CN107603272B - Glycan molecule be coupled diketopyrrolo-pyrrole compound yellow pigment preparation in application, yellow pigment and yellow pigment preparation method - Google Patents

Glycan molecule be coupled diketopyrrolo-pyrrole compound yellow pigment preparation in application, yellow pigment and yellow pigment preparation method Download PDF

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CN107603272B
CN107603272B CN201710955892.4A CN201710955892A CN107603272B CN 107603272 B CN107603272 B CN 107603272B CN 201710955892 A CN201710955892 A CN 201710955892A CN 107603272 B CN107603272 B CN 107603272B
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CN107603272A (en
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李秀梅
季维
齐浩
王赫
王建
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Longkou United Chemical Co.,Ltd.
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LONGKOU UNION CHEMICAL CO Ltd
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Abstract

The present invention relates to the glycan molecules of general formula (I) to be coupled application of the diketopyrrolo-pyrrole compound in yellow pigment preparation, wherein R1For H, Br, Cl, F, CN, C1‑8Linear or branched alkyl group, aromatic alkyl substituted or unsubstituted, C1‑8Straight or branched alkoxyl, C1‑8Monosubstituted or disubstituted amino；A is monosaccharide groups, disaccharide base or three glycosyls；B is H or monosaccharide groups identical with A, disaccharide base or three glycosyls.The invention further relates to a kind of yellow pigments and preparation method thereof.

Description

Glycan molecule be coupled diketopyrrolo-pyrrole compound yellow pigment preparation in application, The preparation method of yellow pigment and yellow pigment
Technical field
The present invention relates to UV pigment for printing ink production field, specifically glycan molecule is coupled diketopyrrolo-pyrrole chemical combination Object yellow pigment preparation in application, yellow pigment and yellow pigment preparation method.
Background technique
In recent years, it is desirable that the cry of environmentally protective printing grows to even greater heights, and the advantage of environmentally friendly UV ink is also increasingly prominent.Regardless of It is protection environment or application effect, all shows environmentally friendly UV ink up-trend.The country such as the U.S., Japan, South Korea exists Vigorously promote the use environmentally friendly UV ink.It by be the following environment-friendly ink optimal selection, development prospect is boundless.Pigment conduct One of the important source material of ink is printed, only ink does not provide necessary distinct color, and the indexs such as tinting strength, tinting power, mobile performance are more It is the quality that will have a direct impact on UV ink.
In the prior art, yellow pigment is mainly by 3,3- dichloro-benzidine and dianisidine mixing diazonium salt and antifebrin Compound is coupled and is made.When such yellow pigment is applied to UV ink, dispersibility, the liquidity scale are general.
Summary of the invention
Technical assignment of the invention is in view of the above shortcomings of the prior art, to provide a kind of glycan molecule coupling diketone pyrrolo- Application of the azole compounds in yellow pigment preparation.
The further technical assignment of the present invention is to provide a kind of yellow pigment；
Further technical assignment is to provide the preparation method of above-mentioned yellow pigment to the present invention.
The glycan molecule indicated the present invention provides the following general formula (I) is coupled diketopyrrolo-pyrrole compound in yellow pigment system Application in standby:
Wherein, R1For H, Br, Cl, F, CN, C1-8Linear or branched alkyl group, aromatic alkyl substituted or unsubstituted, C1-8Straight chain Or branched alkoxy, C1-8Monosubstituted or disubstituted amino；
A is monosaccharide groups, disaccharide base or three glycosyls:
Monosaccharide 1- are substituted by the mixture of α or β or both, such as glucose, 1,5-anhydroglucitol, mannose, half Lactose, fructose, ribose, 2-deoxyribosyl, xylose, arabinose, lyxose；
The position 1- of disaccharide or 6- carbon atoms are coupled with the nitrogen-atoms in formula (I), such as lactose, sucrose, maltose；
The 6- position carbon atom of trisaccharide and the nitrogen-atoms in formula (I) are coupled, such as gentianose, gossypose；
B is H or monosaccharide groups identical with A, disaccharide base or three glycosyls.
Above-mentioned glycan molecule is coupled the hydrophily that diketopyrrolo-pyrrole compound itself has had so as to keep high Aqueous medium dispersion stabilization is implemented to be surface-treated, adjusts the particle of pigment according to the smaller water solubility of the degree of polymerization to surface of pigments The size and distribution, the physical aspect of particle and surface polarity feature of bigger partial size, are dispersed in pigment in UV resin system There are higher tinctorial strength and ideal dispersion effect.
Glycan molecule of the present invention coupling diketopyrrolo-pyrrole compound has a fabulous water solubility, and A is monosaccharide groups, B be H or Monosaccharide groups identical with A.
A using the glucose monosaccharide base of following structural formula, mannose monosaccharide base or galactolipin monosaccharide groups when can reach Best-of-breed technology effect:
Preferably, R1For H, Cl, C1-8Linear or branched alkyl group, aromatic alkyl substituted or unsubstituted, and work as R1For H, Cl Or it can reach best-of-breed technology effect when methyl.
Yellow pigment of the invention, in preparation process the following steps are included:
S1. diazo-reaction
Under stirring by 3,3- dichloro-benzidine be added hydrochloric acid solution in, dispersion after a certain period of time, under low temperature with sodium nitrite Solution carries out diazo-reaction, removes excessive sodium nitrite and obtains diazotization solution I；
S2. coupling reaction
S21. antifebrin compound and glycan molecule coupling diketopyrrolo-pyrrole compound are dissolved in alkaline solution, are obtained To coupling component solution II；
S22. coupling component solution II is added in aqueous acetic acid, generates antifebrin compound and glycan molecule coupling two Ketone pyrrolopyrrole compound precipitate, pH are adjusted to 4.5~6.5, and temperature is adjusted to 18-70 DEG C, obtains Coupling Solution III；
S23. diazotization solution I obtained by step S1 is added in Coupling Solution III, obtains yellow mill base；
S3. it post-processes
Yellow mill base is post-treated to obtain yellow pigment,
It is that the glycan molecule that general formula (I) indicates is coupled diketone that glycan molecule described in step S2, which is coupled diketopyrrolo-pyrrole compound, Pyrrolopyrrole compound.
Preferably, dianisidine can also be added in hydrochloric acid solution in step S1, to reach the mesh of adjustment form and aspect 's.
Each raw material reaches ideal technical effect using following weight proportion Shi Junneng in step S1:
The weight proportion of each raw material is preferred in step S1 are as follows:
The concrete operation method of step S1: after water and mixed in hydrochloric acid, be added under stirring condition 3,3- dichloro-benzidine (and connection Anise amine), it is dispersed with stirring 2-3 hours.It is on the rocks to be cooled to -3 DEG C hereinafter, addition sodium nitrite solution, generation is reacted with hydrochloric acid Nitrite, then with 3,3- dichloro-benzidine (and dianisidine) react generate diazonium salt, 0 DEG C stirring 0.5-1.5 hours.With Sulfamic acid destroys excessive sodium nitrite, and terminal is slightly blue to KI starch paper, obtains diazonium salt solution I.
Each raw material reaches ideal technical effect using following weight proportion Shi Junneng in step S2:
The weight proportion of each raw material is preferred in step S2 are as follows:
Preferably, antifebrin compound described in step S21 is for 2.4- dimethylacetamide antifebrin and to methyl second The mixture of acyl antifebrin perhaps acetoacetanilide or chloro- 2, the 5- dimethoxy acetyl-acetanilide of 4-, or Adjacent methyl vinyl antifebrin, perhaps to methoxyl group acetoacetanilide perhaps to chloracetyl antifebrin or adjacent carboxyl second Acyl antifebrin.
In step S21, alkali can be dissolved in antifebrin compound and glycan molecule coupling diketopyrrolo-pyrrole compound Property solution after, anionic surfactant or nonionic surfactant are added, to wish to reach yellow pigment in application system Tinctorial strength, coloured light or form and aspect, rheological characteristic, levelability, transparency, glossiness, fastness to light and fastness to weathering, solvent resistance Can, the performances such as different dispersibility.
The alkaline solution is preferably sodium hydrate aqueous solution or potassium hydroxide aqueous solution.
Preferably, coupling component solution II is at the uniform velocity added in aqueous acetic acid with 5-45min in step S22.
