CN107603272A - Glycan molecule is coupled application of the diketopyrrolo-pyrrole compound in yellow pigment preparation, the preparation method of yellow pigment and yellow pigment - Google Patents

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

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CN107603272A
CN107603272A CN201710955892.4A CN201710955892A CN107603272A CN 107603272 A CN107603272 A CN 107603272A CN 201710955892 A CN201710955892 A CN 201710955892A CN 107603272 A CN107603272 A CN 107603272A
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CN107603272B (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 application of the glycan molecule of formula (I) the coupling diketopyrrolo-pyrrole compound in yellow pigment preparation, wherein R1For H, Br, Cl, F, CN, C1‑8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, C1‑8Straight or branched alkoxyl, C1‑8Monosubstituted or disubstituted amino；A is monosaccharide groups, disaccharide base or three glycosyls；B be H or with A identicals monosaccharide groups, disaccharide base or three glycosyls.The invention further relates to a kind of yellow pigment 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 fields, specifically glycan molecule coupling diketopyrrolo-pyrrole chemical combination Application of the thing in yellow pigment preparation, the preparation method of yellow pigment and yellow pigment.
Background technology
In recent years, it is desirable to which the cry of green printing grows to even greater heights, and the advantage of environmentally friendly UV ink also increasingly highlights.No matter It is environmental protection, or application effect, all show 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 following environment-friendly ink optimal selection, development prospect is boundless.Pigment conduct One of important source material of printing-ink, only ink does not provide the indexs such as necessary distinct color, its tinting strength, tinting power, mobile performance more It is the quality that can directly influence UV ink.
In the prior art, yellow pigment is mainly by 3,3- dichloro-benzidine and dianisidine mixing diazol and antifebrin Compound is coupled and is made.When such yellow pigment is applied into UV ink, dispersiveness, the liquidity scale are general.
The content of the invention
The technical assignment of the present invention is to be directed to above-mentioned the deficiencies in the prior art, there is provided a kind of glycan molecule is coupled diketone pyrrolo- Application of the azole compounds in yellow pigment preparation.
Further technical assignment of the invention is to provide a kind of yellow pigment；
Further technical assignment of the invention is to provide the preparation method of above-mentioned yellow pigment.
The glycan molecule represented the invention provides following formulas (I) is coupled diketopyrrolo-pyrrole compound in yellow pigment system Application in standby：
Wherein, R1For H, Br, Cl, F, CN, C1-8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, C1-8Straight chain Or branched alkoxy, C1-8Monosubstituted or disubstituted amino；
A is monosaccharide groups, disaccharide base or three glycosyls：
Monose 1- positions are substituted by α or β or both mixture, such as glucose, 1,5-anhydroglucitol, mannose, half Lactose, fructose, ribose, 2-deoxyribosyl, xylose, arabinose, lyxose；
The 1- positions of disaccharide or 6- positions carbon atom are coupled with the nitrogen-atoms in formula (I), such as lactose, sucrose, maltose；
The 6- positions carbon atom of trisaccharide is coupled with the nitrogen-atoms in formula (I), such as gentianose, gossypose；
B be H or with A identicals monosaccharide groups, disaccharide base or three glycosyls.
The hydrophily that above-mentioned glycan molecule coupling diketopyrrolo-pyrrole compound has had in itself is so as to keeping high Aqueous medium dispersion stabilization, surface of pigments is implemented to be surface-treated, adjusts the particle of pigment according to the smaller water solubility of the degree of polymerization The size of bigger particle diameter and distribution, the physical aspect of particle and surface polarity feature, make pigment be dispersed in UV resin systems 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 With A identical monosaccharide groups.
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, C1-8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, and work as R1For H, Cl Or best-of-breed technology effect is can reach during methyl.
The yellow pigment of the present invention, comprise the following steps in its preparation process：
S1. diazo-reaction
Under stirring by 3,3- dichloro-benzidine add hydrochloric acid solution in, disperse certain time after, under low temperature with natrium nitrosum Solution carries out diazo-reaction, removes excessive natrium nitrosum and obtains diazo solution I；
S2. coupling reaction
S21. antifebrin compound and glycan molecule coupling diketopyrrolo-pyrrole compound are dissolved in alkaline solution, 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 adjustment obtains Coupling Solution III to 18-70 DEG C；
S23. diazo solution I obtained by step S1 is added in Coupling Solution III, obtains yellow mill base；
S3. post-process
Yellow mill base is post-treated to obtain yellow pigment,
Glycan molecule coupling diketopyrrolo-pyrrole compound described in step S2 is that the glycan molecule that formula (I) represents is coupled diketone Pyrrolopyrrole compound.
Preferably, in step S1, dianisidine can also be added in hydrochloric acid solution, to reach the mesh of adjustment form and aspect 's.
It can reach preferable technique effect when each raw material uses following weight proportion in step S1：
The weight proportion of each raw material is preferably in step S1：
Step S1 concrete operation method：After water and mixed in hydrochloric acid, 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 less than -3 DEG C, sodium nitrite solution is added, is generated with hydrochloric acid reaction Nitrite, then react generation diazol, 0 DEG C of stirring 0.5-1.5 hour with 3,3- dichloro-benzidine (and dianisidine).With Sulfamic acid destroys excessive natrium nitrosum, and terminal is slightly blue to KI starch papers, obtains diazonium salt solution I.
It can reach preferable technique effect when each raw material uses following weight proportion in step S2：
The weight proportion of each raw material is preferably in step S2：
Preferably, antifebrin compound described in step S21 is for 2.4- dimethylacetamides antifebrin and to methyl second The mixture of acyl antifebrin, either AAA or chloro- 2, the 5- dimethoxys acetyl-acetanilides of 4-, or Adjacent methyl vinyl antifebrin, either to methoxyl group AAA or 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, anion 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 performance such as different dispersiveness.
The alkaline solution is preferably sodium hydrate aqueous solution or potassium hydroxide aqueous solution.
Preferably, in step S22, coupling component solution II is at the uniform velocity added in aqueous acetic acid with 5-45min.
In order to further improve the hydrophily of yellow pigment, make pigment glycan molecule coupling two in aqueous medium in building-up process Ketone pyrrolopyrrole compound is reacted to surface of pigments completely, pigment is had preferably dispersiveness, step S22 in UV resins It can also include：The compositional liquor that anion surfactant and nonionic surfactant are added into reaction system carries out surface The weight ratio of modification, anion surfactant and nonionic surfactant is preferably 2:(1-4).
The anion surfactant is alkylbenzenesulfonate, alkylsulfonate, aliphatic acid sulfoalkyl ester, succinate Sulfonate, alkylnaphthalene sulfonate or alkyl glyceryl ether sulfonate；
The nonionic surfactant is AEO, APES or aliphatic acid polyoxy second Alkene ether.
In step S23, diazo 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：
Surfactant and/or hyper-dispersant are added into yellow mill base surface modification is carried out to pigment；
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.
