CN101948632A - Yellow pigment for color liquid crystal filter and preparation method thereof - Google Patents
Yellow pigment for color liquid crystal filter and preparation method thereof Download PDFInfo
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- CN101948632A CN101948632A CN2010102555849A CN201010255584A CN101948632A CN 101948632 A CN101948632 A CN 101948632A CN 2010102555849 A CN2010102555849 A CN 2010102555849A CN 201010255584 A CN201010255584 A CN 201010255584A CN 101948632 A CN101948632 A CN 101948632A
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Abstract
The invention relates to a yellow pigment for a color liquid crystal filter, which consists of at least two compounds. The compounds include a compound I and a compound II. A preparation method for the pigment comprises the following procedures of: A, synthesizing a yellow pigment crude product of which the structural formula is the compound I by 2-methyl-8-aminoquinoline and tetrachlorophthalic anhydride serving as basic raw materials; and B, performing pigment processing on the yellow pigment crude product. The pigment processing procedure comprises the following steps of: 1, pre-grinding the yellow pigment crude product; and 2, performing pigment postprocessing on the pre-ground yellow pigment crude product. The yellow pigment prepared by the method has high transparency, brightness and contrast, and has good fluidity in a liquid dispersoid for coloring the color filter.
Description
Technical field
The present invention relates to the pigment technology field of colour filter, relate in particular to a kind of yellow ultramarine that is used for the color liquid crystal colour filter and preparation method thereof.
Background technology
Along with the development of lcd technology, the employed pigment demand of color filter significantly improves.The used pigment of colour filter is having higher requirement qualitatively, not only requires pigment that high fast light and thermotolerance is arranged, and requires pigment to have high transparent, high-contrast, high briliancy.The colorant dispersion of making of pigment has good flowability and stability in storage, guarantees that the coating processing of colour filter film is smooth, to obtain high-quality colour filter film.The pigment that conventional working method is produced is difficult to the specification of quality that reaches above-mentioned.
A kind of pigment of the prior art, the call number of its pigment are C.I.Pigment Yellow 138 (being abbreviated as P.Y.138), and its structural formula is following Compound I,
Have very high fast light weathering resistance, and good thermostability.Most of type of merchandises have low specific surface area, greatly about 20-30m
2Therefore/g has good opacifying power, is mainly used in paint field.Though the pigment of high-specific surface area type is compared with covering type pigment at present, and is more transparent, look Li Genggao, coloured light is greener, and this pigment is in aspects such as the transparency, contrast gradient, flowability, the requirement that does not still reach the liquid crystal colour filter.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art or defective, a kind of yellow ultramarine that is used for the color liquid crystal colour filter is provided.
The present invention also aims to, a kind of yellow ultramarine preparation method who is used for the color liquid crystal colour filter is provided.
Compare with similar yellow ultramarine of the prior art, the yellow ultramarine of preparing according to the inventive method has the high transparency, briliancy and contrast gradient, and has good flowability in the aqueous dispersion painted for colour filter.
To achieve these goals, the present invention has adopted following technical scheme:
A kind of yellow ultramarine that is used for the color liquid crystal colour filter, it is constituted by two or more at least compounds; It is characterized in that,
Described compound comprises the following Compound I of structural formula:
The Compound I I that also comprises following structural formula:
Wherein,
Y representative-SO3X ,-SO2X ,-CH2-Z, n is the integer of 1-4;
X is the alkyl amine compound that contains 4 to 24 carbon atoms, or quarternary ammonium salt compound;
Z is the compound III of following structural formula:
Or alkyl amine compound, or quaternary ammonium salt;
Wherein, R represents the aliphatic hydrocarbon of 1-22 carbon atom, and m is the integer of 0-4.
A kind of preparation method who is used for the yellow ultramarine of color liquid crystal colour filter is characterized in that, mainly comprises following operation:
A, be basic raw material with 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride, the composite structure formula is the yellow ultramarine crude product of Compound I;
The pigmenting processing of B, yellow ultramarine crude product.
