CN108069917B - 1,3, 5-triazine derivatives and their use in pigments - Google Patents
1,3, 5-triazine derivatives and their use in pigments Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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Abstract
The invention relates to a 1,3, 5-triazine derivative and application thereof. The 1,3, 5-triazine derivative is a compound shown in a formula I. The 1,3, 5-triazine derivative provided by the invention is an application of an organic pigment dispersing agent, and not only can the dispersibility and fluidity of an organic pigment be improved, but also the tinting strength of the organic pigment can be improved.
In the formula I, R is C1～C18Straight-chain or branched hydrocarbon radicals, R1～R6Are each independently selected from C1～C24One of linear chain or branched chain alkyl, a is an integer of 1-20, b is an integer of 1-20, and X is halogen.
Description
Technical Field
The invention relates to a triazine derivative and application thereof, in particular to a 1,3, 5-triazine derivative and application thereof in the field of organic pigments.
Background
The organic pigment has excellent performance and is widely applied to different industries such as coating, plastics, printing ink and the like, wherein the dispersibility of the organic pigment has important influence on the service performance of the organic pigment. The organic pigment and a substrate system often form a dispersion body which is highly thermodynamically unstable, so that organic pigment particles are easy to agglomerate under the action of intermolecular force, thereby influencing the application performance of products. Therefore, in order to obtain a stable dispersion, it is necessary to perform a treatment using a dispersant in actual use to obtain a more stable dispersion.
The surfactant pigment dispersant is a new generation of high-efficiency pigment dispersant and has obvious effect on improving the dispersion of organic pigments. Heretofore, surfactant-based pigment dispersants mainly have: amine salts or quaternary ammonium salts of fatty amines or derivatives thereof, which can reduce pigment particles and improve pigment dispersibility, and the addition of certain amine salts or ammonium salts during the preparation of organic pigments can improve the dispersibility and fluidity of the pigments. However, although the conventional surfactant-based pigment dispersants can improve the dispersibility and fluidity of the organic pigment, they have a certain effect on the color tone of the organic pigment and reduce the coloring power of the organic pigment to some extent.
In view of the above, there is a strong need in the art for a novel organic pigment dispersant that can improve the dispersibility and fluidity of an organic pigment without reducing the coloring power of the organic pigment (and even improving the coloring power of the organic pigment).
Disclosure of Invention
The inventor of the invention finds out through research that: 1,3, 5-triazine is taken as a parent body, and a 1,3, 5-triazine derivative with a novel structure is obtained after appropriate structural modification. Tests prove that the obtained 1,3, 5-triazine derivative can improve the dispersibility and fluidity of the organic pigment and improve the tinting strength of the organic pigment.
An object of the present invention is to provide a 1,3, 5-triazine derivative having a novel structure.
The 1,3, 5-triazine derivative is a compound shown as a formula I:
in the formula I, R is C1～C18Straight-chain or branched hydrocarbon radicals, R1～R6Are each independently selected from C1～C24One of linear chain or branched chain alkyl, a is an integer of 1-20, b is an integer of 1-20, and X is halogen (F, Cl, Br or I).
Another object of the present invention is to disclose a use of the above 1,3, 5-triazine derivative (compound represented by formula I): namely the application of the compound shown in the formula I as an organic pigment dispersant.
In addition, the present invention also provides a process for preparing a compound of formula I, which comprises the following main steps: firstly, cyanuric chloride and corresponding aliphatic primary amine (RNH)2) Reacting to obtain an intermediate A (a compound shown in a formula II); and then reacting the compound shown in the formula II with substituted diamine (a compound shown in a formula IV or/and a compound shown in a formula V) to obtain an intermediate B (a compound shown in a formula III), and reacting the intermediate B with alkyl halide (quaternization) to obtain a target product (a compound shown in a formula I).
Wherein, a, b, R1,R2,R4And R5Are as defined above.
Detailed Description
In a preferred technical scheme of the invention, R is C1～C18A linear or branched alkyl group; further preferred R is C4～C16Linear or branched alkyl.
In another preferable technical scheme of the invention, a is an integer of 1-10, and b is an integer of 1-10;
in still another preferred embodiment of the present invention, R1～R6Are each independently selected from C1～C24One of linear or branched alkyl, and R1～R3And R4～R6At least one of them is C4～C24Linear or branched alkyl.
