CN112920621A - Method for preparing easily-dispersible pigment from graphene modified C.I. pigment red 179 - Google Patents
Method for preparing easily-dispersible pigment from graphene modified C.I. pigment red 179 Download PDFInfo
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- CN112920621A CN112920621A CN202110108139.8A CN202110108139A CN112920621A CN 112920621 A CN112920621 A CN 112920621A CN 202110108139 A CN202110108139 A CN 202110108139A CN 112920621 A CN112920621 A CN 112920621A
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- 239000000049 pigment Substances 0.000 title claims abstract description 154
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 229910021389 graphene Inorganic materials 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000002356 single layer Substances 0.000 claims abstract description 35
- 238000003756 stirring Methods 0.000 claims abstract description 32
- 239000002002 slurry Substances 0.000 claims abstract description 31
- 238000000227 grinding Methods 0.000 claims abstract description 29
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000001035 drying Methods 0.000 claims abstract description 17
- 238000004537 pulping Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 239000007921 spray Substances 0.000 claims abstract description 10
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 9
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- 238000002360 preparation method Methods 0.000 claims description 19
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- 238000001694 spray drying Methods 0.000 claims description 11
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- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical group CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 6
- YZYASTRURKBPPS-UHFFFAOYSA-N C(CCC(=O)OCCCCCC(C)C)(=O)OCCCCCC(C)C.[Na] Chemical compound C(CCC(=O)OCCCCCC(C)C)(=O)OCCCCCC(C)C.[Na] YZYASTRURKBPPS-UHFFFAOYSA-N 0.000 claims description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 5
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- AGGCEDYMGLPKNS-UHFFFAOYSA-N 5,5,6-trimethylundec-3-yne-2,2-diol Chemical group CCCCCC(C)C(C)(C)C#CC(C)(O)O AGGCEDYMGLPKNS-UHFFFAOYSA-N 0.000 claims description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 2
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- 239000002245 particle Substances 0.000 abstract description 59
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- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 3
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- 238000005411 Van der Waals force Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
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- 239000012860 organic pigment Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- ZZSIDSMUTXFKNS-UHFFFAOYSA-N perylene red Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=C(OC=5C=CC=CC=5)C=1)C(=O)C2=CC(OC=1C=CC=CC=1)=C3C(C(OC=1C=CC=CC=1)=CC1=C2C(C(N(C=3C(=CC=CC=3C(C)C)C(C)C)C1=O)=O)=C1)=C2C4=C1OC1=CC=CC=C1 ZZSIDSMUTXFKNS-UHFFFAOYSA-N 0.000 description 2
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- MZGATMQZXLOPEJ-UHFFFAOYSA-N 1-n',1-n'-diethylpropane-1,1-diamine Chemical compound CCC(N)N(CC)CC MZGATMQZXLOPEJ-UHFFFAOYSA-N 0.000 description 1
- KATSEJZYPZQRBH-UHFFFAOYSA-N 4,4,5-trimethylundec-2-yne Chemical compound CCCCCCC(C)C(C)(C)C#CC KATSEJZYPZQRBH-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- 230000016615 flocculation Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010316 high energy milling Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002060 nanoflake Substances 0.000 description 1
- 239000002135 nanosheet Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001935 peptisation Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0022—Wet grinding of 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
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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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0003—Drying, e.g. sprax drying; Sublimation of the solvent
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- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
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- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
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- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
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- 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
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
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- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/20—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the process features
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- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
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- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/48—Non-aromatic cyclic groups
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- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention relates to a method for preparing an easily dispersible pigment by using graphene modified C.I. pigment red 179. Adding single-layer graphene or single-layer graphene oxide powder and a solvent into water, stirring and mixing, adding C.I. pigment red 179, and continuously stirring and pulping to obtain pigment slurry; adding a nonionic surfactant, stirring and pulping, and grinding and dispersing the pulp by a sand mill; and adding an anionic surfactant into the slurry after grinding and dispersing, and drying in a spray dryer to prepare the easily dispersible pigment. The easily-dispersible pigment obtained by modifying the C.I. pigment red 179 by using the graphene has the characteristics of high tinting strength, small particle size, more concentrated particle size distribution and good dispersibility when being applied to paint and ink. The coloring power can reach 129%, the average particle size is reduced from 24.140 μm to 4.482 μm, the particle size distribution is more concentrated, and pigment particles which are soft in texture and easy to disperse are obtained.
