CN116970168B - Pigment orange 13-based organic pigment for ink and preparation method thereof - Google Patents
Pigment orange 13-based organic pigment for ink and preparation method thereof Download PDFInfo
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- CN116970168B CN116970168B CN202311230002.5A CN202311230002A CN116970168B CN 116970168 B CN116970168 B CN 116970168B CN 202311230002 A CN202311230002 A CN 202311230002A CN 116970168 B CN116970168 B CN 116970168B
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- 239000000049 pigment Substances 0.000 title claims abstract description 78
- FWTBRYBHCBCJEQ-UHFFFAOYSA-N 4-[(4-phenyldiazenylnaphthalen-1-yl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 FWTBRYBHCBCJEQ-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 239000012860 organic pigment Substances 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 238000003756 stirring Methods 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 238000001914 filtration Methods 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000001816 cooling Methods 0.000 claims description 24
- 239000000706 filtrate Substances 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 239000008367 deionised water Substances 0.000 claims description 16
- 229910021641 deionized water Inorganic materials 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 16
- 239000012065 filter cake Substances 0.000 claims description 16
- 239000011259 mixed solution Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- UVBFASMDGVKRAM-UHFFFAOYSA-N acetyl acetate 2-methylpyridine Chemical compound CC1=NC=CC=C1.C(C)(=O)OC(C)=O UVBFASMDGVKRAM-UHFFFAOYSA-N 0.000 claims description 10
- 235000010288 sodium nitrite Nutrition 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- -1 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one Chemical compound 0.000 claims description 8
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000012362 glacial acetic acid Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- YRQMBQUMJFVZLF-UHFFFAOYSA-N tert-butyl n-(4-hydroxyphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(O)C=C1 YRQMBQUMJFVZLF-UHFFFAOYSA-N 0.000 claims description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 4
- 239000004642 Polyimide Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 3
- 229920001721 polyimide Polymers 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012965 benzophenone Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 12
- 238000004042 decolorization Methods 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties
-
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
-
- 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
Abstract
The invention discloses an organic pigment for printing ink based on pigment orange 13 and a preparation method thereof, which belong to the technical field of pigment synthesis, wherein the pigment orange 13 is modified to prepare a three-dimensional cellular polyimide polymer with high molecular weight, so that the three-dimensional cellular polyimide polymer has excellent high temperature resistance, solvent resistance and chemical stability, and benzophenone is introduced into a main chain to increase the light resistance of the organic pigment.
Description
Technical Field
The invention belongs to the technical field of pigment synthesis, and particularly relates to an organic pigment for printing ink based on pigment orange 13 and a preparation method thereof.
Background
Organic pigments are an important class of pigments which have a rich color, vivid hue, and high light resistance, weather resistance, and chemical resistance, and are generally free of harmful substances, more environmentally friendly than conventional pigments, and thus are widely used in the fields of textile dyeing, paint, plastic coloring, cosmetics, printing ink, and the like.
The azo organic pigment is widely applied to ink, paint, rubber and the like in a manner of complete chromatography, bright color and reasonable price, but the azo pigment has various defects in heat resistance, light resistance, solvent resistance, migration resistance and the like due to the relatively small chemical structure, molecular weight and other factors, the traditional pigment orange 13 pigment is subjected to thermal decomposition when being used for polymer processing at the temperature of more than 200 ℃, and the decomposition products are azo compounds and aromatic amines, and dichloroaniline is generated when the temperature exceeds 240 ℃, so that the azo pigment has important influence on the health and environmental safety of people, and therefore, the development of the organic pigment for the ink with excellent high temperature resistance, light resistance, solvent resistance and the like has good development prospect.
Disclosure of Invention
In order to solve the problems, the invention aims to provide an organic pigment for ink based on pigment orange 13 and a preparation method thereof.