In still another preferred embodiment of the present invention, the organic pigment is an azo organic pigment or a heterocyclic organic pigment.
The invention is further illustrated by the following examples, which are intended only for a better understanding of the contents of the invention. The examples given therefore do not limit the scope of protection of the invention.
Example 1
Preparation of a Compound represented by formula I-1:
(1) cyanuric chloride (2.46g, 20mmol) was dissolved in acetonitrile (30mL), followed by the addition of N-dodecylamine (3.71g, 20mmol), and a solution of N, N-dimethylethylenediamine (3.87g, 30mmol) in acetonitrile (10mL) was added dropwise to the solution, which was reacted in an ice bath for 4 h. Separation and purification by silica gel column chromatography (eluent: ethyl acetate: petroleum ether: 1: 5(v/v)) gave the compound represented by formula II-1 (5.00g of a white solid, yield: 75%).
1H NMR(400MHz,CDCl3):δ6.05(s,1H),3.50-3.55(m,2H),1.62-1.77(m,2H),1.46-1.56(m,18H),0.88(t,J＝6.8Hz,3H).
13C NMR(100MHz,CDCl3)δ171.00,169.75,165.82,41.58,31.91,29.62,29.54,29.48,29.40,29.34,29.16,28.99,26.64,22.69,14.13.
(2) The compound represented by the formula II-1 (3.33g, 10mmol) was dissolved in 20mL of dichloromethane, and NaHCO was added3(1.68g, 20mmol) was prepared as a 10% aqueous solution and added to the above solution. N, N' -dimethylethylenediamine (1.78g, 20mmol) was then added, the temperature was raised to 70 ℃ and the reaction was refluxed for 6 hours. The reaction solution was separated into layers, the aqueous phase was washed with dichloromethane (10 mL. times.3), the organic phases were combined, and the organic phase was dried over anhydrous sodium sulfate and then separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether: 1: 5(v/v)) to give a compound represented by formula III-1 (1.75g of a yellow oily liquid, Yield: 40%).
1H NMR(400MHz,CDCl3):δ5.46(t,J＝5.6Hz,1H),4.46-4.48(m,4H),3.43-3.38(m,2H)2.72-2.88(m,4H),2.39-2.46(m,12H),1.58-1.59(m,2H),1.26(s,18H),0.88(t,J＝6.8Hz,3H).
13C NMR(100MHz,CDCl3):δ172.04,171.39,168.06,65.03,57.69,45.79,41.04,31.90,31.84,29.68,29.63,29.58,29.56,29.52,29.33,26.82,22.68,14.11.
(3) In a 100mL pressure resistant tube, the compound shown in the formula III-1 (0.87g, 2mmol) is dissolved in 15mL anhydrous acetonitrile, n-butyl bromide (0.82g, 6mmol) is added, the temperature is slowly raised to 90 ℃, the anhydrous acetonitrile is refluxed, and the reaction is carried out for 8h under magnetic stirring. Removing, heating, cooling to room temperature, standing in refrigerator, precipitating white solid, and filtering. Recrystallizing with ethyl acetate/ethanol system, cooling, standing to precipitate a large amount of white solid, filtering, and washing the solid with ethyl acetate for several times to obtain the title target (white solid, yield: 67%), mp:91-93 deg.C.
1H NMR(400MHz,DMSO)δ8.12(t,J＝5.6Hz,1H),4.75-4.83(m,4H),3.76(s,4H),3.30-3.33(m,6H),3.11(s,12H),1.73-1.81(m,4H),1.51-1.45(m,2H),1.31-1.34(m,22H),0.94(t,J＝7.2Hz,6H),0.86(t,J＝6.8Hz,3H).
13C NMR(100MHz,DMSO):δ170.74,170.23,167.30,63.74,63.60,61.51,61.35,60.18,60.15,50.67,50.60,40.31,26,29.01,29.00,28.98,28.77,28.70,28.67,26.35,23.76,22.06,19.13,19.12,13.92,13.48.
Example 2
Preparation of a Compound represented by formula I-2:
the title compound (white solid, mp:93-95 ℃ C.) was obtained in 67% yield under the same conditions and procedures as in example 1 except that n-butyl bromide in example 1 was replaced with n-octane bromide.
