CN110577497B - Indanthrone quaternary ammonium salt compound and preparation method and application thereof - Google Patents
Indanthrone quaternary ammonium salt compound and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an indanthrone quaternary ammonium salt compound, the structural formula of which is shown as a general formula B:
the definition of each substituent is detailed in the specification. The indanthrone quaternary ammonium salt compound has good electroplating performance, the quaternary ammonium salt structure can have larger coverage area on the surface of an electrode through nitrogen positive ions in the structure, namely quaternization centers, can increase cathode polarization, inhibits copper deposition so as to enable electroplating particles to be finer and enable a copper-plated layer to obtain high preferred crystal orientation, and can be used as a quaternary ammonium salt leveling agent for acid copper electroplating.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to an indanthrone (pigment blue 60) quaternary ammonium salt compound, and a preparation method and application thereof.
Background
With the increasingly higher requirements of consumer electronics on portability and the gradual popularization of intelligent wearable devices, printed circuit boards have higher requirements on miniaturization, lightness, thinness, high integration and installation flexibility. The PCB is used as a carrier of chips, various electronic components, and conductive circuits, and must be developed toward high integration, high frequency, and high reliability. In 2006, the total value of the PCB industry in China surpasses Japan and becomes the first world for PCB production and manufacture globally, in 2015, the total value of the PCB in China is 300 hundred million dollars and occupies 45 percent of the total value globally, but the characteristics in China are large and not strong. The printed circuit industry in China is mainly based on low-end products, and most high-end products with high profit added value, high technological content and high precision need to be imported from foreign countries.
The printed circuit boards are mainly classified into five major categories according to the base material, including paper-based printed circuit boards, glass cloth-based printed circuit boards, synthetic fiber printed circuit boards, ceramic-based printed circuit boards, and metal core-based printed circuit boards, and specifically include phenol-formaldehyde paper-based printed circuit boards, epoxy glass cloth printed circuit boards, epoxy synthetic fiber printed circuit boards, and the like. The printed circuit boards are mainly classified into three types according to the structure classification, wherein the three types comprise a rigid printed circuit board, a flexible printed circuit board and a rigid-flex printed circuit board; specifically, the printed wiring board includes a single-sided printed wiring board, a double-sided printed wiring board, a multilayer printed wiring board, and the like.
The acid copper electroplating process for printed circuit boards is developed at a high speed with the high functionality and miniaturization of electronic products. Electroplating, in short, refers to the technique of depositing a smooth surface of a metal, alloy or composite material firmly bonded to a conductive substrate (e.g. metal) by electrolytic reaction under the action of external direct current, such as copper electroplating in the printed circuit board industry, which utilizes CuSO 4 As electrolyte solution, the printed circuit board is connected with the negative pole of the power supply, and the positive pole of the power supply is connected with the phosphorus-containing copper ball. After the power is switched on, the cathode generates a reduction reaction, the metallic copper enters the plating solution in the form of divalent copper ions and continuously migrates to the cathode, and finally electrons obtained on the cathode are reduced into the metallic copper to gradually form the required metallic copper plating layer.
The study of acidic copper plating additives began in the early 20 th century, but was less systematic until the 40 s. In 1996, chern et al performed more detailed modeling of the via plating process and studied the current distribution and leveler effect in the via during the plating process in more detail. With the development of PCB drilling technology and circuit design, the thickness-diameter ratio of the through hole is gradually increased, and the electroplating filling process of the blind hole and the through hole appears. In 2005, kim et al studied the superfilling process of copper on different substrates, achieving superfilling in blind vias with large aspect ratios. In 2010, kondo et al used an additive system containing accelerators, suppressors and levelers to achieve rapid via filling. The relatively large-scale research on PCB through hole copper plating additives in China is later than that in foreign countries, but through efforts, good results have been achieved. In 1977, the chemical system Chenshiming of Guizhou university synthesizes a new electroplating copper brightener, thiazoline-based sodium dithiopropane sulfonate (SH 110), which is used in the electroplating process of printed circuit boards in the same year to obtain a plating layer with good surface brightness and certain leveling capability. Subsequently, liyabing, wangcheng and the like discuss the action mechanism of an SPS-PEG-Jiannagreen (JGB) additive system in the hole-sealing copper plating process and the actual effect mechanism of the additive, and the leveling effect of the JGB is considered to come from the adsorption characteristic of the JGB on the surface of a cathode, and the JGB has the leveling effect because the adsorption strength is increased along with the negative shift of the potential. In the beginning of the 21 st century, dow et al conducted more detailed studies on the filling of through-holes and blind-holes, and explained the mode of action of leveling agents during electroplating through studies on several different leveling agents, which are believed to have a synergistic effect with accelerators and inhibitors. The effect of the pulse plating additive and the chloride ion on the copper electrode process is studied by Chen Wen et al, and the chloride ion is considered to play a very important role in the process of the copper plating additive. The aged spring and the like comparatively research the influence of a plurality of plating solution circulation modes and increased oscillation on the mass transfer of the solution in the hole in the PCB electroplating process, and carry out experimental verification and theoretical analysis. The method is considered to effectively improve the uniform plating capability of the deep hole copper plating of the PCB with the high thickness-diameter ratio by adopting measures such as bottom spraying, fixture oscillation increasing and the like.