The invention aims to achieve the aim, and the aim is achieved by the following technical scheme:
an organic pigment for ink based on pigment orange 13, which has the structural formula:
a method for preparing the organic pigment for pigment orange 13-based ink, comprising the steps of: adding 1 part by weight of an amino-terminated pigment orange 13 derivative into 5-10 parts by weight of an aprotic polar solvent under the protection of nitrogen, stirring and dissolving, adding 0.7-1.5 parts by weight of 3, 4-benzophenone tetracarboxylic dianhydride into the solvent, reacting for 10-15 hours at 0-5 ℃, adding 4-6 parts by weight of an acetic anhydride-methylpyridine mixed solution into the obtained reaction solution after the reaction is finished, heating to 70-85 ℃, continuing to react for 24-36 hours, cooling to 25-30 ℃ after the reaction is finished, adding 10-15 parts by weight of absolute ethyl alcohol into the reaction solution, filtering, washing the obtained filter cake with deionized water for 3-5 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13;
the structural formula of the amino-terminated pigment orange 13 derivative is as follows:
the aprotic polar solvent is dimethylformamide, dimethylacetamide or N-methyl-2-pyrrolidone.
The volume ratio of acetic anhydride to picoline in the acetic anhydride-picoline mixed solution is 2-2.5: 1.
the amino-terminated pigment orange 13 derivative is prepared by the following method:
1) Adding 1 part by weight of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 2-3.5 parts by weight of 4- (boc-amino) phenol into 8-15 parts by weight of dimethyl sulfoxide, stirring and dissolving, then adding 1.5-2 parts by weight of alkali and 0.01-0.02 part by weight of cetyltrimethylammonium bromide, heating to 80-90 ℃, stirring and reacting for 18-30 hours, filtering after the reaction is finished, adding 5-10 parts by weight of water into the obtained filtrate, stirring and mixing uniformly, extracting 2-3 times by using 5-10 parts by weight of dichloromethane, merging organic phases, and distilling under reduced pressure to remove a solvent to obtain a solid;
2) Adding 1 part by weight of 3,3' -dichlorobenzidine, 2.5-4 parts by weight of sodium nitrite aqueous solution, 2.5-3 parts by weight of concentrated hydrochloric acid and 5-10 parts by weight of water into a reactor, reacting for 5-8 hours at 0-5 ℃, adding active carbon for decoloring after the reaction is completed, and filtering to obtain filtrate; adding 5-6.2 parts of the solid obtained in the step 1) and 0.4-0.6 part of sodium hydroxide into 10-15 parts of water, uniformly stirring and mixing, cooling to 10-15 ℃, and then adding glacial acetic acid to adjust the pH of a reaction system to 6.5-7 to obtain coupling liquid; adding the obtained coupling solution into the obtained filtrate, stirring and reacting for 2-3 hours, heating to 80-90 ℃ and continuing to react for 1-2 hours, keeping the pH of the system in the reaction process to be 6-6.5, cooling to 25-30 ℃ after the reaction is completed, filtering, washing the obtained filter cake with deionized water for 3-5 times, drying, adding the dried product into 0.5-0.8 part of trifluoroacetic acid and 10-20 parts of dichloromethane, reacting for 12-15 hours at 25-30 ℃, and distilling under reduced pressure to remove the solvent after the reaction is completed to obtain the amino-terminated pigment orange 13 derivative.
The alkali in the step 1) is potassium carbonate or sodium carbonate.
And in the step 2), the mass concentration of the concentrated hydrochloric acid is 35-38%.
And 2) the mass concentration of the sodium nitrite aqueous solution is 30-35%.
Compared with the prior art, the invention has the following advantages:
the organic pigment for pigment orange 13-based ink is synthesized by using 3, 4-benzophenone tetracarboxylic dianhydride and pigment orange 13 derivatives to obtain the cellular three-dimensional polymer, so that the molecular weight of the original pigment orange 13 is increased, in addition, a phthalimide structure and a rigid benzene ring structure are introduced into a main chain of the polymer, and the polyimide structure has excellent heat resistance and chemical resistance, so that the high temperature resistance and solvent resistance of the organic pigment are improved, and meanwhile, the three-dimensional cellular structure increases the chemical stability of the organic pigment.
The organic pigment for the pigment orange 13-based ink, which is synthesized by the invention, contains the benzophenone group, so that the light resistance of the organic pigment is improved.
The synthesis method disclosed by the invention is simple in synthesis steps, and the prepared organic pigment for the pigment orange 13-based ink is excellent in high temperature resistance, solvent resistance and light resistance, prolongs the service life of the pigment, and has a good development prospect.
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.
