogen, oxygen and sulfur. Examples of suitable heterocycles are pyridine, furan, thiophene, pyrrole, imidazole, pyrazole, thiazole, pyrazine and pyrimidine. These radicals can be attached by any one of the ring carbons. Furthermore, the ring structures can be substituted at the carbons which have free valences, preferably by C
1-4
-alkyl radicals such as the abovementioned methyl, ethyl, propyl and butyl radicals.
Examples of aliphatic radicals interrupted by oxygen or amino groups, especially NH or N(CH
3
) groups, that can be employed are methylethylaminoethyl, dimethylaminomethyl, methoxymethyl, methoxyethyl, ethoxyethyl, hydroxyethyl, reacted with 1 to 8 ethylene oxide units, methoxybutyl, methoxypropyl, 2-methoxy-l-methylethyl and 2-hydroxy-1-methylethyl, reacted with 1 to 5 propylene oxide units.
R
1
and R
2
can together preferably form a C
3-12
-alkylene radical. Examples are propylene radicals which are substituted in position 1, 2 or 3 by methyl, ethyl, propyl or butyl groups, butylene radicals which can be substituted in positions 1, 2, 1,
Boeckh Dieter
Kappes Elisabeth
Oftring Alfred
Wehlage Thomas
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