The preparation method of the above-mentioned yellow ultramarine that is used for the color liquid crystal colour filter, wherein,
The synthetic method of described yellow ultramarine crude product is roughly as follows:
A. be in the inert high boiling solvent at trichlorobenzene or other, add 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride, Zinc Chloride Anhydrous;
B. heat to boiling state, keep boiling number hour;
C. add dimethyl formamide, about 1 hour of stirring and refluxing;
D. filtered while hot then, and wash with dimethyl formamide;
E. use washing with alcohol at last, filter cake is through being drying to obtain the yellow ultramarine crude product that structural formula is a Compound I.
Described pigmenting manufacturing procedure comprises step:
One, the pre-grinding of yellow ultramarine crude product;
Two, the yellow ultramarine crude product after will grinding in advance carries out the pigmenting aftertreatment.
The pre-grinding of described yellow ultramarine crude product may further comprise the steps:
A, the yellow ultramarine crude product of described Compound I is put into grinding plant grind; The add-on of crude pigment product suitably adds according to the volume of grinding plant, can be 5～30kg/100L;
Add in B, the grinding plant and account for a certain proportion of grinding medium of volume of equipment; Simultaneously, the inorganic salts grinding aid that all right an amount of adding can be water-soluble, the add-on of grinding aid is 5～50% of a pigment weight;
The derivative of C, the described yellow ultramarine of adding is described Compound I I.
Described Compound I I can add before grinding, and ground with crude pigment product, also can add in the pigmenting post-processing stages, or the aftertreatment end, before filtering, add; The add-on of Compound I I is 0.5%～30% of a pigment weight.
Described pigmenting aftertreatment can be adopted solvent treatment method or mediate facture.
Described solvent treatment method is with the yellow ultramarine crude product through above-mentioned grinding, puts into a container that contains organic solvent and heat-treats;
In the solvent method treating processes, or before or after, can add Compound I I in right amount.
Described organic solvent can be the aliphatic alcohols, the arene that contain 1～8 carbon atom, have the substituent arene of halogen atom, and the compound of ketone, ethers, ester class.
Described kneading facture is in a Z type oar kneader, drops into the yellow ultramarine crude product after described process is ground in advance, and adds pulverizing inorganic salt grinding aid and organic solvent; Mediate temperature and be controlled at normal temperature to 130 ℃, the kneading time was controlled at 3～20 hours;
In the method for kneading treating processes, or before or after, can add Compound I I in right amount.
After mediating the processing end, will expect that group pulls an oar in water, filter then that pigment is separated with other water-soluble impurities, and drying and crushing promptly obtains yellow ultramarine dry powder.
Owing to adopted above-mentioned technical scheme, the present invention compared with prior art has following advantage and positively effect:
Because crude pigment product of the present invention is to be that basic raw material carries out synthetic with 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride, yellow ultramarine crude product after synthetic carries out pigmenting processing again, the yellow ultramarine crude product has given this pigment good tinctorial property after carrying out pigmenting processing.The pigment that processing obtains through pigmenting has meticulous regular particle, particle distribution is even, the colour development material that can satisfy LCD color filter is painted, has high gray scale, high-clarity, high-contrast, and its painted prepared product has good flowability and stable.
Description of drawings
By following examples and in conjunction with the description of its accompanying drawing, can further understand purpose, specific structural features and the advantage of its invention.In the accompanying drawing,
Fig. 1 is the preparation method's of the present invention's yellow ultramarine of being used for the color liquid crystal colour filter the process flow diagram of an embodiment (kneading method);
Fig. 2 is the preparation method's of the present invention's yellow ultramarine of being used for the color liquid crystal colour filter the process flow diagram of another embodiment (solvent method).
Embodiment
A kind of yellow ultramarine that is used for the color liquid crystal colour filter, it is constituted by two or more at least compounds; This compound comprises the following Compound I of structural formula:
The Compound I I that also comprises following structural formula:
Wherein,
Y representative-SO3X ,-SO2X ,-CH2-Z, n is the integer of 1-4;
X is the alkyl amine compound that contains 4 to 24 carbon atoms, or quarternary ammonium salt compound;
Z is the compound III of following structural formula:
Or alkyl amine compound, or quaternary ammonium salt;
Wherein, R represents the aliphatic hydrocarbon of 1-22 carbon atom, and m is the integer of 0-4.