Copper electrodeposition is widely used in Printed Circuit Boards (PCBs), integrated Circuit (IC) packages, and sophisticated microprocessors. This is because copper has good electrical conductivity, thermal conductivity and corrosion resistance, and acidic copper plating is the most important method in copper electrodeposition. The process has the following characteristics: the components of the electroplating solution are simple copper sulfate and sulfuric acid; the electroplating solution has high current efficiency and high deposition speed; the whitening effect of the whitening agent is obvious, and the mirror surface gloss coating can be obtained. In order to obtain coatings with good appearance, acceptable leveling properties and excellent physical properties, various organic additives must be added to the electroplating solution including suppressors, brightening and leveling agents. Meanwhile, many studies on the leveler have focused on Janus Green B (JGB). The addition of a leveler makes it easier to control the effective concentration of the entire additive system. Thus, many scholars believe that levelers play a very critical, and sometimes even decisive, role throughout the via plating additive system. Development of different types of levelers has become a focus of research. From some reports to date, it has been found that leveling agents are usually quaternary ammonium compounds or nitrogen-containing heterocyclic compounds, typically dye-based materials. The leveling agent is a high-strength inhibitor, and can achieve the leveling purpose under the matching use of other additives.
Among a plurality of dyes and pigment substances, the dye is mainly used for dyeing cotton fibers and printing cotton cloth, and is also used for two-bath over-dyeing of vinylon and polyester-cotton fabrics. The dyed viscose fiber has light color, can be combined with vat blue, brown, olive and the like to form blue, dark grey and the like, is also used for manufacturing pigments for ink, is used for dyeing cotton fiber, can be used for directly printing cotton cloth, can be processed into pigments, and can be used for preparing red-light blue paint instead of phthalocyanine blue and permanent violet RL. In recent years, indanthrone (pigment blue 60) has been studied less and is mainly used in dyes.
Disclosure of Invention
The first purpose of the invention is to provide an indanthrone (pigment blue 60) quaternary ammonium salt compound.
The second purpose of the invention is to provide a preparation method of the indanthrone (pigment blue 60) quaternary ammonium salt compound.
The third purpose of the invention is to provide the application of the indanthrone (pigment blue 60) quaternary ammonium salt compound as a plating additive.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
in a first aspect, the present invention provides an indanthrone (pigment blue 60) quaternary ammonium salt compound, which has a structural formula shown in formula B:
wherein:
R 1 is composed of
-Cl、-Br、-F、-I、-CN、- t Bu、-CH 3 、-C 2 H 5 、-C 6 H 11 、-H、-CH 2 Cl、-OCH 3 、-NH 2 、-CH 2 NH 2 、-NHCH 3 、-N(CH 3 ) 2 、-NO 2 、-OH、-SH、-HSO 3 ；
R 2 Is composed of
n is an integer of 1 to 18;
y is Br, F, cl, I, HSO 3 、HSO 4 、HCO 3 、CF 3 CO 3 、H 2 PO 4 OTf, OTs or BF 4 。
Preferred compounds of the invention are: the structural formula of the indanthrone (pigment blue 60) quaternary ammonium salt compound is shown as the general formula B:
R 2 is composed of
n is an integer of 1 to 18;
y is Br, F, cl, I, HSO 3 、HSO 4 、HCO 3 、CF 3 CO 3 、H 2 PO 4 OTf, OTs or BF 4 。
More preferred compounds of the invention are: in formula B:
R 2 is composed of
n is 2, 3, 4, 5 or 6;
y is Cl, br, F, I.
