CN109627490B - Red organic colorant applied to resin coloring and preparation method thereof - Google Patents
Red organic colorant applied to resin coloring and preparation method thereof Download PDFInfo
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- CN109627490B CN109627490B CN201811484140.5A CN201811484140A CN109627490B CN 109627490 B CN109627490 B CN 109627490B CN 201811484140 A CN201811484140 A CN 201811484140A CN 109627490 B CN109627490 B CN 109627490B
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- methyl
- anthrapyridone
- colorant
- general formula
- resin
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- 239000003086 colorant Substances 0.000 title claims abstract description 61
- 239000011347 resin Substances 0.000 title claims abstract description 43
- 229920005989 resin Polymers 0.000 title claims abstract description 43
- 238000004040 coloring Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 15
- OSAIMLBEKSZSPK-UHFFFAOYSA-N 6-amino-4-methylnaphtho[2,3-f]quinolin-1-one Chemical compound NC1=CC2=C(C(C=CN2C)=O)C2=CC3=CC=CC=C3C=C12 OSAIMLBEKSZSPK-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000010751 Ullmann type reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 6
- 150000004996 alkyl benzenes Chemical group 0.000 claims description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229910000365 copper sulfate Inorganic materials 0.000 claims 1
- 238000013508 migration Methods 0.000 abstract description 17
- 230000005012 migration Effects 0.000 abstract description 17
- 239000002904 solvent Substances 0.000 abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000001062 red colorant Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical group C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000001746 injection moulding Methods 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 239000012860 organic pigment Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000992 solvent dye Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- ATIJMJKGJMIWSW-UHFFFAOYSA-N 6-bromo-4-methylnaphtho[2,3-f]quinolin-1-one Chemical compound Cn1ccc(=O)c2c1cc(Br)c1cc3ccccc3cc21 ATIJMJKGJMIWSW-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004595 color masterbatch Substances 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000012994 photoredox catalyst Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- JZGUXCXDBKBCDN-UHFFFAOYSA-N 21295-57-8 Chemical compound C12=C3C(=O)C4=CC=CC=C4C1=CC(=O)N(C)C2=CC=C3NC1CCCCC1 JZGUXCXDBKBCDN-UHFFFAOYSA-N 0.000 description 1
- XCCNRBCNYGWTQX-UHFFFAOYSA-N 3-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(N)=C1 XCCNRBCNYGWTQX-UHFFFAOYSA-N 0.000 description 1
- POLIXZIAIMAECK-UHFFFAOYSA-N 4-[2-(2,6-dioxomorpholin-4-yl)ethyl]morpholine-2,6-dione Chemical group C1C(=O)OC(=O)CN1CCN1CC(=O)OC(=O)C1 POLIXZIAIMAECK-UHFFFAOYSA-N 0.000 description 1
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- VJUKWPOWHJITTP-UHFFFAOYSA-N 81-39-0 Chemical compound C1=CC(C)=CC=C1NC1=CC=C2C3=C1C(=O)C1=CC=CC=C1C3=CC(=O)N2C VJUKWPOWHJITTP-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical group CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 238000007592 spray painting technique Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention relates to a red organic colorant applied to resin coloring and a preparation method thereof, and the red organic colorant has a structural general formula shown as I:
Description
Technical Field
The invention belongs to the field of organic coloring agents, and particularly relates to a high-temperature-resistance, migration-resistance and easy-dispersion red organic coloring agent applied to resin coloring and a preparation method thereof.
Background
The development of material science has higher and higher requirements on the performance of the colorant, and has higher requirements on the temperature resistance, the migration resistance in resin and the dispersibility of the colorant besides excellent weather resistance, light resistance and various chemical resistances. One part of the organic colorant is various dyes and solvent dyes with certain water solubility or solvent solubility, and the other part is pigment which is insoluble in water and various application media. The resin coloring can be only solvent dyes and pigments, and water-soluble dyes cannot be used. Although such colorants are commercially available, they all have certain drawbacks for use in coloring resins. Such as: solvent dyes have good tinctorial properties and are dissolved and dispersed in resins, but color bleeding occurs during the coloring process or during the leaving of the colored object, i.e., poor migration resistance. The organic pigment has bright color and good performance, does not migrate, but is difficult to disperse into an application medium in application due to compact crystal structure and easy aggregation, and particularly has the problem of blockage in high-precision coloring, such as in the field of fiber stock solution coloring, the field of digital spray painting and the like, and the color reducibility is poor, so that the coloring effect of the dye is difficult to achieve.
