Title of Invention

WATERBORNE ACRYLATE-BASED PIGMENT DISPERSIONS

Abstract The invention relates to an aqueous pigment preparation containing an organic and/or inorganic pigment dispersed in an acrylatate resin solution and a dispersion agent. The preparation is characterized in that the acrylate resin is a copolymer consisting essentially of between 50 and 80 mol % of monoalkenyl aromatic compounds and between 20 and 50 mon % of acrylates, and has an average molar Mass Mv of between 1,000 and 50,000 g/mol, and in that the dispersion agent is a compound of formula (I): R- 0 -(CH2 -CH2 -0)m -CH2 -COOM, wherein R is a C10 -C20 alkyl radical or a C10 -C20 alkenyl radical, m is a number between 1 and 15, and M is a monovalent cation.
Full Text Description
Waterbome acrylate-based pigment dispersions
The present invention relates to waterbome pigment preparations, to processes for
preparing them, to their use for dyeing and printing natural and synthetic fiber
materials, to recording liquids, especially for the inkjet process, and to
electrophotographic toners, powder coating materials, and color fitters.
The inkjet process is a contactless printing process in which droplets of the recording
liquid are guided from one or more nozzles onto the substrate that is to be printed. In
order to obtain prints of high definition and resolution, the recording liquids and the
colorants present therein are required to meet stringent requirements, especially with
regard to purity, fineness of particles, stability on storage, viscosity, surface tension,
and conductivity. Very stringent requirements are imposed in particular on color
strength, shade, brilliance, and fastness properties, such as light fastness, water
fastness, and rub fastness, for example. High light fastness in particular is of great
importance for exterior inkjet applications and for the production of inkjet prints with
photographic quality.
The development of dyes which exhibit the desired combination of shade, brilliance,
color strength, light fastness, and water fastness has so far proven very difficult, with
the consequence that increasing interest is being focused on pigmented inks.
Pigmented inkjet preparations known to date often fail to meet the requirements the
inkjet industry imposes on them, exhibiting deficiencies in fine division, in thermal
stability and in storage stability, and also often poor printability, especially in thermal
printers.
One important quality criterion of an inkjet preparation is its flocculation stability. In
order not to clog the nozzles, the pigment particles must be smaller than 0.5 µm,
preferably smaller than 0.1 µm. Moreover, crystal growth or particle agglomeration
must be effectively prevented. This is generally achieved using certain dispersing
aids. When an inkjet ink is printed, it flows at high speed through the nozzles. As a
result of shearing and the effect of temperature, the stabilizing dispersing aid is often
removed from the pigment surface. The pigment flocculates and clogs the nozzles of
the printer. Another quality feature of an inkjet ink is its storage stability; in the course
of storage, the pigment particles must not agglomerate to form larger particles.
It is therefore an object of the invention to provide pigment preparations which satisfy
the aforementioned requirements in respect of fine division, thermal stability, storage
stability, printability, and coloristics.
This object has been achieved, surprisingly, by dispersing the pigment in a special,
water-soluble acrylate resin, defined below, in combination with a special dispersing
aid. When the acrylate resin is used alone, the resulting pigment preparations have
excellent storage properties, but the printability of the ink is inadequate. Similarly, the
use of other dispersing aids in combination with the acrylate resin leads to pigment
preparations lacking printability and stability on storage. The addition of the
dispersing aid of the invention results in a poorer solubility of the acrylate resin in the
liquid, so that the adsorption equilibrium of the resin is shifted positively in favor of
the surface of the pigment. This prevents removal of additives under shearing, at
high flow rate in the fine nozzles of the printer, from the surface of the pigment.
The present invention provides an aqueous pigment preparation, comprising an
organic and/or inorganic pigment dispersed in an acrylate resin solution and
dispersing aid, wherein the acrylate resin is a copolymer composed essentially of
from 50 to 80 mol% of monoalkenyl aromatics and from 20 to 50 mol% of acrylates
and has an average molar mass Mv of between 1 000 and 50 000 g/mol and wherein
the dispersing aid is a compound of the formula (I)
R - O - (CH2-CH2-O)m - CH2 - COOM (I)
in which
R is a C10-C20 alkyl radical or a C10-C20 alkenyl radical,
m is a number from 1 to 15, and
M is a monovalent cation.
