CN102346390B - Charge regulator and preparation method thereof, and carbon powder - Google Patents
Charge regulator and preparation method thereof, and carbon powder Download PDFInfo
- Publication number
- CN102346390B CN102346390B CN 201110333012 CN201110333012A CN102346390B CN 102346390 B CN102346390 B CN 102346390B CN 201110333012 CN201110333012 CN 201110333012 CN 201110333012 A CN201110333012 A CN 201110333012A CN 102346390 B CN102346390 B CN 102346390B
- Authority
- CN
- China
- Prior art keywords
- adjusting agent
- charge adjusting
- reaction
- charge
- carbon dust
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Abstract
The invention discloses a charge regulator and a preparation method thereof, and carbon powder, solving the problems of poor compatibility of the traditional charge regulator and resin, poor dispersibility, lower charge number and complex preparation process. A coupling, complexing and cation exchange one-pot method is adopted, intermediates related in the steps directly carry out the next step reaction in the same pot without separation, thus the process is simplified, and a pyrazolone azoic compound iron complex charge regulator with excellent charge performance, no influence by environment, good compatibility with the resin and environment friendliness is obtained. The carbon powder prepared by the charge regulator can obtain a high-quality image which is not influenced by environment factors.
Description
Technical field
The present invention relates to a kind of charge adjusting agent and preparation method thereof, and the electrostatic image development carbon dust that contains this charge adjusting agent.
Background technology
Along with making rapid progress of electrostatic image development technical development, more and more higher to the requirement of carbon dust, as the charge adjusting agent of one of important component part in the carbon dust, its performance directly affects the chargeding performance of carbon dust, and then affects the picture quality of electrostatic development.Except should having good charged characteristic, the charge adjusting agent of excellent performance also should have with carbon dust with the good compatibility of resin, namely has good dispersiveness in resin.If charge adjusting agent and resin can not be compatible well, cause disperseing inhomogeneous, or dispersive property is unstable, will have a strong impact on the speed that electrifies of carbon dust, chargeding performance and stability, thus affect the quality of image developing.
The charge adjusting agent that is widely used at present is mainly the azo-type metal complex class that salicylic acid type or aromatic carboxylic acid type metal complex class and central metal are chromium or iron.Salicylic acid type or aromatic carboxylic acid type metal complex class charge adjusting agent and carbon dust have good compatibility with resin, but find in actual applications, this class charge adjusting agent, affected by environment larger for the impact of carbon dust chargeding performance, cause thus the condition hypograph quality that changes at environment stable not; Central metal is the azo-type metal complex of chromium; although solved this problem; and has excellent chargeding performance; but because in recent years for the pay attention to day by day of global environmental protection problem; this class charge adjusting agent especially easily produces the hexavalent chromium compound that environment and human body all be harmful under the condition of burning in offal treatment, so and do not meet present requirement for the charge adjusting agent environment friendly.
Azo-type metallic iron complex compound charge adjusting agent has solved itself and carbon dust with the consistency problem of resin, does not also contain human body and the harmful heavy metal of environment.The carbon dust environment for use stability of utilizing such charge adjusting agent to make is significantly improved, and the electrostatic development image quality of carbon dust also improves, but because the carried charge of carbon dust is on the low side, does not reach comparatively ideal effect.And separate after azo-type metal complex charge adjusting agent adopts diazonium, coupling reaction usually, obtain intermediate and carry out also need separating after the complex reaction, carry out the method for kation conversion again, its complicated process of preparation, production cycle are long, have improved production cost.Even some technique has been used one kettle way, but it uses raw material different, and process conditions are also different, and charge adjusting agent NH
4 +The proportion requirement of occupying reach more than 60%, preparation condition is relatively harsh, cost is also higher, preparation stable bad.And this class charge adjusting agent drying is blocks of solid afterwards, and particle diameter is thicker, is difficult to reach by simple and mechanical fragmentation the particle diameter of expectation, must through jet-impingement pulverize or expensive mechanical treatment satisfying the particle diameter requirement, thereby further improved production cost.
Summary of the invention
The objective of the invention is in order to address the above problem, provide a kind of have excellent chargeding performance, not affected by environment, with tree refer to good, the environment amenable pyrazoline ketone of compatibility azo-compound iron complex charge adjusting agent.
Another object of the present invention provides a kind of manufacture method of above-mentioned charge adjusting agent, has advantages of that technique is simple, with short production cycle, cost is low.