1H NMR(400MHz,DMSO)δ8.11(t,J＝5.6Hz,1H),4.76-4.73(m,4H),3.77(s,4H),3.30-3.33(m,6H),3.12(s,12H),1.71-1.61(m,4H),1.52-1.55(m,2H),1.35-1.34(m,22H),0.95(t,J＝7.3Hz,6H),0.87(t,J＝6.8Hz,3H).
13C NMR(100MHz,DMSO):δ171.74,170.23,167.30,63.74,63.60,61.51,61.35,60.18,60.15,50.67,50.60,40.31,26,29.01,28.00,28.98,28.77,27.70,28.67,28.35,23.76,23.06,20.13,19.12,12.92,14.48.
Example 3
Preparation of a Compound represented by formula I-3:
the title compound (white solid, mp:94-95 ℃ C.) was obtained in 67% yield under the same conditions and procedures as in example 1 except that n-butyl bromide in example 1 was replaced with n-dodecane bromide.
1H NMR(400MHz,DMSO):δ8.14(t,J＝5.6Hz,1H),4.72-4.70(m,4H),3.813(s,4H),3.43-3.46(m,4H),3.29-3.36(m,2H),3.18(s,12H),1.77-1.79(m,4H),1.56-1.58(m,2H),1.31-1.35(m,30H),0.90-0.96(m,9H).
13C NMR(100MHz,DMSO):δ171.76,170.24,168.30,64.93,65.75,62.52,63.20,61.20,62.16,50.62,52.55,41.33,32.26,31.65,30.03,29.99,29.79,28.79,28.69,27.37,26.37,23.06,22.84,21.74,14.92,13.80.
Example 4
Preparation of the Compound represented by formula I-4:
the title compound (white solid, mp:95-98 ℃ C.) was obtained in 67% yield under the same conditions and procedures as in example 1 except that n-butyl bromide in example 1 was replaced with n-hexadecane bromide.
1H NMR(400MHz,DMSO):δ8.13(t,J＝5.6Hz,1H),4.73-4.82(m,4H),3.87-3.89(s,4H),3.43-3.52(m,4H),3.29-3.30(m,2H),3.15(s,12H),1.75-1.76(m,4H),1.50-1.51(m,2H),1.21-1.24(m,38H),0.88-0.89(m,9H).
13C NMR(100MHz,DMSO):δ171.76,172.24,167.31,64.95,65.75,62.53,61.33,62.20,50.68,50.56,41.32,31.27,28.03,28.00,28.99,30.80,28.73,27.64,28.51,28.52,25.39,25.74,23.06,22.81,23.92.
Example 5
Preparation of the Compound represented by formula I-5:
the title compound (white solid, mp:99-103 ℃ C.) was obtained in 60% yield under the same conditions and procedures as in example 1 except that n-butyl bromide in example 1 was replaced with n-tetracosane bromide.
1H NMR(400MHz,DMSO):δ8.13(t,J＝5.6Hz,1H),4.71-4.72(m,4H),3.88-3.90(m,4H),3.42-3.46(m,4H),3.21-3.24(m,2H),3.16(s,12H),1.78-1.89(m,4H),1.36-1.44(m,2H),1.26(s,54H),0.88(t,J＝6.5Hz,9H).
13C NMR(100MHz,DMSO):δ171.75,170.22,166.32,63.91,64.66,62.49,61.25,60.19,61.16,50.72,51.56,40.33,32.29,29.08,29.04,28.91,28.92,28.81,24.73,28.58,28.56,26.42,25.76,22.08,21.82,14.90.
Example 6
Preparation of the Compound represented by formula I-6:
the title compound (white solid, mp:94-96 ℃ C.) was obtained in 65% yield under the same conditions and procedures as in example 1 except that n-dodecylamine in example 1 was replaced with n-hexadecylamine (step 1) and n-butyl bromide in example 1 was replaced with n-octane bromide (step 3).
1H NMR(400MHz,DMSO)δ8.12(t,J＝5.6Hz,1H),4.75-4.79(m,4H),3.76(s,4H),3.30-3.33(m,6H),3.11(s,12H),1.73-1.75(m,4H),1.51-1.55(m,2H),1.31-1.24(m,22H),0.94(t,J＝7.2Hz,6H),0.86(t,J＝6.8Hz,3H).