In order to be further improved the hydrophily of yellow pigment, make pigment glycan molecule coupling two in an aqueous medium in synthesis process Ketone pyrrolopyrrole compound is reacted to surface of pigments completely, and pigment is made to have ideal dispersibility, step S22 in UV resin It can also include: the compositional liquor progress surface that anionic surfactant and nonionic surfactant are added into reaction system The weight ratio of modification, anionic surfactant and nonionic surfactant is preferably 2:(1-4).
The anionic surfactant is alkylbenzene sulfonate, alkylsulfonate, fatty acid sulfoalkyl ester, succinate Sulfonate, alkylnaphthalene sulfonate or alkyl glyceryl ether sulfonate；
The nonionic surfactant is fatty alcohol polyoxyethylene ether, alkyl phenol polyoxyethylene ether or fatty acid polyoxy second Alkene ether.
In step S23, diazotization solution I obtained by step S1 is at the uniform velocity preferably added by Coupling Solution III with 50~200min In.
Preferably, step S3 includes:
It is modified to pigment progress surface that surfactant and/or hyper-dispersant are added into yellow mill base；
And/or: rosin resin is added in Xiang Huangse mill base, resinification processing is carried out to pigment；
And/or: pigment derivative is added in Xiang Huangse mill base, pigmentation processing is carried out to pigment.
The surfactant is preferably alkylbenzene sulfonate, alkylsulfonate, fatty acid sulfoalkyl ester, succinate sulphur The anionic surfactants such as hydrochlorate, alkylnaphthalene sulfonate or alkyl glyceryl ether sulfonate；The hyper-dispersant preferably disperses Agent 17000,24000；The rosin resin is superfine rosin or newtrex；The pigment derivative is DCB (3,3- dichloro connection Aniline) with the synthetic of AASP (p-sulfonic acid methyl vinyl antifebrin).
When antifebrin compound is for 2.4- dimethylacetamide antifebrin and to the mixture of methyl vinyl antifebrin, Step S2, the concrete operation method of S3:
S2. coupling reaction
S21. 120 parts of water are heated to 30 DEG C, 10-15 parts of alkaline solutions is added, are added with stirring 15-20 parts of 2.4- Dimethylacetamide antifebrin, 1-5 parts are coupled diketopyrrolo-pyrrole to methyl vinyl antifebrin and 3-10 parts of glycan molecules Conjunction object dissolves transparent altogether.Obtain coupling component solution II；
S22.100 parts of water and 4-6 parts of acetic acid are mixed into aqueous acetic acid, add coupling component solution II within control 5-15 minutes Enter into aqueous acetic acid, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl antifebrin and glycan molecule idol Determination of Vicinal Diketones pyrrolopyrrole compound generates white precipitate.PH=6-7, solution temperature obtain Coupling Solution to 60-70 DEG C Ⅲ；
S23. diazonium salt solution I is added to generation yellow mill base in 40-60 DEG C of solution III with 50-90 minutes.
S3. it post-processes
Yellow mill base is stirred 0.5-1.5 hours, pH=3-5, the rosin that 20-30 parts of mass percentages are 15% is added Solution carries out resinification processing to pigment, stirs 30-50 minutes, and 0-5 parts of surfactants and 1-2 parts of hyper-dispersants are added, right Pigment carries out surface and is modified, and stirs 10-30 minutes, is warming up to 80-90 DEG C, keeps the temperature 140-160 minutes, and 2-3 parts of pigment are added and spread out Biology stirs 10-20 minutes, is cooled to 50 DEG C hereinafter, filters pressing, washing.Filtration cakes torrefaction removes moisture, obtains environmentally friendly UV ink and uses PY13 pigment.
PY13 color chemistry structural formula:
When antifebrin compound is acetoacetanilide, the step S2, concrete operation method of S3:
S2. coupling reaction
S21. 300-400 parts of water are heated to 30 DEG C, 15-100 parts of alkaline solutions is added, are added with stirring 40-60 Part acetoacetanilide and 4-10 part glycan molecules are coupled diketopyrrolo-pyrrole compounds and dissolve altogether transparent, and it is molten to obtain coupling component Liquid II；
S22. 200-240 parts of water and 20-30 parts of acetic acid are mixed into aqueous acetic acid, control 5-15 minutes for coupling component Solution II is added in aqueous acetic acid, generates white acetoacetanilide and glycan molecule is coupled diketopyrrolo-pyrrole compound Generate white precipitate.PH=4.5-5.5, solution temperature obtain Coupling Solution III to 20-25 DEG C；
S23. diazonium salt solution I is added to generation yellow mill base in 20-25 DEG C of Coupling Solution III with 50-150 minutes.
S3. it post-processes
Yellow mill base is stirred 0.5-1.5 hours, pH=3-5, nonionic surfactant is added, is stirred 15-25 minutes. 95 DEG C are warming up to, keeps the temperature 120 minutes, pigment derivative is added, is stirred 5-15 minutes, is cooled to 70 DEG C hereinafter, filters pressing, washing. Filtration cakes torrefaction removes moisture, obtains environment-friendly ink PY12 pigment.
PY12 color chemistry structural formula:
When antifebrin compound is 4- chloro- 2,5- dimethoxy acetyl-acetanilide, the step S2, concrete operations of S3 Method:
S2. coupling reaction
S21. 100 parts of water are heated to 30 DEG C, 20-30 parts of alkaline solutions is added, are added with stirring 30-50 parts of 4- Chloro- 2,5- dimethoxy acetyl-acetanilide and 6-10 parts of glycan molecule coupling diketopyrrolo-pyrrole compounds dissolve thoroughly altogether It is bright.Obtain coupling component solution II；
S22. 120 parts of water and 10-15 parts of acetic acid are mixed into aqueous acetic acid, control 30-40 minutes molten by coupling component Liquid II is added in aqueous acetic acid, generates chloro- 2, the 5- dimethoxy acetyl-acetanilide (AS-IRG) of white 4- and sugar Son coupling diketopyrrolo-pyrrole compound generates white precipitate.3-10 portions of anionic surfactants and nonionic table is added The compositional liquor of face activating agent stirs 15 minutes.PH=5.5-6, solution temperature obtain Coupling Solution III to 15-25 DEG C；
S23. diazonium salt solution I is added in 15-25 DEG C of Coupling Solution III with 190-210 minutes and generates orange-yellow color Slurry.
S3. it post-processes
Orange-yellow mill base is stirred 0.5-1.5 hours, pH=4-4.5, newtrex solution is added, is stirred 15-25 minutes, 1-3 portion anionic surfactants are added, stirs 5-15 minutes, is warming up to 90 DEG C, heat preservation 15-25 minutes, be cooled to 70 DEG C with Under.Filters pressing, washing.Filter cake obtains environment-friendly ink PY83 yellow pigment by drying and removing moisture.
Newtrex solution preparation method: 100 parts of water are heated to 100 DEG C, are added newtrex 5-10 parts, stir 60 points Clock makes it completely dissolved transparent, and rosin solution is cooled to 50-55 DEG C, newtrex solution can be obtained.
PY83 color chemistry structural formula:
Glycan molecule coupling diketopyrrolo-pyrrole compound of the present invention can be prepared according to the following steps: formula (II) institute What the compound and formula (III) compound represented shown was replaced in organic solvent in the presence of organic base or inorganic base Reaction obtains the coupling diketopyrrolo-pyrrole compound of glycan molecule shown in formula (I):
Compound shown in formula (II):
Wherein, R1For H, Br, Cl, F, CN, C1-8Linear or branched alkyl group, aromatic alkyl substituted or unsubstituted, C1-8Straight chain Or branched alkoxy, C1-8Monosubstituted or disubstituted amino；
Compound shown in formula (III):
Wherein, P is benzyl, acetyl or benzoyl base；Glycan molecule is monosaccharide groups.
R1Preferably H, Cl or methyl.
Glycan molecule is preferably glucose monosaccharide base, mannose monosaccharide base or galactose monosaccharide base.
P is preferably acetyl or benzoyl base.
The inorganic base is preferably sodium carbonate, potassium carbonate, cesium carbonate or sodium bicarbonate；The organic base be preferably pyridine, Triethylamine or p dimethylamino pyridine；The organic solvent can be dimethylformamide, pyridine, tetrahydrofuran, methylene chloride, Toluene, preferably pyridine or dimethylformamide.
