CN101302357A - Preparation of yellow pigment for liquid printing ink - Google Patents
Preparation of yellow pigment for liquid printing ink Download PDFInfo
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- CN101302357A CN101302357A CN 200810052206 CN200810052206A CN101302357A CN 101302357 A CN101302357 A CN 101302357A CN 200810052206 CN200810052206 CN 200810052206 CN 200810052206 A CN200810052206 A CN 200810052206A CN 101302357 A CN101302357 A CN 101302357A
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- acetylacetanilide
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Abstract
The invention relates to a method for preparing a yellow pigment for liquid ink. The method comprises the following steps of : (1), adding one portion of 3.3'dichloro benzidine di hydrochloride into 5.3 portions of thirty percent of aqueous hydrochloric acid solution to disperse for one hour; adding 75 portions of ice water to cool to minus five to zero DEG C, using 2 portions of forty percent of sodium nitrite for diazotization and the terminating potassium iodide starch test paper shows dark blue; adding 0.1 to 0.3 portion of sulfamic acid until the potassium iodide starch test paper shows colorless for later use; (2), dissolving 2 portions of AAOT and 0.1 to 0.3 portion of second coupling component together in 6 portions of forty percent of Oxyhydrogen sodium solution under the temperature between twenty to thirty-two DEG C until the solution is transparent and adjusting the temperature to between eight and ten DEG C to acid out, that is, adding one hundred portions of water and three portions of acetic acid into an acetic acid thinning tank and stirring evenly to acid out slowly and obtain a coupling component; (3), adding diazo liquid into the coupling component about one hundred and twenty minutes to one hundred and fifty minutes when the PH value is between six and six point five and the temperature is between ten and fifteen DEG C until the complete coupling, then adding 0.01 to 0.05 portion of surface active agent and stirring; heating to eighty to ninety DEG C and preserving the heat for one to two hours, filtering and conducting pigmentation treatment on a filter mass. The method is simple in technology and remarkable in effect.
Description
Technical field
The present invention relates to a kind of preparation method of ink pigment, particularly a kind of preparation method who is used for the liquid ink yellow pigment.
Background technology
In recent years, domestic pigment worker carried out extensive studies for used for offset ink pigment, but will lack relatively with the research work of pigment for liquid ink, and along with China's printing packaging decoration industrial expansion, plastic packing product is increasing.The demand of liquid ink is increasing, and for pigment, the field difference of its application, the effect that obtains are different fully.Therefore the printing ink user requires more and more higher to pigment application performance in different field now.Pigment Yellow 14 is mainly used in the liquid ink, but its solvent resistance, sun-proof, shelf stability in polyurethane system and vinylformic acid system is all poor, and especially shelf stability is bad.
Therefore, provide a kind of technology simple, obvious results is used for the preparation method of liquid ink yellow pigment, is one of the current urgency of this field scientific research personnel difficult problem to be solved.
Summary of the invention
The objective of the invention is to overcome above-mentioned the deficiencies in the prior art part, a kind of solvent resistance and shelf stability of effective raising pigment is provided, the preparation method that technology is simple, obvious results is used for the liquid ink yellow pigment.
Implementation step of the present invention for achieving the above object is as follows:
A kind of preparation method who is used for the liquid ink yellow pigment is characterized in that implementation step is as follows:
(1) gets 1 part of 3.3 ' dichlorobenzidine and join in 5.3 part of 30% aqueous hydrochloric acid, disperseed 1 hour; Add 75 parts frozen water cooling-5-0 ℃, with 2 part of 40% Sodium Nitrite diazotization, terminal point guarantees that potassium iodide starch test paper is a mazarine; Adding 0.1-0.3 part thionamic acid is colourless, stand-by to potassium iodide starch test paper;
(2) get 2 parts of adjacent methyl alpha.-acetylacetanilides, 0.1-0.3 part second coupling component is dissolved in 6 part of 40% aqueous sodium hydroxide solution jointly, temperature 20-32 ℃, dissolve transparently, adjust temperature to 8-10 ℃ of acid out; In the acetic acid thinning tank, add 100 parts in water, 3 parts of acetic acid, stir, slowly carry out acid out; Obtain coupling component;
(3) when pH is 6.0-6.5, temperature 10-15 ℃, joined in the coupling component diazonium liquid complete until coupling with 120-150 minute; Add 0.01-0.05 part tensio-active agent and stir, or add the stirring of 0.01-0.05 part tensio-active agent when obtaining coupling component in step (2); Be warming up to 80-90 ℃, be incubated 1-2 hour, filter; Filter cake carries out pigmenting routinely to be handled.
