CN100363434C - Method for preparing Nano red organic pigment - Google Patents

Method for preparing Nano red organic pigment Download PDF

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Publication number
CN100363434C
CN100363434C CNB2005100180753A CN200510018075A CN100363434C CN 100363434 C CN100363434 C CN 100363434C CN B2005100180753 A CNB2005100180753 A CN B2005100180753A CN 200510018075 A CN200510018075 A CN 200510018075A CN 100363434 C CN100363434 C CN 100363434C
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acid
organic pigment
reaction
red organic
nano red
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CN1760283A (en
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董书山
吴雪峰
高杰
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Henan Huanghe Whirlwind Co Ltd
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Henan Huanghe Whirlwind Co Ltd
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Abstract

The present invention relates to a method for preparing azo pigment, particularly to a method for preparing nano red organic pigment. At present, the temperature of a reaction environment is 0 DEG C, and condition requirements are strict in a diazo process for preparing the red organic pigment. The present invention is characterized in that diazo reaction is implemented between arylamine sulfonic acid and nitrite at a temperature of 15 to 30 DEG C, and the product is mixed with 2-hydroxy-3-naphthaleneformic acid prepared under the condition of room temperature to be coupled into sodium salt. A stirring speed is from 800 to 20000 revolutions per minute. Then, alkaline earth metal salt is added to be converted, filtered, washed for many times and dried in a vacuum mode to obtain the nano red organic pigment. Compared with the original method for preparing azo organic pigment, the method for preparing the nano red organic pigment has the advantages of free technological condition and simple operation. The obtained red organic pigment has the advantages of small particle size, high coloring strength, high dispersivity, high stability, no discoloration by coming into contact with dilute acid, etc. and is widely applied to the fields of printing ink, paint, etc., which have high requirements for a particle size and weatherability.