By taking glucose is coupled as an example, above-mentioned preparation method is illustrated:
[method A]
Glucose obtains pentaacetylglucose (1a) after acetyl group is protected, and further prepares in the presence of hydrogen bromide Obtain the 1- tetra-acetylated glucose of bromo (1b).Succinic acid diisopropyl ester and p-chlorobenzyl cyanide in ferric chloride catalyst and 120 degree are heated in the presence of sodium tert-amyl alcohol in tert-pentyl alcohol to react three hours, is generated to double chlorphenyl-Isosorbide-5-Nitraes-diketone pyrrolo- pyrrole Cough up dye composition (1c).Then the 1- tetra-acetylated Portugals of bromo are used in solvent dimethylformamide in the presence of potassium carbonate Grape sugar (1b) carries out sugared coupling reaction for the dye composition (1c), by controlling the 1- tetra-acetylated glucose of bromo (1b) Equivalents for 1c is 1.2:1, can smoothly obtain the target product of monosaccharide molecule coupling.
The temperature of the coupling reaction can control between 60-120 degree, carry out to control when the reaction at a lower temperature The longer reaction time is made to complete this reaction, the refining spearation of the target compound 1d of acetyl group protection can use silicagel column It completes to obtain in the organic solvents such as ethyl alcohol by being precipitated, filtering by the way that toluene is added in reaction solution.Acquired monosaccharide Four acetyl compound 1d are coupled, by methyl alcohol or the in the mixed solvent of methanol and water sloughs acetyl protection using potassium carbonate Base finally obtains the target product 1 of monosaccharide coupling of the present invention.Deprotection reaction can also be in sodium hydroxide, potassium hydroxide, hydrogen-oxygen In the presence of changing the inorganic bases such as lithium, completed in methyl alcohol in zero degree to stirring at room temperature；Deprotection reaction can also be in sodium ethoxide Or it is completed in methanol or alcohol solvent in zero degree to room temperature in the presence of sodium methoxide.Many methods can be used to refine above-mentioned Target product 1 obtained in reaction.Such as use silica gel post separation or the method being precipitated using solvent.Wherein solvent is precipitated Method is to first pass through vacuum distillation after completion of the reaction to remove most of organic solvent, is then made by addition organic solvent desired 1 Precipitation of target compound.The organic solvent being typically chosen includes methanol, ethyl alcohol, toluene, propyl alcohol, butanol, isopropanol etc., Tetrahydrofuran can also be used.Ethylene glycol diethyl ether, glycol dimethyl ether and ethyl acetate etc..The reaction being finally collected by filtration Product is washed with above-mentioned precipitation solvent can be obtained pure target product.
[method B]
It is main with method A this method describe the method for preparing disaccharide molecule coupling labeled diketopyrrolo-pyrrole compound Difference is to implement sugar coupling instead for dye composition 1c to obtain disaccharide molecule coupling labeled diketopyrrolo-pyrrole compound When answering formula, the equivalent for needing to control tetra-acetylated sugared bromine compounds is to be twice in compound 1c or using more tetra-acetylated Sugared bromine compounds, and need to be appropriately extended the reaction time (or improving reaction temperature) to ensure to obtain the production of disaccharide molecule coupling labeled Object.Other reaction steps and essentially identical for the refining methd and method A of reaction product.
Compared with prior art, glycan molecule coupling diketopyrrolo-pyrrole compound answering in yellow pigment preparation of the present invention With and yellow pigment have it is following prominent the utility model has the advantages that
(1) addition glycan molecule is coupled diketopyrrolo-pyrrole chemical combination in the yellow pigment production for being applied to environmental protection UV ink Object, due to introducing > C=O ,-Cl and complex metal atom in pigment molecule structure, to enhance pigment compound molecule Application performance itself, such as low-molecular-weight fat alcohols are formed by affinity interactions such as hydrogen bond, polarity effect, Van der Waals forces " anchoring " effect, is scattered in pigment particles in carrier, and the dipole moment of compound polarity size is allowed similar not contain with existing The compound of polar group forms newborn pigment particles surface as carrier cladding, prevents face compared to essential improvement has occurred Material particle reassociates.To improve the effect for being in pigment dispersion and dispersion stabilization of such compound.Therefore it utilizes Glycan molecule coupling diketopyrrolo-pyrrole compound preparation UV pigment for printing ink has more obvious application prospect and preferably application Performance.
(2) this hydrophilic compounds are added in pigment synthesis process can not only improve pigment in the dispersion of applicating medium Property, moreover it is possible to improve fluidity and levelability of the pigment in ink.Table is reduced to the maximum extent during preparing UV ink Original dosage of surfactant is reduced to 1-5% by 15-20% by the usage amount of face activating agent, dispersing agent and pluronic polymer, The use of such even completely omitted surfactant.But in the case where guaranteeing product quality, amplitude peak reduction is produced into This.
Detailed description of the invention
Attached drawing 1 is embodiment 3-12 yellow pigment PY13 preparation flow figure；
Attached drawing 2 is embodiment 13-23 yellow pigment PY12 preparation flow figure；
Attached drawing 3 is embodiment 24-32 yellow pigment PY83 preparation flow figure.
Embodiment
The present invention can be described in more detail in following preparation embodiment, experimental example, but the invention is not limited in any way.
Unless otherwise instructed, the content of following each ingredients used is weight percentage content.
The synthesis of [embodiment 1] single molecules of glucose coupling compound 1
(1) synthesis of compound 1a:
Glucose (1.8g, 10mmol) and potassium acetate (5.2g, 10.5mmol) are added in round-bottomed flask, and acetic acid is added Acid anhydride (9mL) is dissolved, and reaction temperature is transferred to 90 DEG C, after solid is completely dissolved, stirs 3h at 90 DEG C.Reaction terminates Afterwards, reaction solution is poured into separatory funnel to and is added 100mL ethyl acetate, organic phase is then washed with water, is added after extraction Sodium bicarbonate aqueous solution washs organic phase, until organic phase is generated without blistering, finally uses saturated common salt water washing again, organic phase is used Anhydrous sodium sulfate is dry.After being filtered to remove solid sodium sulfate, solution is evaporated under reduced pressure and removes solvent, obtains compound crude product, Ethyl alcohol recrystallization is finally used, white solid powder 1a (3.80g) is obtained.
(2) synthesis of compound 1b:
Compound 1a (2.0g, 5.13mmol) is added in 50mL round-bottomed flask, it is with anhydrous methylene chloride (5mL) that its is molten The acetum (2.5mL) of 33% hydrobromic acid is then slowly added dropwise in solution, reacts at room temperature 2h.After reaction, reaction solution is poured into In separatory funnel and 100mL methylene chloride is added, organic phase is washed with water, is washed again with sodium bicarbonate aqueous solution after extraction organic Phase finally uses saturated common salt water washing until bubble-free generates, and organic phase is dry with anhydrous sodium sulfate.It is filtered to remove sodium sulphate After solid, solution being evaporated under reduced pressure and removes solvent, crude product passes through silica gel chromatography (petroleum ether: ethyl acetate=4:1), Obtain white flaky solid 1b (1.81g).
(3) synthesis of compound 1c:
The ferric trichloride of metallic sodium (2.30g, 100mmol), tert-pentyl alcohol (50mL) and catalytic amount is added to the reaction of three necks In bottle, 50 DEG C are cooled to after stirring 1 hour at 100 DEG C.Mixture is added after p-Cyanochlorobenzene (5.48g, 40mmol) is added The tert-amyl alcohol solution of ni-isopropyl succinate (4.00g, 20mmol) is slowly added dropwise to 100 DEG C in heat.At 120 DEG C after being added dropwise Lower reaction 3 hours.It is cooled to room temperature.Be slowly added to glacial acetic acid tune pH be 7.0, then be added first alcohol and water (1:2, v:v, 100mL), it flows back 2 hours.Cold filtration and dry pale red powder solid (5.01g).
