CN114989635B - Black pigment dispersion for polyester in-situ polymerization and preparation method thereof - Google Patents
Black pigment dispersion for polyester in-situ polymerization and preparation method thereof Download PDFInfo
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- CN114989635B CN114989635B CN202210572071.3A CN202210572071A CN114989635B CN 114989635 B CN114989635 B CN 114989635B CN 202210572071 A CN202210572071 A CN 202210572071A CN 114989635 B CN114989635 B CN 114989635B
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- Prior art keywords
- pigment
- black
- polyester
- dispersion
- black pigment
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- 239000000049 pigment Substances 0.000 title claims abstract description 167
- 239000006185 dispersion Substances 0.000 title claims abstract description 62
- 229920000728 polyester Polymers 0.000 title claims abstract description 54
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 17
- 238000011065 in-situ storage Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000002270 dispersing agent Substances 0.000 claims abstract description 46
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000006229 carbon black Substances 0.000 claims abstract description 34
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 23
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- 150000001721 carbon Chemical class 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 9
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- UOABIRUEGSGTSA-UHFFFAOYSA-N 4-bromobutyl acetate Chemical compound CC(=O)OCCCCBr UOABIRUEGSGTSA-UHFFFAOYSA-N 0.000 claims description 2
- 230000002794 monomerizing effect Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 19
- 230000032050 esterification Effects 0.000 abstract description 16
- 229920000642 polymer Polymers 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 238000006068 polycondensation reaction Methods 0.000 abstract description 8
- 238000004040 coloring Methods 0.000 abstract description 5
- 239000011550 stock solution Substances 0.000 abstract description 4
- 239000000155 melt Substances 0.000 abstract description 3
- 150000005846 sugar alcohols Polymers 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 18
- 239000002245 particle Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000011324 bead Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 238000000227 grinding Methods 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- -1 Polyethylene terephthalate Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical class N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 229920006150 hyperbranched polyester Polymers 0.000 description 2
- 125000000686 lactone group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 235000011044 succinic acid Nutrition 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HSWKIPCBJSMQFA-UHFFFAOYSA-N 1-butoxybutane;tin Chemical compound [Sn].CCCCOCCCC HSWKIPCBJSMQFA-UHFFFAOYSA-N 0.000 description 1
- DQUVVEFJBIOKQQ-UHFFFAOYSA-N 2-(4-hydroxybutyl)propanedioic acid Chemical compound OCCCCC(C(O)=O)C(O)=O DQUVVEFJBIOKQQ-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000009973 dope dyeing Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000003921 particle size analysis Methods 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005406 washing 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/04—Pigments
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
- D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention relates to a black pigment dispersion for polyester in-situ polymerization and a preparation method thereof, wherein the black pigment dispersion comprises black pigment, a pigment dispersing agent and polyalcohol, the black pigment is at least one of modified C.I. pigment black 7, C.I. pigment black 31 and C.I. pigment black 32, and the pigment dispersing agent is a polyester polymer dispersing agent. The black pigment, the polyester polymer dispersing agent and the ethylene glycol are mixed, ground and dispersed to obtain a black pigment dispersion, and the dispersion has good dispersion stability. The obtained black pigment dispersion can be used for coloring polyester stock solution, namely, the black pigment dispersion is added before polyester esterification or after esterification and polycondensation, so that the phenomenon that carbon black is seriously separated out from the walls of a reaction kettle and a melt pipe is avoided.
Description
Technical Field
The invention relates to a black pigment, in particular to a black pigment dispersion for polyester in-situ polymerization and a preparation method thereof.
Background
Polyethylene terephthalate (PET) is a semi-crystalline thermoplastic, known to have excellent mechanical, physical and chemical properties, exhibiting good chemical resistance, heat resistance and dimensional stability, and having high stiffness and strength. However, the molecular structure lacks hydrophilic groups, and the molecular chains are tightly packed, so that the dye is not easy to dye. The conventional dyeing method is to dye the manufactured textile fiber by printing and dyeing, namely: the disperse dye is used for dyeing under the conditions of high temperature and high pressure, but the method has the problems of high energy consumption, low efficiency, serious pollution and the like. The dope dyeing technology before spinning is to add coloring agent into spinning solution or melt to obtain colored polymer or melt, and to directly prepare colored fiber through spinning. The carbon reduction effect of the dope-dyed fiber before spinning is remarkable, and the dope-dyed fiber has wide market application prospect.