Description

The preparation method of Nano red organic pigment
One. technical field: the present invention relates to a kind of preparation method of azo pigment, particularly relate to a kind of preparation method of Nano red organic pigment.
Two. background technology: at present, the basic production method of azo pigment is diazotization reaction and coupled reaction.The azoic dyestuff color lake of containing sulfonic acid or carboxylic acid group also needs to be transformed into from sodium salt the conversion process of alkaline earth salt (or other metal-salt) except above-mentioned two steps.For the diazo process in the organic red pigment preparation, its reaction environment is 0 ℃, make to be reflected in the mixture of ice and water and carry out in a large number with directly cooling of ice.Reaction conditions requires harsh.For coupled reaction, normally in the coupling bucket, put into water, add alkali lye, drop into 2,3 acid after being heated to 60 ℃, temperature to 15 ℃ is adjusted in complete molten back, diazonium liquid is added wherein carry out coupling, and technological process is more loaded down with trivial details, and energy consumption is bigger, causes cost higher.It is red-purple that the permanent bordeaux of prior art for preparing is met the vitriol oil, meets diluted acid and is blue light; Chance nitric acid is red-brown.
Three. summary of the invention:
The objective of the invention is: the preparation condition at existing organic red pigment improves, and provides that a kind of technology is simple, the preparation method of the simple Nano red organic pigment of reaction conditions.
Technical scheme of the present invention is:
The invention provides a kind of preparation method of Nano red organic pigment, it is to make sodium salt by carrying out coupled reaction with 2-hydroxyl-3-naphthoic acid in the weak base medium after the arylamine sulfonic acid diazotization reaction, adding alkaline earth salt then transforms, filter, repeatedly flushing, vacuum-drying gets Nano red organic pigment; The diazotization reaction of arylamine sulfonic acid and coupled reaction all are to carry out under 15~30 ℃ temperature, wherein:
(1), the stirring velocity when obtain solution and reaction is 10000~20000 rev/mins;
(2), vacuum-drying is to carry out in vacuum drying oven, vacuum tightness is 10 -2~10 -3Pa, Heating temperature is 60~90 ℃.
In the preparation method of Nano red organic pigment, the raw materials used 2-of having amino in the described arylamine sulfonic acid diazotization reaction-4-chloro-5-toluene sulfonic acide is commonly called as 2B acid or 2B acid and sodium hydroxide/potassium hydroxide, 10~30% diluted acids, Sodium Nitrite.
In the preparation method of Nano red organic pigment, the raw materials used 2-of having hydroxyl-3-naphthoic acid is commonly called as 2,3 acid or 2,3 acid and sodium hydroxide/potassium hydroxide in the described coupled reaction; Described alkaline earth salt is a calcium chloride, bariumchloride, Manganous chloride tetrahydrate.
In the preparation method of Nano red organic pigment, described diluted acid is dilute hydrochloric acid or dilute sulphuric acid.
In the preparation method of Nano red organic pigment, 2B acid was 1: 3~20 with the mol ratio of diluted acid during described diazotization reaction was raw materials used, 2B acid is 1: 1~12 with the mol ratio of sodium hydroxide/potassium hydroxide, and 2B acid is 1: 1~1.8 with the mol ratio of Sodium Nitrite.
In the preparation method of Nano red organic pigment, 2,3 acid were that 1: 1~3.5,2,3 sour mol ratios with sodium hydroxide/potassium hydroxide are 1: 1~7 with the mol ratio of calcium chloride during described coupled reaction was raw materials used.
In the preparation method of Nano red organic pigment, be 3~4 hours heat-up time during vacuum-drying.
Positive beneficial effect of the present invention is:
1. the preparation method of Nano red organic pigment of the present invention, processing condition require loose, and diazotization reaction, coupled reaction all are to carry out under 15~30 ℃ temperature.
2. the preparation method of Nano red organic pigment of the present invention, prepared organic red pigment has less granularity.Employing stirring speed is 10000~20000 rev/mins and vacuumizes the method for heat drying, can reduce particulate reunion degree, helps obtaining nano-scale particle and improves productive rate.Table 1 is the influence of reaction conditions to productive rate and granularity.
Table 1: reaction conditions is to the influence of productive rate and granularity
Stir (rev/min) Dry Starting material
800~1000 2000 5000~8000 10000~20000 Vacuum-drying A conventional oven 2B acid 2B acid+NaOH 2B acid sodium
Productive rate Generally Higher High High High Generally Higher High High
Granularity Greatly Bigger Less Little Little Greatly Greatly Little Little
3. Nano red organic pigment of the present invention has tinctorial strength height, good dispersity, meets the diluted acid nondiscoloration, in concentration is 40% sulfuric acid, can not present blue light.
4. the preparation method of Nano red organic pigment of the present invention has raw material and is easy to get, and simple to operate, low cost and other advantages can be widely used in the field that printing ink, coating etc. have higher requirements to granularity, weathering resistance.