By monoalkenyl aromatics are meant, in particular, monomers from the group
consisting of styrene, a-methylstyrene, vinyltoluene, tert-butylstyrene, and
o-chlorostyrene, and also mixtures thereof.
By acrylates are meant monomers from the group consisting of acrylic acid,
methacrylic acid, and esters of acrylic or methacrylic acid. Examples include the
following: methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, n-butyl
methacrylate, isopropyl methacrylate, isobutyl methacrylate, n-amyl methacrylate,
n-hexyl methacrylate, isoamyl methacrylate, 2-hydroxyethyl methacrylate,
2-hydroxypropyl methacrylate, N,N-dimethylaminoethyl methacrylate,
N.N-diethylaminoethyl methacrylate, t-butylaminoethyl methacrylate, 2-sulfoethyl
methacrylate, trifluoroethyl methacrylate, glycidyl methacrylate, benzyl methacrylate,
allyl methacrylate, 2-n-butoxyethyl methacrylate, 2-chloroethyl methacrylate, sec-
butyl methacrylate, tert-butyl methacrylate, 2-ethylbutyl methacrylate, cinnamyl
methacrylate, crotyl methacrylate, cyclohexyl methacrylate, cyclopentyl
methacrylate, 2-ethoxyethyl methacrylate, furfuryl methacrylate, hexafluoroisopropyl
methacrylate, methallyl methacrylate, 3-methoxybutyl methacrylate, 2-methoxybutyl
methacrylate, 2-nitro-2-methylpropyl methacrylate, n-octyl methacrylate, 2-ethylhexyl
methacrylate, 2-phenoxyethyl methacrylate, 2-phenylethyl methacrylate, phenyl
methacrylate, propargyl methacrylate, tetrahydrofurfuryl methacrylate and
tetrahydropyranyl methacrylate, and also the corresponding esters of acrylic acid.
The acrylate resin is preferably composed of from 60 to 70 mol% of monoalkenyl
aromatics and from 30 to 40 mol% of acrylates. Particular preference is given to
acrylate resins composed of the monomers styrene and (meth)acry!ic acid.
The average molar mass Mv, determined by gel permeation chromatography, is
preferably from 5 000 to 25 000 g/mol. The acrylate resins used in accordance with
the invention have an acid number of preferably between 110 and 250, in particular
between 190 and 220, mg KOH/g acrylate resin;
a glass transition temperature, Tg, of preferably from 40 to 140°C, more preferably
from 50 to 140°C, e.g., from 110 to 140°C;
a polydispersity of preferably from 1.5 to 3.5, more preferably from 1.5 to 2.5, in
particular from 2.0 to 2.4;
a density at 25°C of preferably from 1.05 to 1.3 g/cm3, in particular from 1.1 to 1.2
g/cm3; and a melting range of preferably from 120 to 160°C.
The acrylate resin is advantageously used in alkaline aqueous solution or
ammoniacal solution, preferably as a solution with a concentration of from 1 to 35%
by weight, in particular from 5 to 30% by weight.
The acrylate resins described above can be prepared in accordance with
US 4,529,787.
The acrylate resin copolymer used in accordance with the invention may include
small amounts, such as from 0.5 to 2 mol%, for example, of a surface-active
compound capable of polymerization.
The dispersing aid of the formula (I) is preferably a compound in which R is
C12-C18 alkyl or C12-C18 alkenyl, especially C13-C16 alkyl or C13-C16 alkenyl.
The number m is preferably from 1 to 10.
The monovalent cation M is preferably hydrogen, an alkali metal, especially Na or K,
or ammonium.
Examples of compounds of the formula (I) are:
(C13-C15)-alkyl-O-(CH2CH2-O)9.5-CH2COONa,
C16H33-O-(CH2CH2O)CH2COONa,
C18H35-O-(CH2CH2O)CH2COONa,
C18H35-O-(CH2CH2O)8-CH2COONa,
C18H37-O-(CH2CH2O)-CH2COONa.
Compounds of this kind are known from CH-A-324 665 and CH-A-283 986.
