CN118325359B - C.i. pigment red 57 for readily dispersible inks: 1 and a process for the preparation thereof - Google Patents
C.i. pigment red 57 for readily dispersible inks: 1 and a process for the preparation thereof Download PDFInfo
- Publication number
- CN118325359B CN118325359B CN202410755951.3A CN202410755951A CN118325359B CN 118325359 B CN118325359 B CN 118325359B CN 202410755951 A CN202410755951 A CN 202410755951A CN 118325359 B CN118325359 B CN 118325359B
- Authority
- CN
- China
- Prior art keywords
- silicon dioxide
- nano silicon
- pigment red
- stirring
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 235000010187 litholrubine BK Nutrition 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000000976 ink Substances 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 116
- 239000005543 nano-size silicon particle Substances 0.000 claims abstract description 63
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000003756 stirring Methods 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000000243 solution Substances 0.000 claims description 25
- 239000011259 mixed solution Substances 0.000 claims description 22
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000012954 diazonium Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 18
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical class C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 16
- 239000012065 filter cake Substances 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- -1 silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative Chemical class 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 10
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 claims description 10
- RTIUWXJUJKDMPG-UHFFFAOYSA-N 7-formyl-3-hydroxynaphthalene-2-carboxylic acid Chemical compound O=CC1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 RTIUWXJUJKDMPG-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 10
- 239000001110 calcium chloride Substances 0.000 claims description 10
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 claims description 8
- 238000006193 diazotization reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000002791 soaking Methods 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000000967 suction filtration Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000049 pigment Substances 0.000 abstract description 29
- 239000006185 dispersion Substances 0.000 abstract description 20
- 239000002245 particle Substances 0.000 abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 abstract description 5
- 230000002776 aggregation Effects 0.000 abstract description 4
- 239000002105 nanoparticle Substances 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 3
- 238000001556 precipitation Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000003993 interaction Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- GLLRIXZGBQOFLM-UHFFFAOYSA-N Xanthorin Natural products C1=C(C)C=C2C(=O)C3=C(O)C(OC)=CC(O)=C3C(=O)C2=C1O GLLRIXZGBQOFLM-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
- C09B29/106—Hydroxy carboxylic acids of the naphthalene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0091—Process features in the making of dispersions, e.g. ultrasonics
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention discloses a C.I. pigment red 57 for easily dispersible ink, which comprises: 1 and a preparation method thereof, which belong to the technical field of pigment synthesis, wherein a layer of hydrophobic long carbon chain is modified on the surface of nano silicon dioxide, and then pigment is grafted; firstly, the hydrophobic long carbon chain can prevent mutual aggregation or precipitation among nano silicon dioxide particles due to strong repulsive interaction in water, so that the stability of the nano particles is improved, and the nano particles are easier to disperse uniformly; secondly, the nano silicon dioxide improves the dispersibility of the pigment in a medium and improves the transparency of the pigment; the C.I. pigment red 57 for the printing ink with good dispersibility is prepared by the invention: 1, c.i. pigment red 57 prepared according to the invention: 1 has strong tinting strength, high transparency and good stability in a dispersion system, and the preparation method is simple and has great application value.
Description
Technical Field
The invention belongs to the technical field of pigment synthesis, and particularly relates to C.I. pigment red 57 for easily-dispersible ink, which comprises the following components: 1 and a preparation method thereof.
Background
C.i. pigment red 57:1 is red organic pigment prepared by diazotizing 4-aminotoluene-3-sulfonic acid, coupling with 2-hydroxy-3-naphthalene, and finally adding alkaline earth metal salt for laking. The pigment has bright color, strong tinting strength, acid and alkali resistance and good permeation resistance, and is widely used for tinting rubber, plastics, printing ink, paint and daily chemicals.
C.i. pigment red 57:1 the organic pigment is insoluble in water and is dispersed in a coloring medium as fine particles, so that the organic pigment is dispersed in water by ultrasonic or ball milling, the pigment dispersion liquid is stable, and pigment particles are aggregated and deposited after standing for a period of time, thereby influencing the tinting strength and color fastness of the pigment. In order to ensure good dispersibility of the pigment, a method commonly used at present is to add a surfactant to uniformly and stably disperse the pigment in a medium, but the surfactant is generally adsorbed or covered on the surface of pigment particles, so that the polarity of the surface of the organic pigment particles is adjusted, the polarity of the surface of the pigment particles is changed to ensure that the pigment achieves a good dispersing effect, and the surfactant has the defect that desorption easily occurs, so that the covering power of the pigment to a substrate material is influenced. Therefore, how to prepare a c.i. pigment red 57 for an easily dispersible ink by modifying the pigment itself so as to have a good dispersing effect: 1 has important significance.