Referring to Fig. 1, Fig. 2:
The preparation method of the yellow ultramarine that is used for the color liquid crystal colour filter that the present invention relates to mainly comprises following operation:
A, be that basic raw material composite structure formula is the yellow ultramarine crude product of Compound I with 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride;
The pigmenting processing of B, yellow ultramarine crude product.
The synthetic method of yellow ultramarine crude product is roughly as follows:
A. be in the inert high boiling solvent at trichlorobenzene or other, add 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride, Zinc Chloride Anhydrous;
B. heat to boiling state, keep boiling number hour;
C. add dimethyl formamide, about 1 hour of stirring and refluxing;
D. filtered while hot then, and wash with dimethyl formamide;
E. use washing with alcohol at last, filter cake is through being drying to obtain the yellow ultramarine crude product that structural formula is a Compound I.
Crude pigment product after synthetic does not also have the performance of using as pigment, does not have use value, must carry out pigmenting processing, gives pigment good tinctorial property.The pigment that processing obtains through pigmenting has meticulous regular particle, particle distribution is even, the colour development material that can satisfy LCD color filter is painted, has high gray scale, high-clarity, high-contrast, and its painted prepared product has good flowability and stable.
The pigmenting manufacturing procedure of the crude pigment product that the present invention relates to comprises:
One, the pre-grinding of yellow ultramarine crude product;
Two, the yellow ultramarine crude product after will grinding in advance carries out the pigmenting aftertreatment.
The pre-grinding of yellow ultramarine crude product may further comprise the steps:
A, the yellow ultramarine crude product of described Compound I is put into grinding plant grind; The grinding plant that is adopted can be horizontal ball mill, vibromill, agitated ball mill, and wherein horizontal ball mill can adopt relatively large equipment, and working ability can be very big, and vibromill can be realized continuous operation.The add-on of crude pigment product suitably adds according to the volume of grinding plant, can be 5～30kg/100L; Be preferably in 10～15kg/L.
Add in B, the grinding plant and account for a certain proportion of grinding medium of volume of equipment.Grinding medium is determined optimum addition according to mill efficiency.Grinding medium can be steel ball, also can be inorganic abrasive material, as zirconium oxide bead, alumina bead etc.Preferably adopt steel ball, hardness is lower than the grinding plant inner-wall material, can reduce the wearing and tearing of equipment like this.The consumption of steel ball accounts for shredder volumetrical 30～80%, does not have strict restriction.In order to increase grinding effect and other purposes, can add grinding aid.The general employing of grinding aid can be water-soluble inorganic salts, for example sodium-chlor, sodium sulfate, Calcium Chloride Powder Anhydrous etc.The add-on of grinding aid is 5～50% of a pigment weight, is preferably in 20～40%, adjusts according to grinding the result who will reach, for example the crystal habit of the fineness of pigment particles, pigment etc.
C, adding yellow ultramarine derivative are described Compound I I.
Compound I I can add before grinding, and ground with crude pigment product, also can add in the post-processing stages in second step, or the aftertreatment end, before filtering, add.The add-on of Compound I I is 0.5%～30% of a pigment weight, is preferably in 1%～10%.
The pigmenting aftertreatment that the present invention relates to can be adopted solvent treatment method or mediate facture.
The solvent treatment pigmentation method will be heat-treated in an organic solvent through the pigment of above-mentioned grinding.The organic solvent that is adopted can be water-soluble, also can be water insoluble.After handling pigment, can organic solvent be reclaimed by methods such as distillations, circulation is used for the pigment processing of next batch then.Organic solvent can be the aliphatic alcohols, the arene that contain 1～8 carbon atom, have the substituent arene of halogen atom, and ketone, ethers, esters solvent.These solvents can use separately, also can be their mixtures, can also mix use with water.These solvents are liquid at the normal temperature state, and boiling point is convenient to reclaim generally below 200 ℃.
