CN100388125C - Colouring composition for image recording and image recording agent - Google Patents
Colouring composition for image recording and image recording agent Download PDFInfo
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- CN100388125C CN100388125C CNB02158477XA CN02158477A CN100388125C CN 100388125 C CN100388125 C CN 100388125C CN B02158477X A CNB02158477X A CN B02158477XA CN 02158477 A CN02158477 A CN 02158477A CN 100388125 C CN100388125 C CN 100388125C
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- image recording
- coloured composition
- sulfonic acid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/091—Azo dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
The present invention provides a colouring composition for image recording, which has heat-resistance for keeping the original colour definition, brightness and transparence after the heat-repeated mixing. The colouring composition comprises a pigment and resins, in which the pigment component is an azo precipitated pigment composition prepared by the coupling of a diazonium salt of p-methylaniline-m-sulfonic acid with b-hydroxy naphthoic acid, and the colour precipitation of calcium after or during the coupling procedure to form C.I. pigment red 57:1, simultaneously at least one part of p-methylaniline-m-sulfonic acid is substituted by an aromatic amine containing soluble groups such as 1-amino-4-chloro-toluene-2-sulfonic acid.
Description
Technical field
The present invention relates to the image recording agent in the image recordings such as electrofax, electronic printing, xeroprinting, electrostatic recording, ink-vapor recording and heat copying record, or the image recording coloured composition that uses in its manufacturing.In more detail, the image recording coloured composition that the present invention relates to, in the image recording agent that contains color compositions and resin, pigment be to use contain have high transparent, the compositions of azo lake pigment of the C.I. paratonere 57:1 of the mixing diazonium composition of distinctiveness.
Prior art
Before this, in the magenta record agent of in image recordings such as panchromatic or monochromatic electrofax, electronic printing, xeroprinting, electrostatic recording, ink-vapor recording and heat copying record, using, can use reddish oil soluble dye, disperse dyes, the indigo pigment of sulfo-, solubility azo lake series pigments, insoluble azo pigment, dimethyl quinoline a word used for translation ketone pigment etc. as red pigment.
The problem that quasi-solution of the present invention is determined
State in the red pigment of magenta record agent the pinkish red tone that the C.I. paratonere 57:1 of solubility azo lake series pigments is near the mark in the use.Yet, when manufacturings such as electrofax dry type developer, most temperature about about 100-150 ℃ add hot milling, under such heating condition, this pigment changes tone because particle growth or crystallization change, and color is thin out, or colour saturation decline, or color becomes opaque.
In the past, when AZO pigments is used for coating, plastics, synthon painted etc., because the covering of attention color and colour rendering etc., the mean grain size of AZO pigments will be adjusted greatly, the change of size rate that heating is caused diminishes, thereby thermotolerance is risen, but, in this case, as the colorant that image recording agent is used, the distinctiveness of its tone, clarity, transparency shortcoming, image recording agent, using panchromaticly, or using when the suspension type projection is duplicated on polyester film, the distinctiveness of pigment tone, clarity, the transparency are important.
In order to solve above-mentioned shortcoming, for example, the someone proposes a kind of AZO pigments composition (spy opens flat 10-73963 communique) with specific length breadth ratio, specific surface area and particle mean size, by the use of this color compositions, can confirm effect roughly, but practicality is also undesirable.
Therefore, the purpose of this invention is to provide a kind of under the mixing effect that waits heating, the image recording coloured composition of the various function admirables such as heat-resisting fastness that the distinctiveness of tone, clarity, the transparency do not change.
The inventor has improved the shortcoming of above-mentioned original recording agent, a kind of colour rendering of developing is good, can satisfy the image recording agent C.I. paratonere 57:1 of various fastnesses and economy, find from its all result of study: the part of the para-totuidine of this a diazonium composition-sulfonic acid is used the mixing diazonium composition that aromatic amine with specific solubility group replaces and the color compositions that obtains, thermotolerance than existing C .I. paratonere 57:1 rises, can bring into play the distinctiveness of tone, clarity, the character that the transparency etc. are good, by colorant, can obtain excellent images record and finish the present invention used as image recording agent.
Be used to solve the way of this problem
Above-mentioned purpose can reach by following the present invention.Promptly, image recording coloured composition of the present invention, it is characterized in that, the compositions of azo lake pigment that uses following manufacturing in coloured composition at the image recording that contains color compositions and resin is as color compositions: make the diazo salt of a para-totuidine-sulfonic acid and betanaphthol acid carry out coupling, carry out the color lake with calcium after coupling or in the coupling and during synthetic C.I. paratonere 57:1, replace a part para-totuidine-sulfonic acid and obtain with the aromatic amine of solubility group with following general formula (1) expression.
(A represents phenyl ring or naphthalene nucleus in the formula, and X represents carboxyl or sulfonic group, and m represents the integer of 1-2.In addition, Y can be identical also can be different, expression hydrogen, or be selected from substituting group in halogen, alkyl, alkoxy and the nitro, n represents the integer of 1-6).
Embodiment of the present invention
The present invention is described in more detail below.
Image recording coloured composition of the present invention, it is characterized in that, what use is to make the diazo salt and the betanaphthol acid of the para-totuidine-sulfonic acid as color compositions carry out coupling, carry out the color lake with calcium after coupling or in the coupling and during synthetic C.I. paratonere 57:1, the compositions of azo lake pigment that obtains with an aromatic amine instead of part para-totuidine-sulfonic acid of solubility group with formula (1) expression.
Can think, in the present invention, when synthetic C.I. paratonere 57:1, by synthetic and its color simultaneously and physical property is similar and AZO pigments compound that structure is different, the mixed crystal or the crystallite potpourri of the multiple pigment particles that generates, or under the state that the mixing of the amorphous substance of part exists, has the effect that suppresses crystalline growth, this effect is that the thermotolerance under above-mentioned heating condition increases, by the image recording agent that uses this AZO pigments composition to obtain, can obtain excellent images such as bright, clarity, the transparency.
C.I. paratonere 57:1 and manufacture method thereof itself are well-known, in the present invention, it is characterized in that, a para-totuidine-sulfonic acid is its 0.1-30 mole % preferably, mixing diazonium composition with aromatic amine replacement with above-mentioned general formula (1) expression solubility group, carry out diazotising with usual way, diazotising thing that obtains and betanaphthol acid are carried out coupling and synthetic dyestuffs, this dyestuff is carried out the color lake with calcium, or in diazotising liquid, add calcium in advance, carry out the color lake when carrying out coupling and the compositions of azo lake pigment that makes.When the consumption of the aromatic amine with above-mentioned solubility group was lower than 0.1 mole of %, low as the effect of purpose of the present invention, on the other hand, when consumption was higher than 30 moles of %, the original advantageous property of azo lake pigment descended, and is unfavorable.Especially effectively consumption is the amount of occupying 0.1-10 mole % in azo composition total amount.
The compositions of azo lake pigment that the present invention uses, when it is made, in the suitable stage of diazonium liquid, maceration extract, dyestuff or pigment slurry, in the amount of the scope that does not hinder the object of the invention, also can add various fatty amines, water soluble resin, surfactant, other adjuvants, color compositions is handled again.
In the aromatic amine with following general formula (1) expression solubility group that the present invention uses (below be called the solubility aromatic amine sometimes), A represents phenyl ring or naphthalene nucleus, and X represents carboxyl or sulfonic group, and m represents the integer of 1-2.In addition, Y can be identical also can be different, 1-6 of expression is selected from hydrogen atom, or alkyl such as halogen atom, methyl, ethyl, butyl such as chlorine, bromine, iodine, the group in alkoxy such as methoxyl, ethoxy, propoxyl group and the nitro.
As the solubility aromatic amine, for example, can enumerate 1-amino-4-methyl-5-chloro benzene-2-sulfonic acid, 1-amino-4-chloro-5-Toluene-2,4-diisocyanate-sulfonic acid, 1-amino-4-chloro-5-ethylbenzene-2-sulfonic acid, 1-amino-2-toluene-4-sulfonic acid, 1-amino-4-chlorobenzene-2-sulfonic acid, 1-amino-4-chlorobenzene-3-sulfonic acid, 1-amino-2-nitrobenzene-4-sulfonic acid, 1-amino-4-methoxybenzene-2-sulfonic acid, 1-amino-4-ethoxybenzene-2-sulfonic acid, 1-aminobenzene-2-sulfonic acid, 1-aminobenzene-4-sulfonic acid, 1-aminobenzene-2-sulfonic acid, 1-aminobenzene-3, the 4-disulfonic acid, 2-amino naphthalenes-1-sulfonic acid, 2-amino naphthalenes-1,5-disulfonic acid etc.All be easy on these compound industry obtain and effectively.Self-evident, these solubility aromatic amines can also can be used in combination with a kind.
The resin that uses among the present invention, in this resin combination of solid state, it is the dispersion medium of color compositions, and in the coloured composition of liquid condition, it is function as the color compositions dispersing aid, in addition, when using as recording agent actually, its effect is the sticking agent that plays pigment on printing medium.Resin as these purposes uses, the original any resin that uses all can use in dry type developer such as electrofax, electronic printing, xeroprinting, electrostatic recording and wet type developer, heat copying record paper slip and image recording agents such as film, oiliness and water-based ink jet, and is not particularly limited.In addition, in various uses, as required, original known additives, for example, Electrostatic Control agent, glidant or all can use as solvent, the water-medium of medium.
The coloured composition that in the coloured composition that image recording of the present invention is used, can also contain in addition, the high concentration of the above-mentioned compositions of azo lake pigment that high concentration is arranged.Purpose is to contain high concentration pigment, fully grinds in advance and makes its dispersion, mixes colours, and subsequent handling is carried out easily, solid states such as coarse grain, meal, fine powder, sheet, fritter shape, and perhaps pasty state or aqueous Any shape all can be used.
With in the coloured composition, contain the content of the above-mentioned compositions of azo lake pigment of C.I. paratonere 57:1 at image recording of the present invention, different different because of application target, be not particularly limited.Solid-state, the pasty state or the liquid coloured composition that contain the above-mentioned compositions of azo lake pigment of high concentration, the about 15-60 weight of its content %, about preferred 20-50 weight %, when the colorant as electronic printing developer etc. used, its content was 1～10 weight %, preferred 2～8 weight %, when the colorant as heat copying paper tape and film uses, be 2-20 weight %, about preferred 4-15 weight %, use optimal content according to application target.
Embodiment
Enumerate embodiment and comparative example below with more specific description the present invention.In addition, ' part ' in the literary composition or ' % ' all are benchmark with weight except that prior special instruction.
Embodiment 1
3.8 parts in 17.8 parts of 1-amino-4-Toluene-2,4-diisocyanate-sulfonic acid and NaOH are added in 360 parts in the water, often descend stirring and dissolving.Then, will be in 30 parts of water after heating for dissolving has the solution of 0.4 part in NaOH and 1-amino-4-chloro-5-Toluene-2,4-diisocyanate-sulfonic acid 1.1 parts (5 moles of % of diazonium composition total amount) to add, in this solution, add 25 parts of 35% hydrochloric acid, drop into to ice to make and reach 5 ℃.
Then, once be added on the solution of 6 parts of sodium nitrites that dissolve in 20 parts of water in the above-mentioned solution, make and carry out diazotising, stir 30 minutes as diazonium liquid in 5-8 ℃.
On the other hand, add 18.8 parts of betanaphthol acid and 10.0 parts in NaOH and stirring and dissolving in 800 parts of water, water is adjusted to 1000 parts, and temperature transfers to 10 ℃, as maceration extract.
Above-mentioned diazonium liquid was dripped to this maceration extract with 20 minutes, just carry out coupling reaction, synthetic dyestuffs after, stirred 1 hour.Then, the pH of reactant liquor is transferred to 10-11, after adding rosin soap (3.2 parts of rosin (be pigment 7%) and NaOH 0.4 part water-soluble 60 parts in solution), interpolation lime chloride (2 hydrate) 19 parts (to 1.3 moles of 1 mole of interpolations of dyestuff) makes and carries out the color lake.Stir and be warming up to 80 ℃ after 1 hour, filtration and washing obtain filter press cake, in addition, its part are carried out drying and pulverizing, make powder, obtain red azo mordant pigment composition of the present invention (dry output is 45.6 parts).
30 parts of the compositions of azo lake pigment that obtains above and styrene-methacrylate ester copolymer resins (about 110 ℃ of softening point, about 56 ℃ of glass transition point, the weight-average molecular weight that GPC records (being converted into polystyrene standard) about 90,000) 70 part, carry out fully mixingly with three-high mill, make pigment dispersing.After the cooling, pulverize, obtain containing the high concentration coloured composition meal of red pigment 30% concentration.
Then, 3 parts of the Electrostatic Control agent of the coordination salt of 14.7 parts of high concentration coloured compositions that contains the red pigment that obtains like this and chromium system, carry out mixing with usual way for 82.3 parts with the styrene-methacrylate ester copolymer resin of above-mentioned use, after the cooling in addition after the coarse crushing, it is broken to carry out fine powder with injector-type mill, carry out classification again, obtain the red resin composition of 5-30 μ m.
Then, press the colloidal silica of usual way interpolation, fully mix, as red electrofax dry type developer as glidant.It is mixed with the carrier magnetic powder, can obtain distinct red image with the result that electrophotographic copier carries out single-color copying with the panchromatic video picture of negative charge.Image presents distinctness and red clearly, shows the good fastnesses of various physical propertys such as photostability.In addition, when similarly on the polyester sheet that the suspension type projection is used, duplicating, present transparent image, on the suspension type projection screen, show distinct red image.
Also have, adopt copper phthalocyanine blue pigment as dark green pigment, monoazo yellow pigment as yellow uitramarine, charcoal blacks as black pigment, operate equally with above-mentioned, make dark green developer, yellow developer, black developer respectively, carry out the duplicating of four looks panchromatic with the above-mentioned carmetta that obtains, obtain distinct full-colour image.Equally, on the suspension type projection screen, duplicate, can obtain presenting the full-colour image of distinct panchromatic image on the screen.
Embodiment 2
Except that replacing operating similarly to Example 1 1-amino-4-chloro-5-Toluene-2,4-diisocyanate-sulfonic acid, obtain compositions of azo lake pigment with 1-amino-4-methyl-5-chloro benzene-2-sulfonic acid 1.1 parts (being 5 moles of % of whole diazonium compositions).Adopt resulting compositions of azo lake pigment, make the high concentration coloured composition, make electrophotography dry type developer with it again according to the method for introducing among the embodiment 1.This developer is mixed with carrier, carry out monochrome and panchromatic duplicating with panchromatic electrophotographic copier, the result obtains distinct image.Image manifests distinctness and red clearly and four look full-colour images, and each physical property all presents good fastness.
Embodiment 3
Except that replacing 1-amino-4-chloro-5-Toluene-2,4-diisocyanate-sulfonic acid with 1-amino-4-methyl-5-chloro benzene-2-sulfonic acid 0.55 part of (being 2.5 moles of % of whole diazonium compositions) and 2-amino naphthalenes-1-sulfonic acid 0.55 part (for 2.5 moles of % of whole diazonium compositions), operation obtains compositions of azo lake pigment similarly to Example 1.Adopt resulting compositions of azo lake pigment, make the high concentration coloured composition, make electrophotography dry type developer with it again according to the method for introducing among the embodiment 1.This developer is mixed with carrier, carry out monochrome and panchromatic duplicating with panchromatic electrophotographic copier, the result obtains distinct image.Image shows distinct and red clearly and four look full-colour images, and each physical property all presents good fastness.
Embodiment 4
Except that replace 1-amino-4-chloro-5-Toluene-2,4-diisocyanate-sulfonic acid with 2-amino naphthalenes-1-sulfonic acid 1.1 parts (being 5 moles of % of whole diazonium compositions), similarly to Example 1, make compositions of azo lake pigment.Adopt 10 parts of resulting compositions of azo lake pigment, make coloured composition with 3 parts in 41 parts of ester type waxes, 41 parts in paraffin series wax, styrene-5 parts of methacrylate ester multipolymers and silica as bonding agent, it is coated on the polyethylene film according to usual way, as red heat copying recording ink film.Duplicate on the duplicating machine of panchromatic heat copying with it, obtain distinct red copy image.This image shows the good fastnesses of each physical property such as photostability.In addition,, can obtain transparent image, on screen, present distinct image when when the suspension type projection is duplicated on polyester sheet.Also have, adopt copper phthalocyanine blue pigment, monoazo yellow pigment, charcoal blacks, operate equally, make dark green, yellow and black fever respectively and duplicate the printing ink film with above-mentioned, carry out the duplicating of four looks panchromatic with the above-mentioned carmetta that obtains, obtain distinct full-colour image.In addition, duplicate on polyester sheet, on screen, can obtain the full-colour image of distinct panchromatic image in the suspension type projection.
Embodiment 5
Make water dispersible pigment dispersion for 62 parts with 5 parts of the compositions of azo lake pigment that obtains among the embodiment 4, water-soluble phenylethene-acrylate-3 parts of methacrylic acid diethanolamine salt copolymers, 22 parts of ethylene glycol, 8 parts of glycerine and water, remove the pigment corase particles that does not disperse with ultracentrifuge and remove, obtain the aqueous inkjet red ink.Adopt this printing ink,, obtain distinct red image with having the drop on demand ink jet press printing image information of piezo-electric resonator.In addition, adopt copper phthalocyanine blue pigment, monoazo yellow pigment, charcoal blacks, operate equally, make the printing ink that dark green, yellow and black ink-jet are used respectively with above-mentioned, they are carried out the duplicating of four looks panchromatic with the above-mentioned red ink for inking that obtains, obtain distinct full-colour image.
Comparative example 1
4.0 parts in 18.7 parts of 1-amino-4-Toluene-2,4-diisocyanate-sulfonic acid and NaOH is added in 360 parts in the water stirring and dissolving under the normal temperature.In this solution, add 25 parts of 35% hydrochloric acid, on the rocks, be cooled to 5 ℃.Then, once add 6 parts of water-soluble 20 parts of solution that obtain of sodium nitrite in this solution and make it diazotising, stirred 30 minutes in 5-8 ℃, obtain diazonium liquid.
On the other hand, add 18.8 parts of betanaphthol acid and 10.0 parts of stirring and dissolving of NaOH in 800 parts in water, water is adjusted to 1000 parts, and temperature transfers to 10 ℃, as maceration extract.
Above-mentioned diazonium liquid dropped to 20 minutes make the generation coupling reaction in this maceration extract, stirred behind the synthetic dyestuffs 1 hour.Secondly, the pH of reactant liquor is transferred to 10-11, add rosin soap (3.2 parts of rosin (and for pigment 7%) and 0.4 part of solution that is dissolved in 60 parts of water of NaOH) after, add 19 parts in lime chloride (2 hydrate) (to 1.3 moles of 1 mole of interpolations of dyestuff) and make and carry out the color lake.Be warming up to 80 ℃ after 1 hour, the filter press cake that filtration and washing are made carries out drying with its part and powder is made in pulverizing, obtains compositions of azo lake pigment.Adopt this compositions of azo lake pigment that obtains,, make the high concentration coloured composition, make electrophotography dry type developer with it again according to the method for introducing among the embodiment 1.It is mixed with carrier, and the result who adopts panchromatic electrophotographic copier to carry out single-color copying obtains the vividness difference, opaque red image.
The effect of invention
Recording image coloured composition of the present invention, use contains useful mixing diazonium one-tenth as pigment composition Divide the compositions of azo lake pigment of synthetic C.I. paratonere 57:1, can obtain thus adopting original C.I. paratonere 57:1 high tinting strength, tinting power, distinctiveness, definition, the transparency that can't obtain, heat-resisting The various fastnesses such as property are all good, even be heated in the manufacturing process of recording image with coloured composition Also stable, with this recording image usefulness coloured composition during as image recording agent, can be distinct, clear, The image stabilization ground that transparent feel is high carries out record. In addition, also can be long-time as the liquid recording agent time Stably carry out record.