Disclosure of Invention
To solve the above problems, an object of the present invention is to provide a c.i. pigment red 57 for an easily dispersible ink: 1 and a preparation method thereof.
The invention aims to achieve the aim, and the aim is achieved by the following technical scheme:
C.i. pigment red 57 for readily dispersible inks: 1, diazotizing 4-aminotoluene-3-sulfonic acid, coupling with 3-hydroxy-2-naphthoic acid derivatives modified by nano silicon dioxide, and finally adding calcium chloride aqueous solution for laking;
The 3-hydroxy-2-naphthoic acid derivative modified by nano silicon dioxide is prepared by the following method:
1) Soaking nano silicon dioxide in an organic solvent 1, stirring and dispersing uniformly, adding 7-aminoheptanoic acid into the mixture, stirring and mixing uniformly, adding 4-dimethylaminopyridine and 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 10-20 hours at 30-70 ℃, and after the reaction is finished, performing suction filtration, and washing an obtained filter cake with the organic solvent 2 for 2-3 times to obtain amino-terminated nano silicon dioxide;
2) Adding the amino-terminated nano silicon dioxide obtained in the step 1) and 7-formyl-3-hydroxy-2-naphthoic acid into an alcohol organic solvent, reacting for 5-8 hours at 25-30 ℃, then adding a reducing agent, continuing to react for 5-10 hours, distilling under reduced pressure to remove the solvent after the reaction is finished, adding water into the obtained residue, stirring, filtering, and drying the obtained filter cake to obtain the nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative.
The mass ratio of the nano silicon dioxide to the organic solvent 1, 7-aminoheptanoic acid to the 4-dimethylaminopyridine to the 1-ethyl- (3-dimethylaminopropyl) carbodiimide in the step 1) is 1: 30-50: 8-15: 3.5 to 6.5: 8.5-16.
The organic solvent 1 in the step 1) is tetrahydrofuran, dichloromethane, dimethylformamide or dimethyl sulfoxide.
The organic solvent 2 in the step 1) is tetrahydrofuran, acetone or ethyl acetate.
The mass ratio of the amino-terminated modified nano silicon dioxide to the 7-formyl-3-hydroxy-2-naphthoic acid in the step 2) to the alcohol organic solvent to the reducing agent to the water is 1: 10-15: 30-50: 8-17: 20-30.
The alcohol organic solvent in the step 2) is methanol, ethanol or isopropanol.
The reducing agent in the step 2) is sodium borohydride or sodium cyanoborohydride.
Preparation of the c.i. pigment red 57 for the easily dispersible ink: 1, comprising the steps of:
(1) Adding 5-8 parts by weight of 4-aminotoluene-3-sulfonic acid and 20-25 parts by weight of 30% hydrochloric acid solution into a diazonium reactor, uniformly mixing, adding 100 parts by weight of water, stirring and cooling to 0-5 ℃, adding 20-25 parts by weight of 30% sodium nitrite aqueous solution for diazotization reaction for 0.5-1 h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium liquid;
(2) Adding 100 parts of water and 3-5 parts of 3-hydroxy-2-naphthoic acid derivative modified by nano silicon dioxide into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into the diazonium solution obtained in the step (1) at 25-30 ℃, carrying out coupling reaction for 1-2 hours, adjusting the pH of a system to 8-9 by sodium carbonate in the reaction process, dropwise adding 20-30 parts of calcium chloride aqueous solution with the mass concentration of 30% into the solution after the reaction is finished, stirring and reacting for 2-3 hours after the completion of the dropwise adding, heating to 80-90 ℃, continuously stirring for 0.5-1 hour, filtering, washing and drying to obtain the C.I. pigment red 57 for the easily dispersible ink: 1.
Compared with the prior art, the invention has the following advantages:
The present invention is c.i. pigment red 57:1, modifying a layer of hydrophobic long carbon chain on the surface of nano silicon dioxide, and then grafting pigment; firstly, the hydrophobic long carbon chain can prevent mutual aggregation or precipitation among nano silicon dioxide particles due to strong repulsive interaction in water, so that the stability of the nano particles is improved, and the nano particles are easier to disperse uniformly; secondly, the nano silicon dioxide has larger specific surface area and stronger surface activity, so that the dispersibility of the pigment in a medium is improved, and on the other hand, the nano silicon dioxide has small particle size, can be uniformly dispersed in the medium, avoids sedimentation and agglomeration of pigment particles, and increases the stability of the pigment; meanwhile, the light scattering in the pigment can be reduced by the small size, and the transparency of the pigment is improved.