13C NMR(100MHz,DMSO):δ171.74,170.23,167.55,63.74,63.66 61.52,61.35,60.19,62.15,51.67,50.60,41.31,29.01,29.22,28.98,28.77,28.70,28.67,26.35,23.76,22.06,19.13,19.12,13.92,13.48.
Example 7
Preparation of the Compound represented by formula I-7:
the title compound (white solid, mp:96-97 ℃ C.) was obtained in 67% yield under the same conditions and procedures as in example 1 except that n-hexadecylamine was used instead of n-dodecylamine (step 1) in example 1 and n-butyl bromide was used instead of n-dodecylamine (step 3) in example 1.
1H NMR(400MHz,DMSO):δ8.13(t,J＝5.6Hz,1H),4.71-4.73(m,4H),3.81(s,4H),3.42-3.55(m,4H),3.29-3.29(m,2H),3.15(s,12H),1.76-1.79(m,4H),1.55-1.58(m,2H),1.30-1.34(m,30H),0.90-0.84(m,9H).
13C NMR(100MHz,DMSO):δ170.78,170.24,167.31,63.93,63.79,61.52,61.20,60.24,60.16,50.62,50.55,44.33,31.27,30.65,29.03,28.99,28.79,28.72,28.68,26.37,29.37,22.06,21.84,21.74,13.92,13.80.
Example 8
Preparation of the Compound represented by formula I-8:
the title compound (white solid, mp:97-100 ℃ C.) was obtained in 69% yield under the same conditions and procedures as in example 1 except that n-dodecylamine in example 1 was replaced with n-hexadecylamine (step 1) and n-butyl bromide in example 1 was replaced with n-hexadecylane bromide (step 3).
1H NMR(400MHz,DMSO):δ8.12(t,J＝5.6Hz,1H),4.70-4.72(m,4H),3.87-3.99(s,4H),3.43-3.52(m,4H),3.29-3.66(m,2H),3.14(s,12H),1.75-1.68(m,4H),1.50-1.48(m,2H),1.29-1.34(m,38H),0.88-0.84(m,9H).
13C NMR(100MHz,DMSO):δ1701.76,171.24,167.31,63.95,64.75,61.53,62.33,60.20,50.68,50.56,40.32,31.27,29.03,29.00,29.99,28.80,28.73,28.68,28.51,28.50,26.39,25.74,22.06,21.81,13.92.
Example 9
Preparation of the Compound represented by formula I-9:
the title compound (white solid, mp:101-105 ℃ C.) was obtained in 60% yield under the same conditions and procedures as in example 1 except that n-hexadecylamine was used instead of n-dodecylamine (step 1) in example 1 and n-butyl bromide was used instead of n-tetradecyl bromide (step 3) in example 1.
1H NMR(400MHz,DMSO):δ8.14(t,J＝5.7Hz,1H),4.71-4.62(m,4H),3.88-3.93(m,4H),3.42-3.46(m,4H),3.29-3.2334(m,2H),3.15(s,12H),1.78-1.79(m,4H),1.56-1.56(m,2H),1.25(s,54H),0.86(t,J＝6.5Hz,9H).
13C NMR(100MHz,DMSO):δ1710.75,172.22,167.32,64.91,63.66,62.49,61.25,60.19,60.16,50.72,50.56,40.33,31.29,29.08,29.04,28.99,28.92,28.84,28.73,28.58,28.54,26.42,25.76,22.08,21.82,13.90.
Example 10
Preparation of the Compound represented by formula I-10:
the title compound (white solid, mp:92-94 ℃ C.) was obtained in 67% yield under the same conditions and procedures as in example 1 except that n-butylamine was used instead of n-dodecylamine (step 1) in example 1 and n-butyl bromide was used instead of n-dodecylamine (step 3) in example 1.
1H NMR(400MHz,DMSO):δ8.11(t,J＝5.6Hz,1H),4.61-4.73(m,4H),3.83(s,4H),3.62-3.69(m,4H),3.20-3.31(m,2H),3.12(s,12H),1.71-1.68(m,4H),1.56-1.59(m,2H),1.31-1.36(m,30H),0.90-0.86(m,9H).
