Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Heat drying process – or product thereof
Reexamination Certificate
2004-03-11
2004-11-30
Del Cotto, Gregory R. (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
Heat drying process, or product thereof
C510S311000, C510S376000, C510S446000, C502S200000, C502S324000
Reexamination Certificate
active
06825162
ABSTRACT:
The present invention relates to a process for the preparation of water-soluble granules or particles of saldimine-type manganese complexes and a polymeric dissolution restrainer and to the use thereof as dye-transfer inhibitors in washing agent preparations.
A number of saldimine-type manganese complexes (or salen-type manganese complexes) are already known to be suitable catalysts for oxidations with peroxy compounds, especially within the context of washing procedures. The use of certain manganese complexes as catalysts for preventing the redeposition of migrating dyes in peroxide-containing washing liquors is described for example in EP 902 083, but the action of those manganese complexes as dye-transfer inhibitors is not optimum under all washing conditions. A further problem is that the peroxy compound and/or the catalyst in the washing agent formulation decompose(s) during prolonged storage in a moist atmosphere.
Surprisingly, it has now been found that granules or particles comprising a saldimine-type manganese complex and at least 10% by weight of a polymeric dissolution restrainer which are prepared according to the inventive process provide better inhibition of the redeposition of migrating dyes in washing liquors than is provided by the pure manganese complexes when the total amount of manganese complex entering into the washing liquor is the same in both cases. A further advantage of the granules or particles is that the storage stability of peroxide-containing washing agent formulations comprising such granules or particles is improved. In addition, these granules or particles inhibit undesired colouration of the washing agent as a result of the gradual dissolution of the manganese complexes in one or more of the washing agent components.
The present invention accordingly relates to a process for the preparation of water-soluble granules or particles of saldimine-type manganese complexes and a polymeric dissolution restrainer, comprising
a) mixing the polymeric material with water and subsequently dissolving/suspending the saldimine-type manganese complex in it to form an aqueous polymer phase containing the saldimine-type manganese complex substantially uniformly distributed throughout the phase,
b) simultaneously or subsequently dispersing the aqueous phase in a water immiscible liquid in the presence of a dispersion stabiliser to form a substantially stable dispersion, and
c) azeotroping the dispersion
to form substantially dry particles each comprising a matrix of the polymeric material with the saldimine-type manganese complex dispersed substantially uniformly throughout the matrix.
As manganese complexes for the granules or particles according to the invention there come into consideration compounds that contain, complexed with manganese, from 1 to 3 saldimine groups, that is to say, groups obtainable by condensing unsubstituted or substituted salicylaldehydes with amines.
Especially suitable are compounds of formula
wherein
A is an anion;
m, n and p are each independently of the others 0, 1, 2 or 3,
R
4
is hydrogen or linear or branched C
1
-C
4
alkyl,
Y is a linear or branched alkylene radical of formula —[C(R
4
)
2
]
r
—, wherein r is an integer from 1 to 8 and the R
4
radicals are each independently of the others as defined above;
—CX═CX—, wherein 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
—, wherein R
4
is as defined above and q is 1, 2, 3 or 4; or
a 1,2-cyclohexylene radical of formula:
or a 1,2-aryl radical of formula
wherein R
9
is hydrogen, SO
3
H, CH
2
OH or CH
2
NH
2
,
R, R
1
and R
1
′ are each independently of the others cyano; halogen; OR
4
or COOR
4
wherein R
4
is as defined above; nitro; linear or branched C
1
-C
8
alkyl; linear or branched partially fluorinated or perfluorinated C
1
-C
8
alkyl; or NHR
6
, NR
5
R
6
or N
⊕
R
5
R
6
R
7
wherein R
5
, R
6
and R
7
are the same or different and are each hydrogen or linear or branched C
1
-C
12
alkyl or wherein R
5
and R
6
together with the nitrogen atom to which they are bonded form a 5-, 6- or 7-membered ring, which may contain further hetero atoms, or are linear or branched C
1
-C
8
alkyl-R
8
wherein R
8
is a radical OR
4
, COOR
4
or NR
5
R
6
as defined above or is NH
2
or N
⊕
R
5
R
6
R
7
wherein R
5
, R
6
and R
7
are as defined above,
R
2
and R
3
are each independently of the other hydrogen, linear or branched C
1
-C
4
alkyl, unsubstituted aryl or aryl that is substituted by cyano, by halogen, by OR
4
or COOR
4
wherein R
4
is hydrogen or linear or branched C
1
-C
4
alkyl, by nitro, by linear or branched C
1
-C
8
alkyl, by NHR
5
or NR
5
R
6
, wherein R
5
and R
6
are the same or different and are each linear or branched C
1
-C
12
alkyl or wherein R
5
and R
6
together with the nitrogen atom to which they are bonded form a 5-, 6- or 7-membered ring, which may contain further hetero atoms, by linear or branched C
1
-C
8
alkyl-R
7
wherein R
7
is an OR
4
, COOR
4
or NR
5
R
6
radical as defined above or is NH
2
, or by N
⊕
R
5
R
6
R
7
wherein R
5
, R
6
and R
7
are as defined above.