There are many colorants containing anthrapyridone structure disclosed in the prior art, wherein there are 4 colorants related to solvent dye, which are c.i. solvent red 52, c.i. solvent red 149, c.i. solvent red 150, and c.i. solvent red 151, respectively;
the structural colorant has bright color, high tinting strength and good temperature resistance (280 ℃), and can be colored by thermoplastic resin. However, since the molecular weight is small, the solubility in a solvent is high, and the resin cannot be applied to high-quality products, particularly PET and PA resins with high processing temperature, color migration occurs, namely, the migration resistance is poor.
In recent years, there have been many reports of research on the development of colorants around the anthrapyridone structure, such as: the publication of 2003 in the journal of "dyes and dyeings" by yiyi et al, yosu, aolunda scientific and technical practice, inc, uses halogenated anthrapyridone as a main raw material, and condenses with ammonia, monomethylamine, monoethylamine, n-propylamine, n-butylamine, ethanolamine, p-toluidine, 3, 4-dimethylaniline, p-methoxyaniline, o-isopropylaniline, m-isopropylaniline, p-isopropylaniline, n-butylaniline, p-tert-butylaniline, cyclohexylamine, and sixteen amines of benzylamines to obtain the corresponding dyes, and the solubility of the synthesized dyes was measured, leading to the conclusion: the solubility of the synthesized sixteen compounds in the organic solvent is increased along with the reduction of the polarity of the solvent; the solubility gradually increases with increasing carbon chain.
Chinese patent CN 101535269a discloses a thermostable colorant related to anthrapyridone compounds, which can be used for coloring polycarbonate articles and has excellent heat resistance, light resistance and color bleeding resistance. Two novel structural anthrapyridone compounds are disclosed as follows.
Four novel anthrapyridone magenta dyes are synthesized by the university of great colligation Master academic thesis, Lishiyu and the like, and the dyes have good light-resistant stability. The four-branch dye is a water-soluble dye and has the following structure:
the research surrounding the increase of molecular structure mainly comes from the reports in japan.
Japanese patent JP 2003-192930A in 2003 discloses a magenta dye with an anthrapyridone structure, wherein R is selected from a hydrogen atom, an alkyl group or a cyclohexyl group, Y is selected from a hydrogen atom, a hydroxyl group, an amino group, a mono-or dialkylamino group, an alkoxy group, a phenylamino group, a phenoxy group, an aralkyl or cycloalkylamino group, a naphthylamino group and the like, and X is selected from ethylenediamine, butanediamine, hexamethylenediamine and the like, and the compound has excellent fastness in light resistance, water resistance and the like.
JP 2012-126770A published in 2012 by Japanese chemists discloses a novel anthrapyridone compound, the structure of which is as follows, the group X is ethylenediamine tetraacetic dianhydride, and the compound has high-definition color tone and is excellent in light resistance and weather fastness.
However, the research still adopts water-soluble dyes, and the main application field is digital painting. And the bridge group of the symmetrical part is a flexible chain segment and does not have a rigid structure, so that a certain degree of crystallinity cannot be formed, and the problem of resin coloring is difficult to solve.
Disclosure of Invention
The invention aims to provide a red organic colorant with novel structure and applied to resin coloring and a preparation method thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a red organic colorant for coloring resin is disclosed, which is a compound represented by general formula I,
general formula I
In the formula:
r is selected from hydrogen and C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a).
Preferably, R in the general formula I is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, chlorine or bromine.
More preferably, R in the general formula I is selected from hydrogen, methyl or chlorine.