Particularly suitable organic pigments include monoazo, disazo, laked azo,
ß-naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex
pigments, and polycyclic pigments such as, for example, phthalocyanine,
quinacridone, perylene, perinone, thiazinine indigo, thioindigo, anthanthrone,
anthraquinone, flavanthrone, indanthrone, isoviolanthrone, pyranthrone, dioxazine,
quinophthalone, isoindolinone, isoindoline, and diketopyrrolopyrrole pigments or
carbon blacks.
Examples of suitable inorganic pigments include titanium dioxides, zinc sulfides, iron
oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides,
cobalt oxides, and bismuth vanadates.
The pigments used should be very finely divided, with preferably 95% and with
particular preference 99% of the pigment particles possessing a size average particle size is preferably morphology of the pigment particles may vary widely, and accordingly the viscosity
behavior of the pigment preparations may vary widely as a function of the particle
shape. To obtain a favorable viscosity behavior for the preparations, the particles
should preferably have a cuboid or spherical shape. Purified pigments are preferably
used. A selection of particularly preferred organic pigments includes carbon black
pigments, such as gas blacks or furnace blacks, for example; monoazo, disazo, and
benzimidazolone pigments, especially the Colour Index pigments Pigment Yellow 17,
Pigment Yellow 74, Pigment Yellow 83, Pigment Yellow 97, Pigment Yellow 120,
Pigment Yellow 128, Pigment Yellow 139, Pigment Yellow 151, Pigment Yellow 155,
Pigment Yellow 180, Pigment Yellow 213, Pigment Red 57:1, Pigment Red 146,
Pigment Red 176, Pigment Red 184, Pigment Red 185 or Pigment Red 269;
phthalocyanine pigments, especially the Colour Index pigments Pigment Blue 15,
Pigment Blue 15:3 or Pigment Blue 15:4, and quinacridone pigments, especially the
Colour Index pigments Pigment Red 122 or Pigment Violet 19.
The weight ratio between the pigment and acrylate resin is preferably from 1:0.05 to
1:1, in particular from 1:0.2 to 1:0.5.
The ratio of pigment to dispersant of the formula (I) is preferably fromi :0.05 to 1:1, in
particular from 1.0.2 to 1.0.5.
Preferred pigment preparations are composed of
a) from 5 to 50 % by weight, preferably from 15 to 25% by weight, of pigment,
b) from 0.25 to 20% by weight, preferably from 1 to 10% by weight, of the
acrylate resin,
c) from 1 to 12% by weight, preferably from 2 to 8% by weight, of a compound of
the formula (I),
d) from 5 to 60% by weight, preferably from 10 to 40% by weight, of water,
e) from 0 to 10% by weight, preferably from 0.1 to 5% by weight, of an organic
solvent,
f) from 0 to 15% by weight, preferably from 5 to 9% by weight, of a hydrotropic
substance,
g) from 0 to 10% by weight, preferably from 0.5 to 9.5% by weight, of further
customary additives,
based in each case on the total weight of the pigment preparation.
The solvents present in the pigment preparations described above may comprise an
organic solvent or a mixture of such solvents. Suitable solvents are, for example,
monohydric or polyhydric alcohols, their ethers and esters, e.g., alkanols, especially
those having from 1 to 4 carbon atoms, such as methanol, ethanol, propanol,
isopropanol, butanol or isobutanol, for example; dihydric or trihydric alcohols,
especially those having from 2 to 5 carbon atoms, e.g., ethylene glycol, propylene
glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol,
1,2,6-hexanetriol, glycerol, diethylene glycol, dipropylene glycol, triethylene glycol,
polyethylene glycol, tripropylene glycol, polypropylene glycol; lower alkyl ethers of
polyhydric alcohols, such as ethylene glycol monomethyl, monoethyl or monobutyl
ether, triethylene glycol monomethyl or monoethyl ether; ketones and ketone
alcohols, such as acetone, methyl ethyl ketone, diethyl ketone, methylisobutyl
ketone, methyl pentyl ketone, cyclopentanone, cyclohexanone, and diacetone
alcohol, for example; amides such as dimethylfomnamide, dimethylacetamide and
N-methylpyrrolidone, and also toluene and n-hexane.
