WO2021226941A1 - Dioxazine pigment composition and method for manufacturing same - Google Patents
Dioxazine pigment composition and method for manufacturing same Download PDFInfo
- Publication number
- WO2021226941A1 WO2021226941A1 PCT/CN2020/090283 CN2020090283W WO2021226941A1 WO 2021226941 A1 WO2021226941 A1 WO 2021226941A1 CN 2020090283 W CN2020090283 W CN 2020090283W WO 2021226941 A1 WO2021226941 A1 WO 2021226941A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- oxazine
- pigment
- pigment composition
- hydrogen atom
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 146
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title abstract description 6
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 title abstract 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 27
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical group COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
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- 229940095102 methyl benzoate Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- BYVSMDBDTBXASR-UHFFFAOYSA-N 5,6-dihydro-4h-oxazine Chemical compound C1CON=CC1 BYVSMDBDTBXASR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 3
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 abstract description 9
- 239000011593 sulfur Substances 0.000 abstract description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 239000004698 Polyethylene Substances 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
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- AAISFOKTTIQKLN-UHFFFAOYSA-N 3-[3-[(2-methylpropan-2-yl)oxy]propoxy]propan-1-ol Chemical compound CC(C)(C)OCCCOCCCO AAISFOKTTIQKLN-UHFFFAOYSA-N 0.000 description 1
- NTKBNCABAMQDIG-UHFFFAOYSA-N 3-butoxypropan-1-ol Chemical compound CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 1
- QJRKNPUNWGNXQR-UHFFFAOYSA-N 3-butyl-2-phenylphenol Chemical compound CCCCC1=CC=CC(O)=C1C1=CC=CC=C1 QJRKNPUNWGNXQR-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- GBSGXZBOFKJGMG-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-ol Chemical compound CC(C)OCCCO GBSGXZBOFKJGMG-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WARMTAFWUSJDQG-UHFFFAOYSA-N CC[n](c1c2cccc1)c(cc1)c2c2c1N=C1C(Cl)=C3Oc(c4c(cc5)[n](CC)c6ccccc46)c5N=C3C=C1O2 Chemical compound CC[n](c1c2cccc1)c(cc1)c2c2c1N=C1C(Cl)=C3Oc(c4c(cc5)[n](CC)c6ccccc46)c5N=C3C=C1O2 WARMTAFWUSJDQG-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000003876 biosurfactant Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- 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
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
Definitions
- the present invention involves two Oxazine pigment composition and two Manufacturing method of oxazine pigment composition.
- CI Pigment Violet 23 The oxazine pigment has a vivid purple color, strong coloring power, and heat resistance, so it can be used in various scenes such as printing inks, paints, colored molded products, and printing and dyeing.
- CI Pigment Violet 23 is generally synthesized by condensing 3-amino-9-ethylcarbazole and tetrachlorobenzoquinone, and then closing the ring using a ring-closing agent such as benzenesulfonyl chloride (BSC).
- BSC benzenesulfonyl chloride
- Patent Document 1 Japanese Patent Application Publication No. 2006-126440
- the BSC used in the oxazine pigment does not directly remain in the synthesized pigment, it may cause sulfur-containing element impurities in the final product pigment. Visible light absorption wavelength of sulfur-containing impurities Since oxazine pigments are different, they may affect the hue by reducing the saturation. The sulfur-containing impurities cannot be easily removed by washing pigments or the like.
- BSC decomposes to generate hydrochloric acid, which may cause accelerated corrosion of manufacturing equipment.
- BSC itself has strong toxicity, etc., so it is preferable not to use BSC in the manufacturing process.
- CI Pigment Violet 23 and other two
- the oxazine pigment is generally difficult to disperse, and it is necessary to improve the dispersibility when used in printing inks and the like.
- the problem to be solved by the present invention is to provide a new type of pigment that is unlikely to contain sulfur-containing impurities in the final product. Manufacturing method of oxazine pigment composition. In addition, provide a new type of two with excellent dispersibility and dispersion stability Oxazine pigment composition.
- the inventors of the present invention have conducted in-depth research on the new two that does not use BSC.
- the synthesis route of oxazine pigments as a result, by using a combination of two specific catalysts, the above-mentioned problems can be solved, and the resulting two Since the oxazine pigment composition contains a specific pigment derivative having a hydroxyl group, it is excellent in dispersibility and dispersion stability, thereby completing the present invention.
- the present invention relates to the following.
- Item 1 One of two An oxazine pigment composition comprising two represented by the following formula (I) An oxazine pigment and a pigment derivative represented by the following formula (II).
- R 1 and R 2 in formula (I) each independently represent a hydrogen atom or a halogen atom
- R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group
- R 5 in formula (II) represents a hydrogen atom or a halogen atom
- R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group
- Oxazine pigment composition relative to the two represented by formula (I) 100 parts by mass of the oxazine pigment contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II).
- Item 3 A printing ink containing the two described in item 1 or 2 Oxazine pigment composition.
- Item 4 One of two The method for producing the oxazine pigment composition is obtained by causing a compound represented by the following formula (III) and a compound represented by the following formula (IV) to undergo a cyclization reaction in a solvent in the presence of a 2- to 4-valent metal salt. Contains two represented by the following formula (I) Two of the oxazine pigment and the pigment derivative represented by the following formula (II) Oxazine pigment composition.
- R 1 and R 2 in formula (III) each independently represent a hydrogen atom or a halogen atom
- R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group
- R 8 in the formula (IV) represents a hydrogen atom, a hydroxyl group, an alkoxy group or siloxy group having 1 to 4 carbon atoms]
- R 1 and R 2 in formula (I) each independently represent a hydrogen atom or a halogen atom
- R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group
- R 5 in formula (II) represents a hydrogen atom or a halogen atom
- R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group
- the method for producing the oxazine pigment composition uses 0.01 to 0.3 moles of the compound represented by the formula (IV) and 0.05 to 1.0 moles of the tetravalent metal salt relative to 1 mole of the compound represented by the formula (III).
- the aforementioned solvent is methyl benzoate, 1,2-dichlorobenzene, N-methylpyrrolidone, 3-methoxybutanol, or dimethylsulfoxide.
- Item 7 The two according to any one of items 4 to 6
- the manufacturing method of the oxazine pigment composition, relative to the two represented by the formula (I) 100 parts by mass of the oxazine pigment contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II).
- the manufacturing method of the oxazine pigment composition can synthesize dioxins without using BSC.
- the oxazine pigment it is not easy to contain sulfur-containing impurities in the pigment as the final product.
- the oxazine pigment composition has excellent dispersibility and dispersion stability.
- R 1 and R 2 in formula (I) each independently represent a hydrogen atom or a halogen atom
- R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group
- R 5 in formula (II) represents a hydrogen atom or a halogen atom
- R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group
- the oxazine pigment is preferably CI Pigment Violet 23 in which R 1 and R 2 are chlorine atoms and R 3 and R 4 are ethyl (C 2 H 5 ) in the formula (I) from the viewpoint of usefulness as a pigment.
- the oxazine pigment may contain two or more compounds.
- two The oxazine pigment may be any stereoisomer of the trans form and the cis form.
- the above pigment derivatives are two A compound in which at least a part of the hydrogen atoms in the oxazine structure is substituted with a hydroxyl group (-OH).
- the pigment derivatives mentioned above help to improve the two Dispersibility and dispersion stability in oxazine pigments.
- R 5 in the formula (II) is preferably a hydrogen atom, a chlorine atom or a bromine atom, and more preferably a hydrogen atom or a chlorine atom.
- R 6 and R 7 in formula (II) and two
- the oxazine pigment is also preferably ethyl (C 2 H 5 ).
- the pigment derivative represented by formula (II) two or more kinds of compounds may be contained.
- the above-mentioned pigment derivatives may be any one of trans and cis stereoisomers.
- two The presence of the above-mentioned pigment derivative in the oxazine pigment composition can be confirmed by mass analysis (mass spectrometry) or the like.
- the second aspect of the present invention In the oxazine pigment composition, relative to the two represented by formula (I) 100 parts by mass of the oxazine pigment preferably contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II), more preferably 0.5 to 5.0 parts by mass.
- the ratio of the pigment derivative can be measured by field analysis mass analysis (FD-MS) or the like.
- the second of the present invention In the oxazine pigment composition, in addition to the two represented by the above formula (I) In addition to the oxazine pigment and the pigment derivative represented by the formula (II), it can also be combined with two As the oxazine pigment, a commonly used known dispersant or the like is used together.
- the oxazine pigment composition may also contain the above-mentioned two Violet, red, blue, yellow and other pigments other than oxazine pigments.
- the second of the present invention The method for producing the oxazine pigment composition is obtained by subjecting a compound represented by the following formula (III) and a compound represented by the following formula (IV) to a cyclization reaction in a solvent in the presence of a 2- to 4-valent metal salt.
- the above formula (I) represents two Oxazine pigment and the pigment derivative represented by the above formula (II), that is, the above two of the present invention Method of oxazine pigment composition.
