Water-soluble granules of phthalocyanine compounds

Details Water-soluble granules of phthalocyanine compounds Water-soluble granules of phthalocyanine compounds

1999-05-14

2001-09-18

Gupta, Yogendra N. (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

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

Reexamination Certificate

active

06291412

ABSTRACT:

The present invention relates to water-soluble granules of phthalocyanine compounds, to a method of producing them, and to the use thereof in washing agent preparations.
Water-soluble phthalocyanine dyes, especially zinc and aluminum phthalocyanine-sulfonates, are frequently used as photoactivators in washing agent preparations. In view of the fact that such photoactivators dissolve too slowly in water, problems often arise, especially when there is inadequate mixing of the washing liquor, because the coloured photoactivators stain the laundry.
Solid microcapsules of phthalocyanine photoactivators that contain at least 38% of an encapsulating material have already been described in EP-B-0 333 270, but those microcapsules are also not able to satisfy all of the consumer's requirements in terms of dissolving behaviour and staining of the laundry.
It has now been found that, surprisingly, granules comprising a water-soluble phthalocyanine compound, an anionic dispersing agent and a maximum of 25% by weight of an organic polymer are distinguished by a high rate of dissolution in water, with the result that the problems mentioned above are substantially or entirely eliminated. A further advantage of such granules is that, even in the case of prolonged contact with a non-ionic surfactant, the phthalocyanine compound is not dissolved out of the granules and the laundry is not stained.
The present invention accordingly relates to water-soluble granules of phthalocyanine compounds comprising
a) from 2 to 50% by weight of a water-soluble phthalocyanine compound,
b) from 10 to 95% by weight of an anionic dispersing agent,
c) from 0 to 25% by weight of a water-soluble organic polymer,
d) from 0 to 10% by weight of a further additive and
e) from 3 to 15% by weight of water, based on the total weight of the granules.
There come into consideration as the phthalocyanine compound for the granules according to the invention phthalocyanine complexes having a di-, tri- or tetra-valent metal (complexes having a d
0
or d
10
configuration) as the central atom. Such complexes are especially water-soluble Zn, Fe(II), Ca, Mg, Na, K, Al, Si(IV), P(V), Ti(IV), Ge(IV), Cr(VI), Ga(III), Zr(IV), In(III), Sn(IV) and Hf(VI) phthalocyanines, aluminum phthalocyanine and zinc phthalocyanine being especially preferred.
Advantageously, the composition according to the invention comprises a phthalocyanine compound of formula
[Me]
q
—[PC&Brketclosest;&Brketopenst;Q
1
]
r
−
A
s
−
  (1a)
or
[Me&Brketclosest;
q
&Brketopenst;PC&Brketclosest;&Brketopenst;Q
2
]
r
  (1b)
wherein
PC is the phthalocyanine ring system;
Me is Zn, Fe(II), Ca, Mg, Na, K, Al—Z
1
, Si(IV), P(V), Ti(IV), Ge(IV), Cr(VI), Ga(III), Zr(IV), In(III), Sn(IV) or Hf(VI);
Z
1
is a halide, sulfate, nitrate, acetate or hydroxy ion;
q is 0, 1 or 2;
r is from 1 to 4;
Q
1
is a sulfo or carboxyl group; or a radical of the formula
—SO
2
X
2
—R
6
—X
3
+
; —O—R
6
—X
3
+
; or —(CH
2
)
t
—Y
1
+
;
wherein
R
6
is branched or unbranched C
1
-C
8
alkylene; or 1,3- or 1,4-phenylene;
X
2
is —NH—; or —N—C
1
—C
5
alkyl-;
X
3
+
is a group of the formula
and, in the case where R
6
=C
1
-C
8
alkylene, may also be a group of the formula
Y
1
+
is a group of the formula
t is 0 or 1;
and in the above formulae
R
7
and R
8
are each independently of the other C
1
-C
6
alkyl;
R
9
is C
1
-C
6
alkyl; C
5
-C
7
cycloalkyl; or NR
11
R
12
;
R
10
and R
11
are each independently of the other C
1
-C
5
alkyl;
R
12
and R
13
are each independently of the other hydrogen or C
1
-C
5
alkyl;
R
14
and R
15
are each independently of the other unsubstituted C
1
-C
6
alkyl or C
1
-C
6
alkyl substituted by hydroxy, cyano, carboxy, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkoxy, phenyl, naphthyl or by pyridyl;
u is from 1 to 6;
A
1