A preparation method of a red organic colorant applied to resin coloring,
the method comprises the following steps: reaction formula is
Wherein: x is selected from Cl and Br;
r is selected from-H, C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a);
6-X-N-methyl-anthrapyridone (6-X-3-methyl-3H-naphtho [1,2,3-de ] quinoline-2,7-dione) and 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine are mixed, and the mixture is subjected to Ullmann condensation reaction in a high boiling point organic solvent in the presence of a catalyst and an acid-binding agent to obtain the compound shown in the general formula I.
Further, the 6-X-N-methyl-anthrapyridone and the 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine are mixed and subjected to Ullmann condensation reaction for 10-12h at 160-180 ℃ in a high-boiling-point organic solvent in the presence of a catalyst and an acid-binding agent to obtain a compound shown in the general formula I; wherein the mol ratio of the 6-X-N-methyl-anthrapyridone to the 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine is 2:1, the weight ratio of the high-boiling-point organic solvent to 6-X-N-methyl-anthrapyridone is 10-13: 1, the molar ratio of the acid-binding agent to 6-X-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to 6-X-N-methyl-anthrapyridone is 1: 14-16.
The second method has the reaction formula
The compound of the general formula I is obtained by carrying out Ullmann condensation reaction on 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine in a high boiling point organic solvent in the presence of an acid binding agent and a catalyst.
Further, 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine are subjected to Ullmann condensation reaction for 10 to 12 hours at the temperature of 160-170 ℃ in a high-boiling-point organic solvent in the presence of an acid binding agent and a catalyst to obtain a compound shown in the general formula I; wherein the mol ratio of the 6-amino-N-methyl-anthrapyridone to the 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine is 2:1, and the weight ratio of the high boiling point organic solvent to the 6-amino-N-methyl-anthrapyridone is 11-13: 1, the molar ratio of the acid-binding agent to the 6-amino-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to the 6-amino-N-methyl-anthrapyridone is 1: 14-16.
The starting materials in the synthesis method of the second method can be obtained by synthesis in the prior literature, such as the literatures SU 1016283 and s.von anger.product subglasses 3: 1,3, 5-triazines and phosphor alloys [ J ]. Science of Synthesis,2004,1(7):449-583. mention the Synthesis of the starting materials.
In the two synthesis methods, the catalyst is selected from copper powder, cuprous chloride, cuprous iodide, cupric acetate or cupric sulfate, preferably cuprous chloride or cuprous iodide; the acid-binding agent is alkali metal carbonate or alkali metal bicarbonate; alkali metal bicarbonates are preferred.
In the above process-the high-boiling organic solvent is usually dichlorobenzene, nitrobenzene, dimethyl sulfoxide, N-methylpyrrolidone or alkylbenzene.
In the second method, the inert organic solvent is dichlorobenzene, nitrobenzene, dimethyl sulfoxide or alkylbenzene.
In the two synthesis methods, after Ullmann condensation reaction, the product is subjected to heat treatment by a polar organic solvent and particle size adjustment to obtain the red powdery compound with the general formula I and a soft structure, so that the red powdery compound is convenient for subsequent application and dispersion, and the cost for recovering the solvent can be reduced.
The polar organic solvent is alcohols, N-dimethylformamide, dimethyl sulfoxide and the like; alcohol organic solvents are preferred. Wherein the alcohol can be methanol, ethanol, n-butanol, isobutanol, amyl alcohol, tertiary amyl alcohol, octanol, etc. Butanol is more preferable.
The two synthetic methods described above are preferred from the viewpoint of ease of preparation and availability of raw materials.
The application of the compound in the general formula I as a coloring agent for resin is disclosed.
The resin may be PE, PP, PET, PC, PA ABS resin, PS resin, PMMA, or the like. Can be used for preparing color master batches, coloring fiber stock solution, plastic films, plastic printing or injection molding and other fields. The beneficial effects of the invention are highlighted as follows:
1. the invention is suitable for resin coloring organic colorants which are bright yellow red, have a melting point of 320 ℃, show obvious crystallinity by XRD analysis and show fine rod-like crystals by electron microscopy. The coloring agent has soft particles, and has obvious easy dispersibility compared with the traditional organic pigment by adopting a scraper fineness instrument to detect the easy dispersibility of the coloring agent.