Four. description of drawings:
Fig. 1 is mixing speed resulting organic red transmission electron microscope (TEM) figure under 800~1000 rev/mins condition;
Fig. 2 is mixing speed resulting organic red transmission electron microscope (TEM) figure under 2000~5000 rev/mins condition;
Fig. 3 is mixing speed resulting organic red transmission electron microscope (TEM) figure under 8000 rev/mins condition;
Fig. 4 is mixing speed resulting organic red transmission electron microscope (TEM) figure under 10000~20000 rev/mins condition;
Five. embodiment:
Embodiment one:
Diazotization reaction: take by weighing the sour dilute hydrochloric acid 5L of 1.0kg 2B and mix, (rotating speed: 800r/min) add solid sodium nitrite 0.4kg (excessive slightly) and carry out diazotization reaction under the agitation condition with 10%.
Coupled reaction: take by weighing in 1.0kg 2, the 3 sour 5L water (rotating speed: 800r/min) sodium hydroxide to 2, the 3 sour complete reactions of adding 1.2kg under the agitation condition.Mix with the diazotization product and to carry out coupling, continue in the reaction process to stir.Coupling adds 1.0kg CaCl fully 2Reacted 2 hours, and stirred simultaneously, get red precipitate 2.01kg.After-filtration, flushing, pH value is 7.4 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 1.954kg.
Productive rate: 97.2%, granularity: 200~250nm
Embodiment two:
Diazotization reaction: take by weighing 0.5kg 2B acid and add in the dilute hydrochloric acid solution of 2L 10%.In mixed solution, add solid sodium nitrite 0.2kg and carry out diazotization reaction.
Coupled reaction: take by weighing 0.6kg 2,3 sour sodium and add in the 2L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 1000r/min) in the reaction process.Coupling adds 0.6kg CaCl fully 2Reaction 3h stirs simultaneously, gets red precipitate 1.00kg.After-filtration, flushing, pH value is 7.8 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 0.973kg.
Productive rate: 97.3%, granularity: 200~250nm
Embodiment three:
Diazotization reaction: take by weighing 0.5kg 2B acid and add in the dilution heat of sulfuric acid of 2L 10%.In mixed solution, add solid sodium nitrite 0.2kg and carry out diazotization reaction.
Coupled reaction: take by weighing 0.6kg 2,3 sour sodium and add in the 2L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 1000r/min) in the reaction process.Coupling adds 0.6kg CaCl fully 2Reaction 2h stirs simultaneously, gets red precipitate 1.00kg.After-filtration, flushing, pH value is 7.9 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 0.975kg.
Productive rate: 97.5%, granularity: 200~250nm
Embodiment four:
Diazotization reaction: take by weighing 0.5kg 2B acid and add in the dilute hydrochloric acid solution of 2L 10%.In mixed solution, add solid sodium nitrite 0.2kg and carry out diazotization reaction.
Coupled reaction: take by weighing 0.6kg 2,3 sour sodium and add in the 2L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 2000r/min) in the reaction process.Coupling adds 0.6kg CaCl fully 2Reaction 2h stirs simultaneously, gets red precipitate 1.00kg.After-filtration, flushing, pH value is 7.5 after repeatedly cleaning, a conventional oven drying (drying temperature<90 ℃) must 0.971kg.
Productive rate: 97.1%, granularity: 150~200nm
Embodiment five:
Diazotization reaction: take by weighing the sour 2L of adding of 0.5kg 2B water, add 1.0kg NaOH and make 2B acid generate 2B acid sodium fully, (rotating speed: the hydrochloric acid 3.5L of adding 30% does not separate out to there being precipitation 5000r/min) in stirring then.In precipitated liquid, add solid sodium nitrite 0.2kg and carry out diazotization reaction.
Coupled reaction: take by weighing in 0.6kg 2, the 3 sour 2L water (rotating speed: 5000r/min) sodium hydroxide to 2, the 3 sour complete reactions of adding 0.8kg under the agitation condition.Mix with the diazotization product and to carry out coupling, continue in the reaction process to stir.Coupling adds 0.6kg CaCl fully 2Reaction 1h stirs simultaneously, gets red precipitate 1.00kg.After-filtration, flushing, pH value is 7.7 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 0.985kg.
Productive rate: 98.5%, granularity: 150~200nm
Embodiment six:
Diazotization reaction: take by weighing the sour 8L of adding of 1.5kg 2B water, add 3.0kg NaOH and make 2B acid generate 2B acid sodium fully, (rotating speed: the hydrochloric acid 10L of adding 30% does not separate out to there being precipitation 8000r/min) in stirring then.In precipitated liquid, add solid sodium nitrite 0.6kg and carry out diazotization reaction.
Coupled reaction: take by weighing 1.6kg 2,3 sour sodium and add in the 8L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 8000r/min) in the reaction process.Coupling adds 1.6kg CaCl fully 2Reaction 0.5h stirs simultaneously, gets red precipitate 3.02kg.After-filtration, flushing, pH value is 7.4 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 2.978kg.
Productive rate: 98.6%, granularity: 100~150nm
Embodiment seven:
Diazotization reaction: take by weighing the sour 4L of adding of 0.8kg 2B water, add 1.6kg NaOH and make 2B acid generate 2B acid sodium fully, (rotating speed: the sulfuric acid 12L of adding 10% does not separate out to there being precipitation 10000r/min) in stirring then.In precipitated liquid, add solid sodium nitrite 0.4kg and carry out diazotization reaction.