The structural formulas of the amino terminated pigment orange 13 derivatives in the following examples are:
；
the structural formulas of the organic pigments for the ink based on pigment orange 13 are as follows:
example 1 preparation of end amino pigment orange 13 derivative:
adding 0.1kg of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 0.2kg of 4- (boc-amino) phenol into 0.8kg of dimethyl sulfoxide, stirring and dissolving, adding 0.15kg of potassium carbonate and 0.001kg of cetyltrimethylammonium bromide, heating to 80 ℃, stirring and reacting for 18 hours, filtering after the reaction is finished, adding 0.5kg of water into the obtained filtrate, stirring and mixing uniformly, extracting for 2 times with 0.5kg of dichloromethane, merging organic phases, and distilling under reduced pressure to remove the solvent to obtain a solid; 1 H NMR (400 MHz, DMSO-d 6 , 298 K) δ 9.95 (s, 2H), 7.45 (d, 4H), 7.08 (d, 4H), 6.89 (s, 2H), 6.45 (s, 1H), 3.22 (s, 2H), 2.03 (s, 3H), 1.55 (s, 18H)。
0.1kg of 3,3' -dichlorobenzidine, 0.25kg of 30% by mass aqueous sodium nitrite solution, 0.25kg of 35% by mass concentrated hydrochloric acid and 0Adding 5kg of water into a reactor, reacting for 5 hours at 0 ℃, adding active carbon for decoloring after the reaction is finished, and filtering to obtain filtrate; adding 0.5kg of the obtained solid and 0.04kg of sodium hydroxide into 1kg of water, stirring and mixing uniformly, cooling to 10 ℃, adding glacial acetic acid to regulate the pH of a reaction system to 6.5, obtaining coupling liquid, adding the obtained coupling liquid into the obtained filtrate, stirring and reacting for 2 hours, heating to 80 ℃ to continue the reaction for 1 hour, keeping the pH of the system in the reaction process to be 6, cooling to 25 ℃ after the reaction is finished, filtering, washing the obtained filter cake with deionized water for 3 times, drying, adding the dried product into 0.05kg of trifluoroacetic acid and 1kg of dichloromethane, reacting at 25 ℃ for 12 hours, and distilling under reduced pressure to remove the solvent after the reaction is finished, thus obtaining the amino-terminated pigment orange 13 derivative. 1 H NMR (400 MHz, DMSO-d 6 , 298 K) δ 8.02 (s, 2H), 7.32-7.51 (m, 4H), 6.98 (s, 4H), 6.69-6.81 (m, 16H), 6.50 (s, 2H), 5.55 (s, 8H), 2.55 (s, 2H), 1.58 (s, 6H)。
Preparation of organic pigment for pigment orange 13-based ink:
under the protection of nitrogen, adding 0.1kg of end amino pigment orange 13 derivative into 0.5kg of dimethylformamide, stirring and dissolving, adding 0.07kg of 3, 4-benzophenone tetracarboxylic dianhydride into the mixture, reacting for 10 hours at 0 ℃, and adding 0.4kg of the mixture into the obtained reaction solution according to a volume ratio of 2:1, heating the acetic anhydride-picoline mixed solution to 70 ℃, continuing to react for 24 hours, cooling to 25 ℃ after the reaction is finished, adding 1kg of absolute ethyl alcohol into the mixed solution, filtering, washing the obtained filter cake with deionized water for 3 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13.
Example 2 preparation of end amino pigment orange 13 derivative:
adding 0.5kg of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 1.2kg of 4- (boc-amino) phenol into 4.5kg of dimethyl sulfoxide, stirring to dissolve, adding 0.8kg of potassium carbonate and 0.006kg of cetyltrimethylammonium bromide, heating to 82 ℃, stirring to react for 20 hours, filtering after the reaction is finished, adding 3kg of water into the obtained filtrate, stirring and mixing uniformly, extracting for 2 times by using 3kg of dichloromethane, merging organic phases, and distilling under reduced pressure to remove the solvent to obtain a solid;
adding 0.5kg of 3,3' -dichlorobenzidine, 1.5kg of 31% sodium nitrite aqueous solution, 1.3kg of 36% concentrated hydrochloric acid and 3kg of water into a reactor, reacting for 5.5h at 1 ℃, adding active carbon for decoloring after the reaction is completed, and filtering to obtain filtrate; adding 2.6kg of the obtained solid and 0.22kg of sodium hydroxide into 5.5kg of water, stirring and mixing uniformly, cooling to 12 ℃, adding glacial acetic acid to regulate the pH of a reaction system to 6.7, obtaining coupling solution, adding the obtained coupling solution into the obtained filtrate, stirring and reacting for 2.5 hours, heating to 82 ℃ and continuing to react for 1.2 hours, keeping the pH of the system in the reaction process to be 6.1, cooling to 26 ℃ after the reaction is finished, filtering, washing the obtained filter cake with deionized water for 4 times, drying, adding the dried product into 0.28kg of trifluoroacetic acid and 6kg of dichloromethane, reacting for 13 hours at 26 ℃, and distilling under reduced pressure to remove the solvent after the reaction is finished, thus obtaining the amino-terminated pigment orange 13 derivative.
