CN105001673A - Aqueous composite nanometer coloring agent preparation method - Google Patents
Aqueous composite nanometer coloring agent preparation method Download PDFInfo
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Abstract
The present invention discloses an aqueous composite nanometer coloring agent preparation method, which is characterized in that a mini emulsification/solvent evaporation method is used to dissolve an oil-soluble dye in a polymer solution, the obtained solution is mixed with a water phase added with a surfactant, a high speed shear mini emulsification process treatment is performed to form core-shell structure oil-soluble dye/polymer composite nanometer latex particles, and finally the volatile organic solvent is subjected to rotary evaporation removing under a low air pressure condition so as to obtain the composite nanometer coloring agent capable of being uniformly dispersed in the water phase. According to the present invention, the prepared solvent type dye/polymer composite nanometer coloring agent has characteristics of bright color, high color saturation, significantly-improved water resistance, significantly-improved light resistance, other significantly-improved use performances, and excellent storage stability, and is suitable for high-resolution inkjet printer inks, digital textile inkjet printing machine inks, liquid crystal displays, cosmetics and other fields, and the method has characteristics of high formula universality, simple operation, short time-consuming, and effective production cost reducing.
Description
Technical field
The present invention relates to the preparation method of water-based composite Nano tinting material, especially a kind of is raw material with solvent dye, prepares the preparation method that particle diameter is the water-based composite Nano tinting material of 50-200nm.
Background technology
Dyestuff and pigment, have in visible region absorption or radiative ability and present distinct colors, can be used as tinting material and be widely used in image and data recording system, photograph and the field such as manifolding technology, chemical analysis and biological detection, Laser Devices, liquid-crystal display.When wherein dyestuff uses as tinting material, there is Color Range wide, colorimetric purity higher and with the advantage such as matrix avidity is strong.But it is fast light and color fastness to water is poor, easily occur in use procedure that resolving power is not high, bleeding and colour contamination phenomenon, thus affect chromatic effect.And pigment replaces dyestuff when using as tinting material, though can improve weather resistance, colour vividness is inadequate, needs by mechanical mill, stability extreme difference in system in use procedure.
Dyestuff or pigment molecule and aggregate are loaded in nanometer polymer particle matrix and can prepare composite Nano tinting material, prepared composite particles diameter is 50-300 nanometer, form and even size distribution, the Color Range of original pigment, vividness and saturation ratio can be kept, there is again excellent light fastness, color fastness to water and storage-stable performance.Can effectively overcome dyestuff weathering resistance when using as tinting material poor, and paint color is dim, the defect of storage-stable performance difference.
The preparation of composite Nano tinting material mainly makes dyestuff or pigment and matrix material compound by covalent linkage or non covalent bond effect, and forms uniform and stable dispersion system.The domestic and international research prepared for composite Nano tinting material is comparatively extensive at present, people (the US Patent 5 such as the Rochester of Xerox company of the U.S., 604,076 (1997) .) select the tensio-active agent of different structure to make pigment electric charge different from polymer latex particles surface band, after the two mixing, make it assemble by the control of temperature, finally prepare the toning agent that Surface coating is made up of the granules of pigments of polymeric film.Because this method adopts the coated process of polymeric film, and unconventional mechanical dispersion or surfactant-dispersed process, the toning agent obtained has good stability, and has higher color fastness to water.But the coloring agent particle that this method obtains is comparatively large, is about 2-20 micron, easily causes the problems such as spray orifice blocking in use procedure.
People (the Macromol.Chem.Phys.2001 such as the Landfester of Germany; 202; carbon black/polystyrene composite Nano the tinting material that 51-60) adopted the method for mini-emulsion polymerization to prepare; because fine emulsion polymerization is by the effect of continuous print ultrasonic shear; pigment aggregate is made to confine in monomer droplet; and form the mixture of nucleocapsid structure; the coloring agent particle that the method obtains can be controlled in below 200 nanometers; the protection of top layer polymeric shell layer can make coloring agent particle be scattered in water on the one hand in addition, possesses good weather resistance simultaneously.But because the pigment selected is as coated object, itself chemical structure determine its monomer mutually in dispersed comparatively difficulty, the storer stability of the final mixture formed also need to improve.
