JPWO2007058209A1 - Disperse dye, disperse dye composition, ink for ink-jet printing, dyeing method and dyed material using these - Google Patents
Disperse dye, disperse dye composition, ink for ink-jet printing, dyeing method and dyed material using these Download PDFInfo
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- JPWO2007058209A1 JPWO2007058209A1 JP2007511144A JP2007511144A JPWO2007058209A1 JP WO2007058209 A1 JPWO2007058209 A1 JP WO2007058209A1 JP 2007511144 A JP2007511144 A JP 2007511144A JP 2007511144 A JP2007511144 A JP 2007511144A JP WO2007058209 A1 JPWO2007058209 A1 JP WO2007058209A1
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- Prior art keywords
- dye
- formula
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- orange
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 217
- 239000000203 mixture Substances 0.000 title claims abstract description 177
- 238000004043 dyeing Methods 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000007641 inkjet printing Methods 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 title description 5
- 239000000975 dye Substances 0.000 claims abstract description 483
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
- 239000002657 fibrous material Substances 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 11
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims description 35
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 18
- 239000001043 yellow dye Substances 0.000 claims description 18
- 239000001045 blue dye Substances 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 17
- 239000001044 red dye Substances 0.000 claims description 17
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000004753 textile Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 abstract description 58
- 229920000728 polyester Polymers 0.000 abstract description 23
- 238000000859 sublimation Methods 0.000 abstract description 22
- 230000008022 sublimation Effects 0.000 abstract description 22
- 239000000835 fiber Substances 0.000 abstract description 20
- 239000000126 substance Substances 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 91
- 238000002360 preparation method Methods 0.000 description 63
- 238000009472 formulation Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- -1 for example Substances 0.000 description 23
- 239000004744 fabric Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000002270 dispersing agent Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
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- 125000000217 alkyl group Chemical group 0.000 description 14
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- 239000000654 additive Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
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- 229920002994 synthetic fiber Polymers 0.000 description 8
- 239000012209 synthetic fiber Substances 0.000 description 8
- 238000010998 test method Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000008049 diazo compounds Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229910052724 xenon Inorganic materials 0.000 description 6
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 5
- UJTRMFNKHYGXDI-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)anilino]ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(CCC#N)C1=CC=CC=C1 UJTRMFNKHYGXDI-UHFFFAOYSA-N 0.000 description 4
- 0 COc(c(N)c1C(c2c3cccc2)=O)cc(*c2ccccc2)c1C3=O Chemical compound COc(c(N)c1C(c2c3cccc2)=O)cc(*c2ccccc2)c1C3=O 0.000 description 4
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- 125000000129 anionic group Chemical group 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000001048 orange dye Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MFJODFSUXHFZJR-UHFFFAOYSA-N 2-chloro-4-nitro-6-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C(F)(F)F MFJODFSUXHFZJR-UHFFFAOYSA-N 0.000 description 3
- AEMNOPYAEDEKIP-UHFFFAOYSA-N 3-[n-[2-(2-cyanoethoxy)ethyl]anilino]propanenitrile Chemical compound N#CCCOCCN(CCC#N)C1=CC=CC=C1 AEMNOPYAEDEKIP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VTSOQYVBDQONBG-UHFFFAOYSA-N 2-bromo-4-nitro-6-(trifluoromethyl)aniline Chemical group NC1=C(Br)C=C([N+]([O-])=O)C=C1C(F)(F)F VTSOQYVBDQONBG-UHFFFAOYSA-N 0.000 description 2
- YWTREMGUPSFSBA-UHFFFAOYSA-N 3-[N-(2-butoxyethyl)anilino]propanenitrile Chemical compound CCCCOCCN(CCC#N)C1=CC=CC=C1 YWTREMGUPSFSBA-UHFFFAOYSA-N 0.000 description 2
- WZJJWQVBLSPALW-UHFFFAOYSA-N 3-[n-(2-hydroxyethyl)anilino]propanenitrile Chemical compound N#CCCN(CCO)C1=CC=CC=C1 WZJJWQVBLSPALW-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
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- 230000000740 bleeding effect Effects 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
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- 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
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
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- 239000000417 fungicide Substances 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
- C09B29/0826—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene/-alkynylene-O)(-alkenylene/-alkynylene-CN)
-
- 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
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Abstract
疎水性繊維材料の染色性に優れ、高耐光堅牢度を有し昇華堅牢度にも優れ良好なビルドアップ性を兼ね備えた、特に自動車内装用シートに使用される染料として有用である新規な橙色分散染料及びそれを使用した黄色〜橙色、茶色、紺色、黒色用分散染料組成物、インクジェット捺染用インク、これらを用いた染色方法及び染色物を提供する。本発明の橙色分散染料は下記（化１）［式中、Ｘ１は塩素原子又は臭素原子を表し、Ｒ１はベンゾイル基、シアノエチル基、Ｃ１〜Ｃ４アルキル基、フェニル基又はＣ１〜Ｃ４アルキルで１以上置換されたフェニル基を表す。］で表され、ポリエステル等の疎水性繊維を橙色に染色できる。A novel orange dispersion that is particularly useful as a dye for automotive interior seats, with excellent dyeability of hydrophobic fiber materials, high light fastness and excellent sublimation fastness, and good build-up properties Disclosed are a dye, a yellow-orange, brown, amber, black disperse dye composition using the same, an ink for inkjet printing, a dyeing method using the same, and a dyed product. The orange disperse dye of the present invention is represented by the following (Chemical Formula 1): wherein X1 represents a chlorine atom or a bromine atom, and R1 is a benzoyl group, a cyanoethyl group, a C1-C4 alkyl group, a phenyl group, or a C1-C4 alkyl. Represents a substituted phenyl group. ], And hydrophobic fibers such as polyester can be dyed orange.
Description
本発明は、疎水性繊維材料の染色性に優れ、高耐光堅牢度を有し昇華堅牢度にも優れ良好なビルドアップ性を兼ね備えた、特に自動車内装用シートとして有用である新規な橙色分散染料、分散染料組成物、インクジェット捺染用インク、これを用いた染色方法及び染色物に関するものである。 The present invention is a novel orange disperse dye which is particularly useful as a sheet for automobile interiors, which is excellent in dyeability of hydrophobic fiber materials, has high light fastness and excellent sublimation fastness, and also has good build-up property. The present invention relates to a disperse dye composition, an ink for inkjet printing, a dyeing method using the ink, and a dyed product.
近年、自動車内装用、特に座席シートの材質として疎水性繊維材料が使用されてきており、特にポリエステル系繊維が多く使用されている。また近年ファッション性の向上により豊かな色彩が要求されるようになった。しかし自動車内装用シートの場合、高温長時間の露光によって、黄色が変褪色を起こし、赤色及び青色との混合染色物の変色の原因にもなっている。 In recent years, hydrophobic fiber materials have been used as materials for automobile interiors, particularly seat seats, and in particular, polyester fibers are often used. In recent years, richer colors have come to be demanded by improving fashionability. However, in the case of a car interior sheet, yellow is discolored by exposure at high temperature for a long time, which causes discoloration of a mixed dyed product of red and blue.
通常の耐光性の評価方法としてはＪＩＳ Ｌ ０８４２に準じた試験方法があるが、自動車内装用シートに使用される染料の耐光性の評価方法として、より過酷な試験方法であるキセノンアーク灯を用いる加速試験法（例えばトヨタ法）がある。この試験方法を用いると、耐光性の劣る染料は良好な染料と比較して通常の試験方法の場合より顕著に差が出る。 There is a test method according to JIS L 0842 as a normal light resistance evaluation method, but a more severe test method, a xenon arc lamp, is used as a light resistance evaluation method for dyes used in automobile interior seats. There is an accelerated test method (for example, Toyota method). When this test method is used, a dye having poor light resistance is significantly different from a normal test method in comparison with a good dye.
高温長時間の露光によって黄色が変褪色を起こす現象の対策として、例えば下記特許文献１、下記特許文献２、下記特許文献３などに高耐光性黄色分散染料組成物が提案されている。 As countermeasures against the phenomenon in which yellow is discolored by high-temperature and long-time exposure, for example, Patent Document 1, Patent Document 2, Patent Document 3, and the like have proposed highly light-resistant yellow disperse dye compositions.
しかし、前記特許文献１〜３に記載の黄色分散染料組成物を赤色及び青色との配合成分として使用して、茶色、紺色又は黒色の染色物を得ようとした場合、高耐光堅牢度を有してはいるものの、ビルドアップ性に劣るという問題がある。 However, when the yellow disperse dye composition described in Patent Documents 1 to 3 is used as a blending component with red and blue to obtain a brown, amber or black dyed product, it has high light fastness. However, there is a problem that it is inferior in build-up property.
このため、茶色、紺色又は黒色用分散染料の配合成分には橙色系染料が使用されている。従来の橙色系染料としては、例えば、下記式（１）の染料や下記式（２）の染料等が一般的に広く使用されている。
しかし、上記橙色系染料は自動車内装用シートの染料として使用するには耐光性が十分ではなく、高耐光性の分散染料との調色用途として使用できなかった。 However, the above-mentioned orange dyes are not sufficiently light-resistant to be used as dyes for automobile interior sheets and cannot be used for toning with highly light-resistant disperse dyes.
また、耐光性がよいとされる橙色系染料としては、特許文献４の実施例１に記載の下記式（３）の染料及び特許文献５には下記式（４）の染料が提案されている。
しかし、前記式（３）の染料は、耐光性は非常に優秀であるが、昇華堅牢度がよくはなく、ビルドアップ性にも難がある。また、前記式（４）の染料は、ビルドアップ性は非常に優秀であるが、昇華堅牢度がよくはなく、自動車内装用シートの染料として使用するには耐光性が十分ではない。
本発明は前記従来の問題を解決するため、疎水性繊維材料の染色性に優れ、高耐光堅牢度を有し昇華堅牢度にも優れ良好なビルドアップ性を兼ね備えた、特に自動車内装用シートに使用される染料として有用である新規な橙色分散染料及びそれを使用した黄色から橙色、茶色、紺色、黒色用分散染料組成物、インクジェット捺染用インク、これらを用いた染色方法及び染色物を提供することを課題とする。 In order to solve the above-mentioned conventional problems, the present invention is excellent in dyeing properties of hydrophobic fiber materials, has high light fastness and excellent sublimation fastness, and has a good build-up property. Disclosed are a novel orange disperse dye useful as a dye to be used, a yellow to orange, brown, amber, black disperse dye composition using the same, an ink for inkjet printing, a dyeing method using the same, and a dyed product. This is the issue.
本発明の橙色分散染料は、下記式［１］
［前記式［１］中、Ｘ１は塩素原子又は臭素原子を表し、Ｒ１はベンゾイル基、シアノエチル基、Ｃ１〜Ｃ４アルキル基、フェニル基又はＣ１〜Ｃ４アルキルで１以上置換されたフェニル基を表す。］
で示され、橙色分散染料であることを特徴とする。[In the formula [1], X 1 represents a chlorine atom or a bromine atom, and R 1 is substituted with one or more of a benzoyl group, a cyanoethyl group, a C 1 -C 4 alkyl group, a phenyl group, or a C 1 -C 4 alkyl. Represents a phenyl group. ]
And is characterized by being an orange disperse dye.
また、本発明の黄色から橙色系分散染料組成物（以下、「第１の分散染料組成物」と呼ぶ）は、前記式［１］で表される橙色分散染料と、下記式［２］で表される染料、下記式［３］で表される染料、下記式［４］で表される染料、下記式［５］で表される染料、及び下記式［６］で表される染料から選ばれる少なくとも一種の黄色系染料とを含むことを特徴とする。
［前記式［４］中、Ｘ２は水素原子又は臭素原子を表し、Ｒ２は水素原子又は−ＣＯＯＣ２Ｈ４ＯＣ２Ｈ５基を表す。］
［前記式［６］中、Ｒ３はＣ１〜Ｃ４アルキル基、フェニル基又はＣ１〜Ｃ４アルキルで１以上置換されたフェニル基を表す。］[In the above formula [6], R 3 represents a C 1 -C 4 alkyl group, a phenyl group, or a phenyl group substituted with one or more C 1 -C 4 alkyl. ]
また、本発明の分散染料組成物（以下、「第２の分散染料組成物」と呼ぶ）は、前記式［１］で表される橙色分散染料と、下記式［１７］で表される染料とを含むことを特徴とする。
また、本発明の分散染料組成物（以下、「第３の分散染料組成物」と呼ぶ）は、前記式［１］で表される橙色分散染料又は前記黄色から橙色系分散染料組成物の１種である第１の配合用橙色系分散染料組成物と、下記式［７］で表される染料、下記式［８］で表される染料、下記式［９］で表される染料、下記式［１０］で表される染料、及び下記式［１１］の染料から選ばれる少なくとも１種の赤色系染料と、下記式［１２］で表される染料、下記式［１３］で表される染料、下記式［１４］で表される染料、下記式［１５］で表される染料、及び下記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料とを含むことを特徴とする。
［前記式［８］中、Ｒ４は水素原子、−ＯＣＨ３基、−ＯＣ２Ｈ５基又は−ＳＯ２ＮＨＣ３Ｈ６ＯＣ２Ｈ５を表す。］
［前記式［１０］中、Ｒ５はフェニル基、Ｃ１〜Ｃ４アルキルで１以上置換されたフェニル基、−ＣＯＯＣ２Ｈ５基又は−ＣＯＯＣ６Ｈ５基を表す。］
［前記式［１１］中、Ｒ６は水素原子、−ＣＨ３基又は−Ｃ２Ｈ５基を表す。］
［前記式［１３］中、Ｒ７は−Ｃ３Ｈ６ＯＣＨ３基又は−Ｃ３Ｈ６ＯＣ２Ｈ４ＯＣＨ３基を表す。］
［前記式［１５］中、Ｒ８はヒドロキシル基、−ＯＣＨ３基又は−ＯＣ２Ｈ５基を表す。］
［前記式［１６］中、Ｘ３は水素原子又は臭素原子を表す。］[In the formula [16], X 3 represents a hydrogen atom or a bromine atom. ]
なお、前記第１の配合用橙色系分散染料組成物は、前記黄色から橙色系の第１の分散染料組成物において、前記橙色分散染料を６５〜９８重量％及び前記黄色系染料を２〜３５重量％含み、橙色系であり、配合用であるものを意味する。 The first orange disperse dye composition for blending in the yellow to orange first disperse dye composition is 65 to 98% by weight of the orange disperse dye and 2 to 35 of the yellow dye. It means that it contains orange and is orange and is for compounding.