The surfactant is preferably alkylbenzenesulfonate, alkylsulfonate, aliphatic acid sulfoalkyl ester, succinate sulphur The anion surfactants such as hydrochlorate, alkylnaphthalene sulfonate or alkyl glyceryl ether sulfonate；The hyper-dispersant is preferably scattered Agent 17000,24000；The rosin resin is superfine rosin or newtrex；The pigment derivative is that (3,3- dichloros join DCB Aniline) with AASP (p-sulfonic acid methyl vinyl antifebrin) synthetic.
When antifebrin compound is 2.4- dimethylacetamides antifebrin and the mixture to methyl vinyl antifebrin, Step S2, S3 concrete operation method：
S2. coupling reaction
S21. 120 parts of water are heated to 30 DEG C, add 10-15 part alkaline solutions, stir lower addition 15-20 parts 2.4- Dimethylacetamide antifebrin, 1-5 parts are coupled diketopyrrolo-pyrrole to methyl vinyl antifebrin and 3-10 parts glycan molecule Compound dissolves transparent altogether.Obtain coupling component solution II；
S22.100 parts water is mixed into aqueous acetic acid with 4-6 part acetic acid, and control 5-15 minutes add coupling component solution II Enter into aqueous acetic acid, generate white 2.4- dimethylacetamides 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. post-process
Yellow mill base is stirred 0.5-1.5 hours, pH=3-5, add the rosin that 20-30 parts weight/mass percentage composition is 15% Solution carries out resinification processing to pigment, stirs 30-50 minutes, adds 0-5 parts surfactant and 1-2 part hyper-dispersants, right Pigment carries out surface modification, stirs 10-30 minutes, is warming up to 80-90 DEG C, is incubated 140-160 minutes, adds 2-3 part pigment and spreads out Biology, 10-20 minutes are stirred, be cooled to less than 50 DEG C, press filtration, wash.Filtration cakes torrefaction removes moisture, obtains environmentally friendly UV ink and uses PY13 pigment.
PY13 color chemistry structural formulas：
When antifebrin compound is AAA, step S2, S3 concrete operation method：
S2. coupling reaction
S21. 300-400 part water is heated to 30 DEG C, adds 15-100 part alkaline solutions, stir lower addition 40-60 Part AAA and 4-10 parts glycan molecule coupling diketopyrrolo-pyrrole compound dissolve transparent altogether, and it is molten to obtain coupling component Liquid II；
S22. 200-240 parts water and 20-30 part acetic acid are mixed into aqueous acetic acid, control 5-15 minutes by coupling component Solution II is added in aqueous acetic acid, generates white AAA and glycan molecule coupling 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. post-process
Yellow mill base is stirred 0.5-1.5 hours, pH=3-5, add nonionic surfactant, stir 15-25 minutes. 95 DEG C are warming up to, is incubated 120 minutes, adds pigment derivative, stirs 5-15 minutes, less than 70 DEG C is cooled to, press filtration, washes. Filtration cakes torrefaction removes moisture, obtains environment-friendly ink PY12 pigment.
PY12 color chemistry structural formulas：
When antifebrin compound is 4- chloro- 2,5- dimethoxys acetyl-acetanilides, step S2, S3 concrete operations Method：
S2. coupling reaction
S21. 100 parts of water are heated to 30 DEG C, add 20-30 part alkaline solutions, stir lower addition 30-50 parts 4- Chloro- 2,5- dimethoxys acetyl-acetanilide and 6-10 parts glycan molecule coupling diketopyrrolo-pyrrole compound dissolve altogether It is bright.Obtain coupling component solution II；
S22. 120 parts of water and 10-15 part acetic acid are mixed into aqueous acetic acid, control 30-40 minutes are molten by coupling component Liquid II is added in aqueous acetic acid, generates chloro- 2, the 5- dimethoxys acetyl-acetanilides (AS-IRG) of white 4- and sugar Son coupling diketopyrrolo-pyrrole compound generates white precipitate.Add 3-10 parts anion surfactant and nonionic table The compositional liquor of face activating agent, stir 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. post-process
Orange-yellow mill base is stirred 0.5-1.5 hours, pH=4-4.5, adds newtrex solution, stir 15-25 minutes, Add 1-3 part anion surfactants, stir 5-15 minutes, be warming up to 90 DEG C, be incubated 15-25 minutes, be cooled to 70 DEG C with Under.Press filtration, washing.Filter cake removes moisture by drying, and obtains environment-friendly ink PY83 yellow pigments.
Newtrex solution compound method：100 parts of water are heated to 100 DEG C, add newtrex 5-10 parts, stir 60 points It is transparent that clock is completely dissolved it, and rosin solution is cooled into 50-55 DEG C, you can obtains newtrex solution.
PY83 color chemistry structural formulas：
Glycan molecule coupling diketopyrrolo-pyrrole compound of the present invention can be prepared according to the following steps：Formula (II) institute The compound shown is substituted in organic solvent with the compound shown in formula (III) in the presence of organic base or inorganic base Reaction, obtain the coupling diketopyrrolo-pyrrole compound of glycan molecule shown in formula (I)：
Compound shown in formula (II)：
Wherein, R1For H, Br, Cl, F, CN, C1-8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, 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 acid carbonate；The organic base be preferably pyridine, Triethylamine or p dimethylamino pyridine；The organic solvent can be dimethylformamide, pyridine, tetrahydrofuran, dichloromethane, Toluene, preferably pyridine or dimethylformamide.
So that glucose is coupled as an example, above-mentioned preparation method is illustrated：
【Method A】
Glucose obtains pentaacetylglucose (1a) after acetyl group is protected, and it is further prepared in the presence of hydrogen bromide Obtain the 1- tetra-acetylated glucose of position bromo (1b).Succinic acid diisopropyl ester and p-chlorobenzyl cyanide in ferric chloride catalyst and 120 degree are heated in tert-pentyl alcohol to react three hours, generate to double chlorphenyl-Isosorbide-5-Nitraes-diketone pyrrolo- pyrrole in the presence of sodium tert-amyl alcohol Cough up dye composition (1c).Then the 1- positions tetra-acetylated Portugal of bromo is 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 tetra-acetylated glucose of 1- positions bromo (1b) Equivalents for 1c is 1.2:1, you can smoothly obtain the target product of monosaccharide molecule coupling.
The temperature of the coupling reaction can be controlled between 60-120 degree, carry out to control during the reaction at a lower temperature The system longer reaction time completes this reaction, and the target compound 1d of acetyl group protection refining spearation can use silicagel column Completion can also be by the way that reaction solution be added in the organic solvents such as toluene, ethanol by separating out, filtering acquisition.Acquired monose 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 monose 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 caustic alcohol Or completed in the presence of sodium methoxide in methanol or alcohol solvent in zero degree to room temperature.Many methods can be used to refined above-mentioned The target product 1 obtained in reaction.Such as use silica gel post separation or the method separated out using solvent.Wherein solvent separates out Method is to first pass through vacuum distillation after completion of the reaction to remove most of organic solvent, then by add organic solvent make it is desired The Precipitation of target compound 1.The organic solvent being typically chosen includes, methanol, ethanol, 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 and can obtain pure target product.