People (the Colloid.Polym.Sci.2003 such as the Takasu of Japan; 282:119-26.) selected solvent dye as tinting material, the same method adopting mini-emulsion polymerization, has prepared phthalocyanine pigment/polystyrene composite Nano pigment.Dyestuff solubleness in monomer that the method is selected is higher, and efficiently solve the problem that encapsulation object pigment disperses mutually at monomer, achieve the efficiently coated of oil-soluble colourant, prepared mixture grain is through also caning be controlled in below 200 nanometers.But because the method raw material choose scope is less, pervasive degree is not high.
The people such as the Hu Zhenkun of Shanghai Communications University (Dyes and Pigments.2008; 76:173-8.) for the problems referred to above, have employed the method for the mini-emulsion polymerization of improvement, synthesize solvent dye/composite nano-polymers colorant.The method adopts two-step approach, first forms the prepolymer seeds being coated with solvent dye, then makes it that involucrum polyreaction occur.The introducing of linking agent and acute altogether monomer achieves combining closely of dyestuff object and matrix material, and the introducing simultaneously participating in the photostabilizer of polymerization also makes prepared compound colorant have more excellent light fastness.But the method manufacture craft is more complicated, coating efficiency is to be improved.
Summary of the invention
Problem to be solved by this invention is to provide a kind of preparation method of water-based composite Nano tinting material, it is bright in luster except what retain that dyestuff possesses to use compound pigment prepared by the method, outside saturation ratio advantages of higher, also have higher fast light and color fastness to water concurrently, and the use properties such as the storage stability of excellence, and there is less particle diameter.
The invention provides a kind of method (Combinedminiemulsion/solvent evaporation (MESE)) that fine crankshaft/solvent evaporation combines and prepare dyestuff/composite nano-polymers tinting material, it is characterized in that, adopt the method for fine crankshaft/solvent evaporation, oil-soluble colourant are dissolved in macromolecule polymer solution, after mixing with the aqueous phase being added with tensio-active agent, by high speed shear fine crankshaft art breading, form the oil-soluble colourant/composite nano-polymers emulsion particle with nucleocapsid structure, finally volatile organic solvent is rotated under low air pressure condition additional issue to remove, obtaining can at the homodisperse composite Nano tinting material of aqueous phase.
Preferably, be specially: respectively by 1-5 part polymethylmethacrylate (PMMA, Mw 300000), 1-5 part solvent dye is dissolved in 19-30 part volatile solvent, obtains oil phase after stirring; 0.15-1.5 part sodium laurylsulfonate (SDS) is dissolved in deionized water, as aqueous phase; Pour oil phase into aqueous phase, by magnetic stirring apparatus Keep agitation pre-emulsification more than 1 hour; Thereupon under ice bath protective condition, by ultrasonic stirrer with the output rating of 665-855 by prepared emulsion fine crankshaft 30s-10min; Finally adopt Rotary Evaporators to remove volatile solvent and obtain composite Nano tinting material.
Preferably, described solvent dye is solvent-borne type azoic dyestuff or anthraquinone dye.
More preferably, described solvent dye is C.I. solvent black 3, C.I. solvent black 45, C.I. solvent black 27, C.I. solvent red 26, C.I. solvent red 92, C.I. solvent red 27, C.I. solvent red 124, C.I. solvent red 8, C.I. solvent red 91, C.I. solvent red 217, C.I. solvent red 218, C.I. solvent blue 45, C.I. solvent blue 44, C.I. solvent blue 35, C.I. solvent yellow 16 3, C.I. solvent yellow 79, C.I. solvent yellow 83, C.I. solvent yellow 62, any one in curcumine and carotene.
Preferably, described volatile solvent is ethyl acetate or trichloromethane.
Preferably, the steaming time of revolving of described Rotary Evaporators is 30min, and temperature is set as 40 DEG C.
For chemical structure and the use properties of the composite Nano tinting material of the present invention's acquisition, carry out a series of sign and test.Comprise the elementary composition analysis of nanometer tinting material, microscopic appearance is observed, Nano composite granules grain warp and measure of spread thereof, rotary viscosity measures, composite coloration agent light fastness, color fastness to water measure and the storage-stable performance of prepared aqueous dispersion is tested, and prepared nanometer tinting material is applicable to the fields such as high resolution inkjet printer ink, digitizing weaving ink-jet decorating machine ink, liquid-crystal display, makeup.