Described second coupling component select for use 2.4-dimethyl alpha.-acetylacetanilide, orthomethoxy-acetoacetanilide, alpha.-acetylacetanilide, 5-ethanoyl acetamino benzimidazolone, to the methoxyl group alpha.-acetylacetanilide, to methyl alpha.-acetylacetanilide, ortho-chloro-ace toacetanilide, adjacent nitro alpha.-acetylacetanilide, 1-phenyl-3 methyl-5-pyrazolone, 1-(3-sulphenyl)-3-methyl-pyrazolone one or more.
Described tensio-active agent select for use anion surfactant, nonionogenic tenside, acrylic copolymer, alkylphenol polyoxyethylene, fatty alcohol-polyoxyethylene ether two or more.
Reaction mechanism of the present invention is as follows:
Introduce the coupling polycomponent, increase pigment molecule amount 2.4-dimethyl alpha.-acetylacetanilide, orthomethoxy-acetoacetanilide, alpha.-acetylacetanilide, 5-ethanoyl acetamino benzimidazolone, to the methoxyl group alpha.-acetylacetanilide, to methyl alpha.-acetylacetanilide, ortho-chloro-ace toacetanilide, adjacent nitro alpha.-acetylacetanilide, 1-phenyl-3 methyl-5-pyrazolone, 1-(3-sulphenyl)-3-methyl-pyrazolone etc.
(in pigment molecule, introduce other substituted radical-Cl ,-OCH
3,-CONH-, benzopyrazoles ketone, phthalic imidine class etc.)
With a kind of coupling component coupling, its coloured light and solvent resistance are all than the pigment poor solvent resistance of introducing second coupling component, and be dispersed bad in coupling component.So when pigment was synthetic, present method adopts added the coupling altogether of 1-10% second coupling component.Increase the pigment molecule amount, improve the solvent resistance of pigment, for solving the bad problem of pigment shelf stability, present method adopts strong tensio-active agent of 1-5% polarity or pigment derivative to change surface of pigments polarity, and pigment and working medium are complementary.Present method changes the direction of crystal growth or suppresses rate of crystal growth as the crystal growth inhibitor by the pigment derivative (acrylic copolymer, alkylphenol polyoxyethylene, fatty alcohol-polyoxyethylene ether etc.) of adding ad hoc structure, according to the difference of kinds of surfactants, change the pigment particles surface polarity.Mainly act as: adopt the polar functionalities derivative as particle crystal growth inhibitor, implement the pigment particles surface modification, interact, the additive covering surfaces is combined with alkaline dispersing agent according to intermolecular hydrogen bonding or acid, alkali; Reduce the yield value of pigment significantly; Improve its flocculation resistance with ion stabilized mechanism; Has higher tinctorial strength agent color saturation.Drying conditions still has considerable influence to the pigment quality in the pigment last handling process in addition, and drying is heat treated a kind of.Drying temperature, time of drying, drying mode can both change the characteristic of granules of pigments.When pigment exists with filter cake, be slight cohesion between its particle, be easy in water, disperse again.Yet water causes agglomeration of particles along with the capillary evaporation between the particle when high temperature oven is dry, and pigment becomes lump, is difficult for disperseing.Changing drying temperature is to having the adjustment of crystal formation, particle distribution.Temperature raises, the ion vibration, thus form new crystal formation; But also might the temperature rising can not influence crystal formation, just ion vibration aggravation changes the viscosity of pigment to some extent.
The invention has the beneficial effects as follows: the inventive method is that to utilize adduction synergic principle be the coupling altogether of diazo component and two or more coupling component with the binary arylamine, change surface of pigments polarity handling through pigment derivative, make it form pigment, be highly suitable for polyurethane system or vinylformic acid system gravure ink.The performance of pigment in polyurethane system and vinylformic acid system for a change, mainly according to pigment characteristics change pigment crystal formation, improve the dispersiveness of pigment in polyurethane system and vinylformic acid system, to increase the solvent resistance and the shelf stability of pigment.Make pigment be adapted to applied system, in building-up process, change the pigment crystalline form, effectively carry out the surface treatment of pigment and satisfy the higher requirement of printing ink.When this pigment was used for solvent inkjet ink or water color ink, this pigment has splendid solvent resistance, and (pigment dispersed fabulous in solvent, it was low to show as viscosity.) and shelf stability (viscosity has minimum variation deposit 72 hours or 96 hours in 50 ℃ of environment after).Technology of the present invention is simple, and effect is remarkable, effectively improves the quality of products.