【Method B】
The method for preparing disaccharide molecule coupling labeled diketopyrrolo-pyrrole compound is this method describe, it is main with method A Difference is to obtain disaccharide molecule coupling labeled diketopyrrolo-pyrrole compound, is implementing sugar coupling instead for dye composition 1c Answer during formula, it is necessary to which the equivalent for controlling tetra-acetylated sugared bromine compounds is to be twice in compound 1c or using more tetra-acetylated Sugared bromine compounds, and need the proper extension reaction time (or improving reaction temperature) to ensure to obtain the production of disaccharide molecule coupling labeled Thing.Other reactions steps and essentially identical for the process for purification 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 there is beneficial effect following prominent：
(1) glycan molecule coupling diketopyrrolo-pyrrole chemical combination is added in being produced applied to the yellow pigment of environmentally friendly UV ink Thing, due to being introduced in pigment molecule structure>C=O ,-Cl and complex metal atom, so as to enhance pigment compound molecule Application performance itself, such as low-molecular-weight fat alcohols, formed by affinity interactions such as hydrogen bond, polarity effect, Van der Waals forces " anchoring " acts on, and pigment particles is scattered in carrier, allows the dipole moment of compound polarity size similar not contained with existing There occurs essential improvement, the pigment particles surface for forming new life coats the compound phase ratio of polar group for carrier, prevents face Material particle reassociates.So as to improve the scattered effect for being and the dispersion stabilization in pigment of such compound.Therefore utilize Glycan molecule coupling diketopyrrolo-pyrrole compound, which prepares UV pigment for printing ink, more obvious application prospect and preferably application Performance.
(2) this hydrophilic compounds are added in pigment building-up process can not only improve pigment in the scattered of applicating medium Property, moreover it is possible to improve fluidity and levelability of the pigment in ink.Table is reduced to greatest extent during UV ink is prepared The usage amount of face activating agent, dispersant and pluronic polymer, original dosage of surfactant is reduced to 1-5% by 15-20%, The use of such even completely omitted surfactant.But in the case where ensureing product quality, amplitude peak is reduced and is produced into This.
Brief description of the drawings
Accompanying drawing 1 is embodiment 3-12 yellow pigment PY13 preparation flow figures；
Accompanying drawing 2 is embodiment 13-23 yellow pigment PY12 preparation flow figures；
Accompanying drawing 3 is embodiment 24-32 yellow pigment PY83 preparation flow figures.
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 compositions used is weight percentage content.
【Embodiment 1】Single molecules of glucose coupling compound 1 synthesizes
(1) compound 1a synthesis：
Glucose (1.8g, 10mmol) and potassium acetate (5.2g, 10.5mmol) are added in round-bottomed flask, and adds acetic acid Acid anhydride (9mL) is dissolved, and reaction temperature is transferred into 90 DEG C, and after solid is completely dissolved, 3h is stirred at 90 DEG C.Reaction terminates Afterwards, reaction solution is poured into separatory funnel and adds 100mL ethyl acetate, organic phase is then washed with water, is added after extraction Sodium bicarbonate aqueous solution washs organic phase, until organic phase produces without foaming, finally uses saturated common salt water washing again, organic phase is used Anhydrous sodium sulfate drying.After being filtered to remove solid sodium sulfate, solvent is distilled off in solution decompression, obtains compound crude product, Ethyl alcohol recrystallization is finally used, obtains white solid powder 1a (3.80g).
(2) compound 1b synthesis：
Compound 1a (2.0g, 5.13mmol) is added in 50mL round-bottomed flasks, it is with anhydrous methylene chloride (5mL) that its is molten Solution, the acetum (2.5mL) of 33% hydrobromic acid is then slowly added dropwise, reacts at room temperature 2h.After reaction terminates, reaction solution is poured into In separatory funnel and 100mL dichloromethane is added, organic phase is washed with water, is washed again with sodium bicarbonate aqueous solution after extraction organic Phase, until bubble-free produces, finally with saturated common salt water washing, organic phase anhydrous sodium sulfate drying.It is filtered to remove sodium sulphate After solid, solvent is distilled off in solution decompression, crude product passes through silica gel chromatography (petroleum ether：Ethyl acetate=4：1), Obtain white flaky solid 1b (1.81g).
(3) compound 1c synthesis：
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 being stirred 1 hour at 100 DEG C.Mixture is added after adding p-Cyanochlorobenzene (5.48g, 40mmol) Ni-isopropyl succinate (4.00g, 20mmol) tert-amyl alcohol solution 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.It is 7.0 to be slowly added to glacial acetic acid and adjust pH, then adds first alcohol and water (1:2, v:V, 100mL), flow back 2 hours.Cold filtration and dry pale red powder solid (5.01g).
(4) compound 1d synthesis：
1c (1.28g, 3.6mmol) and potassium carbonate (593mg, 4.3mmol) are added in 50mL dimethylformamides, heating To 90 DEG C, 15min is stirred.1b (1.77g, 4.3mmol) dimethyl formamide solution is slowly added dropwise.Continue after being added dropwise anti- Answer 2h.Room temperature is cooled to, reaction solution is poured into separatory funnel and adds 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), obtain Red solid 1d (1.74g).
(5) synthesis of compound 1：
Compound 1d (687mg, 1mmol) is added in 50mL round-bottomed flasks, is dissolved with methanol (20mL), is then added Enter potassium carbonate (828mg, 6mmol), stir 1h at room temperature.After reaction terminates, by reacting liquid filtering, obtained filtrate decompression distillation Solvent is removed, crude product isolates and purifies (methanol 30%+ dichloromethane 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, doublets), 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 it is 2-in-1 into：
(1) compound 2d synthesis：
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.1b (3.70g, 9mmol) DMF solution is slowly added dropwise.Continue to react 2h after being added dropwise.Room temperature is cooled to, will Reaction solution pours into separatory funnel and adds 200mL ethyl acetate, water washing organic phase, then with saturated common salt water washing, it is organic After phase anhydrous sodium sulfate drying, silica gel chromatography (petroleum ether：Ethyl acetate=4：1) red solid 2d, is obtained (2.53g)。
(2) synthesis of compound 2：
Compound 2d (1.02g, 1mmol) is added in 50mL round-bottomed flasks, is dissolved with methanol (30mL), is then added Enter potassium carbonate (1.66g, 12mmol), stir 3h at room temperature.After reaction terminates, by reacting liquid filtering, obtained filtrate decompression is steamed Most of solvent is removed in distillation, and crude product is slowly added drop-wise in the ethanol (about 100mL) of ice bath, just separates out red objects compound, The product being collected by filtration by being washed using cold ethanol, finally obtains red solid compound 2 (647mg) again.