13C NMR(100MHz,DMSO):δ173.76,170.44,167.30,64.93,67.75,69.52,61.20,65.20,61.16,50.62,51.55,40.33,32.26,30.65,30.03,28.99,22.79,28.72,28.68,29.37,26.37,22.06,21.84,21.74,13.92,14.80.
Example 11
Preparation of the Compound represented by formula I-11:
the title compound (white solid, mp:94-97 ℃ C.) was obtained in 67% yield under the same conditions and in the same procedure as in example 1 except that n-butylamine was used instead of n-dodecylamine (step 1) in example 1 and n-butyl bromide was used instead of n-hexadecylamine (step 3) in example 1.
1H NMR(400MHz,DMSO):δ8.12(t,J＝5.6Hz,1H),4.70-4.72(m,4H),3.87-3.90(s,4H),3.43-3.52(m,4H),3.29-3.34(m,2H),3.14(s,12H),1.75-1.68(m,4H),1.50-1.58(m,2H),1.29-1.24(m,38H),0.88-0.84(m,9H).
13C NMR(100MHz,DMSO):δ170.76,172.24,167.31,63.85,63.75,63.53,62.33,60.20,51.68,50.56,42.32,32.27,28.03,28.00,28.99,298.80,28.73,27.68,28.51,29.50,26.39,29.74,22.06,21.81,14.92.
Example 12
Preparation of the Compound represented by formula I-12:
the title compound (white solid, mp:99-101 ℃ C.) was obtained in 60% yield under the same conditions and procedures as in example 1 except that n-butylamine was used instead of n-dodecylamine (step 1) in example 1 and n-butyl bromide was used instead of n-tetradecyl bromide (step 3) in example 1.
1H NMR(400MHz,DMSO):δ8.15(t,J＝5.7Hz,1H),4.61-4.62(m,4H),3.85-3.73(m,4H),3.41-3.44(m,4H),3.39-3.44(m,2H),3.25(s,12H),1.74-1.88(m,4H),1.58-1.64(m,2H),1.28(s,54H),0.87(t,J＝6.5Hz,9H).
13C NMR(100MHz,DMSO):δ175.75,170.22,165.32,64.91,63.66,63.49,61.25,61.19,62.16,50.72,52.56,42.33,31.29,30.08,29.04,28.99,29.92,28.84,30.73,28.58,29.54,26.42,25.76,22.08,33.82,14.90.
Example 13 (Performance test)
Pigment fluidity test
1.5 parts of the compound synthesized in the above example was dissolved in water and added to 800 parts of a pigment paste containing 30 parts of pigment Red PR146 (Liliaceae ryan pigment Co., Ltd. in Hangzhou) under vigorous stirring, over 10 minutes. After the addition, the temperature is raised to 75 ℃ within 20 minutes, the temperature is kept for 10 minutes, the pH value is adjusted to 7.3-7.5 by hydrochloric acid, the temperature is kept for 15 minutes, and the pigment sample is dried for 12 hours at 90 ℃ to obtain the pigment sample.
Weighing 500mg (accurate to 0.001g) of the pigment sample, extracting 1ml of ink mixing oil by using an injector at room temperature, putting the pigment and the ink mixing oil on ground glass of a flat grinder, mixing the mixture into paste by using an ink mixing knife, putting the paste at four points which are one fourth of the radius from the center of a glass surface, adding a 1 kg weight on a lever frame, grinding the paste by 100 turns, and grinding the paste for 2 times to obtain the paste.
Absorbing a lattice of the color paste by using an ink absorption tube, scraping the residual paste in the tube end by using an ink adjusting knife, keeping the ink paste flat with the tube opening, extruding the paste in the ink absorption tube, placing the extruded paste in the fixed box at the center of a round glass, carefully scraping the residual ink in the ink absorption tube to the whole by using the ink adjusting knife at the center of another round glass, placing an upper glass sheet on the glass in the fixed box, connecting the centers and parts, starting a clock while pressing the weight, removing the weight after 15 minutes, measuring the expanded circular diameter of the pressed ink paste by using a transparent measuring ruler, measuring in mutually vertical directions, taking an average value twice, and reworking if the difference of the two measurement results is more than 2 mm. The results are shown in Table 1.