(4) synthesis of compound 1d:
1c (1.28g, 3.6mmol) and potassium carbonate (593mg, 4.3mmol) are added in 50mL dimethylformamide, heating To 90 DEG C, 15min is stirred.The dimethyl formamide solution of 1b (1.77g, 4.3mmol) is slowly added dropwise.Continue after being added dropwise anti- Answer 2h.It is cooled to room temperature, reaction solution pours into separatory funnel to and be added 200mL ethyl acetate, water washing organic phase, then with full And brine It, after organic phase anhydrous sodium sulfate drying, silica gel chromatography (petroleum ether: ethyl acetate=4:1) is obtained Red solid 1d (1.74g).
(5) synthesis of compound 1:
In 50mL round-bottomed flask be added compound 1d (687mg, 1mmol), dissolved with methanol (20mL), then plus Enter potassium carbonate (828mg, 6mmol), stirs 1h at room temperature.After reaction, reaction solution is filtered, obtained filtrate decompression distillation Solvent is removed, crude product isolates and purifies (methanol 30%+ methylene chloride 70%) with silicagel column partition method, finally uses Rotary Evaporators Solvent of going out obtains red solid compound 1 (492mg).
Nuclear magnetic resoance spectrum:1H NMR(400MHz,D2O), ppm:7.85 (4H, J=13.3Hz, doublet), 7.67 (4H, J =13.3Hz, doublet), 4.87 (1H, J=9Hz, doublets), 3.80 (1H, J=12.6Hz, triplets), 3.72-3.49 (4H, multiplet), 3.45 (1H, J=9.0Hz, triplets).13C NMR(100MHz,D2O), ppm:168.2,165.1, 142.6,137.5,136.6,133.5,132.3,128.7,120.2,91.6,82.7,77.5,72.2,71.2,61.9.
Mass spectrum: MS, m/z:519.06 [M+H]+。
[embodiment 2] bimolecular glucose coupling compound 2 synthesizes:
(1) synthesis of compound 2d:
1c (1.28g, 3.6mmol) and potassium carbonate (1.242g, 9mmol) are added in 50mL DMF, are warming up to 100 DEG C, Stir 15min.The DMF solution of 1b (3.70g, 9mmol) is slowly added dropwise.The reaction was continued after being added dropwise 2h.It is cooled to room temperature, it will Reaction solution pours into separatory funnel and is added 200mL ethyl acetate, water washing organic phase, then with saturated common salt water washing, organic Mutually with after anhydrous sodium sulfate drying, silica gel chromatography (petroleum ether: ethyl acetate=4:1) obtains red solid 2d (2.53g)。
(2) synthesis of compound 2:
In 50mL round-bottomed flask be added compound 2d (1.02g, 1mmol), dissolved with methanol (30mL), then plus Enter potassium carbonate (1.66g, 12mmol), stirs 3h at room temperature.After reaction, reaction solution is filtered, obtained filtrate decompression is steamed Most of solvent is removed in distillation, and crude product is slowly added drop-wise in the ethyl alcohol (about 100mL) of ice bath, and red objects compound is just precipitated, The product being collected by filtration finally obtains red solid compound 2 (647mg) using cold ethanol washing is used.
Yield: 95.1%
Nuclear magnetic resoance spectrum:1H NMR(400MHz,D2O), ppm:7.86 (4H, J=13.3Hz, doublet), 7.68 (4H, J =13.3Hz, doublet), 4.86 (2H, J=9.0Hz, doublets), 3.82 (2H, J=12.6Hz, triplets), 3.71-3.42 (8H, multiplet), 3.38 (2H, J=9.0Hz, triplets).13C NMR(100MHz,D2O), ppm:165.2,142.7, 136.5,133.5,128.7,120.2,91.7,82.8,77.6,72.2,71.3,61.7.
Mass spectrum: MS, m/z:681.12 [M+H]+。
The following are raw materials used in the preparation method of yellow pigment:
Hydrochloric acid: the mass percentage of HCl is 30%；
Caustic soda: the mass percentage of NaOH is 20%；
Sodium nitrite: NaNO2Mass percentage be 25%；
Acetic acid: the mass percentage of HAc is 80%；
3,3- dichloro-benzidine: the mass percentage of DCB is 100%；
Dianisidine: mass percentage 100%；
This amine of 2.4- dimethylacetamide acetyl: the mass percentage of AAMX is 98%；
To methyl vinyl antifebrin: mass percentage 98%；
The chloro- 2,5- dimethoxy acetyl-acetanilide (AS-IRG) of 4-: mass percentage 98%；
Glycan molecule is coupled diketopyrrolo-pyrrole compound: embodiment 1 or the preparation of 2 the method for embodiment, quality percentage Content is 98%；
Sulfamic acid: mass percentage 98%；
Superfine rosin: mass percentage 100%；
Newtrex: mass percentage 100%；
[embodiment 3]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, be added with stirring 3,3- dichloro-benzidine 8g and Dispersion 2.5 hours is mixed in dianisidine 0.5g, on the rocks to be cooled to -5 DEG C hereinafter, addition sodium nitrite 17.7g, stirring 1 Hour, excessive sodium nitrite is destroyed with sulfamic acid, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 3g, Stirring and dissolving is transparent, and caustic soda 11.4g is added, and stirring obtains even summation component lysate II；
100ml water, 5.3g acetic acid is added in coupling container, aqueous acetic acid is mixed into, by even summation component lysate II It controls 10 minutes and is added, pH=6.4 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl second The precipitate of anilide and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.1, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and fatty alcohol polyoxyethylene ether surfactant 3g, hyper-dispersant 17000 is added 2g is surface-treated pigment, is warming up to 80 DEG C, keeps the temperature 150 minutes, and 3g pigment derivative is added, and stirs 10 minutes, cooling To 50 DEG C or less.Filters pressing, washing.Filtration cakes torrefaction removes moisture, obtains 1# environmental protection UV ink PY13 pigment.
Rosin solution is prepared: 500ml water being heated to 100 DEG C, superfine rosin 75g is added, stirring makes it for 60 minutes completely It dissolves transparent, is cooled to 50-55 DEG C, obtains rosin solution.
[embodiment 4]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 3g, stirs It is transparent to mix dissolution, caustic soda 11.4g is added, stirring obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.7 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.3, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and fatty acid sulfoalkyl ester surfactant 5g, 22000 2g of hyper-dispersant is added, Pigment is surface-treated, is warming up to 80 DEG C, keeps the temperature 150 minutes, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filtration cakes torrefaction removes moisture, obtains 2# environmental protection UV ink PY13 pigment.
The preparation method of rosin solution is same as Example 3.
[embodiment 5]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 3g, stirs It is transparent to mix dissolution, caustic soda 11.4g is added, stirring is added fatty acid sulfoalkyl ester surfactant 5g, obtains coupling component solution Ⅱ；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.2 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.8, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and 22000 2g of hyper-dispersant is added, is surface-treated to pigment, is warming up to 80 DEG C, 150 minutes are kept the temperature, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filtration cakes torrefaction Moisture is removed, 3# environmental protection UV ink PY13 pigment is obtained.
The preparation method of rosin solution is same as Example 3.
[embodiment 6]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 5g, stirs It is transparent to mix dissolution, caustic soda 11.4g stirring is added, fatty alcohol polyoxyethylene ether surfactant 5g is added, it is molten to obtain coupling component Liquid II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.4 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.9, and 15% (mass percent concentration) rosin resin solution 25g is added, right Pigment carries out resinification processing, stirs 30 minutes, and 22000 2g of hyper-dispersant is added, is surface-treated, is warming up to pigment 80 DEG C, 150 minutes are kept the temperature, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filter cake is dry Dry removing moisture obtains 4# environmental protection UV ink PY13 pigment.
The preparation method of rosin solution is same as Example 3.
[embodiment 7]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 5g, stirs It is transparent to mix dissolution, caustic soda 11.4g stirring is added, obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.6 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.3, and 15% (mass percent concentration) rosin resin solution 25g is added, right Pigment carries out resinification processing, stirs 30 minutes, and 22000 2g of hyper-dispersant is added, is surface-treated, is warming up to pigment 80 DEG C, 150 minutes are kept the temperature, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filter cake is dry Dry removing moisture obtains 5# environmental protection UV ink PY13 pigment.
The preparation method of rosin solution is same as Example 3.