Yield：95.1%
Nuclear magnetic resoance spectrum：1H NMR(400MHz,D2O), ppm:7.86 (4H, J=13.3Hz, doublets), 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]+。
Below to be raw materials used in the preparation method of yellow pigment：
Hydrochloric acid：HCl weight/mass percentage composition is 30%；
Caustic soda：NaOH weight/mass percentage composition is 20%；
Natrium nitrosum：NaNO2Weight/mass percentage composition be 25%；
Acetic acid：HAc weight/mass percentage composition is 80%；
3,3- dichloro-benzidine：DCB weight/mass percentage composition is 100%；
Dianisidine：Weight/mass percentage composition is 100%；
This amine of 2.4- dimethylacetamide acetyl：AAMX weight/mass percentage composition is 98%；
To methyl vinyl antifebrin：Weight/mass percentage composition is 98%；
The chloro- 2,5- dimethoxys acetyl-acetanilides (AS-IRG) of 4-：Weight/mass percentage composition is 98%；
Glycan molecule is coupled diketopyrrolo-pyrrole compound：Prepared by embodiment 1 or the methods described of embodiment 2, quality percentage Content is 98%；
Sulfamic acid：Weight/mass percentage composition is 98%；
Superfine rosin：Weight/mass percentage composition is 100%；
Newtrex：Weight/mass percentage composition is 100%；
【Embodiment 3】
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, stir it is lower add 3,3- dichloro-benzidine 8g and Dianisidine 0.5g, mix scattered 2.5 hours, on the rocks to be cooled to less than -5 DEG C, addition natrium nitrosum 17.7g, stirring 1 Hour, excessive natrium nitrosum is destroyed with sulfamic acid, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 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, adds caustic soda 11.4g, stirring, obtains even summation component lysate II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, by even summation component lysate II Control adds for 10 minutes, pH=6.4, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=4.1, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds AEO surfactant 3g, hyper-dispersant 17000 2g, pigment is surface-treated, is warming up to 80 DEG C, be incubated 150 minutes, add 3g pigment derivatives, stirred 10 minutes, cooling To less than 50 DEG C.Press filtration, washing.Filtration cakes torrefaction removes moisture, obtains 1# environmental protection UV ink PY13 pigment.
Rosin solution is prepared：500ml water is heated to 100 DEG C, adds superfine rosin 75g, stirring makes its complete in 60 minutes Dissolve transparent, be cooled to 50-55 DEG C, obtain rosin solution.
【Embodiment 4】
S1. diazo-reaction
200ml water and 18.4g hydrochloric acid are added in diazo-reaction container, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 3g, stirred It is transparent to mix dissolving, adds caustic soda 11.4g, stirring, obtains coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.7, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=4.3, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds aliphatic acid sulfoalkyl ester surfactant 5g, the 2g of hyper-dispersant 22000, Pigment is surface-treated, is warming up to 80 DEG C, is incubated 150 minutes, adds pigment derivative 3g, stirs 10 minutes, is cooled to Less than 50 DEG C.Press filtration, washing.Filtration cakes torrefaction removes moisture, obtains 2# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 3g, stirred It is transparent to mix dissolving, adds caustic soda 11.4g, stirring, adds aliphatic acid sulfoalkyl ester surfactant 5g, obtain coupling component solution Ⅱ；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.2, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=3.8, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds the 2g of hyper-dispersant 22000, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds pigment derivative 3g, stirs 10 minutes, is cooled to less than 50 DEG C.Press filtration, washing.Filtration cakes torrefaction Moisture is removed, obtains 3# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 5g, stirred It is transparent to mix dissolving, adds caustic soda 11.4g stirrings, adds AEO surfactant 5g, it is molten to obtain coupling component Liquid II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.4, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=3.9, adds 15% (mass percent concentration) rosin resin solution 25g, right Pigment carries out resinification processing, stirs 30 minutes, adds the 2g of hyper-dispersant 22000, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds pigment derivative 3g, stirs 10 minutes, is cooled to less than 50 DEG C.Press filtration, washing.Filter cake is done Dry removing moisture, obtain 4# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 5g, stirred It is transparent to mix dissolving, adds caustic soda 11.4g stirrings, obtains coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.6, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=4.3, adds 15% (mass percent concentration) rosin resin solution 25g, right Pigment carries out resinification processing, stirs 30 minutes, adds the 2g of hyper-dispersant 22000, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds pigment derivative 3g, stirs 10 minutes, is cooled to less than 50 DEG C.Press filtration, washing.Filter cake is done Dry removing moisture, obtain 5# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 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, adds caustic soda 11.4g stirrings, obtains coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.8, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, adds AEO 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. post-process
Yellow mill base stirs 1 hour, pH=3.8, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds the 2g of hyper-dispersant 22000, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds pigment derivative 3g, stirs 10 minutes, is cooled to less than 50 DEG C.Press filtration, washing.Filtration cakes torrefaction Moisture is removed, obtains 6# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 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, adds caustic soda 11.4g, stirring, obtains coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.6, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound, adds AEO 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. post-process
Yellow mill base stirs 1 hour, pH=4.2, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds the 2g of hyper-dispersant 22000, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds pigment derivative 3g, stirs 10 minutes, is cooled to less than 50 DEG C.Press filtration, washing.Filtration cakes torrefaction Moisture is removed, obtains 7# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule described in embodiment 1 is coupled diketopyrrolo-pyrrole compound 10g, stirring, caustic soda 11.4g is added, dissolving is transparent, obtains coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.5, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=3.8, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds 22000 hyper-dispersant 2g, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds pigment derivative 5g, stirs 10 minutes, is cooled to less than 50 DEG C.Press filtration, washing.Filtration cakes torrefaction Moisture is removed, obtains 8# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, and to methyl vinyl antifebrin 2g, glycan molecule coupling diketopyrrolo-pyrrole compound 6g described in embodiment 1 Stirring, the 11.4g dissolvings of addition caustic soda are transparent, obtain coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.4, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides antifebrin, to methyl vinyl acetyl The precipitate of aniline and glycan molecule coupling diketopyrrolo-pyrrole compound.Add AEO surfactant 4g 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. post-process
Yellow mill base stirs 1 hour, pH=4, adds 15% (mass percent concentration) rosin resin solution 25g to pigment Resinification processing is carried out, is stirred 30 minutes, 22000 hyper-dispersant 2g is added, pigment is surface-treated, is warming up to 80 DEG C, Insulation 150 minutes, add alkyl glyceryl ether sulfonate 2g, add pigment derivative 3g, stir 10 minutes, be cooled to 50 DEG C with Under.Press filtration, washing.Filtration cakes torrefaction removes moisture, obtains 9# environmental protection UV ink PY13 pigment.