Preparation of organic pigment for pigment orange 13-based ink:
under the protection of nitrogen, 0.1kg of end amino pigment orange 13 derivative is added into 0.6kg of dimethylacetamide, after stirring and dissolution, 0.08kg of 3, 4-benzophenone tetracarboxylic dianhydride is added into the mixture to react for 11 hours at 2 ℃, and after the reaction is finished, 0.45kg of the reaction liquid with the volume ratio of 2.1 is added into the reaction liquid: 1, heating the acetic anhydride-picoline mixed solution to 75 ℃, continuing to react for 28 hours, cooling to 25 ℃ after the reaction is finished, adding 1.2kg of absolute ethyl alcohol into the mixed solution, filtering, washing the obtained filter cake with deionized water for 4 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13.
Example 3 preparation of end amino pigment orange 13 derivative:
adding 0.1kg of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 0.3kg of 4- (boc-amino) phenol into 1kg of dimethyl sulfoxide, stirring and dissolving, then adding 0.18kg of sodium carbonate and 0.0015kg of cetyltrimethylammonium bromide, heating to 85 ℃, stirring and reacting for 24 hours, filtering after the reaction is finished, adding 0.75kg of water into the obtained filtrate, stirring and mixing uniformly, extracting 3 times by using 0.75kg of dichloromethane, merging organic phases, and distilling under reduced pressure to remove the solvent to obtain a solid;
adding 0.1kg of 3,3' -dichlorobenzidine, 0.33kg of 33% sodium nitrite aqueous solution, 0.28kg of 36% concentrated hydrochloric acid and 0.75kg of water into a reactor, reacting for 6.5h at 3 ℃, adding active carbon for decolorization after the reaction is completed, and filtering to obtain filtrate; adding 0.55kg of the obtained solid and 0.05kg of sodium hydroxide into 1.2kg of water, stirring and mixing uniformly, cooling to 12 ℃, adding glacial acetic acid to regulate the pH of a reaction system to 6.7, obtaining a coupling solution, adding the obtained coupling solution into the obtained filtrate, stirring and reacting for 2.5h, heating to 85 ℃ and continuing to react for 1.5h, keeping the pH of the system in the reaction process to be 6.3, cooling to 28 ℃ after the reaction is finished, filtering, washing the obtained filter cake with deionized water for 4 times, drying, adding the dried product into 0.065kg of trifluoroacetic acid and 1.5kg of dichloromethane, reacting for 13h at 28 ℃, and distilling under reduced pressure to remove the solvent after the reaction is finished, thereby obtaining the amino-terminated pigment orange 13 derivative.
Preparation of organic pigment for pigment orange 13-based ink:
under the protection of nitrogen, 0.1kg of end amino pigment orange 13 derivative is added into 0.8kg of dimethylacetamide, after stirring and dissolution, 0.12kg of 3, 4-benzophenone tetracarboxylic dianhydride is added into the mixture to react for 13 hours at 4 ℃, and after the reaction is finished, 0.5kg of the reaction liquid with the volume ratio of 2.3 is added: 1, heating the acetic anhydride-picoline mixed solution to 80 ℃, continuing to react for 32 hours, cooling to 28 ℃ after the reaction is finished, adding 1.3kg of absolute ethyl alcohol into the mixed solution, filtering, washing the obtained filter cake with deionized water for 4 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13.