[embodiment 8]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 6g, Stirring and dissolving is transparent, and caustic soda 11.4g stirring is added, obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.8 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, is added fatty alcohol polyoxyethylene ether surfactant 8g Obtain Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.8, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and 22000 2g of hyper-dispersant is added, is surface-treated to pigment, is warming up to 80 DEG C, 150 minutes are kept the temperature, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filtration cakes torrefaction Moisture is removed, 6# environmental protection UV ink PY13 pigment is obtained.
The preparation method of rosin solution is same as Example 3.
[embodiment 9]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 6g, Stirring and dissolving is transparent, and caustic soda 11.4g is added, and stirring obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.6 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, is added fatty alcohol polyoxyethylene ether surfactant 8g Obtain Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.2, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and 22000 2g of hyper-dispersant is added, is surface-treated to pigment, is warming up to 80 DEG C, 150 minutes are kept the temperature, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filtration cakes torrefaction Moisture is removed, 7# environmental protection UV ink PY13 pigment is obtained.
The preparation method of rosin solution is same as Example 3.
[embodiment 10]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound Caustic soda 11.4g is added in 10g, stirring, and dissolution is transparent, obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.5 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.8, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and 22000 hyper-dispersant 2g are added, is surface-treated to pigment, is warming up to 80 DEG C, 150 minutes are kept the temperature, pigment derivative 5g is added, stirs 10 minutes, is cooled to 50 DEG C or less.Filters pressing, washing.Filtration cakes torrefaction Moisture is removed, 8# environmental protection UV ink PY13 pigment is obtained.
The preparation method of rosin solution is same as Example 3.
[embodiment 11]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 6g Stirring, addition caustic soda 11.4g dissolution is transparent, obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.4 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound.Fatty alcohol polyoxyethylene ether surfactant 4g is added Obtain Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4, and 15% (mass percent concentration) rosin resin solution 25g is added to pigment Resinification processing is carried out, is stirred 30 minutes, 22000 hyper-dispersant 2g are added, pigment is surface-treated, is warming up to 80 DEG C, Heat preservation 150 minutes, be added alkyl glyceryl ether sulfonate 2g, be added pigment derivative 3g, stir 10 minutes, be cooled to 50 DEG C with Under.Filters pressing, washing.Filtration cakes torrefaction removes moisture, obtains 9# environmental protection UV ink PY13 pigment.
The preparation method of rosin solution is same as Example 3.
[embodiment 12]
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, is added with stirring 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, on the rocks to be cooled to -5 DEG C hereinafter, sodium nitrite 17.7g is added, stirring 1 hour is destroyed with sulfamic acid Excessive sodium nitrite, terminal is slightly blue to KI starch paper, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, is warming up to 30 DEG C, is added with stirring 2.4- dimethylacetamide acetyl Aniline 17.6g, the coupling of glycan molecule described in methyl vinyl antifebrin 2g and embodiment 1 diketopyrrolo-pyrrole compound 6g is stirred It mixes, caustic soda 11.4g is added, dissolution is transparent, obtains coupling component solution II；
100ml water, 5.3g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is controlled It makes 10 minutes and is added, pH=6.7 is warming up to 70 DEG C, generates white 2.4- dimethylacetamide antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, obtains Coupling Solution III；
Diazonium salt solution I is added in 50 DEG C of Coupling Solutions III by control for 90 minutes, generates yellow mill base；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.1, and 15% (mass percent concentration) rosin resin solution 25g is added to face Material carries out resinification processing, stirs 30 minutes, and 2g hyper-dispersant 22000 is added, is surface-treated to pigment, is warming up to 80 DEG C, 150 minutes are kept the temperature, 5g alkyl glyceryl ether sulfonate is added, pigment derivative 3g is added, stirs 10 minutes, is cooled to 50 DEG C Below.Filters pressing, washing.Filtration cakes torrefaction removes moisture, obtains 10# environmental protection UV ink PY13 pigment.
The preparation method of rosin solution is same as Example 3.
[embodiment 13]
S1. diazo-reaction
200ml water, 16g hydrochloric acid, 3.3- dichloro-benzidine 32g, dianisidine 2g are added in diazo-reaction container, Stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 18g, react with hydrochloric acid generation nitrite, then Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.KI Starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
300ml water is added in coupling component dissolution vessel, acetoacetanilide 50g is added in 20 DEG C of addition caustic soda 75g, Glycan molecule described in embodiment 2 is coupled diketopyrrolo-pyrrole compound 6g, dissolves transparent.Coupling component solution II is obtained,
240ml water is added in coupling container, acetic acid 23.7g stirring is mixed into aqueous acetic acid, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 10 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=5.4, obtains idol by 25 DEG C of solution temperature Solution III is closed,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 90 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.2, and nonionic surfactant aliphatic acid polyethenoxy ether 9g, stirring is added 20 minutes, 95 DEG C are warming up to, keeps the temperature 120 minutes, pigment derivative 5g is added, stirs 10 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 1# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 14]
S1. diazo-reaction
250ml water, 46g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 100g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g, embodiment 2 is added The glycan molecule is coupled diketopyrrolo-pyrrole compound 4g, dissolves transparent.Coupling component solution II is obtained,
200ml water is added in coupling container, the stirring of 25.2g acetic acid is mixed into aqueous acetic acid, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=4.6,25 DEG C of solution temperature are coupled Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 100 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.4, and nonionic surfactant alkyl phenol polyoxyethylene ether 9g, stirring is added 20 minutes, 95 DEG C are warming up to, keeps the temperature 120 minutes, pigment derivative 5g is added, stirs 10 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 2# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 15]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water is added in coupling component dissolution vessel, acetoacetanilide 50g is added in 20 DEG C of addition caustic soda 100g, Glycan molecule described in embodiment 2 is coupled diketopyrrolo-pyrrole compound 8g, dissolves transparent.Coupling component solution II is obtained,
200ml water is added in coupling container, the stirring of 25.2g acetic acid is mixed into aqueous acetic acid, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=4.9,25 DEG C of solution temperature are coupled Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 100 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.3, and nonionic surfactant fatty alcohol polyoxyethylene ether 9g, stirring is added 20 minutes, 95 DEG C are warming up to, keeps the temperature 120 minutes, pigment derivative 5g is added, stirs 10 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 3# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 16]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g, 1 institute of embodiment is added Glycan molecule coupling diketopyrrolo-pyrrole compound 8g is stated, is dissolved transparent.Coupling component solution II is obtained,
200ml water, 25.2g acetic acid is added in coupling container, is mixed into aqueous acetic acid, coupling component solution II is adjusted Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetoacetyl by whole temperature for control 10 minutes The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=4.8,25 DEG C of solution temperature obtain Coupling Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 100 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.7, and the nonionic surfactant fatty alcohol polyoxyethylene ether of 15g is added, Stirring 20 minutes is warming up to 95 DEG C, keeps the temperature 120 minutes, and pigment derivative 5g is added, and stirs 10 minutes, is cooled to 70 DEG C or less. Filters pressing, washing.Filter cake obtains 4# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 17]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 100g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g, embodiment 1 is added The glycan molecule is coupled diketopyrrolo-pyrrole compound 8g, dissolves transparent.Coupling component solution II is obtained,
200ml water is added, acetic acid 25.2g stirring is mixed into aqueous acetic acid, coupling component solution II is adjusted temperature extremely 14 DEG C, mixing aqueous acetic acid was added in coupling component solution II in control 10 minutes, generates white acetoacetanilide and sugar The precipitate of molecule coupling labeled diketopyrrolo-pyrrole compound.PH=4.6, obtains Coupling Solution III by 25 DEG C of solution temperature,
Diazonium liquor I was added to in coupling container with 100 minutes generation yellow mill base in 25 DEG C of Coupling Solutions III；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.2, and nonionic surfactant alkyl phenol polyoxyethylene ether 15g is added, stirs It mixes 20 minutes, is warming up to 95 DEG C, keep the temperature 120 minutes, pigment derivative 10g is added, stir 10 minutes, be cooled to 70 DEG C or less. Filters pressing, washing.Filter cake obtains 5# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 18]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g, 1 institute of embodiment is added Glycan molecule coupling diketopyrrolo-pyrrole compound 4g is stated, is dissolved transparent.Coupling component solution II is obtained,
200ml water is added in coupling container, the stirring of 25.2g acetic acid is mixed into aqueous acetic acid, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=5.2,25 DEG C of solution temperature are coupled Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 50 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=3.9, and nonionic surfactant aliphatic acid polyethenoxy ether 15g is added, stirs It mixes 20 minutes, is warming up to 95 DEG C, keep the temperature 120 minutes, pigment derivative 10g is added, stir 10 minutes, be cooled to 70 DEG C or less. Filters pressing, washing.Filter cake obtains 6# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 19]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g, 2 institute of embodiment is added Glycan molecule coupling diketopyrrolo-pyrrole compound 8g is stated, is dissolved transparent.Coupling component solution II is obtained,
200ml water is added in coupling container, the stirring of 25.2g acetic acid is mixed into aqueous acetic acid, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=5.0,25 DEG C of solution temperature are coupled Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 50 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.5, and anionic surfactant alkylbenzene sulfonate 10g, stirring 20 is added Minute, 95 DEG C are warming up to, keeps the temperature 120 minutes, pigment derivative 15g is added, stirs 10 minutes, is cooled to 70 DEG C or less.Filters pressing, Washing.Filter cake obtains 7# environment-friendly ink PY12 yellow pigment by drying and removing moisture.
