Pyridone Dye Composition
20170018599 ยท 2017-01-19
Assignee
Inventors
Cpc classification
C09B29/3626
CHEMISTRY; METALLURGY
H10K59/38
ELECTRICITY
G02B5/223
PHYSICS
International classification
G02F1/1335
PHYSICS
Abstract
The invention relates to a colorant composition comprising at least one compound of the formula (I) and at least one pigment, in which the compounds of the formula (I) have the following formula:
##STR00001##
in which R.sup.0 is C.sub.1-C.sub.6-alkyl or CF.sub.3; R.sup.1 is sulfo, carboxyl, C.sub.1-C.sub.4-alkylenesulfo, C.sub.1-C.sub.4-alkylenecarboxy, CONH.sub.2, CONH(C.sub.1-C.sub.4-alkyl) or CN, R.sup.2 is C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, hydroxy-C.sub.1-C.sub.18-alkyl, or (C.sub.1-C.sub.6-alkylene-O).sub.mR where R is defined as H, C.sub.1-C.sub.16-alkyl or hydroxy-C.sub.1-C.sub.16-alkyl and m is a number from 1 to 20, R.sup.3 is H, sulfo, carboxyl, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, R.sup.4 is H, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, R.sup.5 is OH, OM, C.sub.1-C.sub.6-alkyl, unsubstituted C.sub.6-C.sub.10-aryl or C.sub.1-C.sub.6-alkyl-, halogen- (e.g. F, Cl, Br), carboxyl- or sulfo-substituted C.sub.6-C.sub.10-aryl,
where the compounds of the formula (I) contain at least one anionic radical from the group of sulfo and carboxyl having the countercation M.sup.+, where M.sup.+ is an alkali metal cation or an organic cation.
The colorant compositions are especially suitable for use in color filters.
Claims
1. A colorant composition comprising at least one compound of the formula (I) and at least one pigment, wherein the at least one compound of the formula (I) has the following formula: ##STR00054## R.sup.0 is C.sub.1-C.sub.6-alkyl or CF.sub.3; R.sup.1 is sulfo, carboxyl, C.sub.1-C.sub.4-alkylenesulfo, C.sub.1-C.sub.4-alkylenecarboxy, CONH.sub.2, CONH(C.sub.1-C.sub.4-alkyl) or CN, R.sup.2 is C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, hydroxy-C.sub.1-C.sub.18-alkyl, or (C.sub.1-C.sub.6-alkylene-O).sub.mR, wherein R is H, C.sub.1-C.sub.16-alkyl or hydroxy-C.sub.1-C.sub.16-alkyl and m is a number from 1 to 20, R.sup.3 is H, sulfo, carboxyl, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, R.sup.4 is H, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy, R.sup.5 is OH, OM, C.sub.1-C.sub.6-alkyl, unsubstituted C.sub.6-C.sub.10-aryl or C.sub.1-C.sub.6-alkyl-, halogen-, carboxyl- or sulfo-substituted C.sub.6-C.sub.10-aryl, wherein the at least one compound of the formula (I) contains at least one anionic radical from the group of sulfo and carboxyl having the countercation M.sup.+, wherein M.sup.+ is an alkali metal cation or an organic cation.
2. The colorant composition as claimed in claim 1, wherein the at least one compound of the formula (I) contains at least one sulfo group having the countercation M.sup.+.
3. The colorant composition as claimed in claim 1, wherein the countercation M.sup.+ is an organic ammonium cation or an organic phosphonium cation.
4. The colorant composition as claimed in claim 3, wherein the organic ammonium cation is a primary, secondary, tertiary or quaternary ammonium cation.
5. The colorant composition as claimed in claim 3, wherein the organic ammonium cation is an imidazolium cation, alkylguanidinium cation, benzotriazolyl cation or pyridinium cation.
6. The colorant composition as claimed in claim 1, wherein the at least one pigment is an organic pigment.
7. The colorant composition as claimed in claim 1, wherein the at least one organic pigment is selected from the group consisting of anthraquinone pigments, laked or unlaked azo pigments, anthanthrone pigments, benzimidazolone pigments, quinacridone pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, dioxazine pigments, disazo condensation pigments, isoindolinone pigments, isoindoline pigments, metal complex pigments, perinone pigments, perylene pigments, phthalocyanine pigments and triarylcarbonium pigments.
8. The colorant composition as claimed in claim 1, wherein the mixing ratio of the at least one compound of the formula (I) to the at least one pigment is from 1:99 to 99:1 parts by weight.