Description
Technical Field
The invention belongs to the field of chemistry, and particularly relates to a method for preparing an easily dispersible pigment by using graphene modified C.I. pigment red 179.
Background
The C.I. pigment red 179 is prepared by condensation reaction of 3,4,9, 10-perylenetetracarboxylic anhydride and methylamine. The pigment is the most industrially valuable pigment variety of perylene red pigments, has bright red color, excellent organic solvent resistance and thermal stability, and excellent light fastness, weather fastness, bleeding resistance and migration fastness. The method is mainly used for coloring high-grade industrial coatings such as automobile original finishing paints and refinishing paints and high-grade plastics such as vinyl polymers, polyethylene, polypropylene and fiber plastics. And the special structure of a condensed ring pi-pi conjugated system is provided, so that the photoelectric performance is excellent. The product can be used as a fluorescent center of a solar collector and a laser dye, is used for electronic photography and solar cell materials by utilizing the excellent photoconductive performance of the product, and has wide application prospect. The invention relates to a method for improving application performance of pigment red 179 by using graphene or graphene oxide modified pigment red. The molecular structure of the C.I. pigment red 179 is planar, and the pigment red is easily compounded with graphene oxide or graphene through pi-pi action to obtain an easily dispersible pigment, so that the performance of the pigment red in coatings, printing ink and other application systems can be enhanced.
There are many common methods for modifying and dispersing c.i. pigment red 179, for example, the surface treatment of pigments with fine pigment derivatives, their formation of mixed compositions with pigments, and the use of derivatives synthesized from perylenetetracarboxylic anhydride and N, N-diethylpropanediamine, make it possible to improve the deflocculation ability of the c.i. pigment red 179 (US 4762569). High-transparency yellow-light red pigments can be prepared by modifying them with naphthalene anhydride or iron N, N' -bis (2-sulfoethyl) -1,4,5, 8-naphthalenetetracarboxylic acid amide salts (U.S. Pat. No. 5,6015458). Of course, whether this treatment improves the properties of the pigment depends on the system, i.e. the properties are influenced by the resins and solvents used in the application. For some systems, surface treatment of the pigments with the aforementioned derivatives is not effective. The pigment must be compatible with the application system to achieve the change in pigment properties. Other common strategies for improving the performance of organic pigments are surface modification by the addition of auxiliaries, such as cocamidopropyl betaine, dodecyldimethylamine oxide, etc. However, regardless of which type of dispersant is selected, consideration must be given to the actual application of the pigment or the end use of its preparation. The pigment surface modified by the aid can only improve the performance of the pigment within a certain range, but cannot improve the tinting strength of the pigment and the particle size and distribution of the pigment fundamentally.