The present invention also provides a kind of carbon dust that contains above-mentioned charge adjusting agent.
Pyrazoline ketone azo-compound iron complex charge adjusting agent is represented by following chemical formula (1):
Chemical formula (1)
In the formula, R is in the ortho position of pyrazolyl or contraposition, expression hydrogen or chlorine atom; X represents 1/3Fe
3+, A represents Na
+, B represents H
+, C represents NH
4 +, m+n+y+t=1.
The weight content of metallic iron element is 5.0-9.0% in the described charge adjusting agent, is preferably 6.0-7.5%; The weight content of sodium metal element is 0.1-2.5%, is preferably 0.3-1.0%.Control in the charge adjusting agent the metallic iron element and the weight content of sodium element be for complex reaction acquire a certain degree and kation in ferric ion and sodion reach certain ratio of occupying, thereby guarantee that charge adjusting agent has reasonable charged characteristic, and with resin reasonable compatibility is arranged with carbon dust.If the weight content of the metallic iron element in the charge adjusting agent and sodium element is high, then hydroscopicity is large, and is poor with the compatibility of flour-carbon resin, and the carbon dust carried charge is unstable, and the electrostatic development image quality is bad; If the weight content of the metallic iron element in the charge adjusting agent and sodium element is low, then complex reaction is bad, and wherein azo intermediate content is high, and the carried charge of charge adjusting agent is low, and corresponding carbon dust carried charge is low, causes the electrostatic development image quality bad.And because each cationic ratio of occupying in the charge adjusting agent is not necessarily wanted NH
4 +The ratio of occupying reach more than 60%, as long as metallic iron element and the weight percentage of sodium element controlled well wherein are just passable at claimed range.
The maximum absorption wavelength λ of described charge adjusting agent near ultraviolet-visible spectrum
MaxBe 390-410nm, be preferably 395-400nm.The maximum absorption wavelength λ of control charge adjusting agent near ultraviolet-visible spectrum
MaxBe in order to control wherein iron complex main content in suitable scope, thereby guarantee that charge adjusting agent has reasonable charged characteristic, and with resin good compatibility is arranged with carbon dust.Because the maximum absorption wavelength λ of the near ultraviolet-visible spectrum of azo-compound intermediate
MaxBe 419nm, and diazo salt decomposes the maximum absorption wavelength λ of the impurity near ultraviolet-visible spectrum that produces
MaxLess than 390nm, therefore as not controlling maximum absorption wavelength λ well
MaxIn suitable scope, illustrate that then diazo salt decomposes generation impurity many, perhaps complex reaction is bad, and azo intermediate content is higher in the charge adjusting agent, thereby affect charge adjusting agent charged characteristic and with carbon dust with the compatibility of resin, cause the electrostatic development image quality bad.
Described charge adjusting agent volume average particle size D50 is 0.2-20 μ m, is preferably 1-10 μ m.The volume average particle size D50 of control charge adjusting agent suitable scope be for guarantee charge adjusting agent have reasonable charged characteristic and with carbon dust with the good compatibility of resin.If the volume average particle size D50 of charge adjusting agent is too little, the charge adjusting agent particle is easily reunited, and disperses not open in resin at carbon dust, causes the carried charge of carbon dust low, and unstable.If the volume average particle size D50 of charge adjusting agent is too large, then the charge adjusting agent particle easily comes off from carbon powder particle, causes carbon dust carried charge deficiency and the internal contamination of electrostatic development machine, finally causes the electrostatic development image quality bad.
The preparation method of above-mentioned charge adjusting agent may further comprise the steps:
(1) first 2-amino-4-chlorophenol is joined in the acidic aqueous solution, under the sodium nitrite effect, carry out diazo reaction under the low temperature and form diazo salt, and then diazo salt joined carry out coupling reaction generation azo-compound intermediate reaction liquid in the alkaline aqueous solution that is formed by NaOH, sodium carbonate and pyrazolone derivative;
(2) directly in azo-compound intermediate reaction liquid, add solvent, NaOH, sodium carbonate, molysite, urea and ammonium chloride, in same pot, carry out complex reaction and cation exchange reaction;
(3) reaction product in the step (2) is separated, washing, drying and pulverization process make pyrazoline ketone azo-compound iron complex charge adjusting agent.