is the balance of an aromatic 5- to 7-membered nitrogen heterocycle which may contain one or two further nitrogen atoms as ring members, and
B
1
is the balance of a saturated 5- to 7-meambered nitrogen heterocycle which may contain 1 or 2 further nitrogen, oxygen and/or sulfur atoms as ring members;
Q
2
is hydroxy; C
1
-C
22
alkyl; branched C
4
-C
22
alkyl; C
2
-C
22
alkenyl; branched C
4
-C
22
alkenyl or a mixture thereof; C
1
-C
22
alkoxy; a sulfo or carboxyl radical; a radical of the formula
a branched alkoxy radical of the formula
or
an alkylethyleneoxy unit of the formula —(T
1
)
d
—(CH
2
)
b
(OCH
2
CH
2
)
a
—B
3
or an ester of the formula COOR
23
, in which formulae
B
2
is hydrogen; hydroxy; C
1
-C
30
alkyl; C
1
-C
30
alkoxy; —CO
2
H; —CH
2
COOH; SO
3
−
M
1
+
;
—OSO
3
−
M
1
+
; —PO
3
2−
; M
1
; —OPO
3
2−
M
1
; or a mixture thereof;
B
3
is hydrogen; hydroxy; —COOH; —SO
3
−
M
1
+
; —OSO
3
−
M
1
+
; or C
1
-C
6
alkoxy;
M
1
is a water-soluble cation;
T
1
is —O—; or —NH—;
X
1
and X
4
are each independently of the other —O—; —NH—; or —N—C
1
-C
5
alkyl;
R
16
and R
17
are each independently of the other hydrogen, a sulfo group or a salt thereof, a carboxyl group or a salt thereof, or a hydroxyl group, at least one of the radicals R
16
and R
17
being a sulfo or carboxyl group or a salt thereof,
Y
2
is —O—, —S—, —NH— or —N—C
1
-C
5
alkyl;
R
18
and R
19
are each independently of the other hydrogen, C
1
-C
6
alkyl, hydroxy-C
1
-C
6
alkyl, cyano-C
1
-C
6
alkyl, sulfo-C
1
-C
6
alkyl, carboxy or halo-C
1
-C
6
alkyl; unsubstituted phenyl; or phenyl substituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy, sulfo or by carboxy; or R
18
and R
19
, together with the nitrogen atom to which they are bonded, form a saturated 5- or 6-membered heterocyclic ring that may in addition contain a further nitrogen atom or an oxygen atom as ring member;
R
20
and R
21
are each independently of the other a C
1
-C
6
alkyl or aryl-C
1
-C
6
alkyl radical;
R
22
is hydrogen; unsubstituted C
1
-C
6
alkyl; or C
1
-C
6
alkyl substituted by halogen, hydroxy, cyano, phenyl, carboxy, C
1
-C
6
alkoxycarbonyl or by C
1
-C
6
alkoxy;
R
23
is C
1
-C
22
alkyl, branched C
4
-C
22
alkyl, C
1
-C
22
alkenyl or branched C
4
-C
22
alkenyl; C
3
-C
22
-glycol; C
1
-C
22
alkoxy; branched C
4
-C
22
alkoxy; or a mixture thereof;
M is hydrogen; or an alkali metal ion or ammonium ion;
Z
2
is a chlorine, bromine, alkyl sulfate or aralkyl sulfate ion;
a is 0 or 1;
b is from 0 to 6;
c is from 0 to 100;
d is 0; or 1;
e is from 0 to 22;
v is an integer from 2 to 12;
w is 0 or 1; and
A is an organic or inorganic anion,
and
s in the case of monovalent anions A
−
is equal to r and in the case of polyvalent anions is ≦r, it being necessary for A
s
−
to balance the positive charge; and when r≠1, the radicals Q
1
may be identical or different,
and wherein the phthalocyanine ring system may also comprise further solubilising groups.
The number of substituents Q
1
and Q
2
in formula (1a) and in formula (1b), respectively, which substituents may be identical or different, is from 1 to 8 and, as is customary with phthalocyanines, the number need not be a whole number (degree of substitution). If other, non-cationic substituents are also present, the sum of the latter and the cationic substituents is from 1 to 4. The minimum number of substituents that have to be present in the molecule is governed by the water-solubility of the resulting molecule. An adequate solubility is achieved when the amount of phthalocyanine compound that dissolves is sufficient to cause a photodynamically catalysed oxidation on the fibres. A solubility of as low as 0.01 mg/l may be sufficient, but generally a solubility of from 0.001 to 1 g/l is expedient.
Halogen is fluorine, bromine or, especially, chlorine.
There come into consideration as
groups especially:
The group
is preferred.
The above-listed groups likewise come into consideration as heterocyclic rings in the group
only the bond to the remaining substituents being effected by way of a carbon atom.
In all substituents, phenyl, naphthyl and aromatic hetero rings may be substituted by one or two furth

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