Example 4 preparation of end amino pigment orange 13 derivative:
adding 0.1kg of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 0.32kg of 4- (boc-amino) phenol into 1.2kg of dimethyl sulfoxide, stirring and dissolving, then adding 0.19kg of potassium carbonate and 0.0018kg of cetyltrimethylammonium bromide, heating to 88 ℃, stirring and reacting for 26 hours, filtering after the reaction is finished, adding 0.9kg of water into the obtained filtrate, stirring and mixing uniformly, extracting for 2 times with 0.9kg of dichloromethane, merging organic phases, and distilling under reduced pressure to remove the solvent to obtain a solid;
adding 0.1kg of 3,3' -dichlorobenzidine, 0.38kg of 34% sodium nitrite aqueous solution, 0.29kg of 37% concentrated hydrochloric acid and 0.9kg of water into a reactor, reacting for 7.5h at 4 ℃, adding active carbon for decolorization after the reaction is completed, and filtering to obtain filtrate; adding 0.6kg of the obtained solid and 0.055kg of sodium hydroxide into 1.4kg of water, stirring and mixing uniformly, cooling to 14 ℃, adding glacial acetic acid to regulate the pH of a reaction system to 6.9, obtaining coupling solution, adding the obtained coupling solution into the obtained filtrate, stirring and reacting for 2.9h, heating to 88 ℃ and continuing to react for 1.8h, keeping the pH of the system in the reaction process to be 6.4, cooling to 29 ℃ after the reaction is finished, filtering, washing the obtained filter cake with deionized water for 4 times, drying, adding the dried product into 0.07kg of trifluoroacetic acid and 1.9kg of dichloromethane, reacting for 14h at 28 ℃, and distilling under reduced pressure to remove the solvent after the reaction is finished, thus obtaining the amino-terminated pigment orange 13 derivative.
Preparation of organic pigment for pigment orange 13-based ink:
under the protection of nitrogen, 0.1kg of end amino pigment orange 13 derivative is added into 0.9kg of dimethylformamide, after stirring and dissolving, 0.14kg of 3, 4-benzophenone tetracarboxylic dianhydride is added into the mixture, the mixture is reacted for 14 hours at the temperature of 4 ℃, and after the reaction is finished, 0.55kg of the mixture is added into the obtained reaction solution, wherein the volume ratio is 2.4:1, heating the acetic anhydride-picoline mixed solution to 83 ℃, continuing to react for 35 hours, cooling to 28 ℃ after the reaction is finished, adding 1.4kg of absolute ethyl alcohol into the mixed solution, filtering, washing the obtained filter cake with deionized water for 4 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13.
Example 5 preparation of end amino pigment orange 13 derivative:
adding 0.1kg of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 0.35kg of 4- (boc-amino) phenol into 1.5kg of dimethyl sulfoxide, stirring and dissolving, then adding 0.2kg of sodium carbonate and 0.002kg of cetyltrimethylammonium bromide, heating to 90 ℃, stirring and reacting for 30 hours, filtering after the reaction is finished, adding 1kg of water into the obtained filtrate, stirring and mixing uniformly, extracting for 3 times by using 1kg of dichloromethane, merging organic phases, and distilling under reduced pressure to remove the solvent to obtain a solid;
adding 0.1kg of 3,3' -dichlorobenzidine, 0.4kg of 35% sodium nitrite aqueous solution, 0.3kg of 38% concentrated hydrochloric acid and 1kg of water into a reactor, reacting for 8 hours at 5 ℃, adding active carbon for decolorization after the reaction is completed, and filtering to obtain filtrate; adding 0.62kg of the obtained solid and 0.06kg of sodium hydroxide into 1.5kg of water, stirring and mixing uniformly, cooling to 15 ℃, adding glacial acetic acid to regulate the pH of a reaction system to 7, obtaining coupling liquid, adding the obtained coupling liquid into the obtained filtrate, stirring and reacting for 3 hours, heating to 90 ℃ and continuing to react for 2 hours, keeping the pH of the system in the reaction process to be 6.5, cooling to 30 ℃ after the reaction is finished, filtering, washing the obtained filter cake with deionized water for 5 times, drying, adding the dried product into 0.08kg of trifluoroacetic acid and 2kg of dichloromethane, reacting at 30 ℃ for 15 hours, and distilling under reduced pressure to remove the solvent after the reaction is finished, thus obtaining the amino-terminated pigment orange 13 derivative.