The most common of the polyester stock colors is black, typically furnace black. Most of the surface groups of the furnace carbon black are quinone groups, and the types and the numbers of the surface groups such as hydroxyl groups, carboxyl groups, lactone groups and the like are increased by the treatment mode of oxidation treatment, so that the dispersion stability of the carbon black in a hydrophilic system is improved.
In order to improve the blackness of polyester fibers, a phthalocyanine pigment or a phthalocyanine pigment derivative is often used as one of the additive components. The C.I. pigment black 1, also called aniline black, commercial product BASF Paliotol Black L0080, is a semitransparent blue-phase organic pigment, is transparent compared with carbon black, has blackness which cannot be achieved by the carbon black, has excellent fastness properties such as light resistance, weather resistance, solvent resistance, acid and alkali resistance and the like, but has the temperature resistance of only 200 ℃ and cannot meet the requirement of a colorant in coloring of polyester stock solution. Five perylene pigments, which remain stable at 360 ℃ and have good dispersibility, darker hues and better fastness in polyester colored fibers obtained by in situ polymerization, were prepared by reacting 3,4,9, 10-perylenetetracarboxylic dianhydride with methylamine, ethanolamine, glycine, 4-aminobutyric acid and 6-aminocaproic acid, respectively, by Veena Choudhary et al (JSDC, volume 107,September 1991,323-327). JP2003041145a discloses a black perylene pigment comprising a solid solution obtained by calcining a mixture of at least two compounds selected from the group consisting of an anhydride of perylene tetracarboxylic acid, a diimide derivative of perylene tetracarboxylic acid and a diimide derivative of perylene diiminodicarboxylic acid, having excellent blackness, excellent heat resistance and excellent weather resistance, and high tolerance and high safety, and a method for producing the same. In commercial products, c.i. pigment black 31 and c.i. pigment black 32, which are both perylene derivatives, have strong black hues, excellent light and weather fastness, excellent heat stability and chemical reagent stability, and particularly can form a liquid with fluidity at 150-200 ℃.
The pigment slurry can be uniformly dispersed into dimethyl terephthalate slurry before esterification, and the prepared melt has good uniformity and easy production control. However, because the carbon black has a longer route, the carbon black on the walls of the esterification kettle and the esterification section can be seriously separated out, so that the heat conduction is affected, the carbon black is not easy to disperse after being peeled off and enters esterification, large particles are formed, and finally, the produced slices have poor gloss and light blackness.
Disclosure of Invention
In order to overcome the defects, the invention provides a black pigment dispersion for polyester in-situ polymerization, which is obtained by mixing and grinding and dispersing modified C.I. pigment black 7 and C.I. pigment black 31 or C.I. pigment black 32 serving as black pigments and a polyester polymer dispersing agent serving as a pigment dispersing agent with ethylene glycol, and has good dispersion stability; the obtained black pigment dispersion can be used for coloring polyester stock solution, namely, the black pigment dispersion is added before polyester esterification or after esterification and polycondensation, so that the phenomenon that carbon black is seriously separated out from the walls of a reaction kettle and a melt pipe is avoided.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a black pigment dispersion for polyester in-situ polymerization comprises a black pigment, a pigment dispersing agent and a polyol, wherein the black pigment is at least one of modified C.I. pigment black 7, C.I. pigment black 31 and C.I. pigment black 32, and the pigment dispersing agent is a polyester polymer dispersing agent. Pigments of the same color may be numbered in order according to the methods commonly used in the pigment, dye-related industries, and the like, color Index (c.i.), such as phthalocyanine blue 15:1 pigment designated pigment blue 15:1, and benzimidazolone yellow designated pigment yellow 154. The specific results of the pigments such as C.I. pigment black 7 and the like provided by the invention can be retrieved from the data such as color index and the like.
Preferably, the black pigment is a mixture of modified c.i. pigment black 7 and c.i. pigment black 31.
Preferably, the black pigment is a mixture of modified c.i. pigment black 7 and c.i. pigment black 32.
