CN100346235C - Novel zirconium compound charge regulator and carbon powder for electro photography containing same charge regulator - Google Patents
Novel zirconium compound charge regulator and carbon powder for electro photography containing same charge regulator Download PDFInfo
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- CN100346235C CN100346235C CNB2005100193749A CN200510019374A CN100346235C CN 100346235 C CN100346235 C CN 100346235C CN B2005100193749 A CNB2005100193749 A CN B2005100193749A CN 200510019374 A CN200510019374 A CN 200510019374A CN 100346235 C CN100346235 C CN 100346235C
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- charge regulator
- adjusting agent
- charge
- carbon powder
- zirconium compound
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Abstract
The present invention provides a novel zirconium compound charge regulator and carbon powder for electro photography containing the charge regulator. A zirconium compound is the form, wherein x represents a whole number of one to three. The zirconium compound of the form with the average particle diameter of 0.1 micrometer to 15 micrometers is used as the charge regulator for the electro photography carbon powder. The zirconium compound charge regulator has the advantages of stable chemical property, difficult oxidation and discoloring, strong resin affinity and good dispersivity in resin. The carbon powder for electro photography containing the charge regulator has high electrification speed, and can not generate problems, such as electrical quantity attenuation, image quality descending, etc., due to long time and adverse environment.
Description
Technical field
The present invention relates to a kind of zirconium compound charge regulator and contain the carbon powder for electro photography of this charge adjusting agent.
Background technology
The general carbon dust that uses in duplicating machine or electrostatic recording apparatus is made of binder resin, colorant, charge adjusting agent and other adjuvants, in order to obtain desired charged characteristic, ageing stability, environmental stability, charge adjusting agent has played irreplaceable effect in carbon dust.
From now on, along with the expansion in colored carbon powder market, people will wish to use in colored carbon powder a kind of material colourless or light color to use as charge adjusting agent.About the colourless or light color charge adjusting agent that in carbon powder for electro photography, uses a lot of motions were arranged in the past, system contains chromium compound (No. 4206064, United States Patent (USP)) such as salicylic acid, salicylic acid is zinc compound (No. 4656112, a United States Patent (USP)), quaternary ammonium salt compound (Jap.P. goes out to be willing to flat 1-54694 number), salicylic acid is a boron-containing compound (Jap.P. goes out to be willing to flat 7-104620) etc.
But, all having the charged effect deficiency of giving based on the charge adjusting agent of above-mentioned technology, shortcoming such as environmental stability is good does not inadequately have perfect performance as yet as charge adjusting agent.
It is zirconium-containing compound that other colourless or light color charge adjusting agent also has salicylic acid, as: Chinese patent disclose 1237182, Jap.P. discloses 2002278162, Jap.P. discloses 2001249500, Jap.P. discloses 2003262988 etc.Charge adjusting agent based on these technology belongs to the aromatic series hydroxy-containing compounds, though have high triboelectric charge, because hydroxyl is more in the molecular structure, oxidation stain and rotten is difficult to guarantee product quality stability easily.
Summary of the invention
One of purpose of the present invention is: solve the unresolved problem that above-mentioned technology exists, the novel zirconium compound charge regulator that chargeding performance is outstanding, be not subjected to the light color of continuously long-time use and temperature, humidity effect is provided; Two of purpose of the present invention provides a kind of carbon powder for electro photography that contains this charge adjusting agent, high-performance carbon dust that promptly can high resolution image steady in a long-term.
Technical solution of the present invention: a kind of with the represented zirconium compounds of following structural (1):
... ... chemical formula (1)
In the formula: x represents 1～3 integer.
A kind of carbon powder for electro photography, with carbon dust by the described novel zirconium compound of chemical formula (1) as charge adjusting agent.
The advantage of invention:
The present invention is a kind of white powder compound by the novel zirconium-containing compound charge adjusting agent of chemical formula (1) expression, and chemical property is stable, is difficult for oxidation and variable color, and is strong with resin affinity, good dispersion in resin.This charge adjusting agent result of use in carbon powder for electro photography is outstanding, fully has the various functions as charge adjusting agent.
The carbon dust chargeding performance that contains charge adjusting agent of the present invention is good, and has splendid environmental stability.This kind carbon dust speed that electrifies is fast, even long-time continuous is used and degradation problem under carried charge decay and the image quality can not take place yet using under hot and humid and the low temperature and low humidity environment.Carry out the electronics development with this kind carbon dust and can obtain distinct developed image.
