Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2003-06-10
2004-12-07
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S494000, C106S495000, C106S496000, C106S497000, C106S498000, C106S499000, C524S084000, C524S087000, C524S089000, C524S090000, C524S094000, C524S166000
Reexamination Certificate
active
06827775
ABSTRACT:
By virtue of their planar chromophore structure, polycyclic and heterocyclic pigments have many properties in common: they are virtually insoluble, even at high processing temperatures, and exhibit very good fastness properties, for example excellent stability towards light, weathering and heat. On the other hand, they exhibit poor dispersibility and the rheology of compositions comprising them still leaves something to be desired.
It has long been known that certain application-related properties of organic pigments can be improved by the addition of dispersants. Pigment derivatives, including a large number of sulfonates, have proved to be especially suitable dispersants.
U.S. Pat. No. 5,271,759 discloses pigment compositions comprising organic pigments having a wide variety of chromophores, a sulfonated pigment derivative and a polymeric quaternary ammonium salt, which pigment compositions are said to have good rheology in surface-coatings and printing inks and to allow warp-free pigmenting of polyolefins. Sulfonated diketopyrrolopyrrole sulfonates and phthalocyanine sulfonates are given as examples, the polymeric counter-ion being, for example, poly(N,N-dimethyl-3,5-dimethylenepiperidinium) or the cationic amine/formaldehyde condensate ®Tinofix EW.
U.S. Pat. Nos. 3,754,958, 4,055,440, JP-A-62/181373, U.S. Pat. No. 4,726,847 and EP-A-0 638 615 relate to modified phthalocyanine pigments. Compared with a more highly sulfonated product, according to U.S. Pat. No. 3,754,958 an only partially sulfonated pigment having the same counter-ion exhibits improved colour strength, gloss and transparency, there being disclosed as cation C
8
-C
14
alkyltrimethylammonium. In contrast, U.S. Pat. No. 4,055,440 discloses the improvement in the rheology of a more highly sulfonated product by the use of dehydroabietylamine. The fluidity of inks is increased in JP-A-62/181373 by sulfonated phthalocyanines with quaternary ammonium ions having from 15 to 40 carbon atoms, of which from 12 to 18 have to be in an alkyl group; in the Examples, didodecyldimethylammonium and dimethyldioctadecylammonium are disclosed. Similarly, EP-A-0 638 615 discloses a process for the preparation of a pigment having improved gloss, dispersibility, fluidity and colour strength by the wet-grinding of copper phthalocyanine together with an ammonium salt of a sulfonated copper phthalocyanine, there being disclosed as ammonium cations inter alia didodecyldimethylammonium and hexadecyltrimethylammonium. According to U.S. Pat. No. 4,726,847, the rheological and optical properties of a composition consisting of a phthalocyanine pigment and a sulfonated phthalocyanine can be improved by coating with a combination of anionic and cationic surfactants, there being used as surfactant inter alia ®Ethomeen S/12 [61-24-0].
U.S. Pat. Nos. 4,791,204, 5,145,524, EP-A-0 430 875, EP-A-1 104 789, GB-B-2 238 550, U.S. Pat. Nos. 5,380,870 and 5,840,907 relate to diketopyrrolopyrrole pigment compositions. Rheology, stability towards heat and warping characteristics of diketopyrrolopyrrole pigments are improved according to U.S. Pat. No. 4,791,204 by the addition of modified diketopyrrolopyrroles, including, among a large number of possibilities, ammonium sulfonates, for example a hexamethylenediamine salt. A further improvement in rheology is achieved in U.S. Pat. No. 5,145,524 by the addition of certain amounts of an alkoxyvinyl polymer as viscosity index improver. Both in the case of diketopyrrolopyrroles and in the case of quinacridones, EP-A-0 430 875 prefers certain sulfonates, the storage stability being increased and flooding and the tendency towards flocculation being reduced; in one example hexadecyltrimethylammonium is disclosed as cation. In EP-A-1 104 789, sulfonated derivatives of Pigment Red 264 are used instead of those of Pigment Red 254. Rheology and colour saturation are again increased in GB-B-2 238 550 by the use of special diketopyrrolopyrrole sulfonate mixtures instead of single sulfonates, there being mentioned as counter-ion inter alia a hexadecyltrimethylammonium salt. Conversely, U.S. Pat. No. 5,380,870 discloses sulfonated diketopyrrolopyrroles which, owing to mixed counter-ions, exhibit increased colour strength and a high degree of dispersibility as well as fastness to heat and to light. More specific, N-substituted diketopyrrolopyrroles are the subject of U.S. Pat. No. 5,840,907, it being possible for those products too to be partially sulfonated and to be present, for example, also in the form of acetyltrimethylammonium or benzyltributylammonium salt.