Preferably, the preparation method of the modified c.i. pigment black 7 comprises the following steps: firstly, oxidizing the C.I. pigment black 7, and then, utilizing a hydroxyl-containing substance and a carboxyl-containing substance to graft-modify the oxidized C.I. pigment black 7.
Preferably, the hydroxyl-containing substance is at least one of methanol, ethanol, propylene glycol, 1, 4-butanediol, trimethylolpropane and glycerol, and the carboxyl-containing substance is at least one of formic acid, acetic acid, succinic acid and adipic acid.
Preferably, the hydroxyl-containing material is glycerol and the carboxyl-containing material is adipic acid.
Preferably, the polyol is ethylene glycol, and the pigment dispersant is formed by grafting two different esterified substances to form a polyester, and hydrolyzing and then polymerizing the polyester.
Preferably, the pigment dispersant is grafted by diethyl malonate and butyl 4-bromoacetate, then dicarboxylic acid unit alcohol monomer is obtained by hydrolysis, and the monomer is polymerized under the action of a catalyst and temperature, wherein the weight average molecular weight of the pigment dispersant is 5000-45000, and the number average molecular weight of the pigment dispersant is 1000-15000.
Preferably, the weight of the black pigment is 18-25% of the total weight of the black pigment dispersion, the weight of the pigment dispersant is 15-20% of the total weight of the black pigment, and the balance is polyol.
The invention also discloses a preparation method of the black pigment dispersoid for polyester in-situ polymerization, which comprises the steps of mixing the black pigment, the pigment dispersing agent and the polyalcohol at a high speed, grinding and filtering to obtain the black pigment dispersoid.
The beneficial effects of the invention are as follows:
1) The black color is C.I. pigment black 7 grafted and modified by hydroxyl and carboxyl after liquid phase oxidation treatment, and the dispersion stability of the modified C.I. pigment black 7 in polyester is further improved by utilizing the similarity compatibility of the modified grafting end and polyester;
2) The black pigment also comprises C.I. pigment black 31 and/or C.I. pigment black 32, and the two pigments belong to perylene derivatives, so that on one hand, the blackness of colored polyester fibers can be remarkably improved, and on the other hand, the phenomenon that carbon black on the walls of an esterification kettle and an esterification section can be seriously separated out is avoided by utilizing the characteristic of low melting point of the colored polyester fibers;
3) The pigment dispersing agent used in the invention is aliphatic hyperbranched polyester with hydrophobic groups and hydrophilic groups, and monomers forming the substance grow in three dimensions in the polymerization process to form a highly branched structure, so that pigment particles are fully segmented through steric hindrance, and aggregation of the pigment particles is avoided.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
A black pigment dispersion for polyester in-situ polymerization comprises a black pigment, a pigment dispersing agent and a polyol, wherein the black pigment is at least one of modified C.I. pigment black 7, C.I. pigment black 31 and C.I. pigment black 32, the pigment dispersing agent is a polyester polymer dispersing agent, and the polyol is ethylene glycol.
The black pigment may be a monochromatic pigment such as c.i. pigment black 7 in an inorganic pigment, c.i. pigment black 31, c.i. pigment black 32 in an organic pigment; or the black pigment is mixed by any two or three of the above. Preferably the black pigment is composed of c.i. pigment black 7 and c.i. pigment black 31 or c.i. pigment black 7 and c.i. pigment black 32.
The c.i. pigment black 7 is preferably a modified c.i. pigment black 7. Due to the influence of the production process, oxygen-containing functional groups such as carboxyl, hydroxyl, lactone groups and the like exist on the surface of the C.I. pigment black 7, and the variety and the number of the functional groups can be increased by oxidation treatment so as to improve the dispersion stability of the modified C.I. pigment black 7 in a system. The oxidation method is classified into a dry method and a wet method, i.e., a gas phase oxidation method and a liquid phase oxidation method. The gas phase oxidation method is to oxidize the c.i. pigment black 7 with some oxidizing gas, which may be atomic or molecular oxygen, ozone, dry air or humid air, etc.; the liquid phase oxidation method refers to oxidizing c.i. pigment black 7 with a solution of some liquid oxidizing agent or water-soluble oxidizing agent, such as nitric acid, hydrogen peroxide, potassium permanganate, potassium dichromate, ammonium persulfate, and the like.