また、本発明の分散染料組成物（以下、「第４の分散染料組成物」と呼ぶ）は、前記第２の分散染料組成物の１種である第２の配合用橙色系分散染料組成物と、下記式［７］で表される染料、下記式［８］で表される染料、下記式［９］で表される染料、下記式［１０］で表される染料、及び下記式［１１］の染料から選ばれる少なくとも１種の赤色系染料と、下記式［１２］で表される染料、下記式［１３］で表される染料、下記式［１４］で表される染料、下記式［１５］で表される染料、及び下記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料とを含むことを特徴とする。なお、前記第２の配合用橙色系分散染料組成物は、前記第２の分散染料組成物において、前記橙色分散染料を２０〜８０重量％及び前記式［１７］で表される染料を２０〜８０重量％含み、橙色系であり、配合用であるものを意味する。 Also, the disperse dye composition of the present invention (hereinafter referred to as “fourth disperse dye composition”) is a second disperse orange disperse dye composition which is one of the second disperse dye compositions. And a dye represented by the following formula [7], a dye represented by the following formula [8], a dye represented by the following formula [9], a dye represented by the following formula [10], and the following formula [ 11], a dye represented by the following formula [12], a dye represented by the following formula [13], a dye represented by the following formula [14], It includes at least one blue dye selected from a dye represented by the formula [15] and a dye represented by the following formula [16]. The second disperse orange-based disperse dye composition in the second disperse dye composition is 20 to 80% by weight of the orange disperse dye and 20 to 20% of the dye represented by the formula [17]. It means 80% by weight, orange color and for compounding.
本発明の疎水性繊維材料の染色方法は、前記橙色分散染料、前記第１から第４の分散染料組成物又は前記第１もしくは第２の配合用橙色系分散染料組成物を用いることを特徴とする。 The method for dyeing a hydrophobic fiber material of the present invention is characterized by using the orange disperse dye, the first to fourth disperse dye compositions, or the first or second blending orange disperse dye composition. To do.
本発明のインクジェット捺染用インクは、前記橙色分散染料、前記第１から第４の分散染料組成物又は前記第１もしくは第２の配合用橙色系分散染料組成物を含有することを特徴とする。 The ink for inkjet textile printing of the present invention is characterized by containing the orange disperse dye, the first to fourth disperse dye compositions, or the first or second orange disperse dye composition.
本発明の橙色分散染料、分散染料組成物、及びインクジェット捺染用インクは、疎水性繊維材料の染色において、ビルドアップ性等の染色性に優れ、昇華堅牢度にも優れ、特に高耐光堅牢度を要求される自動車内装用シートの染色にも適する。また、これらを用いた染色方法及び染色物も提供することができる。 The orange disperse dye, the disperse dye composition, and the ink for inkjet printing of the present invention are excellent in dyeing properties such as build-up property, dyeing of hydrophobic fiber materials, excellent in sublimation fastness, particularly high light fastness. It is also suitable for dyeing required automotive interior sheets. Moreover, the dyeing | staining method and dyeing | staining thing using these can also be provided.
本発明の橙色分散染料は、前記のように、前記式［１］で表される橙色分散染料である。
［前記式［１］中、Ｘ１は塩素原子又は臭素原子を表し、Ｒ１はベンゾイル基、シアノエチル基、Ｃ１〜Ｃ４アルキル基、フェニル基又はＣ１〜Ｃ４アルキルで１以上置換されたフェニル基を表す。］[In the formula [1], X 1 represents a chlorine atom or a bromine atom, and R 1 is substituted with one or more of a benzoyl group, a cyanoethyl group, a C 1 -C 4 alkyl group, a phenyl group, or a C 1 -C 4 alkyl. Represents a phenyl group. ]
本明細書において、前記Ｃ１〜Ｃ４アルキル基とは、炭素数１〜４の直鎖状又は分岐状アルキル基を意味し、例えば、メチル、エチル、プロピル、イソプロピル、ｎ−ブチル、ｓｅｃ−ブチル、ｔｅｒｔ−ブチル等が挙げられる。前記Ｃ１〜Ｃ４アルキル基は、好ましくはｎ−ブチルである。In the present specification, the C 1 -C 4 alkyl group means a linear or branched alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec- Examples include butyl and tert-butyl. Wherein C 1 -C 4 alkyl group is preferably n- butyl.
また、前記Ｃ１〜Ｃ４アルキルで１以上置換されたフェニル基としては例えば、フェニル基に１〜５のＣ１〜Ｃ４アルキル基が置換されたものが挙げられる。前記フェニル基に２以上のＣ１〜Ｃ４アルキル基が置換される場合、前記アルキル基はそれぞれ異なっていても同一であってもよい。前記置換フェニル基としては、例えば、４−メチルフェニル、２，４−ジメチルフェニル、４−エチル、２，４，６−トリメチルフェニル等が挙げられる。As the phenyl group substituted by one or more in the C 1 -C 4 alkyl, such as, C 1 -C 4 alkyl groups of 1 to 5 phenyl groups are those substituted. If two or more C 1 -C 4 alkyl group on the phenyl group is substituted, the alkyl group may be the same or different. Examples of the substituted phenyl group include 4-methylphenyl, 2,4-dimethylphenyl, 4-ethyl, 2,4,6-trimethylphenyl, and the like.
前記式［１］で表される橙色分散染料としては、前記式［１］中、
Ｘ１が塩素原子を表し、Ｒ１がベンゾイル基を表すもの、
Ｘ１が塩素原子を表し、Ｒ１がシアノエチル基を表すもの、
Ｘ１が塩素原子を表し、Ｒ１がＣ１〜Ｃ４アルキル基を表すもの、
Ｘ１が塩素原子を表し、Ｒ１がフェニル基を表すもの、
Ｘ１が塩素原子を表し、Ｒ１がＣ１〜Ｃ４アルキル基で置換されたフェニル基を表すもの、
Ｘ１が臭素原子を表し、Ｒ１がベンゾイル基を表すもの、
Ｘ１が臭素原子を表し、Ｒ１がシアノエチル基を表すもの、
Ｘ１が臭素原子を表し、Ｒ１がＣ１〜Ｃ４アルキル基を表すもの、
Ｘ１が臭素原子を表し、Ｒ１がフェニル基を表すもの、及び
Ｘ１が臭素原子を表し、Ｒ１がＣ１〜Ｃ４アルキル基で置換されたフェニル基を表すものが挙げられる。As the orange disperse dye represented by the formula [1], in the formula [1],
X 1 represents a chlorine atom, R 1 represents a benzoyl group,
X 1 represents a chlorine atom, R 1 represents a cyanoethyl group,
X 1 represents a chlorine atom, R 1 represents a C 1 -C 4 alkyl group,
X 1 represents a chlorine atom, R 1 represents a phenyl group,
X 1 represents a chlorine atom, and R 1 represents a phenyl group substituted with a C 1 -C 4 alkyl group,
X 1 represents a bromine atom, R 1 represents a benzoyl group,
X 1 represents a bromine atom and R 1 represents a cyanoethyl group,
X 1 represents a bromine atom, R 1 represents a C 1 -C 4 alkyl group,
X 1 represents a bromine atom and R 1 represents a phenyl group, and X 1 represents a bromine atom, and an represents a phenyl group R 1 is substituted by C 1 -C 4 alkyl group.
前記式［１］で表される橙色分散染料としては、前記式［１］中、Ｘ１が塩素原子を表し、Ｒ１がベンゾイル基を表すもの、及び、Ｘ１が塩素原子を表し、Ｒ１がシアノエチル基を表すものが好ましく、前記式［１］中、Ｘ１が塩素原子を表し、Ｒ１がベンゾイル基を表すものがより好ましい。As the orange disperse dye represented by the formula [1], in the formula [1], X 1 represents a chlorine atom, R 1 represents a benzoyl group, and X 1 represents a chlorine atom. It is preferable that 1 represents a cyanoethyl group, and in the formula [1], it is more preferable that X 1 represents a chlorine atom and R 1 represents a benzoyl group.
本発明において、前記式［１］の好ましい具体例としては、前記式［１］中、Ｘ１が塩素原子を表し、Ｒ１がベンゾイル基を表すものとしては下記式［１−１］で表される染料、前記式［１］中、Ｘ１が臭素原子を表し、Ｒ１がシアノエチル基を表すものとしては下記式［１−２］で表される染料及び、前記式［１］中、Ｘ１が臭素原子を表し、Ｒ１がＣ４アルキル基を表すものとしては、下記式［１−３］で表される染料が挙げられる。
上記の染料のうち耐光性の観点から特に［１−１］の染料が好ましい。 Among the above dyes, the dye [1-1] is particularly preferable from the viewpoint of light resistance.
前記式［１］で表される橙色分散染料の製造方法について以下に説明する。まず、下記式［１００］の化合物を、鉱酸又は有機カルボン酸中において、場合により追加させた水の存在下でニトロソ化剤又はニトロシル硫酸を使用してジアゾ化してジアゾ化合物を得る。使用する有機カルボン酸としては、例えば酢酸及びプロピオン酸が挙げられる。また鉱酸としては例えば塩酸、リン酸及び硫酸、好ましくは硫酸が挙げられる。使用するニトロソ化剤としては、アルカリ金属の亜硝酸塩、例えば、固体状態若しくは水溶液状態の亜硝酸ナトリウムである。ジアゾ化温度は、好ましくは−５〜３０℃、さらに好ましくは０〜２０℃である。
［前記式［１００］中、Ｘ１は塩素原子又は臭素原子を表す。］[In the formula [100], X 1 represents a chlorine atom or a bromine atom. ]
カップラーとしての下記式［１０１］で表される化合物の溶液又は懸濁液に、得られたジアゾ化合物の溶液を、例えば０〜３５℃の温度範囲で添加して、前記式［１］で表される化合物を得る。最初に導入されるカップラー溶液又は懸濁液のｐＨは好ましくは弱酸性である。又は、カップラーとしての下記式［１０１］で表される化合物を酢酸のような弱酸の溶液に加えて溶解状態又は懸濁液状態にし、そこへジアゾ化合物の溶液を添加してもよい。この場合、酢酸ナトリウムなどの緩衝剤を添加することが有利な場合がある。
［前記式［１０１］中、Ｒ１はベンゾイル基、シアノエチル基、Ｃ１〜Ｃ４アルキル基、フェニル基又はＣ１〜Ｃ４アルキルで１以上置換されたフェニル基を表す。］[In the formula [101], R 1 represents a benzoyl group, a cyanoethyl group, a C 1 -C 4 alkyl group, a phenyl group, or a phenyl group substituted with one or more C 1 -C 4 alkyl. ]
なお、前記式［１］のジアゾ化合物の原料である下記式［１００］で表される化合物は、米国特許第３３４２８０４号明細書の染料（ＩＶ）のジアゾ成分として公知である。 In addition, the compound represented by the following formula [100], which is a raw material of the diazo compound of the formula [1], is known as a diazo component of the dye (IV) in US Pat. No. 3,342,804.
また、前記式［１０１］で表される化合物のうち、Ｒ１がベンゾイル基の場合は、例えばＣ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｏｒａｎｇｅ ７３のカップラーとして広く一般的に知られ使用されている。Further, among the compounds represented by the formula [101], when R 1 is a benzoyl group, for example, C.I. I. It is widely known and used as a coupler for Disperse Orange 73.
また、Ｒ１がシアノエチル基、ブチル基の式［１０１］で表される化合物も、広く一般的に知られ使用されている公知な化合物であり、既知の方法で合成することができる。A compound represented by the formula [101] wherein R 1 is a cyanoethyl group or a butyl group is also a known compound that is widely known and used, and can be synthesized by a known method.
本発明者らは、鋭意検討を重ねた結果、驚くべきことに、前記式［１］で表される染料が、疎水性繊維材料の染色性に優れ、高耐光堅牢度を有し、昇華堅牢度にも優れ良好なビルドアップ性を兼ね備えた、特に自動車内装用シート用染料として有用な橙色分散染料であることを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have surprisingly found that the dye represented by the formula [1] is excellent in dyeability of the hydrophobic fiber material, has high light fastness, and sublimation fastness. The present invention has been completed by discovering that it is an orange disperse dye that has excellent build-up properties and is particularly useful as a dye for automobile interior sheets.