2. The colorant is subjected to temperature resistance test, a PET resin injection molding method is adopted, the injection molding condition is an organic pigment limit detection condition in the field, namely, the retention time is 5 minutes at 300 ℃, C.I. pigment yellow 147 with good temperature resistance recognized in the field of fiber stock solution coloring is taken as a reference standard, the colorant has remarkable advantages in color change and color difference value, and has better temperature resistance than the C.I. pigment yellow 147.
3. The resistance test is carried out by adopting a national standard method, the rating standard is optimally 5 grades, the worst is 1 grade, the colorant related to the invention shows 5 grades of resistance in different polar organic solvents, and the acid and alkali resistance of the colorant is 5 grades, so that the colorant shows excellent solvent resistance and chemical resistance.
In conclusion, the compound of the general formula I is an organic colorant, has a novel structure, is bright yellow red, has good heat resistance, solvent resistance and easy dispersibility, can meet the requirements of temperature resistance and migration resistance in coloring of high-temperature processed resin such as PET and the like, and has loose and soft particles and good easy dispersibility. The product can be used as a colorant for resin, can be used in the fields of color master batches, fiber stock solution coloring, plastic films, plastic printing or injection molding and the like, meets the application requirements of PE, PP, PET, PC, PA ABS resin, PS resin, PMMA and the like, and has potential commercial value.
Drawings
FIG. 1 is a transmission microtopography under an optical microscope of a colorant provided in example 1 of the present invention.
FIG. 2 is a scanning microtopography of a colorant provided in example 1 of the present invention under an electron microscope.
FIG. 3 is an XRD analysis of a colorant according to the present invention.
Detailed Description
The following examples serve to illustrate the invention in further detail. In the examples, parts and percentages are by weight unless otherwise indicated.
The poor migration of colorants known to those skilled in the art is generally due to the colorant's solubility in the application medium, and supersaturation precipitation occurs as application conditions change; or the colorant has poor temperature resistance, and is decomposed and sublimated in high-temperature application to cause color overflow. Temperature resistance and solvent resistance are therefore important conditions for evaluating the migration resistance of coloring. Dispersibility is due to the molecular polarity, planarity and symmetry of the compound which affects the growth and aggregation of its nascent structure, and thus affects the size and hardness of the colorant's crystal form and aggregates. The invention provides a compound with a novel structure, which connects an anthrapyridone structure with moderate molecular polarity and good temperature resistance into a compound with larger molecular weight by taking a triazine structure compound as a bridging group. The compound keeps the excellent temperature resistance characteristic of an anthrapyridone structure, and the solvent resistance characteristic is ensured due to the increase of the molecular weight, so that the migration resistance of the compound is ensured; meanwhile, the rigidity of the large molecular structure is enhanced but the structural connection of the bridge group triazine does not have planarity, and although the whole molecular structure has symmetry and rigidity, the growth of crystals and the growth and aggregation of nascent particles are still influenced due to poor planarity, so that the compound particles are soft and easy to disperse in an application medium, and have better dispersibility.
The anthrapyridone compound shown in the general formula I is characterized by bright yellow red color and excellent heat resistance, and the injection molding test of staying at 300 ℃ of PET resin for 5min, the bleeding test of solvents such as ethanol, ethyl acetate, N-dimethylformamide, dimethyl sulfoxide and the like, and the acid and alkali treatment test prove that the compound shown in the general formula I can be used for coloring the resin under the high-temperature condition, and the color can not be shifted due to the high-temperature injection molding condition and the polarity of the resin, a plasticizer and the like. Meanwhile, the compound of the general formula I has soft particles, is easy to disperse, is a colorant with potential commercial value, can be used for coloring PE PP PET, PA ABS and other resins, and can also be used for coloring stock solution of polyester, polypropylene, acrylic fiber, spandex and other fibers.