Coupled reaction: take by weighing in 0.8kg 2, the 3 sour 4L water, (rotating speed: 10000r/min) add sodium hydroxide 1.0kg to 2,3 sour complete reactions, the back mixing with the diazotization product carried out coupling, continues in the reaction process to stir under the agitation condition.Coupling adds 1.0kg CaCl fully 2Reaction 0.5h stirs simultaneously, gets red precipitate 1.60kg.After-filtration, flushing, vacuum and heating drying (drying temperature<90 ℃) 1.58kg.
Productive rate: 98.75%, granularity: 50~100nm
Embodiment eight:
Diazotization reaction: take by weighing 0.6kg 2B acid sodium and be dissolved in 2L water, (rotating speed: the hydrochloric acid 1L of adding 30% does not go out to there being the 2B acid out 15000r/min) in stirring in the back.In precipitated liquid, add solid sodium nitrite 0.3kg and carry out diazotization reaction.
Coupled reaction: take by weighing 0.6kg 2,3 sour sodium and add in the 2L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 15000r/min) in the reaction process.Coupling adds 1.0kg CaCl fully 2Reaction 0.5h stirs simultaneously, gets red precipitate 1.09kg.After-filtration, flushing, vacuum and heating drying (drying temperature<90 ℃) 1.08kg.
Productive rate: 99.08%, granularity: 50nm
Embodiment nine:
Diazotization reaction: take by weighing 1.0kg 2B acid sodium and add 5L water, (rotating speed: the sulfuric acid 1.5L of adding 10% does not separate out to there being precipitation 20000r/min) in stirring.In precipitated liquid, add solid sodium nitrite 0.4kg and carry out diazotization reaction.
Coupled reaction: take by weighing 1.0kg 2,3 sour sodium and add in the 5L water, mix the sodium hydroxide that adds 1.2kg simultaneously with the diazotization product and under alkaline condition, carry out coupling, constantly stir (rotating speed: 20000r/min) in the reaction process.Coupling adds 1.0kg CaCl fully 2Reaction 0.5h stirs simultaneously, gets red precipitate 1.828kg.After-filtration, flushing, pH value is 7.9 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 1.808kg.
Productive rate: 98.9%, granularity: 20~50nm
Embodiment ten:
Diazotization reaction: take by weighing 0.8kg 2B acid sodium and be dissolved in 5L water, (rotating speed: the hydrochloric acid 1L of adding 30% does not go out to there being the 2B acid out 20000r/min) in stirring.In precipitated liquid, add solid sodium nitrite 0.3kg and carry out diazotization reaction.
Coupled reaction: take by weighing 0.8kg 2,3 sour sodium and add in the 5L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 20000r/min) in the reaction process.Coupling adds 1.0kg CaCl fully 2Reaction 2h stirs simultaneously, gets red precipitate 1.453kg.After-filtration, flushing, pH value is 7.6 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 1.437kg.
Productive rate: 98.9%, granularity: 20~50nm
Embodiment 11:
Diazotization reaction: take by weighing 1.5kg 2B acid sodium and be dissolved in 8L water, (rotating speed: the hydrochloric acid 1L of adding 30% does not go out to there being the 2B acid out 20000r/min) in stirring.In precipitated liquid, add solid sodium nitrite 0.6kg and carry out diazotization reaction.
Coupled reaction: take by weighing 1.5kg 2,3 sour sodium and add in the 8L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 20000r/min) in the reaction process.Coupling adds 1.0kg CaCl fully 2Reaction 1h stirs simultaneously, gets red precipitate 2.724kg.After-filtration, flushing, pH value is 7.6 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 2.691kg.
Productive rate: 98.8%, granularity: 20~50nm
Embodiment 12:
Diazotization reaction: take by weighing the sour 8L of adding of 1.5kg 2B water, add 3.0kg NaOH and make 2B acid generate 2B acid sodium fully, (rotating speed: the hydrochloric acid 10L of adding 30% does not separate out to there being precipitation 20000r/min) in stirring then.In precipitated liquid, add solid sodium nitrite 0.6kg and carry out diazotization reaction.
Coupled reaction: take by weighing 1.6kg 2,3 sour sodium and add in the 8L water, mix with the diazotization product and carry out coupling, constantly stir (rotating speed: 20000r/min) in the reaction process.Coupling adds 1.6kg CaCl fully 2Reaction 1h stirs simultaneously, gets red precipitate 3.02kg.After-filtration, flushing, pH value is 7.8 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 2.978kg.
Productive rate: 98.6%, granularity: 20~50nm
Embodiment 13:
Diazotization reaction: take by weighing the sour 6L of adding of 1.0kg 2B water, add 2.0kg NaOH and make 2B acid generate 2B acid sodium fully, (rotating speed: the hydrochloric acid 8L of adding 30% does not separate out to there being precipitation 20000r/min) in stirring then.In precipitated liquid, add solid sodium nitrite 0.4kg (excessive slightly) and carry out diazotization reaction.
Coupled reaction: take by weighing in 1.0kg 2, the 3 sour 6L water (rotating speed: 20000r/min) sodium hydroxide to 2, the 3 sour complete reactions (the molten and water of 2,3 sour sodium) of adding 1.2kg under the agitation condition.Mix with the diazotization product and to carry out coupling, continue in the reaction process to stir.Coupling adds 1.0kg CaCl fully 2Reaction 1h stirs simultaneously, gets red precipitate 2.01kg.After-filtration, flushing, pH value is 7.5 after repeatedly cleaning, vacuum and heating drying (drying temperature<90 ℃) must 1.978kg.
Productive rate: 98.4%, granularity: 20~50n