前記式［１］で表される橙色分散染料は、単独での使用において、前記トヨタ法に基づく試験方法においても良好な耐光堅牢度を有しており、昇華堅牢度、ビルドアップ性のすべてにおいて優れている。 The orange disperse dye represented by the formula [1] has good light fastness even in the test method based on the Toyota method when used alone, and in all of sublimation fastness and build-up property. Are better.
したがって、他の高耐光性分散染料と配合することにより、黄色から橙色、茶色、紺色、黒色用分散染料組成物を提供することができる。 Therefore, by blending with other high light-resistant disperse dyes, disperse dye compositions for yellow to orange, brown, amber, and black can be provided.
以下に本発明の橙色分散染料を黄色系染料と配合した黄色から橙色系の第１の分散染料組成物について、説明する。 A yellow to orange first disperse dye composition obtained by blending the orange disperse dye of the present invention with a yellow dye will be described below.
本発明の橙色分散染料はやや赤みのため、黄色染料に少量混合しても赤みの黄色にすることができる。また、これらの配合割合を変えることにより、黄色から橙色系の様々な色相を得ることが可能となる。 Since the orange disperse dye of the present invention is slightly reddish, it can be reddish yellow even if mixed in a small amount with a yellow dye. In addition, by changing the blending ratio, various hues from yellow to orange can be obtained.
耐光性を維持するためには、配合に用いる黄色系染料も同様の堅牢性を兼ね備えていなければはならないため、前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、及び前記式［６］で表される黄色系染料を用いる。 In order to maintain light resistance, the yellow dye used in the blending must also have the same fastness. Therefore, the dye represented by the formula [2] and the dye represented by the formula [3] The dye represented by Formula [4], the dye represented by Formula [5], and the yellow dye represented by Formula [6] are used.
本発明の黄色から橙色系の第１の分散染料組成物のうち、黄色系分散染料組成物は、前記式［１］で示される橙色分散染料を３〜２０重量％及び前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、及び前記式［６］で表される染料から選ばれる少なくとも一種の黄色系染料を８０〜９７重量％含有するのが好ましい。さらに好適には、前記黄色系分散染料組成物は、前記橙色分散染料３〜１５重量％及び前記黄色系染料を８５〜９７重量％を含有する。 Among the yellow to orange first disperse dye compositions of the present invention, the yellow disperse dye composition comprises 3 to 20% by weight of the orange disperse dye represented by the formula [1] and the formula [2]. A dye represented by the formula [3], a dye represented by the formula [4], a dye represented by the formula [5], and a dye represented by the formula [6]. It is preferable to contain 80 to 97% by weight of at least one selected from yellowish dyes. More preferably, the yellow disperse dye composition contains 3 to 15% by weight of the orange disperse dye and 85 to 97% by weight of the yellow dye.
本発明の黄色から橙色系の第１の分散染料組成物のうち、橙色系分散染料組成物は、前記式［１］で表される橙色分散染料を２０〜９８重量％及び前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、及び前記式［６］で表される染料から選ばれる少なくとも一種の黄色系染料を２〜８０重量％含有するのが好ましい。より好適には前記橙色分散染料が２５〜８５重量％及び前記黄色系染料が１５〜７５重量％であり、さらに好適には、前記橙色分散染料が３０〜７０重量％及び前記黄色系染料が７０〜３０重量％である。 Among the yellow to orange first disperse dye compositions of the present invention, the orange disperse dye composition comprises 20 to 98% by weight of the orange disperse dye represented by the formula [1] and the formula [2]. The dye represented by formula [3], the dye represented by formula [4], the dye represented by formula [5], and the dye represented by formula [6] It is preferable to contain 2 to 80% by weight of at least one yellow dye selected from: More preferably, the orange disperse dye is 25 to 85% by weight and the yellow dye is 15 to 75% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight and the yellow dye is 70%. ~ 30% by weight.
また、前記式［１７］の染料も耐光性が良好な染料であり配合に用いることができる。前記式［１］で表される橙色分散染料と併用することにより、前記式［１７］の染料の欠点である昇華堅牢度及びビルドアップ性が改善される。従って、本発明の第２の分散染料組成物は、前記式［１］で表される橙色分散染料と、前記式［１７］で表される染料とを含むことを特徴とする。 The dye of the formula [17] is also a dye having good light resistance and can be used in the blending. By using together with the orange disperse dye represented by the formula [1], the sublimation fastness and build-up property, which are the disadvantages of the dye of the formula [17], are improved. Therefore, the second disperse dye composition of the present invention is characterized by including the orange disperse dye represented by the formula [1] and the dye represented by the formula [17].
本発明の橙色系の第２の分散染料組成物は、前記式［１］で示される橙色分散染料を２０〜９８重量％及び前記式［１７］の染料を２〜８０重量％含有するのが好ましい。より好適には前記橙色分散染料が２５〜８５重量％及び前記式［１７］の染料が１５〜７５重量％であり、さらに好適には、前記橙色分散染料が３０〜７０重量％及び前記式［１７］の染料が７０〜３０重量％である。 The orange-based second disperse dye composition of the present invention contains 20 to 98% by weight of the orange disperse dye represented by the formula [1] and 2 to 80% by weight of the dye of the formula [17]. preferable. More preferably, the orange disperse dye is 25 to 85% by weight and the dye of the formula [17] is 15 to 75% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight and the formula [17]. 17] is 70 to 30% by weight.
本発明の黄色から橙色系の第１の分散染料組成物のうち、配合用の橙色系分散染料組成物（以下、「第１の配合用橙色系分散染料組成物」と呼ぶ）は、他の赤色系染料及び青色系染料と配合して、茶色、紺色、黒色用分散染料組成物を作製するために使用されることができる。ビルドアップ性等の観点から、第１の配合用橙色系分散染料組成物は、前記橙色分散染料を６５〜９８重量％及び前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、及び前記式［６］で表される染料から選ばれる少なくとも一種の黄色系染料を２〜３５重量％含有するのが好ましい。より好適には前記橙色分散染料が７５〜９７重量％及び前記黄色系染料が３〜２５重量％であり、さらに好適には、前記橙色分散染料が８５〜９６重量％及び前記黄色系染料が４〜１５重量％である。 Among the yellow to orange first disperse dye compositions of the present invention, an orange disperse dye composition for blending (hereinafter referred to as “first disperse orange disperse dye composition”) It can be used in combination with a red dye and a blue dye to produce a disperse dye composition for brown, amber and black. From the viewpoint of build-up property and the like, the first orange disperse dye composition for blending is represented by 65 to 98% by weight of the orange disperse dye and the dye represented by the formula [2], represented by the formula [3]. 2 to 35 at least one dye selected from the dyes represented by formula [4], the dye represented by formula [5], and the dye represented by formula [6] It is preferable to contain by weight. More preferably, the orange disperse dye is 75 to 97% by weight and the yellow dye is 3 to 25% by weight. More preferably, the orange disperse dye is 85 to 96% by weight and the yellow dye is 4%. ~ 15% by weight.
また、本発明の橙色系の第２の分散染料組成物のうち、別の配合用の橙色系分散染料組成物（以下、「第２の配合用橙色系分散染料組成物」と呼ぶ）は、前記橙色分散染料を２０〜８０重量％及び前記式［１７］の染料を２０〜８０重量％含有するのが好ましい。より好適には前記橙色分散染料が２５〜７５重量％及び前記式［１７］の染料が７５〜２５重量％であり、さらに好適には、前記橙色分散染料が３０〜７０重量％及び前記式［１７］の染料が７０〜３０重量％である。 In addition, among the orange-based second disperse dye compositions of the present invention, another orange disperse dye composition for blending (hereinafter referred to as “second orange-dispersed dye composition for blending”) It is preferable to contain 20 to 80% by weight of the orange disperse dye and 20 to 80% by weight of the dye of the formula [17]. More preferably, the orange disperse dye is 25 to 75% by weight and the dye of the formula [17] is 75 to 25% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight and the formula [17]. 17] is 70 to 30% by weight.
また、前記橙色系の第１の分散染料組成物のうち、インクジェット捺染用インクの黒色用として使用する場合には、前記黄色系染料として、前記式［３］で表される染料を用いる前記第１の配合用橙色系分散染料組成物が好ましい。 In addition, among the orange-based first disperse dye compositions, when used as black for ink-jet printing inks, the yellow dye is the first dye that is represented by the formula [3]. An orange disperse dye composition for compounding 1 is preferred.
前記第１及び第３の分散染料組成物に配合される前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、及び前記式［６］で表される染料から選ばれる少なくとも一種の黄色系染料のうち式［４］で表される染料及び式［６］で表される染料の具体例としては、下記の式［４−１］で表される染料、式［４−２］で表される染料、式［４−３］で表される染料、式［６−１］で表される染料及び式［６−２］で表される染料が挙げられる。
本発明の第３の分散染料組成物は、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物を５〜５０重量％と、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、及び前記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料を３〜５０重量％と、前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、及び前記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料を１０〜９０重量％含有するのが好ましい。前記混合割合にすることにより、高耐光性の茶色、紺色、黒色用分散染料組成物を作製することができる。また、灰色の染色物を得ようとする場合は、前記黒色用分散染料組成物の染色濃度を低くすることで所望の色相を得ることができる。さらに好適には、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物が１５〜４５重量％及び前記赤色系染料が５〜４０重量％及び前記青色系染料が２０〜８５重量％である。 The third disperse dye composition of the present invention comprises 5 to 50% by weight of the orange disperse dye or the first disperse orange disperse dye composition, a dye represented by the formula [7], and the formula At least one red selected from the dye represented by [8], the dye represented by formula [9], the dye represented by formula [10], and the dye represented by formula [11] 3 to 50% by weight of a system dye, a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], and a formula [15] It is preferable to contain 10 to 90% by weight of at least one blue dye selected from the dyes described above and the dyes represented by the formula [16]. By adjusting the mixing ratio, a highly light-resistant disperse dye composition for brown, amber, and black can be produced. Moreover, when it is going to obtain a gray dyeing | staining thing, a desired hue can be obtained by making the dyeing | staining density | concentration of the said disperse dye composition for black low. More preferably, the orange disperse dye or the first disperse orange disperse dye composition is 15 to 45% by weight, the red dye is 5 to 40% by weight, and the blue dye is 20 to 85% by weight. It is.
また、前記第３及び第４の分散染料組成物のうち、インクジェット捺染用インクの黒色用として使用する場合には、前記赤色系染料として、前記式［８］で表される染料を用いる前記第３及び第４の分散染料組成物が好ましい。 In addition, among the third and fourth disperse dye compositions, when used as a black color for ink jet textile printing, the red dye is the first dye that is represented by the formula [8]. 3 and 4 disperse dye compositions are preferred.
また、疎水性繊維材料を浸染法又は捺染法で染色する場合には、前記青色系染料として前記式［１４］で表される染料、前記式［１５］で表される染料又は前記式［１６］で表される染料を用いる前記第３及び第４の分散染料組成物が好ましい。インクジェット捺染用インクの黒色用として使用する場合には、前記青色系染料として前記式［１２］で表される染料又は前記式［１３］で表される染料を用いる前記第３及び第４の分散染料組成物が好ましい。 When the hydrophobic fiber material is dyed by the dip dyeing method or the printing method, the blue dye is represented by the dye represented by the formula [14], the dye represented by the formula [15], or the formula [16. The third and fourth disperse dye compositions using a dye represented by the formula: When used as a black ink for ink jet textile printing, the third and fourth dispersions using the dye represented by the formula [12] or the dye represented by the formula [13] as the blue dye. A dye composition is preferred.
前記第３及び第４の分散染料組成物に配合される前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、及び前記式［１１］で表される染料のうち前記式［８］［１０］及び［１１］の染料の具体例としては、下記式［８−１］で表される染料、下記式［８−２］で表される染料、下記式［８−３］で表される染料、下記式［１０−１］で表される染料、下記式［１０−２］で表される染料、下記式［１１−１］で表される染料、及び下記式［１１−２］で表される染料が挙げられる。
前記第３及び第４の分散染料組成物に配合される前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、及び前記式［１６］で表される染料のうち前記式［１３］で表される染料、前記式［１５］で表される染料及び前記式［１６］で表される染料の具体例としては、下記式［１３−１］で表される染料、下記式［１５−１］で表される染料、下記式［１５−２］で表される染料、下記式［１５−３］で表される染料、下記式［１６−１］で表される染料及び下記式［１６−２］で表される染料が挙げられる。
上記高耐光性の茶色、紺色又は黒色用分散染料組成物について、より具体的に説明する。茶色用分散染料組成物は、前記橙色分散染料又は第１の配合用橙色系分散染料組成物を２０〜５０重量％、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、及び前記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料を２０〜５０重量％及び前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、及び前記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料を１０〜５０重量％含有するのが好ましい。さらに好適には、茶色用分散染料組成物は、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物を２５〜４５重量％、前記赤色系染料を２５〜４０重量％及び前記青色系染料を２０〜４０重量％含有する。 The disperse dye composition for brown, amber or black having high light resistance will be described more specifically. The disperse dye composition for brown is represented by the formula [8], the dye represented by the formula [7], 20 to 50% by weight of the orange disperse dye or the first orange disperse dye composition for blending. 20 to 50, at least one red dye selected from the dyes represented by formula [9], the dye represented by formula [10], and the dye represented by formula [11] % By weight and a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], and the formula It is preferable to contain 10 to 50% by weight of at least one blue dye selected from the dyes represented by [16]. More preferably, the disperse dye composition for brown is 25 to 45% by weight of the orange disperse dye or the first orange disperse dye composition for blending, 25 to 40% by weight of the red dye, and the blue color. 20 to 40% by weight of a dye is contained.