Embodiment
Below in conjunction with preferred embodiment, to details are as follows according to embodiment provided by the invention:
Embodiment 1
(1) gets 1kg3.3 ' dichlorobenzidine and join in the 5.3kg30% aqueous hydrochloric acid, disperseed 1 hour; Add cooling-5-0 ℃ of 75kg frozen water, with 2kg40% Sodium Nitrite diazotization, terminal point guarantees that potassium iodide starch test paper is a mazarine; Adding the 0.1-0.3kg thionamic acid is colourless, stand-by to potassium iodide starch test paper;
(2) get the adjacent methyl alpha.-acetylacetanilide of 2kg, 0.1kg second coupling component is dissolved in 6kg 40% aqueous sodium hydroxide solution jointly, temperature 20-32 ℃, dissolve transparently, adjust temperature and arrive 8-10 ℃ of acid out; Promptly in the acetic acid thinning tank, add water 100kg water, acetic acid 3kg, stir, slowly carry out acid out, get coupling component;
(3) at pH=6.0-6.5, in the time of temperature 10-15 ℃, with 120-150 minute diazonium liquid is joined in the coupling component fully until coupling, add the 0.01-0.05kg tensio-active agent and stir; Be warmed up to 80-90 ℃, be incubated 1-2 hour, filter, filter cake carries out pigmenting routinely to be handled.
Described second coupling component select for use 2.4-dimethyl alpha.-acetylacetanilide, orthomethoxy-acetoacetanilide, alpha.-acetylacetanilide, 5-ethanoyl acetamino benzimidazolone, to the methoxyl group alpha.-acetylacetanilide, to methyl alpha.-acetylacetanilide, ortho-chloro-ace toacetanilide, adjacent nitro alpha.-acetylacetanilide, 1-phenyl-3 methyl-5-pyrazolone, 1-(3-sulphenyl)-3-methyl-pyrazolone one or more.
Described tensio-active agent select for use anion surfactant, nonionogenic tenside, acrylic copolymer, alkylphenol polyoxyethylene, fatty alcohol-polyoxyethylene ether two or more.
Embodiment 2
(1) gets 1kg3.3 ' dichlorobenzidine and join in the 5.3kg30% aqueous hydrochloric acid, disperseed 1 hour; Add the 75kg frozen water and cool to-5-0 ℃, with 2kg40% Sodium Nitrite diazotization, terminal point guarantees that potassium iodide starch test paper is a mazarine; Adding the 0.1-0.3kg thionamic acid is colourless, stand-by to potassium iodide starch test paper;
(2) get the adjacent methyl alpha.-acetylacetanilide of 2kg, second group of coupling component of 0.3kg is dissolved in 6kg 40% aqueous sodium hydroxide solution jointly, temperature 20-32 ℃, dissolve transparently, adjust temperature and arrive 8-10 ℃ of acid out; Promptly in the acetic acid thinning tank, add water 100kg, acetic acid 3kg, stir, slowly carry out acid out, get coupling component;
(3) at pH=6.0-6.5, in the time of temperature 10-15 ℃, with 120-150 minute diazonium liquid is joined in the coupling component fully until coupling, add the 0.01-0.05kg tensio-active agent and stir; Be warmed up to 80-90 ℃, be incubated 1-2 hour, filter, filter cake carries out pigmenting routinely to be handled.
Selecting for use of described second coupling component and tensio-active agent with embodiment 1.
Embodiment 3
(1) gets 1kg3.3 ' dichlorobenzidine and join in the 5.3kg30% aqueous hydrochloric acid, disperseed 1 hour; Add the 75kg frozen water and cool to-5-0 ℃,, guarantee that potassium iodide starch test paper is a mazarine with 2kg 40% Sodium Nitrite diazotization; Adding the 0.1-0.3kg thionamic acid is colourless, stand-by to potassium iodide starch test paper;
(2) get the adjacent methyl alpha.-acetylacetanilide of 2kg, second group of coupling component of 0.3kg is dissolved in the 6kg40% aqueous sodium hydroxide solution jointly, temperature 20-32 ℃, dissolve transparently, adjust temperature and arrive 8-10 ℃ of acid out; Promptly in the acetic acid thinning tank, add water 100kg, acetic acid 3kg, stir, slowly carry out acid out, obtain coupling component, add the 0.01-0.05kg tensio-active agent and stir;
(3), in the time of temperature 10-15 ℃, joined in the coupling component diazonium liquid complete until coupling with 120-150 minute at pH=6.0-6.5; Be warmed up to 80-90 ℃, be incubated 1-2 hour, filter, filter cake carries out pigmenting routinely to be handled.