Preparation of organic pigment for pigment orange 13-based ink:
under the protection of nitrogen, 0.1kg of end amino pigment orange 13 derivative is added into 1kg of N-methyl-2-pyrrolidone, after stirring and dissolving, 0.15kg of 3, 4-benzophenone tetracarboxylic dianhydride is added into the mixture, the mixture is reacted for 15 hours at 5 ℃, and after the reaction is finished, 0.6kg of the mixture is added into the obtained reaction solution with the volume ratio of 2.5:1, heating the acetic anhydride-picoline mixed solution to 85 ℃, continuing to react for 36 hours, cooling to 30 ℃ after the reaction is finished, adding 1.5kg of absolute ethyl alcohol into the mixed solution, filtering, washing the obtained filter cake with deionized water for 5 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13.
Example 6 preparation of end amino pigment orange 13 derivative:
adding 0.1kg of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 0.35kg of 4- (boc-amino) phenol into 0.8kg of dimethyl sulfoxide, stirring and dissolving, then adding 0.15kg of potassium carbonate and 0.002kg of cetyltrimethylammonium bromide, heating to 80 ℃, stirring and reacting for 30 hours, filtering after the reaction is finished, adding 0.75kg of water into the obtained filtrate, stirring and mixing uniformly, extracting 3 times by using 0.75kg of dichloromethane, merging organic phases, and distilling under reduced pressure to remove the solvent to obtain a solid;
adding 0.1kg of 3,3' -dichlorobenzidine, 0.4kg of 30% sodium nitrite aqueous solution, 0.25kg of 38% concentrated hydrochloric acid and 0.6kg of water into a reactor, reacting for 8 hours at 0 ℃, adding active carbon for decolorization after the reaction is completed, and filtering to obtain filtrate; adding 0.6kg of the obtained solid and 0.04kg of sodium hydroxide into 1kg of water, stirring and mixing uniformly, cooling to 10 ℃, adding glacial acetic acid to regulate the pH of a reaction system to 6.5, obtaining coupling liquid, adding the obtained coupling liquid into the obtained filtrate, stirring and reacting 2h, heating to 80 ℃ for continuous reaction for 2 hours, keeping the pH of the system in the reaction process to be 6.5, cooling to 25 ℃ after the reaction is finished, filtering, washing the obtained filter cake with deionized water for 4 times, drying, adding the dried product into 0.06kg of trifluoroacetic acid and 1.5kg of dichloromethane, reacting at 30 ℃ for 12 hours, and distilling under reduced pressure to remove the solvent after the reaction is finished, thus obtaining the end amino pigment orange 13 derivative.
Preparation of organic pigment for pigment orange 13-based ink:
under the protection of nitrogen, adding 0.1kg of end amino pigment orange 13 derivative into 0.9kg of dimethylacetamide, stirring and dissolving, adding 0.07kg of 3, 4-benzophenone tetracarboxylic dianhydride into the mixture, reacting for 10 hours at 5 ℃, and adding 0.6kg of the mixture into the obtained reaction solution with the volume ratio of 2:1, heating the acetic anhydride-picoline mixed solution to 85 ℃, continuing to react for 24 hours, cooling to 25 ℃ after the reaction is finished, adding 1.1kg of absolute ethyl alcohol into the mixed solution, filtering, washing the obtained filter cake with deionized water for 5 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13.
The organic pigment for the pigment orange 13-based ink prepared in examples 1-6 is subjected to thermogravimetric analysis, the temperature range is 30-550 ℃, the heating rate is 10 ℃/min, the experimental results are shown in table 1, and the results in table 1 show that the initial decomposition temperature of the organic pigment for the pigment orange 13-based ink prepared in the invention is above 400 ℃, and the organic pigment has good high temperature resistance.
The organic pigment for the pigment orange 13-based ink prepared in examples 1 to 6 was evaluated for light resistance according to detection standards GB1710-79, tested for water resistance, oil resistance, acid resistance and alkali resistance according to GB 5211.5-2008-T, and tested for pigment oil absorption according to GB1712-79, respectively; as shown in Table 2, it is clear from the results of Table 2 that the organic pigment for pigment orange 13-based ink prepared in examples 1 to 6 of the present invention has light resistance of 8, and has higher light resistance and superior water resistance, oil resistance, acid resistance and alkali resistance than the commercially available pigment orange 13.