The easy-to-disperse ink prepared by the invention uses C.I. pigment red 57:1 contains hydroxyl and amino, can form hydrogen bond action with water, thus having better hydrophilicity and can be dispersed in water to form stable dispersion liquid.
The invention prepares the C.I. pigment red 57 with good dispersibility for printing ink by modifying the pigment: 1, c.i. pigment red 57 prepared according to the invention: 1 has strong tinting strength, high transparency and good stability in a dispersion system, and the preparation method is simple and has great application value.
Drawings
FIG. 1 is a C.I. pigment red 57 for a readily dispersible ink prepared in example 3 of the present invention: 1, a dispersion performance research diagram;
FIG. 2 is a C.I. pigment red 57 for a readily dispersible ink prepared in example 3 of the present invention: 1, a dispersion stability study chart.
Detailed Description
The foregoing is further elaborated by the following description of embodiments of the present invention, which are given by way of example only, and should not be construed as limiting the scope of the present invention. All techniques implemented based on the above description of the invention are within the scope of the invention.
Example 1 preparation of nanosilica modified 3-hydroxy-2-naphthoic acid derivatives:
Soaking 0.1kg of nano silicon dioxide in 3kg of tetrahydrofuran, stirring and dispersing uniformly, adding 0.8kg of 7-aminoheptanoic acid into the mixture, stirring and mixing uniformly, adding 0.35kg of 4-dimethylaminopyridine and 0.85kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting at 30 ℃ for 20 hours, and after the reaction is finished, performing suction filtration, washing the obtained filter cake with tetrahydrofuran for 2 times to obtain amino-terminated nano silicon dioxide;
Adding 0.1kg of amino-terminated nano silicon dioxide and 1kg of 7-formyl-3-hydroxy-2-naphthoic acid into 3kg of methanol, reacting for 8 hours at 25 ℃, adding 0.8kg of sodium borohydride, continuing to react for 5 hours, distilling under reduced pressure to remove the solvent after the reaction is finished, adding 2kg of water into the obtained residue, stirring, filtering, and drying the obtained filter cake to obtain the nano silicon dioxide-modified 3-hydroxy-2-naphthoic acid derivative.
Performing TGA test on nano silicon dioxide and 3-hydroxy-2-naphthoic acid derivatives modified by nano silicon dioxide, wherein the detection conditions are as follows: the temperature range is 30-600 ℃, the temperature rising speed is 10 ℃/min, and the weight loss detection result is shown in table 1. The results in table 1 show that the weight loss rate of the nano silicon dioxide is 2.54%, the nano silicon dioxide is mainly water adsorbed on the surface of the particles, and the weight loss rate of the 3-hydroxy-2-naphthoic acid derivative modified by the nano silicon dioxide reaches 28.3%, which shows that the surface of the nano silicon dioxide is successfully grafted with organic groups.
Weight loss results of nano silica materials prepared in Table 1
| Sample name | Nano silicon dioxide | 3-Hydroxy-2-naphthoic acid derivative modified by nano silicon dioxide |
| Weight loss ratio (%) | 2.54% | 28.3% |
C.i. pigment red 57 for easy dispersion ink: 1, preparation:
Adding 0.5kg of 4-aminotoluene-3-sulfonic acid and 2kg of hydrochloric acid solution with the mass concentration of 30% into a diazo reactor, uniformly mixing, adding 10kg of water, stirring and cooling to 0 ℃, adding 2kg of sodium nitrite aqueous solution with the mass concentration of 30% for diazotization reaction for 0.5h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium solution;
Adding 10kg of water and 0.3kg of nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into diazonium solution at 25 ℃, carrying out coupling reaction for 1h, adjusting the pH of a system to 8 by sodium carbonate in the reaction process, dropwise adding 2kg of 30% calcium chloride aqueous solution by mass concentration into the mixed solution after the reaction is finished, stirring and reacting for 2h after the dropwise addition is finished, heating to 80 ℃, continuously stirring for 0.5h, filtering, washing and drying to obtain the easily dispersible pigment C.I. pigment red 57 for printing ink: 1.