Water used for preparing the pigment preparations is employed preferably in the
form of distilled or deionized water.
Examples of hydrotropic compounds, which may where appropriate also serve as
solvents, that can be used include formamide, urea, tetramethylurea, e-caprolactam,
ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, butylglycol,
methyl cellosolve, glycerol, n-methylpyrrolidone, 1,3-diethyl-2-imidazolidinone,
thiodiglycol, sodium benzenesulfonate, Na xylenesulfonate, Na toluenesulfonate,
sodium cumenesulfonate, Na dodecylsulfonate, Na benzoate, Na salicylate or
sodium butyl monoglycol sulfate.
The pigment preparations of the invention may further comprise customary additives,
examples being preservatives, cationic, anionic or nonionic surface-active
substances (surfactants and wetting agents), and viscosity regulators, e.g., polyvinyl
alcohol, cellulose derivatives, or water-soluble natural or synthetic resins as film
formers and/or binders for enhancing the adhesion and abrasion resistance.
Amines, such as ethanolamine, diethanolamine, triethanolamine, N,N-dimethyl-
ethanolamine or diisopropylamine, for example, serve primarily to raise the pH of the
pigment preparation, especially inkjet ink. They are normally present at from 0 to
10% by weight, preferably from 0.5 to 5% by weight, in the pigment preparation and
the inkjet ink prepared from it.
The present invention also provides a process for preparing such pigment
preparations, which comprises finely dispersing the pigment in the acrylate resin
solution and the dispersing aid of the formula (I) using a dispersing apparatus,
preferably a stirred ball mill, which is operated with a peripheral stirrer speed of more
than 12 m/s, employing nonmetallic grinding media with a diameter of less than or
equal to 1 mm, in the presence of water. The remaining additives may be present
during fine division and/or may be added subsequently. The acrylate resin is
advantageously used in the form of an aqueous solution, as described above.
The invention further provides for the use of the pigment preparations of the
invention as colorants for inks, especially inkjet inks, electrophotographic toners,
especially addition-polymerization toners, powder coated materials, and color filters.
The pigment preparations of the invention are suitable as colorants in
electrophotographic toners and developers, such as one- or two-component powder
toners (also called one- or two-component developers), magnetic toners, liquid
toners, addition-polymerization toners, and further, specialty toners.
Typical toner binders are addition-polymerization resins, polyaddition resins,
polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene,
acrylate, polyester or phenol epoxy resins, polysulfones, polyurethane, individually or
in combination, and also polyethylene and polypropylene, which may include yet
further ingredients, such as charge control agents, waxes, or flow aids, or may have
these added to them subsequently.
The preparations of the invention are further suitable as colorants in powders and
powder coating materials, especially in triboelectrically or electrokinetically sprayed
powder coating materials which are used for surface coating articles made, for
example, of metal, wood, plastic, glass, ceramic, concrete, textile material, paper or
rubber.
As powder coating materials use is made typically of epoxy resins, carboxyl- and
hydroxyl-containing polyester resins, polyurethane resins, and acrylic resins,
together with customary hardeners. Combinations of resins are also employed. For
instance, epoxy resins are frequently used in combination with carboxyl- and
hydroxyl-containing polyester resins. Typical hardener components are, for example,
acid anhydrides, imidazoles and also dicyandiamide and their derivatives, capped
isocyanates, bisacylurethane, phenolic and melamine resins, triglycidyl
isocyanurates, oxazolines, and dicarboxylic acids.
The preparations of the invention are also suitable as colorants for color filters, and
also for both additive and subtractive color generation.
By inkjet inks are meant not only waterborne inks (including microemulsion inks) but
also nonaqueous (solvent-based) inks, and inks which operate in accordance with
the hotmelt process.
Microemulsion inks are based on organic solvents, water, and, where appropriate,
an additional hydrotropic substance (interface mediator). Inks on a nonaqueous
basis comprise essentially organic solvents and, where appropriate, a hydrotropic
substance.