[embodiment 20]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks to be cooled to -3 DEG C hereinafter, addition sodium nitrite 15g solution, reacts with hydrochloric acid and generate nitrous Hydrochlorate, then diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction, 0 DEG C is stirred 1 hour.It is transferred to sulfamic acid Terminal.KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water is added in coupling component dissolution vessel, acetoacetanilide 50g is added in 20 DEG C of addition caustic soda 20g, Glycan molecule described in embodiment 2 is coupled diketopyrrolo-pyrrole compound 8g, dissolves transparent.Coupling component solution II is obtained,
200ml water is added in coupling container, 25.2g acetic acid is mixed into aqueous acetic acid, coupling component solution II is adjusted Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetoacetyl by whole temperature for control 10 minutes The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=4.9,25 DEG C of solution temperature obtain Coupling Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 50 minutes；
S3. it post-processes
Yellow mill base stirs 1 hour, pH=4.0, and anionic surfactant alkylsulfonate 4g and nonionic table is added Face activating agent alkyl phenol polyoxyethylene ether 6g is stirred 20 minutes, is warming up to 95 DEG C, keeps the temperature 120 minutes, and pigment derivative is added 15g stirs 10 minutes, is cooled to 70 DEG C or less.Filters pressing, washing.Filter cake obtains 8# environment-friendly ink use by drying and removing moisture PY12 yellow pigment.
[embodiment 21]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction again, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g, 2 institute of embodiment is added Glycan molecule coupling diketopyrrolo-pyrrole compound 10g is stated, is dissolved transparent.Coupling component solution II is obtained,
200ml water, the stirring of 25.2g acetic acid are added in coupling container, aqueous acetic acid is mixed into, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=4.8,25 DEG C of solution temperature are coupled Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 50 minutes；
S3. it post-processes
Yellow mill base stir 1 hour, pH=4.1, be added anionic surfactant fatty acid sulfoalkyl ester 4g and it is non-from Sub- surfactant aliphatic acid polyethenoxy ether 6g is stirred 20 minutes, is warming up to 95 DEG C, keeps the temperature 120 minutes, and it is derivative that pigment is added Object 5g stirs 10 minutes, is cooled to 70 DEG C or less.Filters pressing, washing.Filter cake obtains 9# environment-friendly ink by drying and removing moisture With PY12 yellow pigment.
[embodiment 22]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine are added in diazo-reaction container 3g, stirring to pulp 2.5 hours.It is on the rocks to be cooled to -3 DEG C hereinafter, addition sodium nitrite 15g solution, reacts with hydrochloric acid and generate nitrous Hydrochlorate, then diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction, 0 DEG C is stirred 1 hour.It is transferred to sulfamic acid Terminal.KI starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water is added in coupling component dissolution vessel, acetoacetanilide 50g is added in 20 DEG C of addition caustic soda 20g, It dissolves transparent.Coupling component solution II is obtained,
200ml water, the stirring of 25.2g acetic acid are added in coupling container, aqueous acetic acid is mixed into, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin.PH=5.2,25 DEG C of solution temperature obtain Coupling Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 50 minutes；
S3. it post-processes
Yellow mill base stir 1 hour, pH=3.8, be added anionic surfactant fatty acid sulfoalkyl ester 5g and it is non-from Sub- surfactant aliphatic acid polyethenoxy ether 5g is stirred 20 minutes, is warming up to 95 DEG C, keeps the temperature 120 minutes, and it is derivative that pigment is added Object 5g stirs 10 minutes, is cooled to 70 DEG C or less.Filters pressing, washing.Filter cake obtains 10# environment-friendly ink by drying and removing moisture With PY12 yellow pigment.
[embodiment 23]
S1. diazo-reaction
250ml water, 14g hydrochloric acid, 3.3- dichloro-benzidine 28g and dianisidine 3g are added in diazo-reaction container Stirring to pulp, 2.5 hours.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 15g, react with hydrochloric acid generation nitrite, then Diazonium salt is generated with 3,3- dichloro-benzidine and dianisidine reaction, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.KI Starch paper is slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 26.5g caustic soda are added in coupling component dissolution vessel, acetoacetanilide 50g is added, dissolution is saturating It is bright, coupling component solution II is obtained,
200ml water is added in coupling container, the stirring of 25.2g acetic acid is mixed into aqueous acetic acid, by coupling component solution Mixing aqueous acetic acid is added in coupling component solution II to 14 DEG C, generates white acetyl by II adjustment temperature for control 10 minutes The precipitate of antifebrin.PH=4.9,25 DEG C of solution temperature obtain Coupling Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 150 minutes；
S3. it post-processes
Yellow mill base stir 1 hour, pH=4.6, be added anionic surfactant fatty acid sulfoalkyl ester 6g and it is non-from Sub- surfactant aliphatic acid polyethenoxy ether 4g is stirred 20 minutes, is warming up to 95 DEG C, keeps the temperature 120 minutes, and it is derivative that pigment is added Object 5g stirs 10 minutes, is cooled to 70 DEG C or less.Filters pressing, washing.Filter cake obtains 11# environment-friendly ink by drying and removing moisture With PY12 yellow pigment.