また、紺色用分散染料組成物は、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物を５〜２０重量％、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、及び前記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料を３〜２５量％及び前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、及び前記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料を６０〜９０重量％含有するのが好ましい。さらに好適には、紺色用分散染料組成物は、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物を１０〜１５重量％、前記赤色系染料を５〜２０重量％及び前記青色系染料を６５〜８５重量％を含有する。 The disperse dye composition for fading is 5 to 20% by weight of the orange disperse dye or the first orange disperse dye composition for blending, the dye represented by the formula [7], and the formula [8]. A dye represented by formula [9], a dye represented by formula [10], and at least one red dye selected from the dye represented by formula [11]. 3 to 25% by weight and a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], And it is preferable to contain 60 to 90 weight% of at least 1 sort (s) of blue dye chosen from the dye represented by said Formula [16]. More preferably, the disperse dye composition for amber color is 10 to 15% by weight of the orange disperse dye or the first orange disperse dye composition for blending, 5 to 20% by weight of the red dye, and the blue color. Contains 65 to 85% by weight of a system dye.
また、黒色用分散染料組成物は、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物を２０〜４５重量％、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、及び前記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料を５〜２５重量％及び前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、及び前記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料を４５〜７０重量％含有するのが好ましい。さらに好適には、黒色用分散染料組成物は、前記橙色分散染料又は前記第１の配合用橙色系分散染料組成物を２５〜４０重量％、前記赤色系染料を５〜２０重量％及び前記青色系染料を５０〜６５重量％を含有する。 Further, the black disperse dye composition comprises 20 to 45% by weight of the orange disperse dye or the first disperse orange disperse dye composition, a dye represented by the formula [7], and the formula [8]. A dye represented by formula [9], a dye represented by formula [10], and at least one red dye selected from the dye represented by formula [11]. 5 to 25% by weight and a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], And it is preferable to contain 45-70 weight% of at least 1 sort (s) of blue dye chosen from the dye represented by said Formula [16]. More preferably, the disperse dye composition for black is 25 to 40% by weight of the orange disperse dye or the first orange disperse dye composition for blending, 5 to 20% by weight of the red dye, and the blue color. Contains 50 to 65% by weight of the system dye.
また、本発明の第４の分散染料組成物は、第２の配合用橙色系分散染料組成物と、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、及び前記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料と、前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、及び前記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料とを含むことを特徴とする。前記第４の分散染料組成物は、第２の配合用橙色系分散染料組成物５〜５０重量％、前記赤色系染料を３〜５０重量％、及び前記青色系染料を１０〜９０重量％含むのが好ましい。 In addition, the fourth disperse dye composition of the present invention includes a second compounding orange disperse dye composition, a dye represented by the formula [7], a dye represented by the formula [8], At least one red dye selected from the dye represented by the formula [9], the dye represented by the formula [10], and the dye represented by the formula [11], and the formula [12] A dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], and a dye represented by the formula [16]. And at least one selected from the group consisting of blue dyes. The fourth disperse dye composition contains 5 to 50% by weight of the second disperse orange disperse dye composition, 3 to 50% by weight of the red dye, and 10 to 90% by weight of the blue dye. Is preferred.
さらに、前記第１から第４の分散染料組成物には、耐光堅牢度を低下しない範囲において、色相調整用として他の分散染料を添加してもよい。 Furthermore, you may add another disperse dye to the said 1st to 4th disperse dye composition for hue adjustment in the range which does not reduce light fastness.
本発明の前記橙色分散染料及び染料の調合物の調製方法について説明する。前記式［１］で表される染料、前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、前記式［６］で表される染料、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、前記式［１１］で表される染料、前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、前記式［１６］で表される染料及び前記式［１７］で表される染料は、常法により、例えば前記染料のウェットケーキに分散剤としてナフタレンスルホン酸のホルマリン縮合物、リグニンスルホン酸系などのアニオン性界面活性剤と、水とを加え、サンドミル等で微粒子化して前記染料の分散液を得ることができる。前記微粒子の平均粒子径は、染色用としては約０．２〜１．０μｍ、インクジェットインク用としては、０．５μｍ以下が好ましい。前記橙色分散染料及び染料の調合物は、得られた分散液又はそれを乾燥して得られる粉末の形態で使用される。 A method for preparing the orange disperse dye and the dye preparation of the present invention will be described. In the dye represented by the formula [1], the dye represented by the formula [2], the dye represented by the formula [3], the dye represented by the formula [4], and the formula [5] A dye represented by the formula [6], a dye represented by the formula [7], a dye represented by the formula [8], a dye represented by the formula [9], Dye represented by Formula [10], Dye represented by Formula [11], Dye represented by Formula [12], Dye represented by Formula [13], represented by Formula [14] The dye represented by the formula [15], the dye represented by the formula [16] and the dye represented by the formula [17] are dispersed in a wet cake of the dye, for example, by a conventional method. For example, a formalin condensate of naphthalene sulfonic acid, an anionic surfactant such as lignin sulfonic acid, and water, and a sand mill, etc. It can be atomized to obtain a dispersion of the dye. The average particle diameter of the fine particles is preferably about 0.2 to 1.0 μm for dyeing and 0.5 μm or less for inkjet ink. The orange disperse dye and the dye preparation are used in the form of a dispersion obtained or a powder obtained by drying it.
本発明の前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物の調製方法について説明する。前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物は、分散液又はそれを乾燥して得られる粉末の形態の前記橙色分散染料及び染料の調合物を配合することによって得られる。 A method for preparing the first to fourth disperse dye compositions and the first and second disperse dye compositions for blending according to the present invention will be described. The first to fourth disperse dye compositions and the first and second disperse dye compositions for blending are prepared by mixing the orange disperse dye and the dye composition in the form of a dispersion or a powder obtained by drying the dispersion liquid. It is obtained by blending.
前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物を用いて疎水性繊維材料を染色する方法について説明する。まず、水性媒体中に前記橙色分散染料及び前記分散染料組成物の調合物をそれぞれ分散させ、必要に応じてｐＨ調整剤、分散均染剤などを加えた染色浴を準備する。その染色浴に、疎水性繊維材料を浸漬する。前記浸漬は、例えばポリエステル繊維の場合は、加圧下、例えば１０５℃以上、好ましくは１１０〜１４０℃の温度範囲で行う。また、前記染色浴は、更に、ｏ−フェニルフェノール、メチルナフタレン、トリクロロベンゼン等のキャリアーを含んでもよく、前記キャリアーを含む染色浴中で行う浸漬は、比較的低温、例えば１００℃〜１１０℃の温度範囲で行うことができる。また、水性媒体中に前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物を分散させたそれぞれの前記染料分散液を布にパディングし、１００℃以上の温度でのスチーミング方式や乾熱処理を施すいわゆるサーモゾル方式での染色も可能である。また、前記橙色分散染料及び前記分散染料組成物は、天然糊剤（例えばローカストビーンガム、グアーガム、スノウアルギン、カゼイン等）、加工糊剤（例えばカルボキシメチルセルロース等の繊維素誘導体、加工ローカストビーンガム等）、合成糊剤（例えばポリビニルアルコール、ポリビニル酢酸等）、還元防止剤、ｐＨ調整剤、濃染剤等と共に捺染糊を調製し、前記捺染糊を用いて布に印捺した後、スチーミング又はサーモゾル処理する捺染法による染色を行っても良い。更に、紫外線吸収剤を使用して耐光性の優れた染色物を得ることもできる。前記紫外線吸収剤の使用量は特に制限されないが、被染物の重量に対し、０．５〜５重量％（布１００ｇに対して０．５〜５ｇの割合）が好ましく、１〜２重量％が最も好ましい。 A method for dyeing a hydrophobic fiber material using the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending will be described. First, the orange disperse dye and the disperse dye composition are each dispersed in an aqueous medium, and a dyeing bath to which a pH adjuster, a dispersion leveling agent, and the like are added as necessary is prepared. The hydrophobic fiber material is immersed in the dye bath. For example, in the case of polyester fibers, the immersion is performed under pressure, for example, at a temperature of 105 ° C. or higher, preferably 110 to 140 ° C. The dyeing bath may further contain a carrier such as o-phenylphenol, methylnaphthalene, or trichlorobenzene, and the immersion performed in the dyeing bath containing the carrier is performed at a relatively low temperature, for example, 100 ° C to 110 ° C. It can be carried out in the temperature range. Also, each of the dye dispersions in which the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending are dispersed in an aqueous medium is padded on a cloth. Further, dyeing can be performed by a steaming method at a temperature of 100 ° C. or higher, or a so-called thermosol method in which a dry heat treatment is performed. In addition, the orange disperse dye and the disperse dye composition include natural pastes (eg locust bean gum, guar gum, snow argin, casein), processed pastes (eg, fiber derivatives such as carboxymethyl cellulose, processed locust bean gum, etc. ), A synthetic paste (for example, polyvinyl alcohol, polyvinyl acetate, etc.), an anti-reducing agent, a pH adjuster, a thickening agent, etc., and preparing a printing paste, printing on the cloth using the printing paste, Dyeing by a printing method using a thermosol treatment may be performed. Furthermore, it is also possible to obtain a dyed product having excellent light resistance using an ultraviolet absorber. Although the usage-amount of the said ultraviolet absorber is not restrict | limited in particular, 0.5-5 weight% (ratio of 5-5g with respect to 100g of cloth) is preferable with respect to the weight of a to-be-dyed object, and 1-2 weight% Most preferred.
本発明の前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物により染色し得る疎水性繊維材料の具体例としては、通常分散染料に染色されるものであれば特に制限はされないが、例えば、ポリエチレンテレフタレート、テレフタル酸と１、４−ビス（ヒドロキシメチル）シクロヘキサンとの重縮合物等のポリエステル繊維、トリアセテート繊維、ジアセテート繊維及びこれらの混紡品が挙げられ、またこれらと木綿、絹、羊毛等の天然繊維又はナイロン等の合成繊維と上記繊維との混紡品、混織物などが挙げられる。 Specific examples of the hydrophobic fiber material that can be dyed by the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions according to the present invention include ordinary disperse dyes. The dye is not particularly limited as long as it is dyed. For example, polyethylene terephthalate, polyester fiber such as polycondensate of terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane, triacetate fiber, diacetate fiber, and these Examples thereof include blended products, and natural fibers such as cotton, silk and wool or synthetic fibers such as nylon and the above-mentioned fibers, and blended fabrics.
また、前記疎水性繊維材料としては、例えばファインデニールポリエステル繊維が挙げられる。ファインデニールポリエステル繊維は、自動車内装用（特に座席シートの材質）として使用され、風合いが消費者に受け市場を拡大している。これはポリエステル繊維において、繊度を極細化したもの［通常繊度１．０ｄ（デニール）以下の繊維で、さらに好ましい繊度は０．０１〜０．４ｄ（デニール）］であり、マイクロファイバー又は新合繊とも呼ばれる。これらの極細繊維は、太い繊維と同じ染料吸尽率（ビルドアップ率）であっても人間の目には淡色に見えることから、本発明の分散染料を使用して濃色を発現させるのが好ましい。さらに新合繊の中には結晶配向性の高いポリエステルもあり、このようなポリエステルは染色しにくいことから、本発明の分散染料を使用して濃色を発現させるのが好ましい。 Moreover, as said hydrophobic fiber material, a fine denier polyester fiber is mentioned, for example. Fine denier polyester fiber is used for automobile interiors (especially for seat seat materials), and the market is expanding as consumers feel it. This is a polyester fiber with an extremely fineness [usually a fiber having a fineness of 1.0 d (denier) or less, more preferably 0.01 to 0.4 d (denier)], both a microfiber and a new synthetic fiber. be called. Even though these ultrafine fibers have the same dye exhaustion rate (build-up rate) as thick fibers, they appear pale to the human eye. preferable. Furthermore, some of the new synthetic fibers have polyesters with high crystal orientation, and such polyesters are difficult to dye. Therefore, it is preferable to use the disperse dyes of the present invention to develop dark colors.
本発明のインクジェット捺染用インクは、前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物を含有する。 The ink for inkjet textile printing of the present invention contains the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending.
本発明のインクジェット捺染用インクは、平均粒子径が０．５μｍ以下に微粒子化された前記橙色分散染料又は前記分散染料組成物の分散液に、必要に応じて水、水溶性有機溶媒、分散剤等の各種添加剤を加えることにより製造するのが好ましい。前記平均粒子径は、ノズルの目詰まり防止等の観点から０．０５〜０．２μｍがより好適である。 The ink for inkjet textile printing according to the present invention comprises, as necessary, water, a water-soluble organic solvent, and a dispersant in the dispersion liquid of the orange disperse dye or the disperse dye composition finely divided into an average particle size of 0.5 μm or less. It is preferable to produce by adding various additives such as. The average particle size is more preferably 0.05 to 0.2 μm from the viewpoint of preventing nozzle clogging and the like.