Embodiment
Find chemical formula (1) through concentrating on studies
(in the formula: x represents 1～3 integer.)
The zirconium-containing compound of expression is a kind of white, stable compound, and it has good dispersiveness in various kinds of resin, and can give outstanding chargeding performance of carbon powder for electro photography and environmental stability, is a kind of good carbon dust charge adjusting agent.
That is to say that the present invention can provide the novel zirconium-containing compound charge adjusting agent by following formula (1) expression, and the carbon powder for electro photography that contains this charge adjusting agent.
Carbon powder for electro photography of the present invention is the zirconium-containing compound charge adjusting agent formation by bonding agent-resin, colorant (pigment, dyestuff or magnetic) and chemical formula (1) expression basically.
Bonding agent-resin comprises polystyrene, styrene-propene acid based copolymer, vibrin, epoxy resin etc., and these resins can use separately also can mix use.
Black carbon powder uses colorant carbon black commonly used.
Colored carbon powder uses colorant such as inorganic pigment, organic pigment and oil-soluble dyes etc. commonly used in the carbon dust production.
Above Fa Ming novel zirconium-containing compound charge adjusting agent, its mean grain size has good dispersiveness in various kinds of resin between the 0.1-8 micron.In carbon dust,, comprise this kind of 0.05-8 weight portion compound charge adjusting agent corresponding to 100 parts by weight resin.
Embodiment 1: the chemical constitution of charge adjusting agent can be represented with following formula in this example.
... ... chemical formula (1-1)
Chemical formula (1-1) zirconium-containing compound charge adjusting agent method for making is as follows:
1, in the 500ml there-necked flask, adds 300ml water, stir adding 49g hydration zirconium oxychloride (ZrOCl down
28H
2O), stirring and dissolving becomes transparency liquid under the room temperature;
2, in the 1000ml there-necked flask, add 600ml water, add 34g 20% sodium hydrate aqueous solution, open and stir back adding 46.5g 3,5-di-t-butyl-2-Hydroxyphenyl Acetic Acid, being warmed up to 60-70 ℃, to be dissolved to solution transparent, add 34g 20% sodium hydrate aqueous solution again, be warming up to 95-98 ℃ of reaction after 1 hour, be cooled to 60-70 ℃;
3, step 1 gained hydration zirconium oxychloride aqueous solution is added drop-wise in the solution of step 2 gained, drips off control temperature in back in 1 hour, and the pH of control reactant liquor is 7.5-8.5, finish to reaction 60-70 ℃ of reaction 3 hours;
4, filter, wash after having reacted, wet cake under 50-80 ℃, carry out vacuum drying to moisture less than 1%, white powdery dry product 67.1g, siccative is carried out mechanical crushing to mean grain size D
50=4.95 μ m promptly get charge adjusting agent.
This charge adjusting agent being placed in 25 ℃ of air observe outward appearance and change color after 24 hours, still is white powder.
The carbon powder for electro photography method for making that contains this charge adjusting agent is as follows:
With this charge adjusting agent with styrene acrylic resin and carbon black according to mass unit 100 portions of resin 6 carbon blacks: 1 charge adjusting agent carries out proportioning, after fully mixing, heating and melting is mixing, and the airflow pulverization method crushing and classification is used in cooling back, obtains volume average particle size and be 8 microns carbon dust.
According to 5: 95 weight ratio, mix this carbon dust and iron powder carrier then, make developer.
Use standard air blast detects this developer carried charge, carried charge is-25.4 μ C/g (25 ℃, 50%) under the general condition, under low temperature and low humidity (5 ℃, 30%) and hot and humid (60 ℃, 90%) condition, record carried charge and be respectively-25.2 μ C/g and-25.8 μ C/g, carried charge is highly stable.
After using this developer to duplicate 10,000 continuously in duplicating machine, measuring the carbon dust carried charge is-24.8 μ C/g (25 ℃, 50%), and it is very distinct to duplicate the image that obtains, and the phenomenon that quality descends do not occur.
Embodiment 2:
The chemical constitution of charge adjusting agent can be represented with following formula in this example:
... ... chemical formula (1-2)
Chemical formula (1-2) zirconium compound charge regulator method for making is as follows:
1, in the 500ml there-necked flask, adds 300ml water, stir adding 49g hydration zirconium oxychloride (ZrOCl down
28H
2O), stirring and dissolving becomes transparency liquid under the room temperature.