Preferred compounds of the invention are: in the general formula B, the compound represented by the formula,
R 2 is composed of
n is 4;
y is Cl, br, F, I.
The most preferred compounds of the invention are:
the second aspect of the present invention provides a preparation method of the indanthrone (pigment blue 60) quaternary ammonium salt compound, which comprises the following steps:
mixing indanthrone (pigment blue 60), bromoalkane and alkali with the molar ratio of 1 (2-10) to (2-10) with a proper solvent, heating, stirring, refluxing and reacting for 1-24 h, performing suction filtration, removing the solvent from filtrate to obtain a crude product, and performing column chromatography to obtain a compound A;
mixing the compound A, trimethylamine hydrochloride and sodium bicarbonate with the molar ratio of 1 (2-10) to (2-10) with a proper solvent, heating, stirring, refluxing and reacting for 1-24 h, cooling, filtering, removing the solvent from the filtrate, and performing column chromatography to obtain the indanthrone quaternary ammonium salt compound, namely the compound shown in the formula B.
The bromoalkane is one of the following structures:
The base is sodium hydride.
The solvent is tetrahydrofuran and acetonitrile.
The molar ratio of indanthrone (pigment blue 60), bromoalkane and base is 1.
The molar ratio of the compound A to the trimethylamine hydrochloride is 1.
The third aspect of the invention provides the application of the indanthrone (pigment blue 60) quaternary ammonium salt compound as an electroplating additive.
The electroplating additive is an electroplating leveling agent.
The electroplating is acid copper electroplating.
Due to the adoption of the technical scheme, the invention has the following advantages and beneficial effects:
the indanthrone (pigment blue 60) quaternary ammonium salt compound has good electroplating performance, and the quaternary ammonium salt structure can have larger coverage area on the surface of an electrode through nitrogen positive ions in the structure, namely a quaternization center, can increase cathode polarization, inhibit copper deposition, enable electroplating particles to be finer, enable a copper-plated layer to obtain high preferred crystal plane orientation, and enable the copper-plated layer to be used as a quaternary ammonium salt leveling agent for acid copper electroplating.
The indanthrone (pigment blue 60) quaternary ammonium salt compound has good electroplating performance and can generate synergistic inhibition effect with other electroplating additives, and the electroplating performance is verified by a cyclic voltammetry curve, a polarization curve and a constant current meter time-addition curve.
The indanthrone (pigment blue 60) quaternary ammonium salt compound has a simple preparation method, can be used as an electroplating additive to be applied to electroplating, and obtains a good effect through a series of tests.
Drawings
FIG. 1 is a graph showing the polarization curves of electrolytes containing different concentrations of compound B-1 at a scan rate of 2mVs -1 。
FIG. 2 shows a 2. Mu. Mol/l time-bond-NaGreen B (commercial product, hereinafter referred to as JGB) and a compound B-1 polarization curve, with a scanning speed of 2mVs -1 。
FIG. 3 is a plot of cyclic voltammograms of the effect of varying concentrations of compound B-1 on copper deposition.
FIG. 4 is a graph comparing cyclic voltammograms of Compound B-1 and JGB, all at a concentration of 2. Mu. Mol/l.
FIG. 5 shows the current density at 2A/dm for different rotation speeds 2 A constant current chronograph addition curve of compound B-1 was followed.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The reagents used in the examples of the invention were as follows: indanthrone (pigment blue 60) (manufacturer: jiuding chemical, specification: 5g, purity: analytically pure), 1, 6-dibromohexane (manufacturer: shanghai Aladdin Biochemical technology Co., ltd., specification: 1kg, purity: 97.0%), trimethylamine hydrochloride (manufacturer: shanghai Mecang Biochemical technology Co., ltd., specification: 1000g, purity: 99%), sodium bicarbonate (manufacturer: shanghai Mecang Biochemical technology Co., ltd., specification: 500g, purity: 99%), tetrahydrofuran (manufacturer: bailingwei Technology Co., ltd., specification: 500mL, purity: 99%), acetonitrile (manufacturer: bailingwei Techno Co., specification: 2.5L, purity: 99%), and sodium hydride (manufacturer: shanghai Aladdin Biochemical technology Co., ltd., specification: 250g, purity: 60%).