Example 2 preparation of nanosilica modified 3-hydroxy-2-naphthoic acid derivatives:
Soaking 0.1kg of nano silicon dioxide in 3.5kg of dichloromethane, stirring and dispersing uniformly, adding 1kg of 7-aminoheptanoic acid into the mixture, stirring and mixing uniformly, adding 0.42kg of 4-dimethylaminopyridine and 1kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting at 40 ℃ for 18 hours, filtering after the reaction is finished, washing the obtained filter cake with acetone for 2 times, and obtaining amino-terminated nano silicon dioxide;
Adding 0.1kg of amino-terminated modified nano silicon dioxide and 1.1kg of 7-formyl-3-hydroxy-2-naphthoic acid into 3.4kg of ethanol, reacting at 26 ℃ for 7.5 hours, adding 1kg of sodium cyanoborohydride, continuing to react for 6 hours, removing the solvent by reduced pressure distillation after the reaction is finished, adding 2.2kg of water into the obtained residue, stirring, carrying out suction filtration, and drying the obtained filter cake to obtain the nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative.
C.i. pigment red 57 for easy dispersion ink: 1, preparation:
Adding 0.55kg of 4-aminotoluene-3-sulfonic acid and 2.1kg of hydrochloric acid solution with the mass concentration of 30% into a diazo reactor, uniformly mixing, adding 10kg of water, stirring and cooling to 1 ℃, adding 2.1kg of sodium nitrite aqueous solution with the mass concentration of 30% for diazotization reaction for 0.6h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium solution;
Adding 10kg of water and 0.35kg of nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into diazonium solution at the temperature of 27 ℃, carrying out coupling reaction for 1.2 hours, regulating the pH value of a system to 8.5 by sodium carbonate in the reaction process, dropwise adding 2.2kg of 30% calcium chloride aqueous solution by mass concentration into the mixed solution after the reaction is finished, stirring and reacting for 2.2 hours after the dropwise addition is finished, heating to 84 ℃, continuously stirring for 0.65 hours, filtering, washing and drying to obtain the C.I. pigment red 57 for the easily dispersible ink: 1.
Example 3 preparation of nanosilica modified 3-hydroxy-2-naphthoic acid derivatives:
Soaking 0.1kg of nano silicon dioxide in 4.2kg of dichloromethane, stirring and dispersing uniformly, adding 1.2kg of 7-aminoheptanoic acid into the mixture, stirring and mixing uniformly, adding 0.5kg of 4-dimethylaminopyridine and 1.2kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 15h at 50 ℃, after the reaction is finished, performing suction filtration, and washing the obtained filter cake with ethyl acetate for 3 times to obtain amino-terminated nano silicon dioxide;
adding 0.1kg of amino-terminated nano silicon dioxide and 1.2kg of 7-formyl-3-hydroxy-2-naphthoic acid into 4kg of ethanol, reacting for 7 hours at 28 ℃, adding 1.2kg of sodium borohydride, continuing to react for 8 hours, distilling under reduced pressure to remove the solvent after the reaction is finished, adding 2.5kg of water into the obtained residue, stirring, filtering, and drying the obtained filter cake to obtain the nano silicon dioxide-modified 3-hydroxy-2-naphthoic acid derivative.
C.i. pigment red 57 for easy dispersion ink: 1, preparation:
Adding 0.65kg of 4-aminotoluene-3-sulfonic acid and 2.2kg of hydrochloric acid solution with the mass concentration of 30% into a diazo reactor, uniformly mixing, adding 10kg of water, stirring and cooling to 3 ℃, adding 2.3kg of sodium nitrite aqueous solution with the mass concentration of 30% for diazotization reaction for 0.75h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium solution;
Adding 10kg of water and 0.4kg of 3-hydroxy-2-naphthoic acid derivative modified by nano silicon dioxide into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into diazonium solution at 28 ℃, carrying out coupling reaction for 1.6 hours, regulating the pH of a system to 8.5 by sodium carbonate in the reaction process, dropwise adding 2.5kg of calcium chloride aqueous solution with the mass concentration of 30% into the mixed solution after the reaction is finished, stirring and reacting for 2.5 hours after the dropwise addition is finished, heating to 85 ℃, continuously stirring for 0.8 hours, filtering, washing and drying to obtain the C.I. pigment red 57 for the easily dispersible ink: 1.