2, in the 1000ml there-necked flask, add 600ml water, add 34g 20% sodium hydrate aqueous solution, open and stir back adding 50g 3,5-di-t-butyl-2-hydroxy phenylpropionic acid, being warmed up to 60-70 ℃, to be dissolved to solution transparent, add 34g 20% sodium hydrate aqueous solution again, be warming up to 95-98 ℃ of reaction after 1 hour, be cooled to 60-70 ℃;
3, rapid 1 gained hydration zirconium oxychloride aqueous solution is added drop-wise in the solution of step 2 gained, drips off control temperature in back in 1 hour, and the pH of control reactant liquor is 7.5-8.5, finish to reaction 60-70 ℃ of reaction 3 hours;
4, filter, wash after having reacted, wet cake under 50-80 ℃, carry out vacuum drying to moisture less than 1%, white powdery dry product 70g, siccative is carried out mechanical crushing to mean grain size D
50=4.95 μ m promptly get charge adjusting agent.This charge adjusting agent being placed in 25 ℃ of air observe outward appearance and change color after 24 hours, still is white powder.
The carbon powder for electro photography method for making that contains this charge adjusting agent is as follows:
With this charge adjusting agent with styrene acrylic resin and carbon black according to mass unit 100 portions of resin 6 carbon blacks: 1 charge adjusting agent carries out proportioning, after fully mixing, heating and melting is mixing, and the airflow pulverization method crushing and classification is used in cooling back, obtains volume average particle size and be 8 microns carbon dust.
According to 5: 95 weight ratio, mix this carbon dust and iron powder carrier then, make developer.
Detect this developer carried charge with the standard air blast, carried charge is-20.8 μ C/g (25 ℃, 50%) under the general condition, under low temperature and low humidity (5 ℃, 30%) and hot and humid (60 ℃, 90%) condition, record carried charge and be respectively-21.6 μ C/g and-20.5 μ C/g, carried charge is highly stable.
After using this developer to duplicate 10,000 continuously in duplicating machine, measuring the carbon dust carried charge is-21.0 μ C/g (25 ℃, 50%), and it is very distinct to duplicate the image that obtains, and the phenomenon that quality descends do not occur.
Embodiment 3
The chemical constitution of charge adjusting agent can be represented with following formula in this example.
... ... chemical formula (1-3)
Chemical formula (1-3) zirconium compound charge regulator method for making is as follows:
1, adds 300ml water in the 500ml there-necked flask, stir adding 49g hydration zirconium oxychloride (ZrOCl down
28H
2O), stirring and dissolving becomes transparency liquid under the room temperature.
2, in the 1000ml there-necked flask, add 600ml water, add 34g 20% sodium hydrate aqueous solution, open and stir back adding 51.4g 3,5-di-t-butyl-2-hydroxy benzenes butyric acid, being warmed up to 60-70 ℃, to be dissolved to solution transparent, adds 34g 20% sodium hydrate aqueous solution again, is warming up to 95-98 ℃ of reaction after 1 hour, be cooled to 60-70 ℃, toward wherein dripping zirconium oxychloride aqueous solution;
3, rapid 1 gained hydration zirconium oxychloride aqueous solution is added drop-wise in the solution of step 2 gained, drips off control temperature in back in 1 hour, and the pH of control reactant liquor is 7.5-8.5, finish to reaction 60-70 ℃ of reaction 3 hours;
4, filter, wash after having reacted, wet cake under 50-80 ℃, carry out vacuum drying to moisture less than 1%, white powdery dry product 72.8g, siccative is carried out mechanical crushing to mean grain size D
50=4.95 μ m promptly get charge adjusting agent.This charge adjusting agent being placed in 25 ℃ of air observe outward appearance and change color after 24 hours, still is white powder.
The carbon powder for electro photography method for making that contains this charge adjusting agent is as follows:
With this charge adjusting agent with styrene acrylic resin and carbon black according to mass unit 100 portions of resin 6 carbon blacks: 1 charge adjusting agent carries out proportioning, after fully mixing, heating and melting is mixing, and the airflow pulverization method crushing and classification is used in cooling back, obtains volume average particle size and be 8 microns carbon dust.According to 5: 95 weight ratio, mix this carbon dust and iron powder carrier then, make developer.
Detect this developer carried charge with the standard air blast, carried charge is-23.2 μ C/g (25 ℃, 50%) under the general condition, under low temperature and low humidity (5 ℃, 30%) and hot and humid (60 ℃, 90%) condition, record carried charge and be respectively-23.4 μ C/g and-23.8 μ C/g, carried charge is highly stable.
