CN116836567B - Preparation method of dust-free pigment - Google Patents
Preparation method of dust-free pigment Download PDFInfo
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- CN116836567B CN116836567B CN202311122823.7A CN202311122823A CN116836567B CN 116836567 B CN116836567 B CN 116836567B CN 202311122823 A CN202311122823 A CN 202311122823A CN 116836567 B CN116836567 B CN 116836567B
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- pigment
- dust
- stirring
- water
- series
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- 239000000049 pigment Substances 0.000 title claims abstract description 159
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 239000000843 powder Substances 0.000 claims abstract description 23
- 238000001291 vacuum drying Methods 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 43
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 43
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 24
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 24
- 238000001035 drying Methods 0.000 claims description 20
- 239000012065 filter cake Substances 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- -1 aminoethoxy Chemical class 0.000 claims description 17
- 125000000129 anionic group Chemical group 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 17
- 229920002521 macromolecule Polymers 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 239000007900 aqueous suspension Substances 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000012860 organic pigment Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 230000001105 regulatory effect Effects 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- OPGOVMSKPDWRRQ-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound Cc1ccc(cc1)S(=O)(=O)OCCOCCOCCOCCOCCOCCOCCO OPGOVMSKPDWRRQ-UHFFFAOYSA-N 0.000 claims description 6
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- 229940099800 pigment red 48 Drugs 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 101100496858 Mus musculus Colec12 gene Proteins 0.000 claims description 3
- WNVDZDLVUGYYKK-HBGYKRQNSA-K C.I. Pigment Yellow 100 Chemical compound OC(=O)C1=NN(C(=O)C1\N=N\c1ccc(cc1)S(=O)(=O)O[Al](OS(=O)(=O)c1ccc(cc1)\N=N\C1C(=O)N(N=C1C(O)=O)c1ccc(cc1)S(O)(=O)=O)OS(=O)(=O)c1ccc(cc1)\N=N\C1C(=O)N(N=C1C(O)=O)c1ccc(cc1)S(O)(=O)=O)c1ccc(cc1)S(O)(=O)=O WNVDZDLVUGYYKK-HBGYKRQNSA-K 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 235000010187 litholrubine BK Nutrition 0.000 claims description 2
- 239000000428 dust Substances 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 11
- 239000013078 crystal Substances 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 238000004040 coloring Methods 0.000 abstract description 6
- 230000036541 health Effects 0.000 abstract description 5
- 229910021645 metal ion Inorganic materials 0.000 abstract description 5
- 239000003973 paint Substances 0.000 abstract description 5
- 239000004033 plastic Substances 0.000 abstract description 5
- 229920003023 plastic Polymers 0.000 abstract description 5
- 238000004806 packaging method and process Methods 0.000 abstract description 4
- 238000007639 printing Methods 0.000 abstract description 4
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 230000001788 irregular Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 6
- 239000004595 color masterbatch Substances 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 238000005411 Van der Waals force Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000001038 titanium pigment Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 1
- OSSZFTJQTIEJDM-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid;sodium Chemical compound [Na].CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl OSSZFTJQTIEJDM-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- FHXUYFKYRBLZJU-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(S(O)(=O)=O)=C1 FHXUYFKYRBLZJU-UHFFFAOYSA-N 0.000 description 1
- VFMNIJOKAXPZLE-UHFFFAOYSA-N 4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1 VFMNIJOKAXPZLE-UHFFFAOYSA-N 0.000 description 1
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007592 spray painting technique Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0009—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives
- C09B67/001—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives containing resinic acid derivatives
-
- 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
- C09B63/005—Metal lakes of dyes
-
- 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
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0011—Coated particulate pigments or dyes with organic coatings containing amine derivatives, e.g. polyamines
-
- 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
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0092—Dyes in solid form
- C09B67/0094—Treatment of powders, e.g. antidusting
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention discloses a preparation method of a dust-free pigment, which belongs to the technical field of pigments, wherein the dust-free pigment is adsorbed and adjusted by adding a treating agent in a crystal adjusting link, and then pH is adjusted or Ca is introduced 2+ ，Ba 2+ ，Sr 2+ ，Mg 2+ ，Mn 2+ Coating is completed by salifying or laking the pigment with metal ions, agglomerating and separating the pigment from an aqueous medium, and finally, obtaining dust-free pigment powder by vacuum drying; the effective content of the dust-free pigment prepared by the invention is 85-90%, and the pigment can be used for coloring in the fields of printing ink/paint and plastics; the pigment is easy to disperse, high in transparency and capable of effectively protecting the operation environment and human health, and the tinting strength is 95% -100% of that of the corresponding traditional pigment, and no dust flies in the packaging and metering processes.
Description
Technical Field
The invention belongs to the technical field of pigments, and particularly relates to a preparation method of a dust-free pigment.
Background
The pigment is mainly used as a colorant for coloring plastics, printing ink and paint. In the above applications, a good dispersion is required to obtain a satisfactory application result. However, the conventional powder azo pigments always have the following problems: 1) Dust is big: the powder pigment has the problem of dust flying in the packaging and application processing processes, and damages the environment to clean and endanger the health of human bodies; 2) Poor dispersibility: traditional powder pigments in plastic, ink and paint applications require a strong mechanical force for a long time to grind and disperse, even by using a strong mechanical grinding device such as a sand mill. The tinting properties of the pigments are thus not fully exploited and add to the cost of application and processing for downstream users.