The compound 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, stirs lower addition 3,3- dichloro-benzidine 8g, It is dispersed with stirring 2.5 hours, it is on the rocks to be cooled to less than -5 DEG C, natrium nitrosum 17.7g is added, stirs 1 hour, is destroyed with sulfamic acid Excessive natrium nitrosum, terminal is slightly blue to KI starch papers, obtains diazonium salt solution I；
S2. coupling reaction
Add 120ml water in coupling component dissolution vessel, be warming up to 30 DEG C, stir lower addition 2.4- dimethylacetamide acetyl Aniline 17.6g, glycan molecule coupling diketopyrrolo-pyrrole compound 6g described in methyl vinyl antifebrin 2g and embodiment 1 is stirred Mix, add caustic soda 11.4g, dissolving is transparent, obtains coupling component solution II；
100ml water, 5.3g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is controlled System adds for 10 minutes, pH=6.7, is warming up to 70 DEG C, generates white 2.4- dimethylacetamides 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. post-process
Yellow mill base stirs 1 hour, pH=4.1, adds 15% (mass percent concentration) rosin resin solution 25g to face Material carries out resinification processing, stirs 30 minutes, adds 2g hyper-dispersants 22000, pigment is surface-treated, is warming up to 80 DEG C, 150 minutes are incubated, adds 5g alkyl glyceryl ether sulfonates, adds pigment derivative 3g, stirs 10 minutes, is cooled to 50 DEG C Below.Press filtration, washing.Filtration cakes torrefaction removes moisture, obtains 10# environmental protection UV ink PY13 pigment.
The compound 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 to be cooled to less than -3 DEG C, natrium nitrosum 18g is added, nitrite is generated with hydrochloric acid reaction, then With 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 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, 20 DEG C of addition caustic soda 75g, adds AAA 50g, Glycan molecule described in embodiment 2 is coupled diketopyrrolo-pyrrole compound 6g, and dissolving is transparent.Coupling component solution II is obtained,
240ml water is added in container is coupled, acetic acid 23.7g stirrings, aqueous acetic acid is mixed into, by coupling component solution To 10 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl The precipitate of antifebrin and glycan molecule coupling diketopyrrolo-pyrrole compound.PH=5.4,25 DEG C of solution temperature, obtains idol 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. post-process
Yellow mill base stirs 1 hour, pH=4.2, adds nonionic surfactant aliphatic acid polyethenoxy ether 9g, stirring 20 minutes, 95 DEG C are warming up to, is incubated 120 minutes, adds pigment derivative 5g, stirs 10 minutes, is cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 1# environment-friendly ink PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 100g caustic soda are added in coupling component dissolution vessel, adds AAA 50g, embodiment 2 The glycan molecule is coupled diketopyrrolo-pyrrole compound 4g, and dissolving is transparent.Coupling component solution II is obtained,
200ml water is added in container is coupled, the stirring of 25.2g acetic acid, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stirs 1 hour, pH=3.4, adds nonionic surfactant APES 9g, stirring 20 minutes, 95 DEG C are warming up to, is incubated 120 minutes, adds pigment derivative 5g, stirs 10 minutes, is cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 2# environment-friendly ink PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water is added in coupling component dissolution vessel, 20 DEG C of addition caustic soda 100g, adds AAA 50g, Glycan molecule described in embodiment 2 is coupled diketopyrrolo-pyrrole compound 8g, and dissolving is transparent.Coupling component solution II is obtained,
200ml water is added in container is coupled, the stirring of 25.2g acetic acid, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stirs 1 hour, pH=4.3, adds nonionic surfactant AEO 9g, stirring 20 minutes, 95 DEG C are warming up to, is incubated 120 minutes, adds pigment derivative 5g, stirs 10 minutes, is cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 3# environment-friendly ink PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, adds AAA 50g, the institute of embodiment 1 Glycan molecule coupling diketopyrrolo-pyrrole compound 8g is stated, dissolving is transparent.Coupling component solution II is obtained,
200ml water, 25.2g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, coupling component solution II is adjusted To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes whole temperature, generates white acetoacetyl 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. post-process
Yellow mill base stirs 1 hour, pH=3.7, adds 15g nonionic surfactant AEO, Stirring 20 minutes, 95 DEG C are warming up to, are incubated 120 minutes, add pigment derivative 5g, stirred 10 minutes, be cooled to less than 70 DEG C. Press filtration, washing.Filter cake removes moisture by drying, and obtains 4# environment-friendly ink PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 100g caustic soda are added in coupling component dissolution vessel, adds AAA 50g, embodiment 1 The glycan molecule is coupled diketopyrrolo-pyrrole compound 8g, and dissolving is transparent.Coupling component solution II is obtained,
200ml water is added, acetic acid 25.2g stirrings, aqueous acetic acid is mixed into, coupling component solution II is adjusted into temperature extremely 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes, generates white AAA and sugar The precipitate of molecule coupling labeled diketopyrrolo-pyrrole compound.PH=4.6,25 DEG C of solution temperature, obtains Coupling Solution III,
Diazonium liquor I is added to generation yellow mill base in 25 DEG C of Coupling Solutions III with 100 minutes being coupled in container；
S3. post-process
Yellow mill base stirs 1 hour, pH=3.2, adds nonionic surfactant APES 15g, stirs Mix 20 minutes, be warming up to 95 DEG C, be incubated 120 minutes, add pigment derivative 10g, stir 10 minutes, be cooled to less than 70 DEG C. Press filtration, washing.Filter cake removes moisture by drying, and obtains 5# environment-friendly ink PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, adds AAA 50g, the institute of embodiment 1 Glycan molecule coupling diketopyrrolo-pyrrole compound 4g is stated, dissolving is transparent.Coupling component solution II is obtained,
200ml water is added in container is coupled, the stirring of 25.2g acetic acid, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stirs 1 hour, pH=3.9, adds nonionic surfactant aliphatic acid polyethenoxy ether 15g, stirs Mix 20 minutes, be warming up to 95 DEG C, be incubated 120 minutes, add pigment derivative 10g, stir 10 minutes, be cooled to less than 70 DEG C. Press filtration, washing.Filter cake removes moisture by drying, and obtains 6# environment-friendly ink PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, adds AAA 50g, the institute of embodiment 2 Glycan molecule coupling diketopyrrolo-pyrrole compound 8g is stated, dissolving is transparent.Coupling component solution II is obtained,
200ml water is added in container is coupled, the stirring of 25.2g acetic acid, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stirs 1 hour, pH=4.5, adds anion surfactant alkylbenzenesulfonate 10g, stirring 20 Minute, 95 DEG C are warming up to, is incubated 120 minutes, adds pigment derivative 15g, stirs 10 minutes, is cooled to less than 70 DEG C.Press filtration, Washing.Filter cake removes moisture by drying, and obtains 7# environment-friendly ink PY12 yellow pigments.