The invention provides preparation of easily dispersible C.I. pigment red 179 by taking graphene as a modifier, which can prepare easily dispersible pigment with high tinting strength, small particle size and more concentrated particle size distribution. Graphene is a two-dimensional product in which carbon elements are tightly bonded to each other to form a hexagonal lattice. It is an allotrope of carbon, in sp2Bonded atomic planes, molecular bondsThe length is 0.142 nm. The individual graphene layers in graphite are held together by van der waals forces. Graphene is the thinnest compound known to humans, only one atom thick, the lightest material known today, the strongest compound in the material, the best conductor of heat at room temperature and also the best known conductor of electricity. Graphene oxide is an oxide of graphene, containing a variety of oxygen-based functional groups, including hydroxyl, alkoxy, carbonyl, and carboxylic acid groups. These oxygen-containing groups impart graphene oxide with many advantages, including higher solubility and the possibility of surface functionalization. This greatly expands the application range of graphene. According to the similarity of molecular structures, graphene and graphene oxide can be effectively combined with pigments through covalent bonds and non-covalent interactions. Non-covalent interactions are pi-pi conjugation, van der Waals interactions and hydrogen bonding. The key technology of the preparation method is how to combine graphene and graphene oxide with C.I. pigment red 179 with planarity and molecular structure symmetry, so that fine two-dimensional graphene is inserted into a pigment lattice to realize the assembly of graphene and pigment, and the assistance of a surfactant is added, thereby providing the easily-dispersible pigment with extremely excellent performance.
Disclosure of Invention
According to the similarity of molecular structures, graphene and graphene oxide are effectively combined with C.I. pigment red 179 through non-covalent acting force pi-pi conjugate acting force, hydrogen bond acting force and van der Waals force. Mixing single-layer graphene or single-layer graphene oxide with the pigment, stirring and pulping, grinding and dispersing by a sand mill, adding a surfactant, and drying in a spray dryer to prepare the easily-dispersible pigment containing graphene.
Graphene generally exists in a monomolecular form, and there are different classes of graphene, and among known graphene materials, there are single-layer to multi-layer graphene, graphite nanoplatelets, nanosheets, nanoflakes, graphene oxide, and the like. Most of the reports in the literature use graphite nanoplatelets, or graphene oxide. However, due to their poor solubility in various types of solvents and due to the hydrophobic nature of graphene, it is often necessary to add stabilizers or surfactants to improve the dispersion of graphene when applied.
The particles of organic pigments can then be broken down into primary particles or flocs, which are dispersed into the medium by high energy milling to provide superior color strength. These fine pigment particles are generally planar and tend to flocculate and lose the desired level of tinting strength, gloss and clarity. The particles of perylene red c.i. pigment red 179 are very susceptible to flocculation and therefore must be surface treated to improve their color strength, color appearance, and particle dispersibility. C.i. pigment red 179 pigment crystal structure is planar or nearly planar and can be surface treated with single layer graphene to improve its color properties.
The invention relates to a preparation method of graphene modified C.I. pigment red 179, which comprises the following steps:
(1) adding single-layer graphene or single-layer graphene oxide powder and a solvent into water, stirring and mixing for 1-2h, adding C.I. pigment red 179 for 0.5-1h, and continuously stirring and pulping for 0.5-1h to obtain pigment slurry;
(2) adding a nonionic surfactant, stirring and pulping for 0.5-1h, and grinding and dispersing the pulp by a sand mill;
(3) and adding an anionic surfactant into the slurry after grinding and dispersing, and drying in a spray dryer to prepare the easily dispersible pigment.
The technical process adopted by the invention is as follows: the preparation method of the graphene modified C.I. pigment red 179 specifically comprises the following steps:
(1) preparation of pigment slurries
Adding single-layer graphene or single-layer graphene oxide powder and a solvent into water, stirring and mixing for 1-2h, adding C.I. pigment red 179 for 0.5-1h, and continuously stirring and pulping for 0.5-1h to obtain pigment slurry;
the medium used in the present invention is water plus a small amount of solvent, the water used is deionized water, the solvent is N-octyl pyrrolidone, and the solvent has both a wetting effect and a surface tension reducing effect. The mass ratio of the solvent to the water is as follows: 0.1-0.5: 100.
The mass ratio of the single-layer graphene or the single-layer graphene oxide to the C.I. pigment red 179 to the water is as follows: 1-3: 100: 1000.
(2) grinding
Adding nonionic surfactant, stirring and pulping for 0.5-1 hr, pumping the mixture into sand mill, and sand-milling to disperse until particle size reaches below 1 μm.