前記染料の含有量は、一般的に、分散安定性を保ち、且つ必要な印字濃度が得られることから、インクの全重量に対して０．５〜１５重量％が好ましい。より好ましくは前記染料の含有量は、１〜１２重量％である。 In general, the content of the dye is preferably 0.5 to 15% by weight with respect to the total weight of the ink because dispersion stability is maintained and a necessary print density is obtained. More preferably, the content of the dye is 1 to 12% by weight.
本発明において使用される水溶性有機溶剤としては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、トリエチレングリコール、テトラエチレングリコール、ポリエチレングリコール、ポリプロピレングリコール、チオジグリコール、グリセリン、ジグリセリン等の多価アルコール類、エチレングリコールモノメチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、等のグリコールエーテル類、イソプロピルアルコール、メタノール、エタノール、ベンジルアルコール等のアルコール類、Ｎ−メチル−２−ピロリドン、トリエタノールアミン等の塩基性溶媒が挙げられる。 Examples of the water-soluble organic solvent used in the present invention include ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, thiodiglycol, glycerin, and diglycerin. Polyhydric alcohols, glycols such as ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, alcohols such as isopropyl alcohol, methanol, ethanol, benzyl alcohol, N- Salts such as methyl-2-pyrrolidone and triethanolamine It includes sexual solvent.
上記水溶性有機溶剤のうち、グリセリン、ジエチレングリコール、ポリエチレングリコール３００、４００、プロピレングリコールが好ましい。特に、グリセリンは保湿剤として好ましい。 Of the water-soluble organic solvents, glycerin, diethylene glycol, polyethylene glycol 300, 400, and propylene glycol are preferable. In particular, glycerin is preferred as a humectant.
これら水溶性有機溶剤は、単独でも２種以上混合して使用してもよい。 These water-soluble organic solvents may be used alone or in combination of two or more.
これら水溶性有機溶剤の含有量は、インクの粘度調整、保湿効果による目詰まり防止の点から、インクの全重量に対して５〜５０重量％が好ましい。水溶性有機溶剤の含有量は、インクの全重量に対して１０〜４５重量％がより好ましく、１５〜４０重量％が特に好ましい。 The content of these water-soluble organic solvents is preferably 5 to 50% by weight with respect to the total weight of the ink from the viewpoint of adjusting the viscosity of the ink and preventing clogging due to the moisturizing effect. The content of the water-soluble organic solvent is more preferably 10 to 45% by weight, particularly preferably 15 to 40% by weight, based on the total weight of the ink.
本発明で使用する分散剤は、前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物を水性媒体中に分散させるものであり、特に限定しないが、例えば、アニオン性界面活性剤、ノニオン性界面活性剤であり、アニオン性界面活性剤が好ましい。 The dispersant used in the present invention is for dispersing the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending in an aqueous medium. Although it does not limit, it is an anionic surfactant and a nonionic surfactant, for example, and an anionic surfactant is preferable.
前記アニオン性界面活性剤としては、例えばナフタレンスルホン酸塩のホルマリン縮合物、リグニンスルホン酸塩類、特殊芳香族スルホン酸塩のホルマリン縮合物、クレオソート油スルホン酸塩のホルマリン縮合物、ポリオキシエチレンアルキルエーテル硫酸塩等が挙げられる。 Examples of the anionic surfactant include formalin condensate of naphthalene sulfonate, lignin sulfonate, formalin condensate of special aromatic sulfonate, formalin condensate of creosote oil sulfonate, polyoxyethylene alkyl Examples include ether sulfates.
前記ノニオン性界面活性剤としては、例えば、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレン誘導体、オキシエチレン・オキシプロピレンブロックコポリマーなどが挙げられる。 Examples of the nonionic surfactant include polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene derivative, oxyethylene / oxypropylene block copolymer, and the like.
これら分散剤の含有量は、前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物の分散安定性を良好に保つ目的から、インクの全重量に対して０．５〜２０重量％が好ましい。前記分散剤の含有量は、より好ましくは０．５〜１０重量％であり、特に好ましくは０．５〜５重量％である。 The content of these dispersants is determined in order to maintain good dispersion stability of the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions. 0.5-20 weight% is preferable with respect to the total weight. The content of the dispersant is more preferably 0.5 to 10% by weight, and particularly preferably 0.5 to 5% by weight.
下記式（Ｉ）で示される化合物（式中、Ｒは炭素数２５〜５０のアルキル基を表し、ｎは１０〜１００を表す。）をさらに含むことにより、再分散性の良いインクジェット記録用インク組成物を得ることができる。連続吐出安定性及び長時間放置後の吐出性、長期保存安定性の観点から、下記式（Ｉ）中、Ｒは、好ましくは炭素数３０〜５０のアルキル基であり、炭素数３０〜３５のアルキル基がより好ましい。下記式（Ｉ）中、ｎは、好ましくは２０〜１００であり、より好ましくは３０〜１００である。また、前記アルキル基は直鎖であっても分岐鎖であってもよいが、直鎖状アルキル基が好ましい。
Ｒ−Ｏ−（ＣＨ２ＣＨ２Ｏ）ｎ−Ｈ （Ｉ）An ink for inkjet recording having good redispersibility by further containing a compound represented by the following formula (I) (wherein R represents an alkyl group having 25 to 50 carbon atoms, and n represents 10 to 100). A composition can be obtained. In the following formula (I), R is preferably an alkyl group having 30 to 50 carbon atoms, and has 30 to 35 carbon atoms from the viewpoint of continuous ejection stability, ejection properties after standing for a long time, and long-term storage stability. An alkyl group is more preferred. In following formula (I), n becomes like this. Preferably it is 20-100, More preferably, it is 30-100. The alkyl group may be linear or branched, but is preferably a linear alkyl group.
R—O— (CH 2 CH 2 O) n —H (I)
この化合物（Ｉ）のＨＬＢは、水への溶解性の点から例えば１０以上である。前記ＨＬＢは、好ましくは１４〜１８である。 The HLB of this compound (I) is, for example, 10 or more from the viewpoint of solubility in water. The HLB is preferably 14-18.
前記式（Ｉ）の化合物は、インクの全量に対して好ましくは０．１〜８重量％、より好ましくは０．１〜６重量％、さらに好ましくは０．２〜４重量％使用される。前記式（Ｉ）の化合物を０．１〜８重量％の範囲で用いることにより、添加量が多すぎてインクの粘度が高くなりすぎる問題もなく、より再分散性を向上する効果も発揮できて好ましい。 The compound of the formula (I) is preferably used in an amount of 0.1 to 8% by weight, more preferably 0.1 to 6% by weight, still more preferably 0.2 to 4% by weight, based on the total amount of the ink. By using the compound of the formula (I) in the range of 0.1 to 8% by weight, there is no problem that the added amount is too high and the viscosity of the ink becomes too high, and the effect of improving the redispersibility can be exhibited. It is preferable.
前記式（Ｉ）の化合物の例としては、米国ペトロライト社製の「ユニトックス４５０」（Ｒは炭素数３０の直鎖状アルキル基、ｎは約１０、ＨＬＢ＝１０）、「ユニトックス４８０」（Ｒは炭素数３０の直鎖状アルキル基、ｎは約４０、ＨＬＢ＝１６）、「ユニトックス４９０」（Ｒは炭素数３０の直鎖状アルキル基、ｎは約９４、ＨＬＢ＝１８）、「ユニトックス５５０」（Ｒは炭素数４０の直鎖状アルキル基、ｎが約１２、ＨＬＢ＝１０）、「ユニトックス７５０」（Ｒは炭素数５０の直鎖状アルキル基、ｎが約１６、ＨＬＢ＝１０）などが挙げられる。中でも、前記式（Ｉ）の化合物としては「ユニトックス４８０」及び「ユニトックス４９０」が好ましい。 Examples of the compound of the formula (I) include “Unitox 450” (R is a linear alkyl group having 30 carbon atoms, n is about 10, HLB = 10), “Unitox 480” R is a linear alkyl group having 30 carbon atoms, n is about 40, HLB = 16), “Unitox 490” (R is a linear alkyl group having 30 carbon atoms, n is about 94, HLB = 18), “ “Unitox 550” (R is a linear alkyl group having 40 carbon atoms, n is about 12, HLB = 10), “Unitox 750” (R is a linear alkyl group having 50 carbon atoms, n is about 16, and HLB = 10). Among these, “Unitox 480” and “Unitox 490” are preferable as the compound of the formula (I).
また、前記式（Ｉ）の化合物を添加する場合、作業性の点から、５〜１５重量％程度の式（Ｉ）の化合物の水溶液の形態で添加するのが好ましい。 When the compound of the formula (I) is added, it is preferably added in the form of an aqueous solution of the compound of the formula (I) of about 5 to 15% by weight from the viewpoint of workability.
本発明のインクには、本発明の目的の達成を妨げない範囲において、必要に応じてその他各種添加剤を添加することができる。その他各種添加剤は、例えば、表面調整剤、ヒドロトロープ剤、ＰＨ調整剤、粘度調整剤、防腐剤、防かび剤、光安定剤、キレート化剤、消泡剤等である。 Various other additives can be added to the ink of the present invention as necessary within a range not impeding the achievement of the object of the present invention. Other various additives are, for example, surface conditioners, hydrotropes, pH adjusters, viscosity adjusters, preservatives, fungicides, light stabilizers, chelating agents, antifoaming agents, and the like.
上記添加剤のうち、表面調整剤としては、例えば、フッ素系界面活性剤、ポリエーテル変性ポリジメチルシロキサン、アクリル系重合物などが挙げられ、特にポリエーテル変性ポリジメチルシロキサンやアクリル系重合物が好ましい。これらの表面調整剤は、インクの表面張力を調整し、インクをインク流路系材料に濡れ易くするのに有効である。前記表面調整剤は、インク全重量に対して例えば０．０５〜１重量％、好ましくは、０．１〜０．５重量％の範囲で使用される。前記表面調整剤をインク全重量に対して０．０５重量％以上用いると、表面調整効果が高くなり、１重量％以下用いると、一定の高い表面調整効果が得られるからである。 Among the above additives, examples of the surface conditioner include fluorine-based surfactants, polyether-modified polydimethylsiloxane, and acrylic polymers, and polyether-modified polydimethylsiloxane and acrylic polymers are particularly preferable. . These surface conditioners are effective in adjusting the surface tension of the ink and making the ink easy to get wet with the ink flow path system material. The surface conditioner is used in a range of 0.05 to 1% by weight, preferably 0.1 to 0.5% by weight, based on the total weight of the ink. This is because when the surface conditioning agent is used in an amount of 0.05% by weight or more based on the total weight of the ink, the surface conditioning effect is enhanced, and when it is used at 1% by weight or less, a constant high surface conditioning effect is obtained.
本発明のインクジェット記録用インクの調製方法に特に制限はないが、好ましくは、以下に述べる方法によって調製される。即ち、まず、（ａ）前記橙色分散染料、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物に使用する各染料、分散剤、水、及び、必要に応じて水溶性有機溶媒や前記添加剤を混合して撹拌し、予備分散液を調製することができる。次いで、（ｂ）前記予備分散液をサンドミル等の湿式媒体ミルで分散させ、前記各染料の分散液を得ることができる。（ｃ）前記橙色分散染料のみのインクを調製する場合は、前記分散液に、水、水溶性有機溶媒、必要に応じて前記添加剤を加え濃度調製した後、濾紙等でろ過してから使用することができる。また、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物のインクを調製する場合は、配合用の各分散液を所定量混合し、前記混合分散液に、水、水溶性有機溶媒、必要に応じて前記添加剤を加え濃度調整した後、濾紙等でろ過してから使用してもよい。 The method for preparing the ink for inkjet recording of the present invention is not particularly limited, but it is preferably prepared by the method described below. That is, first, (a) each of the dyes used in the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions, a dispersant, water, and the necessity Depending on the conditions, a water-soluble organic solvent and the additives can be mixed and stirred to prepare a preliminary dispersion. Next, (b) the preliminary dispersion can be dispersed with a wet medium mill such as a sand mill to obtain a dispersion of each dye. (C) When preparing an ink containing only the orange disperse dye, the concentration is adjusted by adding water, a water-soluble organic solvent, and, if necessary, the additive to the dispersion, and then filtering it with a filter paper. can do. When preparing the first to fourth disperse dye compositions and the first and second disperse dye composition inks, predetermined amounts of the respective dispersion liquids are mixed, and the mixed dispersion liquid is prepared. In addition, after adjusting the concentration by adding water, a water-soluble organic solvent, and, if necessary, the additive, it may be used after being filtered with a filter paper or the like.
上記工程（ａ）及び（ｂ）において、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物のインクを調製する場合には、配合用の各染料を混合後、分散剤と共に分散して分散液を得、前記第１から第４の分散染料組成物ならびに第１及び第２の配合用分散染料組成物の分散液に、水、水溶性有機溶媒、必要に応じて前記添加剤を加え濃度調整してもよい。 In the steps (a) and (b), when preparing inks of the first to fourth disperse dye compositions and the first and second disperse dye compositions, the respective dyes for blending are prepared. After mixing, it is dispersed together with a dispersant to obtain a dispersion, and water, a water-soluble organic solvent, a dispersion of the first to fourth disperse dye compositions and the first and second disperse dye compositions for blending, If necessary, the additive may be added to adjust the concentration.
上記方法で得られた分散染料の平均粒子径は０．５μｍ以下が好ましく、より好ましくは０．０５〜０．２μｍである。 The average particle size of the disperse dye obtained by the above method is preferably 0.5 μm or less, more preferably 0.05 to 0.2 μm.