- R 1 and R 2 in formula (III) each independently represent a hydrogen atom or a halogen atom
- R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group
- R 8 in the formula (IV) represents a hydrogen atom, a hydroxyl group, an alkoxy group or siloxy group having 1 to 4 carbon atoms]
- R 1 to R 4 in the formula (III) are the same as those represented by the above formula (I)
- the oxazine pigment is the same. That is to say, R 1 and R 2 in formula (III) after cyclization are two R 1 and R 2 in the oxazine pigment, R 3 and R 4 in formula (III) are the two after cyclization It becomes R 3 and R 4 in the oxazine pigment.
- the compound represented by formula (III) can be synthesized by, for example, the method described in paragraph [0016] of the Chinese Publication CN104031400A.
- the divalent to tetravalent metal salt functions as a catalyst in the cyclization reaction together with the compound represented by formula (IV).
- the 2- to 4-valent metal salt is composed of 2- to 4-valent metal cations and inorganic or organic anions.
- the divalent to tetravalent metal salt may be an anhydrate or a hydrate.
- As the element of the tetravalent metal cation Mg, Al, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Ge, Sr, Y, Zr, Nb, Mo , Tc, Ru, Rh, Pd, Ag, Cd, In, Sn, Sb, etc.
- Zn, Cu, Fe, Ti, Al, and Zr are preferred from the viewpoint of yield.
- inorganic or organic anions include chloride anions, nitrate anions, sulfuric acid anions, phosphoric acid anions, borate anions, fluoride anions, formate anions, acetate anions, citrate anions, and oxalate anions.
- Preference is given to chloride anions and acetate anions.
- 2-4 valent metal salt for example, zinc chloride (ZnCl 2 ), copper chloride (CuCl 2 ), iron chloride (FeCl 3 ), titanium chloride (TiCl 4 ), aluminum chloride (AlCl 3 ), zirconium chloride (ZrCl 4 ), copper acetate (Cu(OAc) 2 ).
- ZnCl 2 zinc chloride
- CuCl 2 copper chloride
- FeCl 3 iron chloride
- TiCl 4 titanium chloride
- AlCl 3 aluminum chloride
- zirconium chloride ZrCl 4
- copper acetate Cu(OAc) 2
- a commercially available reagent can be used.
- zinc chloride (ZnCl 2 ) a reagent manufactured by Kanto Chemical Co., Ltd. can be used.
- the compound represented by the formula (IV) functions as a catalyst in the cyclization reaction together with the tetravalent metal salt.
- R 8 is obtained 2,2,6,6-tetramethyl-piperidine-1-oxide of the hydrogen atom (TEMPO), R 8 is 4-hydroxy-2-hydroxy ,2,6,6,-tetramethylpiperidinyloxy radical, 4-methoxy-2,2,6,6,-tetramethylpiperidinyloxy radical whose R 8 is a methoxy group.
- TEMPO 2,2,6,6-tetramethyl-piperidine-1-oxide of the hydrogen atom
- R 8 is 4-hydroxy-2-hydroxy ,2,6,6,-tetramethylpiperidinyloxy radical, 4-methoxy-2,2,6,6,-tetramethylpiperidinyloxy radical whose R 8 is a methoxy group.
- TEMPO 2,2,6,6-tetramethyl-piperidine-1-oxide of the hydrogen atom
- R 8 is 4-hydroxy-2-hydroxy ,2,6,6,-t
- the cyclization reaction using the compound represented by the formula (IV) and the two to tetravalent metal salts in combination with the two types of catalysts can efficiently obtain the two Oxazine pigment composition.
- the mechanism of the cyclization reaction is not necessarily clear, but it is presumed that the metal atom is coordinated with the nitrogen and oxygen atoms of the compound represented by formula (III) to activate the molecule of formula (III), represented by TEMPO
- the method for producing the oxazine pigment composition it is preferable to use 0.01 to 0.3 moles of the compound represented by the formula (IV) and 0.05 to 1.0 moles of the tetravalent metal salt relative to 1 mole of the compound represented by the formula (III). It is preferable to use 0.1 to 0.2 moles of the compound represented by the formula (IV) and use 0.1 to 0.8 moles of the divalent to tetravalent metal salt. By using the catalyst in this ratio, it is possible to more effectively obtain the two Oxazine pigment composition.
- the solvent used in the cyclization reaction only needs to be able to dissolve the compound represented by the formula (III) and the compound represented by the formula (IV), and methyl benzoate, 1,2-dichlorobenzene, N-methylpyrrolidone, 3-Methoxybutanol, butyl phenyl ether, solvent naphtha or dimethyl sulfoxide, etc.
- the cyclization reaction is carried out by adding these compounds and a catalyst to a solvent, stirring and heating.
- the reaction temperature is, for example, 100 to 250°C, preferably 130 to 200°C.
- the reaction time is, for example, 2 to 48 hours, preferably 4 to 24 hours.
- the resulting crude product is washed with water and solvent, filtered, and heated and dried to obtain two Oxazine pigment composition.
- the second of the present invention The oxazine pigment composition has excellent dispersibility and dispersion stability, so it is particularly useful as a printing ink.
- the oxazine pigment composition is not particularly limited, and preferably contains known and customary binder resins, solvents, additives, etc. that can be used in general printing inks.
- the above two in the printing ink of the present invention The amount of the oxazine pigment composition is preferably 2 to 60% by mass, more preferably 4 to 25% by mass.
- binder resin examples include nitrocellulose resin, polyamide resin, polyurethane resin, and acrylic resin.
- the amount of the binder resin in the printing ink of the present invention is preferably 1 to 30% by mass, more preferably 3 to 20% by mass.
- the solvent examples include aromatic organic solvents such as toluene and xylene; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; acetic acid Ester solvents such as ethyl, n-propyl acetate, isopropyl acetate, isobutyl acetate; alcoholic solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, etc.; Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl Ether, ethylene glycol mono-ter
- surfactants As the above additives, surfactants, gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleic rosin, hardened rosin, phthalic alkyd resin and other rosins, pigment derivatives, dispersants, wetting agents can be used , Adhesive aids, leveling agents, defoamers, antistatic agents, trapping agents, anti-blocking agents, wax components, etc.
- the above-mentioned surfactant is added in order to adjust ink characteristics such as surface tension.
- the surfactants that can be added for this purpose are not particularly limited, and various anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, etc. can be mentioned. Among them, anionic surfactants are preferred. Agent, non-ionic surfactant.
- anionic surfactants include alkylbenzene sulfonates, alkylphenyl sulfonates, alkylnaphthalene sulfonates, higher fatty acid salts, sulfate ester salts of higher fatty acid esters, and higher fatty acid esters.
- nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan Alcohol fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkylamine, polyoxyethylene fatty acid Amides, fatty acid alkynolamides, alkyl alkanolamides, acetylene glycol, ethylene oxide adducts of acetylene glycol, polyethylene glycol-polypropylene glycol block copolymers, etc.
- polyoxyethylene nonyl is preferred Phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene dodecyl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene Sorbitan fatty acid ester, fatty acid alkynolamide, acetylene glycol, ethylene oxide adduct of acetylene glycol, polyethylene glycol-polypropylene glycol block copolymer.
- polysiloxane-based surfactants such as polysiloxane ethylene oxide adducts can also be used; perfluoroalkyl carboxylate, perfluoroalkyl sulfonate, ethylene oxide perfluoro Fluorine-based surfactants such as alkyl ethers; biosurfactants such as echinosporic acid, rhamnolipids, lysolecithin, etc.
- surfactants may be used singly, or two or more of them may be mixed and used.
- the addition amount is preferably in the range of 0.001 to 2% by mass relative to the total mass of the ink, more preferably in the range of 0.001 to 1.5% by mass, and still more preferably in the range of 0.01 to 1% by mass.
- preservatives can be further added as additives.
- the printing ink of the present invention can be The oxazine pigment composition, the binder resin, and the additives are dispersed in a solvent to be manufactured.
- a disperser used for the dispersion, a disperser, a homomixer, a paint conditioner, a Scandex mixer, a bead mill, an attritor, a ball mill, a two-roll mill, a three-roll mill, and a pressure kneader can be mentioned. Wait. About Printing Ink C2
- a resin and a solvent are added and dispersed so that the viscosity becomes dispersible by these dispersers.
- the solid content of the dispersed printing ink is, for example, 5 to 50%, and a solvent is further added and mixed to form a printing ink for use.
- the second of the present invention The oxazine pigment composition is particularly useful as a printing ink.
- it can also be used for a wide range of applications such as paint, plastic coloring, inkjet ink, digital toner, cosmetics, color filters, writing utensils, and the like.
- the intermediate 1 is used to produce the two containing the formula (I): Two of the oxazine pigment and the pigment derivative represented by formula (II) Oxazine pigment composition.
- FD-MS measurement mass analysis of this example was performed as follows: 5 mg of the pigment composition obtained in Examples 1 and 2 or the pigment powder obtained in Comparative Example 1 was dispersed in 1.0 mL of tetrahydrofuran The mass analysis was carried out using an FD-MS measuring device JMS-T100GC (manufactured by JEOL Ltd.).