Preparation examples
Example 1
The reaction formula is as follows:
wherein: x is selected from Br; r is selected from-H.
In a 250mL four-necked flask, 7.1 parts of 6-bromo-N-methyl-anthrapyridone, 1.87 parts of benzoguanamine, 0.42 part of cuprous iodide, and 90 mL of alkylbenzene were charged. Heating to 170 ℃, keeping the temperature for reaction for 30 minutes, then gradually adding 2.1 parts of sodium bicarbonate in portions, adjusting the pH value of the reaction, and reacting for 12 hours at the temperature of 165-170 ℃. The liquid chromatogram is used for tracking the complete disappearance of the reactants, and the temperature is reduced to 90-95 ℃. Filtering and recovering the alkylbenzene mother liquor. Washing the filter cake with a small amount of ethanol until the filtrate is colorless, and recovering the washing liquid. The filter cake was washed with water until the pH was neutral and transferred to the next step for treatment.
Adding 100 ml of butanol solution into the filter cake, fully stirring for 2 hours, then heating to reflux, keeping the reflux for 3 hours, cooling to 50 ℃, performing heat filtration, and recovering mother liquor. Washed with a small amount of water and dried to obtain about 6.1 g of dry powder. Appearance: bright red powder, yield 86.5%.
Example 2
Except that cuprous chloride was used as a catalyst in place of cuprous iodide in the above preparation process, the procedure of example 1 was repeated to obtain about 5.9 g of a dry powder, as in example 1. Appearance: bright red powder, yield 83.7%.
Example 3
The difference from example 1 is that o-dichlorobenzene is used as a solvent instead of alkylbenzene, 6.8 parts of 6-bromo-N-methyl-anthrapyridone, 1.87 parts of benzoguanamine and 0.42 part of cuprous iodide as a catalyst are added into a 250mL four-neck flask, 80 mL of o-dichlorobenzene solution is added, the temperature is raised to 170 ℃, the reaction is kept at a constant temperature, 2.1 parts of sodium bicarbonate as an acid binding agent are added in portions during the reaction, the pH value of the reaction is adjusted, the reaction is carried out for 12 hours, and the liquid chromatography shows that the consumption of raw materials in the system is finished and the reaction is finished. Cooling to 90-95 deg.C, filtering, washing with o-dichlorobenzene until the filtrate is colorless, washing with alcohol and water to neutrality to obtain wet filter cake, and recovering the filtrate.
And adding 100 ml of butanol solution into the filter cake, fully stirring for 2 hours, heating to reflux, keeping the temperature and refluxing for 3 hours, cooling, filtering, washing with water and drying. About 6.12 grams of dry powder was obtained. Appearance: the red yield was 86.8%.
The dry powder samples obtained in the above examples are respectively observed under a 400-fold optical microscope in a transmission manner, and the samples are fine rod-shaped crystals, fine particles, uniform in size distribution, and free of obvious large aggregates (see fig. 1), so that the coloring agent has good color performance and easy dispersibility when being applied to resin for coloring. Meanwhile, the sample is observed to have obvious rod-like crystal morphology through scanning of an electron microscope (see figure 2).
The sample obtained above was then subjected to further XRD analysis (see fig. 3), and the prepared dry powder sample compound had distinct crystallinity and crystallinity, with organic pigment characteristics.
Therefore, the obtained colorant has a complete and regular crystal morphology and has the characteristics of an organic pigment. The compound has relatively perfect crystal structure and crystallinity, so that the compound has good temperature resistance, solvent resistance and chemical resistance, and shows good color effect.
Example 4
2, 4-diamino-6-benzene-1, 3, 5-triazine was replaced with 2.01 parts of 2, 4-diamino-6-methylbenzene-1, 3, 5-triazine by the same preparation method as in example 1 above to give about 5.96 g of a dry powder. Appearance: dark red, yield 82.9%.
Example 5
2, 4-diamino-6-benzene-1, 3, 5-triazine was replaced with 2.21 parts of 2, 4-diamino-6-chlorobenzene-1, 3, 5-triazine by the same procedure as in example 1 to give about 6.15 g of a dry powder. Appearance: dark red powder, yield 83.2%.