The present invention additionally provides inkjet recording liquids containing
generally from 0.5 to 15% by weight, preferably from 1.5 to 8% by weight, of the
pigment preparation of the invention, based on the total weight of the recording
liquid.
Microemulsion inks consist essentially of from 0.5 to 15% by weight, preferably from
1.5 to 8% by weight, of the pigment preparation of the invention, from 5 to 99% by
weight of water, and from 0.5 to 94.5% by weight of organic solvent and/or
hydrotropic compound.
Solvent-based inkjet inks consist essentially of from 0.5 to 15% by weight of the
pigment preparation of the invention and from 85 to 94.5% by weight of an organic
solvent and/or hydrotropic compound. Carrier materials for solvent-based inkjet inks
may be polyolefins, natural rubber and synthetic rubber, polyvinyl chloride, vinyl
chloride-vinyl acetate copolymers, polyvinyl butyrates, wax/latex systems or
combinations thereof, which are soluble in the "solvent".
Hotmelt inks are based predominantly on organic compounds, such as waxes, fatty
acids, fatty alcohols or sulfonamides, which are solid at room temperature and
become liquid on heating, the preferred melting range being situated between about
60°C and about 140°C. The invention also provides a hotmelt inkjet ink consisting
essentially of from 20 to 90% by weight of wax, from 1 to 10% by weight of the
pigment preparation of the invention, from 0 to 20% by weight of the additional
polymer (as "dye dissolver"), from 0 to 5% by weight of dispersing aid, from 0 to 20%
by weight of viscosity modifiers, from 0 to 20% by weight of plasticizers, from 0 to
10% by weight of tack additive, from 0 to 10% by weight of transparency stabilizer
(which prevents, for example, crystallization of the waxes), and from 0 to 2% by
weight of antioxidant.
The inkjet inks of the invention can be prepared by dispersing the pigment
preparation of the invention into the microemulsion medium or into the aqueous or
nonaqueous medium or into the wax for preparing a hotmelt inkjet ink.
The invention further provides a set of pigment preparations that includes at least
one colorant preparation in each of the colors black, cyan, magenta, and yellow,
wherein at least one of the preparations corresponds to the preparation of the
invention.
Preference is given in this context to a set of pigment preparations whose black
preparation includes carbon black as colorant, especially a gas black or furnace
black; whose cyan preparation includes a pigment from the group of the
phthalocyanine pigments, especially the Colour Index pigments Pigment Blue 15,
Pigment Blue 15:3 or Pigment Blue 15:4; whose magenta dispersion includes a
pigment from the group of the quinacridones, preferably Colour Index Pigment
Red 122 or Colour Index Pigment Violet 19, or from the group of the monoazo,
disazo, isoindoline or benzimidazolone pigments, especially the Colour Index
pigments Pigment Red 57:1, Pigment Red 146, Pigment Red 176, Pigment Red 184,
Pigment Red 185 or Pigment Red 269; and whose yellow preparation includes
preferably a pigment from the group of the monoazo, disazo, isoindoline or
benzimidazolone pigments, especially the Colour Index pigments Pigment Yellow 17,
Pigment Yellow 74, Pigment Yellow 83, Pigment Yellow 97, Pigment Yellow 120,
Pigment Yellow 128, Pigment Yellow 139, Pigment Yellow 151, Pigment Yellow 155,
Pigment Yellow 180 or Pigment Yellow 213.
The invention further provides a set of printing inks that includes at least one printing
ink in each of the colors black, cyan, magenta, and yellow, wherein at least one of
the printing inks comprises the pigment preparation of the invention in dilute or
undiluted form with or without further additives.
In addition to the printing of paper, natural and synthetic fiber materials, films, and
plastics, inkjet inks may also be employed on glass, ceramic, concrete, and the like.
Examples
In the examples below the acrylate solution used comprises an acrylate resin
characterized by the following features:
Copolymer of 60 - 70 mol% of monostyrene, 30 - 40 mol% of acrylic acid.
Specif, mass: 1 150 kg/m3
Acid number: 214
Glass transition temperature: 128°C
Molar mass: 17 250 g/mol
Melting range: 140-150°C
Polydispersity: 2.3
The acrylate solution itself is composed of 25% by weight of the acrylate, 3.9% by
weight of NaOH, and 71.9% by weight of water.