The prior art has adopted the preparation of pigment preforms to solve the above-mentioned problems. And (3) carrying out water squeezing phase change on the pigment water-containing filter cake and resin or other hydrophobic medium in a kneader to obtain the pigment preparation of the mixed resin. Patent application CN115594989 a discloses a preparation method of polyamide pigment preparation, which comprises the steps of carrying out water squeezing and phase conversion on polyamide resin, pigment and auxiliary agent, transferring pigment in water phase into polyamide organic phase, separating water rapidly after water squeezing and phase conversion is completed, drying the preparation, adding liquid nitrogen, and pulverizing the prepared preparation into colored sand or pressed color flakes at low temperature.
Another solution is to make pigments into color master batches. The pigment and low molecular weight PP (polypropylene), PE (polyethylene) and other resins are melted and mixed at high temperature, extruded by a screw extruder and pelletized to obtain the color master batch. Patent CN 101891973B discloses a special titanium pigment for color master batch
The titanium pigment prepared by the method has excellent dry powder fluidity, and is convenient for air flow transportation and mixing; patent application CN110903502a provides a method for preparing high-transmittance organic pigment coloring masterbatch, which improves the dispersion of high-transmittance organic pigment material particles in a resin matrix; the prepared color master batch can solve the dust problem, also provides convenience for application, but only solves the dust problem when the user applies, does not solve the problem that pigment manufacturers crush and pack dust and the initial batching dust of master batch manufacturers, and the effective pigment content is less than 45 percent, so that the color master batch can only be used for coloring plastics.
Still another solution is to make the pigment cake directly into aqueous color paste. The product also has low content, usually less than 30%, and can only be used in the fields of spray painting, fabric pigment dyeing and printing, other water-based paint and the like.
In recent years, polymer-coated pigments have been developed in many cases. Patent CN109836853a discloses a polymer coated aluminum pigment, which is obtained by mixing and dispersing flaky aluminum particles and a solvent, and carrying out solid-liquid separation to obtain a filter cake; mixing a filter cake, a reaction monomer with carboxyl and a silane coupling agent, adding a pH regulator until the pH value of the system is 7.5-8.5, stirring, continuing to add the reaction monomer and the catalyst under the protection of nitrogen, adding an initiator for in-situ polymerization coating, then preserving heat, cooling, washing and filtering to obtain the polymer coated aluminum pigment; the method can solve the dust problem of powder pigment, but adds a one-step polymerization reaction, needs to establish a new reaction device, has low pigment effective content which is generally less than 70%, and has different production environments and different safety requirements compared with the traditional diazotization coupling reaction, thus requiring larger investment and increasing production cost.
The scheme is that the powder pigment or pigment filter cake is used as the starting material for reprocessing preparation, new production devices and sites are required to be built, and the prepared pigment has the problems of low pigment content, strong speciality, high transportation and storage cost and the like.
Aiming at the problems, research on clean preparation technology solves the powder pigment dust problem, protects the environment, protects the health of the producer, and provides dust-free and easily-dispersible powder pigment for downstream users, which is the direction of the industry staff.
Disclosure of Invention
In order to solve the problems, the invention aims to provide a preparation method of a dust-free pigment.
The invention aims to achieve the aim, and the aim is achieved by the following technical scheme:
a method for preparing a dust-free pigment comprising the steps of:
adding water into an azo lake series organic pigment crude product compound obtained after the coupling reaction to obtain a pigment water suspension with the mass concentration of 10%, adding a treating agent into the pigment water suspension, stirring for 1-2 hours to uniformly disperse the pigment water suspension and adsorb the pigment water suspension with the pigment crude product compound, adding an inorganic salt water solution to carry out laking, stirring for 0.5-1 hour, heating to 80-90 ℃ after full laking, adding a dilute hydrochloric acid to adjust the pH of a system to 6-7, continuously stirring for 0.5-1 hour, keeping the pH stable, standing for 2-3 hours after stirring is finished, carrying out vacuum suction filtration, washing an obtained filter cake with water for 2-3 times, and carrying out vacuum drying at 50 ℃ to obtain dust-free pigment powder; wherein the crude pigment is crude azo lake organic pigment;
the treating agent is an emulsion prepared by uniformly stirring and dispersing 10-20 parts of rosin modified anionic macromolecular compound, 20-25 parts of amidated styrene-maleic anhydride copolymer and 200-300 parts of water in parts by weight;
the structural formula of the rosin modified anionic macromolecular compound is as follows:
；
the amidated styrene-maleic anhydride copolymer has the structural formula:
。
the inorganic salt is CaCl 2 、BaCl 2 、SrCl 2 、MgCl 2 Or MnCl 2 。
The mass concentration of the inorganic salt aqueous solution is 20-35%.
The water content of the obtained dust-free pigment powder is less than 3%.
The mass ratio of the organic pigment crude product compound to the treating agent to the inorganic salt aqueous solution is 100: 10-15: 100-320.