9. The colorant composition as claimed in claim 1, wherein the at least one compound of the formula (I) is present in an amount of 1% to 20% by weight, based on the total weight of the colorant composition.
10. A millbase comprising 0.01% to 45% by weight of a colorant composition as claimed in claim 1, dispersed in at least one organic solvent.
11. A binder-containing colorant dispersion comprising 0.01% to 40% by weight of a colorant composition as claimed in claim 1, dispersed in at least one organic solvent, at least one polymeric binder and, optionally, further auxiliaries.
12. A process for producing a colorant composition as claimed in claim 1, comprising the step of combining the at least one compound of the formula (I) and the at least one pigment with one another.
13. A high molecular weight organic material of natural or synthetic origin comprising at least one colorant composition as claimed in claim 1.
14. A colored color filter, a colored crystal colored OLED display or a colored bulk polymer comprising a high molecular weight organic material of natural or synthetic origin as claimed in claim 13.
Description
EXAMPLES
Preparation of the Acid Azo Dye (I a)
[0148] ##STR00011##
[0149] A suspension consisting of 17.1 g of 4-aminophenyl methyl sulfone (0.10 mol) in 100 mL of water and 22 mL of conc. hydrochloric acid (37% by weight) is diazotized at 0-5 C. with 17.3 g of sodium nitrite solution (40% by weight; 0.1 mol of NaNO.sub.3). The resultant diazonium salt is added in portions at 0 to 5 C. to a suspension consisting of 24.6 g (0.1 mol) of the compound of the following formula
##STR00012##
in 9 mL of 30% sodium hydroxide solution and 50 mL of water. By adding 15% by weight sodium carbonate solution, the pH is kept at 7 to 9. The volume of the dye suspension is made up to about 700 mL with water, then the mixture is heated to 90 C. for 30 min. After cooling, the solids are filtered off with suction, washed with water and dried under reduced pressure. This gives 40.2 g of a yellow dye powder of the formula (I a).
Preparation of the Hexaalkylguanidinium Chloride (C2a)
[0150] ##STR00013##
[0151] To a solution of 15.5 mL (0.13 mol) of tetramethylurea in 60 mL of toluene are added dropwise, at 60-65 C., 13 mL (0.13 mol) of phosphoryl chloride. After stirring for two hours, the mixture is cooled and, at 0-5 C., a mixture of 18 mL of triethylamine and 40 mL (0.14 mol) of bis(2-ethylhexyl)amine in 30 mL of toluene is added dropwise. Subsequently, the temperature is allowed to rise to about 20 C., and stirring is continued overnight. Then the pale yellow mixture is admixed with 54 mL of NaOH (30% by weight) while cooling. The mixture is stirred together with 150 mL of NaCl solution. The toluene phase is separated off and dried with magnesium sulfate, and the solvent is removed under reduced pressure. This gives 47 g of a pale beige, waxy solid.
Preparation of the Hexaalkylguanidinium Dye Salt (I b)
[0152] ##STR00014##
[0153] 27.5 g (66 mmol) of the hexaalkylguanidinium chloride (C2a) are dissolved at 90 C. in 500 mL of water while stirring (solution A).
[0154] 29.2 g (64 mmol) of the yellow acid azo dye of the formula (I a) are introduced into 500 mL of water and, after the addition of five drops of 15% by weight sodium carbonate solution, heated to 60 to 65 C. This suspension is added in portions at about 90 C. to solution A. After one hour of reaction time at this temperature, an emulsion is obtained, which is cooled, and then the water phase is decanted off. The oily organic phase is taken up with 350 mL of methoxypropyl acetate, dried with magnesium sulfate and stored at 4 C. for one night. After the precipitated solid has been filtered off, the solvent is removed under reduced pressure and the resultant residue is dried to constant weight.
[0155] The dyes in table 1 were obtained by an analogous procedure.
[0156] For the dye anion of example I l, rather than 4-aminophenyl methyl sulfone, an equivalent amount of 4-aminophenyl p-tolyl sulfone is used. For the dye anions of examples I m to I p, rather than 4-aminophenyl methyl sulfone, an equivalent amount of 4-aminophenylsulfonic acid is used.
TABLE-US-00001 TABLE 1 (dye salts prepared) No.: Countercation M.sup.+ Dye anion I a Na.sup.+
[0157] Each of these are yellow substances having breakdown points >200 C.