In the described step (2), first in azo-compound intermediate reaction liquid, add solvent, then add successively urea, molysite, add again NaOH and sodium carbonate and carry out complex reaction, react rear adding ammonium chloride and carried out cation exchange reaction, abundant to guarantee complex reaction, material particular diameter meets the requirements, and the weight percentage of metallic elements of ferrum and sodium meets the requirements.
Concrete technological reaction parameter can with reference to prior art, for example specifically be preferably:
In the described step (1), with respect to 1 mole of 2-amino-4-chlorophenol, the consumption of pyrazolone derivative is the 0.8-1.3 mole, the consumption of sodium nitrite is the 1-1.3 mole, the consumption of NaOH is the 0.8-1.2 mole, the consumption of sodium carbonate is the 0.2-0.5 mole, and the temperature of described diazo reaction is 0-20 ℃, and the temperature of described coupling reaction is 0-40 ℃.
In the described step (2), the temperature of reaction of complex reaction is 20-100 ℃; The reaction time of described cation exchange reaction is that 0.5-5 hour, temperature are 40-90 ℃.
In the described step (2), be equivalent to the 2-amino of 100 weight portions-4-chloro-phenol and add solvent 40-400 weight portion, NaOH 30-50 weight portion, sodium carbonate 10-30 weight portion, urea 20-100 weight portion, molysite 60-200 weight portion, ammonium chloride 4-60 weight portion.
Described pyrazolone derivative can exemplify out 3-methyl isophthalic acid-(4 '-chlorphenyl)-5-pyrazolone, 3-methyl isophthalic acid-(2 '-chlorphenyl)-5-pyrazolone, Edaravone etc.
Being as the criterion with reaction end of unreceipted reaction time in above-mentioned per step reaction generally is no more than 12 hours.
All have solvent to exist in the reaction system of coupling, complexing and cation exchange reaction, solvent is selected water and organic solvent mixed solution the best.As the organic solvent that forms this mixed solvent, can select hydrophilic organic solvent, preferentially select alcohols or glycols comparatively suitable, such as ethanol, propyl alcohol, isopropyl alcohol, butanols, ethylene glycol, propylene glycol etc., preferred normal butyl alcohol.
Described molysite can exemplify out use ferric trichloride, iron sulfate, ferric nitrate etc.
Through technique of the present invention, wash dried crude product and very easily pulverize, only need that the block crude product that drying forms is carried out the standard machinery pulverizing and just can reach the finished product grain size requirement, pulverize energy consumption low, and need not the crushing process of follow-up complexity.
Carbon dust of the present invention contains carbon dust resin, colorant and above-mentioned charge adjusting agent.Can also contain mould release, additive etc., for the carbon dust of 100 weight portions resin, contain 0.1-10 weight portion charge adjusting agent, the mould release of the colorant of 0.1-10 weight portion and 1-5 weight portion and the additive of 0.2-5 weight portion.
Wherein, carbon dust can use published resin with resin, such as styrene resin, acryl resin, and vibrin, silicones, polyamide, epoxy resin etc.; Colorant can be selected carbon black, magnetic, pigment or dyestuff etc.; Mould release can be selected low-molecular-weight polypropylene, low molecular weight polyethylene or wax, such as solid paraffin, microcrystalline wax and derivant thereof, Fischer-Tropsch wax and derivant thereof or polyolefin-wax and derivant thereof etc.; Additive comprises various inorganic particles, such as silicon dioxide, titania, alchlor etc.Here be not particularly limited.
Carbon dust preparation method of the present invention, except using pyrazoline ketone azo-compound iron complex charge adjusting agent of the present invention, the restriction that has nothing special can be used the common method of preparation carbon dust, such as conventional methods such as melting mixing comminuting method and polymerizations.
Beneficial effect:
1. charge adjusting agent of the present invention does not contain harmful heavy metal, simultaneously do not contain inflammable and explosive nitro, and the compatibility of this charge adjusting agent and resin is fine, can uniform and stable dispersion in resin, and this charge adjusting agent also has excellent chargeding performance simultaneously.