Example 4 preparation of nanosilica modified 3-hydroxy-2-naphthoic acid derivatives:
Soaking 0.1kg of nano silicon dioxide in 4.8kg of dimethylformamide, stirring and dispersing uniformly, adding 1.4kg of 7-amino heptanoic acid into the mixture, stirring and mixing uniformly, adding 0.58kg of 4-dimethylaminopyridine and 1.5kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 12 hours at 60 ℃, filtering after the reaction is finished, washing the obtained filter cake with ethyl acetate for 3 times, and obtaining amino-terminated nano silicon dioxide;
Adding 0.1kg of amino-terminated modified nano silicon dioxide and 1.4kg of 7-formyl-3-hydroxy-2-naphthoic acid into 4.5kg of isopropanol, reacting at 29 ℃ for 6 hours, adding 1.5kg of sodium cyanoborohydride, continuing to react for 9 hours, removing the solvent by reduced pressure distillation after the reaction is finished, adding 2.8kg of water into the obtained residue, stirring, carrying out suction filtration, and drying the obtained filter cake to obtain the nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative.
C.i. pigment red 57 for easy dispersion ink: 1, preparation:
Adding 0.75kg of 4-aminotoluene-3-sulfonic acid and 2.4kg of hydrochloric acid solution with the mass concentration of 30% into a diazo reactor, uniformly mixing, adding 10kg of water, stirring and cooling to 4 ℃, adding 2.4kg of sodium nitrite aqueous solution with the mass concentration of 30% for diazotization reaction for 0.9h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium solution;
Adding 10kg of water and 0.46kg of nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into diazonium solution at 29 ℃, carrying out coupling reaction for 1.8 hours, regulating the pH of a system to 8.8 by sodium carbonate in the reaction process, dropwise adding 2.8kg of 30% calcium chloride aqueous solution by mass concentration into the mixed solution after the reaction is finished, stirring and reacting for 2.8 hours after the dropwise addition is finished, heating to 88 ℃, continuously stirring for 0.9 hours, filtering, washing and drying to obtain the C.I. pigment red 57 for the easily dispersible ink: 1.
Example 5 preparation of nanosilica modified 3-hydroxy-2-naphthoic acid derivatives:
soaking 0.1kg of nano silicon dioxide in 5kg of dimethyl sulfoxide, stirring and dispersing uniformly, adding 1.5kg of 7-amino heptanoic acid into the mixture, stirring and mixing uniformly, adding 0.65kg of 4-dimethylaminopyridine and 1.6kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 10 hours at 70 ℃, after the reaction is finished, performing suction filtration, and washing the obtained filter cake with acetone for 3 times to obtain amino-terminated nano silicon dioxide;
Adding 0.1kg of amino-terminated nano silicon dioxide and 1.5kg of 7-formyl-3-hydroxy-2-naphthoic acid into 5kg of methanol, reacting for 5 hours at 30 ℃, adding 1.7kg of sodium cyanoborohydride, continuing to react for 10 hours, removing the solvent by reduced pressure distillation after the reaction is finished, adding 3kg of water into the obtained residue, stirring, filtering, and drying the obtained filter cake to obtain the nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative.
C.i. pigment red 57 for easy dispersion ink: 1, preparation:
Adding 0.8kg of 4-aminotoluene-3-sulfonic acid and 2.5kg of hydrochloric acid solution with the mass concentration of 30% into a diazo reactor, uniformly mixing, adding 10kg of water, stirring to reduce the temperature to 5 ℃, adding 2.5kg of sodium nitrite aqueous solution with the mass concentration of 30% for diazotization reaction for 1h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium solution;
Adding 10kg of water and 0.5kg of nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into diazonium solution at 30 ℃, carrying out coupling reaction for 2 hours, adjusting the pH of a system to 9 by sodium carbonate in the reaction process, dropwise adding 3kg of 30% calcium chloride aqueous solution by mass concentration into the mixed solution after the reaction is finished, stirring and reacting for 3 hours after the dropwise adding is finished, heating to 90 ℃ and continuously stirring for 1 hour, filtering, washing and drying to obtain the C.I. pigment red 57 for the easily dispersible printing ink: 1.
Example 6 preparation of nanosilica modified 3-hydroxy-2-naphthoic acid derivatives:
Soaking 0.1kg of nano silicon dioxide in 4kg of tetrahydrofuran, stirring and dispersing uniformly, adding 1kg of 7-aminoheptanoic acid into the mixture, stirring and mixing uniformly, adding 0.35kg of 4-dimethylaminopyridine and 1.6kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting at 70 ℃ for 20 hours, and after the reaction is finished, performing suction filtration, washing the obtained filter cake with tetrahydrofuran for 2 times to obtain amino-terminated nano silicon dioxide;
Adding 0.1kg of amino-terminated nano silicon dioxide and 1.2kg of 7-formyl-3-hydroxy-2-naphthoic acid into 4kg of ethanol, reacting for 5 hours at 25 ℃, adding 0.8kg of sodium borohydride, continuing to react for 5 hours, distilling under reduced pressure to remove the solvent after the reaction is finished, adding 3kg of water into the obtained residue, stirring, filtering, and drying the obtained filter cake to obtain the nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative.