【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 less than -3 DEG C, natrium nitrosum 15g solution is added, nitrous is generated with hydrochloric acid reaction Hydrochlorate, then diazol 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 papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water is added in coupling component dissolution vessel, 20 DEG C of addition caustic soda 20g, adds AAA 50g, Glycan molecule described in embodiment 2 is coupled diketopyrrolo-pyrrole compound 8g, and dissolving is transparent.Coupling component solution II is obtained,
200ml water is added in container is coupled, 25.2g acetic acid, aqueous acetic acid is mixed into, coupling component solution II is adjusted To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes whole temperature, generates white acetoacetyl 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. post-process
Yellow mill base stirs 1 hour, pH=4.0, adds anion surfactant alkylsulfonate 4g and nonionic table Face activating agent APES 6g, stir 20 minutes, be warming up to 95 DEG C, be incubated 120 minutes, add pigment derivative 15g, stir 10 minutes, be cooled to less than 70 DEG C.Press filtration, washing.Filter cake removes moisture by drying, and obtains 8# environment-friendly inks use PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, Again with 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 0 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid. KI starch papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water, 20g caustic soda are added in coupling component dissolution vessel, adds AAA 50g, the institute of embodiment 2 Glycan molecule coupling diketopyrrolo-pyrrole compound 10g is stated, dissolving is transparent.Coupling component solution II is obtained,
200ml water, the stirring of 25.2g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stir 1 hour, pH=4.1, add anion surfactant aliphatic acid sulfoalkyl ester 4g and it is non-from Sub- surfactant aliphatic acid polyethenoxy ether 6g, stir 20 minutes, be warming up to 95 DEG C, be incubated 120 minutes, add pigment and derive Thing 5g, stir 10 minutes, be cooled to less than 70 DEG C.Press filtration, washing.Filter cake removes moisture by drying, and obtains 9# environment-friendly inks With PY12 yellow pigments.
【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 less than -3 DEG C, natrium nitrosum 15g solution is added, nitrous is generated with hydrochloric acid reaction Hydrochlorate, then diazol 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 papers are slightly blue.Obtain diazonium liquor I；
S2. coupling reaction
400ml water is added in coupling component dissolution vessel, 20 DEG C of addition caustic soda 20g, adds AAA 50g, Dissolve transparent.Coupling component solution II is obtained,
200ml water, the stirring of 25.2g acetic acid are added in container is coupled, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stir 1 hour, pH=3.8, add anion surfactant aliphatic acid sulfoalkyl ester 5g and it is non-from Sub- surfactant aliphatic acid polyethenoxy ether 5g, stir 20 minutes, be warming up to 95 DEG C, be incubated 120 minutes, add pigment and derive Thing 5g, stir 10 minutes, be cooled to less than 70 DEG C.Press filtration, washing.Filter cake removes moisture by drying, and obtains 10# environment-friendly inks With PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, natrium nitrosum 15g is added, nitrite is generated with hydrochloric acid reaction, then With 3,3- dichloro-benzidine and dianisidine reaction generation diazol, 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, adds AAA 50g, dissolving is saturating It is bright, coupling component solution II is obtained,
200ml water is added in container is coupled, the stirring of 25.2g acetic acid, aqueous acetic acid is mixed into, by coupling component solution To 14 DEG C, control adds mixing aqueous acetic acid in coupling component solution II in 10 minutes II adjustment temperature, generates white acetyl 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. post-process
Yellow mill base stir 1 hour, pH=4.6, add anion surfactant aliphatic acid sulfoalkyl ester 6g and it is non-from Sub- surfactant aliphatic acid polyethenoxy ether 4g, stir 20 minutes, be warming up to 95 DEG C, be incubated 120 minutes, add pigment and derive Thing 5g, stir 10 minutes, be cooled to less than 70 DEG C.Press filtration, washing.Filter cake removes moisture by drying, and obtains 11# environment-friendly inks With PY12 yellow pigments.
【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 to be cooled to less than -3 DEG C, add natrium nitrosum 8.7g, nitrite generated with hydrochloric acid reaction, then with 3,3- dichloros Benzidine reaction generates diazol, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain Diazonium liquor I；
S2. coupling reaction
100ml water, 30 DEG C of addition chloro- 2,5- dimethoxys of 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 dissolving is saturating It is bright.Obtain coupling component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control 30-40 minutes are added in mixing aqueous acetic acid II adjustment temperature, generate chloro- 2, the 5- dimethoxies of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Add aliphatic acid sulphur Arrcostab 3g and APES 2g compositional liquors, stir 15 minutes.PH=5.6,20 DEG C of solution temperature, obtain being coupled molten 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 5.2g, it is transparent that stirring is completely dissolved it in 60 minutes, by pine Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.2, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant sulphosuccinates 1g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 1# environment-friendly ink PY83 yellow pigments.
【Embodiment 25】
S1. diazo-reaction
Add 100ml water and 6.6g hydrochloric acid in diazo-reaction container, 3.3- dichloro-benzidine 15g, described in embodiment 1 Glycan molecule coupling diketopyrrolo-pyrrole compound 6g stirrings, disperse 2.5 hours.It is on the rocks to be cooled to less than -3 DEG C, add nitrous Sour sodium 8.7g, nitrite is generated with hydrochloric acid reaction, then generation diazol, 10-15 DEG C of stirring 1 are reacted with 3,3- dichloro-benzidine Hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain diazonium liquor I；
S2. coupling reaction
100ml water is added in coupling component dissolution vessel, adds caustic soda 26.5g, adds chloro- 2, the 5- dimethoxys of 4- Acetyl-acetanilide (AS-IRG) 40g, dissolving are transparent.Obtain coupling component solution II；
120ml water is added in container is coupled, 80% acetic acid 11.5g stirrings, is mixed into aqueous acetic acid.Group will be coupled Solution II is divided to adjust temperature to 30 DEG C, control 30-40 minutes are added in mixing aqueous acetic acid, generate white 4- chloro- 2,5- The precipitate of dimethoxy acetyl-acetanilide (AS-IRG).Add alkylbenzenesulfonate 2g and AEO 1g Compositional liquor, stir 15 minutes.PH=5.9,20 DEG C of solution temperature, 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 5.2g, it is transparent that stirring is completely dissolved it in 60 minutes, by pine Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.3, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant fatty acid sulfoalkyl ester 1g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 2# environment-friendly ink PY83 yellow pigments.
【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 to be cooled to less than -3 DEG C, add natrium nitrosum 8.7g, nitrite generated with hydrochloric acid reaction, then with 3,3- dichloros Benzidine reaction generates diazol, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain Diazonium liquor I；
S2. coupling reaction
100ml water, 30 DEG C of addition chloro- 2,5- dimethoxys second of caustic soda 26.5g, 4- are added in coupling component dissolution vessel Acyl group antifebrin (AS-IRG) 40g, dissolving are transparent.Obtain coupling component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control 30-40 minutes are added in mixing aqueous acetic acid II adjustment temperature, generate chloro- 2, the 5- dimethoxies of white 4- The precipitate of base acetyl-acetanilide (AS-IRG).Aliphatic acid sulfoalkyl ester 2g and APES 3g is added to compound Liquid, stir 15 minutes.Add glycan molecule coupling diketopyrrolo-pyrrole compound 6g, pH=5.7, solution temperature described in embodiment 1 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 5.2g, it is transparent that stirring is completely dissolved it in 60 minutes, by pine Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.0, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant alkylnaphthalene sulfonate 1g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 3# environment-friendly ink PY83 yellow pigments.