Meanwhile, other compounds for obtaining the R ═ alkyl, alkoxy or halogen provided by the present invention can be prepared by replacing the raw materials according to the above-mentioned preparation method, and the above-mentioned advantageous characteristics are also obtained in addition to the shift of the color phase.
Application examples
The following examples illustrate in detail the application properties and the application effects of the colorants according to the invention, taking the sample obtained in example 1 above as an example, while other compounds defined according to the invention also have corresponding effect characteristics.
Example 6: color characterization test
The sample obtained in example 1 was uniformly mixed with polyester PET powder in an amount of 1 wt%, injection-molded at 280 ℃ to prepare a PET injection-molded sheet, and color measurement was carried out using an electronic colorimeter under a D65 light source with a Lab system, wherein the color characteristics of the sample are as shown in Table 1:
table 1: color value of PET injection molded sheet of sample
Table 1 shows that the compound of the present invention is brilliant yellow red, has excellent vividness, and can be used as a coloring agent.
Example 7: easy dispersibility test
The colorant dry powder of example 1 without pre-dispersion and pulverization was taken and homogenized with No. 6 varnish on a flat mill. Grinding is carried out under the condition of not adding weights, and the change of the grinding fineness of the colorant is tracked and detected by a scraper fineness meter.
Table 2: easy dispersibility of samples
Generally, organic pigments with perfect crystallization are easy to aggregate into particles during drying to form hard particles, are difficult to disperse into application media, and have to be subjected to pre-dispersion treatment and efficient pulverization treatment, and are applied after being sieved through a certain number of sieves, such as 100 meshes, 300 meshes and the like. When the pressure is detected by using a plain grinding machine, a certain pressure is used, and the pressure of the plain grinding machine with a weight is 47 kilograms. The samples used in the application example are directly detected by a flat grinder without any pre-dispersion treatment and crushing treatment. And the weight of the flat grinding instrument is removed during detection. The test results in Table 2 show that the colorant of the present invention can be completely dispersed under a small grinding condition without pre-dispersion and pulverization treatment, and the colorant of the present invention has a good easy dispersibility.
Example 8: solvent resistance detection
The sample of example 1 of the present invention was tested for fastness properties according to water resistance, solvent resistance, acid and alkali resistance of GB/T5211.5-2008 "pigment resistance test method". The results are shown in Table 3:
TABLE 3: partial fastness Properties of samples
The compound meets the requirements of solvent resistance and chemical resistance of a high-performance colorant, and can avoid the mobility problem caused by solubility in resin application.
Example 9: heat resistance test
The colorant obtained in example 1 was mixed with a PET resin in an amount of 1 wt% to obtain a mixture, which was subjected to injection molding at 300 ℃. The retention time is 15 seconds and 5 minutes respectively, and an injection molding sheet is prepared for color difference detection. And simultaneously, performing injection molding under the same conditions by using C.I. pigment yellow 147 which is recognized in the field and can meet the coloring temperature resistance requirement of the PET fiber stock solution, and contrasting the discoloration condition. The heat resistance of the sample of example 1 in the PET resin was judged by DE comparison using an electronic colorimeter under a Lab system under a D65 light source. The results are shown in Table 4
Table 4: heat resistance in sample PET resin
The test result shows that the colorant provided by the invention has good temperature resistance, and has better temperature resistance compared with the high-temperature-resistance C.I. pigment yellow 147 commonly used in the industry. Can meet the high-temperature processing coloring requirement of resins such as PET and the like, and simultaneously avoids color migration caused by poor temperature resistance.