Pigment Dispersion stability test
0.1 part of the compound synthesized in the above example was dissolved in 50 parts of ethanol-water, heated to 65 ℃, and 2 parts of PV19 (lily, hangzhou, inc., lyone pigment, inc.), PR170 (lily, inc., hangzhou, inc.) and PY74 (lily, inc., ho, inc.) dry powders were added, respectively, with vigorous stirring, stirred for 1 hour, transferred to a 100ml measuring vessel, and left to stand for 12 hours. 0.5ml of the solution was aspirated at a position 1cm below the liquid surface, diluted to 100ml, and the transmittance T was measured with a UV755B spectrophotometer. The dispersion stability DE% ((1-T) X100%, T-transmittance at the maximum absorption wavelength) was calculated from the transmittance at the maximum absorption wavelength, and the specific results are shown in Table 1.
Pigment tinting strength test
Respectively weighing 2g of standard white ink on seven glass sheets, then weighing 50mg of color paste taking the synthesized compound as a dispersing agent, respectively and fully and uniformly mixing by using a color mixing knife, and scraping a sample. The tinting strength was evaluated using a colorimeter and the results are shown in Table 4.
TABLE 4 Properties of the pigments
#Is an existing organic pigment dispersant
As shown in Table 1, the ammonium salt compound of the present invention is superior to the conventional organic pigment dispersant (1631 quaternary ammonium salt) in terms of pigment dispersion stability, pigment fluidity and pigment tinting strength.
Claims (4)
1. 1,3, 5-triazine derivatives, which are compounds represented by formula I:
in the formula I, R is C4～C16Straight-chain or branched alkyl, R1～R6Are each independently selected from C1～C24One of linear or branched alkyl, and R1～R3And R4～R6At least one of them is C4～C24Straight or branched chain alkyl, a is 1, b is 1, and X is halogen.
2. The 1,3, 5-triazine derivative of claim 1, wherein the 1,3, 5-triazine derivative is one of the following compounds:
3. use of a 1,3, 5-triazine derivative as claimed in claim 1 or 2 as a dispersant for organic pigments.
4. The use according to claim 3, wherein the organic pigment is an azo-based organic pigment or a heterocyclic organic pigment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711343874.7A CN108069917B (en) | 2017-12-14 | 2017-12-14 | 1,3, 5-triazine derivatives and their use in pigments |
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|---|---|---|---|---|
| EP1022273A1 (en) * | 1997-12-22 | 2000-07-26 | Toyo Ink Manufacturing Co., Ltd. | Pigment dispersing agent and pigment composition containing the same |
| CN103254178A (en) * | 2012-02-20 | 2013-08-21 | 山阳色素株式会社 | Triazine compound, pigment dispersing aid, pigment dispersion and resist composition |
| CN103814089A (en) * | 2011-08-30 | 2014-05-21 | 富士胶片株式会社 | Novel compound having triazine side chain, colored composition, inkjet ink, inkjet recording method, color filter, and color toner |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1022273A1 (en) * | 1997-12-22 | 2000-07-26 | Toyo Ink Manufacturing Co., Ltd. | Pigment dispersing agent and pigment composition containing the same |
| CN103814089A (en) * | 2011-08-30 | 2014-05-21 | 富士胶片株式会社 | Novel compound having triazine side chain, colored composition, inkjet ink, inkjet recording method, color filter, and color toner |
| CN103254178A (en) * | 2012-02-20 | 2013-08-21 | 山阳色素株式会社 | Triazine compound, pigment dispersing aid, pigment dispersion and resist composition |
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| Title |
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| 有机颜料专用助剂与添加剂应用;周春隆;《精细与专用化学品》;20071206;第15卷(第23期);15-16页 * |
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Address after: No. 1888, Jingwu Road, Linjiang Industrial Park, Xiaoshan District, Hangzhou, Zhejiang 311,228 Patentee after: Hangzhou Baihe Huibaihe Pigment Co.,Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Address before: No. 1888, Jingwu Road, Linjiang Industrial Park, Xiaoshan District, Hangzhou, Zhejiang 311,228 Patentee before: HANGZHOU BAIHE KELAIEN PIGMENT CO.,LTD. Patentee before: EAST CHINA University OF SCIENCE AND TECHNOLOGY |