Preferably, the surface treatment of the c.i. pigment black 7 by a liquid-phase oxidation method can introduce new reactive functional groups with stronger activity, and various reactions can be carried out between the c.i. pigment black 7 and more compounds through the functional groups. For example, the surface treatment of C.I. pigment black 7 by using ammonium persulfate aqueous solution, and the hydrolysis of hydrogen and persulfate on the surface of C.I. pigment black 7 to generate OH or SO 4 - Combines to form-OH or benzene ring free radical, and then combines with O in solution 2 And the oxygen content of the surface of the modified C.I. pigment black 7 is increased by combining to generate carbonyl. In addition to the above oxidizing agent, the liquid-phase oxidation method can carry out methylolation on the c.i. pigment black by formaldehyde under the action of an alkaline catalyst, so that more methylol groups are formed on the surface of the c.i. pigment black.
In order to further improve the dispersion stability of the c.i. pigment black 7 after surface oxidation in a medium, the oxidized c.i. pigment black 7 is subjected to a further treatment, wherein the treatment is to further graft-modify the oxidized c.i. pigment black 7 by selecting hydroxycarboxylic acid based on the principle of esterification reaction of hydroxyl and carboxyl. Hydroxyl-containing substances such as at least one of methanol, ethanol, propylene glycol, 1, 4-butanediol, trimethylolpropane and glycerol, preferably glycerol; the carboxylic acid-containing substance is at least one of formic acid, acetic acid, succinic acid and adipic acid, preferably adipic acid. Conventional esterification reactions are generally quite intense, such as high temperatures and/or strong acids, and this may involve side reactions such as dehydration and decarboxylation, leading to low reaction efficiency and yields. Jean-Stumbe et al have selected the solvent-free condition, utilize adipic acid and glycerin to finish the good esterification reaction process under the function of catalyst tin dibutyl oxide, through certain temperature condition and inert environment (nitrogen).
The pigment dispersant is prepared by mutually grafting two different esterified substances, and the formed polyester is polymerized after hydrolysis, and belongs to high molecular polymers. The pigment dispersing agent can be used as a polyester polymer dispersing agent, and can be obtained by grafting diethyl malonate and 4-bromobutyl acetate, hydrolyzing to obtain dicarboxylic acid unit alcohol monomer, and polymerizing the monomer under the action of a catalyst and temperature.
The pigment dispersant has a weight average molecular weight of 5000 to 45000, particularly 8000 to 38000, more particularly 10000 to 25000; the number average molecular weight is in the range of 1000 to 15000, especially 2500 to 12000, more especially 4000 to 10000.
According to the polyester in-situ synthesis method: the reaction mixture of ethylene glycol and dimethyl terephthalate (molar ratio of 2.2) in the transesterification step was heated to a final temperature of 270 ℃ under an argon atmosphere and stirred at a constant speed, and after about 3 hours the reaction was completed; in the second polycondensation step, a catalyst is added, vacuum is slowly applied, the temperature is kept stable at 270 ℃, the stirring speed is increased, and the polycondensation lasts for about 1.5 hours due to the increase of the melt viscosity until the stirrer speed is reduced to 50-60rev/min. Thus, the polyol in the present invention is preferably ethylene glycol.
The preparation method of the black pigment dispersion comprises the following steps: the black pigment, pigment dispersant, polyol mixture is prepared using, for example, high speed mixing, ball milling, sand milling, attritor milling or two or three roll milling. Preferably, the black pigment is present in the pigment dispersion in an amount of 18 to 25% by weight, the pigment dispersant is present in an amount of 15 to 20% by weight, based on the black pigment, with the remainder being the polyol.
The black pigment dispersion of the present invention can be used for coloring polyester stock solutions. Polyester stock coloring black pigment dispersions may be added prior to polyester esterification. The polyester stock may also be pigmented by adding a black pigment dispersion prior to esterification and polycondensation of the polyester. Both of these modes fall into the category of in situ polymerization.
1. Preparation of modified C.I. pigment Black 7
1. Oxidation of c.i. pigment black 7
20g of commercial C.I. pigment black 7, 175mL of formaldehyde aqueous solution (mass fraction: 33%) and 25mL of 0.1mol/L sodium hydroxide aqueous solution (as a catalyst) were sequentially added to a 500mL three-necked flask, and after heating in a water bath from room temperature to 50 ℃, the reaction was carried out under a warm condition and at a gentle stirring rate for 1.5 hours, the obtained reaction product was repeatedly washed with water and filtered, and the washed cake was dried in vacuum at 50℃for 24 hours. This product is designated "hydroxymethyl carbon black" and is designated CB-1.