Example 1 Pigment preparation with Pigment Blue 15:3 for inkjet inks
20 parts C.I. Pigment Blue 15:3
25 parts acrylate solution
5 parts dispersant: R-O-(CH2CH2O)9.5-CH2COONa where R = C13-C15 alkyl
15 parts propylene glycol
0.2 part preservative
and 34.8 parts water are homogenized using a dissolver.
The suspension is subsequently ground using a stirred ball mill (Drais model PML)
with zirconium mixed oxide grinding media, diameter 0.3 - 0.4 mm. The resulting
pigment preparation is adjusted with water to a pigment content of 20%.
The pigment preparation possesses excellent fluidity, stability of viscosity, and
flawless flocculation stability when stored at room temperature and 60°C for
one month. Aqueous dilutions of this pigment concentrate, at 3%, are likewise
flocculation stable.
Example 2 Pigment preparation with Pigment Red 122 for inkjet inks
A preparation containing
20 parts C.I. Pigment Red 122
10 parts acrylate solution
3 parts dispersant: R-O-(CH2CH2O)9.5-CH2COONa where R = C13-C15 alkyl
15 parts propylene glycol
0.2 part preservative
51.8 parts water
is prepared as described in example 1.
Example 3 Pigment preparation with Pigment Yellow 155 for inkjet inks
A preparation containing
20 parts C.I. Pigment Yellow 155
25 parts acrylate solution
5 parts dispersant: R-O-(CH2CH2O)9.5-CH2COONa where R = C13-C15 alkyl
15 parts propylene glycol
0.2 part preservative
34.8% water
is prepared as described in example 1.
Example 4 Pigment preparation with Pigment Yellow 180 for inkjet inks
A preparation containing
20 parts C.I. Pigment Yellow 180
25 parts acrylate solution
5 parts dispersant: C18H35O(CH2CH2O)12CH2COONa
15 parts propylene glycol
0.2 part preservative
34.8 parts water
is prepared as described in example 1.
Example 5 Pigment preparation with Pigment Yellow 74 for inkjet inks
A preparation containing
20 parts C.I. Pigment Yellow 74
25 parts acrylate solution
5 parts dispersant: C18H35O(CH2CH2O)12CH2COONa
15 parts propylene glycol
0.2 part preservative
34.8 parts water
is prepared as described in example 1.
Example 6 Pigment preparation with Pigment Yellow 151 for inkjet inks
A preparation containing
20 parts C.I. Pigment Yellow 151
25 parts acrylate solution
5 parts dispersant: C18H35O(CH2CH2O)12CH2COONa
15 parts propylene glycol
0.2 part preservative
34.8 parts water
is prepared as described in example 1.
Example 7 Pigment preparation with Pigment Yellow 151 for inkjet inks
A preparation containing
20 parts PV Fast Yellow H2G
25 parts acrylate solution
3 parts dispersant: C18H35O(CH2CH2O)12CH2COONa
15 parts propylene glycol
0.2 part preservative
36.8 parts water
is prepared as described in example 1.
Example 8 Pigment preparation with Pigment Black 7 for inkjet inks
A preparation containing
20 parts Pigment Black 7
25 parts acrylate solution
7 parts dispersant: C18H35O(CH2CH2O)12CH2COONa
15 parts propylene glycol
0.2 part preservative
39.8 parts water
is prepared as described in example 1.
Example 9 Pigment preparation with Pigment Black 7 for inkjet inks
A preparation containing
20 parts Pigment Black 7
25 parts acrylate solution
15 parts propylene glycol
7 parts dispersant: C18H35O(CH2CH2O)12CH2COONa
0.2 part preservative
32.8 parts water
is prepared as described in example 1.
The pigment preparations prepared in the examples above are outstandingly suitable
as inkjet inks. The viscosity remains stable both at room temperature and on
4 weeks of storage at 60°C. The particle size distribution of the pigment is stable
even on storage and under thermal loads. In the inkjet inks, there is no flocculation of
the pigment particles or clogging of the nozzles.
