Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2001-01-16
2002-10-29
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S493000, C106S494000, C430S007000, C430S322000, C524S100000, C544S187000, C544S188000
Reexamination Certificate
active
06471766
ABSTRACT:
BACKGROUND OF THE INVENTION
a) Field of the invention
This invention relates to pigment dipersants and pigment compositions using the same.
b) Detailed Description of the Related Art
Upon mixing and dispersing a pigment in a vehicle such as a paint, gravure ink or offset ink, difficulty is generally encountered in stably dispersing the pigment in the vehicle. Fine particles of the pigment, which have once been dispersed in the vehicle, tend to flocculate in the vehicle. This leads to an increase in the viscosity of the vehicle with the pigment dispersed therein, a reduction in the coloring power of an ink or paint making use of the vehicle with the pigment dispersed therein, a reduction in the gloss of a coating of the ink or paint, or the like.
SUMMARY OF THE INVENTION
An object of the present invention is, therefore, to provide a pigment dispersant, which upon production of printing inks (offset inks, gravure inks and the like), various paints, plastics, pigment-type textile printing agents, dry or wet toners for electrophotography, inks for ink-jet recording, inks for thermal transfer recording, inks for writing instruments, colorants for color filters, and the like, prevents flocculation of dispersed pigment particles and permits the production of these inks and the like with excellent flow property and high stability.
In one aspect of the present invention, there is accordingly provided a pigment dispersant (hereinafter simply called “dispersant” ), which comprises a compound represented by the following formula (I) or (II) or a metal, ammonium or amine salt thereof:
wherein X
i
is a hydrogen atom, a halogen atom, or an alkyl or acylamino group which may be unsubstituted or substituted by at least one atom or group selected from the group consisting of halogen atoms, alkyl groups and an acylamino group, Y
1
is an anthraquinonylamino, phenylamino, naphthylamino or phenoxy group which may be unsubstituted or substituted by at least one atom or group selected from the group consisting of halogen atoms, alkyl groups and an acylamino group, R
1
is a hydrogen atom or a substituted or unsubstituted alkyl or phenyl group, and R
2
is a substituted or unsubstituted alkylene, phenylene or naphthylene group; or
wherein X
2
is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group, R
3
is a hydrogen atom or a substituted or unsubstituted alkyl or phenyl group, R
4
is a substituted or unsubstituted phenyl or naphthyl group, and n means an average number of sulfonic acid groups introduced in said compound and stands for a number of from 0.5 to 2.
In another aspect of the present invention, there is also provided a pigment composition, for example, a colorant for gravure inks, paints or color filters, which comprises a pigment and the above-described dispersant.
The dispersant of the present invention is useful for dispersing various pigments, which include organic pigments and inorganic pigments, in vehicles for a variety of applications such as printing inks (offset inks, gravure inks and the like), various paints, plastics, pigment-type textile printing agents, dry or wet toners for electrophotography, inks for ink-jet recording, inks for thermal transfer recording, inks for writing instruments and inks for color filters. The dispersant of the present invention can significantly improve the flow property of inks, paints and the like, can prevent flocculation of pigment particles, and hence, can provide colored articles which show excellent gloss and vividness.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
The dispersant according to the present invention features in the inclusion of a yellow to reddish purple anthraquinonylaminotriazine structure in its structure. It has excellent compatibility with various pigments, and is usable for dispersing a variety of pigments. Owing to its excellent pigment dispersing effect, the dispersant according to the present invention can also be used for the production of colorants which are useful in various applications.
The dispersant according to the present invention can be produced by a process disclosed, for example, in JP 46-33232 B, JP 46-33233 B or JP 46-34518 B or by a similar process.
For example, the dispersant represented by the formula (I) can be obtained by reacting 1 mole of a substituted or unsubstituted 1-aminoanthraquinone, 1 mole of one of a substituted or unsubstituted aniline, a substituted or unsubstituted phenol or a substituted or unsubstituted 1-aminoanthraquinone, and 1 mole of cyanuric chloride at 130° C. to 170° C. for 2 to 6 hours in an inert solvent such as o-dichlorobenzene and further reacting 1 mole of an aliphatic or aromatic amine, which contains one sulfonic acid group per molecule, at 150° C. to 170° C. for 3 to 4 hours.
The dispersant presented by the formula (II), on the other hand, can be obtained by reacting 2 moles of a substituted or unsubstituted 1-aminoanthraquinone and 1 mole of cyanuric chloride at 130° to 170° C. for 2 to 6 hours in an inert solvent such as o-dichlorobenzene, further reacting 1 mole of an aromatic amine, which does not contain any sulfonic acid group, at 150° C. to 170° C. for 3 to 4 hours, and then sulfonating the reaction product with a sulfonating agent such as fuming sulfuric acid.
Examples of the aliphatic amine or aromatic amine, which contains one sulfonic acid group per molecule and is useful for the production of the compound of the formula (I), can include taurine, N-methyltaurine, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, sulfanilic acid, 4-chloroaniline-3-sulfonic acid, 2-nitroaniline-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, o-anisidine-5-sulfonic acid, p-anisidine-5-sulfonic acid, o-toluidine-4-sulfonic acid, m-toluidine-4-sulfonic acid, p-toluidine-2-sulfonic acid, 2-chloro-p-toluidine-3-sulfonic acid, 3-amino-6-chloro-4-sulfobenzoic acid, 1-amino-8-naphthalenesulfonic acid, 2-amino-1-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, 6-amino-1-naphthalenesulfonic acid and 5-amino-3-naphthalenesulfonic acid.
Examples of the aromatic amine useful for the production of the compound of the formula (II) can include aniline, N-methylaniline, toluidine (o-, m- or p-), anisidine (o-, m- or p-), chloroaniline (o-, m- or p-), diphenylamine, 1-naphthylamine and 2-naphthylamine.
Illustrative of the metal, which may form the metal salt with the compound represented by the formula (I) or (II), are alkali metals such as Li, Na and K; and multivalent metals such as Ca, Ba, Al, Mn, Sr, Mg and Ni. Illustrative of the amine, which may form the amine salt with the compound represented by the formula (I) or (II), are (mono, di or tri)alkylamines, substituted or unsubstituted alkylenediamines, alkanolamines, and alkylammonium chlorides.
Concerning the mixing ratio of the dispersant of the present invention to the pigment, the dispersant may be added in a proportion of from 0.05 to 40 parts by weight, preferably from 0.1 to 10 parts by weight per 100 parts by weight of the pigment. If the dispersant is added in an unduly low proportion, the intended effect of the dispersant cannot be fully brought about. Even if the dispersant is added in an excessively high proportion, the effect of the dispersant cannot be obtained so much as its proportion. On the contrary, use of the resulting pigment composition leads to paints or inks with reductions in the physical properties of their vehicles, and due to the color of the dispersant itself, the hues of the dispersed pigments are substantially modified.
Examples of pigments, the dispersion of which can be effectively achieved by the use of the dispersant of the present invention, can include organic pigments such as azo pigments, phthalocyanine pigments, quinacridone pigments, anthraquinone pigments, dianthraquinonyl pigments, isoindolinone pigments, perylene/perionone pigments, dioxazine pigments, indanthrone pigments, flavanthrone pigments, anthanthrone pigments, pyranthrone pigments, diketopyrrolopyrrole pigments, vat-dye pigments and basic-dye pigments; and inorganic
Aoki Kazutaka
Ohki Shigeru
Okamoto Hisao
Saikatsu Hiroaki
Soga Takayuki
Dainichiseika Color & Chemicals Mfg. Co. Ltd.
Green Anthony J.
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