The reagents used in the examples of the invention were as follows: cuSO 4 ·5H 2 O (manufacturer: bailingwei science and technology Co., ltd., specification: 500g, purity: 98%), concentrated sulfuric acid (manufacturer: national drug group chemical reagent Co., ltd., specification: 500mL, purity: 98.08%), hydrochloric acid (manufacturer: changtui City pond Fine chemical industry Co., ltd., specification: 500mL, content: 36% -38%). Potentiostats (manufacturer: wantong China, switzerland, model: multi Autolab M204), platinum rotating disk electrodes (manufacturer: jiangsu Jiangxi electric analytical instruments, inc., model: ATA-1B), ag/AgCl electrodes (manufacturer: tianjin Adama Heng Cheng scientific and technological development)Limit company, model: RE-1D), platinum wire electrode (manufacturer: tianjin Ida Heng Cheng science and technology development Limited, model: pt 017).
Example 1
Indanthrone (pigment blue 60) (4.42g, 10mmol), 1, 6-dibromohexane (12.20g, 50mmol), sodium hydride (1.20g, 50mmol) and 50mL of tetrahydrofuran as a solvent were put together in a 150mL pressure bottle to be mixed, heated, stirred, refluxed and reacted for 24 hours, a solid was removed by suction filtration using a suction flask, and the obtained filtrate was subjected to rotary evaporation to remove the solvent to obtain a crude product and subjected to column chromatography on a silica gel column with dichloromethane: petroleum ether =1 as a developing agent to obtain 1.53g of a solid compound a-1 in a yield of 20%.
The compound a-1 (1.5g, 2mmol), trimethylamine hydrochloride (0.95g, 10mmol), sodium bicarbonate (0.84g, 15mmol) and 30mL acetonitrile solvent were mixed together in a 120mL reaction flask, heated, stirred, refluxed and reacted for 12 hours, the reaction solution was cooled, then the solid was removed by suction filtration, the filtrate was subjected to rotary evaporation to remove acetonitrile, column chromatography on a neutral alumina column, and purification was performed with dichloromethane: methanol =50 as a developing agent to obtain 0.72g of a product, a red solid compound B-1, in a yield of 50%.
1 H NMR(400MHz,MeOD)δ8.61-8.54(m,2H),8.40(d,J＝8Hz,2H),8.39-8.31(m,2H),7.88(d,J＝8Hz,2H),7.77-7.73(m,4H),4.20(t,J＝4Hz,4H),3.31(t,J＝4Hz,4H),3.21(s,18H),2.26-2.28(m,4H),2.09-2.12(m,4H),1.79-1.81(m,4H),1.57-1.77(m,4H)。 13 C NMR(100MHz,MeOD)δ152.7,149.6,143.4,142.9,130.3,129.3,128.8,125.8,121.0,67.8,53.7,31.5,31.3,30.5,27.6,27.5,27.2,27.1,24.1,24.1,23.9.MS(ESI)m/z:1/2[M-2Cl] + calcd for C 23 H 27 N 2 O 2 363.2067；found,363.2070.
The anion was identified as a chloride ion by showing a white precipitate using a silver nitrate aqueous solution.
Example 2
The effect of compound B-1 on the copper ion deposition current density was tested.
Preparing CuSO with 60g/L 4 ·5H 2 O、200g/L H 2 SO 4 In the case of a 50mg/L copper sulfate solution containing chloride ions, a Pt rotary electrode as a working electrode, a platinum rod as a counter electrode and Ag/AgCl as a reference electrode, at a rotation speed of 2000 revolutions, solutions of the compound B-1 prepared in example 1 were added to the above copper sulfate solution containing chloride ions at different concentrations (the concentrations were 0, 2, 4, 6, 8, 10. Mu. Mol/L, respectively, and the compound B-1 was dissolved in deionized water) to perform a cathodic polarization curve test. As shown in FIG. 1, FIG. 1 is a polarization curve of an electrolyte containing different concentrations of compound B-1, and the scanning speed is 2mVs -1 . The inhibiting effect of compound B-1 prepared according to example 1 on the copper ion deposition on the surface of copper material at different concentrations and the polarization curve of the blank control, with the electrode (Ag/AgCl) potential (unit: volts) on the abscissa and the current density (unit: ampere/square decimeter) on the ordinate. As can be seen from FIG. 1, the compound B-1 can increase the cathodic polarization, and when the potential was shifted from positive to negative over 0V without the compound B-1 prepared in example 1 in the solution, a deposition current of copper was observed, and when the compound B-1 prepared in example 1 was added to the solution, the deposition potential of copper was shifted negatively, and when the potential reached-0.17V when the compound B-1 prepared in example 1 in the solution reached 4. Mu. Mol/l, a deposition current of copper was observed. It can be concluded that compound B-1 can inhibit the deposition of copper ions.