A kind of preparation method preparing dyestuff/composite nano-polymers tinting material involved in the present invention has following characteristics:
(1) the present invention adopts MESE method, use the tensio-active agent of minute quantity, by the organic polymer soln that dissolves oil-soluble colourant and aqueous phase Homogeneous phase mixing, during newborn supersound process thin through high speed shear, solvent dye can be used as the stability that co-stabilizer increases system on the one hand, its hydrophobic characteristic makes it rest on polymeric matrix inside simultaneously, and then be coated in polymer shell, after the volatile solvent evaporative removal of dissolve polymer, the particle diameter that can obtain being dispersed in aqueous phase is the dyestuff of about 100nm/composite nano-polymers microballoon, this dispersion system can replace dyestuff as tinting material.Dyestuff/composite nano-polymers pigment granule seed prepared by employing the method is through being evenly distributed, and storage-stable performance is excellent.Because prepared pigment granule seed is through caning be controlled in 100 ran, therefore dyestuff can be retained bright in luster, the use properties that colorimetric purity height etc. are excellent.Simultaneously due to the protection of sheath polymers material, light fastness and color fastness to water that composite Nano pigment significantly promotes can be given.
(2) MESE legal system provided by the present invention is for dyestuff/composite nano-polymers tinting material, select volatile solvent as the dispersion medium of dyestuff, due to the solubleness that dyestuff is higher in a solvent, add dyestuff encapsulation concentration in the polymer matrix and coating efficiency, the controlled synthesis of the composite Nano tinting material of different concns can be realized.In addition, the solvent dye of the solvent-soluble solution different chemical structures used, adds the pervasive degree of the method.In addition with uses at present compared with the more fine emulsion polymerization preparing composite Nano tinting material, this process simplify technological process, consuming time short, can effectively enhance productivity, reduction production cost.
Accompanying drawing explanation
Fig. 1 is the data drawing list that nanometer tinting material prepared by each embodiment compares with corresponding color inkjet printer ink water resistance; Wherein, ● nanometer tinting material, ▲ printer ink;
Fig. 2 is the data drawing list that nanometer tinting material compares with corresponding dyestuff light stability.Wherein, ■ nanometer tinting material, ▲ comparative dye.
Embodiment
For making the present invention become apparent, hereby with preferred embodiment, be described in detail below.
The analysis test method of water-based composite Nano tinting material prepared by embodiment 1-7 is as follows:
The present invention is to the water resistance evaluation method of nanometer tinting material: be soaked in respectively in deionized water by the paper being coated with composite coloration agent, takes out and dry after balance 10min, the aberration of sample before and after being soaked by the test of spectrophotometric tester.As a comparison, the sample of the identical form and aspect printed by Canon's color inkjet printer (IP4760) soaks same time in above-mentioned medium, and the aberration of front and back sample is soaked in test.As shown in Figure 1, aberration is less for test result, proves that the color fastness to water of tinting material is higher.
The present invention is to the light fastness evaluation method of nanometer tinting material: be sprayed on printer paper by the dye solution of same concentrations and dyestuff/PMMA dispersion liquid respectively, light fastness instrument is placed on after drying under lucifuge condition, carry out different time (1, 2, 3, 6, 12, 24, 48, 60 and 72h) tan by the sun, tan by the sun temperature in process and be held in 25 DEG C, relative humidity is 65%, subsequently by spectrophotometric tester (Datacolor 650, the U.S.) test the aberration (CIELAB Δ E) tanning by the sun front and back sample, to analyze the change of light stability before and after dyestuff encapsulation, test result as shown in Figure 2.
The present invention is to the storage-stable performance evaluation method of nanometer tinting material: prepared composite coloration agent dispersing liquid is placed 4 months, by grain warp and the distribution thereof of nano-particle size analysis instrument test dye/PMMA composite particles, and with 4 months before the analog value of synthetic coloring matter dispersion liquid contrast, observe in addition and whether have precipitation to live flocculation phenomenon.If through place after, grain through and distribution substantially unchanged, and do not observe precipitation produce, then it is outstanding for evaluating this sample storage stability.