- the oxazine pigment composition 1 was subjected to FD-MS measurement (mass analysis), and as a result, peaks of m/z 536 and 570 were detected. It can be seen that two In addition to CI Pigment Violet 23, the oxazine pigment composition 1 also contains the following pigment derivatives 1 (nominal mass: 570) and pigment derivatives 2 (nominal mass: 536).
- the resulting filter cake is heated and dried to obtain two Oxazine pigment composition 2 (2.7 g, yield 46%).
- the oxazine pigment composition 1 was subjected to FD-MS measurement (mass analysis), and as a result, peaks of m/z 536 and 570 were detected. It can be seen that two As in Example 1, the oxazine pigment composition 2 contains CI Pigment Violet 23 and also contains pigment derivative 1 (nominal mass: 570) and pigment derivative 2 (nominal mass: 536).
- the CI Pigment Violet 23 was synthesized with reference to paragraph [0067] of JP 2004-189668 A.
- the oxazine pigment was subjected to FD-MS measurement (mass analysis), and as a result, no peaks of m/z 536 and 570 were detected. From this, it can be seen that the synthesis method of Comparative Example 1 does not contain a pigment derivative. In addition, peaks of m/z 628, 634, and 662 were detected. It is estimated that these molecular weight peaks are impurities containing sulfur elements described below. From this, it can be seen that the synthesis method of Comparative Example 1 contains sulfur-containing impurities.
- the two obtained from Examples 1 and 2 Oxazine pigment composition the two obtained from Comparative Example 1
- the dispersibility and dispersion stability are evaluated. About 10 mg of the pigment composition or the powder of the pigment was put into a 10 mL glass bottle containing 5 ml of water as a dispersion medium, and ultrasonic waves were applied to disperse it.
- the dispersibility was evaluated immediately after the ultrasonic wave was applied (0h), and the dispersion stability was evaluated after 18h and 72h.
- the evaluation criteria are as follows.
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Abstract
The subject of the present invention is to provide a method for manufacturing a new dioxazine pigment composition that is not prone to containing impurities containing sulfur, etc. in the pigment as a final product. In addition, a new dioxazine pigment composition having an excellent dispersibility and dispersion stability is provided. The solution is a dioxazine pigment composition comprising a dioxazine pigment as represented by the following formula (I) and a pigment derivative represented by the following formula (II). [The specifications in formulas (I) and (II) are as specified in the present description.]
Description
本发明涉及二
嗪颜料组合物和二
嗪颜料组合物的制造方法。
The present invention involves two Oxazine pigment composition and two Manufacturing method of oxazine pigment composition.
紫色颜料中，以C.I.颜料紫23为代表的二
嗪颜料为鲜明的紫色且着色力强、具有耐热性，因此是可在印刷油墨、涂料、着色成形品、印染等各种场景中使用的颜料。C.I.颜料紫23通常通过使3-氨基-9-乙基咔唑与四氯苯醌缩合后，使用苯磺酰氯(BSC)等闭环剂使其闭环来合成。关于这样合成C.I.颜料紫23，例如在下述专利文献1中有所记载。
Among the purple pigments, two represented by CI Pigment Violet 23 The oxazine pigment has a vivid purple color, strong coloring power, and heat resistance, so it can be used in various scenes such as printing inks, paints, colored molded products, and printing and dyeing. CI Pigment Violet 23 is generally synthesized by condensing 3-amino-9-ethylcarbazole and tetrachlorobenzoquinone, and then closing the ring using a ring-closing agent such as benzenesulfonyl chloride (BSC). Regarding the synthesis of CI Pigment Violet 23 in this manner, for example, it is described in Patent Document 1 below.
现有技术文献Prior art literature
专利文献Patent literature
专利文献1：日本特开2006-126440号公报Patent Document 1: Japanese Patent Application Publication No. 2006-126440
发明内容Summary of the invention
发明要解决的课题The problem to be solved by the invention
在上述那样合成C.I.颜料紫23等二
嗪颜料时使用的BSC虽然不会在合成后的颜料中直接残留，但有时会在作为最终制品的颜料中成为含硫元素杂质的原因。含硫元素杂质的可见光吸收波长与二
嗪颜料不同，因此有时会使饱和度降低等而对色相产生影响。该含硫元素杂质无法通过清洗颜料等而容易地除去。另外，BSC会分解而产生盐酸，成为制造设备加快腐蚀的原因，而且，BSC自身具有强毒性等，在制造工序中优选不使用BSC。
Synthesize CI Pigment Violet 23 etc. as above Although the BSC used in the oxazine pigment does not directly remain in the synthesized pigment, it may cause sulfur-containing element impurities in the final product pigment. Visible light absorption wavelength of sulfur-containing impurities Since oxazine pigments are different, they may affect the hue by reducing the saturation. The sulfur-containing impurities cannot be easily removed by washing pigments or the like. In addition, BSC decomposes to generate hydrochloric acid, which may cause accelerated corrosion of manufacturing equipment. In addition, BSC itself has strong toxicity, etc., so it is preferable not to use BSC in the manufacturing process.
进一步，C.I.颜料紫23等二
嗪颜料通常难以分散，在印刷油墨等中使用时需要提高分散性。
Furthermore, CI Pigment Violet 23 and other two The oxazine pigment is generally difficult to disperse, and it is necessary to improve the dispersibility when used in printing inks and the like.
鉴于前述那样的实际情况，本发明要解决的课题在于提供一种在作为最终制品的颜料中不易含有含硫元素杂质的新的二
嗪颜料组合物的制造方法。另外，提供一种具有优异的分散性和分散稳定性的新的二
嗪颜料组合物。
In view of the foregoing actual situation, the problem to be solved by the present invention is to provide a new type of pigment that is unlikely to contain sulfur-containing impurities in the final product. Manufacturing method of oxazine pigment composition. In addition, provide a new type of two with excellent dispersibility and dispersion stability Oxazine pigment composition.
用于解决课题的手段Means to solve the problem
本发明人等深入研究了不使用BSC的新的二
嗪颜料的合成途径，结果发生，通过组合使用特定的2种催化剂，能够解决上述课题，并且，由此得到的二
嗪颜料组合物由于包含具有羟基的特定的颜料衍生物，因此分散性和分散稳定性优异，从而完成了本发明。
The inventors of the present invention have conducted in-depth research on the new two that does not use BSC. The synthesis route of oxazine pigments, as a result, by using a combination of two specific catalysts, the above-mentioned problems can be solved, and the resulting two Since the oxazine pigment composition contains a specific pigment derivative having a hydroxyl group, it is excellent in dispersibility and dispersion stability, thereby completing the present invention.
即，本发明涉及以下内容。That is, the present invention relates to the following.
第1项.一种二
嗪颜料组合物，其包含下述式(I)表示的二
嗪颜料和下述式(II)表示的颜料衍生物。
Item 1. One of two An oxazine pigment composition comprising two represented by the following formula (I) An oxazine pigment and a pigment derivative represented by the following formula (II).
[化1][化1]
[式(I)中的R
1和R
2分别独立地表示氢原子或卤原子，R
3和R
4分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 1 and R 2 in formula (I) each independently represent a hydrogen atom or a halogen atom, and R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group]
[化2][化2]
[式(II)中的R
5表示氢原子或卤原子，R
6和R
7分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 5 in formula (II) represents a hydrogen atom or a halogen atom, R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group]
第2项.根据第1项所述的二
嗪颜料组合物，相对于式(I)表示的二
嗪颜料100质量份，包含0.3～10.0质量份的式(II)表示的颜料衍生物。
Item 2. According to the two mentioned in item 1 Oxazine pigment composition, relative to the two represented by formula (I) 100 parts by mass of the oxazine pigment contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II).
第3项.一种印刷油墨，其含有第1或2项所述的二
嗪颜料组合物。
Item 3. A printing ink containing the two described in item 1 or 2 Oxazine pigment composition.
第4项.一种二
嗪颜料组合物的制造方法，通过使下述式(III)表示的化合物与下述式(IV)表示的化合物在2～4价的金属盐的存在下在溶剂中发生环化反应，从而得到包含下述式(I)表示的二
嗪颜料和下述式(II)表示的颜料衍生物的二
嗪颜料组合物。
Item 4. One of two The method for producing the oxazine pigment composition is obtained by causing a compound represented by the following formula (III) and a compound represented by the following formula (IV) to undergo a cyclization reaction in a solvent in the presence of a 2- to 4-valent metal salt. Contains two represented by the following formula (I) Two of the oxazine pigment and the pigment derivative represented by the following formula (II) Oxazine pigment composition.