The diameter of the zirconium beads used in the sand mill is 0.6-1.0mm, the grinding temperature is 10-40 ℃, and the zirconium beads are ground for 2-4h at the temperature.
The common nonionic surfactant is unsaturated alcohol or fatty alcohol-polyoxyethylene ether; such as tetramethyldecynediol, fatty alcohol-polyoxyethylene ethers. The addition amount of the nonionic surfactant is 1-3% of the pigment. Surfactants are used in combination with the graphene and pigments of the present invention.
A sand mill is a device that grinds or disperses a pigment mixture into a fine slurry by stirring a grinding medium (steel balls, zirconium beads, or polymeric grinding beads) in a cylindrical container. The rotation of the sand mill produces bead collisions, causing intense shear forces and impacting the particles of the pigment mixture. Can effectively reduce micron or submicron-sized particles into countless nanometer-sized fine particles. By optimizing the size of the grinding beads, the energy and impact force of the grinding material can be optimized by adjusting the rotation speed.
(3) Drying
And adding an anionic surfactant into the ground slurry, and drying by using a spray dryer to obtain the easily-dispersible pigment.
Suitable anionic surfactants include sodium lauryl sulfate, sodium diisooctyl succinate sulfonate, and the like. The amount of anionic surfactant added is 2-4% of the pigment.
The milled pigment slurry can be spray dried to produce an easily dispersible pigment. The slurry is sprayed out in relatively large droplets and the water is evaporated to form fine spherical particles. The inlet gas temperature in spray drying is typically 130-300 deg.C, preferably 150-170 deg.C, and the gas outlet temperature is 70-150 deg.C, preferably 90-100 deg.C.
The easily-dispersible pigment obtained by modifying the C.I. pigment red 179 by using the graphene has the characteristics of high tinting strength, small particle size, more concentrated particle size distribution and good dispersibility when being applied to paint and ink. Compared with the C.I. pigment red 179, the easily dispersible pigment obtained by modifying the C.I. pigment red 179 by using the graphene has the advantages that the tinting strength can reach 129%, the average particle size is reduced from 24.140 mu m to 4.482 mu m, the particle size distribution is more concentrated, and the pigment particles which are soft in texture and easy to disperse are obtained.
Drawings
Fig. 1 shows the particle size distribution plot for an unmodified c.i. pigment red 179 sample.
Fig. 2 shows the particle size distribution plot for a sample of 1% single layer graphene modified c.i. pigment red 179.
Fig. 3 shows the particle size distribution plot for the 3% single layer graphene modified c.i. pigment red 179 sample.
Fig. 4 shows the particle size distribution plot for a 3% monolayer graphene oxide modified c.i. pigment red 179 sample.
Fig. 5 shows a scanning electron micrograph of an unmodified c.i. pigment red 179 sample.
Fig. 6 shows a scanning electron micrograph of a sample of 1% single layer graphene modified c.i. pigment red 179.
Fig. 7 shows a scanning electron micrograph of a sample of c.i. pigment red 179 modified with 3% single layer graphene.
Fig. 8 shows a scanning electron micrograph of a 3% monolayer graphene oxide modified c.i. pigment red 179 sample.
Detailed Description
The following examples illustrate the practice of the invention, but the method should not be construed to limit the scope of the invention in any way.
Example 1
Preparation of easily dispersible pigment from 1% single-layer graphene modified C.I. pigment Red 179
(1) Preparation of pigment slurries
Adding 1g of single-layer graphene powder and 1g N-octyl pyrrolidone into 1000g of deionized water, and stirring and mixing for 1 h; 100g of pigment red 179 is added for 0.5h, and stirring and beating are continued for 0.5h to obtain pigment slurry.
(2) Grinding
Adding 1g of tetramethyl decyne glycol, stirring and pulping for 0.5h, pumping the mixture into a sand mill, and sanding until the particle size reaches below 1 mu m; the zirconium beads used in the sand mill had a diameter of 1.0mm, a milling temperature of 40 ℃ and milling at this temperature for 2 h.
(3) Drying
After the grinding is finished, 2g of sodium diisooctyl succinate sulfonate is added into the grinding slurry, the mixture is uniformly stirred and then spray-dried, wherein the air inlet temperature in the spray-drying process is usually 150 ℃ and the gas outlet temperature is 90 ℃. And drying to obtain the graphene modified C.I. pigment red 179 easily-dispersible pigment. The results of the examination showed a tinting strength of 120% (compared with c.i. pigment red 179), an average particle diameter of 4.975 μm, a particle size distribution as shown in fig. 2, and a scanning electron micrograph as shown in fig. 6. The particle size was smaller than that of the sample of unmodified c.i. pigment red 179 (average particle size 24.140 μm, particle size distribution as shown in fig. 1, and scanning electron micrograph as shown in fig. 5). The particle size distribution diagram and the scanning electron microscope image show that the modified easily-dispersible pigment has smaller particle size, more concentrated particle size distribution and soft pigment particle texture.
Example 2
Preparation of easily dispersible pigment from 2% single-layer graphene modified C.I. pigment red 179
(1) Preparation of pigment slurries
Adding 2g of single-layer graphene powder and 3g N-octyl pyrrolidone into 1000g of deionized water, and stirring and mixing for 1.5 h; 100g of pigment red 179 is added for 0.8h, and stirring and beating are continued for 1h to obtain pigment slurry.
(2) Grinding
2g of tetramethyldecyndiol is added, then the mixture is stirred and beaten for 0.8h, and the mixture is pumped into a sand mill and sanded until the particle size reaches below 1 μm. The zirconium beads used in the sand mill had a diameter of 0.8mm, a milling temperature of 30 ℃ and milling at this temperature for 3 h.
(3) Drying
After completion of the milling, 4g of sodium lauryl sulfate was added to the milled slurry, stirred uniformly, and then spray-dried, the inlet gas temperature in the spray-drying being usually 170 ℃ and the gas outlet temperature being 100 ℃. And drying to obtain the graphene modified C.I. pigment red 179 easily-dispersible pigment.
Example 3
Preparation of easily dispersible pigment from 3% single-layer graphene modified C.I. pigment Red 179
(1) Preparation of pigment slurries
Adding 3g of single-layer graphene powder and 5g N-octyl pyrrolidone into 1000g of deionized water, and stirring and mixing for 2 hours; 100g of pigment red 179 is added for 1 hour, and stirring and pulping are continued for 0.8 hour to obtain pigment slurry.
(2) Grinding
3g of tetramethyldecynediol was added, followed by stirring and beating for 1 hour, and this mixture was pumped into a sand mill and sanded until the particle size reached below 1 μm. The zirconium beads used in the sand mill had a diameter of 0.6mm, a milling temperature of 20 ℃ and milling at this temperature for 4 h.
(3) Drying
After the grinding is completed, the grinding slurry is added into 3g of sodium diisooctyl succinate sulfonate, the mixture is uniformly stirred and then spray-dried, wherein the air inlet temperature in the spray-drying process is generally 160 ℃, and the gas outlet temperature is 90 ℃. The graphene modified C.I. pigment red 179 easily dispersible pigment is obtained. The results of the examination showed a tinting strength of 129% (compared with c.i. pigment red 179) and an average particle size of 4.482 μm, the particle size distribution is shown in fig. 3, and the scanning electron micrograph is shown in fig. 7. The particle size was much smaller than that of the unmodified c.i. pigment red 179 sample, the particle size distribution was more concentrated, and the pigment particles were fluffy in texture.
Example 4
Preparation of easily dispersible pigment from 1% single-layer graphene oxide modified C.I. pigment red 179
(1) Preparation of pigment slurries
Adding 1g of single-layer graphene oxide powder and 2g N-octyl pyrrolidone into 1000g of deionized water, and stirring and mixing for 1 h; 100g of pigment red 179 is added for 0.5h, and stirring and beating are continued for 0.5h to obtain pigment slurry.
(2) Grinding
Adding 2g of fatty alcohol-polyoxyethylene ether (AEO-7), stirring and pulping for 0.5h, pumping the mixture into a sand mill, and sanding until the particle size reaches below 1 mu m; the zirconium beads used in the sand mill had a diameter of 0.6mm, a milling temperature of 10 ℃ and milling at this temperature for 3 h.
(3) Drying
After grinding, adding 2g of sodium lauryl sulfate into the grinding slurry, uniformly stirring, and then performing spray drying, wherein the air inlet temperature in the spray drying is usually 150 ℃, and the gas outlet temperature is 90 ℃; the graphene oxide modified C.I. pigment red 179 easily-dispersible pigment is obtained.
Example 5
Preparation of easily dispersible pigment from 2% single-layer graphene oxide modified C.I. pigment red 179
(1) Preparation of pigment slurries
Adding 2g of single-layer graphene oxide powder and 3g N-octyl pyrrolidone into 1000g of deionized water, and stirring and mixing for 1.5 h; 100g of pigment red 179 is added for 1 hour, and stirring and pulping are continued for 0.7 hour to obtain pigment slurry.
(2) Grinding
3g of tetramethyldecynediol was added, followed by stirring and beating for 1 hour, and this mixture was pumped into a sand mill and sanded until the particle size reached below 1 μm. The zirconium beads used in the sand mill had a diameter of 0.6mm, a milling temperature of 30 ℃ and milling at this temperature for 4 h.
(3) Drying
After grinding is finished, adding 3g of sodium diisooctyl succinate sulfonate into the grinding slurry, uniformly stirring, and then performing spray drying, wherein the air inlet temperature in the spray drying is usually 170 ℃, and the gas outlet temperature is 100 ℃; the graphene oxide modified C.I. pigment red 179 easily-dispersible pigment is obtained.
Example 6
Preparation of easily dispersible pigment from 3% single-layer graphene oxide modified C.I. pigment red 179
(1) Preparation of pigment slurries
3g of single-layer graphene oxide powder and 4g N-octyl pyrrolidone are added into 1000g of deionized water, and stirred and mixed for 2 hours. 100g of pigment red 179 is slowly added, and stirring and beating are continued for 1h to obtain pigment slurry.
(2) Grinding
2g of fatty alcohol-polyoxyethylene ether (AEO-7) is added, then stirring and beating are carried out for 0.7h, and the mixture is pumped into a sand mill for sand grinding until the particle size reaches below 1 mu m. The zirconium beads used in the sand mill had a diameter of 0.8mm, a milling temperature of 30 ℃ and milling at this temperature for 4 h.
(3) Drying
After completion of the milling, 4g of sodium lauryl sulfate was added to the milled slurry, stirred uniformly, and then spray-dried, the inlet gas temperature in the spray-drying being usually 150 ℃ and the gas outlet temperature being 100 ℃. The graphene oxide modified C.I. pigment red 179 easily-dispersible pigment is obtained. The test result showed 125% coloring power (compared with c.i. pigment red 179) and an average particle diameter of 4.843 μm. The particle size distribution diagram is shown in figure 4, and the scanning electron micrograph is shown in figure 8. The particle size was much smaller than that of the unmodified c.i. pigment red 179 sample, the particle size distribution was more concentrated, and the pigment particles were fluffy in texture.
The obtained pigment product is subjected to performance test by selecting the type of the pigment product:
(1) 0.1g of pigment and 1.0g of titanium dioxide are weighed, 1mL of varnish is extracted by an injector, and the varnish is ground three times on a flat grinder, 50 revolutions each time. The ground ink was scraped and the coloring power was measured with a color meter.
(2) The particle size and the distribution of the prepared easily-dispersible pigment before and after modification are tested and compared by adopting a laser nanometer particle size analyzer.
(3) The particle morphology of the easily dispersible pigment is determined by a scanning electron microscope with the magnification of 5 ten thousand times.
The test results are shown in table 1:
TABLE 1 tinting strength and particle size of the pigments
It can be seen from table 1 that the tinctorial strength of the graphene-and graphene oxide-modified pigment red 179 is improved and the pigment particle size is significantly reduced. The particle size and distribution diagram of the pigment red 179 before and after the modification of the single-layer graphene and the single-layer graphene oxide and the scanning electron microscope image are shown in the attached drawings 1-8 in the specification, and according to the particle size distribution and the scanning electron microscope image, the particle size distribution of the pigment red 179 after the modification of the single-layer graphene and the single-layer graphene oxide is more concentrated, the particle size is smaller, and the pigment particles are soft.
The above examples are intended to illustrate the disclosed embodiments of the invention and are not to be construed as limiting the invention. In addition, various modifications of the methods and compositions set forth herein, as well as variations of the methods and compositions of the present invention, will be apparent to those skilled in the art without departing from the scope and spirit of the invention. While the invention has been specifically described in connection with various specific preferred embodiments thereof, it should be understood that the invention should not be unduly limited to such specific embodiments. Indeed, various modifications of the above-described embodiments which are obvious to those skilled in the art to which the invention pertains are intended to be covered by the scope of the present invention.
Claims (9)
1. A method for preparing an easily dispersible pigment using graphene modified c.i. pigment red 179, comprising the operations of:
(1) preparation of pigment slurries
Adding single-layer graphene or single-layer graphene oxide powder and a solvent into water, stirring and mixing for 1-2h, adding C.I. pigment red 179 for 0.5-1h, and continuously stirring and pulping for 0.5-1h to obtain pigment slurry;
(2) grinding
Adding a nonionic surfactant, stirring and pulping for 0.5-1h, and grinding and dispersing the pulp by a sand mill;
(3) drying
And adding an anionic surfactant into the slurry after grinding and dispersing, and drying in a spray dryer to prepare the easily dispersible pigment.
2. The process as claimed in claim 1, wherein the medium is water plus a small amount of solvent, the water used is deionized water, and the solvent is N-octyl pyrrolidone; the mass ratio of the solvent to the water is as follows: 0.1-0.5: 100.
3. The method of claim 1, wherein the mass ratio of the single-layer graphene or single-layer graphene oxide to the c.i. pigment red 179 and water is: 1-3: 100: 1000.
4. the method as set forth in claim 1, wherein the nonionic surfactant used in the step (2) is an unsaturated alcohol or a fatty alcohol-polyoxyethylene ether; the addition amount of the nonionic surfactant is 1-3% of the pigment.
5. The method as set forth in claim 1, wherein the nonionic surfactant is tetramethyldecyndiol or fatty alcohol polyoxyethylene ether.
6. The method as set forth in claim 1, wherein the zirconium beads used in the sand mill of the step (2) have a diameter of 0.6 to 1.0mm, a milling temperature of 10 to 40 ℃, and milling for 2 to 4 hours at the milling temperature.
7. The method of claim 1, wherein the suitable anionic surfactant in step (3) is sodium lauryl sulfate or sodium diisooctyl succinate sulfonate; the addition amount is 2-4% of the pigment amount.
8. The method as set forth in claim 1, wherein the step (3) is drying using a spray dryer; the inlet air temperature in spray drying in the spray dryer is usually 130-300 ℃; and the gas outlet temperature is 70-150 ℃.
9. The method as set forth in claim 1, wherein the step (3) is drying using a spray dryer; the air inlet temperature in the spray drying in the spray dryer is 150-170 ℃; the gas outlet temperature is 90-100 ℃.
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