C.i. pigment red 57 for easy dispersion ink: 1, preparation:
Adding 0.8kg of 4-aminotoluene-3-sulfonic acid and 2kg of hydrochloric acid solution with the mass concentration of 30% into a diazo reactor, uniformly mixing, adding 10kg of water, stirring and cooling to 0 ℃, adding 2kg of sodium nitrite aqueous solution with the mass concentration of 30% for diazotization reaction for 1h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium solution;
Adding 10kg of water and 0.3kg of nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into diazonium solution at 30 ℃, carrying out coupling reaction for 1h, adjusting the pH of a system to 8.5 by sodium carbonate in the reaction process, dropwise adding 3kg of 30% calcium chloride aqueous solution by mass concentration into the mixed solution after the reaction is finished, stirring and reacting for 2h after the dropwise adding is finished, heating to 80 ℃, continuously stirring for 1h, filtering, washing and drying to obtain the easily dispersible pigment C.I. pigment red 57 for printing ink: 1.
The easily dispersible inks prepared in examples 1 to 6 were each prepared with c.i. pigment red 57:1, wherein the tinting strength is measured according to the method in GB 1708-79; the colored light is detected according to the method in GB 1864-80; fluidity was measured according to the method in GB 1719-79; bulk density was measured according to the method in GB/T21877-2015 by: accurately weighing 50g of pigment compound, placing into a measuring cylinder, sealing, oscillating up and down for 10 days, and recording the sample scale in the measuring cylinder; the transparency was measured in accordance with DIN 53163:1988 and the measurement results are shown in Table 2.
Table 2 Table of Performance parameters of the pigments prepared in examples 1 to 6
| Examples | Status of | Relative tinting strength (%) | Chromatic light | Fluidity (mm) | Bulk Density (ml/50 g) | Transparency of the film |
| 1 | Loose granular powder | 98 | Standard of | 45 | 24 | Preferably, it is |
| 2 | Loose granular powder | 100 | Standard of | 47 | 23 | Preferably, it is |
| 3 | Loose granular powder | 102 | Standard of | 48 | 22 | Preferably, it is |
| 4 | Loose granular powder | 101 | Standard of | 46 | 24 | Preferably, it is |
| 5 | Loose granular powder | 99 | Standard of | 44 | 25 | Preferably, it is |
| 6 | Loose granular powder | 100 | Standard of | 45 | 24 | Preferably, it is |
As can be seen from the results in table 1, the easily dispersible ink prepared according to the present invention uses c.i. pigment red 57:1, the bulk density is small, the dispersion is easy, the transparency is high, and the tinting strength is strong.
The easily dispersible ink prepared by the invention is prepared with c.i. pigment red 57:1, the dispersion performance is researched, and the research method is as follows: the easily dispersible ink prepared in example 3 was prepared with c.i. pigment red 57: 1.30 g of dispersant CT-1111, 1.2g of water and 100g of water are mixed to prepare the dispersion color paste. Stirring and grinding at 2500r/min, and during grinding, the dispersion was taken and the fineness change of the pigment at different grinding times was measured with a blade fineness gauge. The comparative example used commercially available c.i. pigment red 57:1. the detection results are shown in FIG. 1. As can be seen from the results of fig. 1, the easily dispersible ink prepared according to the present invention uses c.i. pigment red 57:1 as compared to commercially available c.i. pigment red 57:1, the fineness is smaller at about 40min, and the continuous grinding fineness is basically unchanged, which shows that the C.I. pigment red 57 for the easily dispersible ink prepared by the invention: 1 due to the modification of the nano-silica, it is easier to disperse in water, and due to the presence of hydroxyl and amino groups, it is easy to form hydrogen bonding with water, the time taken for dispersion is compared with the commercial c.i. pigment red 57:1 is shorter.
The readily dispersible inks prepared according to the present invention were tested for c.i. pigment red 57:1, the test method is as follows: the dispersion color paste prepared in the example 3 and the dispersion color paste prepared in the comparative example are respectively put into a centrifuge tube, centrifuged at 3000R/min, and 0.1g of centrifugate is taken every 10min to be diluted 1500 times for absorbance test, and specific absorbance (R) is calculated, wherein the specific absorbance calculation formula is: r=a (absorbance after centrifugation)/a 0 (absorbance before centrifugation). The detection results are shown in FIG. 2. As can be seen from the results of fig. 2, the easily dispersible ink prepared according to the present invention uses c.i. pigment red 57:1 is higher than the comparative example, which means that pigment particles of the comparative example are almost totally settled after centrifugation, whereas the pigment prepared according to the present invention has a smaller particle size due to the introduction of nano silica, and simultaneously has higher dispersion stability due to the strong repulsive effect of hydrophobic long carbon chains in water, thereby reducing the mutual aggregation or precipitation between nano silica pigment particles.