[0158] Further dye anions were prepared proceeding from the following nitrilopyridones:
##STR00046##
[0159] They are obtainable from methyl cyanoacetate, methyl acetoacetate and the corresponding aminemethoxypropylamine or Jeffamine M600. The nitrile group can be removed by heating with dilute sulfuric acid. The resultant 3,5-unsubstituted pyridones are reacted with formaldehyde and sodium bisulfite by a known procedure (analogously to DE 2162858), giving the following pyridone coupling agents:
##STR00047##
[0160] These were used to obtain the dyes I q and I s. The reaction of the Na dye salts mentioned with the respective quaternary ammonium compounds analogously to the preparation of I b gave the dye salts I r and I t therefrom.
TABLE-US-00002 No.: Countercation M.sup.+ Dye anion I q Na.sup.+
[0161] Examples of the production of the compositions of the invention, comprising dyes I and organic pigments:
Example Z1
Composition Z1
[0162] 2.0 g of compound (I a) are ground together with 18.0 g of C.I. Pigment Yellow 138 in an IKA laboratory powder mill. After discharge from the mill, 19.4 g of composition Z1 of the invention are obtained in the form of a greenish-yellow powder.
Examples Z2 to Z6
[0163] Analogously to example Z1, in place of compound I a, the dyes listed in table 3 below were used. The compositions Z2 to Z6 of the invention are obtained in each case.
TABLE-US-00003 TABLE 3 Example Dye Pigment Z1 I a C.I. Pigment Yellow 138 Z2 I d C.I. Pigment Yellow 138 Z3 I b C.I. Pigment Yellow 138 Z4 I g C.I. Pigment Yellow 138 Z5 I l C.I. Pigment Yellow 138 Z6 I o C.I. Pigment Yellow 138
Example Z7
[0164] The procedure is as in example Z3, except that C.I. Pigment Green 36 rather than C.I. Pigment Yellow 138 is used, and the composition Z7 of the invention is obtained as a yellowish-green solid.
Example Z8
[0165] The procedure is as in example Z1, except that compound (I n) rather than compound (I a) and C.I. Pigment Green 58 rather than C.I. Pigment Yellow 138 are used, and the composition Z8 of the invention is obtained as a yellowish-green solid.
Example Z9
[0166] The procedure is as in example Z3, except that C.I. Pigment Red 254 rather than C.I. Pigment Yellow 138 is used, and the composition Z9 of the invention is obtained as a red solid.
TABLE-US-00004 TABLE 4 Example Dye Pigment Z7 I b C.I. Pigment Green 36 Z8 I n C.I. Pigment Green 58 Z9 I b C.I. Pigment Red 254
Use Example 10
[0167] 10.0 g of the composition according to example Z1 are mixed in a paint shaker cup with 72.5 g of methoxypropyl acetate (PGMEA), 5.0 g of n-butanol and 12.5 g of Disperbyk 2001 (BYK-Chemie, polymeric dispersing aid solution) while stirring. After adding 250 g of zirconia beads (0.3 mm), dispersion is effected in a Lau dispersing unit (Dispermat) for three hours. The resultant millbase is separated from the beads by filtration. The viscosity of the millbase is measured (Haake RheoStress 1 rotary viscometer, cone-plate measurement geometry, 23 C., linear rise in shear rate D to 250 1/s, value determined at 250 1/s).
[0168] 20.0 g of the resultant millbase are mixed with 20.5 g of a 10% by weight solution of Joncryl 611 (styrene-acrylate resin, BASF AG) in PGMEA by shaking without beads for 10 minutes. Then the dispersion is filtered.
[0169] The resultant binder-containing colorant dispersion is applied with the aid of a spin-coater (POLOS Wafer Spinner) to glass plates (SCHOTT, laser-cut, 1010 cm), in a layer thickness which enables setting, in the case of use of a C light source, of the color coordinates y specified in Table 5a or the color coordinates x specified in Table 5b as reference values.
[0170] The layer thickness in each case is about 1 to 2 micrometers.
[0171] The glass plates are left to flash off and then dried at 80 C. in an air circulation drying cabinet (from Binder) for 10 min. The so-called prebake values of the color coordinates (x, y, Y, and CIELAB, Spectrophotometer Datacolor 650, illuminant C, 2 observer), transmission curves (ditto) and contrast values (Tsubosaka CT-1 Contrast Tester) of the glass plates were analyzed. The glass plates are subsequently subjected to a heat treatment in an air circulation drying cabinet at 230 C. for 1 h and analyzed again, from which the postbake values are obtained.
Comparative Examples: C1-C4
[0172] The millbases and color dispersions are produced analogously to the case of use example 10. However, no pigment compositions of the invention are used, but rather the underlying base pigments.