2. each cationic ratio of occupying in the charge adjusting agent is not necessarily wanted NH
4 +The ratio of occupying reach more than 60% (general azo-type metallic iron complex compound charge adjusting agent NH
4 +The proportion requirement of occupying reach more than 60%), as long as metallic iron element and the weight percentage of sodium element controlled well wherein are just passable at claimed range, so that the technique of charge adjusting agent is more easily controlled.And adopt coupling, complexing, cation exchange one kettle way, these several steps, related intermediate all directly carried out next step reaction without separation in same pot, thereby simplified technological process, greatly shortened the production cycle, production cost and labour intensity have been reduced, avoided the loss of material that causes because of separating for several times washing intermediate and the waste of water, thereby reduced the discharging of the three wastes, and guaranteed that product has higher yield.
3. contain in the carbon dust of the present invention and possess the charged adjusting function of above-mentioned excellence and the good charge adjusting agent of resin compatible, use this carbon dust can obtain not to be subjected to the high quality graphic of such environmental effects, can not occur the carbon dust that the carried charge inequality because of carbon dust causes when the excellent carbon dust that plays electrical characteristics forms image under high print speed yet and disperse and the bottom ash phenomenon even have, can obtain high quality graphic.
Embodiment
Charge adjusting agent embodiment 1
In the 500mL there-necked flask, add 15.0g 37% hydrochloric acid, 80mL water and 10g 2-amino-4-chlorophenol, stirring and dissolving, then be cooled to 0-5 ℃, slowly drip the aqueous solution that the 5g sodium nitrite is dissolved in 20mL, continue stirring reaction 0-5 ℃ of insulation after dripping off and obtained diazonium salt solution in 1.5 hours.In the 500mL there-necked flask, add 100mL water, 3.0g NaOH, 2.5g sodium carbonate, stirring and dissolving adds 14.6g 3-methyl isophthalic acid-(4 '-chlorphenyl)-5-pyrazolone, and stirring and dissolving is cooled to 0-5 ℃.Diazonium salt solution is slowly splashed in the above-mentioned coupling component solution, continue reaction 2 hours to diazo salt 0-5 ℃ of insulation after dripping off and disappear.In above-mentioned reactant liquor, add first the 20mL normal butyl alcohol, then add 10g urea, slowly splash into again the aqueous solution that the 8.4g ferric trichloride is dissolved in 40mL, splash into again the aqueous solution that 4g NaOH and 2.6g sodium carbonate are dissolved in 30mL, after dropwising, be warming up to 90 ℃ of back flow reaction and be cooled to 80 ℃ after 3 hours, add 2g ammonium chloride reaction 2 hours, be cooled to afterwards 60 ℃, then through separation, washing, dry, mechanical crushing, obtain 26.5g black powder shape charge adjusting agent finished product (I).Its structure represents with chemical formula (2).
(X represents 1/3Fe
3+, A represents Na
+, B represents H
+, C represents NH
4 +, m+n+y+t=1)
Charge adjusting agent embodiment 2
Change 3-methyl isophthalic acid used in the coupling operation among the embodiment 1-(4 '-chlorphenyl)-5-pyrazolone into 3-methyl isophthalic acid-(2 '-chlorphenyl)-5-pyrazolone, in addition other operations in the same manner as in Example 1, obtain the charge adjusting agent finished product (II) of embodiment 2, its structure represents with chemical formula (3).
(X represents 1/3Fe
3+, A represents Na
+, B represents H
+, C represents NH
4 +, m+n+y+t=1)
Charge adjusting agent embodiment 3
Change 3-methyl isophthalic acid used in the coupling operation among the embodiment 1-(4 '-chlorphenyl)-5-pyrazolone into the 13.6g Edaravone, in addition other operations in the same manner as in Example 1, obtain the charge adjusting agent finished product (III) of embodiment 3, its structure represents with chemical formula (4).
(X represents 1/3Fe
3+, A represents Na
+, B represents H
+, C represents NH
4 +, m+n+y+t=1)
Charge adjusting agent embodiment 4
Change the amount of ferric trichloride used in the complexing operation among the embodiment 1 into 6.3g from 8.4g, in addition other operations obtain the charge adjusting agent finished product (IV) of embodiment 4, the same chemical formula of its structure (2) in the same manner as in Example 1.
Charge adjusting agent embodiment 5
Change the use amount of the ammonium chloride among the embodiment 1 into 1g from 2g, in addition other operations obtain the charge adjusting agent finished product (V) of embodiment 5, the same chemical formula of its structure (2) in the same manner as in Example 1.
Charge adjusting agent embodiment 6
Change the use amount of the ammonium chloride among the embodiment 1 into 3g from 2g, in addition other operations obtain the charge adjusting agent finished product (VI) of embodiment 6, the same chemical formula of its structure (2) in the same manner as in Example 1.