以上、溶媒、色材、分散剤、その他の成分について例示したが、本発明はこの例に限定されるものではない。 As mentioned above, although illustrated about the solvent, the coloring material, the dispersing agent, and other components, the present invention is not limited to this example.
また、インクジェット捺染用インクにおいて、ブラックインクの配合に使用する染料としては、前記式［１］で表される染料、前記式［２］で表される染料、前記式［３］で表される染料、前記式［４］で表される染料、前記式［５］で表される染料、前記式［６］で表される染料、前記式［７］で表される染料、前記式［８］で表される染料、前記式［９］で表される染料、前記式［１０］で表される染料、前記式［１１］で表される染料、前記式［１２］で表される染料、前記式［１３］で表される染料、前記式［１４］で表される染料、前記式［１５］で表される染料、前記式［１６］で表される染料及び前記式［１７］で表される染料の中でも、前記式［１］で表される橙色分散染料及び、黄色系染料としては前記式［３］で表される染料、赤色系染料としては前記式［８］で表される染料、青色系染料としては前記式［１２］で表される染料及び前記式［１３］で表される染料が特に好ましい。 In addition, in the ink for inkjet textile printing, the dye used for blending the black ink is represented by the dye represented by the formula [1], the dye represented by the formula [2], and the formula [3]. Dye, Dye represented by Formula [4], Dye represented by Formula [5], Dye represented by Formula [6], Dye represented by Formula [7], Formula [8 ], A dye represented by the formula [9], a dye represented by the formula [10], a dye represented by the formula [11], a dye represented by the formula [12] The dye represented by the formula [13], the dye represented by the formula [14], the dye represented by the formula [15], the dye represented by the formula [16], and the formula [17]. Among the dyes represented by formula (1), the orange disperse dye represented by the formula [1] and the yellow dye are represented by the formula [3]. Dyes, dye as the red dye represented by the formula [8], the dye as the blue dye represented by the dye and the formula [13] represented by the formula [12] particularly preferable.
また、インクジェット捺染用インクによる捺染は、例えば、以下のようにして行うことができる。まず、前記インクジェット捺染用インクをピエゾ方式インクジェットプリンタにセットして、にじみ防止等の前処理を施したポリエステル布上に吐出して所望の画像を形成することができる。更に、この布を、例えば１５０〜２２０℃の温度で加熱処理して、分散染料をポリエステル繊維に染色する。その後、未固着の分散染料、分散剤等の添加剤及び前処理剤等を還元洗浄及び水洗により除去し、乾燥することにより前記画像の染色物を得ることができる。 In addition, printing with ink for inkjet printing can be performed, for example, as follows. First, the ink for ink-jet textile printing can be set in a piezo-type ink-jet printer and ejected onto a polyester cloth that has been subjected to pretreatment such as bleeding prevention to form a desired image. Furthermore, this cloth is heat-treated at a temperature of, for example, 150 to 220 ° C., and the disperse dye is dyed into polyester fibers. Thereafter, unfixed disperse dye, additives such as a dispersant, pretreatment agent and the like are removed by reduction washing and water washing, and dried to obtain a dyed product of the image.
以下に、実施例を挙げて本発明を更に具体的に説明するが、本発明の態様はこれらに限定されるものではない。尚、下記実施例において「部」は特に断らない限り「重量部」を、また「％」は特に断らない限り「重量％」を意味する。 Hereinafter, the present invention will be described more specifically with reference to examples, but the embodiments of the present invention are not limited thereto. In the following examples, “part” means “part by weight” unless otherwise specified, and “%” means “% by weight” unless otherwise specified.
（実施例１）［橙色分散染料［１−１］の合成］
Ｎ−シアノエチル−Ｎ−ヒドロキシエチルアニリン（１８．７部）とβ−ピコリン（１０．９部）の混合物を５０℃に昇温した。その後、前記混合物中に塩化ベンゾイル（１６．８部）を６０〜７０℃で３時間かけて滴下した後、同温下で１時間保つことによりＮ−シアノエチル−Ｎ−ベンゾイルオキシエチルアニリンを得た。この混合物にスルファミン酸（２部）を加え、酢酸１２０部を添加して溶解させ、氷を加えて前記混合物が５〜１０℃になるように調整してカップラー溶液を得た。Example 1 [Synthesis of Orange Disperse Dye [1-1]]
A mixture of N-cyanoethyl-N-hydroxyethylaniline (18.7 parts) and β-picoline (10.9 parts) was heated to 50 ° C. Thereafter, benzoyl chloride (16.8 parts) was dropped into the mixture at 60 to 70 ° C. over 3 hours, and then kept at the same temperature for 1 hour to obtain N-cyanoethyl-N-benzoyloxyethylaniline. . Sulfamic acid (2 parts) was added to this mixture, 120 parts of acetic acid was added and dissolved, and ice was added to adjust the mixture to 5 to 10 ° C. to obtain a coupler solution.
５℃に冷却した濃硫酸（５０部）及び４３％ニトロシル硫酸（２９．２部）の混合物に、２−アミノ−３−クロロ−５−ニトロ−１−トリフルオロメチルベンゼン（２４部）を５〜１０℃の範囲で徐々に加えた。前記混合物を５〜１０℃で４時間保つことによりジアゾ化合物を得た。 To a mixture of concentrated sulfuric acid (50 parts) and 43% nitrosylsulfuric acid (29.2 parts) cooled to 5 ° C., 5 parts of 2-amino-3-chloro-5-nitro-1-trifluoromethylbenzene (24 parts) were added. Gradually added in the range of -10 ° C. The said mixture was kept at 5-10 degreeC for 4 hours, and the diazo compound was obtained.
前記ジアゾ化合物溶液を前記カップラー溶液に、温度が５〜１０℃に保たれるように氷を適宜加えながら３時間かけて滴下し、カップリング反応を行った。 The diazo compound solution was dropped into the coupler solution over 3 hours while appropriately adding ice so that the temperature was maintained at 5 to 10 ° C., and a coupling reaction was performed.
その後１時間の間、反応混合物を５〜１０℃を保った後、１０００部の水へパージした。得られた混合物を４８％水酸化ナトリウム水溶液でｐＨ＝４に調整後、７０℃に昇温した。同温度で１時間攪拌した後、前記混合物から生成物を濾別し、前記生成物を水洗、乾燥して下記式［１−１］で表されるモノアゾ化合物５４．３部を得た。得られた下記式［１−１］で表されるモノアゾ化合物のアセトン溶液中における最大吸収波長（λｍａｘ）は４２３ｎｍであった。
（実施例２）［橙色分散染料［１−２］の合成］
２−アミノ−３−クロロ−５−ニトロ−１−トリフルオロメチルベンゼンの代わりに２−アミノ−３−ブロモ−５−ニトロ−１−トリフルオロメチルベンゼン（２８．５部）を用いること、及びＮ−シアノエチル−Ｎ−ベンゾイルオキシエチルアニリンの代わりにＮ−シアノエチル−Ｎ−シアノエチルオキシエチルアニリンを用いる以外は実施例１と同様にして、下記式［１−２］で表される染料を得た。なお、Ｎ−シアノエチル−Ｎ−シアノエチルオキシエチルアニリンは、以下のようにして製造した。Ｎ−シアノエチル−Ｎ−ヒドロキシエチルアニリン（１８．７部）とアクリロニトリル（１４．９部）の混合物を８０〜９０℃に昇温し、同温下で２時間保つことによりＮ−シアノエチル−Ｎ−シアノエチルオキシエチルアニリンを得た。Example 2 [Synthesis of Orange Disperse Dye [1-2]]
Substituting 2-amino-3-bromo-5-nitro-1-trifluoromethylbenzene (28.5 parts) for 2-amino-3-chloro-5-nitro-1-trifluoromethylbenzene, and A dye represented by the following formula [1-2] was obtained in the same manner as in Example 1 except that N-cyanoethyl-N-cyanoethyloxyethylaniline was used instead of N-cyanoethyl-N-benzoyloxyethylaniline. . N-cyanoethyl-N-cyanoethyloxyethylaniline was produced as follows. A mixture of N-cyanoethyl-N-hydroxyethylaniline (18.7 parts) and acrylonitrile (14.9 parts) was heated to 80 to 90 ° C., and kept at the same temperature for 2 hours, so that N-cyanoethyl-N— Cyanoethyloxyethylaniline was obtained.
得られた下記式［１−２］で表されるモノアゾ化合物のアセトン溶液中における最大吸収波長（λｍａｘ）は４２９ｎｍであった。
（実施例３）［橙色分散染料［１−３］の合成］
２−アミノ−３−クロロ−５−ニトロ−１−トリフルオロメチルベンゼンの代わりに２−アミノ−３−ブロモ−５−ニトロ−１−トリフルオロメチルベンゼン（２８．５部）を用いること、及びＮ−シアノエチル−Ｎ−ベンゾイルオキシエチルアニリンの代わりにＮ−シアノエチル−Ｎ−ブチルオキシエチルアニリンを用いる以外は、実施例１と同様にして、下記式［１−３］で表される染料を得た。なお、Ｎ−シアノエチル−Ｎ−ブチルオキシエチルアニリンは、以下のようにして製造した。Ｎ−シアノエチルアニリン（１４．６部）と水酸化マグネシウム（３．６部）と水（１８．４部）の混合物を７０℃に昇温した。その後、前記混合物中にｐ−トルエンスルホン酸ｎ−ブチルセロソルブエーテル（３３．７部）を７０〜８５℃で３時間かけて滴下した後、９０〜９５℃で１０時間保つことによりＮ−シアノエチル−Ｎ−ブチルオキシエチルアニリンを得た。Example 3 [Synthesis of Orange Disperse Dye [1-3]]
Substituting 2-amino-3-bromo-5-nitro-1-trifluoromethylbenzene (28.5 parts) for 2-amino-3-chloro-5-nitro-1-trifluoromethylbenzene, and A dye represented by the following formula [1-3] is obtained in the same manner as in Example 1 except that N-cyanoethyl-N-butyloxyethylaniline is used instead of N-cyanoethyl-N-benzoyloxyethylaniline. It was. N-cyanoethyl-N-butyloxyethylaniline was produced as follows. A mixture of N-cyanoethylaniline (14.6 parts), magnesium hydroxide (3.6 parts) and water (18.4 parts) was heated to 70 ° C. Thereafter, p-toluenesulfonic acid n-butyl cellosolve ether (33.7 parts) was dropped into the mixture at 70 to 85 ° C. over 3 hours, and then maintained at 90 to 95 ° C. for 10 hours to obtain N-cyanoethyl-N. -Butyloxyethylaniline was obtained.
得られた下記式［１−３］で表されるモノアゾ化合物のアセトン溶液中における最大吸収波長（λｍａｘ）は４３２ｎｍであった。
（実施例４）［染料調合物［１−１］］
前記式［１−１］で表される染料３０部をナフタレンスルホン酸のホルマリン縮合物３５部と水８５部中でサンドミルにて微粒子化し、次いでリグニンスルホン酸３０部を加えた後、得られた混合物を噴霧乾燥して、前記式［１−１］で表される染料３０％、アニオン系分散剤６５％、水分５％からなる染料調合物［１−１］を得た。Example 4 [Dye Formulation [1-1]]
It was obtained after 30 parts of the dye represented by the formula [1-1] was micronized with a sand mill in 35 parts of a formalin condensate of naphthalenesulfonic acid and 85 parts of water, and then 30 parts of ligninsulfonic acid was added. The mixture was spray-dried to obtain a dye formulation [1-1] comprising 30% of the dye represented by the formula [1-1], 65% of an anionic dispersant, and 5% of water.
（実施例５）［染料調合物［１−２］、［１−３］及び［２］〜［１６］］
前記式［１−１］で表される染料の代わりに、前記式［１−２］で表される染料を用いた以外は、実施例４と同様にして染料３０％、アニオン分散剤６５％、水分５％からなる染料調合物［１−２］を得た。(Example 5) [Dye preparation [1-2], [1-3] and [2] to [16]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [1-2] was used except that the dye represented by the formula [1-2] was used. 30% dye, 65% anionic dispersant A dye preparation [1-2] consisting of 5% water was obtained.
前記式［１−１］で表される染料の代わりに、前記式［１−３］で表される染料を用いた以外は、実施例４と同様にして染料３０％、アニオン分散剤６５％、水分５％からなる染料調合物［１−３］を得た。 Instead of the dye represented by the formula [1-1], a dye represented by the formula [1-3] was used except that the dye represented by the formula [1-3] was used. A dye formulation [1-3] consisting of 5% water was obtained.