In the case of Pigment Red 177, a dianthraquinonyl pigment of the 1-aminoanthraquinone series, according to U.S. Pat. No. 4,863,522 the rheological properties can likewise be improved by the addition of a sulfonated derivative, there being disclosed as the cation thereof inter alia tetramethylammonium. Similar subject matter is disclosed by U.S. Pat. No. 4,692,189 in the case of indanthrone blue (Pigment Blue 60) where, in addition to an improvement in rheology, the colour strength and gloss are also improved, and by U.S. Pat. No. 4,865,650 in the case of isoindolinones where, in addition to an improvement in rheology, the dispersion stability, and tendency towards flocculation are also improved. According to U.S. Pat. No. 5,264,034, rheology, dispersibility, flocculation stability, colour strength, transparency and surface properties are improved in similar manner also in the case of perylenes, it being possible for the perylene sulfonates also to be in the form of ammonium salts, for example in the form of stearyl-ammonium salts. Finally, U.S. Pat. No. 5,275,653 discloses compositions comprising a dioxazine pigment (Pigment Violet 23) and a sulfonated derivative thereof (for example in the form of a calcium-, abietyl-, stearyl-, di(2-ethylhexyl)- or triethyl-ammonium salt) that acts as a dispersant, as a result of which the rheological and coloristic properties are said to be improved.
In the prior art, the dispersants most commonly used are calcium sulfonates. In the case of the ammonium sulfonates that are occasionally used, however, there is confusing variety in the cations to be used, without any pointers being given to possible further improvements, apart from the occasional reference to the necessity for at least one long-chain group to be present in the case of phthalocyanine pigments.
In all the cases mentioned above, however, rheology, dispersibility, flocculation, flooding, gloss and colour strength are still unable to meet satisfactorily all of the ever growing demands. In addition, for various pigment types there are used pigment derivatives that have a variety of cations. In the case of formulations, therefore, a situation sometimes arises in which cations are exchanged, giving rise to impairment of the application-related properties for a reason that has been totally unrecognised hitherto.
According to this invention it has now been found, surprisingly, that it is possible to avoid the above-mentioned disadvantages and, especially, to obtain pigment compositions that are greatly improved in respect of rheology when sulfonated pigment derivatives having certain quaternary ammonium cations as cations are used as dispersants.
The invention therefore relates to a composition comprising
(a) a pigment of the 1-aminoanthraquinone, anthanthrone, anthrapyrimidine, quinacridone, dioxazine, diketopyrrolopyrrole, flavanthrone, indanthrone, isoindolinone, isoviolanthrone, perinone, perylene, phthalocyanine, pyranthrone or thioindigo series, or a solid solution or a mixed crystal consisting of a plurality of such pigments, and
(b) a sulfonation product of a pigment of the same series as pigment (a) or as the host component in the solid solution (a) or in the mixed crystal (a), wherein in the sulfonaton product the pigment is substituted by at least one group of formula (I)
wherein
R
1
is methyl or ethyl,
R
2
, R
3
and R
4
are each independently of the others C
6
-C
24
alkyl or C
6
-C
24
alkenyl,
m is a number from 0.3 to 1.0 and
n is a number from
Ciba Specialty Chemicals Corporation
Green Anthony J.
Stevenson Tyler A.
LandOfFree
Rheology improvers and pigment compositions having improved... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Rheology improvers and pigment compositions having improved..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Rheology improvers and pigment compositions having improved... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3331329