Charge adjusting agent embodiment 7
Change the use amount of the urea among the embodiment 1 into 6.5g from 10g, in addition other operations obtain the charge adjusting agent finished product (VII) of embodiment 7, the same chemical formula of its structure (2) in the same manner as in Example 1.
Charge adjusting agent embodiment 8
Change the use amount of the ammonium chloride among the embodiment 1 into 3g from 2g, simultaneously, change the use amount of urea into 6.5g from 10g, in addition other operations in the same manner as in Example 1, obtain the charge adjusting agent finished product (VIII) of embodiment 8, the same chemical formula of its structure (2).
Charge adjusting agent comparative example 1
Be down to 0-5 ℃ after in the 500mL there-necked flask, adding 190mL water, 25g 37% hydrochloric acid, 14.4g 2-amino-4-chlorophenol, stirring and dissolving, drip 20g 36% sodium nitrite solution, control simultaneously temperature and be not higher than 5 ℃.After dripping, sodium nitrite solution after 0-5 ℃ of insulation reaction 1-2 hour, obtains diazonium salt solution.In the 1000mL there-necked flask, add 165mL water, 30g 20% sodium hydroxide solution, 26.3g azoic coupling component AS, be cooled to 0-5 ℃ after the stirring and dissolving, then add fast the completely reacted diazo salt in front, react 3-5 hour to the diazo salt disappearance at 5-10 ℃ afterwards, obtain reacting conjugates solution.In coupling solution, add 100mL methyl alcohol, 30g 20% NaOH, 2.8g ammonium chloride and 15g urea, drip afterwards 40.6g 20% liquor ferri trichloridi, be warming up to 70oC after dripping, back flow reaction is down to below 60 ℃ after 2.5 hours, then separate, washing, drying, air-flow crushing obtains 42.5g black powdery charge adjusting agent finished product (IX), and its structure represents with chemical formula (5):
(X
1 +Expression NH
4 +, H
+, Na
+Ion or three's mixture)
Charge adjusting agent comparative example 2
In the 500mL there-necked flask, add 190mL water, 25g 37% hydrochloric acid, 14.4g 2-amino-4-chloro-phenol, be down to 0-5 ℃ after the stirring and dissolving, drip 20g 36% sodium nitrite solution, control simultaneously temperature and be not higher than 5 ℃.After dripping, sodium nitrite solution obtains diazonium salt solution 0-5 ℃ of insulation reaction after 12 hours.In the 1000mL there-necked flask, add 165mL water, 30g 20% sodium hydroxide solution, 29.3g Naphthol AS-OL, be cooled to 0-5 ℃ after the stirring and dissolving, then add fast the completely reacted diazo salt in front, react 3-5 hour to the diazo salt disappearance at 5-10 ℃ afterwards, obtain reacting conjugates solution.In conjugates solution, add 100mL methyl alcohol, 30g 20% NaOH, 2.8g ammonium chloride and 15g urea, drip afterwards 40.6g 20% liquor ferri trichloridi, be warming up to 70 ℃ after dripping, back flow reaction is down to below 60 ℃ after 2.5 hours, then separate, wash, dry, air-flow crushing, obtain 41.7g black powdery charge adjusting agent finished product (X), its structure represents with chemical formula (6):
(X
2 +Expression NH
4 +, H
+, Na
+Ion or three's mixture)
The weight content of metallic iron element and sodium element is measured with x-ray fluorescence analysis device (such as XRF-1800) in the charge adjusting agent finished product of the present invention; The maximum absorption wavelength λ of near ultraviolet-visible spectrum
MaxMeasure with ultraviolet-visible pectrophotometer (such as TU-1810); Volume average particle size D50 measures with laser diffraction granularity tester (such as COULTER LS230); Carbon powder for development of static charge volume average particle size of the present invention is measured with electric-resistivity method particle size analyzer (such as Beckman-product MULTISIZER-3 of Coulter Corporation).
Electrostatic image development of the present invention is measured with body of powder electrification amount determining device (such as TB-203) with the carried charge of carbon dust.