前記式［１−１］で表される染料の代わりに、前記式［２］で表される染料、前記式［３］で表される染料、前記式［４−１］で表される染料、前記式［４−２］で表される染料、前記式［４−３］で表される染料、前記式［５］で表される染料、前記式［６−１］で表される染料、前記式［６−２］で表される染料、前記式［７］で表される染料、前記式［８−１］で表される染料、前記式［８−２］で表される染料、前記式［８−３］で表される染料、前記式［９］で表される染料、前記式［１０−１］で表される染料、前記式［１０−２］で表される染料、前記式［１１−１］で表される染料、前記式［１２］で表される染料、前記式［１３−１］で表される染料、前記式［１４］で表される染料、前記式［１５−１］で表される染料、前記式［１５−２］で表される染料、前記式［１５−３］で表される染料、前記式［１６−１］で表される染料及び前記式［１６−２］で表される染料を用いた以外は、実施例４と同様にして染料３０％、アニオン分散剤６５％、水分５％からなる染料調合物［２］、染料調合物［３］、染料調合物［４−１］、染料調合物［４−２］、染料調合物［４−３］、染料調合物［５］、染料調合物［６−１］、染料調合物［６−２］、染料調合物［７］、染料調合物［８−１］、染料調合物［８−２］、染料調合物［８−３］、染料調合物［９］、染料調合物［１０−１］、染料調合物［１０−２］、染料調合物［１１−１］、染料調合物［１２］、染料調合物［１３−１］、染料調合物［１４］、染料調合物［１５−１］、染料調合物［１５−２］、染料調合物［１５−３］、染料調合物［１６−１］及び染料調合物［１６−２］をそれぞれ得た。 Instead of the dye represented by the formula [1-1], the dye represented by the formula [2], the dye represented by the formula [3], and the dye represented by the formula [4-1] , A dye represented by the formula [4-2], a dye represented by the formula [4-3], a dye represented by the formula [5], a dye represented by the formula [6-1] , A dye represented by the formula [6-2], a dye represented by the formula [7], a dye represented by the formula [8-1], a dye represented by the formula [8-2] , A dye represented by the formula [8-3], a dye represented by the formula [9], a dye represented by the formula [10-1], a dye represented by the formula [10-2] A dye represented by the formula [11-1], a dye represented by the formula [12], a dye represented by the formula [13-1], a dye represented by the formula [14], Dye represented by Formula [15-1] The dye represented by the formula [15-2], the dye represented by the formula [15-3], the dye represented by the formula [16-1], and the formula [16-2]. Except for using a dye, the same as in Example 4, a dye preparation [2], a dye preparation [3], and a dye preparation [4-1] comprising 30% dye, 65% anionic dispersant, and 5% moisture. ], Dye Formulation [4-2], Dye Formulation [4-3], Dye Formulation [5], Dye Formulation [6-1], Dye Formulation [6-2], Dye Formulation [7] ], Dye preparation [8-1], dye preparation [8-2], dye preparation [8-3], dye preparation [9], dye preparation [10-1], dye preparation [10 -2], Dye Formulation [11-1], Dye Formulation [12], Dye Formulation [13-1], Dye Formulation [14], Dye Formulation [15-1], Dye Formulation [15 2], dyestuff preparations [15-3] was obtained dyestuff preparations [16-1] and dyestuff preparations [16-2], respectively.
（比較例１）［染料調合物（１）、（２）、（３−１）、（４）及び（３）］
前記式［１−１］で表される染料の代わりに、前記式（１）で表される染料、前記式（２）で表される染料、下記式（３−１）で表される染料、前記式（４）で表される染料及び前記式（３）で表される染料を用いた以外は、実施例４と同様にして染料３０％、アニオン分散剤６５％、水分５％からなる染料調合物（１）、染料調合物（２）、染料調合物（３−１）、染料調合物（４）及び染料調合物（３）をそれぞれ得た。ただし、前記式（３）で表される染料は、前記式［１７］で表される染料と同じ染料であり、実施例の配合例においても式［１７］の代わりに式（３）で表す。Comparative Example 1 [Dye Formulation (1), (2), (3-1), (4) and (3)]
Instead of the dye represented by the formula [1-1], the dye represented by the formula (1), the dye represented by the formula (2), and the dye represented by the following formula (3-1) In the same manner as in Example 4, except that the dye represented by the formula (4) and the dye represented by the formula (3) were used, the dye was composed of 30%, an anionic dispersant 65%, and moisture 5%. Dye preparation (1), dye preparation (2), dye preparation (3-1), dye preparation (4) and dye preparation (3) were obtained. However, the dye represented by the formula (3) is the same dye as the dye represented by the formula [17], and the formula (3) is used instead of the formula [17] in the formulation examples of the examples. .
なお、下記式（３−１）で表される染料は、Ｎ−シアノエチル−Ｎ−ベンゾイルオキシエチルアニリンの代わりに、１−メチル−２−フェニルインドールを用いる以外は、実施例１と同様にして得た。
（実施例６）［レギュラーポリエステルの染色］
染色用ポットに前記染料調合物［１−１］（０．５８ｇ）（染料分０．１７４ｇ）と水３００ｃｃとを入れ、前記混合物のｐＨを酢酸を用いてｐＨ５に調整し染色浴を得た。次いで前記染色用ポット中の染色浴にレギュラーポリエステル織物商品名「トロピカル」（帝人（株）製）（１５ｇ）を投入し、１３０℃で４０分間染色した。その後、通常の方法で前記織物を還元洗浄して、その後乾燥し、染色物Ａ［１−１］を得た。得られた染色物を染色濃度１／１Ｎの染色布とした。(Example 6) [Dyeing of regular polyester]
The dye preparation [1-1] (0.58 g) (0.174 g of dye component) and 300 cc of water were placed in a dyeing pot, and the pH of the mixture was adjusted to pH 5 using acetic acid to obtain a dyeing bath. . Next, regular polyester fabric trade name “Tropical” (manufactured by Teijin Ltd.) (15 g) was added to the dyeing bath in the dyeing pot and dyed at 130 ° C. for 40 minutes. Thereafter, the woven fabric was reduced and washed by a normal method and then dried to obtain a dyed product A [1-1]. The dyed product thus obtained was used as a dyeing cloth having a dyeing density of 1/1 N.
（実施例７）
前記染料調合物［１−１］に代えて、前記染料調合物［１−２］０．５８ｇ（染料分０．１７４ｇ）及び前記染料調合物［１−３］０．５８ｇ（染料分０．１７４ｇ）を使用する以外は、実施例６と同様にそれぞれ染色し、染色物Ａ［１−２］及び染色物Ａ［１−３］を得た。(Example 7)
Instead of the dye preparation [1-1], 0.58 g of the dye preparation [1-2] (0.174 g of dye) and 0.58 g of the dye preparation [1-3] (0. Except using 174g), it dye | stained similarly to Example 6, respectively, and obtained the dyeing | staining A [1-2] and the dyeing | staining A [1-3].
（比較例２）
前記染料調合物［１−１］に代えて、前記染料調合物（１）（０．５８ｇ）（染料分０．１７４ｇ）、前記染料調合物（２）（０．５８ｇ）（染料分０．１７４ｇ）、前記染料調合物（３−１）（０．５８ｇ）（染料分０．１７４ｇ）、前記染料調合物（４）（０．５８ｇ）（染料分０．１７４ｇ）及び前記染料調合物（３）（０．５８ｇ）（染料分０．１７４ｇ）を使用する以外は、実施例６と同様にそれぞれ染色し、染色物Ａ（１）、染色物Ａ（２）、染色物Ａ（３−１）、染色物Ａ（４）及び染色物Ａ（３）を得た。(Comparative Example 2)
In place of the dye preparation [1-1], the dye preparation (1) (0.58 g) (dye content 0.174 g), the dye preparation (2) (0.58 g) (dye content 0. 174 g), the dye formulation (3-1) (0.58 g) (0.174 g dye content), the dye formulation (4) (0.58 g) (0.174 g dye content) and the dye formulation ( 3) Dyeing was carried out in the same manner as in Example 6 except that (0.58 g) (dye content 0.174 g) was used, and dyeing A (1), dyeing A (2), dyeing A (3- 1) Dyeing A (4) and Dyeing A (3) were obtained.
実施例６及び７ならびに比較例２で得られた染色物について、耐光堅牢度、昇華堅牢度及び吸尽性（ビルドアップ性）を測定し、その結果を表１に示す。また、使用した各染料のアセトン溶液の最大吸収波長（λｍａｘ）も表１に記載した。 With respect to the dyed products obtained in Examples 6 and 7 and Comparative Example 2, the light fastness, sublimation fastness and exhaustion (build-up property) were measured, and the results are shown in Table 1. Table 1 also shows the maximum absorption wavelength (λmax) of the acetone solution of each dye used.
［耐光堅牢度］
耐光堅牢度は、染色濃度１／１Ｎの染色布を用い、ＪＩＳ Ｌ ０８４２−１９９６に準じて、紫外線カーボンアーク灯法で、紫外線フェードメーター Ｕ４８（スガ試験機（株）製）を用いて、試験装置内の温度は、装置内に収容されたブラックパネルと呼ばれる基準板の温度が６３±３℃になるように保ち、８０時間照射した後、ＪＩＳ Ｌ ０８０４−１９９４ 変褪色用グレースケール（対応国際規格：ＩＳＯ １０５−Ａ０２）で判定した。[Light fastness]
Light fastness was tested using a dyed cloth with a dyeing density of 1/1 N, an ultraviolet carbon arc lamp method according to JIS L 0842-1996, and an ultraviolet fade meter U48 (manufactured by Suga Test Instruments Co., Ltd.). The temperature inside the apparatus is maintained such that the temperature of a reference plate called a black panel accommodated in the apparatus is 63 ± 3 ° C., and after irradiation for 80 hours, JIS L 0804-1994 gray scale for color change Standard: ISO 105-A02).
［昇華堅牢度］
昇華堅牢度は、染色濃度１／１Ｎの染色布を用い、ＪＩＳ Ｌ ０８７９−１９９６（対応国際規格：ＩＳＯ １０５−Ｐ０１：１９９３）に準じて処理温度１８０±２℃×３０秒（添付汚染布＝東レ（株）製ポリエステル商品名「テトロン」及びナイロン）にて行った。[Sublimation fastness]
The sublimation fastness is a dyeing cloth having a dyeing density of 1/1 N, and a processing temperature of 180 ± 2 ° C. × 30 seconds according to JIS L 0879-1996 (corresponding international standard: ISO 105-P01: 1993) (attached contaminated cloth = This was carried out using Toray's polyester trade name “Tetron” and nylon.
［吸尽性（ビルドアップ性）］
吸尽性（ビルドアップ性）は、染色濃度１／２Ｎ、１／１Ｎ、２／１Ｎの染色布の濃度比較を目視判定した。◎は「非常に良好である」、○は「良好である」、△は「やや劣る」、×は「劣っている」を意味する。
Exhaustability (build-up property) was determined visually by comparing the density of dyed cloth with dyeing densities of 1 / 2N, 1 / 1N, and 2 / 1N. ◎ means “very good”, ◯ means “good”, Δ means “somewhat inferior”, and x means “inferior”.
表１から明らかなように、レギュラーポリエステル布を用いた染色物において、本発明の式［１］で表される橙色分散染料については、耐光堅牢度が４−５級、昇華堅牢度が３−４級以上で、ビルドアップ性も良好であり、耐光性、昇華堅牢度及びビルドアップ性に優れていた。一方、比較例の前記式（１）で表す染料及び前記式（２）で表す染料については、昇華堅牢度及びビルドアップ性に優れていたが、耐光性が４級と本発明の橙色分散染料より少し劣っていた。また、前記式（３−１）で表す染料については、耐光性は本発明の橙色分散染料と同等であり優れているが、昇華堅牢度が２級と劣っており、ビルドアップ性も良くなかった。また、前記式（４）で表す染料については、耐光性及びビルドアップ性は優れているが、昇華堅牢度が３級と劣っていた。また、前記式（３）で表す染料については、耐光性が非常に優れているが、昇華堅牢度が３級と劣っており、ビルドアップ性も良くなかった。 As is apparent from Table 1, in the dyed product using the regular polyester cloth, the orange disperse dye represented by the formula [1] of the present invention has a light fastness of 4-5 and a sublimation fastness of 3- It was grade 4 or higher, had good build-up properties, and was excellent in light resistance, sublimation fastness and build-up properties. On the other hand, the dye represented by the formula (1) and the dye represented by the formula (2) of the comparative example were excellent in sublimation fastness and build-up property, but had a light resistance of 4th grade and the orange disperse dye of the present invention It was a little inferior. In addition, the dye represented by the formula (3-1) is excellent in light resistance, which is equivalent to the orange disperse dye of the present invention, but the sublimation fastness is inferior to the second grade, and the build-up property is not good. It was. Moreover, about the dye represented by the said Formula (4), although light resistance and buildup property were excellent, the sublimation fastness was inferior to the 3rd grade. Further, the dye represented by the formula (3) has very good light resistance, but its sublimation fastness is inferior to the third grade, and the build-up property is not good.
また、本発明の橙色分散染料は、式（１）で表す染料、式（２）で表す染料、式（３−１）で表す染料及び式（３）で表す染料に比較して、λｍａｘが長波長側であることからも分かるように少し赤みの色相を呈していた。 Further, the orange disperse dye of the present invention has a λmax higher than that of the dye represented by the formula (1), the dye represented by the formula (2), the dye represented by the formula (3-1), and the dye represented by the formula (3). As can be seen from the longer wavelength side, it had a slightly reddish hue.