While the foregoing describes the embodiments of the present invention, it is not intended to limit the scope of the present invention, and various modifications or variations may be made by those skilled in the art without the need for inventive effort on the basis of the technical solutions of the present invention.
Claims (7)
1. C.i. pigment red 57 for readily dispersible inks: 1, characterized in that: diazotizing 4-aminotoluene-3-sulfonic acid, coupling with 3-hydroxy-2-naphthoic acid derivatives modified by nano silicon dioxide, and adding calcium chloride aqueous solution to carry out laking;
The 3-hydroxy-2-naphthoic acid derivative modified by nano silicon dioxide is prepared by the following method:
1) Soaking nano silicon dioxide in an organic solvent 1, stirring and dispersing uniformly, adding 7-aminoheptanoic acid into the mixture, stirring and mixing uniformly, adding 4-dimethylaminopyridine and 1-ethyl- (3-dimethylaminopropyl) carbodiimide, reacting for 10-20 hours at 30-70 ℃, and after the reaction is finished, performing suction filtration, and washing an obtained filter cake with the organic solvent 2 for 2-3 times to obtain amino-terminated nano silicon dioxide;
2) Adding the amino-terminated nano silicon dioxide obtained in the step 1) and 7-formyl-3-hydroxy-2-naphthoic acid into an alcohol organic solvent, reacting for 5-8 hours at 25-30 ℃, then adding a reducing agent, continuing to react for 5-10 hours, distilling under reduced pressure to remove the solvent after the reaction is finished, adding water into the obtained residue, stirring, filtering, and drying the obtained filter cake to obtain a nano silicon dioxide modified 3-hydroxy-2-naphthoic acid derivative;
the reducing agent in the step 2) is sodium borohydride or sodium cyanoborohydride.
2. The c.i. pigment red 57 for the easily dispersible ink according to claim 1:1, characterized in that: the mass ratio of the nano silicon dioxide to the organic solvent 1, 7-aminoheptanoic acid to the 4-dimethylaminopyridine to the 1-ethyl- (3-dimethylaminopropyl) carbodiimide in the step 1) is 1: 30-50: 8-15: 3.5 to 6.5: 8.5-16.
3. The c.i. pigment red 57 for the easily dispersible ink according to claim 1: 1, characterized in that: the organic solvent 1 in the step 1) is tetrahydrofuran, dichloromethane, dimethylformamide or dimethyl sulfoxide.
4. The c.i. pigment red 57 for the easily dispersible ink according to claim 1: 1, characterized in that: the organic solvent 2 in the step 1) is tetrahydrofuran, acetone or ethyl acetate.
5. The c.i. pigment red 57 for the easily dispersible ink according to claim 1:1, characterized in that: the mass ratio of the amino-terminated modified nano silicon dioxide to the 7-formyl-3-hydroxy-2-naphthoic acid in the step 2) to the alcohol organic solvent to the reducing agent to the water is 1: 10-15: 30-50: 8-17: 20-30.
6. The c.i. pigment red 57 for the easily dispersible ink according to claim 1: 1, characterized in that: the alcohol organic solvent in the step 2) is methanol, ethanol or isopropanol.