Embodiment 1
Take 0.05g sodium laurylsulfonate, make it be dissolved in 30g deionized water completely, as aqueous phase; 0.3 gram of C.I. solvent black 3 and 0.5g polymethylmethacrylate are dissolved in 9.5g volatile solvent ethyl acetate, after making dyestuff and PMMA be dissolved in solvent completely by magnetic stirring apparatus, obtain oil phase.Pour oil phase into aqueous phase, by magnetic stirring apparatus Keep agitation pre-emulsification 1 hour; Thereupon under ice bath protective condition, by ultrasonic stirrer with the output rating of 855 watts by prepared emulsion fine crankshaft 3min.Finally adopt Rotary Evaporators to remove volatile solvent and obtain C.I. solvent black 3/polymethylmethacrylate composite Nano tinting material.
The final black nano coloring agent particle average particle size obtained is 105 nanometers, and polydispersity index is 0.096, can be dispersed in aqueous phase.The composite Nano tinting material obtained is after spraying and soak in water, aberration Δ E is only 0.22 after tested, and the ink for ink-jet printer sample of sample is after water soaking as a comparison, Δ E is up to 10, and therefore composite Nano tinting material shows the water resistance significantly improved.In addition, the composite Nano tinting material prepared by data presentation the present invention is through continuous illumination after 72 hours, and Δ E is 1.77, and its contrast sample is under similarity condition after illumination, and Δ E is up to 16.55.After long-time placement, composite Nano colorant dispersion does not observe precipitation or flocculation produces, coloring agent particle size and distribution substantially unchanged, storage-stable performance is evaluated as outstanding.
Embodiment 2
Get 0.2g sodium laurylsulfonate, make it be dissolved in 100g deionized water completely, as aqueous phase; 1.5gC.I. solvent black 3 and 1.5g polymethylmethacrylate are dissolved in 27g volatile solvent trichloromethane and obtain oil phase.Pour oil phase into aqueous phase, by magnetic stirring apparatus Keep agitation pre-emulsification 1 hour; Thereupon under ice bath protective condition, by ultrasonic stirrer with the output rating of 665 watts by prepared emulsion fine crankshaft 5min.Finally adopt Rotary Evaporators to remove volatile solvent and obtain C.I. solvent black 3/polymethylmethacrylate composite Nano tinting material.
Final prepared black nano coloring agent particle and embodiment 1 to obtain finished product identical, aqueous phase can be dispersed in, and (the sample Δ E that before and after water soaking, this embodiment obtains is 0.28 to show the water resistance that significantly improves and light fastness, after continuous illumination, sample Δ E is 1.49, and its contrast sample through the same terms soak before and after and continuous illumination before and after with embodiment 1, be respectively 10 and 16.55).The nanometer colorant dispersion storage-stable performance that this embodiment obtains is evaluated as outstanding.
Embodiment 3
0.5g sodium laurylsulfonate is dissolved in 100g deionized water completely and obtains aqueous phase, get 1 gram of C.I. solvent red 26 and 1.5g polymethylmethacrylate and be dissolved in completely in 27.5g volatile solvent trichloromethane and obtain oil phase.With the pre-emulsification and the process of fine crankshaft ultrasound procedure of embodiment 2 the same terms after, adopt Rotary Evaporators remove volatile solvent obtain red composite Nano tinting material.
Final red nano tinting material embodiment 1,2 finished product that obtains obtained is identical, aqueous phase can be dispersed in, storage-stable performance is evaluated as outstanding, (the sample Δ E that before and after water soaking, this embodiment obtains is 0.36, and its contrast sample Δ E before and after the same terms soaks is 13.11 to show the water resistance that significantly improves and light fastness; Before and after continuous illumination, the tinting material Δ E that this embodiment obtains is 1.24, and its contrast sample Δ E is up to 13.04).
Embodiment 4
Take 0.3g sodium laurylsulfonate, make it be dissolved in 100g deionized water completely, as aqueous phase; 0.5 gram of C.I. solvent blue 45 and 1.5g polymethylmethacrylate are dissolved in 28g volatile solvent trichloromethane, obtain oil phase.With the pre-emulsification and the process of fine crankshaft ultrasound procedure of embodiment 2 the same terms after, adopt Rotary Evaporators remove volatile solvent obtain blue composite Nano tinting material.