【Embodiment 27】
S1. diazo-reaction
100ml water and 6.6g hydrochloric acid are added in diazo-reaction container, 3.3- dichloro-benzidine 15g, is dispersed with stirring 2.5 Hour.It is on the rocks to be cooled to less than -3 DEG C, add natrium nitrosum 8.7g, nitrite generated with hydrochloric acid reaction, then with 3,3- dichloros Benzidine reaction generates diazol, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain Diazonium liquor I；
S2. coupling reaction
100ml water is added in coupling component dissolution vessel, 26.5g caustic soda, adds chloro- 2, the 5- dimethoxys acetyl group of 4- Glycan molecule described in antifebrin (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 6g, and dissolving is transparent.Obtain Coupling component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control 30-40 minutes are added in mixing aqueous acetic acid II adjustment temperature, generate chloro- 2, the 5- dimethoxies of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Add benzene sulfonamide Hydrochlorate 2g and AEO 1g compositional liquors, are stirred 15 minutes.PH=5.5,20 DEG C of solution temperature, 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. post-process,
100ml water is heated to 100 DEG C, adds newtrex 5.2g, it is transparent that stirring is completely dissolved it in 60 minutes, by pine Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.5, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant alkyl glyceryl ether sulfonate 1g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C. Press filtration, washing.Filter cake removes moisture by drying, and obtains 4# environment-friendly ink PY83 yellow pigments.
【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 to be cooled to less than -3 DEG C, add natrium nitrosum 8.7g, nitrite generated with hydrochloric acid reaction, then with 3,3- dichloros Benzidine reaction generates diazol, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain Diazonium liquor I；
S2. coupling reaction
100ml water, 22g caustic soda, the chloro- 2,5- dimethoxys 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 dissolving is transparent, is coupled Component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control 30-40 minutes are added in mixing aqueous acetic acid II adjustment temperature, generate chloro- 2, the 5- dimethoxies of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Add anion table Face activating agent aliphatic acid sulfoalkyl ester 4g, stir 15 minutes.PH=5.8,20 DEG C of solution temperature, 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 10g, it is transparent that stirring is completely dissolved it in 60 minutes, by pine Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.4, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant fatty acid sulfoalkyl ester 1g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 5# environment-friendly ink PY83 yellow pigments.
【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 to be cooled to less than -3 DEG C, add natrium nitrosum 8.7g, nitrite generated with hydrochloric acid reaction, then with 3,3- dichloros Benzidine reaction generates diazol, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain Diazonium liquor I；
S2. coupling reaction
The 100ml chloro- 2,5- dimethoxys acetyl group second of water, 26.5g caustic soda, 4- is added in coupling component dissolution vessel Glycan molecule described in anilide (AS-IRG) 40g, embodiment 1 is coupled diketopyrrolo-pyrrole compound 10g, and dissolving is transparent.Obtain Coupling component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.By coupling component solution To 30 DEG C, control 30-40 minutes are added in mixing aqueous acetic acid II adjustment temperature, generate chloro- 2, the 5- dimethoxies of white 4- The precipitate of base acetyl-acetanilide (AS-IRG) and glycan molecule coupling diketopyrrolo-pyrrole compound.Stirring 15 minutes. PH=5.7,20 DEG C of solution temperature, 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 10g, it is transparent that stirring is completely dissolved it in 60 minutes, adds Alkylbenzenesulfonate 5g and AEO 2g, stirring is transparent, and rosin solution is cooled into 50-55 DEG C.It is polymerize Rosin solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.5, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant alkylbenzenesulfonate 3g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 6# environment-friendly ink PY83 yellow pigments.
【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 less than -3 DEG C, natrium nitrosum 8.7g solution is added, nitrite is generated with hydrochloric acid reaction, then with 3,3- Dichloro-benzidine reaction generation diazol, 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers. Obtain diazonium liquor I；
S2. coupling reaction
100ml water, 26.5g caustic soda, the chloro- 2,5- dimethoxys acetoacetos of 4- are added in coupling component dissolution vessel The 8g dissolvings of glycan molecule coupling diketopyrrolo-pyrrole compound are transparent described in aniline (AS-IRG) 40g, embodiment 1.It is coupled Component solution II；
120ml water, the stirring of 11.5g acetic acid are added in container is coupled, is mixed into aqueous acetic acid.Add anionic surface Activating agent sulphosuccinates 5g, coupling component solution II is adjusted into temperature to 30 DEG C, control 30-40 minutes are added to mixing In aqueous acetic acid, chloro- 2, the 5- dimethoxys acetyl-acetanilides (AS-IRG) of white 4- and glycan molecule coupling diketone are generated The precipitate of pyrrolopyrrole compound.Stirring 15 minutes.PH=5.9,20 DEG C of solution temperature, 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 10g, it is transparent that stirring is completely dissolved it in 60 minutes, by pine Fragrant solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.3, adds newtrex solution IV, stirs 20 minutes, adds anion Surfactant sulphosuccinates 3g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Pressure Filter, washing.Filter cake removes moisture by drying, and obtains 7# environment-friendly ink PY83 yellow pigments.
【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 less than -3 DEG C, natrium nitrosum 8.7g solution is added, nitrite is generated with hydrochloric acid reaction, then with 3,3- Dichloro-benzidine reaction generation diazol, 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers. Obtain diazonium liquor I；
S2. coupling reaction
100ml water, 26.5g caustic soda, the chloro- 2,5- dimethoxys acetoacetos 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 dissolving is transparent, is coupled Component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.Add alkyl glycerylether Sulfonate 5g and APES 4g, coupling component solution II is adjusted into temperature to 30 DEG C, control 30-40 minutes add Into mixing aqueous acetic acid, generate chloro- 2, the 5- dimethoxys acetyl-acetanilides (AS-IRG) of white 4- and glycan molecule is even The precipitate of Determination of Vicinal Diketones pyrrolopyrrole compound.Stirring 15 minutes.PH=5.8,20 DEG C of solution temperature, 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 8g, it is transparent that stirring is completely dissolved it in 60 minutes, by rosin Solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.4, adds newtrex solution IV, stirs 20 minutes, adds alkyl phenol APEO 3g, stir 10 minutes, be warming up to 90 DEG C, be incubated 20 minutes, be cooled to less than 70 DEG C.Press filtration, washing.Filter cake passes through Cross to dry and remove moisture, obtain 8# environment-friendly ink PY83 yellow pigments.