After using this developer to duplicate 10,000 continuously in duplicating machine, measuring the carbon dust carried charge is-18.3 μ C/g (25 ℃, 50%), and it is very distinct to duplicate the image that obtains, and the phenomenon that quality descends do not occur.
Comparative example 1:
Add 200ml water, 7.2g zinc chloride in the 500ml there-necked flask, stirring and dissolving becomes transparency liquid.In the 1000ml there-necked flask, add 200ml water, 4.0g NaOH, 25g3, the 5-di-tert-butyl salicylic acid, open to stir and be warmed up to 60-70 dissolving 1 hour to becoming clear solution, then solder(ing)acid is added drop-wise to 3, in the 5-di-tert-butyl salicylic acid aqueous solution, be warmed up to 70-80 reaction 3 hours, the pH of control reaction simultaneously is 6.0-7.0.Filter after having reacted, wash, dry, pulverize 28g white powdery 3,5-di-tert-butyl zinc salicylate charge adjusting agent.
Then with this charge adjusting agent with styrene acrylic resin and carbon black according to mass unit 100 portions of resin 6 carbon blacks: 1 charge adjusting agent carries out proportioning, after fully mixing, heating and melting is mixing, and the usual method crushing and classification is used in cooling back, obtains volume average particle size and be 8 microns carbon dust.According to 5: 95 weight ratio, mix this carbon dust and iron powder carrier then, make developer.
Detect this developer carried charge with the standard air blast, carried charge is-19.5 μ C/g (25 ℃, 50%) under the general condition, under low temperature and low humidity (5 ℃, 30%) and hot and humid condition (60 ℃, 90%), record carried charge and be respectively-18.2 μ C/g and-16.1 μ C/g, under hot and humid condition, carried charge takes place obviously to reduce.
After using this developer to duplicate 10,000 continuously in duplicating machine, measuring the carbon dust carried charge is-15.7 μ C/g (25 ℃, 50%), duplicates the image that obtains and finds obvious bottom ash, compares with duplicating the initial stage image, and image quality declines to a great extent.
Comparative example 2:
Add 100ml water, 6g lime chloride in the 250ml there-necked flask, stirring and dissolving becomes transparency liquid.In the 1000ml there-necked flask, add 500ml water, 4.0g NaOH, 25g3,5-di-tert-butyl salicylic acid, stirring are warmed up to the 60-70 dissolving and are cooled to 30 after 1 hour, drip calcium chloride water, 30-40 reaction 3 hours, the pH of control reaction simultaneously was 6.0～7.0 afterwards.Filter after having reacted, wash, dry, pulverize 26g white powdery 3,5-di-tert-butyl salicylic acid calcium charge adjusting agent.
Then with this charge adjusting agent with styrene acrylic resin and carbon black according to mass unit 100 portions of resin 6 carbon blacks: 1 charge adjusting agent carries out proportioning, after fully mixing, heating and melting is mixing, and the usual method crushing and classification is used in cooling back, obtains volume average particle size and be 8 microns carbon dust.According to 5: 95 weight ratio, mix this carbon dust and iron powder carrier then, make developer.
Detect this developer carried charge with the standard air blast, carried charge is-16.3 μ C/g (25 ℃, 50%) under the general condition, under low temperature and low humidity (5 ℃, 30%) and hot and humid (60 ℃, 90%) condition, record carried charge and be respectively-15.8 μ C/g and-12.1 μ C/g, under hot and humid condition, carried charge takes place obviously to reduce.
After using this developer to duplicate 10,000 continuously in duplicating machine, measuring the carbon dust carried charge is-11.8 μ C/g (25 ℃, 50%), and it is obviously not enough to duplicate the image blackness that obtains, and compares with duplicating the initial stage image, and image quality declines to a great extent.
Comparative example 3:
In the 500ml there-necked flask, add 300ml water, stir adding 49g hydration zirconium oxychloride (ZrOCl down
28H
2O), stirring and dissolving becomes transparency liquid under the room temperature.