Claims (13)
1. recording image coloured composition; It is characterized in that; Use in the coloured composition at the recording image that contains color compositions and resin; The compositions of azo lake pigment that uses following manufacturing is as color compositions: make the diazol of a para-totuidine-sulfonic acid and betanaphthol acid carry out coupling; Carry out the color lake with calcium after coupling or in the coupling and during synthetic C.I. paratonere 57:1; Replace a part para-totuidine-sulfonic acid and obtain with the aromatic amine of the solubility group with following row general formula (1) expression
A represents phenyl ring or naphthalene nucleus in the formula, and X represents carboxyl or sulfonic group, and m represents the integer of 1-2, in addition, Y can be identical also can be different, expression hydrogen, or be selected from substituting group in halogen, alkyl, alkoxy and the nitro, n represents the integer of 1-6.
2. the image recording coloured composition described in the claim 1 wherein, has the 0.1-30 mole % that accounts for whole diazonium compositions with the aromatic amine of the solubility group of general formula (1) expression.
3. the image recording coloured composition described in the claim 1 or 2, wherein, the A in the general formula (1) is a naphthalene nucleus.
4. the described image recording coloured composition of claim 1, wherein, the aromatic amine that has with the solubility group of general formula (1) expression is 2-amino naphthalenes-1-sulfonic acid.
5. the described image recording coloured composition of claim 2, wherein, the aromatic amine that has with the solubility group of general formula (1) expression is 2-amino naphthalenes-1-sulfonic acid.
6. adopt the image recording agent of the described image recording of claim 1 with coloured composition.
7. adopt the image recording agent of the described image recording of claim 2 with coloured composition.
8. adopt the image recording agent of the described image recording of claim 3 with coloured composition.
9. adopt the image recording agent of the described image recording of claim 4 with coloured composition.
10. adopt the image recording agent of the described image recording of claim 5 with coloured composition.
11. any one described image recording agent among the claim 6-10 wherein also contains carmine color compositions and dyestuff at least a kind.
12. any one described image recording agent among the claim 6-10 is the electrophotography toner.
13. the image recording agent described in the claim 11 is the electrophotography toner.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002038673A JP2003241431A (en) | 2002-02-15 | 2002-02-15 | Color composition for image recording and image recording agent |
| JP038673/2002 | 2002-02-15 | ||
| JP038673/02 | 2002-02-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1438547A CN1438547A (en) | 2003-08-27 |
| CN100388125C true CN100388125C (en) | 2008-05-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB02158477XA Expired - Fee Related CN100388125C (en) | 2002-02-15 | 2002-12-25 | Colouring composition for image recording and image recording agent |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2003241431A (en) |
| KR (1) | KR100592171B1 (en) |
| CN (1) | CN100388125C (en) |
| TW (1) | TW591088B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108795087A (en) * | 2018-05-21 | 2018-11-13 | 杭州红妍颜料化工有限公司 | A kind of preparation method of C.I. paratoneres 2 |
| CN108864752B (en) * | 2018-08-10 | 2020-04-28 | 天津城建大学 | Water-dispersible pigment red 57:1 modified pigment and preparation method thereof |
| US20220050396A1 (en) * | 2018-09-28 | 2022-02-17 | Zeon Corporation | Magenta toner and method for producing the magenta toner |
| JP7263754B2 (en) * | 2018-12-13 | 2023-04-25 | Dic株式会社 | coated azo lake pigment |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02298559A (en) * | 1989-05-12 | 1990-12-10 | Toyo Ink Mfg Co Ltd | Monoazo lake pigment and printing ink composition |
-
2002
- 2002-02-15 JP JP2002038673A patent/JP2003241431A/en active Pending
- 2002-12-07 KR KR20020077552A patent/KR100592171B1/en active IP Right Grant
- 2002-12-09 TW TW91135594A patent/TW591088B/en not_active IP Right Cessation
- 2002-12-25 CN CNB02158477XA patent/CN100388125C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02298559A (en) * | 1989-05-12 | 1990-12-10 | Toyo Ink Mfg Co Ltd | Monoazo lake pigment and printing ink composition |
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| Publication number | Publication date |
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| TW200302856A (en) | 2003-08-16 |
| KR100592171B1 (en) | 2006-06-23 |
| TW591088B (en) | 2004-06-11 |
| KR20030069041A (en) | 2003-08-25 |
| CN1438547A (en) | 2003-08-27 |
| JP2003241431A (en) | 2003-08-27 |
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