In addition, when JGB was compared with the polarization curve of compound B-1 at a concentration of 2. Mu. Mol/l, as shown in FIG. 2, the scan speed was 2mVs as compared with the polarization curve of compound B-1 for Kelvin B (commercial product, hereinafter referred to as JGB) at 2. Mu. Mol/l in FIG. 2 -1 As can be seen from FIG. 2, compound B-1 has a significantly more pronounced effect than JGB.
"Janus green" (a compound represented by formula H, abbreviated as "JGB") has the following structure:
example 3
The compound B-1 was tested for its ability to inhibit the deposition of copper ions.
Preparing a solution containing 60g/L CuSO 4 ·5H 2 O、200g/L H 2 SO 4 In the case of a 50mg/L copper sulfate solution containing chloride ions, a Pt rotary electrode as a working electrode, a platinum rod as a counter electrode and Ag/AgCl as a reference bus, at a rotation speed of 2000 rpm, solutions of the compound B-1 prepared in example 1 were added to the above copper sulfate solution containing chloride ions at different concentrations (the concentrations were 0, 2, 4, 6, 8, and 10. Mu. Mol/L, respectively, and the compound B-1 was dissolved in deionized water), and a cyclic voltammetry curve test was performed. As shown in FIG. 3, FIG. 3 is a cyclic voltammogram showing the effect of different concentrations of compound B-1 on copper deposition, and the effect of compound B-1 prepared according to example 1 on the inhibition of copper ion deposition on the surface of a copper material at different concentrations is shown as a cyclic voltammogram of a blank control, wherein the abscissa is the electrode (Ag/AgCl) potential (unit: volt) and the ordinate is the current density (unit: ampere/dm) 2 ). The results show that the compound B-1 can be adsorbed on the surface of the cathode, and a barrier layer is formed on the surface of the cathode to obstruct the deposition of copper, so that the resistance of copper deposition reaction is increased, and the inhibiting effect is enhanced along with the increase of the concentration of the compound B-1.
In addition, when the cyclic voltammograms of the compound B-1 and JGB at a concentration of 2. Mu. Mol/l are compared, as shown in FIG. 4, and FIG. 4 is a comparison graph of the cyclic voltammograms of the compound B-1 and JGB at 2. Mu. Mol/l, the compound B-1 is found to have a significantly better effect than JGB.
Example 4
Compound B-1 was tested as a leveler with PEG and SPS for synergistic inhibitory performance.
Preparing CuSO with 60g/L 4 ·5H 2 O、200g/L H 2 SO 4 50mg/L of a copper sulfate solution of chloride ions, a Pt rotary electrode as a working electrode, a platinum rod as a counter electrode and Ag/AgCl as a reference electrode, respectively at a rotation speed of 100 revolutions per minute and 1000 revolutions per minute every 1000 secondsTo the solution were added 200ppm of polyethylene glycol PEG (average molecular weight: 10000), 1ppm of sodium polydithio-dipropyl sulfonate (SPS) and 2ppm of the solution of the compound B-1 prepared in example 1 (Compound B-1 dissolved in deionized water) to obtain a constant current time addition curve, as shown in FIG. 5, where FIG. 5 is a graph showing current density of 2A/dm at different rotation speeds 2 A constant current chronograph addition curve of compound B-1 was followed. The compound B-1 prepared according to example 1 was tested by timed addition at different rotational speeds, with time (unit: s) on the abscissa and potential (unit: volts) on the ordinate. As can be seen from FIG. 5, the depolarization phenomenon caused by SPS was suppressed and the potential was shifted negatively by the addition of compound B-1, indicating that compound B-1 still inhibited the deposition of copper in the presence of SPS and PEG. The 1000rpm and 100rpm rotation speeds were used to simulate deposition at the orifice and at the inner wall of the via, respectively. The potential difference at different rotation speeds is defined as Δ η = η (100 rpm) - η (1000 rpm), while Δ η 2 =14mV being positive and greater than Δ η 1 ＝4mV(Δη 2 And Δ η 1 Representing the potential difference at different rpm after addition of compound B-1 and SPS, respectively), indicating that the adsorption behavior of compound B-1 is a convection dependent adsorption, used to characterize the difference in the different inhibition at 1000rpm and 100 rpm. If Δ η is positive, it indicates that strong convection results in less copper deposition and is suitable for plating with vias. Therefore, the adsorption of compound B-1 at the hole opening of the PCB (the PCB is a printed circuit board having a through hole, used for actual copper plating) is stronger than that at the middle position of the hole, suppressing the deposition of copper at the hole opening. As can be seen from fig. 5, Δ η =14mV, i.e., the suppression effect of the rotating disk electrode at different rotation speeds is different, and the deposition potential difference is about 14mV.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (7)
1. An indanthrone quaternary ammonium salt compound, which is characterized in that the indanthrone quaternary ammonium salt compound has a structural formula shown as a general formula B:
R 2 is composed of
n is an integer of 1 to 18,
y is Br, F, cl, I, HSO 3 、HSO 4 、HCO 3 、CF 3 CO 3 、H 2 PO 4 OTf, OTs or BF 4 。
2. The indanthrone quaternary ammonium salt compound according to claim 1, wherein
R 2 Is composed of
n is 2, 3, 4, 5 or 6, Y is Cl, br, F, I.