[化3][化3]
[式(III)中的R
1和R
2分别独立地表示氢原子或卤原子，R
3和R
4分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 1 and R 2 in formula (III) each independently represent a hydrogen atom or a halogen atom, R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group]
[化4][化4]
[式(IV)中的R
8表示氢原子、羟基、碳数1～4的烷氧基或甲硅烷氧基]
[R 8 in the formula (IV) represents a hydrogen atom, a hydroxyl group, an alkoxy group or siloxy group having 1 to 4 carbon atoms]
[化5][化5]
[式(I)中的R
1和R
2分别独立地表示氢原子或卤原子，R
3和R
4分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 1 and R 2 in formula (I) each independently represent a hydrogen atom or a halogen atom, and R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group]
[化6][化6]
[式(II)中的R
5表示氢原子或卤原子，R
6和R
7分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 5 in formula (II) represents a hydrogen atom or a halogen atom, R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group]
第5项.根据第4项所述的二
嗪颜料组合物的制造方法，相对于式(III)表示的化合物1摩尔，使用0.01～0.3摩尔的式(IV)表示的化合物，并且使用0.05～1.0摩尔的2～4价的金属盐。
Item 5. According to the second mentioned in item 4 The method for producing the oxazine pigment composition uses 0.01 to 0.3 moles of the compound represented by the formula (IV) and 0.05 to 1.0 moles of the tetravalent metal salt relative to 1 mole of the compound represented by the formula (III).
第6项.根据第4或5项所述的二
嗪颜料组合物的制造方法，前述溶剂为苯甲酸甲酯、1,2-二氯苯、N-甲基吡咯烷酮、3-甲氧基丁醇或二甲基亚砜。
Item 6. According to item 4 or 5, the two In the method for producing the oxazine pigment composition, the aforementioned solvent is methyl benzoate, 1,2-dichlorobenzene, N-methylpyrrolidone, 3-methoxybutanol, or dimethylsulfoxide.
第7项.根据第4～6项中任一项所述的二
嗪颜料组合物的制造方法，相对于式(I)表示的二
嗪颜料100质量份，包含0.3～10.0质量份的式(II)表示的颜料衍生物。
Item 7. The two according to any one of items 4 to 6 The manufacturing method of the oxazine pigment composition, relative to the two represented by the formula (I) 100 parts by mass of the oxazine pigment contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II).
发明效果Invention effect
根据本发明的二
嗪颜料组合物的制造方法，由于能够在不使用BSC的情况下合成二
嗪颜料，因此在作为最终制品的颜料中不易包含含硫元素的杂质。另外，本发明的二
嗪颜料组合物具有优异的分散性和分散稳定性。
According to the second aspect of the present invention The manufacturing method of the oxazine pigment composition can synthesize dioxins without using BSC. As the oxazine pigment, it is not easy to contain sulfur-containing impurities in the pigment as the final product. In addition, the second aspect of the present invention The oxazine pigment composition has excellent dispersibility and dispersion stability.
[二
嗪颜料组合物]
[two Oxazine pigment composition]
本发明的二
嗪颜料组合物包含式(I)表示的二
嗪颜料和式(II)表示的颜料衍生物。
The second of the present invention The oxazine pigment composition comprises two represented by formula (I) Oxazine pigments and pigment derivatives represented by formula (II).
[化7][化7]
[式(I)中的R
1和R
2分别独立地表示氢原子或卤原子，R
3和R
4分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 1 and R 2 in formula (I) each independently represent a hydrogen atom or a halogen atom, and R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group]
[化8][化8]
[式(II)中的R
5表示氢原子或卤原子，R
6和R
7分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 5 in formula (II) represents a hydrogen atom or a halogen atom, R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group]
作为上述二
嗪颜料，从作为颜料的有用性这一点考虑，优选式(I)中R
1和R
2为氯原子、R
3和R
4为乙基(C
2H
5)的C.I.颜料紫23。作为式(I)表示的二
嗪颜料，可含有2种以上的化合物。另外，二
嗪颜料可以为反式、顺式中的任一种立体异构体。
As the above two The oxazine pigment is preferably CI Pigment Violet 23 in which R 1 and R 2 are chlorine atoms and R 3 and R 4 are ethyl (C 2 H 5 ) in the formula (I) from the viewpoint of usefulness as a pigment. As the two represented by formula (I) The oxazine pigment may contain two or more compounds. In addition, two The oxazine pigment may be any stereoisomer of the trans form and the cis form.
上述颜料衍生物为二
嗪结构中的至少一部分氢原子被取代为羟基(-OH)的化合物。上述颜料衍生物有助于提高二
嗪颜料中分散性和分散稳定性。式(II)中的R
5优选氢原子、氯原子或溴原子，更优选氢原子或氯原子。另外，作为式(II)中的R
6和R
7，与二
嗪颜料同样地优选乙基(C
2H
5)。作为式(II)表示的颜料衍生物，可包含2种以上的化合物。另外，与二
嗪颜料同样地，上述颜料衍生物可以为反式、顺式中的任一种立体异构体。二
嗪颜料组合物中上述颜料衍生物的存在可以通过质量分析(质谱)等来确认。
The above pigment derivatives are two A compound in which at least a part of the hydrogen atoms in the oxazine structure is substituted with a hydroxyl group (-OH). The pigment derivatives mentioned above help to improve the two Dispersibility and dispersion stability in oxazine pigments. R 5 in the formula (II) is preferably a hydrogen atom, a chlorine atom or a bromine atom, and more preferably a hydrogen atom or a chlorine atom. In addition, as R 6 and R 7 in formula (II), and two The oxazine pigment is also preferably ethyl (C 2 H 5 ). As the pigment derivative represented by formula (II), two or more kinds of compounds may be contained. In addition, with two As for the oxazine pigments, the above-mentioned pigment derivatives may be any one of trans and cis stereoisomers. two The presence of the above-mentioned pigment derivative in the oxazine pigment composition can be confirmed by mass analysis (mass spectrometry) or the like.
从提高分散性的观点考虑，本发明的二
嗪颜料组合物中，相对于式(I)表示的二
嗪颜料100质量份，优选包含0.3～10.0质量份的式(II)表示的颜料衍生物，更优选包含0.5～5.0质量份。颜料衍生物的比例可以通过场解析质量分析(FD-MS)等来测定。
From the viewpoint of improving dispersibility, the second aspect of the present invention In the oxazine pigment composition, relative to the two represented by formula (I) 100 parts by mass of the oxazine pigment preferably contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II), more preferably 0.5 to 5.0 parts by mass. The ratio of the pigment derivative can be measured by field analysis mass analysis (FD-MS) or the like.
本发明的二
嗪颜料组合物中，除了上述式(I)表示的二
嗪颜料和式(II)表示的颜料衍生物以外，还可以与二
嗪颜料一起使用通常所用的公知的分散剂等。另外，本发明的二
嗪颜料组合物中，还可以包含上述二
嗪颜料以外的紫、红、蓝、黄色等的颜料。
The second of the present invention In the oxazine pigment composition, in addition to the two represented by the above formula (I) In addition to the oxazine pigment and the pigment derivative represented by the formula (II), it can also be combined with two As the oxazine pigment, a commonly used known dispersant or the like is used together. In addition, the second aspect of the present invention The oxazine pigment composition may also contain the above-mentioned two Violet, red, blue, yellow and other pigments other than oxazine pigments.
[二
嗪颜料组合物的制造方法]
[two Manufacturing method of oxazine pigment composition]
本发明的二
嗪颜料组合物的制造方法为通过使下述式(III)表示的化合物与下述式(IV)表示的化合物在2～4价的金属盐的存在下在溶剂中发生环化反应，从而得到上述式(I)表示的二
嗪颜料和上述式(II)表示的颜料衍生物、即上述本发明的二
嗪颜料组合物的方法。
The second of the present invention The method for producing the oxazine pigment composition is obtained by subjecting a compound represented by the following formula (III) and a compound represented by the following formula (IV) to a cyclization reaction in a solvent in the presence of a 2- to 4-valent metal salt. The above formula (I) represents two Oxazine pigment and the pigment derivative represented by the above formula (II), that is, the above two of the present invention Method of oxazine pigment composition.
[化9][化9]
[式(III)中的R
1和R
2分别独立地表示氢原子或卤原子，R
3和R
4分别独立地表示氢原子、碳数1～8的烷基、或苯基]
[R 1 and R 2 in formula (III) each independently represent a hydrogen atom or a halogen atom, R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group]
[化10][化10]
[式(IV)中的R
8表示氢原子、羟基、碳数1～4的烷氧基或甲硅烷氧基]
[R 8 in the formula (IV) represents a hydrogen atom, a hydroxyl group, an alkoxy group or siloxy group having 1 to 4 carbon atoms]
式(III)中的R
1～R
4与上述式(I)表示的二
嗪颜料相同。也就是说，式(III)中的R
1和R
2在环化后的二
嗪颜料中成为R
1和R
2，式(III)中的R
3和R
4在环化后的二
嗪颜料中成为R
3和R
4。式(III)表示的化合物可以通过例如中国公布文本CN104031400A第[0016]段记载的方法来合成。
R 1 to R 4 in the formula (III) are the same as those represented by the above formula (I) The oxazine pigment is the same. That is to say, R 1 and R 2 in formula (III) after cyclization are two R 1 and R 2 in the oxazine pigment, R 3 and R 4 in formula (III) are the two after cyclization It becomes R 3 and R 4 in the oxazine pigment. The compound represented by formula (III) can be synthesized by, for example, the method described in paragraph [0016] of the Chinese Publication CN104031400A.