Example 10: migration resistance test
The method for measuring the migration resistance comprises the following steps: the sample obtained in example 1 was uniformly mixed with a polyester PET powder in an amount of 2 wt%, injection-molded at 275 ℃ to prepare a PET injection-molded sheet, a (3.2X 2.0) cm colored PET sheet was placed on a white PET knitted fabric, the sheet was placed in a thermal cycle oven having an internal temperature of 180 ℃ for 3 minutes under a pressure of 7MPa, and then the colored PET sheet was removed to observe the degree of staining on the white PET knitted fabric (the degree of DE value was measured by an electronic colorimeter using a Lab system under a D65 light source), and the sheet was evaluated according to ISO 105-A03. Grade 5 indicates no migration, grade 1 indicates severe migration, and the results of the migration resistance test are shown in table 5:
table 5: sample migration resistance test
The test result shows that the colorant has good migration resistance, and is judged to be 4-5 grade according to ISO105-A03 detection standard.
Claims (10)
1. A red organic colorant for use in resin coloration, characterized by: the colorant is a compound shown in a general formula I,
in the formula:
r is selected from hydrogen and C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a).
2. A red organic colorant for resin coloration according to claim 1, wherein: in the general formula I, R is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, chlorine or bromine.
3. A red organic colorant for resin coloration according to claim 2, wherein: in the general formula I, R is selected from hydrogen, methyl or chlorine.
4. A method for preparing the red organic colorant for coloring resin according to claim 1, wherein:
wherein: x is selected from Cl and Br;
r is selected from-H, C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a);
the compound of the general formula I is obtained by mixing 6-X-N-methyl-anthrapyridone and 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine and subjecting the mixture to Ullmann condensation reaction in a high boiling point organic solvent in the presence of a catalyst and an acid-binding agent.
5. The process for preparing a red organic colorant for coloring resins according to claim 4, wherein: mixing the 6-X-N-methyl-anthrapyridone with 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine, and carrying out Ullmann condensation reaction for 10-12h at 160-180 ℃ in a high-boiling-point organic solvent in the presence of a catalyst and an acid-binding agent to obtain a compound shown in a general formula I; wherein the mol ratio of the 6-X-N-methyl-anthrapyridone to the 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine is 2:1, the weight ratio of the high-boiling-point organic solvent to 6-X-N-methyl-anthrapyridone is 10-13: 1, the molar ratio of the acid-binding agent to 6-X-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to 6-X-N-methyl-anthrapyridone is 1: 14-16.
6. A method for preparing the red organic colorant for coloring resin according to claim 1, wherein: reaction formula is
The compound of the general formula I is obtained by carrying out Ullmann condensation reaction on 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine in a high boiling point organic solvent in the presence of an acid binding agent and a catalyst.
7. The process for preparing a red organic colorant for resin coloration according to claim 6, wherein: carrying out Ullmann condensation reaction on 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine in a high-boiling-point organic solvent at the temperature of 160-170 ℃ in the presence of an acid binding agent and a catalyst for 10-12h to obtain a compound shown in a general formula I; wherein the mol ratio of the 6-amino-N-methyl-anthrapyridone to the 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine is 2:1, and the weight ratio of the high boiling point organic solvent to the 6-amino-N-methyl-anthrapyridone is 11-13: 1, the molar ratio of the acid-binding agent to the 6-amino-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to the 6-amino-N-methyl-anthrapyridone is 1: 14-16.
8. The process for preparing a red organic colorant for resin coloration according to claim 4, 5, 6 or 7, wherein: the catalyst is selected from copper powder, cuprous chloride, cuprous iodide, copper acetate or copper sulfate; the acid-binding agent is alkali metal carbonate or alkali metal bicarbonate; the high boiling point organic solvent is alkylbenzene, dichlorobenzene, nitrobenzene, dimethyl sulfoxide or N-methyl pyrrolidone.
9. The process for preparing a red organic colorant for resin coloration according to claim 4, 5, 6 or 7, wherein: after Ullmann condensation reaction, the product is subjected to heat treatment by a polar organic solvent to obtain the red powdery compound with the general formula I and the soft structure.
10. Use of a red organic colorant according to claim 1, wherein: the compound of the general formula I is applied to being used as a coloring agent for resin.
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| 蒽吡啶酮类溶剂染料的合成和溶解性能的研究;尹益;《染料与染色》;20030831;正文第191-193页 * |
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