The rosin modified anionic macromolecular compound is prepared by the following method:
(1) adding rosin into a reactor, heating to 140-150 ℃ until the rosin is completely melted, adding maleic acid and aluminum trichloride, heating to 200 ℃, and reacting for 5-8 hours to obtain maleic rosin;
the mass ratio of the rosin to the maleic acid to the aluminum trichloride is 1:0.4 to 0.6:0.002 to 0.004;
(2) adding the maleated rosin, the p-toluenesulfonic acid, the ethylene glycol monoallyl ether and the benzoquinone obtained in the step (1) into gasoline, heating to 120-150 ℃, reacting for 5-8 hours, separating out an upper solvent after the reaction is finished, standing for 24-36 hours, washing the separated solid with water at 70-80 ℃ for 3-5 times, and drying to obtain maleated rosin ester;
the mass ratio of the maleated rosin to the p-toluenesulfonic acid to the ethylene glycol monoallyl ether to the benzoquinone to the gasoline is 1:0.01 to 0.02:0.5 to 0.75:0.003 to 0.005: 3-5;
(3) adding the maleated rosin ester, the acrylic sulfonic acid and the azodiisobutyronitrile prepared in the step (2) into chloroform, stirring and dispersing uniformly, adding water into the mixture, heating the mixture to 70-90 ℃, stirring and reacting for 15-24 hours, performing suction filtration after the reaction is finished, regulating the pH of the obtained filter cake to 8 by using 0.1mol/L sodium bicarbonate solution, and drying to obtain a rosin modified anionic macromolecular compound;
the mass ratio of the maleated rosin ester, the acrylic sulfonic acid, the azodiisobutyronitrile, the chloroform and the water is 1: 0.5-1: 0.05-0.1: 5-10: 10-20.
The amidated styrene-maleic anhydride copolymer is prepared according to the following method:
1) Adding 1 part of (ethane-1, 2-diylbis (oxy)) dimethylamine into 5-10 parts of dichloromethane, adding 1.5-1.8 parts of di-tert-butyl dicarbonate, reacting for 2-6 hours at 25-30 ℃, and distilling under reduced pressure to remove dichloromethane after the reaction is finished to obtain dimethylamine derivatives with one end of amine groups protected;
the mass ratio of the (ethane-1, 2-diylbis (oxy)) dimethylamine to the methylene dichloride to the di-tert-butyl dicarbonate is 1: 5-10: 1.5-1.8;
2) Adding the dimethylamine derivative with one amine group protected in the step 1), heptaethylene glycol mono-p-toluenesulfonate and potassium carbonate into acetonitrile, stirring and dissolving, heating and refluxing for reaction for 10-20 h, filtering after the reaction is finished, distilling the obtained filtrate under reduced pressure to remove acetonitrile, adding trifluoroacetic acid and dichloromethane into the obtained solid, reacting for 5-10 h at 25-30 ℃, distilling under reduced pressure to remove dichloromethane after the reaction is finished, and drying to obtain an aminoethoxy derivative;
the mass ratio of the dimethylamine derivative with one amine group protected, the heptaethylene glycol mono-p-toluenesulfonate, the potassium carbonate, the acetonitrile, the trifluoroacetic acid and the dichloromethane is 1: 1.5-2: 0.5 to 0.8: 5-10: 0.2-0.3: 5-10;
3) Adding the styrene-maleic anhydride copolymer into cyclohexanone, stirring and dissolving, then adding the aminoethoxy derivative obtained in the step 2), stirring and reacting for 1-2 hours at 90-100 ℃, and distilling under reduced pressure to remove the solvent to obtain an amidated styrene-maleic anhydride copolymer;
the mass ratio of the styrene-maleic anhydride copolymer, the cyclohexanone and the aminoethoxy derivative is 1: 5-10: 2-4.
The azo lake series organic pigment is pigment yellow 62, pigment yellow 104, pigment yellow 133, pigment yellow 169, pigment yellow 168, c.i. pigment yellow 100, pigment yellow 183, pigment yellow 190, pigment yellow 191, c.i. pigment red 48 series, c.i. pigment red 52 series, c.i. pigment red 57 series, c.i. pigment orange 17 series, pigment orange 18 series, pigment orange 19 series, pigment orange 46 series, pigment red 49 series, pigment red 50 series, or pigment red 53 series.
The crude organic pigment compound is a product obtained after the coupling reaction is finished, filtering and drying the obtained filter cake; the crude pigment compound is not subjected to a crystal adjustment treatment process; the crystal adjustment treatment process is a pigment lake process.
The preparation method of the dust-free pigment comprises the steps of adding a treating agent to the crystal adjustment treatment process of the traditional preparation process known in the industry for adsorption and crystal adjustment, adsorbing the treating agent on the surfaces of pigment particles by virtue of Van der Waals force, and preventing aggregation of the pigment particles in the crystal growth process; after that, by adjusting pH and introducing Ca 2+ ，Ba 2+ ，Sr 2+ ，Mg 2+ ，Mn 2+ The metal ions form salt to be precipitated and complete the coating of the treating agent, so that the metal ions are agglomerated and separated from the aqueous medium, and finally the dust-free pigment powder is obtained through vacuum drying.