7. Preparation of c.i. pigment red 57 for the easily dispersible ink according to claim 1: 1, characterized in that: the method comprises the following steps:
(1) Adding 5-8 parts by weight of 4-aminotoluene-3-sulfonic acid and 20-25 parts by weight of 30% hydrochloric acid solution into a diazonium reactor, uniformly mixing, adding 100 parts by weight of water, stirring and cooling to 0-5 ℃, adding 20-25 parts by weight of 30% sodium nitrite aqueous solution for diazotization reaction for 0.5-1 h until Congo red test paper turns blue, and stopping the reaction to obtain diazonium liquid;
(2) Adding 100 parts of water and 3-5 parts of 3-hydroxy-2-naphthoic acid derivative modified by nano silicon dioxide into a coupling reactor, heating and stirring to obtain a mixed solution, adding the obtained mixed solution into the diazonium solution obtained in the step (1) at 25-30 ℃, carrying out coupling reaction for 1-2 hours, adjusting the pH of a system to 8-9 by sodium carbonate in the reaction process, dropwise adding 20-30 parts of calcium chloride aqueous solution with the mass concentration of 30% into the solution after the reaction is finished, stirring and reacting for 2-3 hours after the completion of the dropwise adding, heating to 80-90 ℃, continuously stirring for 0.5-1 hour, filtering, washing and drying to obtain the C.I. pigment red 57 for the easily dispersible ink: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410755951.3A CN118325359B (en) | 2024-06-13 | 2024-06-13 | C.i. pigment red 57 for readily dispersible inks: 1 and a process for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410755951.3A CN118325359B (en) | 2024-06-13 | 2024-06-13 | C.i. pigment red 57 for readily dispersible inks: 1 and a process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN118325359A CN118325359A (en) | 2024-07-12 |
| CN118325359B true CN118325359B (en) | 2024-09-03 |
Family
ID=91777402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410755951.3A Active CN118325359B (en) | 2024-06-13 | 2024-06-13 | C.i. pigment red 57 for readily dispersible inks: 1 and a process for the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118325359B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118530606B (en) * | 2024-07-29 | 2024-09-17 | 蓬莱新光颜料化工有限公司 | Based on c.i. pigment red 57:1 and a process for producing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117965053A (en) * | 2024-03-29 | 2024-05-03 | 蓬莱新光颜料化工有限公司 | C.i. pigment red 57 for aqueous ink: 1 and a process for the preparation thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2260081B1 (en) * | 2008-03-25 | 2014-11-26 | Xerox Corporation | Silica encapsulated organic nanopigments and method of making same |
| CN105524486A (en) * | 2015-12-15 | 2016-04-27 | 常熟市环虹化工颜料厂 | Preparation method of core-coated modified pigment red 170 |
| US20240124731A1 (en) * | 2022-09-26 | 2024-04-18 | Dupont Electronics, Inc. | Aqueous inkjet inks containing silanized silica particles |
-
2024
- 2024-06-13 CN CN202410755951.3A patent/CN118325359B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117965053A (en) * | 2024-03-29 | 2024-05-03 | 蓬莱新光颜料化工有限公司 | C.i. pigment red 57 for aqueous ink: 1 and a process for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN118325359A (en) | 2024-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN118325359B (en) | C.i. pigment red 57 for readily dispersible inks: 1 and a process for the preparation thereof | |
| CN108034305B (en) | Ferric oxide pigment color paste and preparation method thereof | |
| CN103709833A (en) | Polymer coated inorganic pigment paste for color modulation of production line and preparation method thereof | |
| CN119192897B (en) | Toluidine red pigment for building coating and preparation method thereof | |
| CN1429864A (en) | Pigment yellow 74 and printing ink composition | |
| CN117965053B (en) | C.i. pigment red 57 for aqueous ink: 1 and a process for the preparation thereof | |
| CN110589843A (en) | Preparation method of hydrophobic white carbon black with controllable particle size and core-shell structure | |
| CN116751463B (en) | Composite pigment coated with nano aluminum hydroxide and preparation method thereof | |
| CN116836567B (en) | Preparation method of dust-free pigment | |
| CA1104757A (en) | Mixtures of azo compounds, process for their preparation and their use | |
| CN112048189A (en) | System and method for preparing phthalocyanine blue P.B.15 by direct slurry acid swelling method | |
| JP4759966B2 (en) | Method for producing monoazo lake pigment composition | |
| CN109401435B (en) | Wear-resistant water-based ink and preparation process thereof | |
| CN110499041B (en) | The preparation method of easy-to-filter EVA wax-based composite spherical pigment yellow 14 | |
| WO2022142749A1 (en) | High-stability fluorescent color paste and preparation method therefor | |
| CN109679371B (en) | Preparation method of water-based food-grade pigment PR49:1 | |
| JP4802510B2 (en) | Disazo pigment composition and method for producing the same | |
| US2772984A (en) | Pigment | |
| US2174954A (en) | Azo pigment and method of preparing | |
| CN113462188B (en) | Pigment yellow 138 easy to disperse in weak solvent and preparation method thereof | |
| CN111909541A (en) | Preparation method of iron oxide yellow pigment with ultralow oil absorption | |
| CN116462989B (en) | A pigment coated with inorganic material inside and outside and its preparation method and application | |
| CN119708906B (en) | Toluidine red pigment for building coating and preparation method thereof | |
| CN109825105B (en) | Method for preparing nano-scale pigment red 146 by inverse miniemulsion method | |
| CN109181440A (en) | Environment-friendly water-based paint of one kind and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |