Peroxyacids

Details Peroxyacids Peroxyacids

1993-07-13

2004-04-27

Achutamurthy, Ponnathapu (Department: 1652)

Organic compounds -- part of the class 532-570 series

Organic compounds

Percarboxylic acids or salts thereof

C562S004000, C510S310000, C510S375000, C252S186420

Reexamination Certificate

active

06727382

ABSTRACT:

This invention relates to cationic peroxyacids and to bleaching and detergent compositions comprising said peroxyacids.
Cationic peroxyacids are known in the art. The use of such materials as bleaching additives in detergent compositions has also been described previously.
For example, Japanese Patent Application 1056797 (Kao) is concerned with a bleaching detergent composition comprising peroxyacids of formula (I)
wherein:
R
1
is a, optionally substituted, C
1
-C
24
alkyl or alkenyl or alkaryl with a C
1
-C
24
alkyl group;
R
2
and R
3
are a C
1
-C
3
alkyl, hydroxyalkyl, —(C
2
H
4
O)
1-5
H or —Y—CO—O—O—H; and
Y is a, substituted or unsubstituted linear or branched, C
1
-C
20
alkylene. Not only does this reference fail to disclose how these materials are prepared but it also states the peroxyacids are not stable.
European Patent Specification 316 809 (Ausimont) is concerned with salts of peroxyacids. In particular, it is concerned with cationic peroxyacids having the general formula (II):
wherein:
R, R
1
and R
2
are each independently hydrogen; a, optionally substituted alkyl or two of said R, R
1
and R
2
are combined to form a, optionally substituted, aliphatic or heterocylic ring with the nitrogen atom to which they are attached;
A is selected from, optionally substituted, alkylene, cycloalkylene, arylene, cycloalkylene-alkylene, alkylene-cycloalkylene, arylene-alkylene or alkylene-arylene, said cycloalkylene or arylene units of the above groups being optionally fused with one or more cycloaliphatic groups and said alkylene units optionally having interspersed CONR
3
groups wherein R
3
is hydrogen, alkyl or aryl; and
X represents HSO
4
, or CH
3
SO
3
; and
n is an integer of from 1 to 6, preferably 1 or 2.
This reference also describes the use of these peroxyacids in detergent formulations.
The disadvantage of the materials exemplified in the examples of EP 316 809 is that, with the exception of example 3, they are formed by protonation of the appropriate amino acid in acid solution. In bleaching medium, that is normal washing conditions where the pH of the solution is in the range of from 9 to 10, the cationic aminoperoxyacids, which typically have a pKa in the range of 9.5 to 10.5, will tend to, at least partially, deprotonate leaving a non-cationic species. Such species are known to be less active, in terms of bleaching efficiency, than their cationic counterparts. Thus, the peroxyacids exemplified in this reference would not be expected to show the same high activity as their cationic counterparts. Furthermore, solutions of these materials are unstable and prone to self-destruction.
Similarly the material described in example 3 of EP-316 809, trimethyl ammonium (carboxymethyl) hydroxide (betaine monohydrate), is known to be unstable because of the close proximity of the N
+
and CO
3
H groups in the molecule. Thus, it would not have adequate solution stability required for many industrial applications.
The present invention seeks to overcome the disadvantages associated with these known peroxyacids.
Japanese Patent Application 4-91075 is an example of a further reference which is concerned with peroxyacids. In particular, it is concerned with overcoming the problem of crystallising, in aqueous systems, salts of organic peracids which contain quaternary ammonium groups. This is achieved by forming specific sulphonic acid salts of the peracids formula (III):
where R
1
is a substituted or unsubstituted linear or branched C
1-20
alkyl or alkenyl group or an unsubstituted or C
1-20
alkyl-substituted aryl group, X is
Y is
where l is an integer from 1 to 10, R
2
is a substituted or unsubstituted C
1-10
alkyl group, R
3
is a substituted or unsubstituted C
1-3
alkyl group, R
4
and R
6
are substituted or unsubstituted alkylene groups,
where k and h are integers from 0 to 3 and l is as defined above and Z is an anion of formula R