The treating agent used in the invention is a compound of rosin modified anionic macromolecular compound and amidated styrene-maleic anhydride copolymer, the rosin modified anionic macromolecular compound contains a large amount of carboxylate radicals and sulfonate radicals, and can be introduced with a lake pigment in Ca 2+ ，Ba 2+ ，Sr 2+ ，Mg 2+ ，Mn 2+ The metal ions are together precipitated, deposited and coated on the surface of the pigment to form loose agglomerates which are agglomerated and separated from a saline water medium, and the amidated styrene-maleic anhydride copolymer contains hydrophobic long carbon chains and styrene chain segments in the structure and hydrophilic-COOH, -CONH-and-CH 2 CH 2 O-, can obviously change the tension of the pigment surface, and in addition, the molecular structure of the O-can take the shape of a comb and has the surface of dispersed particlesThe coating and encapsulation effects are good, so that the coating is uniformly adsorbed and deposited on the surface of the pigment to form a protective film with weak hydrophilicity, and fine pigment particles are loosely aggregated to realize dust-free effect.
Compared with the prior art, the invention has the following advantages:
the invention is in the crystallization modification link (namely the pigmenting link) of the existing azo pigment preparation process
The compound of rosin modified anionic macromolecular compound and amidated styrene-maleic anhydride copolymer is added as treating agent, and is adsorbed onto pigment surface by means of Van der Waals force with pigment, pH is regulated and Ca is added 2+ ，Ba 2+ ，Sr 2+ ，Mg 2+ ，Mn 2+ The metal ions enable the treating agent to form salt, and the physical processes such as precipitation and the like realize the coating and precipitation separation of the small particle pigment; finally, powder dust-free pigment is obtained by adopting a vacuum drying method, so that reagglomeration in the pigment drying process is avoided, and the dispersibility of the pigment is effectively protected; the preparation technology related by the invention does not involve the addition of a production device, has less water washing quantity, simple preparation process and low production cost, and does not produce secondary pollution.
The dust-free powder pigment prepared by the invention is loose irregular granular powder, the effective content of the pigment is 85-90%, and the pigment can be used for coloring in the fields of printing ink, paint, plastic and the like; the pigment is easy to disperse, high in transparency and capable of effectively protecting the operation environment and human health, and the tinting strength is 95% -100% of that of the corresponding traditional pigment, so that the pigment has good wetting dispersibility in an aqueous application medium, and no dust flies in the packaging and metering processes; compared with the traditional powder pigment, the powder pigment has smaller bulk density and good dispersibility, does not need grinding in downstream application, and can realize full dispersion and full display of the coloring performance by only stirring at a high speed.
The preparation technology is completed through the adsorption, encapsulation and flocculation of the treating agent on pigment fine particles in the crystal adjustment link of the traditional production process, belongs to the physical process, and does not add other chemical reaction links. Has great universality and has guiding significance on other high-performance pigments such as heterocycle, condensed ring and the like.
Detailed Description
The foregoing is further elaborated by the following description of embodiments of the present invention, which are given by way of example only, and should not be construed as limiting the scope of the present invention. All techniques implemented based on the above description of the invention are within the scope of the invention.
The styrene-maleic anhydride copolymer in the following examples was purchased from the pharmaceutical chemicals Co., ltd, and has a molecular weight of 7500 to 10000.
Example 1 preparation of rosin-modified anionic macromolecular compounds:
(1) adding 0.1kg of rosin into a reactor, heating to 140 ℃ until the rosin is completely melted, adding 0.04kg of maleic acid and 0.2g of aluminum trichloride, heating to 200 ℃, and reacting for 5 hours to obtain maleic rosin;
(2) adding 0.1kg of maleic rosin, 0.001kg of p-toluenesulfonic acid, 0.05kg of ethylene glycol monoallyl ether and 0.3g of benzoquinone into 0.3kg of gasoline, heating to 120 ℃, reacting for 5 hours, separating out an upper solvent after the reaction is finished, standing for 24 hours, washing the separated solid with water at 70 ℃ for 3 times, and drying to obtain a maleic rosin ester; 1 H NMR(400 MHz, DMSO-d 6 , 298 K) δ12.11 (s, 1H), 5.98-6.03(m, 2H), 5.38(d, 2H), 5.31(s, 1H), 5.29(d, 2H), 4.21(t, 4H), 4.0(d, 4H), 3.55(t, 4H), 2.81-2.90(m, 1H), 2.77(d, 1H), 2.24-2.65(m, 2H), 1.30-1.87(m, 13H), 1.13(s, 3H), 1.07(t, 1H), 0.90(d, 6H), 0.72 (s, 3H)。
(3) adding 0.1kg of maleic rosin ester, 0.05kg of propylene sulfonic acid and 0.005kg of azodiisobutyronitrile into 0.5kg of chloroform, stirring and dispersing uniformly, adding 1kg of water into the mixture, heating to 70 ℃, stirring and reacting for 15 hours, filtering after the reaction is finished, regulating the pH of the obtained filter cake to 8 by using 0.1mol/L sodium bicarbonate solution, and drying to obtain the rosin modified anionic macromolecular compound.
Example 2 preparation of rosin-modified anionic macromolecular compounds:
(1) adding 0.1kg of rosin into a reactor, heating to 150 ℃ until the rosin is completely melted, adding 0.05kg of maleic acid and 0.3g of aluminum trichloride, heating to 200 ℃, and reacting for 6.5 hours to obtain maleic rosin;
(2) adding 0.1kg of maleic rosin, 0.0015kg of p-toluenesulfonic acid, 0.06kg of ethylene glycol monoallyl ether and 0.4g of benzoquinone into 0.4kg of gasoline, heating to 130 ℃, reacting for 6 hours, separating out an upper solvent after the reaction is finished, standing for 30 hours, washing the separated solid with water at 75 ℃ for 5 times, and drying to obtain a maleic rosin ester;
(3) adding 0.1kg of maleic rosin ester, 0.08kg of propylene sulfonic acid and 0.007kg of azodiisobutyronitrile into 0.6kg of chloroform, stirring and dispersing uniformly, adding 1.5kg of water into the mixture, heating to 85 ℃, stirring and reacting for 18 hours, filtering after the reaction is finished, regulating the pH value of the obtained filter cake to 8 by using 0.1mol/L sodium bicarbonate solution, and drying to obtain the rosin modified anionic macromolecular compound.
Example 3 preparation of amidated styrene-maleic anhydride copolymer:
1) Adding 0.1kg of (ethane-1, 2-diylbis (oxy)) dimethylamine into 0.5kg of dichloromethane, adding 0.15kg of di-tert-butyl dicarbonate, reacting for 2 hours at 25 ℃, and distilling under reduced pressure to remove dichloromethane after the reaction is finished to obtain dimethylamine derivative with one amine group protected; 1 H NMR(400 MHz, DMSO-d 6 , 298 K) δ 9.23(t, 1H), 8.67(t, 2H), 4.65(t, 2H), 3.55(s, 2H), 3.45(t, 4H),1.35(d, 9H)。
2) Adding 0.1kg of dimethylamine derivative with protected amine terminal groups, 0.15kg of heptaethylene glycol mono-p-toluenesulfonate and 0.05kg of potassium carbonate into 0.5kg of acetonitrile, stirring and dissolving, heating and refluxing for reaction for 10 hours, filtering after the reaction is finished, distilling the obtained filtrate under reduced pressure to remove acetonitrile, adding 0.02kg of trifluoroacetic acid and 0.5kg of dichloromethane into the obtained solid, reacting for 5 hours at 25 ℃, distilling under reduced pressure to remove dichloromethane after the reaction is finished, and drying to obtain an aminoethoxy derivative; 1 H NMR(400 MHz, DMSO-d 6 , 298 K) δ 8.53(t, 2H), 5.50-5.62(m,1H), 4.86(t, 2H), 4.65(d, 2H), 3.40-3.55(t, 30H), 3.22(s, 3H), 2.65(m, 2H)。
3) Adding 0.1kg of styrene-maleic anhydride copolymer into 0.5kg of cyclohexanone, stirring and dissolving, adding 0.2kg of aminoethoxy derivative, stirring and reacting for 1h at 90 ℃, and distilling under reduced pressure to remove the solvent, thus obtaining the amidated styrene-maleic anhydride copolymer.
Example 4 preparation of amidated styrene-maleic anhydride copolymer:
1) Adding 0.1kg of (ethane-1, 2-diylbis (oxy)) dimethylamine into 0.7kg of dichloromethane, adding 0.16kg of di-tert-butyl dicarbonate, reacting for 4 hours at the temperature of 27 ℃, and distilling under reduced pressure to remove dichloromethane after the reaction is finished to obtain dimethylamine derivative with one amine group protected;
2) Adding 0.1kg of dimethylamine derivative with one amine group protected, 0.17kg of heptaethylene glycol mono-p-toluenesulfonate and 0.07kg of potassium carbonate into 0.75kg of acetonitrile, stirring and dissolving, heating and refluxing for reaction for 16 hours, filtering after the reaction is finished, distilling the obtained filtrate under reduced pressure to remove acetonitrile, adding 0.025kg of trifluoroacetic acid and 0.7kg of dichloromethane into the obtained solid, reacting for 8 hours at 25 ℃, distilling under reduced pressure to remove dichloromethane after the reaction is finished, and drying to obtain an aminoethoxy derivative;
3) Adding 0.1kg of styrene-maleic anhydride copolymer into 0.7kg of cyclohexanone, stirring and dissolving, adding 0.3kg of aminoethoxy derivative, stirring and reacting for 2 hours at 95 ℃, and distilling under reduced pressure to remove the solvent to obtain the amidated styrene-maleic anhydride copolymer.
Example 5 a treating agent was obtained by uniformly stirring and dispersing 10 parts of the rosin-modified anionic macromolecular compound obtained in example 1, 20 parts of the amidated styrene-maleic anhydride copolymer prepared in example 3 and 200 parts of water.
Pigment red 57:1, preparation:
mixing 4B-acid with water, heating to boil to remove p-toluidine, adding lime, filtering, cooling, mixing filtrate with sodium nitrite, adding into mixture of hydrochloric acid and ice, and diazotizing; dissolving 2, 3-acid in sodium carbonate water solution, slowly adding the diazonium solution at 10 ℃, stirring for reaction, and filtering; drying to obtain a pigment red 57 crude compound;
9kg of water are added to 1kg of crude pigment red 57 compound,to obtain a pigment aqueous suspension with a mass concentration of 10%, adding 0.1kg of a treating agent, stirring for 1h to uniformly disperse and adsorb the pigment crude compound, and adding 3.2kg of CaCl with a mass concentration of 20% 2 The aqueous solution is subjected to laking, stirring for 0.5h, heating to 80 ℃ after full laking, adding dilute hydrochloric acid to adjust the pH of the system to 6, continuously stirring for 0.5h, keeping the pH stable, standing for 2h after stirring is finished, vacuum-filtering, washing the obtained filter cake with water for 2 times, and vacuum-drying at 50 ℃ to obtain pigment red 57 with loose irregular structure: 1 powder aggregate.
Example 6 the treatment agent was prepared in the same manner as in example 5.
Pigment red 53:1, preparation:
adding CLT-acid into hydrochloric acid aqueous solution, stirring overnight, cooling the next day, diluting, adding sodium nitrite solution under the liquid surface for diazotization, and diluting for later use; adding 2-naphthol into a sodium hydroxide aqueous solution, dissolving, diluting, adding diazonium salt suspension below the liquid level for coupling, stirring, adding dilute acetic acid, and filtering; drying the obtained filter cake to obtain a pigment red 53 crude product compound;
adding 9kg of water into 1kg of pigment red 53 crude compound to obtain pigment water suspension with mass concentration of 10%, adding 0.12kg of treating agent, stirring for 1h to uniformly disperse and adsorb with pigment crude compound, and adding 3kg of BaCl with mass concentration of 22% 2 The aqueous solution is subjected to laking, stirring for 0.6h, heating to 85 ℃ after full laking, adding dilute hydrochloric acid to adjust the pH of the system to 6.2, continuously stirring for 0.6h, keeping the pH stable, standing for 2.5h after stirring is finished, vacuum suction-filtering, washing the obtained filter cake with water for 2 times, and vacuum-drying at 50 ℃ to obtain pigment red 53 with a loose irregular structure: 1 powder aggregate.
Example 7 a treating agent was obtained by uniformly stirring and dispersing 15 parts of the rosin-modified anionic macromolecular compound obtained in example 2, 22 parts of the amidated styrene-maleic anhydride copolymer prepared in example 4 and 240 parts of water.
Pigment red 48:3, preparation:
firstly, dissolving 2B-acid sodium salt in water, filtering and cooling, and mixing with sodium nitrite solution; then putting the mixture into hydrochloric acid aqueous solution for diazotization and dilution; dissolving 2, 3-acid in sodium carbonate aqueous solution, and cooling; adding the heavy ammonia liquor under the liquid level, coupling, stirring, heating and filtering; drying the obtained filter cake to obtain a pigment red 48 crude product compound;
adding 9kg of water into 1kg of pigment red 48 crude compound to obtain pigment water suspension with mass concentration of 10%, adding 0.13kg of treating agent, stirring for 1.5h to uniformly disperse and adsorb with pigment crude compound, and adding 1.13kg of SrCl with mass concentration of 30% 2 The aqueous solution is subjected to laking, stirring for 0.75h, heating to 88 ℃ after full laking, adding dilute hydrochloric acid to adjust the pH of the system to 6.5, continuously stirring for 0.8h, keeping the pH stable, standing for 2.8h after stirring, vacuum suction-filtering, washing the obtained filter cake with water for 2 times, and vacuum-drying at 50 ℃ to obtain pigment red 48 with loose irregular structure: 3 powder aggregate.
Example 8 the treatment agent was prepared in the same manner as in example 7.
Preparation of pigment yellow 191:
dissolving 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid in water, adding sodium hydroxide aqueous solution under heating for dissolution, adding hydrochloric acid for mixing, cooling the obtained suspension, and adding sodium nitrite solution under the liquid level for diazotization; 1- (3 '-sulfophenyl) -3-methyl-5-pyrazolone and 1- (4' -sulfophenyl) -5-pyrazolone-3-carboxylic acid are added to an aqueous sodium hydroxide solution to dissolve the same; adding diazonium salt suspension under the liquid surface for coupling, stirring, adding sodium hydroxide aqueous solution for regulating pH, and filtering; drying the obtained filter cake to obtain a crude pigment yellow 191 compound;
adding 9kg of water into 1kg of pigment yellow 191 crude compound to obtain pigment water suspension with mass concentration of 10%, adding 0.15kg of treating agent, stirring for 2h to uniformly disperse and adsorb with pigment crude compound, and adding 1.5kg of CaCl with mass concentration of 35% 2 The aqueous solution is subjected to laking, stirring for 1h, heating to 90 ℃ after full laking, adding dilute hydrochloric acid to adjust the pH of the system to 7, continuously stirring for 1h, keeping the pH stable, standing for 3h after stirring is finished, vacuum-filtering, washing the obtained filter cake with water for 3 times, and vacuum-drying at 50 ℃ to obtain the aqueous solutionTo pigment yellow 191 powdery aggregates with loose irregular structures.
Example 9 the treatment agent was prepared in the same manner as in example 7.
Preparation of pigment orange 19:
adding o-chloroaniline into a hydrochloric acid aqueous solution, cooling, adding a sodium nitrite solution under stirring for diazotization, and diluting for later use; adding 2-naphthol-6-sulfonic acid into sodium carbonate aqueous solution, dissolving, diluting, adding diazonium salt suspension below the liquid surface for coupling, and filtering; drying the obtained filter cake to obtain a pigment orange 19 crude product compound;
adding 9kg of water into 1kg of pigment orange 19 crude compound to obtain pigment water suspension with mass concentration of 10%, adding 0.1kg of treating agent, stirring for 1h to uniformly disperse and adsorb with pigment crude compound, and adding 2.4kg of BaCl with mass concentration of 20% 2 The aqueous solution is subjected to laking, stirring is carried out for 1h, heating is carried out to 90 ℃ after full laking, the pH of the system is regulated to 6.9 by adding dilute hydrochloric acid, stirring is continued for 1h, the pH is kept stable, standing is carried out for 3h after stirring is finished, vacuum suction filtration is carried out, the obtained filter cake is washed with water for 3 times, and then vacuum drying is carried out at 50 ℃ to obtain pigment orange 19 powdery aggregate with loose irregular structure.
Performing performance detection on the pigment compound prepared in the examples 5-9 and commercial pigment respectively, wherein the bulk density is detected according to the method in GB/T21877-2015, accurately weighing 50g of the pigment compound, placing into a measuring cylinder, sealing, vibrating up and down for 10 ℃, and recording the sample scale in the measuring cylinder; the dust fall was detected by visual inspection: 50g of pigment compound was weighed accurately, and the mixture was put into a beaker at a constant speed at a height of 30 cm from the mouth of the beaker, and the dust was visually observed. The tinting strength was measured according to the method in GB/T5211.19-1988; the colored light is detected according to the method in GB 1864-89; transparency was measured according to DIN 53163:1988. The test results are shown in Table 1.
As can be seen from the results in Table 1, the pigment compound prepared by the preparation method of the dust-free pigment is loose irregular granular powder, has small bulk density, is easy to disperse and high in transparency, the tinting strength is 95% -100% of that of the corresponding traditional pigment, the effective content of the pigment is 85% -90%, the problem of dust flying in the packaging and metering processes is avoided, and the operation environment and the human health are effectively protected.
While the foregoing describes the embodiments of the present invention, it is not intended to limit the scope of the present invention, and various modifications or variations may be made by those skilled in the art without the need for inventive effort on the basis of the technical solutions of the present invention.
Claims (6)
1. A preparation method of a dust-free pigment is characterized in that: the method comprises the following steps: adding water into an azo lake series organic pigment crude product compound obtained after the coupling reaction to obtain a pigment water suspension with the mass concentration of 10%, adding a treating agent into the pigment water suspension, stirring for 1-2 hours to uniformly disperse the pigment water suspension and adsorb the pigment water suspension with the pigment crude product compound, adding an inorganic salt water solution to carry out laking, stirring for 0.5-1 hour, heating to 80-90 ℃ after full laking, adding a dilute hydrochloric acid to adjust the pH of a system to 6-7, continuously stirring for 0.5-1 hour, keeping the pH stable, standing for 2-3 hours after stirring is finished, carrying out vacuum suction filtration, washing an obtained filter cake with water for 2-3 times, and carrying out vacuum drying at 50 ℃ to obtain dust-free pigment powder;
the treating agent is an emulsion prepared by uniformly stirring and dispersing 10-20 parts of rosin modified anionic macromolecular compound, 20-25 parts of amidated styrene-maleic anhydride copolymer and 200-300 parts of water in parts by weight;
the structural formula of the rosin modified anionic macromolecular compound is as follows:
；
the amidated styrene-maleic anhydride copolymer has the structural formula:
；
the rosin modified anionic macromolecular compound is prepared by the following method:
(1) adding rosin into a reactor, heating to 140-150 ℃ until the rosin is completely melted, adding maleic acid and aluminum trichloride, heating to 200 ℃, and reacting for 5-8 hours to obtain maleic rosin;
the mass ratio of the rosin to the maleic acid to the aluminum trichloride is 1:0.4 to 0.6:0.002 to 0.004;
(2) adding the maleated rosin, the p-toluenesulfonic acid, the ethylene glycol monoallyl ether and the benzoquinone obtained in the step (1) into gasoline, heating to 120-150 ℃, reacting for 5-8 hours, separating out an upper solvent after the reaction is finished, standing for 24-36 hours, washing the separated solid with water at 70-80 ℃ for 3-5 times, and drying to obtain maleated rosin ester;
the mass ratio of the maleated rosin to the p-toluenesulfonic acid to the ethylene glycol monoallyl ether to the benzoquinone to the gasoline is 1:0.01 to 0.02:0.5 to 0.75:0.003 to 0.005: 3-5;
(3) adding the maleated rosin ester, the acrylic sulfonic acid and the azodiisobutyronitrile prepared in the step (2) into chloroform, stirring and dispersing uniformly, adding water into the mixture, heating the mixture to 70-90 ℃, stirring and reacting for 15-24 hours, performing suction filtration after the reaction is finished, regulating the pH of the obtained filter cake to 8 by using 0.1mol/L sodium bicarbonate solution, and drying to obtain a rosin modified anionic macromolecular compound;
the mass ratio of the maleated rosin ester, the acrylic sulfonic acid, the azodiisobutyronitrile, the chloroform and the water is 1: 0.5-1: 0.05-0.1: 5-10: 10-20 parts of a base;
the amidated styrene-maleic anhydride copolymer is prepared according to the following method:
1) Adding 1 part of (ethane-1, 2-diylbis (oxy)) dimethylamine into 5-10 parts of dichloromethane, adding 1.5-1.8 parts of di-tert-butyl dicarbonate, reacting for 2-6 hours at 25-30 ℃, and distilling under reduced pressure to remove dichloromethane after the reaction is finished to obtain dimethylamine derivatives with one end of amine groups protected;
the mass ratio of the (ethane-1, 2-diylbis (oxy)) dimethylamine to the methylene dichloride to the di-tert-butyl dicarbonate is 1: 5-10: 1.5-1.8;
2) Adding the dimethylamine derivative with one amine group protected in the step 1), heptaethylene glycol mono-p-toluenesulfonate and potassium carbonate into acetonitrile, stirring and dissolving, heating and refluxing for reaction for 10-20 h, filtering after the reaction is finished, distilling the obtained filtrate under reduced pressure to remove acetonitrile, adding trifluoroacetic acid and dichloromethane into the obtained solid, reacting for 5-10 h at 25-30 ℃, distilling under reduced pressure to remove dichloromethane after the reaction is finished, and drying to obtain an aminoethoxy derivative;
the mass ratio of the dimethylamine derivative with one amine group protected, the heptaethylene glycol mono-p-toluenesulfonate, the potassium carbonate, the acetonitrile, the trifluoroacetic acid and the dichloromethane is 1: 1.5-2: 0.5 to 0.8: 5-10: 0.2-0.3: 5-10;
3) Adding the styrene-maleic anhydride copolymer into cyclohexanone, stirring and dissolving, then adding the aminoethoxy derivative obtained in the step 2), stirring and reacting for 1-2 hours at 90-100 ℃, and distilling under reduced pressure to remove the solvent to obtain an amidated styrene-maleic anhydride copolymer;
the mass ratio of the styrene-maleic anhydride copolymer, the cyclohexanone and the aminoethoxy derivative is 1: 5-10: 2-4.
2. The method for producing a dust-free pigment according to claim 1, wherein: the inorganic salt is CaCl 2 、BaCl 2 、SrCl 2 、MgCl 2 Or MnCl 2 。
3. The method for producing a dust-free pigment according to claim 1, wherein: the mass concentration of the inorganic salt aqueous solution is 20-35%.
4. The method for producing a dust-free pigment according to claim 1, wherein: the water content of the obtained dust-free pigment powder is less than 3%.
5. The method for producing a dust-free pigment according to claim 1, wherein: the mass ratio of the organic pigment crude product compound to the treating agent to the inorganic salt aqueous solution is 100: 10-15: 100-320.
6. The method for producing a dust-free pigment according to claim 1, wherein: the azo lake series organic pigment is pigment yellow 62, pigment yellow 104, pigment yellow 133, pigment yellow 169, pigment yellow 168, c.i. pigment yellow 100, pigment yellow 183, pigment yellow 190, pigment yellow 191, c.i. pigment red 48 series, c.i. pigment red 52 series, c.i. pigment red 57 series, c.i. pigment orange 17 series, pigment orange 18 series, pigment orange 19 series, pigment orange 46 series, pigment red 49 series, pigment red 50 series, or pigment red 53 series.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1518094A (en) * | 1975-10-09 | 1978-07-19 | Ciba Geigy Ag | Pigment preparations |
| US5681876A (en) * | 1995-06-27 | 1997-10-28 | Hoechst Aktiengesellschaft | Pulverulent pigment preparation |
| US6261358B1 (en) * | 1998-10-15 | 2001-07-17 | Bayer Aktiengesellschaft | Pigment preparations |
| CN112724706A (en) * | 2021-01-27 | 2021-04-30 | 宇虹颜料股份有限公司 | Preparation method of organic pigment easy to disperse in plastic |
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| DE10122616A1 (en) * | 2001-05-10 | 2002-11-14 | Clariant Gmbh | Process for the production of pigment granules |
| JP2006509067A (en) * | 2002-12-04 | 2006-03-16 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Dust-free pigment composition obtained by spray drying |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1518094A (en) * | 1975-10-09 | 1978-07-19 | Ciba Geigy Ag | Pigment preparations |
| US5681876A (en) * | 1995-06-27 | 1997-10-28 | Hoechst Aktiengesellschaft | Pulverulent pigment preparation |
| US6261358B1 (en) * | 1998-10-15 | 2001-07-17 | Bayer Aktiengesellschaft | Pigment preparations |
| CN112724706A (en) * | 2021-01-27 | 2021-04-30 | 宇虹颜料股份有限公司 | Preparation method of organic pigment easy to disperse in plastic |
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Denomination of invention: A method for preparing dust-free pigments Granted publication date: 20231110 Pledgee: Shandong Penglai Rural Commercial Bank Co.,Ltd. Pledgor: PENGLAI XINGUANG PIGMENT CHEMICAL Co.,Ltd. Registration number: Y2024980009573 |