Claims (7)

1. the preparation method of a Nano red organic pigment, it is to make sodium salt by carrying out coupled reaction with 2-hydroxyl-3-naphthoic acid in the weak base medium after the arylamine sulfonic acid diazotization reaction, adds alkaline earth salt then and transforms, and filters, repeatedly flushing, vacuum-drying gets Nano red organic pigment; The diazotization reaction of arylamine sulfonic acid and coupled reaction all are to carry out under 15~30 ℃ temperature, it is characterized in that:
Stirring velocity when (1) obtain solution is with reaction is 10000~20000 rev/mins;
(2) vacuum-drying is to carry out in vacuum drying oven, and vacuum tightness is 10 -2~10 -3Pa, Heating temperature is 60~90 ℃.
2. the preparation method of Nano red organic pigment according to claim 1, it is characterized in that: the raw materials used 2-of having amino in the described arylamine sulfonic acid diazotization reaction-4-chloro-5-toluene sulfonic acide is commonly called as 2B acid or 2B acid and sodium hydroxide/potassium hydroxide, 10~30% diluted acids, Sodium Nitrite.
3. the preparation method of Nano red organic pigment according to claim 1 is characterized in that: the raw materials used 2-of having hydroxyl-3-naphthoic acid is commonly called as 2,3 acid or 2,3 acid and sodium hydroxide/potassium hydroxide in the described coupled reaction; Described alkaline earth salt is a calcium chloride, bariumchloride, Manganous chloride tetrahydrate.
4. the preparation method of Nano red organic pigment according to claim 2, it is characterized in that: described diluted acid is dilute hydrochloric acid or dilute sulphuric acid.
5. the preparation method of Nano red organic pigment according to claim 2, it is characterized in that: 2B acid was 1: 3~20 with the mol ratio of diluted acid during described diazotization reaction was raw materials used, 2B acid is 1: 1~12 with the mol ratio of sodium hydroxide/potassium hydroxide, and 2B acid is 1: 1~1.8 with the mol ratio of Sodium Nitrite.
6. the preparation method of Nano red organic pigment according to claim 3, it is characterized in that: 2,3 acid were that 1: 1~3.5,2,3 sour mol ratios with sodium hydroxide/potassium hydroxide are 1: 1~7 with the mol ratio of calcium chloride during described coupled reaction was raw materials used.
7. the preparation method of Nano red organic pigment according to claim 1 is characterized in that: be 3~4 hours heat-up time during described vacuum-drying.
CNB2005100180753A 2005-09-30 2005-09-30 Method for preparing Nano red organic pigment Expired - Fee Related CN100363434C (en)

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CN101942217B (en) * 2010-07-28 2013-04-03 吴江市屯村颜料厂 Preparation method for special pigment for aqueous printing ink
CN102732054A (en) * 2012-05-29 2012-10-17 吴江市屯村颜料厂 Preparation method for 3119 light fast red BBS
CN103254661B (en) * 2013-05-14 2014-06-04 嘉兴科隆化工有限公司 Industrialized production method of transference-resistant blue light red pigment for PU (Poly Urethane)
CN104098923B (en) * 2014-07-25 2016-04-06 嘉兴科隆化工有限公司 A kind of machine side separates out industrialized preparing process and the machine side precipitation detection method thereof of few red
CN106634040A (en) * 2016-08-30 2017-05-10 上虞市东海化工有限公司 Preparation method of red pigment
CN111675922A (en) * 2020-06-22 2020-09-18 浙江东海新材料科技有限公司 Environment-friendly organic pigment applied to agricultural seed coating and preparation process thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1268532A (en) * 1999-03-24 2000-10-04 西巴特殊化学品控股有限公司 Compositions of azo lake pigment

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1268532A (en) * 1999-03-24 2000-10-04 西巴特殊化学品控股有限公司 Compositions of azo lake pigment

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C.I.颜料红48:2的改性. 吕东军,王世荣.化学工业与工程,第22卷第3期. 2005 *
C.I.颜料红57:1合成条件和改性的研究. 梁玉华,吕东军.应用化工,第31卷第1期. 2002 *

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