[embodiment 24]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g, stirring to pulp 2.5 are added in diazo-reaction container Hour.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 8.7g, react with hydrochloric acid generation nitrite, then with 3,3- dichloro Benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.It obtains Diazonium liquor I；
S2. coupling reaction
The water of 100ml, 30 DEG C of chloro- 2,5- dimethoxys of addition caustic soda 26.5g, 4- are added in coupling component dissolution vessel Glycan molecule described in acetyl-acetanilide (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 6g, and dissolution is saturating It is bright.Obtain coupling component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control is added in mixing aqueous acetic acid II adjustment temperature for 30-40 minutes, generates chloro- 2, the 5- dimethoxy of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Fatty acid sulphur is added Arrcostab 3g and alkyl phenol polyoxyethylene ether 2g compositional liquor stir 15 minutes.PH=5.6, obtains being coupled molten by 20 DEG C of solution temperature Liquid III,
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 5.2g, stirring make it completely dissolved within 60 minutes it is transparent, will be loose Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.2, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant sulphosuccinates 1g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 1# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 25]
S1. diazo-reaction
It is added 100ml water and 6.6g hydrochloric acid in diazo-reaction container, 3.3- dichloro-benzidine 15g, described in embodiment 1 Glycan molecule is coupled diketopyrrolo-pyrrole compound 6g stirring, disperses 2.5 hours.It is on the rocks to be cooled to -3 DEG C hereinafter, nitrous is added Sour sodium 8.7g reacts with hydrochloric acid and generates nitrite, then reacts with 3,3- dichloro-benzidine and generate diazonium salt, 10-15 DEG C of stirring 1 Hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.Obtain diazonium liquor I；
S2. coupling reaction
The water of 100ml is added in coupling component dissolution vessel, caustic soda 26.5g is added, chloro- 2, the 5- dimethoxy of 4- is added Acetyl-acetanilide (AS-IRG) 40g dissolves transparent.Obtain coupling component solution II；
120ml water is added in coupling container, 80% acetic acid 11.5g stirring is mixed into aqueous acetic acid.Group will be coupled Solution II is divided to adjust temperature to 30 DEG C, control is added in mixing aqueous acetic acid for 30-40 minutes, generates white 4- chloro- 2,5- The precipitate of dimethoxy acetyl-acetanilide (AS-IRG).Alkylbenzene sulfonate 2g and fatty alcohol polyoxyethylene ether 1g is added Compositional liquor stirs 15 minutes.PH=5.9, obtains Coupling Solution III by 20 DEG C of solution temperature,
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 5.2g, stirring make it completely dissolved within 60 minutes it is transparent, will be loose Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.3, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant fatty acid sulfoalkyl ester 1g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 2# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 26]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are added in diazo-reaction container, is dispersed with stirring 2.5 Hour.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 8.7g, react with hydrochloric acid generation nitrite, then with 3,3- dichloro Benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.It obtains Diazonium liquor I；
S2. coupling reaction
100ml water, 30 DEG C of chloro- 2,5- dimethoxy second of addition caustic soda 26.5g, 4- are added in coupling component dissolution vessel Acyl group antifebrin (AS-IRG) 40g dissolves transparent.Obtain coupling component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control is added in mixing aqueous acetic acid II adjustment temperature for 30-40 minutes, generates chloro- 2, the 5- dimethoxy of white 4- The precipitate of base acetyl-acetanilide (AS-IRG).Fatty acid sulfoalkyl ester 2g is added to compound with alkyl phenol polyoxyethylene ether 3g Liquid stirs 15 minutes.Glycan molecule described in embodiment 1 is added and is coupled diketopyrrolo-pyrrole compound 6g, pH=5.7, solution temperature 20 DEG C of degree, obtains Coupling Solution III；
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 5.2g, stirring make it completely dissolved within 60 minutes it is transparent, will be loose Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.0, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant alkylnaphthalene sulfonate 1g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 3# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 27]
S1. diazo-reaction
100ml water is added in diazo-reaction container and 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are dispersed with stirring 2.5 Hour.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 8.7g, react with hydrochloric acid generation nitrite, then with 3,3- dichloro Benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.It obtains Diazonium liquor I；
S2. coupling reaction
100ml water is added in coupling component dissolution vessel, chloro- 2, the 5- dimethoxy acetyl group of 4- is added in 26.5g caustic soda Glycan molecule described in antifebrin (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 6g, dissolves transparent.It obtains Coupling component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control is added in mixing aqueous acetic acid II adjustment temperature for 30-40 minutes, generates chloro- 2, the 5- dimethoxy of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Benzene sulfonamide is added Hydrochlorate 2g and fatty alcohol polyoxyethylene ether 1g compositional liquor stir 15 minutes.PH=5.5, obtains Coupling Solution by 20 DEG C of solution temperature Ⅲ；
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes,
100ml water is heated to 100 DEG C, is added newtrex 5.2g, stirring make it completely dissolved within 60 minutes it is transparent, will be loose Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.5, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant alkyl glyceryl ether sulfonate 1g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less. Filters pressing, washing.Filter cake obtains 4# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 28]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are added in diazo-reaction container, is dispersed with stirring 2.5 Hour.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 8.7g, react with hydrochloric acid generation nitrite, then with 3,3- dichloro Benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.It obtains Diazonium liquor I；
S2. coupling reaction
100ml water, 22g caustic soda, the chloro- 2,5- dimethoxy acetoaceto benzene of 4- are added in coupling component dissolution vessel Glycan molecule described in amine (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 10g, and dissolution is transparent, is coupled Component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control is added in mixing aqueous acetic acid II adjustment temperature for 30-40 minutes, generates chloro- 2, the 5- dimethoxy of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Anion table is added Face activating agent fatty acid sulfoalkyl ester 4g is stirred 15 minutes.PH=5.8, obtains Coupling Solution III by 20 DEG C of solution temperature；
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 10g, stirring make it completely dissolved within 60 minutes it is transparent, will be loose Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.4, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant fatty acid sulfoalkyl ester 1g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 5# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 29]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are added in diazo-reaction container, is dispersed with stirring 2.5 Hour.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 8.7g, react with hydrochloric acid generation nitrite, then with 3,3- dichloro Benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.It obtains Diazonium liquor I；
S2. coupling reaction
The chloro- 2,5- dimethoxy acetyl group second of water, 26.5g caustic soda, 4- of 100ml is added in coupling component dissolution vessel Glycan molecule described in anilide (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 10g, dissolves transparent.It obtains Coupling component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control is added in mixing aqueous acetic acid II adjustment temperature for 30-40 minutes, generates chloro- 2, the 5- dimethoxy of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Stirring 15 minutes. PH=5.7, obtains Coupling Solution III by 20 DEG C of solution temperature；
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, newtrex 10g is added, stirring makes it completely dissolved transparent, addition for 60 minutes Alkylbenzene sulfonate 5g and fatty alcohol polyoxyethylene ether 2g, stirring is transparent, and rosin solution is cooled to 50-55 DEG C.It is polymerize Rosin solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.5, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant alkylbenzene sulfonate 3g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 6# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 30]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are added in diazo-reaction container, is dispersed with stirring 2.5 Hour.It is on the rocks to be cooled to -3 DEG C hereinafter, sodium nitrite 8.7g solution is added, generation nitrite react with hydrochloric acid, then with 3,3- Dichloro-benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper. Obtain diazonium liquor I；
S2. coupling reaction
100ml water, 26.5g caustic soda, the chloro- 2,5- dimethoxy acetoaceto of 4- are added in coupling component dissolution vessel It is transparent that glycan molecule described in aniline (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 8g dissolution.It is coupled Component solution II；
120ml water, the stirring of 11.5g acetic acid are added in coupling container, is mixed into aqueous acetic acid.Anionic surface is added Coupling component solution II is adjusted temperature to 30 DEG C by activating agent sulphosuccinates 5g, and control is added to mixing in 30-40 minutes In aqueous acetic acid, generates chloro- 2, the 5- dimethoxy acetyl-acetanilide (AS-IRG) of white 4- and glycan molecule is coupled diketone The precipitate of pyrrolopyrrole compound.Stirring 15 minutes.PH=5.9, obtains Coupling Solution III by 20 DEG C of solution temperature,
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 10g, stirring make it completely dissolved within 60 minutes it is transparent, will be loose Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.3, and newtrex solution IV is added, and stirs 20 minutes, and anion is added Surfactant sulphosuccinates 3g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Pressure Filter, washing.Filter cake obtains 7# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[embodiment 31]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are added in diazo-reaction container, is dispersed with stirring 2.5 Hour.It is on the rocks to be cooled to -3 DEG C hereinafter, sodium nitrite 8.7g solution is added, generation nitrite react with hydrochloric acid, then with 3,3- Dichloro-benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper. Obtain diazonium liquor I；
S2. coupling reaction
100ml water, 26.5g caustic soda, the chloro- 2,5- dimethoxy acetoaceto of 4- are added in coupling component dissolution vessel Glycan molecule described in aniline (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 8g, and dissolution is transparent, is coupled Component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.Alkyl glycerylether is added Coupling component solution II is adjusted temperature to 30 DEG C, controls 30-40 minutes and be added by sulfonate 5g and alkyl phenol polyoxyethylene ether 4g Into mixing aqueous acetic acid, generates chloro- 2, the 5- dimethoxy acetyl-acetanilide (AS-IRG) of white 4- and glycan molecule is even The precipitate of Determination of Vicinal Diketones pyrrolopyrrole compound.Stirring 15 minutes.PH=5.8, obtains Coupling Solution by 20 DEG C of solution temperature Ⅲ；
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 8g, stirring make it completely dissolved within 60 minutes it is transparent, by rosin Solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.4, and newtrex solution IV is added, and stirs 20 minutes, and alkyl phenol is added Polyoxyethylene ether 3g is stirred 10 minutes, is warming up to 90 DEG C, is kept the temperature 20 minutes, is cooled to 70 DEG C or less.Filters pressing, washing.Filter cake warp It crosses and dries and removes moisture, obtain 8# environment-friendly ink PY83 yellow pigment.