We Claims :
1. An aqueous pigment preparation, comprising an organic and/or inorganic
pigment dispersed in an acrylate resin solution and dispersing aid, wherein the
5 acrylate resin is a copolymer composed essentially of from 50 to 80 mol% of
monoalkenyl aromatics and from 20 to 50 mol% of acrylates and has an average
molar mass Mv of between 1 000 and 50 000 g/mol and wherein the dispersing aid is
a compound of the formula (I)
10 R - O - (CH2-CH2-O)m - CH2 - COOM (I)
in which
R is a C10-C20 alkyl radical or a C10-C20 alkenyl radical,
m is a number from 1 to 15, and
15 M is a monovalent cation.
2. The pigment preparation as claimed in claim 1, wherein the acrylate resin is a
copolymer of from 60 to 70 mol% of monoalkenyl aromatics and from 30 to 40 mol%
of acrylates.
20
3. The pigment preparation as claimed in claim 1 or 2, wherein the acrylate is a
monomer from the group consisting of acrylic acid, methacrylic acid, esters of acrylic
acid, and esters of methacrylic acid.
25 4. The pigment preparation as claimed in at least one of claims 1 to 3, wherein
the acrylate is a methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate,
n-butyl (meth)acrylate, isopropyl (meth)acrylate, isobutyl (meth)acrylate, n-amyl
(meth)acrylate, n-hexyl (meth)aciylate, isoamyl (meth)acrylate, 2-hydroxyethyl
(meth)acrylate, 2-hydroxypropyl (meth)acrylate, N.N-dimethylaminoethyl
(meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, t-butylaminoethyl
(meth)acrylate, 2-sulfoethyl (meth)acrylate, trifluoroethyl (meth)acrylate, glycidyl
(meth)acrylate, benzyl (meth)acrylate, allyl (meth)acrylate, 2-n-butoxyethyl
(meth)acrylate, 2-chloroethyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl
(meth)acrylate, 2-ethylbutyl (meth)acrylate, cinnamyl (meth)acrylate, crotyl
(meth)acrylate, cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, 2-ethoxyethyl
(meth)acrylate, furfuryl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, methallyl
(meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-methoxybutyl (meth)acrylate, 2-
nitro-2-methylpropyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl
(meth)acrylate, 2-phenoxyethyl (meth)acrylale, 2-phenylethyl (meth)acrylate, phenyl
(meth)acrylate, propargyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate and
tetrahydropyranyl (meth)acrylate, or a combination thereof.
5. The pigment preparation as claimed in at least one of claims 1 to 4, wherein
the monoalkenyl aromatic is a monomer from the group consisting of styrene,
a-methylstyrene, vinyltoluene, tert-butylstyrene, and o-chlorostyrene, or a
combination thereof.
6. The pigment preparation as claimed in at least one of claims 1 to 5, wherein
the acrylate resin is composed of the monomers styrene and acrylic acid and/or
methacrylic acid.
7. The pigment preparation as claimed in at least one of claims 1 to 6, wherein
the organic pigment is a monoazo, disazo, laked azo, 8-naphthol, naphthol AS,
benzimidazolone, disazo condensation or azo metal complex pigment or a polycyclic
pigment, especially a phthalocyanine, quinacridone, perylene, perinone, thiazine
indigo, thioindigo, anthanthrone, anthraquinone, flavanthrone, indanthrone,
isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, isoindoline
or diketopyrrolopyrrole pigment or a carbon black.
8. The pigment preparation as claimed in at least one of claims 1 to 7, wherein
the weight ratio between the pigmentand the acrylate resin is from 1:0.05 to 1:1, in
particular from 1:0.2 to 1:0.5.
9. The pigment preparation as claimed in at least one of claims 1 to 8, composed
of
a) from 5 to 50% by weight, preferably from 15 to 25% by weight, of pigment,
b) from 0.25 to 20% by weight, preferably from 1 to 10% by weight, of the
acrylate resin,
c) from 1 to 12% by weight, preferably from 2 to 8% by weight, of a compound of
the formula (I),
d) from 5 to 60% by weight, preferably from 10 to 40% by weight, of water,
e) from 0 to 10% by weight, preferably from 0.1 to 5% by weight, of an organic
solvent,
f) from 0 to 15% by weight, preferably from 5 to 9% by weight, of a hydrotropic
substance,
g) from 0 to 10% by weight, preferably from 0.5 to 9.5% by weight, of further
customary additives,
based in each case on the total weight of the pigment preparation.