2. Grafting reaction
20g of the above-mentioned methylol carbon black, 5.64g of adipic acid and 3.68g of glycerol were weighed out in this order into a three-necked flask reactor equipped with an inlet pipe for adding nitrogen and a Claisen condenser with a vacuum adapter. The mixture was heated to 150 ℃ under nitrogen atmosphere with continuous stirring until the adipic acid was completely melted and mixed uniformly, and 0.16wt.% of dibutyltin oxide (based on the total mass of adipic acid and glycerol) was added to the above reaction mixture to initiate the polycondensation reaction while the pressure was reduced to 100mbar, water produced during the reaction was distilled off, and the final product was filtered by washing with deionized water and dried to constant weight at 50 ℃. This product is denoted "graft modified carbon black", designated CB-2, i.e. modified c.i. pigment black 7.
2. Preparation of pigment dispersant
According to the method of preparation of Santimukul Santra et al (Langmuir 2010,26 (8), 5364-5373), 50g of diethyl malonate and 79.2g of butyl 4-bromoacetate are weighed into a round bottom flask containing 600ml of acetonitrile, mixed well at room temperature, added with 172.5g of potassium carbonate and refluxed for 60 hours, filtered and concentrated, extracted with ethyl acetate, washed with water, na 2 SO 4 Drying and purifying to obtain a product 1, wherein the product 1 is diethyl 2- (4-acetoxybutyl) malonate; mixing 80g of the above product 1 with 500ml of methanol in round bottom flask, adding 25wt.% NaOH aqueous solution, reacting at 90deg.C for 8 hr, adding dilute hydrochloric acid to pH 2-3, concentrating, and Na 2 SO 4 Drying and purifying to obtain a product 2, wherein the product 2 is 2- (4-hydroxy butyl) malonic acid; 58g of the product 2 and 0.43g of p-toluenesulfonic acid (catalyst) are taken and uniformly mixed in a round bottom flask, and reacted for 2 hours in an oil bath at 150 ℃ in a nitrogen environment, and the obtained polymer is purified, precipitated, centrifuged, washed and dried to obtain the pigment dispersing agent. The dispersant had a Mw of 13200, a Mn of 8800, and a polydispersity PD of 1.5.
3. Preparation of black pigment Dispersion
Example 1
36.0 parts of the above-mentioned graft-modified carbon black CB-2, 8.0 parts of C.I. pigment black 31, 7.8 parts of the above-mentioned pigment dispersant, 148.2 parts of ethylene glycol and 260 parts of glass beads (diameter: 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding and dispersing machine, and filtered with a sieve, thereby obtaining a black pigment dispersion B-1.
Example 2
30.0 parts of the above-mentioned graft-modified carbon black CB-2, 6.0 parts of C.I. pigment black 31, 5.4 parts of the above-mentioned pigment dispersant, 158.6 parts of ethylene glycol and 260 parts of glass beads (diameter: 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding and dispersing machine, and filtered with a sieve, thereby obtaining a black pigment dispersion B-2.
Example 3
40.0 parts of the above-mentioned graft-modified carbon black CB-2, 10.0 parts of C.I. pigment black 31, 10.0 parts of the above-mentioned pigment dispersant, 140 parts of ethylene glycol and 260 parts of glass beads (diameter: 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding and dispersing machine, and filtered with a sieve, thereby obtaining a black pigment dispersion B-3.
Example 4
36.0 parts of the above-mentioned graft-modified carbon black CB-2, 4.0 parts of c.i. pigment black 32, 7.2 parts of the above-mentioned pigment dispersant, 152.8 parts of ethylene glycol and 260 parts of glass beads (diameter 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding and dispersing machine, and filtered with a sieve, thereby obtaining a black pigment dispersion B-4.
Example 5
30.0 parts of the above-mentioned graft-modified carbon black CB-2, 6.0 parts of C.I. pigment black 32, 6.8 parts of the above-mentioned pigment dispersant, 157.2 parts of ethylene glycol and 260 parts of glass beads (diameter: 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding and dispersing machine, and filtered with a sieve, thereby obtaining a black pigment dispersion B-5.