5
(O)
p
SO
3
−
, where R
5
is a C
2-20
alkyl group, alkenyl group, or alkyl-substituted or unsubstituted aryl group, and m, n, and p are 0 to 1. Of the materials exemplified, a C
8
material is the lowest alkyl chain length material. Such materials suffer from adverse interactions with soil and surfactants present in a wash liquor with a resulting reduction in performance of the peroxyacid.
We have now found that when peroxyacids of formula (III) with selected quaternary ammonium groups and anions are incorporated in detergent compositions cleaning performance on soil stains is improved.
Accordingly, the present invention provides cationic peroxyacids of formula (IV)
wherein:
R
1
is a C
1
-C
7
alkyl or alkenyl or alkaryl with a C
1
-C
7
alkyl group;
R
2
and R
3
are each independently a C
1
-C
3
alkyl group;
n is an integer from 0 to 3; and
X
−
is a surfactant anion selected from alkyl carboxylates; alkyl ether sulphates; alkylbenzene sulphonates; C
12-15
primary and C
14-18
secondary alkyl sulphates; olefin sulphonates; alkane sulphonates; dialkyl sulphosuccinates; fatty acid ester sulphonates; alkylether sulphonates, alkylether carboxylates, sulphonated alkyl polyglycosides; sulphonated alkanoyl glucose ethers, sulphonated monoglycerol ethers; secondary alkane sulphonates; esterified isethionates, alkyl and dialkyl phosphates; sodium fatty acid sulphonates; and fatty acid soaps.
Particularly preferred cationic peroxyacids materials are those in which R
1
is C
4
-C
7
alkyl or benzyl. When R
1
is C
8
or more antagonistic effects with soil and/or surfactants can result in a reduction in performance of the peroxyacid in a washing liquor. When R
1
is less than C
4
, although good performance is maintained, it is possible that in a washing liquor high local concentration of the peroxyacid may come into contact with fabric with a risk of local dye damage.
Preferably, the —CO
3
H group is in meta, most preferably para, position with respect to the (CH
2
)
n
group, if present, or the quaternary ammonium group.
Preferred surfactant anions are sodium C
12-15
primary alcohol sulphates for example dodecyl sulphate, SDS; and linear alkyl benzene sulphonates; and secondary alkyl sulphates.
The surfactant anion may be introduced during the synthesis of the cationic peroxyacid. Alternatively, peroxyacids can be prepared with other anions such as methane sulphonate or tosylate and the surfactant anion introduced by means of exchange. It will be appreciated that peroxyacids of the invention may be formed in situ in a washing liquor by reaction of a peroxyacid having, for example, a methanesulphonate anion with anionic surface-active materials present as part of a detergent composition.
Cationic peroxyacids of the invention may exist in form of different solvates ie. may contain solvents trapped or incorporated within the crystal structure of the peroxyacid depending on the method preparation.
The cationic peroxyacids of the present invention may readily be prepared by reaction of an appropriate amino benzoic acid to form an amine salt, optionally followed by reaction to protect the carboxylic acid, and finally quaternisation and peroxidation. This route is much simpler than the route described in Japanese Patent Application 4-91075.
A route for preparing the cationic peroxyacids of the present invention comprises the steps of:
i) derivatising the starting material to form a distillable intermediate,
ii) distilling the intermediate of step (i) and
iii) effecting peroxidation of the distilled intermediate of step (ii) or a derivative thereof in the presence of distilled reaction solvent.
Preferably the starting material is an amino benzoic acid, such as
The acid is esterified, most preferably via the formation of an amine salt, to form an amino ester. The amino ester is distilled and the resulting material quaternised and peroxidised in the presence of a distilled reaction solvent. A particularly preferred reaction solvent is methane sulphonic, acid.
The aforementioned route, which involves the use of a distilled material and distilled reaction solvent, is particularly preferred.
An advantage of the cationic per

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