2～4价的金属盐与式(IV)表示的化合物一起在环化反应中作为催化剂发挥作用。2～4价的金属盐由2～4价的金属阳离子和无机或有机阴离子构成。2～4价的金属盐可以为无水物也可以为水合物。作为2～4价的金属阳离子的元素，可列举Mg、Al、Ca、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Sr、Y、Zr、Nb、Mo、Tc、Ru、Rh、Pd、Ag、Cd、In、Sn、Sb等，其中，从收获率这一点考虑优选Zn、Cu、Fe、Ti、Al、Zr。作为无机或有机阴离子，可列举氯化物阴离子、硝酸阴离子、硫酸阴离子、磷酸阴离子、硼酸阴离子、氟化物阴离子、甲酸阴离子、乙酸阴离子、柠檬酸阴离子、草酸阴离子，其中，从收获率这一点考虑，优选氯化物阴离子和乙酸阴离子。作为上述2～4价的金属盐，可以使用例如氯化锌(ZnCl
2)、氯化铜(CuCl
2)、氯化铁(FeCl
3)、氯化钛(TiCl
4)、氯化铝(AlCl
3)、氯化锆(ZrCl
4)、乙酸铜(Cu(OAc)
2)。作为2～4价的金属盐，可以使用市售的试剂，例如氯化锌(ZnCl
2)可以使用关东化学株式会社制试剂。
The divalent to tetravalent metal salt functions as a catalyst in the cyclization reaction together with the compound represented by formula (IV). The 2- to 4-valent metal salt is composed of 2- to 4-valent metal cations and inorganic or organic anions. The divalent to tetravalent metal salt may be an anhydrate or a hydrate. As the element of the tetravalent metal cation, Mg, Al, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Ge, Sr, Y, Zr, Nb, Mo , Tc, Ru, Rh, Pd, Ag, Cd, In, Sn, Sb, etc. Among them, Zn, Cu, Fe, Ti, Al, and Zr are preferred from the viewpoint of yield. Examples of inorganic or organic anions include chloride anions, nitrate anions, sulfuric acid anions, phosphoric acid anions, borate anions, fluoride anions, formate anions, acetate anions, citrate anions, and oxalate anions. Among them, from the viewpoint of yield, Preference is given to chloride anions and acetate anions. As the above-mentioned 2-4 valent metal salt, for example, zinc chloride (ZnCl 2 ), copper chloride (CuCl 2 ), iron chloride (FeCl 3 ), titanium chloride (TiCl 4 ), aluminum chloride (AlCl 3 ), zirconium chloride (ZrCl 4 ), copper acetate (Cu(OAc) 2 ). As the divalent to tetravalent metal salt, a commercially available reagent can be used. For example, for zinc chloride (ZnCl 2 ), a reagent manufactured by Kanto Chemical Co., Ltd. can be used.
式(IV)表示的化合物与2～4价的金属盐一起在环化反应中作为催化剂发挥作用。作为这样的式(IV)表示的化合物，可以获得R
8为氢原子的2,2,6,6-四甲基哌啶1-氧化物(TEMPO)、R
8为羟基的4-羟基-2,2,6,6,-四甲基哌啶氧自由基、R
8为甲氧基的4-甲氧基-2,2,6,6,-四甲基哌啶氧自由基。作为式(IV)表示的化合物，可以使用市售的试剂，例如作为TEMPO，可以使用关东化学株式会社制试剂。
The compound represented by the formula (IV) functions as a catalyst in the cyclization reaction together with the tetravalent metal salt. As the compound represented by such formula (IV), R 8 is obtained 2,2,6,6-tetramethyl-piperidine-1-oxide of the hydrogen atom (TEMPO), R 8 is 4-hydroxy-2-hydroxy ,2,6,6,-tetramethylpiperidinyloxy radical, 4-methoxy-2,2,6,6,-tetramethylpiperidinyloxy radical whose R 8 is a methoxy group. As the compound represented by the formula (IV), a commercially available reagent can be used. For example, as TEMPO, a reagent manufactured by Kanto Chemical Co., Ltd. can be used.
在本发明的二
嗪颜料组合物的制造方法中，通过组合使用式(IV)表示的化合物和2～4价的金属盐这2种催化剂的环化反应，能够高效率地得到二
嗪颜料组合物。作为该环化反应的机制，不一定明确，但推定为：通过金属原子与式(III)表示的化合物的氮和氧原子进行配位，使得式(III)的分子被活化，以TEMPO为代表的式(IV)的化合物在使式(III)氧化的同时使其闭环，得到二
嗪颜料组合物。
In the second of the present invention In the production method of the oxazine pigment composition, the cyclization reaction using the compound represented by the formula (IV) and the two to tetravalent metal salts in combination with the two types of catalysts can efficiently obtain the two Oxazine pigment composition. The mechanism of the cyclization reaction is not necessarily clear, but it is presumed that the metal atom is coordinated with the nitrogen and oxygen atoms of the compound represented by formula (III) to activate the molecule of formula (III), represented by TEMPO The compound of formula (IV) in the oxidation of formula (III) at the same time to make the ring closed to obtain two Oxazine pigment composition.
在本发明的二
嗪颜料组合物的制造方法中，相对于式(III)表示的化合物1摩尔，优选使用0.01～0.3摩尔的式(IV)表示的化合物并且使用0.05～1.0摩尔的2～4价的金属盐，优选使用0.1～0.2摩尔的式(IV)表示的化合物并且使用0.1～0.8摩尔的2～4价的金属盐。通过以这样的比例使用催化剂，能够更有效地得到二
嗪颜料组合物。
In the second of the present invention In the method for producing the oxazine pigment composition, it is preferable to use 0.01 to 0.3 moles of the compound represented by the formula (IV) and 0.05 to 1.0 moles of the tetravalent metal salt relative to 1 mole of the compound represented by the formula (III). It is preferable to use 0.1 to 0.2 moles of the compound represented by the formula (IV) and use 0.1 to 0.8 moles of the divalent to tetravalent metal salt. By using the catalyst in this ratio, it is possible to more effectively obtain the two Oxazine pigment composition.
环化反应中使用的溶剂只要能够将式(III)表示的化合物、式(IV)表示的化合物溶解即可，优选使用苯甲酸甲酯、1,2-二氯苯、N-甲基吡咯烷酮、3-甲氧基丁醇、丁基苯醚、溶剂石脑油或二甲基亚砜等。The solvent used in the cyclization reaction only needs to be able to dissolve the compound represented by the formula (III) and the compound represented by the formula (IV), and methyl benzoate, 1,2-dichlorobenzene, N-methylpyrrolidone, 3-Methoxybutanol, butyl phenyl ether, solvent naphtha or dimethyl sulfoxide, etc.
环化反应通过在溶剂中加入这些化合物和催化剂并搅拌、加热来进行。反应温度例如为100～250℃、优选为130～200℃。反应时间例如为2～48小时、优选为4～24小时。环化反应后，将所得的粗产物用水、溶剂进行清洗并进行过滤和加热干燥，从而能够得到二
嗪颜料组合物。
The cyclization reaction is carried out by adding these compounds and a catalyst to a solvent, stirring and heating. The reaction temperature is, for example, 100 to 250°C, preferably 130 to 200°C. The reaction time is, for example, 2 to 48 hours, preferably 4 to 24 hours. After the cyclization reaction, the resulting crude product is washed with water and solvent, filtered, and heated and dried to obtain two Oxazine pigment composition.
[印刷油墨][Printing ink]
本发明的二
嗪颜料组合物的分散性和分散稳定性优异，因此作为印刷油墨特别有用。本发明的印刷油墨只要包含上述本发明的二
嗪颜料组合物就没有特别限制，优选包含通常印刷油墨中可使用的公知惯用的粘合剂树脂、溶剂、添加剂等。本发明的印刷油墨中上述二
嗪颜料组合物的量优选为2～60质量％，更优选为4～25质量％。
The second of the present invention The oxazine pigment composition has excellent dispersibility and dispersion stability, so it is particularly useful as a printing ink. As long as the printing ink of the present invention contains the above-mentioned two of the present invention The oxazine pigment composition is not particularly limited, and preferably contains known and customary binder resins, solvents, additives, etc. that can be used in general printing inks. The above two in the printing ink of the present invention The amount of the oxazine pigment composition is preferably 2 to 60% by mass, more preferably 4 to 25% by mass.
作为上述粘合剂树脂，可列举例如硝基纤维素树脂、聚酰胺树脂、聚氨酯树脂、丙烯酸树脂。本发明的印刷油墨中粘合剂树脂的量优选为1～30质量％，更优选3～20质量％。Examples of the above-mentioned binder resin include nitrocellulose resin, polyamide resin, polyurethane resin, and acrylic resin. The amount of the binder resin in the printing ink of the present invention is preferably 1 to 30% by mass, more preferably 3 to 20% by mass.