Before solvent treatment, carry out acid treatment, the impurity of bringing into when grinding to remove is adjusted the pH value then to neutrality.Add organic solvent in slip, be warmed up to certain temperature in the stirring, can seal pressurization if desired, handle certain hour, organic solvent is reclaimed in air distillation or employing vacuum distilling then.The water-based paste mixture of pigment water-washes away impurity through filtering, and obtains dry product through different modes such as drying then, can obtain pigment powder through various grinding modes.Compound I I can add among solvent treatment, also can add before this or afterwards.
Mediating facture, is in a Z type oar kneader, drops into the described ground pigment crude product of first step, generally needs to add pulverizing inorganic grinding aid, as sodium-chlor, sodium sulfate etc.Also need to add solvent, be used for adjusting the thickness state of abrasive, to obtain best grinding effect.Employed solvent is generally not volatile liquid, and certain viscosity be arranged.In order to be convenient to separate with pigment, employed solvent generally can be water-soluble.Employed solvent is mainly the polymkeric substance of alcohols, alcohols, for example glycol ether, polyoxyethylene glycol.Above pigment composition grinds in kneader, and temperature is controlled at certain limit, generally at normal temperature to 130 ℃.Mediate certain hour, general 3～20 hours, be everlasting most 5～10 hours.Mediate and finish, will expect that group pulls an oar in water, filter then, pigment is separated with other water-soluble impurities, drying and crushing obtains pigment dry powder.
The pigment filter cake that above pigmenting aftertreatment obtains can be used multiple drying mode, and for example spraying, fluidized drying, expansion drying etc. directly obtain pigment dry powder.Also can use stove-drying, be crushed into powder then.
The bigger coacervate of crude pigment product, size of particles be more than tens microns, even to the hundreds of micron.In the pre-grinding process of the first step, this coacervate is opened, and forms tens nanometers, even littler particle, and the crystal habit of particle changes.The energy of input improves the surface energy of particle greatly, and this very high surface energy makes these meticulous particles condense again, but coacervate difference is originally followed in this cohesion.In solvent treatment or in mediating, pre-pigment agglomerate of grinding is opened, and pigment particles obtains certain homogenizing grows up, and crystal habit obtains adjusting, and the particle appearance is more regular.The pigment derivative that adds not only can play an effective role in the control to this adjustment, makes the particle of pigment more stable, and can play the effect of surface modification, the flowing property of pigment in application system is improved and stablizes.
X group in the Y group among the Compound I I can be introduced in the course of processing, also can before or after introduce.
Embodiment 1
Synthesizing of Compound I
In a reactor, add 3000 parts of trichlorobenzene, slowly drop into 158 parts of 2-methyl-8-quinolylamines, 600 parts of tetrachlorophthalic anhydrides, 50 parts of zinc chloride in the stirring.Be warmed up to boiling temperature, the water that reaction produces is got rid of reactor by condenser, is back to reactor after the trichlorobenzene condensation.Keep boiling state reaction 4 hours, add dimethyl formamide DMF600 part and reduce reflux temperature to 175 ℃, then 150～175 ℃ of filtrations, continue with 1500 parts of dimethyl formamide DMF washings, use 500 parts of washing with alcohol at last, the filter cake oven dry, obtaining the xanchromatic crude pigment product is Compound I.
The pigmenting of crude pigment product is handled
A) pigment grinds in advance
In one 10 side's ball mill, add the steel ball that accounts for volume 75%, the yellow ultramarine crude product of 1000 kilograms of examples 1,400 kilograms of sodium sulfate.Start shredder and ground 20 hours, controlled temperature is at 60～80 ℃ in the grinding.
B) in a kneader, drop into 100 parts a) in abrasive mixture, 350 parts of sodium sulfate, 70 parts of polyoxyethylene glycol PEG, start kneader and grind, 80～100 ℃ of controlled temperature ground 8 hours.In kneading process, determine whether to add polyoxyethylene glycol PEG according to state, to obtain best grinding effect.The following compound V of structural formula that adds one of 5 parts of Compound I I:
Continue to mediate half an hour.