3. The indanthrone quaternary ammonium salt compound according to claim 2, wherein,
R 2 is composed of
n is 4, Y is Cl, br, F, I.
4. The indanthrone quaternary ammonium salt compound according to claim 3, wherein the indanthrone quaternary ammonium salt compound has a structural formula:
5. a method for preparing the indanthrone quaternary ammonium salt compound according to any one of claims 1 to 4, comprising the steps of:
mixing indanthrone, bromoalkane, alkali and a solvent in a molar ratio of 1 (2-10) to (2-10), heating, stirring, refluxing for 1-24 hours, performing suction filtration, removing the solvent from filtrate to obtain a crude product, and performing column chromatography to obtain a compound A;
mixing the compound A, trimethylamine hydrochloride, sodium bicarbonate and a solvent in a molar ratio of 1 (2-10) to 2-10, heating, stirring, refluxing and reacting for 1-24 h, cooling, filtering, removing the solvent from the filtrate, and performing column chromatography to obtain the indanthrone quaternary ammonium salt compound;
wherein the alkyl bromide is
n is an integer of 1 to 18; x is F, cl, br or I; r 2 And Y has the same meaning as described in any one of 1 to 4; the base is sodium hydride; the solvent is tetrahydrofuran or acetonitrile.
6. The process according to claim 5, wherein the molar ratio of indanthrone, bromoalkane and base is 1; the molar ratio of compound a to trimethylamine hydrochloride is 1.
7. Use of the indanthrone quats of any one of claims 1 to 4 as an additive for electroplating;
wherein the electroplating additive is an electroplating leveling agent, and the electroplating is acid copper electroplating.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006232867A (en) * | 2005-02-22 | 2006-09-07 | Dainichiseika Color & Chem Mfg Co Ltd | Easily dispersible pigment composition and its use |
| CN109824674A (en) * | 2019-03-11 | 2019-05-31 | 华东理工大学 | Heterocycle pyrrolo-pyrrole-dione quaternary ammonium compound and preparation method thereof and purposes |
| CN110105357A (en) * | 2019-06-10 | 2019-08-09 | 华东理工大学 | A kind of quinacridone quaternary ammonium compound and preparation method thereof and purposes |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006232867A (en) * | 2005-02-22 | 2006-09-07 | Dainichiseika Color & Chem Mfg Co Ltd | Easily dispersible pigment composition and its use |
| CN109824674A (en) * | 2019-03-11 | 2019-05-31 | 华东理工大学 | Heterocycle pyrrolo-pyrrole-dione quaternary ammonium compound and preparation method thereof and purposes |
| CN110105357A (en) * | 2019-06-10 | 2019-08-09 | 华东理工大学 | A kind of quinacridone quaternary ammonium compound and preparation method thereof and purposes |
Non-Patent Citations (2)
| Title |
|---|
| Tunable Photoluminescence Including White-Light Emission Based on Noncovalent Interaction-Locked N,N′-Disubstituted Dihydrodibenzo[a,c]phenazines;Jie Wang et al.;《Adv. Optical Mater》;20180416;第6卷;第1-7页 * |
| 引发剂对UV 油墨固化速度影响的研究;张开瑞 等;《应用化学》;20120430;第41卷(第4期);第584-587、594页 * |
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