作为上述溶剂，可列举例如：甲苯、二甲苯等芳香族有机溶剂；甲基乙基酮、甲基异丁基酮、环己酮、2-庚酮、3-庚酮等酮系溶剂；乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸异丁酯等酯系溶剂；甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇等醇系溶剂；乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单正丙基醚、乙二醇单异丙基醚、乙二醇单正丁基醚、乙二醇单异丁基醚、乙二醇单叔丁基醚、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单正丙基醚、丙二醇单异丙基醚、丙二醇单正丁基醚、丙二醇单异丁基醚、丙二醇单叔丁基醚、乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二正丙基醚、 乙二醇二异丙基醚、乙二醇二正丁基醚、乙二醇二异丁基醚、乙二醇二叔丁基醚、丙二醇二甲基醚、丙二醇二甲基醚、丙二醇二正丙基醚、丙二醇二异丙基醚、丙二醇二正丁基醚、丙二醇二异丁基醚、丙二醇二叔丁基醚、二乙二醇单甲基醚、二乙二醇单甲基醚、二乙二醇单正丙基醚、二乙二醇单异丙基醚、二乙二醇单正丁基醚、二乙二醇单异丁基醚、二乙二醇单叔丁基醚、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二正丙基醚、二乙二醇二异丙基醚、二乙二醇二正丁基醚、二乙二醇二异丁基醚、二乙二醇二叔丁基醚、二丙二醇单甲基醚、二丙二醇单乙基醚、二丙二醇单正丙基醚、二丙二醇单异丙基醚、二丙二醇单正丁基醚、二丙二醇单异丁基醚、二丙二醇单叔丁基醚、二丙二醇二甲基醚、二丙二醇二乙基醚、二丙二醇二正丙基醚、二丙二醇二异丙基醚、二丙二醇二正丁基醚、二丙二醇二异丁基醚、二丙二醇二叔丁基醚、乙二醇单甲基醚乙酸酯、乙二醇单乙基醚乙酸酯、丙二醇单乙基醚乙酸酯、丙二醇单甲基醚乙酸酯、二乙二醇单甲基醚乙酸酯、二乙二醇单乙基醚乙酸酯等二醇醚系溶剂。Examples of the solvent include aromatic organic solvents such as toluene and xylene; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; acetic acid Ester solvents such as ethyl, n-propyl acetate, isopropyl acetate, isobutyl acetate; alcoholic solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, etc.; Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl Ether, ethylene glycol mono-tert-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono n-propyl ether, propylene glycol mono isopropyl ether, propylene glycol mono n-butyl ether, propylene glycol mono isobutyl ether , Propylene glycol mono-tert-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol di-n-propyl ether, ethylene glycol diisopropyl ether, ethylene glycol di-n-butyl ether , Ethylene glycol diisobutyl ether, ethylene glycol di-tert-butyl ether, propylene glycol dimethyl ether, propylene glycol dimethyl ether, propylene glycol di-n-propyl ether, propylene glycol diisopropyl ether, propylene glycol di-n-butyl Ether, propylene glycol diisobutyl ether, propylene glycol di-tert-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol monoiso Propyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol monoisobutyl ether, diethylene glycol mono-tert-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl Ether, diethylene glycol di-n-propyl ether, diethylene glycol diisopropyl ether, diethylene glycol di-n-butyl ether, diethylene glycol diisobutyl ether, diethylene glycol di-tert-butyl Ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol mono-n-butyl ether, dipropylene glycol monoisobutyl ether, dipropylene glycol Mono-tert-butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol di-n-propyl ether, dipropylene glycol diisopropyl ether, dipropylene glycol di-n-butyl ether, dipropylene glycol diisobutyl ether Ether, dipropylene glycol di-tert-butyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, Glycol ether solvents such as diethylene glycol monomethyl ether acetate and diethylene glycol monoethyl ether acetate.
作为上述添加剂，可以使用表面活性剂、脂松香、聚合松香、歧化松香、氢化松香、马来松香、硬化松香、邻苯二甲酸醇酸树脂等松香类，颜料衍生物、分散剂、润湿剂、粘接辅助剂、流平剂、消泡剂、抗静电剂、捕捉剂、防粘连剂、蜡成分等。As the above additives, surfactants, gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleic rosin, hardened rosin, phthalic alkyd resin and other rosins, pigment derivatives, dispersants, wetting agents can be used , Adhesive aids, leveling agents, defoamers, antistatic agents, trapping agents, anti-blocking agents, wax components, etc.
上述表面活性剂为了调整表面张力等油墨特性而添加。可为此而添加的表面活性剂没有特别限定，可列举各种阴离子性表面活性剂、非离子性表面活性剂、阳离子性表面活性剂、两性表面活性剂等，这之中优选阴离子性表面活性剂、非离子性表面活性剂。The above-mentioned surfactant is added in order to adjust ink characteristics such as surface tension. The surfactants that can be added for this purpose are not particularly limited, and various anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, etc. can be mentioned. Among them, anionic surfactants are preferred. Agent, non-ionic surfactant.
作为阴离子性表面活性剂，可列举例如烷基苯磺酸盐、烷基苯基磺酸盐、烷基萘磺酸盐、高级脂肪酸盐、高级脂肪酸酯的硫酸酯盐、高级脂肪酸酯的磺酸盐、高级醇醚的硫酸酯盐和磺酸盐、高级烷基磺基琥珀酸盐、聚氧乙烯烷基醚羧酸盐、聚氧乙烯烷基醚硫酸盐、烷基磷酸盐、聚氧乙烯烷基醚磷酸盐等，作为它们的具体例，可列举十二烷基苯磺酸盐、异丙基萘磺酸盐、一丁基苯基苯酚一磺酸盐、一丁基联苯磺酸盐、二丁基苯基苯酚二磺酸盐等。Examples of anionic surfactants include alkylbenzene sulfonates, alkylphenyl sulfonates, alkylnaphthalene sulfonates, higher fatty acid salts, sulfate ester salts of higher fatty acid esters, and higher fatty acid esters. Sulfonates, sulfates and sulfonates of higher alcohol ethers, higher alkyl sulfosuccinates, polyoxyethylene alkyl ether carboxylates, polyoxyethylene alkyl ether sulfates, alkyl phosphates, Polyoxyethylene alkyl ether phosphate, etc., as their specific examples, can cite dodecylbenzene sulfonate, isopropyl naphthalene sulfonate, monobutylphenylphenol monosulfonate, monobutyl bisulfonate Benzene sulfonate, dibutyl phenyl phenol disulfonate, etc.
作为非离子性表面活性剂，可列举例如聚氧乙烯烷基醚、聚氧乙烯烷基 苯基醚、聚氧乙烯脂肪酸酯、失水山梨糖醇脂肪酸酯、聚氧乙烯失水山梨糖醇脂肪酸酯、聚氧乙烯山梨糖醇脂肪酸酯、甘油脂肪酸酯、聚氧乙烯甘油脂肪酸酯、聚甘油脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯烷基胺、聚氧乙烯脂肪酸酰胺、脂肪酸炔醇酰胺、烷基烷醇酰胺、乙炔二醇、乙炔二醇的氧化乙烯加成物、聚乙二醇-聚丙二醇嵌段共聚物等，这些之中，优选聚氧乙烯壬基苯基醚、聚氧乙烯辛基苯基醚、聚氧乙烯十二烷基苯基醚、聚氧乙烯烷基醚、聚氧乙烯脂肪酸酯、失水山梨糖醇脂肪酸酯、聚氧乙烯失水山梨糖醇脂肪酸酯、脂肪酸炔醇酰胺、乙炔二醇、乙炔二醇的氧化乙烯加成物、聚乙二醇-聚丙二醇嵌段共聚物。Examples of nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan Alcohol fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkylamine, polyoxyethylene fatty acid Amides, fatty acid alkynolamides, alkyl alkanolamides, acetylene glycol, ethylene oxide adducts of acetylene glycol, polyethylene glycol-polypropylene glycol block copolymers, etc. Among these, polyoxyethylene nonyl is preferred Phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene dodecyl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene Sorbitan fatty acid ester, fatty acid alkynolamide, acetylene glycol, ethylene oxide adduct of acetylene glycol, polyethylene glycol-polypropylene glycol block copolymer.
作为其他的表面活性剂，还可以使用聚硅氧烷氧化乙烯加成物那样的聚硅氧烷系表面活性剂；全氟烷基羧酸盐、全氟烷基磺酸盐、氧化乙烯全氟烷基醚那样的氟系表面活性剂；刺孢青霉酸、鼠李糖脂、溶血卵磷脂那样的生物表面活性剂等。As other surfactants, polysiloxane-based surfactants such as polysiloxane ethylene oxide adducts can also be used; perfluoroalkyl carboxylate, perfluoroalkyl sulfonate, ethylene oxide perfluoro Fluorine-based surfactants such as alkyl ethers; biosurfactants such as echinosporic acid, rhamnolipids, lysolecithin, etc.