After mediating end, will expect that group takes out, and pulls an oar with 4000 kg of water, add 50 parts in sulfuric acid, stir and be warmed up to 80 ℃, add 2.5 kilograms of Dodecyl trimethyl ammonium chloride, insulated and stirred 2 hours is filtered to wash and is removed whole salinities, and spraying drying obtains yellow ultramarine dry powder of the present invention.
Embodiment 2
Synthesizing of Compound I
In a reactor, add 3000 parts of trichlorobenzene, slowly drop into 158 parts of 2-methyl-8-quinolylamines, 800 parts of tetrachlorophthalic anhydrides, 60 parts of zinc chloride in the stirring.Be warmed up to boiling temperature, the water that reaction produces is got rid of reactor by condenser, is back to reactor after the trichlorobenzene condensation.Keep boiling state reaction 5 hours.Filter,, use 500 parts of washing with alcohol at last with 2000 parts of 160 ℃ of dimethyl formamide DMF washings, the filter cake oven dry, obtaining the xanchromatic crude pigment product is Compound I.
The pigmenting of crude pigment product is handled
A) pigment grinds in advance
In one 10 cubic metres ball mill, add the steel ball that accounts for volume 75%, the yellow ultramarine crude product of 1500 kilograms of examples 1,500 kilograms of sodium sulfate.Start shredder and ground 40 hours, controlled temperature is at 90～110 ℃ in the grinding.
B) solvent aftertreatment
In one 20 side's autoclave, add dimethylbenzene 10 sides, the mixture input with the grinding in a) stirs the compound IV of the following structural formula of adding 120 kg:
Heat to 150 ℃, be incubated 5 hours, cooling then, dimethylbenzene is reclaimed in vacuum distilling, and moisturizing keeps pulpous state.The filtered water flush away falls salinity, and spraying drying obtains yellow ultramarine dry powder of the present invention.
Claims (10)
1. yellow ultramarine that is used for the color liquid crystal colour filter, it is constituted by two or more at least compounds; It is characterized in that,
Described compound comprises the Compound I of following structural formula:
The Compound I I that also comprises following structural formula:
Wherein, Y representative-SO3X ,-SO2X ,-CH2-Z, n is the integer of 1-4;
X is the alkyl amine compound that contains 4 to 24 carbon atoms, or quarternary ammonium salt compound;
Z is the compound III of following structural formula:
Or alkyl amine compound, or quaternary ammonium salt;
Wherein, R represents the aliphatic hydrocarbon of 1-22 carbon atom, and m is the integer of 0-4.
2. according to the described preparation method who is used for the yellow ultramarine of color liquid crystal colour filter of claim 1, it is characterized in that, mainly comprise following operation:
A, be basic raw material with 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride, the composite structure formula is the yellow ultramarine crude product of Compound I;
The pigmenting processing of B, yellow ultramarine crude product.
3. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 2 is characterized in that, the synthetic method of described yellow ultramarine crude product is roughly as follows:
A. be in the inert high boiling solvent at trichlorobenzene or other, add 2-methyl-8-quinolylamine and tetrachlorophthalic anhydride, Zinc Chloride Anhydrous;
B. heat to boiling state, keep boiling number hour;
C. add dimethyl formamide, about 1 hour of stirring and refluxing;
D. filtered while hot then, and wash with dimethyl formamide;
E. use washing with alcohol at last, filter cake is through being drying to obtain the yellow ultramarine crude product that structural formula is a Compound I.
4. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 2 is characterized in that, described pigmenting manufacturing procedure comprises step:
One, the pre-grinding of yellow ultramarine crude product;
Two, the yellow ultramarine crude product after will grinding in advance carries out the pigmenting aftertreatment.
5. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 4 is characterized in that, the pre-grinding of described yellow ultramarine crude product may further comprise the steps:
A, the yellow ultramarine crude product of described Compound I is put into grinding plant grind; The add-on of crude pigment product suitably adds according to the volume of grinding plant, can be 5～30kg/100L;
Add in B, the grinding plant and account for a certain proportion of grinding medium of volume of equipment; Simultaneously, the inorganic salts grinding aid that all right an amount of adding can be water-soluble, the add-on of grinding aid is 5～50% of a pigment weight;
C, the described Compound I I of adding.
6. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 5, it is characterized in that, described Compound I I can add before grinding, grind with crude pigment product, also can add in the pigmenting post-processing stages, or aftertreatment finishes adding before filtering; The add-on of Compound I I is 0.5%～30% of a pigment weight.
7. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 4 is characterized in that, described pigmenting aftertreatment can be adopted solvent treatment method or mediate facture.
8. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 7 is characterized in that, described solvent treatment method is with the yellow ultramarine crude product through above-mentioned grinding, puts into a container that contains organic solvent and heat-treats;
In the solvent method treating processes, or before or after, Compound I I can be added in right amount.
9. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 8, it is characterized in that, described organic solvent can be the aliphatic alcohols, the arene that contain 1～8 carbon atom, have the substituent arene of halogen atom, and the compound of ketone, ethers, ester class.
10. the preparation method who is used for the yellow ultramarine of color liquid crystal colour filter according to claim 7, it is characterized in that, described kneading facture, be in a Z type oar kneader, drop into the yellow ultramarine crude product after described process is ground in advance, and add pulverizing inorganic salt grinding aid and organic solvent; Mediate temperature and be controlled at normal temperature to 130 ℃, the kneading time was controlled at 3～20 hours;
In the method for kneading treating processes, or before or after, Compound I I can be added in right amount;
After the processing of kneading method finishes, will expect that group pulls an oar in water, filter then that pigment is separated with other water-soluble impurity, and drying and crushing promptly obtains yellow ultramarine dry powder.
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| CN108864730A (en) * | 2018-08-10 | 2018-11-23 | 滨海明昇化工有限公司 | A kind of new process of pigment yellow PY138 production |
| CN109061931A (en) * | 2018-08-10 | 2018-12-21 | 滨海明昇化工有限公司 | A kind of preparation method of liquid crystal display PY138 derivative |
| KR20190026573A (en) * | 2017-09-04 | 2019-03-13 | 주식회사 엘지화학 | Coloring agent compound and coloring composition comprising the same |
| CN113462188A (en) * | 2021-06-16 | 2021-10-01 | 潍坊泰兴生物化工有限责任公司 | Pigment yellow 138 easily dispersible in weak solvent and preparation method thereof |
| CN113881242A (en) * | 2021-07-29 | 2022-01-04 | 潍坊泰兴生物化工有限责任公司 | Preparation method of low-yield-value pigment yellow PY138 product for tin printing ink |
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| KR20190026573A (en) * | 2017-09-04 | 2019-03-13 | 주식회사 엘지화학 | Coloring agent compound and coloring composition comprising the same |
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| CN109061931A (en) * | 2018-08-10 | 2018-12-21 | 滨海明昇化工有限公司 | A kind of preparation method of liquid crystal display PY138 derivative |
| CN109061931B (en) * | 2018-08-10 | 2021-03-09 | 山东盛宏安华化学有限公司 | Preparation method of PY138 derivative for liquid crystal display |
| CN113462188A (en) * | 2021-06-16 | 2021-10-01 | 潍坊泰兴生物化工有限责任公司 | Pigment yellow 138 easily dispersible in weak solvent and preparation method thereof |
| CN113462188B (en) * | 2021-06-16 | 2023-12-01 | 潍坊泰兴生物化工有限责任公司 | Pigment yellow 138 easy to disperse in weak solvent and preparation method thereof |
| CN113881242A (en) * | 2021-07-29 | 2022-01-04 | 潍坊泰兴生物化工有限责任公司 | Preparation method of low-yield-value pigment yellow PY138 product for tin printing ink |
| CN113881242B (en) * | 2021-07-29 | 2023-07-18 | 潍坊泰兴生物化工有限责任公司 | Preparation method of pigment yellow PY138 product with low yield value for iron printing ink |
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Application publication date: 20110119 |