Example 6
40.0 parts of the above-mentioned graft-modified carbon black CB-2, 8.0 parts of C.I. pigment black 32, 9.6 parts of the above-mentioned pigment dispersant, 142.4 parts of ethylene glycol and 260 parts of glass beads (diameter: 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding and dispersing machine, and filtered with a sieve, thereby obtaining a black pigment dispersion B-6.
Comparative example 1
36.0 parts of commercially available c.i. pigment black 7, 8.0 parts of c.i. pigment black 31, 7.8 parts of the above pigment dispersant, 148.2 parts of ethylene glycol and 260 parts of glass beads (diameter 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding disperser, and filtered with a sieve, thereby obtaining black pigment dispersion C-1.
Comparative example 2
36.0 parts of the above-mentioned graft-modified carbon black CB-2, 8.0 parts of C.I. pigment black 31, 7.8 parts of a commercially available pigment dispersant (Dispersogen LFS), 148.2 parts of ethylene glycol and 260 parts of glass beads (diameter 1 mm) were mixed, ground and dispersed for 3 hours using a vertical mill disperser, and filtered with a sieve, to obtain a black pigment dispersion C-2.
Comparative example 3
44.0 parts of a commercially available c.i. pigment black 7, 7.8 parts of the above pigment dispersant, 148.2 parts of ethylene glycol and 260 parts of glass beads (diameter 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding disperser, and filtered with a sieve, thereby obtaining a black pigment dispersion C-3.
Comparative example 4
36.0 parts of commercially available c.i. pigment black 7, 4.0 parts of c.i. pigment black 32, 7.2 parts of the above pigment dispersant, 152.8 parts of ethylene glycol and 260 parts of glass beads (diameter 1 mm) were mixed, ground and dispersed for 3 hours using a vertical grinding disperser, and filtered with a sieve, thereby obtaining black pigment dispersion C-4.
Comparative example 5
36.0 parts of the above-mentioned graft-modified carbon black CB-2, 4.0 parts of C.I. pigment black 32, 7.2 parts of a commercially available pigment dispersant (Dispersogen LFS), 152.8 parts of ethylene glycol and 260 parts of glass beads (diameter 1 mm) were mixed, ground and dispersed for 3 hours using a vertical mill disperser, and filtered with a sieve, thereby obtaining a black pigment dispersion C-4.
4. Evaluation of dispersion stability of Black pigment Dispersion
The laser particle size analysis technique is the most important analysis method of particle size distribution of fine particle dispersion systems at present. The particle diameters of the carbon black pigment dispersions prepared in examples 1 to 6 and comparative examples 1 to 5 were measured using a Nano-ZS90 laser particle sizer, and the particle diameters after 30 days of standing at normal temperature were measured, and the measurement results are shown in table 1 in detail.
Table 1: particle size of carbon black pigment Dispersion prepared in examples and comparative examples
From this, it was revealed that the carbon black pigment dispersions of examples 1 to 6 had little change in particle diameter after standing for 30 days, indicating that the dispersion stability of the dispersions obtained in this application was good, whereas the carbon black pigment dispersions of comparative examples 1 to 5 had a greatly increased particle diameter after standing for 30 days, indicating that the dispersion effect was poor using commercially available c.i. pigment black 7 or commercially available pigment dispersant (Dispersogen LFS), and that pigment particles were re-aggregated after storage for a certain period of time.
5. Evaluation of pigment dispersibility in Black polyester
Preparation of colored polyesters:
application example: the colored polyester was prepared according to the addition amount of the pigment content to the colored polyester of 2 wt.%. Namely: the method comprises the steps of mixing refined terephthalic acid and ethylene glycol, and then reacting in a first esterification kettle and a second esterification kettle to obtain polyester esterified oligomer, wherein a catalyst is added in the second esterification kettle, then adding black pigment dispersion diluent into the polyester esterified oligomer, and sequentially passing through a pre-polycondensation kettle and a final polycondensation kettle to prepare colored slices according to the national standard GB/T14190-2017 fiber-grade Polyester (PET) slice test method.