Selecting for use of described second coupling component and tensio-active agent with embodiment 1.
Application example
With 10 parts of a kind of pigment, 90 parts in the low-melting ink vehicle mixture that following described ratio is arranged and 100 parts of mixing of 2-3mm granulated glass sphere, with vibrator said mixture was disperseed 60 minutes, can obtain polyurethane ink.Examine the viscosity that the grace cup is measured polyurethane ink with 4#.Polyurethane ink kept 3-7 days in 40-50 ℃ of environment, measured the viscosity of this polyurethane ink then, deposited 4-10 days stability to estimate in 40-50 ℃ of environment of this polyurethane ink.
The low-melting ink vehicle mixture ratio
50 parts of urethane resins
350 parts of organic solvents
Help 25 parts of resins
10 parts of dispersion agents
The various parameter comparison of the present invention and currently available products are as follows:
| Test item | Currently available products | Embodiment 1 | Embodiment 2 | Embodiment 3 |
| Aberration L value | 32.45 | 33.13 | 31.06 | 32.76 |
| Gloss | 43.27 | 43.12 | 44.28 | 43.46 |
| Viscosity (4# examines the grace cup) second | 17″24 | 10″23 | 9″11 | 8″88 |
| Shelf stability (viscosity after 40 ℃, 72 hours) second | 28″72 | 13″02 | 11″66 | 9″56 |
Above-mentioned detailed description of this preparation method who is used for the liquid ink yellow pigment being carried out with reference to embodiment; be illustrative rather than determinate; can exemplify out several embodiment according to institute's limited range; therefore in the variation and the modification that do not break away under the general plotting of the present invention, should belong within protection scope of the present invention.
Claims (3)
1, a kind of preparation method who is used for the liquid ink yellow pigment is characterized in that implementation step is as follows:
(1) gets 1 part of 3.3 ' dichlorobenzidine and join in 5.3 part of 30% aqueous hydrochloric acid, disperseed 1 hour; Add 75 parts frozen water cooling-5-0 ℃, with 2 part of 40% Sodium Nitrite diazotization, terminal point guarantees that potassium iodide starch test paper is a mazarine; Adding 0.1-0.3 part thionamic acid is colourless, stand-by to potassium iodide starch test paper;
(2) get 2 parts of adjacent methyl alpha.-acetylacetanilides, 0.1-0.3 part second coupling component is dissolved in 6 part of 40% aqueous sodium hydroxide solution jointly, temperature 20-32 ℃, dissolve transparently, adjust temperature to 8-10 ℃ of acid out; In the acetic acid thinning tank, add 100 parts in water, 3 parts of acetic acid, stir, slowly carry out acid out; Obtain coupling component;
(3) when pH is 6.0-6.5, temperature 10-15 ℃, joined in the coupling component diazonium liquid complete until coupling with 120-150 minute; Add 0.01-0.05 part tensio-active agent and stir, or add the stirring of 0.01-0.05 part tensio-active agent when obtaining coupling component in step (2); Be warming up to 80-90 ℃, be incubated 1-2 hour, filter; Filter cake carries out pigmenting routinely to be handled.
2, the preparation method who is used for the liquid ink yellow pigment according to claim 1, it is characterized in that described second coupling component select for use 2.4-dimethyl alpha.-acetylacetanilide, orthomethoxy-acetoacetanilide, alpha.-acetylacetanilide, 5-ethanoyl acetamino benzimidazolone, to the methoxyl group alpha.-acetylacetanilide, to methyl alpha.-acetylacetanilide, ortho-chloro-ace toacetanilide, adjacent nitro alpha.-acetylacetanilide, 1-phenyl-3 methyl-5-pyrazolone, 1-(3-sulphenyl)-3-methyl-pyrazolone one or more.
3, the preparation method who is used for the liquid ink yellow pigment according to claim 1, it is characterized in that described tensio-active agent select for use anion surfactant, nonionogenic tenside, acrylic copolymer, alkylphenol polyoxyethylene, fatty alcohol-polyoxyethylene ether two or more.