The final blue nanometer tinting material finished product that above-described embodiment obtains obtained is identical, aqueous phase can be dispersed in, storage-stable performance is evaluated as outstanding, (the sample Δ E that before and after water soaking, this embodiment obtains is 0.14, and its contrast sample Δ E before and after the same terms soaks is 15.28 to show the water resistance that significantly improves and light fastness; Before and after continuous illumination, the tinting material Δ E that this embodiment obtains is 1.63, and its contrast sample Δ E is up to 14.18).
Embodiment 5
0.5g sodium laurylsulfonate is dissolved in 100g deionized water completely and obtains aqueous phase, get 1 gram of C.I. solvent yellow 16 3 and 1.5g polymethylmethacrylate and be dissolved in completely in 27.5g volatile solvent trichloromethane and obtain oil phase.With the pre-emulsification and the process of fine crankshaft ultrasound procedure of embodiment 2 the same terms after, adopt Rotary Evaporators remove volatile solvent obtain yellow composite Nano tinting material.
The final Yellow nanometer tinting material finished product that above-described embodiment obtains obtained is identical, aqueous phase can be dispersed in, storage-stable performance is evaluated as outstanding, (the sample Δ E that before and after water soaking, this embodiment obtains is 0.28, and its contrast sample Δ E before and after the same terms soaks is 23.14 to show the water resistance that significantly improves and light fastness; Before and after continuous illumination, the tinting material Δ E that this embodiment obtains is 1.78, and its contrast sample Δ E is up to 12.36).
Embodiment 6
0.5g curcumine and 1.5g polymethylmethacrylate are dissolved in 28g volatile solvent trichloromethane completely and obtain oil phase, 0.5g sodium laurylsulfonate is dissolved in 100g deionized water completely and obtains aqueous phase.Pour oil phase into aqueous phase, by magnetic stirring apparatus Keep agitation pre-emulsification 1 hour; Thereupon under ice bath protective condition, by ultrasonic stirrer with the output rating of 855 watts by prepared emulsion fine crankshaft 3min.Finally adopt Rotary Evaporators to remove volatile solvent and obtain curcumine/polymethylmethacrylate composite Nano tinting material.
The final Yellow nanometer tinting material obtained is identical with finished product that above-described embodiment obtains, aqueous phase can be dispersed in, storage-stable performance is evaluated as outstanding, (the sample Δ E that before and after water soaking, this embodiment obtains is 0.17, and its contrast sample Δ E before and after the same terms soaks is 16.28 to show the water resistance that significantly improves and light fastness; Before and after continuous illumination, the tinting material Δ E that this embodiment obtains is 1.21, and its contrast sample Δ E is up to 15.2).
Embodiment 7
1.5g carotene and 1.5g polymethylmethacrylate are dissolved in 27g volatile solvent trichloromethane completely and obtain oil phase, 0.5g sodium laurylsulfonate is dissolved in 100g deionized water completely and obtains aqueous phase.Pour oil phase into aqueous phase, by magnetic stirring apparatus Keep agitation pre-emulsification 1 hour; Thereupon under ice bath protective condition, by ultrasonic stirrer with the output rating of 665 watts by prepared emulsion fine crankshaft 5min.Finally adopt Rotary Evaporators to remove volatile solvent and obtain carotene/polymethylmethacrylate composite Nano tinting material.
The final orange nanometer tinting material obtained is identical with finished product that above-described embodiment obtains, aqueous phase can be dispersed in, storage-stable performance is evaluated as outstanding, (the sample Δ E that before and after water soaking, this embodiment obtains is 0.28, and its contrast sample Δ E before and after the same terms soaks is 8.25 to show the water resistance that significantly improves and light fastness; Before and after continuous illumination, the tinting material Δ E that this embodiment obtains is 1.24, and its contrast sample Δ E is up to 13.43).