这些表面活性剂可以单独使用，也可以混合使用2种以上。添加表面活性剂的情况下，其添加量相对于油墨的总质量优选为0.001～2质量％的范围，更优选为0.001～1.5质量％，进一步优选为0.01～1质量％的范围。These surfactants may be used singly, or two or more of them may be mixed and used. When a surfactant is added, the addition amount is preferably in the range of 0.001 to 2% by mass relative to the total mass of the ink, more preferably in the range of 0.001 to 1.5% by mass, and still more preferably in the range of 0.01 to 1% by mass.
另外，根据需要，可以进一步添加防腐剂、粘度调整剂、pH调整剂、螯合剂、增塑剂、抗氧化剂、紫外线吸收剂等作为添加剂。In addition, as needed, preservatives, viscosity modifiers, pH modifiers, chelating agents, plasticizers, antioxidants, ultraviolet absorbers, etc. can be further added as additives.
本发明的印刷油墨可以通过将二
嗪颜料组合物、以及粘合剂树脂和添加剂分散于溶剂中来制造。作为分散所使用的分散机，可列举分散器、均质混合机、油漆调节机、Scandex混合器、珠磨机、磨碎机、球磨机、双辊研磨机、三辊研磨机、加压捏合机等。关于印刷油墨中二
嗪颜料组合物的分散，按照成为利用这些分散机能够分散的粘度的方式，添加树脂、溶剂而进行分散。分散后的印刷油墨中固体成分例如为5～50％，进一步向其中加入溶剂并混合，从而制成印刷油墨而供使用。
The printing ink of the present invention can be The oxazine pigment composition, the binder resin, and the additives are dispersed in a solvent to be manufactured. As the disperser used for the dispersion, a disperser, a homomixer, a paint conditioner, a Scandex mixer, a bead mill, an attritor, a ball mill, a two-roll mill, a three-roll mill, and a pressure kneader can be mentioned. Wait. About Printing Ink C2 In the dispersion of the oxazine pigment composition, a resin and a solvent are added and dispersed so that the viscosity becomes dispersible by these dispersers. The solid content of the dispersed printing ink is, for example, 5 to 50%, and a solvent is further added and mixed to form a printing ink for use.
本发明的二
嗪颜料组合物作为印刷油墨特别有用，除此之外，还可以用于涂料、塑料着色、喷墨油墨、数码碳粉、化妆品、滤色器、书写用具等广泛的用途。
The second of the present invention The oxazine pigment composition is particularly useful as a printing ink. In addition, it can also be used for a wide range of applications such as paint, plastic coloring, inkjet ink, digital toner, cosmetics, color filters, writing utensils, and the like.
实施例Example
以下，使用实施例和比较例进一步详细说明本发明。以下的实施例和比较例中，在没有特别说明的情况下，“％”表示“质量％”。Hereinafter, the present invention will be described in further detail using examples and comparative examples. In the following Examples and Comparative Examples, "%" means "% by mass" unless otherwise specified.
通过以下方法制造中间体1后，使用中间体1，制造包含式(I)表示的二
嗪颜料和式(II)表示的颜料衍生物的二
嗪颜料组合物。需说明的是，本实施例的FD-MS测定(质量分析)如下进行：使由实施例1、2得到的颜料组合物或由比较例1得到的颜料的粉末5mg分散于1.0mL的四氢呋喃中，利用FD-MS测定装置JMS-T100GC(日本电子株式会社制)对其进行质量分析。
After the intermediate 1 is produced by the following method, the intermediate 1 is used to produce the two containing the formula (I): Two of the oxazine pigment and the pigment derivative represented by formula (II) Oxazine pigment composition. It should be noted that the FD-MS measurement (mass analysis) of this example was performed as follows: 5 mg of the pigment composition obtained in Examples 1 and 2 or the pigment powder obtained in Comparative Example 1 was dispersed in 1.0 mL of tetrahydrofuran The mass analysis was carried out using an FD-MS measuring device JMS-T100GC (manufactured by JEOL Ltd.).
(制造例1：中间体1的合成)(Production Example 1: Synthesis of Intermediate 1)
在1000mL的四口烧瓶中，加入42g的3-氨基-N-乙基咔唑、300mL的1,2-二氯苯，搅拌使其溶解。接下来，将温度提高至36℃，加入在200mL的1,2-二氯苯中混合溶解的28g的四氯苯醌和21g的三乙胺，在36℃搅拌4小时。反应结束后，过滤反应液，用200mL的1,2-二氯苯和5L的60℃温水清洗过滤物。用100℃的送风干燥机使所得的过滤物干燥17小时，得到70.6g的中间体1。In a 1000 mL four-necked flask, 42 g of 3-amino-N-ethylcarbazole and 300 mL of 1,2-dichlorobenzene were added, and the mixture was stirred and dissolved. Next, the temperature was increased to 36°C, 28 g of tetrachlorobenzoquinone and 21 g of triethylamine which were mixed and dissolved in 200 mL of 1,2-dichlorobenzene were added, and the mixture was stirred at 36°C for 4 hours. After the reaction, the reaction solution was filtered, and the filtrate was washed with 200 mL of 1,2-dichlorobenzene and 5 L of 60°C warm water. The obtained filtrate was dried with an air dryer at 100°C for 17 hours to obtain 70.6 g of Intermediate 1.
[化11][化11]
(实施例1：二
嗪颜料组合物1的合成)
(Example 1: Two Synthesis of oxazine pigment composition 1)
首先，将由上述制造例1得到的5.9g中间体1投入至苯甲酸甲酯150ml，在80℃搅拌20分钟。接下来，加入TEMPO(关东化学株式会社制试剂)0.15g和氯化锌(关东化学株式会社制试剂)0.5g，在160℃搅拌16小时。冷却至100℃后，过滤所生成的固体，用苯甲酸甲酯30g、N-甲基-2-吡咯烷酮30g和水30g清洗。将所得的滤饼加热干燥，得到二
嗪颜料组合物1(3.1g、收获率53％)。对于二
嗪颜料组合物1，进行FD-MS测定(质量分析)，结果 检测到m/z 536和570的峰。由此可知，二
嗪颜料组合物1在包含C.I.颜料紫23的同时，还包含以下的颜料衍生物1(标称质量：570)和颜料衍生物2(标称质量：536)。
First, 5.9 g of Intermediate 1 obtained in the above-mentioned Production Example 1 was poured into 150 ml of methyl benzoate, and stirred at 80°C for 20 minutes. Next, 0.15 g of TEMPO (Kanto Chemical Co., Ltd. reagent) and 0.5 g of zinc chloride (Kanto Chemical Co., Ltd. reagent) were added, and the mixture was stirred at 160°C for 16 hours. After cooling to 100°C, the generated solid was filtered, and washed with 30 g of methyl benzoate, 30 g of N-methyl-2-pyrrolidone, and 30 g of water. The resulting filter cake is heated and dried to obtain two Triazine pigment composition 1 (3.1 g, yield 53%). For two The oxazine pigment composition 1 was subjected to FD-MS measurement (mass analysis), and as a result, peaks of m/z 536 and 570 were detected. It can be seen that two In addition to CI Pigment Violet 23, the oxazine pigment composition 1 also contains the following pigment derivatives 1 (nominal mass: 570) and pigment derivatives 2 (nominal mass: 536).
[化12][化12]
[化13][化13]
(实施例2：二
嗪颜料组合物2的合成)
(Example 2: Two (Synthesis of oxazine pigment composition 2)
首先，将由上述制造例1得到的5.9g中间体1投入至1,2-二氯苯150ml，在80℃搅拌20分钟。接下来，加入TEMPO(关东化学株式会社制试剂)0.15g和氯化锌(关东化学株式会社制试剂)0.5g，在160℃搅拌16小时。冷却至100℃后，过滤所生成的固体，用苯甲酸甲酯30g、N-甲基-2-吡咯烷酮30g和水30g清洗。将所得的滤饼加热干燥，得到二
嗪颜料组合物2(2.7g、收获率46％)。对于二
嗪颜料组合物1，进行FD-MS测定(质量分析)，结果检测到m/z 536和570的峰。由此可知，二
嗪颜料组合物2与实施例1同样地在包含C.I.颜料紫23的同时还包含颜料衍生物1(标称质量：570)和颜料衍生物2(标称质量：536)。
First, 5.9 g of Intermediate 1 obtained in the above-mentioned Production Example 1 was put into 150 ml of 1,2-dichlorobenzene, and stirred at 80°C for 20 minutes. Next, 0.15 g of TEMPO (Kanto Chemical Co., Ltd. reagent) and 0.5 g of zinc chloride (Kanto Chemical Co., Ltd. reagent) were added, and the mixture was stirred at 160°C for 16 hours. After cooling to 100°C, the generated solid was filtered, and washed with 30 g of methyl benzoate, 30 g of N-methyl-2-pyrrolidone, and 30 g of water. The resulting filter cake is heated and dried to obtain two Oxazine pigment composition 2 (2.7 g, yield 46%). For two The oxazine pigment composition 1 was subjected to FD-MS measurement (mass analysis), and as a result, peaks of m/z 536 and 570 were detected. It can be seen that two As in Example 1, the oxazine pigment composition 2 contains CI Pigment Violet 23 and also contains pigment derivative 1 (nominal mass: 570) and pigment derivative 2 (nominal mass: 536).