In the 1000ml there-necked flask, add 600ml water, add 34g 20% sodium hydrate aqueous solution, open and stir back adding 45.5g 3, the 5-di-tert-butyl salicylic acid, be warming up to 60-70 ℃ and be dissolved to clear solution, toward wherein dripping zirconium oxychloride aqueous solution, dripped off back control temperature in 1 hour 60-70 ℃ of reaction 3 hours, and the pH of control reaction is 6.0-7.0.Filter after having reacted, wash, dry, pulverize 61.4g white powdery charge adjusting agent.This charge adjusting agent placed in 25 ℃ of air observe outward appearance and color after 24 hours, find to become sulphur toner end, illustrate that the oxidation stain reaction has taken place this charge adjusting agent in air.
Found that of contrast the various embodiments described above and comparative example, the zirconium-containing compound charge adjusting agent chemical property of chemical formula (1) expression is stable, and result of use is outstanding in carbon powder for electro photography, fully has the various functions as charge adjusting agent.The carbon dust chargeding performance that contains this charge adjusting agent is good, and has splendid environmental stability.
Claims (2)
1. zirconium compound charge regulator, represent with following structural (1):
Chemical formula (1)
In the formula: x represents 1～3 integer.
2. carbon powder for electro photography, it is characterized in that described carbon powder for electro photography by the described zirconium compounds of claim 1 as charge adjusting agent.
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| CNB2005100193749A CN100346235C (en) | 2005-08-31 | 2005-08-31 | Novel zirconium compound charge regulator and carbon powder for electro photography containing same charge regulator |
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| CNB2005100193749A CN100346235C (en) | 2005-08-31 | 2005-08-31 | Novel zirconium compound charge regulator and carbon powder for electro photography containing same charge regulator |
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| CN100346235C true CN100346235C (en) | 2007-10-31 |
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| CN100483263C (en) * | 2007-04-19 | 2009-04-29 | 湖北鼎龙化学股份有限公司 | Electric charge regulator and carbon powder |
Citations (8)
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| CN1237182A (en) * | 1997-09-05 | 1999-12-01 | 保土谷化学工业株式会社 | Zirconium compounds and electrophotographic toner containing the same |
| US6127081A (en) * | 1998-11-19 | 2000-10-03 | Toshiba Tec Kabushiki Kaisha | Developing agent and image forming apparatus |
| JP2002268286A (en) * | 2000-12-20 | 2002-09-18 | Hodogaya Chem Co Ltd | Method for producing electric charge controlling agent and electrostatic charge image developing toner containing the same |
| EP1260873A1 (en) * | 2001-05-21 | 2002-11-27 | Ricoh Company | Toner, developer and image forming method using the toner |
| JP2003262988A (en) * | 2002-03-08 | 2003-09-19 | Ricoh Co Ltd | Negatively chargeable toner and method for forming image |
| JP2004053915A (en) * | 2002-07-19 | 2004-02-19 | Ricoh Co Ltd | Method for forming image |
| CN1480790A (en) * | 2002-07-19 | 2004-03-10 | ������������ʽ���� | Toner and method of forming image by utilizing such toner |
| CN1184538C (en) * | 1997-12-05 | 2005-01-12 | 佳能株式会社 | Toner having negative triboelectric chargeability and developing method |
-
2005
- 2005-08-31 CN CNB2005100193749A patent/CN100346235C/en not_active Expired - Fee Related
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1237182A (en) * | 1997-09-05 | 1999-12-01 | 保土谷化学工业株式会社 | Zirconium compounds and electrophotographic toner containing the same |
| CN1184538C (en) * | 1997-12-05 | 2005-01-12 | 佳能株式会社 | Toner having negative triboelectric chargeability and developing method |
| US6127081A (en) * | 1998-11-19 | 2000-10-03 | Toshiba Tec Kabushiki Kaisha | Developing agent and image forming apparatus |
| JP2002268286A (en) * | 2000-12-20 | 2002-09-18 | Hodogaya Chem Co Ltd | Method for producing electric charge controlling agent and electrostatic charge image developing toner containing the same |
| EP1260873A1 (en) * | 2001-05-21 | 2002-11-27 | Ricoh Company | Toner, developer and image forming method using the toner |
| CN1387092A (en) * | 2001-05-21 | 2002-12-25 | 株式会社理光 | Hue modulating agent, developer and image forming method using said hue modulating agent |
| JP2003262988A (en) * | 2002-03-08 | 2003-09-19 | Ricoh Co Ltd | Negatively chargeable toner and method for forming image |
| JP2004053915A (en) * | 2002-07-19 | 2004-02-19 | Ricoh Co Ltd | Method for forming image |
| CN1480790A (en) * | 2002-07-19 | 2004-03-10 | ������������ʽ���� | Toner and method of forming image by utilizing such toner |
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