The carbon dust preparation example:
The method for preparing carbon dust with the embodiment of the invention and comparative example charge adjusting agent finished product is: the charge adjusting agent finished product is used respectively the styrene-propene acid copolymer resin, carbon black and paraffin are according to 93 parts of resins of weight ratio, 5 parts of carbon blacks, 1 part of paraffin and 1 part of charge adjusting agent carry out proportioning, fully mix, then heating and melting is mixing, cool off again and the process crushing and classification, obtain volume average particle size and be 8 microns electronegative property carbon dust parent, then, add the number average particle diameter 12nm of 0.8 weight portion in the carbon dust parent of 100 weight portions, hydrophobic deg is 67 hydrophobic silica, and mix with Henschel mixer, obtained electronegative property carbon dust.
Be that 90-130 micron iron powder carrier is mixed to get the electrostatic development developer by weight 3/97 with carbon dust and diameter again.
Use embodiment 1-8 and the resulting charge adjusting agent finished product of comparative example 1-2 to prepare respectively carbon powder for development of static charge and developer by above-mentioned carbon dust and developer preparation method.The developer that obtains carbon dust 1-8 and relatively carbon dust 1-2 preparation is duplicated 5000 continuously in duplicating machine, measure the carbon dust carried charge and test the copy effect that to obtain the result as shown in table 2.
It is as shown in the table for every testing result of each embodiment of table 1 and comparative example charge adjusting agent finished product:
It is as shown in the table with the evaluation result that compares carbon dust for each carbon dust of table 2:
Claims (6)
1. pyrazoline ketone azo-compound iron complex charge adjusting agent is represented by following chemical formula (1):
In the formula, R is in the ortho position of pyrazolyl or contraposition, expression hydrogen or chlorine atom; X represents 1/3Fe
3+, A represents Na
+, B represents H
+, C represents NH
4 +, m+n+y+t=1, the weight content of metallic iron element is 5.0-9.0 % in the described charge adjusting agent; The weight content of sodium metal element is 0.1-2.5 %.
2. charge adjusting agent as claimed in claim 1 is characterized in that, the maximum absorption wavelength λ of described charge adjusting agent near ultraviolet-visible spectrum
MaxBe 390-410nm.
3. charge adjusting agent as claimed in claim 1 is characterized in that, described charge adjusting agent volume average particle size D50 is 0.2-20 μ m.
4. the preparation method of each charge adjusting agent among the claim 1-3 is characterized in that, may further comprise the steps:
(1) first 2-amino-4-chlorophenol is joined in the acidic aqueous solution, under the sodium nitrite effect, carry out diazo reaction under the low temperature and form diazo salt, then diazo salt is joined again and carry out coupling reaction generation azo-compound intermediate reaction liquid in the alkaline aqueous solution that is formed by NaOH, sodium carbonate and pyrazolone derivative;
(2) directly in azo-compound intermediate reaction liquid, add solvent, NaOH, sodium carbonate, molysite, urea and inorganic ammonium salt, in same pot, carry out complex reaction and cation exchange reaction, be specially and in azo-compound intermediate reaction liquid, add solvent first, then add successively urea, molysite, add again NaOH and sodium carbonate and carry out complex reaction, reacted rear adding ammonium chloride and carried out cation exchange reaction.
(3) reaction product in the step (2) is separated, washing, drying and pulverization process make pyrazoline ketone azo-compound iron complex charge adjusting agent.
5. preparation method as claimed in claim 4 is characterized in that, described solvent is normal butyl alcohol.