[embodiment 32]
S1. diazo-reaction
100ml water, 6.6g hydrochloric acid, 3.3- dichloro-benzidine 15g are added in diazo-reaction container, is dispersed with stirring 2.5 Hour.It is on the rocks be cooled to -3 DEG C hereinafter, be added sodium nitrite 8.7g, react with hydrochloric acid generation nitrite, then with 3,3- dichloro Benzidine reaction generates diazonium salt, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch paper.It obtains Diazonium liquor I；
S2. coupling reaction
100ml water, 26.5g caustic soda, the chloro- 2,5- dimethoxy acetoaceto of 4- are added in coupling component dissolution vessel Glycan molecule described in aniline (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 8g, and dissolution is transparent, is coupled Component solution II；
120ml water is added in coupling container, the stirring of 11.5g acetic acid is mixed into aqueous acetic acid.Alkyl benzene sulphonate is added Coupling component solution II is adjusted temperature to 30 DEG C by salt 5g and fatty alcohol polyoxyethylene ether 4g, and control is added to mixed for 30-40 minutes It closes in aqueous acetic acid, generates chloro- 2, the 5- dimethoxy acetyl-acetanilide (AS-IRG) of white 4- and glycan molecule coupling two The precipitate of ketone pyrrolopyrrole compound sum.Stirring 15 minutes.PH=5.6, obtains Coupling Solution III by 20 DEG C of solution temperature；
Diazonium liquor I is added in 20 DEG C of Coupling Solutions III with 200 minutes and generates orange-yellow mill base；
S3. it post-processes
100ml water is heated to 100 DEG C, is added newtrex 8g, stirring make it completely dissolved within 60 minutes it is transparent, by rosin Solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.2, and fatty alcohol polyoxyethylene ether 3g is added, and newtrex solution is added IV, it stirs 20 minutes, stirs 10 minutes, control is warming up to 90 DEG C for 60 minutes, keeps the temperature 20 minutes, is cooled to 70 DEG C or less.Filters pressing, Washing.Filter cake obtains 9# environment-friendly ink PY83 yellow pigment by drying and removing moisture.
[experimental example]
It is detected using embodiment 3 to 32 gained yellow pigment of embodiment as sample, each data are shown in Table one, table two, table three.
One: PY13 yellow pigment experimental result of table
Two: PY12 yellow pigment experimental result of table
Three: PY83 yellow pigment experimental result of table

Claims (9)

1. application of the glycan molecule coupling diketopyrrolo-pyrrole compound that general formula (I) indicates in yellow pigment preparation:
Wherein, R1For H, Br, Cl, F, CN, C1-8Linear or branched alkyl group, C1-8Straight or branched alkoxyl, C1-8It is monosubstituted or double Substituted-amino；
A is monosaccharide groups, disaccharide base or three glycosyls:
Monosaccharide 1- are substituted by the mixture of α or β or both；
The position 1- of disaccharide or 6- carbon atoms are coupled with the nitrogen-atoms in formula (I)；
The 6- position carbon atom of trisaccharide and the nitrogen-atoms in formula (I) are coupled；
B is H or monosaccharide groups identical with A, disaccharide base or three glycosyls.
2. yellow pigment, which is characterized in that in its preparation process the following steps are included:
S1. diazo-reaction
Under stirring by 3,3- dichloro-benzidine be added hydrochloric acid solution in, dispersion after a certain period of time, under low temperature with sodium nitrite solution Diazo-reaction is carried out, the sodium nitrite for removing surplus obtains diazotization solution I；
S2. coupling reaction
S21. acetoacetanilide compound and glycan molecule coupling diketopyrrolo-pyrrole compound are dissolved in alkaline solution, are obtained To coupling component solution II, the acetoacetanilide compound is for 2.4- dimethylacetamide antifebrin and to methyl vinyl second The mixture of anilide perhaps acetoacetanilide or chloro- 2, the 5- dimethoxy acetyl-acetanilide of 4-, or adjacent first Base acetoacetanilide, perhaps to methoxyl group acetoacetanilide perhaps to chloracetyl antifebrin or adjacent carboxyl acetyl second Anilide；
S22. coupling component solution II is added in aqueous acetic acid, generates antifebrin compound and glycan molecule is coupled diketone pyrrole It coughs up and azole compounds precipitate, pH is adjusted to 4.5~6.5, temperature is adjusted to 18-70 DEG C, obtains Coupling Solution III；
S23. diazotization solution I obtained by step S1 is added in Coupling Solution III, obtains yellow mill base；
S3. it post-processes
Yellow mill base is post-treated to obtain yellow pigment,
Glycan molecule described in step S2 is coupled diketopyrrolo-pyrrole compound are as follows:
Wherein, R1For H, Br, Cl, F, CN, C1-8Linear or branched alkyl group, C1-8Straight or branched alkoxyl, C1-8It is monosubstituted or double Substituted-amino；
A is monosaccharide groups, disaccharide base or three glycosyls:
Monosaccharide 1- are substituted by the mixture of α or β or both；
The position 1- of disaccharide or 6- carbon atoms are coupled with the nitrogen-atoms in formula (I)；
The 6- position carbon atom of trisaccharide and the nitrogen-atoms in formula (I) are coupled；
B is H or monosaccharide groups identical with A, disaccharide base or three glycosyls.
3. yellow pigment according to claim 2, it is characterised in that: in step S1, the United Nations General Assembly's fennel is also added in hydrochloric acid solution Amine.
4. yellow pigment according to claim 3, it is characterised in that: the weight proportion of each raw material in step S1 are as follows:
5. yellow pigment according to claim 4, it is characterised in that the weight proportion of each raw material in step S2 are as follows:
6. the yellow pigment according to Claims 2 or 3, it is characterised in that step S22 includes: that anion is added into reaction system The compositional liquor of surfactant and nonionic surfactant carries out surface modification treatment, anionic surfactant and nonionic The weight ratio of surfactant is preferably 2:(1-4).
7. the yellow pigment according to Claims 2 or 3, it is characterised in that, will be obtained by step S1 with 50~200min in step S23 Diazotization solution I is at the uniform velocity added in Coupling Solution III.
8. the yellow pigment according to Claims 2 or 3, it is characterised in that step S3 includes:
It is modified to pigment progress surface that surfactant and/or hyper-dispersant are added into yellow mill base；
And/or:
Rosin resin is added into yellow mill base, resinification processing is carried out to pigment；
And/or:
Pigment derivative is added into yellow mill base, pigmentation processing is carried out to pigment.
9. the preparation method of yellow pigment, it is characterised in that the following steps are included:
S1. diazo-reaction
Under stirring by 3,3- dichloro-benzidine be added hydrochloric acid solution in, dispersion after a certain period of time, under low temperature with sodium nitrite solution Diazo-reaction is carried out, the sodium nitrite for removing surplus obtains diazotization solution I；
S2. coupling reaction
S21. acetoacetanilide compound and glycan molecule coupling diketopyrrolo-pyrrole compound are dissolved in alkaline solution, are obtained To coupling component solution II, the acetoacetanilide compound is for 2.4- dimethylacetamide antifebrin and to methyl vinyl second The mixture of anilide perhaps acetoacetanilide or chloro- 2, the 5- dimethoxy acetyl-acetanilide of 4-, or adjacent first Base acetoacetanilide, perhaps to methoxyl group acetoacetanilide perhaps to chloracetyl antifebrin or adjacent carboxyl acetyl second Anilide；
S22. coupling component solution II is added in aqueous acetic acid, generates antifebrin compound and glycan molecule is coupled diketone pyrrole Simultaneously azole compounds precipitate is coughed up, proper pH value and temperature is adjusted to, obtains Coupling Solution III；
S23. diazotization solution I obtained by step S1 is added in Coupling Solution III, obtains yellow mill base；
S3. it post-processes
Yellow mill base is post-treated to obtain yellow pigment,
Glycan molecule described in step S2 is coupled diketopyrrolo-pyrrole compound are as follows:
Wherein, R1For H, Br, Cl, F, CN, C1-8Linear or branched alkyl group, C1-8Straight or branched alkoxyl, C1-8It is monosubstituted or double Substituted-amino；
A is monosaccharide groups, disaccharide base or three glycosyls:
Monosaccharide 1- are substituted by the mixture of α or β or both；
The position 1- of disaccharide or 6- carbon atoms are coupled with the nitrogen-atoms in formula (I)；
The 6- position carbon atom of trisaccharide and the nitrogen-atoms in formula (I) are coupled；
B is H or monosaccharide groups identical with A, disaccharide base or three glycosyls.
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