(比较例1：二
嗪颜料的合成)
(Comparative Example 1: Two (Synthesis of oxazine pigments)
参照日本特开2004-189668号公报第[0067]段来合成C.I.颜料紫23。对于该二
嗪颜料，进行FD-MS测定(质量分析)，结果没有检测到m/z 536和570的峰。由此可知，比较例1的合成方法中，不含颜料衍生物。另外，检测到m/z 628、634、662的峰。推测这些分子量的峰为下述含硫元素的杂质。由此可知，比较例1的合成方法中含有含硫元素的杂质。
The CI Pigment Violet 23 was synthesized with reference to paragraph [0067] of JP 2004-189668 A. For the two The oxazine pigment was subjected to FD-MS measurement (mass analysis), and as a result, no peaks of m/z 536 and 570 were detected. From this, it can be seen that the synthesis method of Comparative Example 1 does not contain a pigment derivative. In addition, peaks of m/z 628, 634, and 662 were detected. It is estimated that these molecular weight peaks are impurities containing sulfur elements described below. From this, it can be seen that the synthesis method of Comparative Example 1 contains sulfur-containing impurities.
[化14][化14]
[分散性和分散稳定性的评价][Evaluation of Dispersibility and Dispersion Stability]
对于由实施例1和2所得的二
嗪颜料组合物、由比较例1所得的二
嗪颜料，进行分散性和分散稳定性的评价。将颜料组合物或颜料的粉末大约10mg作为分散介质投入至装有5ml水的10mL玻璃瓶中，为了使其分散而施加超声波。
For the two obtained from Examples 1 and 2 Oxazine pigment composition, the two obtained from Comparative Example 1 For oxazine pigments, the dispersibility and dispersion stability are evaluated. About 10 mg of the pigment composition or the powder of the pigment was put into a 10 mL glass bottle containing 5 ml of water as a dispersion medium, and ultrasonic waves were applied to disperse it.
在刚刚施加超音波后(0h)对分散性进行评价，在18h后和72h后对分散稳定性进行评价。评价基准如下所示。The dispersibility was evaluated immediately after the ultrasonic wave was applied (0h), and the dispersion stability was evaluated after 18h and 72h. The evaluation criteria are as follows.
<评价基准><Evaluation criteria>
1：分离为无色透明的液体和紫色固体的沉淀物。1: Separated into a colorless and transparent liquid and a purple solid precipitate.
2：在淡紫色的液体中生成了紫色固体的沉淀物。2: A purple solid precipitate was formed in the lavender liquid.
3：在紫色的液体中生成了紫色固体的沉淀物。3: A purple solid precipitate was formed in the purple liquid.
4：在深紫色的液体中生成了紫色固体的沉淀物。4: A purple solid precipitate was formed in the dark purple liquid.
5：二
嗪颜料为完全分散的状态，没有看到紫色固体的沉淀物。
5: two The oxazine pigment was in a completely dispersed state, and no purple solid precipitate was seen.
[表1][Table 1]
| To | 分散性(0h)Dispersibility (0h) | 分散稳定性(18h)Dispersion stability (18h) | 分散稳定性(72h)Dispersion stability (72h) |
| 实施例1Example 1 | 55 | 44 | 44 |
| 实施例2Example 2 | 55 | 44 | 22 |
| 比较例1Comparative example 1 | 22 | 11 | 11 |
由表1可知，同时包含C.I.颜料紫23和颜料衍生物的实施例1和2的二
嗪颜料组合物与不含颜料衍生物的比较例1相比，分散性和分散稳定性更好。另外，实施例1和2的二
嗪颜料组合物中，没有观测到在比较例1中观测到的含硫元素的杂质。
It can be seen from Table 1 that the two of Examples 1 and 2 which contain both CI Pigment Violet 23 and pigment derivatives Compared with Comparative Example 1 containing no pigment derivative, the oxazine pigment composition has better dispersibility and dispersion stability. In addition, the second of Examples 1 and 2 In the oxazine pigment composition, the sulfur element-containing impurities observed in Comparative Example 1 were not observed.
Claims (7)
- 一种二嗪颜料组合物，其包含下述式(I)表示的二
嗪颜料和下述式(II)表示的颜料衍生物， One kind of two
An oxazine pigment composition comprising two represented by the following formula (I)Oxazine pigment and a pigment derivative represented by the following formula (II),
式(I)中的R 1和R 2分别独立地表示氢原子或卤原子，R 3和R 4分别独立地表示氢原子、碳数1～8的烷基、或苯基， R 1 and R 2 in the formula (I) each independently represent a hydrogen atom or a halogen atom, R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group,
式(II)中的R 5表示氢原子或卤原子，R 6和R 7分别独立地表示氢原子、碳数1～8的烷基、或苯基。 R 5 in formula (II) represents a hydrogen atom or a halogen atom, and R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group. - 根据权利要求1所述的二嗪颜料组合物，相对于式(I)表示的二
嗪颜料100质量份，包含0.3～10.0质量份的式(II)表示的颜料衍生物。 Two according to claim 1
Oxazine pigment composition, relative to the two represented by formula (I)100 parts by mass of the oxazine pigment contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II). - 一种印刷油墨，其含有权利要求1或2所述的二嗪颜料组合物。 A printing ink, which contains the two described in claim 1 or 2
Oxazine pigment composition. - 一种二嗪颜料组合物的制造方法，通过使下述式(III)表示的化合物与下述式(IV)表示的化合物在2～4价的金属盐的存在下在溶剂中发生环化反应，从而得到包含下述式(I)表示的二
嗪颜料和下述式(II)表示的颜料衍生物的二
嗪颜料组合物， One kind of two
The method for producing the oxazine pigment composition is obtained by causing a compound represented by the following formula (III) and a compound represented by the following formula (IV) to undergo a cyclization reaction in a solvent in the presence of a 2- to 4-valent metal salt. Contains two represented by the following formula (I)Two of the oxazine pigment and the pigment derivative represented by the following formula (II)Oxazine pigment composition,
式(III)中的R 1和R 2分别独立地表示氢原子或卤原子，R 3和R 4分别独立地表示氢原子、碳数1～8的烷基、或苯基， R 1 and R 2 in the formula (III) each independently represent a hydrogen atom or a halogen atom, R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group,
式(IV)中的R 8表示氢原子、羟基、碳数1～4的烷氧基或甲硅烷氧基， R 8 in the formula (IV) represents a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms or a siloxy group,
式(I)中的R 1和R 2分别独立地表示氢原子或卤原子，R 3和R 4分别独立地表示氢原子、碳数1～8的烷基、或苯基， R 1 and R 2 in the formula (I) each independently represent a hydrogen atom or a halogen atom, R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group,
式(II)中的R 5表示氢原子或卤原子，R 6和R 7分别独立地表示氢原子、碳数1～8的烷基、或苯基。 R 5 in formula (II) represents a hydrogen atom or a halogen atom, and R 6 and R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group. - 根据权利要求4所述的二嗪颜料组合物的制造方法，相对于式(III)表示的化合物1摩尔，使用0.01～0.3摩尔的式(IV)表示的化合物，并且使用0.05～1.0摩尔的2～4价的金属盐。 According to claim 4
The method for producing the oxazine pigment composition uses 0.01 to 0.3 moles of the compound represented by the formula (IV) and 0.05 to 1.0 moles of the tetravalent metal salt relative to 1 mole of the compound represented by the formula (III). - 根据权利要求4或5所述的二嗪颜料组合物的制造方法，所述溶剂为苯甲酸甲酯、1,2-二氯苯、N-甲基吡咯烷酮、3-甲氧基丁醇或二甲基亚砜。 The two according to claim 4 or 5
In the manufacturing method of the oxazine pigment composition, the solvent is methyl benzoate, 1,2-dichlorobenzene, N-methylpyrrolidone, 3-methoxybutanol or dimethyl sulfoxide. - 根据权利要求4～6中任一项所述的二嗪颜料组合物的制造方法，相对于式(I)表示的二
嗪颜料100质量份，包含0.3～10.0质量份的式(II)表示的颜料衍生物。 The two according to any one of claims 4 to 6
The manufacturing method of the oxazine pigment composition, relative to the two represented by the formula (I)100 parts by mass of the oxazine pigment contains 0.3 to 10.0 parts by mass of the pigment derivative represented by formula (II).
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117624934A (en) * | 2023-11-22 | 2024-03-01 | 中广核拓普（湖北）新材料有限公司 | Preparation method of pigment violet 23 for engineering plastics |
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| Publication number | Publication date |
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| JP7276615B2 (en) | 2023-05-18 |
| CN115038758A (en) | 2022-09-09 |
| JP2022549530A (en) | 2022-11-25 |
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