The carbon black pigment dispersions prepared in examples 1 to 6 and comparative examples 1 to 5 were prepared as colored chips in the above-described manner, and were labeled as PET-B-1 to PET-B-6 (corresponding to examples 1 to 6) and PET-C-1 to PET-C-5 (corresponding to examples 1 to 5) in this order, respectively. In the course of preparing the colored chips, the carbon black pigment dispersions prepared in examples 1 to 6 had no carbon black precipitation phenomenon in the esterification vessel, and the carbon black pigment dispersions prepared in comparative examples 1 to 5 had carbon black precipitation phenomena to different extents.
Filtration performance test:
adding 500g PET slice flushing equipment to make melt pressure curve run stably, recording initial pressure P 0 The method comprises the steps of carrying out a first treatment on the surface of the Then 4000g of the above-mentioned colored chips are added, after the material is used up, 500g of PET chips are added, and the highest pressure P in the test process is recorded max The black pigment content in the colored chips was known to be 80g, the pressure difference Δp=p max -P 0 . The experiment used a 10 μm filter screen. Through this test, the spinnability of the colored sections was evaluated.
Table 2 results of the filtration performance test of the colored sections of examples and comparative examples
| Application example | ΔP(MPa) |
| PET-B-1 | 1.2 |
| PET-B-2 | 1.0 |
| PET-B-3 | 0.80 |
| PET-B-4 | 0.93 |
| PET-B-5 | 1.2 |
| PET-B-6 | 0.80 |
| PET-C-1 | 3.0 |
| PET-C-2 | 5.0 |
| PET-C-3 | 3.2 |
| PET-C-4 | 2.9 |
| PET-C-5 | 4.5 |
As can be seen, the pressure difference between PET-B-1 and PET-B-6 was much smaller than that between PET-C-1 and PET-C-5, so that the dispersion of the carbon black pigment dispersion obtained in examples 1 to 6 in the polyester was good.
Through the test, the modified C.I. pigment black 7 used in the application can be verified, and the dispersion stability of the modified C.I. pigment black 7 in polyester is further improved by utilizing the similar compatibility of the modified grafting end and the polyester; the used pigment dispersing agent is aliphatic hyperbranched polyester with hydrophobic groups and hydrophilic groups, and monomers forming the substance grow in three dimensions in the polymerization process to form a highly branched structure, and pigment particles are fully segmented through steric hindrance, so that aggregation of the pigment particles is avoided.
It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (5)
1. A black pigment dispersion for polyester in-situ polymerization, which is characterized in that: the black pigment is a mixture of modified C.I. pigment black 7 and C.I. pigment black 31, or a mixture of modified C.I. pigment black 7 and C.I. pigment black 32;
the preparation method of the modified C.I. pigment black 7 comprises the following steps: firstly oxidizing pigment black 7 by formaldehyde and sodium hydroxide to obtain hydroxymethyl carbon black, and then grafting the hydroxymethyl carbon black by adipic acid and glycerol to obtain grafted modified carbon black;
the pigment dispersant is obtained by grafting diethyl malonate and 4-bromobutyl acetate, hydrolyzing to obtain dicarboxylic acid unit alcohol monomer, and polymerizing the monomer under the action of a catalyst and temperature.
2. The black pigment dispersion for polyester in-situ polymerization according to claim 1, wherein: the polyol is ethylene glycol.
3. The black pigment dispersion for polyester in-situ polymerization according to claim 1, wherein: the weight average molecular weight of the pigment dispersant is 5000-45000, and the number average molecular weight of the pigment dispersant is 1000-15000.
4. The black pigment dispersion for polyester in-situ polymerization according to claim 1, wherein: the weight of the black pigment accounts for 18-25% of the total weight of the black pigment dispersion, the weight of the pigment dispersing agent accounts for 15-20% of the total weight of the black pigment, and the balance is polyol.
5. A method for producing a black pigment dispersion for polyester in-situ polymerization according to any one of claims 1 to 4, characterized in that: the black pigment, the pigment dispersing agent and the polyol are mixed at high speed, and then ground and filtered to obtain the black pigment dispersion.
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| CN113956686A (en) * | 2021-11-09 | 2022-01-21 | 苏州世名科技股份有限公司 | Carbon black dispersion and preparation method and application thereof |
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