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| CN 200810052206 CN101302357A (en) | 2008-01-29 | 2008-01-29 | Preparation of yellow pigment for liquid printing ink |
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| CN 200810052206 CN101302357A (en) | 2008-01-29 | 2008-01-29 | Preparation of yellow pigment for liquid printing ink |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101914301A (en) * | 2010-07-28 | 2010-12-15 | 吴江市屯村颜料厂 | Method for preparing lightfast pigment yellow G |
| CN102311659A (en) * | 2010-07-07 | 2012-01-11 | 龙口联合化学有限公司 | Preparation method of pigment used for nitrocotton solvent ink |
| CN102643138A (en) * | 2012-04-06 | 2012-08-22 | 胡锋 | Preparation method and product of chemical fertilizer dyeing promoter |
| CN103382161A (en) * | 2013-07-31 | 2013-11-06 | 瑞安宝源化工有限公司 | Preparation technique for diazo liquid of benzidine yellow G |
| CN104263002A (en) * | 2014-08-19 | 2015-01-07 | 上虞市东海化工有限公司 | Preparation method of yellow pigment |
| CN106349735A (en) * | 2016-08-30 | 2017-01-25 | 上虞市东海化工有限公司 | Preparing method for yellow paint |
| CN106752254A (en) * | 2016-12-06 | 2017-05-31 | 浙江力禾集团有限公司 | A kind of production method of the special C.I. pigment Yellow 14s of water paint |
| CN107532023A (en) * | 2015-07-17 | 2018-01-02 | 惠普深蓝有限责任公司 | electrostatic ink composition |
| CN108929557A (en) * | 2018-08-13 | 2018-12-04 | 山东宇虹新颜料股份有限公司 | A kind of preparation method of aqueous ink organic pigment |
| CN109593381A (en) * | 2018-12-29 | 2019-04-09 | 瑞安宝源化工有限公司 | The preparation method of high grade of transparency height flowing pigment permanent yellow 174 |
| CN109593385A (en) * | 2018-11-20 | 2019-04-09 | 宣城英特颜料有限公司 | A kind of preparation method of forever solid orange pigment |
| CN109971205A (en) * | 2019-04-19 | 2019-07-05 | 龙口联合化学有限公司 | The preparation method of pigment derivative, polyurethane ink pigment and the two |
| CN114350174A (en) * | 2021-12-27 | 2022-04-15 | 江西隆源化工股份有限公司 | Preparation method of organic pigment with high covering power and sun-proof property of more than 7 grade and applied to paint |
-
2008
- 2008-01-29 CN CN 200810052206 patent/CN101302357A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311659A (en) * | 2010-07-07 | 2012-01-11 | 龙口联合化学有限公司 | Preparation method of pigment used for nitrocotton solvent ink |
| CN101914301A (en) * | 2010-07-28 | 2010-12-15 | 吴江市屯村颜料厂 | Method for preparing lightfast pigment yellow G |
| CN102643138A (en) * | 2012-04-06 | 2012-08-22 | 胡锋 | Preparation method and product of chemical fertilizer dyeing promoter |
| CN103382161A (en) * | 2013-07-31 | 2013-11-06 | 瑞安宝源化工有限公司 | Preparation technique for diazo liquid of benzidine yellow G |
| CN104263002A (en) * | 2014-08-19 | 2015-01-07 | 上虞市东海化工有限公司 | Preparation method of yellow pigment |
| CN107532023A (en) * | 2015-07-17 | 2018-01-02 | 惠普深蓝有限责任公司 | electrostatic ink composition |
| CN106349735A (en) * | 2016-08-30 | 2017-01-25 | 上虞市东海化工有限公司 | Preparing method for yellow paint |
| CN106752254A (en) * | 2016-12-06 | 2017-05-31 | 浙江力禾集团有限公司 | A kind of production method of the special C.I. pigment Yellow 14s of water paint |
| CN108929557A (en) * | 2018-08-13 | 2018-12-04 | 山东宇虹新颜料股份有限公司 | A kind of preparation method of aqueous ink organic pigment |
| CN108929557B (en) * | 2018-08-13 | 2019-11-05 | 山东宇虹新颜料股份有限公司 | A kind of preparation method of aqueous ink organic pigment |
| CN109593385A (en) * | 2018-11-20 | 2019-04-09 | 宣城英特颜料有限公司 | A kind of preparation method of forever solid orange pigment |
| CN109593381A (en) * | 2018-12-29 | 2019-04-09 | 瑞安宝源化工有限公司 | The preparation method of high grade of transparency height flowing pigment permanent yellow 174 |
| CN109971205A (en) * | 2019-04-19 | 2019-07-05 | 龙口联合化学有限公司 | The preparation method of pigment derivative, polyurethane ink pigment and the two |
| CN114350174A (en) * | 2021-12-27 | 2022-04-15 | 江西隆源化工股份有限公司 | Preparation method of organic pigment with high covering power and sun-proof property of more than 7 grade and applied to paint |
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Open date: 20081112 |