10. A process for preparing a pigment preparation as claimed in one or more of
claims 1 to 9, which comprises finely dispersing the pigment in the acrylate resin
solution and the dispersing aid of the formula (I) by means of a dispersing apparatus,
preferably a stirred ball mill, which is operated with a peripheral stirrer speed of more
than 12 m/s, employing nonmetallic grinding media with a diameter of less than or
equal to 1 mm.
11. The pigment preparation as claimed in one or more of claims 1 to 9
as a colorant for printing inks, especially for inkjet inks, electrophotographic toners,
especially addition-polymerization toners, powder coating materials, and color filters.
12. A set of colorant preparations comprising at least one colorant preparation in
each of the colors black, cyan, magenta, and yellow, wherein at least one of the
preparations is an aqueous pigment preparation as claimed in one or more of
claims 1 to 9.
13. A set of colorant preparations as claimed in claim 12, wherein
the colorant of the black colorant preparation is a carbon black, preferably a gas
black or furnace black,
the colorant of the cyan colorant preparation is a pigment from the group of the
phthalocyanine pigments, preferably Colour Index P. Blue 15, P. Blue 15:3 or P. Blue
15:4,
the colorant of the magenta colorant preparation is a pigment from the group of the
quinacridone pigments, preferably a Colour Index P. Red 122 or P. Violet 19, or a
pigment from the group of the monoazo, disazo or benzimidazolone pigments,
preferably a Colour Index P. Red 57:1, P. Red 146, P. Red 176, P. Red 184, P. Red
185 or P. Red 269, and
the colorant of the yellow colorant preparation is a pigment from the group of the
monoazo, disazo or benzimidazolone pigments, preferably Colour Index P. Yellow
17, P. Yellow 74, P. Yellow 83, P. Yellow 97, P. Yellow 120, P. Yellow 128, P. Yellow
139, P. Yellow 151, P. Yellow 155, P. Yellow 180 or P. Yellow 213.
14. A set of colorant preparations as claimed in claim 12 or 13, wherein the
respective colorant preparations are each printing inks, especially inkjet inks.
The invention relates to an aqueous pigment preparation
containing an organic and/or inorganic pigment dispersed in an
acrylatate resin solution and a dispersion agent. The preparation
is characterized in that the acrylate resin is a copolymer
consisting essentially of between 50 and 80 mol % of monoalkenyl
aromatic compounds and between 20 and 50 mon % of acrylates, and
has an average molar Mass Mv of between 1,000 and 50,000 g/mol,
and in that the dispersion agent is a compound of formula (I): R-
0 -(CH2 -CH2 -0)m -CH2 -COOM, wherein R is a C10 -C20 alkyl
radical or a C10 -C20 alkenyl radical, m is a number between 1 and
15, and M is a monovalent cation.

Documents:


Patent Number 223377
Indian Patent Application Number 01676/KOLNP/2003
PG Journal Number 37/2008
Publication Date 12-Sep-2008
Grant Date 10-Sep-2008
Date of Filing 29-Dec-2003
Name of Patentee CLARIANT PRODUKTE (DEUTSCHALND) GMBH
Applicant Address BRUNINGSTRASSE 50, 65929 FRANKFURT AM MAIN
Inventors:
# Inventor's Name Inventor's Address
1 HARZ, ANDREAS HOFHEIMER STRASSE 2A, 65824 SCHWALBACH
2 MACHOLDT, HANS-TOBIAS WALDSTRASSE 20 64297 DARMSTADT-EBERSTADT
3 MENZEL, HEIDEMARIE GLUCKSTRASSE 24 65812 BAD SODEN
4 MULLER, MICHAEL ERLESRING 28 65795 HATTERSHEIM-OKRIFTEL
PCT International Classification Number C09D 17/00
PCT International Application Number PCT/EP02/07794
PCT International Filing date 2002-07-12
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10135140.2 2001-07-19 Germany