【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 to be cooled to less than -3 DEG C, add natrium nitrosum 8.7g, nitrite generated with hydrochloric acid reaction, then with 3,3- dichloros Benzidine reaction generates diazol, and 10-15 DEG C is stirred 1 hour.Terminal is transferred to sulfamic acid.The micro- indigo plant of KI starch papers.Obtain Diazonium liquor I；
S2. coupling reaction
100ml water, 26.5g caustic soda, the chloro- 2,5- dimethoxys acetoacetos 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 dissolving is transparent, is coupled Component solution II；
120ml water is added in container is coupled, the stirring of 11.5g acetic acid, is mixed into aqueous acetic acid.Add alkyl benzene sulphonate Salt 5g and AEO 4g, coupling component solution II is adjusted into temperature to 30 DEG C, control 30-40 minutes are added to mixed Close in aqueous acetic acid, generate chloro- 2, the 5- dimethoxys acetyl-acetanilides (AS-IRG) of white 4- and glycan molecule coupling two The precipitate of ketone pyrrolopyrrole compound sum.Stirring 15 minutes.PH=5.6,20 DEG C of solution temperature, 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. post-process
100ml water is heated to 100 DEG C, adds newtrex 8g, it is transparent that stirring is completely dissolved it in 60 minutes, by rosin Solution is cooled to 50-55 DEG C, obtains newtrex solution IV；
Orange-yellow mill base stirs 1 hour, pH=4.2, adds AEO 3g, adds newtrex solution IV, stir 20 minutes, stir 10 minutes, control is warming up to 90 DEG C for 60 minutes, is incubated 20 minutes, is cooled to less than 70 DEG C.Press filtration, Washing.Filter cake removes moisture by drying, and obtains 9# environment-friendly ink PY83 yellow pigments.
【Experimental example】
Detected using embodiment 3 to the gained yellow pigment of embodiment 32 as sample, each data are shown in Table one, table two, table three.
Table one：PY13 yellow pigment experimental results
Table two：PY12 yellow pigment experimental results
Table three：PY83 yellow pigment experimental results

Claims (10)

1. application of the glycan molecule coupling diketopyrrolo-pyrrole compound that formula (I) represents in yellow pigment preparation：
Wherein, R1For H, Br, Cl, F, CN, C1-8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, C1-8Straight or branched Alkoxy, C1-8Monosubstituted or disubstituted amino；
A is monosaccharide groups, disaccharide base or three glycosyls：
Monose 1- positions are substituted by α or β or both mixture；
The 1- positions of disaccharide or 6- positions carbon atom are coupled with the nitrogen-atoms in formula (I)；
The 6- positions carbon atom of trisaccharide is coupled with the nitrogen-atoms in formula (I)；
B be H or with A identicals monosaccharide groups, disaccharide base or three glycosyls.
2. yellow pigment, it is characterised in that comprise the following steps in its preparation process：
S1. diazo-reaction
Under stirring by 3,3- dichloro-benzidine add hydrochloric acid solution in, disperse certain time after, under low temperature with sodium nitrite solution Diazo-reaction is carried out, the natrium nitrosum for removing surplus obtains diazo solution I；
S2. coupling reaction
S21. antifebrin compound and glycan molecule coupling diketopyrrolo-pyrrole compound are dissolved in alkaline solution, obtain idol Close component solution II；
S22. coupling component solution II is added in aqueous acetic acid, generates antifebrin compound and glycan molecule coupling diketone pyrrole Cough up and azole compounds precipitate, pH are adjusted to 4.5~6.5, temperature adjustment obtains Coupling Solution III to 18-70 DEG C；
S23. diazo solution I obtained by step S1 is added in Coupling Solution III, obtains yellow mill base；
S3. post-process
Yellow mill base is post-treated to obtain yellow pigment,
Glycan molecule coupling diketopyrrolo-pyrrole compound is described in step S2：
Wherein, R1For H, Br, Cl, F, CN, C1-8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, C1-8Straight or branched Alkoxy, C1-8Monosubstituted or disubstituted amino；
A is monosaccharide groups, disaccharide base or three glycosyls：
Monose 1- positions are substituted by α or β or both mixture；
The 1- positions of disaccharide or 6- positions carbon atom are coupled with the nitrogen-atoms in formula (I)；
The 6- positions carbon atom of trisaccharide is coupled with the nitrogen-atoms in formula (I)；
B be H or with A identicals monosaccharide groups, 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 with hydrochloric acid solution Amine.
4. the yellow pigment according to Claims 2 or 3, it is characterised in that：The weight proportion of each raw material is in step S1：
5. yellow pigment according to claim 4, it is characterised in that the weight proportion of each raw material is in step S2：
6. the yellow pigment according to Claims 2 or 3, it is characterised in that：Antifebrin compound described in step S21 is 2.4- bis- Methyl vinyl antifebrin and the mixture to methyl vinyl antifebrin, either AAA or chloro- 2, the 5- bis- of 4- Methoxyacetyl antifebrin, either adjacent methyl vinyl antifebrin or to methoxyl group AAA, or to chlorine AAA, or adjacent carboxyl AAA.
7. the yellow pigment according to Claims 2 or 3, it is characterised in that step S22 includes：Anion is added into reaction system The compositional liquor of surfactant and nonionic surfactant carries out surface modification treatment, anion surfactant and nonionic The weight ratio preferably 2 of surfactant:(1-4).
8. the yellow pigment according to Claims 2 or 3, it is characterised in that in step S23, with 50~200min by obtained by step S1 Diazo solution I is at the uniform velocity added in Coupling Solution III.
9. the yellow pigment according to Claims 2 or 3, it is characterised in that step S3 includes：
Surfactant and/or hyper-dispersant are added into yellow mill base surface modification is carried out to pigment；
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.
10. the preparation method of yellow pigment, it is characterised in that comprise the following steps：
S1. diazo-reaction
Under stirring by 3,3- dichloro-benzidine add hydrochloric acid solution in, disperse certain time after, under low temperature with sodium nitrite solution Diazo-reaction is carried out, the natrium nitrosum for removing surplus obtains diazo solution I；
S2. coupling reaction
S21. antifebrin compound and glycan molecule coupling diketopyrrolo-pyrrole compound are dissolved in alkaline solution, obtain idol Close component solution II；
S22. coupling component solution II is added in aqueous acetic acid, generates antifebrin compound and glycan molecule coupling diketone pyrrole Simultaneously azole compounds precipitate is coughed up, adjusts to proper pH value and temperature, obtains Coupling Solution III；
S23. diazo solution I obtained by step S1 is added in Coupling Solution III, obtains yellow mill base；
S3. post-process
Yellow mill base is post-treated to obtain yellow pigment,
Glycan molecule coupling diketopyrrolo-pyrrole compound is described in step S2：
Wherein, R1For H, Br, Cl, F, CN, C1-8Straight or branched alkyl, substitution or unsubstituted aromatic alkyl, C1-8Straight or branched Alkoxy, C1-8Monosubstituted or disubstituted amino；
A is monosaccharide groups, disaccharide base or three glycosyls：
Monose 1- positions are substituted by α or β or both mixture；
The 1- positions of disaccharide or 6- positions carbon atom are coupled with the nitrogen-atoms in formula (I)；
The 6- positions carbon atom of trisaccharide is coupled with the nitrogen-atoms in formula (I)；
B be H or with A identicals monosaccharide groups, disaccharide base or three glycosyls.
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