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. An organic pigment for ink based on pigment orange 13, characterized in that: the structural formula is as follows:
；
a method for preparing the organic pigment for pigment orange 13-based ink, comprising the steps of: adding 1 part by weight of an amino-terminated pigment orange 13 derivative into 5-10 parts by weight of an aprotic polar solvent under the protection of nitrogen, stirring and dissolving, adding 0.7-1.5 parts by weight of 3, 4-benzophenone tetracarboxylic dianhydride into the solvent, reacting for 10-15 hours at 0-5 ℃, adding 4-6 parts by weight of an acetic anhydride-methylpyridine mixed solution into the obtained reaction solution after the reaction is finished, heating to 70-85 ℃, continuing to react for 24-36 hours, cooling to 25-30 ℃ after the reaction is finished, adding 10-15 parts by weight of absolute ethyl alcohol into the reaction solution, filtering, washing the obtained filter cake with deionized water for 3-5 times, and drying to obtain the organic pigment for the printing ink based on pigment orange 13;
the end is provided withThe structural formula of the amino pigment orange 13 derivative is as follows:。
2. the organic pigment for pigment orange 13 based ink according to claim 1, wherein: the aprotic polar solvent is dimethylformamide, dimethylacetamide or N-methyl-2-pyrrolidone.
3. The organic pigment for pigment orange 13 based ink according to claim 1, wherein: the volume ratio of acetic anhydride to picoline in the acetic anhydride-picoline mixed solution is 2-2.5: 1.
4. the organic pigment for pigment orange 13 based ink according to claim 1, wherein: the amino-terminated pigment orange 13 derivative is prepared by the following method:
1) Adding 1 part by weight of 2- (3, 5-difluorophenyl) -5-methyl-2, 4-dihydro-3H-pyrazol-3-one and 2-3.5 parts by weight of 4- (boc-amino) phenol into 8-15 parts by weight of dimethyl sulfoxide, stirring and dissolving, then adding 1.5-2 parts by weight of alkali and 0.01-0.02 part by weight of cetyltrimethylammonium bromide, heating to 80-90 ℃, stirring and reacting for 18-30 hours, filtering after the reaction is finished, adding 5-10 parts by weight of water into the obtained filtrate, stirring and mixing uniformly, extracting 2-3 times by using 5-10 parts by weight of dichloromethane, merging organic phases, and distilling under reduced pressure to remove a solvent to obtain a solid;
2) Adding 1 part by weight of 3,3' -dichlorobenzidine, 2.5-4 parts by weight of sodium nitrite aqueous solution, 2.5-3 parts by weight of concentrated hydrochloric acid and 5-10 parts by weight of water into a reactor, reacting for 5-8 hours at 0-5 ℃, adding active carbon for decoloring after the reaction is completed, and filtering to obtain filtrate; adding 5-6.2 parts of the solid obtained in the step 1) and 0.4-0.6 part of sodium hydroxide into 10-15 parts of water, uniformly stirring and mixing, cooling to 10-15 ℃, and then adding glacial acetic acid to adjust the pH of a reaction system to 6.5-7 to obtain coupling liquid; adding the obtained coupling solution into the obtained filtrate, stirring and reacting for 2-3 hours, heating to 80-90 ℃ and continuing to react for 1-2 hours, keeping the pH of the system in the reaction process to be 6-6.5, cooling to 25-30 ℃ after the reaction is completed, filtering, washing the obtained filter cake with deionized water for 3-5 times, drying, adding the dried product into 0.5-0.8 part of trifluoroacetic acid and 10-20 parts of dichloromethane, reacting for 12-15 hours at 25-30 ℃, and distilling under reduced pressure to remove the solvent after the reaction is completed to obtain the amino-terminated pigment orange 13 derivative.
5. The organic pigment for pigment orange 13 based ink according to claim 4, wherein: the alkali in the step 1) is potassium carbonate or sodium carbonate.
6. The organic pigment for pigment orange 13 based ink according to claim 4, wherein: and in the step 2), the mass concentration of the concentrated hydrochloric acid is 35-38%.
7. The organic pigment for pigment orange 13 based ink according to claim 4, wherein: and 2) the mass concentration of the sodium nitrite aqueous solution in the step 2) is 30-35%.
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Denomination of invention: An organic pigment for ink based on pigment orange 13 and its preparation method Granted publication date: 20240102 Pledgee: Shandong Penglai Rural Commercial Bank Co.,Ltd. Pledgor: PENGLAI XINGUANG PIGMENT CHEMICAL Co.,Ltd. Registration number: Y2024980009573 |