Claims (6)
1. the preparation method of a water-based composite Nano tinting material, it is characterized in that, adopt the method for fine crankshaft/solvent evaporation, oil-soluble colourant are dissolved in macromolecule polymer solution, after mixing with the aqueous phase being added with tensio-active agent, by high speed shear fine crankshaft art breading, form the oil-soluble colourant/composite nano-polymers emulsion particle with nucleocapsid structure, finally volatile organic solvent is rotated under low air pressure condition additional issue to remove, obtaining can at the homodisperse composite Nano tinting material of aqueous phase.
2. the preparation method of water-based composite Nano tinting material as claimed in claim 1, it is characterized in that, be specially: respectively by 1-5 part polymethylmethacrylate, 1-5 part solvent dye is dissolved in 19-30 part volatile solvent, obtains oil phase after stirring; 0.15-1.5 part sodium laurylsulfonate is dissolved in deionized water, as aqueous phase; Pour oil phase into aqueous phase, by magnetic stirring apparatus Keep agitation pre-emulsification more than 1 hour; Thereupon under ice bath protective condition, by ultrasonic stirrer with the output rating of 665-855 by prepared emulsion fine crankshaft 30s-10min; Finally adopt Rotary Evaporators to remove volatile solvent and obtain composite Nano tinting material.
3. the preparation method of water-based composite Nano tinting material as claimed in claim 2, it is characterized in that, described solvent dye is solvent-borne type azoic dyestuff or anthraquinone dye.
4. the preparation method of water-based composite Nano tinting material as claimed in claim 3, it is characterized in that, described solvent dye is C.I. solvent black 3, C.I. solvent black 45, C.I. solvent black 27, C.I. solvent red 26, C.I. solvent red 92, C.I. solvent red 27, C.I. solvent red 124, C.I. solvent red 8, C.I. solvent red 91, C.I. solvent red 217, C.I. solvent red 218, C.I. solvent blue 45, C.I. solvent blue 44, C.I. solvent blue 35, C.I. solvent yellow 16 3, C.I. solvent yellow 79, C.I. solvent yellow 83, C.I. solvent yellow 62, any one in curcumine and carotene.
5. the preparation method of water-based composite Nano tinting material as claimed in claim 2, it is characterized in that, described volatile solvent is ethyl acetate or trichloromethane.
6. the preparation method of water-based composite Nano tinting material as claimed in claim 2, it is characterized in that, the steaming time of revolving of described Rotary Evaporators is 30min, and temperature is set as 40 DEG C.
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| CN107474583A (en) * | 2017-07-18 | 2017-12-15 | 东莞市彩之虹化工有限公司 | A kind of water-based metal Complex dyes and application thereof |
| CN110983456A (en) * | 2019-11-21 | 2020-04-10 | 上海纷然科技有限公司 | Preparation method of composite structure colored nanofiber membrane |
| CN113504365A (en) * | 2021-07-07 | 2021-10-15 | 上海市皮肤病医院 | Colored latex particle, compound, immunochromatography test paper and preparation method thereof |
| CN114342930A (en) * | 2022-03-01 | 2022-04-15 | 中国农业科学院植物保护研究所 | Pesticide nanocapsule and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106083495A (en) * | 2016-06-17 | 2016-11-09 | 中国工程物理研究院化工材料研究所 | Coated explosive microsphere that the solidification of a kind of emulsion prepares and preparation method thereof |
| CN106083495B (en) * | 2016-06-17 | 2018-02-06 | 中国工程物理研究院化工材料研究所 | Coated explosive microballoon that a kind of emulsion solidification is prepared and preparation method thereof |
| CN107474583A (en) * | 2017-07-18 | 2017-12-15 | 东莞市彩之虹化工有限公司 | A kind of water-based metal Complex dyes and application thereof |
| CN110983456A (en) * | 2019-11-21 | 2020-04-10 | 上海纷然科技有限公司 | Preparation method of composite structure colored nanofiber membrane |
| CN113504365A (en) * | 2021-07-07 | 2021-10-15 | 上海市皮肤病医院 | Colored latex particle, compound, immunochromatography test paper and preparation method thereof |
| CN114342930A (en) * | 2022-03-01 | 2022-04-15 | 中国农业科学院植物保护研究所 | Pesticide nanocapsule and preparation method thereof |
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Application publication date: 20151028 |