When, in the compounds of formulae (1) and (3), R, R
1
, R
1
′ and/or R
8
are N
⊕
R
5
R
6
R
7
or R
2
and/or R
3
are N
⊕
R
5
R
6
R
7
-substituted aryl wherein R
5
, R
6
and R
7
are as defined above, the following anions are suitable for balancing the positive charge on the N
⊕
R
5
R
6
R
7
group: halide, for example chloride, perchlorate, sulfate, nitrate, hydroxide, BF
4
−
, PF
6
−
, carboxylate, acetate, tosylate and triflate. Of those anions, bromide and chloride are preferred.
In compounds of formulae (1) and (3) in which n, m or p is 2 or 3, the radicals R, R
1
and R
1
′ have the same or different meanings.
When Y is a 1,2-cyclohexylene radical, it may be present in any of its stereoisomeric cis/trans forms.
Preferably, Y is a radical of formula —(CH
2
)
r
— wherein r is an integer from 1 to 4, especially 2, or is a radical of formula —C(R
4
)
2
—(CH
2
)
p
—C(R
4
)
2
— wherein p is a number from 0 to 3, especially 0, and each R
4
, independently of the others, is hydrogen or C
1
-C
4
alkyl, especially hydrogen or methyl, or is a 1,2-cyclohexylene radical or a 1,2-phenylene radical of formula:
Halogen is preferably chlorine, bromine or fluorine, chlorine being especially preferred.
When n, m or p is 1, the groups R, R
1
and R
1
′ are preferably in the 4-position of the respective benzene ring except when R, R
1
or R
1
′ is nitro or COOR
4
, in which case that group is preferably in the 5-position. When R, R
1
or R
1
′ is a N
⊕
R
5
R
6
R
7
group, that group is preferably in the 4- or 5-position.
When n, m or p is 2, the two R, R
1
or R
1
′ groups are preferably in the 4,6-position of the respective benzene ring except when they are nitro or COOR
5
, in which case the two groups are preferably in the 3,5-position.
When R, R
1
or R
1
′ is di(C
1
-C
12
alkyl)amino, the alkyl group may be straight-chain or branched. Preferably, it contains from 1 to 8, especially from 1 to 3, carbon atoms.
Preferably, the radicals R, R
1
and R
1
′ are hydrogen, OR
4
, N(R
4
)
2
or N
⊕
(R
4
)
3
, wherein the R
4
groups in N(R
4
)
2
or N
⊕
(R
4
)
3
may be different and are hydrogen or C
1
-C
4
alkyl, especially methyl, ethyl or isopropyl.
The radicals R
2
and R
3
are especially hydrogen, methyl, ethyl or unsubstituted phenyl.
Aryl is, for example, naphthyl or, especially, phenyl.
When R
5
and R
6
together with the nitrogen atom to which they are bonded form a 5-, 6- or 7-membered ring, the ring is especially a pyrrolidine, piperidine, morpholine or piperazine ring. The piperazine ring may be substituted, for example by alkyl, at the nitrogen atom that is not bonded to the phenyl or alkyl radical.
Suitable anions A include, for example, halide, such as chloride or bromide, perchlorate, sulfate, nitrate, hydroxide, BF
4
−
, PF
6
−
, carboxylate, acetate, tosylate
Bachmann Frank
Dannacher Josef
Grey Bryan David
Hazenkamp Menno
Kvita Petr
Ciba Specialty Chemicals Corporation
Del Cotto Gregory R.
Mansfield Kevin T.
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