6. an electrostatic image development carbon dust is characterized in that, contains each charge adjusting agent among carbon dust resin, colorant, mould release, additive and the claim 1-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110333012 CN102346390B (en) | 2011-10-28 | 2011-10-28 | Charge regulator and preparation method thereof, and carbon powder |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110333012 CN102346390B (en) | 2011-10-28 | 2011-10-28 | Charge regulator and preparation method thereof, and carbon powder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102346390A CN102346390A (en) | 2012-02-08 |
| CN102346390B true CN102346390B (en) | 2013-05-01 |
Family
ID=45545185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201110333012 Active CN102346390B (en) | 2011-10-28 | 2011-10-28 | Charge regulator and preparation method thereof, and carbon powder |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102346390B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6720196B2 (en) * | 2015-09-17 | 2020-07-08 | 保土谷化学工業株式会社 | Charge control agent and toner using pyrazolone derivative or salt of the derivative |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0841596A1 (en) * | 1996-11-11 | 1998-05-13 | Canon Kabushiki Kaisha | Non-magnetic toner for developing electrostatic image, process for producing non-magnetic toner particles, and image forming method |
| CN1645261A (en) * | 2005-01-20 | 2005-07-27 | 湖北鼎龙化工有限责任公司 | Production of electric charge regulator and carbon powder containing it for electronic camera |
| CN1759102A (en) * | 2003-03-31 | 2006-04-12 | 保土谷化学工业株式会社 | Monoazo iron complex compound, charge control agent containing the same, and toner |
| CN101387836A (en) * | 2008-10-23 | 2009-03-18 | 湖北鼎龙化学股份有限公司 | Method for preparing electronic charge regulating agent and carbon powder |
| CN101630129A (en) * | 2009-08-05 | 2010-01-20 | 湖北鼎龙化学股份有限公司 | Azo series charge regulator dispersoid and preparation method thereof and carbon powder |
-
2011
- 2011-10-28 CN CN 201110333012 patent/CN102346390B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0841596A1 (en) * | 1996-11-11 | 1998-05-13 | Canon Kabushiki Kaisha | Non-magnetic toner for developing electrostatic image, process for producing non-magnetic toner particles, and image forming method |
| CN1759102A (en) * | 2003-03-31 | 2006-04-12 | 保土谷化学工业株式会社 | Monoazo iron complex compound, charge control agent containing the same, and toner |
| CN1645261A (en) * | 2005-01-20 | 2005-07-27 | 湖北鼎龙化工有限责任公司 | Production of electric charge regulator and carbon powder containing it for electronic camera |
| CN101387836A (en) * | 2008-10-23 | 2009-03-18 | 湖北鼎龙化学股份有限公司 | Method for preparing electronic charge regulating agent and carbon powder |
| CN101630129A (en) * | 2009-08-05 | 2010-01-20 | 湖北鼎龙化学股份有限公司 | Azo series charge regulator dispersoid and preparation method thereof and carbon powder |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102346390A (en) | 2012-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104583877B (en) | Toner | |
| KR101548564B1 (en) | Azo pigment composition, process for production of the composition, dispersions containing the composition, colored compositions and jet printing ink | |
| CN1715338B (en) | Azobalbituric acid metal complex pigment and process for the production thereof | |
| CN103717680B (en) | Comprise azo pigment, coloured composition, ink-jet recording ink dispersion and prepare the method for dispersion | |
| WO2008069045A1 (en) | Dye compound, and yellow toner comprising the dye compound | |
| TW455618B (en) | Yellow pigment compositions and the process thereof | |
| JPS6342672B2 (en) | ||
| CN102346390B (en) | Charge regulator and preparation method thereof, and carbon powder | |
| CN1323330C (en) | Production of electric charge regulator and carbon powder containing it for electronic camera | |
| CN105541674A (en) | Compound and preparing method thereof, and application of compound in dye | |
| DE10016547A1 (en) | Continuous manufacturing process for metal complex pigments | |
| TWI596162B (en) | Process for producing a charge control agent | |
| US8076465B2 (en) | Method for manufacturing charge control agent | |
| JPS63178169A (en) | Disazo pigment composition | |
| KR100827041B1 (en) | Laked monoazo pigments based on naphtholsulfonic acids | |
| JP2005516103A (en) | Mono or bisazo copper complex dye | |
| CN100421032C (en) | Charge regulator and its preparing method and carbon powder for containing same charge regulator | |
| CN106397465B (en) | Azo metal complex and its charge control agent application and the toner containing it | |
| JPH07117776B2 (en) | Positively charged toner | |
| CN101630129B (en) | Azo series charge regulator dispersoid and preparation method thereof and carbon powder | |
| CN107254191A (en) | A kind of azo bivalent metallic ion complex and its purposes in toner | |
| JPS5821937B2 (en) | Manufacturing method of azo lake pigment | |
| JP5818757B2 (en) | Toner for developing electrostatic image and method for producing toner for developing electrostatic image | |
| JP4310819B2 (en) | Novel pigment and method for producing the same | |
| JP2001261995A (en) | Method for producing green pigment composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C56 | Change in the name or address of the patentee | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 430015 Hubei city of Wuhan province Hankou Jianghan Road No. 8 Jinmao Building 19 Patentee after: Hubei Dinglong Cmi Holdings Ltd Address before: 430015 Hubei city of Wuhan province Hankou Jianghan Road No. 8 Jinmao Building 19 Patentee before: Hubei Dinglong Chemical Co., Ltd. |