[0173] Tables 5a and 5b show the results of the inventive examples and the comparative examples in the postbake.
[0174] The relative contrast ratio CR is based on the color dispersion of the respective comparative example (100%).
[0175] The values x, y and Y refer to the measured color coordinates in the CIE-Yxy standard color space, where Y is a measure of brightness.
[0176] Each inventive composition was compared with the corresponding base pigment. For the contrast value, the contrast value for each base pigment from the comparative example was set to 100%. For the comparison of the brightnesses Y, the difference Y.sub.exampleY.sub.comparative example was formed in each case. If this value is >0, the brightness of the sample of the invention is greater than that of the comparative example.
[0177] For the comparison of the viscosities, the viscosity for each comparative example was set to 100%.
TABLE-US-00005 TABLE 5a (Reference to y values). Relative viscosity of the millbase y Relative CR Example Description [%] (ref.) = x = Y value [%] 10 Z1 83 0.500 0.428 +2.7 185 11 Z2 83 0.500 0.428 +2.7 185 12 Z3 40 0.500 0.429 +4.5 253 13 Z4 53 0.500 0.430 +3.1 177 14 Z5 38 0.500 0.427 +4.6 267 15 Z6 95 0.500 0.431 +1.3 117 C1 C.I. Pigment 100 0.500 0.435 0 (ref.) 100 Yellow 138 16 Z7 20 0.420 0.255 +0.9 103 C2 C.I. Pigment 100 0.420 0.248 0 (ref.) 100 Green 36 17 Z8 85 0.500 0.283 +2.0 107 C3 C.I. Pigment 100 0.500 0.260 0 (Ref.) 100 Green 58
TABLE-US-00006 TABLE 5b (Reference to x values). Relative viscosity of Use the millbase Relative CR example Description [%] y = x = (ref.) Y value [%] 18 Z9 8 0.317 0.620 +0.5 126 C4 C.I. Pigment 100 0.314 0.620 0 100 Red 254
[0178] The millbases of the compositions of the invention have reduced viscosities compared to those of the untreated pigments. The inventive examples, in the color filter application, show increased brightness Y and an improved contrast value. They have steeper transmission curves.
[0179] Example of the production of a micronized colorant composition by addition during a salt kneading operation:
Example K1
[0180] In a laboratory kneader (Werner & Pfleiderer, 300 mL), 2.0 g of compound (I b) are kneaded with 18.0 g of commercial C.I. Pigment Yellow 138 with addition of 120 g of sodium chloride and 25 mL of diethylene glycol at a temperature of 80 C. for 18 h. The kneaded dough is stirred in 0.9 L of water for two hours and the composition is then filtered. The filtercake is treated again by stirring with 0.9 L of demineralized water for 1 h. After filtration, the colorant composition is washed with water and dried under reduced pressure.
[0181] This gives a greenish-yellow pigment composition K1 in a fine state of subdivision.
Comparative Example KC1
[0182] A salt kneading operation in which 20.0 g of commercial C.I. Pigment Yellow 138 are kneaded with 120 g of sodium chloride and 25 mL of diethylene glycol at a temperature of 80 C. for 18 h is conducted. The kneaded dough is stirred in 0.9 L of water for two hours and the composition is then filtered. The filtercake is treated again by stirring with 0.9 L of demineralized water for 1 h. After filtration, the colorant composition is washed with water and dried under reduced pressure.
Example K2
[0183] The procedure is as in example K1, except that dye (I d) rather than (I b) is used, and the micronized colorant composition K2 is obtained (greenish yellow).
Example K3
[0184] The procedure is as in example K1, except that dye (I r) rather than (I b) is used, and the micronized composition K3 is obtained (greenish yellow).
Application Testing of Examples K1-3 and KC1
[0185] The micronized compositions are tested in analogy to use example 10. However, in place of composition Z1, the compositions specified in table 6 below are used.
TABLE-US-00007 TABLE 6 (Reference to y values). Relative contrast x = Relative value Example Description y = (ref.) Y value [%] K1 micronized composition K1 0.500 0.425 +4.2 280 K2 micronized composition K2 0.500 0.423 +3.2 167 K3 micronized composition K3 0.500 0.422 +3.7 190 KV1 micronized C.I. Pigment 0.500 0.432 0 100 Yellow 138
[0186] The micronized compositions K1-K3 of the invention have a higher contrast value and higher brightness Y than each analogous salt-kneaded pure pigment.