（実施例８）［ファインデニールポリエステル繊維の染色］
染色用ポットに前記染料調合物［１−１］（０．２８ｇ）（染料分０．０８４ｇ）と水３００ｃｃを入れ、前記混合物のｐＨを酢酸を用いてｐＨ５に調整し染色浴を得た。次いで前記染色用ポット中の染色浴に繊度０．３デニールの新合繊（ファインデニールポリエステル繊維）（１５ｇ）を投入し、１３０℃で４０分間染色した。その後、通常の方法で前記新合繊を還元洗浄して、その後乾燥し、橙色の染色物Ｂ［１−１］を得た。(Example 8) [Dyeing of fine denier polyester fiber]
The dye formulation [1-1] (0.28 g) (0.084 g of dye component) and 300 cc of water were placed in a dyeing pot, and the pH of the mixture was adjusted to pH 5 using acetic acid to obtain a dyeing bath. Next, a new synthetic fiber (fine denier polyester fiber) (15 g) having a fineness of 0.3 denier was charged into the dyeing bath in the dyeing pot and dyed at 130 ° C. for 40 minutes. Thereafter, the new synthetic fiber was reduced and washed by a usual method, and then dried to obtain an orange dyed product B [1-1].
（実施例９）
前記染料調合物［１−１］に代えて、前記染料調合物［１−２］（０．２８ｇ）（染料分０．０８４ｇ）及び前記染料調合物［１−３］（０．２８ｇ）（染料分０．０８４ｇ）を使用する以外は、実施例８と同様にそれぞれ染色し、染色物Ｂ［１−２］及び染色物Ｂ［１−３］を得た。Example 9
Instead of the dye preparation [1-1], the dye preparation [1-2] (0.28 g) (0.084 g dye content) and the dye preparation [1-3] (0.28 g) ( Dyeing was performed in the same manner as in Example 8 except that 0.084 g) of the dye content was used, and Dyeing B [1-2] and Dyeing B [1-3] were obtained.
（比較例３）
前記染料調合物［１−１］に代えて、前記染料調合物（１）（０．２８ｇ）（染料分０．０８４ｇ）、前記染料調合物（２）（０．２８ｇ）（染料分０．０８４ｇ）、前記染料調合物（３−１）（０．２８ｇ）（染料分０．０８４ｇ）、前記染料調合物（４）（０．２８ｇ）（染料分０．０８４ｇ）及び前記染料調合物（３）（０．２８ｇ）（染料分０．０８４ｇ）をそれぞれ使用する以外は実施例８と同様にそれぞれ染色し、染色物Ｂ（１）、染色物Ｂ（２）、染色物Ｂ（３−１）、染色物Ｂ（４）及び染色物Ｂ（３）を得た。(Comparative Example 3)
Instead of the dye preparation [1-1], the dye preparation (1) (0.28 g) (0.084 g of dye component), the dye preparation (2) (0.28 g) (dye component of 0.1%). 084 g), the dye preparation (3-1) (0.28 g) (0.084 g dye content), the dye preparation (4) (0.28 g) (0.084 g dye content) and the dye preparation ( 3) Dyeing was carried out in the same manner as in Example 8 except that (0.28 g) (0.084 g of dye component) was used, and dyeing B (1), dyeing B (2), dyeing B (3- 1) Dyeing B (4) and Dyeing B (3) were obtained.
（実施例１０）
前記染色用ポット中の染色浴にベンゾトリアゾール系紫外線吸収剤サンライフＬＰＳ−９５０（日華化学（株）製）（０．３０ｇ）を追加する以外は、実施例８と同様の方法で新合繊（ファインデニールポリエステル繊維）（１５ｇ）を染色し、橙色の染色物Ｃ［１−１］を得た。(Example 10)
New synthetic fiber in the same manner as in Example 8 except that benzotriazole ultraviolet absorber Sunlife LPS-950 (manufactured by Nikka Chemical Co., Ltd.) (0.30 g) is added to the dyeing bath in the dyeing pot. (Fine denier polyester fiber) (15 g) was dyed to obtain an orange dyed product C [1-1].
（実施例１１）
前記染料調合物［１−１］に代えて、前記染料調合物［１−２］及び前記染料調合物［１−３］用いて実施例１０と同様にそれぞれ染色し、染色物Ｃ［１−２］及び染色物Ｃ［１−３］を得た。Example 11
Instead of the dye preparation [1-1], the dye preparation [1-2] and the dye preparation [1-3] were used, respectively, in the same manner as in Example 10 to obtain a dyed product C [1- 2] and dyed product C [1-3] were obtained.
（比較例４）
前記染料調合物［１−１］に代えて、前記染料調合物（１）、（２）、（３−１）、（４）及び（３）を用いて実施例１０と同様にそれぞれ染色し、染色物Ｃ（１）、染色物Ｃ（２）、染色物Ｃ（３−１）、染色物Ｃ（４）及び染色物Ｃ（３）を得た。(Comparative Example 4)
In place of the dye preparation [1-1], the dye preparations (1), (2), (3-1), (4) and (3) were used for dyeing in the same manner as in Example 10. , Dyed product C (1), dyed product C (2), dyed product C (3-1), dyed product C (4) and dyed product C (3) were obtained.
実施例８〜１１及び比較例３、４で得られた染色物Ｂ及びＣについて、耐光堅牢度を測定した。耐光堅牢度は、ＪＩＳ Ｌ ０８４２より過酷な試験方法であるトヨタ法に基づいて行った。具体的には、耐光堅牢度は、染色布にウレタンフォームを裏付けし、キセノンウェザーメーター（ブラックパネル温度７３±３℃、放射照度１５０Ｗ／ｍ２、スガ試験機（株）製、スーパーキセノンウェザーメーター ＳＣ７５０）を用いて明暗３８サイクル照射した後、ＪＩＳ Ｌ ０８０４変褪色用グレースケールで判定した。The light fastness was measured for the dyed articles B and C obtained in Examples 8 to 11 and Comparative Examples 3 and 4. The light fastness was determined based on the Toyota method, which is a test method more severe than JIS L 0842. Specifically, the light fastness is a xenon weather meter (black panel temperature 73 ± 3 ° C., irradiance 150 W / m 2 , Super Xenon Weather Meter, manufactured by Suga Test Instruments Co. After irradiating 38 cycles of light and dark using SC750), it was determined with a gray scale for JIS L 0804 color change.
耐光堅牢度の測定に用いる上記のトヨタ法とは、トヨタ自動車株式会社の試験規格であり、キセノンアーク（キセノンランプ）を光源として行われ、繊維、プラスチックを、試験対象とする。通常、試験には、キセノンウェザーメーターと呼ばれる試験装置が用いられる。ここでは、光源の照射強度を１５０Ｗ／ｍ２（波長３００〜４００ｎｍ）とし、その照射方法は、明暗法即ち、所定時間照射した後所定時間照射を止めて暗くし、これを繰り返して行った。具体的には、照射時間３．８時間及び暗時間１時間を１サイクルとして、３８サイクル（約１８２時間）行った。試験装置内の（試験雰囲気の）湿度は、照射中５０±５％、暗時間中９５±５％に保った。また試験装置内の温度は、装置内に収容されたブラックパネルと呼ばれる基準板の温度が７３±３℃になるように保った。装置内に収容されて試験が行われる試験布（繊維）は、ウレタンで裏打ちした。The above-mentioned Toyota method used for measuring the light fastness is a test standard of Toyota Motor Corporation, which uses xenon arc (xenon lamp) as a light source, and tests fibers and plastics. Usually, a test device called a xenon weather meter is used for the test. Here, the irradiation intensity of the light source was set to 150 W / m 2 (wavelength 300 to 400 nm), and the irradiation method was performed by repeating the light and dark method, that is, irradiating for a predetermined time and then darkening for a predetermined time. Specifically, 38 cycles (about 182 hours) were performed with an irradiation time of 3.8 hours and a dark time of 1 hour as one cycle. The humidity (in the test atmosphere) in the test apparatus was kept at 50 ± 5% during irradiation and 95 ± 5% during the dark time. The temperature in the test apparatus was maintained so that the temperature of a reference plate called a black panel accommodated in the apparatus was 73 ± 3 ° C. The test cloth (fiber) accommodated in the apparatus to be tested was lined with urethane.
実施例８〜１１及び比較例３、４で得られた染色物Ｂ及びＣについて、前記方法により測定した耐光堅牢度は、以下のとおりである。染色物Ｂ［１−１］については４＋、染色物Ｂ［１−２］については４、染色物Ｂ［１−３］については４、染色物Ｃ［１−１］については４−５、染色物Ｃ［１−２］については４＋、染色物Ｃ［１−３］については４＋、染色物Ｂ（１）については３、染色物Ｂ（２）については３−４、染色物Ｂ（３−１）については４＋、染色物Ｂ（４）については３−４、染色物Ｂ（３）については４＋、染色物Ｃ（１）については３−４、染色物Ｃ（２）については３−４、染色物（３−１）については４−５、染色物（４）については４、染色物Ｃ（３）については４−５であった。前記結果は、以下の表２にも示す。
表２から明らかなように、トヨタ法によるファインデニールポリエステル繊維を用いた染色物の耐光性試験において、本発明の式［１］で表される橙色分散染料については耐光堅牢度が４級以上と優れており、特に前記式［１−１］で表される染料については、耐光性が非常に優れていた。一方、前記式（１）で表される染料及び前記式（２）で表される染料については、耐光堅牢度が３−４級以下と少し劣っており、紫外線吸収剤の効果も少なかった。また、前記式（３−１）で表される染料及び前記式（３）で表される染料については、耐光性が非常に優れていた。また、前記式（４）で表される染料については、本発明の染料に比べ耐光性が少し劣っていた。 As is clear from Table 2, in the light resistance test of the dyed product using the fine denier polyester fiber by the Toyota method, the light fastness of the orange disperse dye represented by the formula [1] of the present invention is 4th or higher. In particular, the dye represented by the formula [1-1] was very excellent in light resistance. On the other hand, with respect to the dye represented by the formula (1) and the dye represented by the formula (2), the light fastness was slightly inferior to 3-4 grade or less, and the effect of the ultraviolet absorber was also small. Moreover, about the dye represented by the said Formula (3-1) and the dye represented by the said Formula (3), light resistance was very excellent. The dye represented by the formula (4) was slightly inferior in light resistance to the dye of the present invention.
したがって、表１及び表２から明らかなように、本発明の橙色分散染料は、耐光性、昇華堅牢度及びビルドアップ性に優れており、前記式［１−１］で表される染料は特に耐光性が優れていた。一方、前記式（１）で表される染料及び前記式（２）で表される染料は、昇華堅牢度及びビルドアップ性に優れていたが、耐光性が本発明の橙色分散染料より劣っており、特にトヨタ法の場合に顕著であった。また、前記式（３−１）で表される染料及び前記式（３）で表される染料は、耐光性は非常に優れているが、昇華堅牢度が劣っており、ビルドアップ性も良くなかった。また、前記式（４）で表される染料は、ビルドアップ性は優れているが、昇華堅牢度が劣っており、さらにトヨタ法を用いた耐光堅牢度も劣っていた。 Therefore, as is clear from Table 1 and Table 2, the orange disperse dye of the present invention is excellent in light resistance, sublimation fastness and build-up property, and the dye represented by the formula [1-1] is particularly Light resistance was excellent. On the other hand, the dye represented by the formula (1) and the dye represented by the formula (2) were excellent in sublimation fastness and build-up property, but the light resistance was inferior to the orange disperse dye of the present invention. This was particularly noticeable in the case of the Toyota Law. Further, the dye represented by the formula (3-1) and the dye represented by the formula (3) are very excellent in light resistance, but are inferior in sublimation fastness and good in build-up property. There wasn't. In addition, the dye represented by the formula (4) has excellent build-up property, but is inferior in sublimation fastness and inferior in light fastness using the Toyota method.
（実施例１２）
前記染料調合物［１−１］、前記染料調合物［１−２］、前記染料調合物［１−３］、染料調合物［２］、染料調合物［３］、染料調合物［４−１］、染料調合物［４−２］、染料調合物［４−３］、染料調合物［５］、染料調合物［６−１］、染料調合物［６−２］、染料調合物［７］、染料調合物［８−１］、染料調合物［８−２］、染料調合物［８−３］、染料調合物［９］、染料調合物［１０−１］、染料調合物［１０−２］、染料調合物［１１−１］、染料調合物［１２］、染料調合物［１３−１］、染料調合物［１４］、染料調合物［１５−１］、染料調合物［１５−２］、染料調合物［１５−３］、染料調合物［１６−１］及び染料調合物［１６−２］及び前記染料調合物（３）を、以下の表３〜表５に示す割合（重量部）で配合して、分散染料組成物１〜２６を調製した。Example 12
The dye preparation [1-1], the dye preparation [1-2], the dye preparation [1-3], the dye preparation [2], the dye preparation [3], and the dye preparation [4- 1], Dye Formula [4-2], Dye Formula [4-3], Dye Formula [5], Dye Formula [6-1], Dye Formula [6-2], Dye Formula [ 7], Dye Formula [8-1], Dye Formula [8-2], Dye Formula [8-3], Dye Formula [9], Dye Formula [10-1], Dye Formula [ 10-2], Dye Formulation [11-1], Dye Formulation [12], Dye Formulation [13-1], Dye Formulation [14], Dye Formulation [15-1], Dye Formulation [ 15-2], Dye Formulation [15-3], Dye Formulation [16-1], Dye Formulation [16-2] and the Dye Formulation (3) are shown in Tables 3 to 5 below. In proportion (parts by weight) Combined and were prepared disperse dye composition 1-26.
染色用ポットに各染料調合物（０．２８ｇ）（染料分０．０８４ｇ）と水（３００ｃｃ）とベンゾトリアゾール系紫外線吸収剤サンライフＬＰＳ−９５０（日華化学（株）製）（０．３０ｇ）とを入れ、前記混合物のｐＨを酢酸を用いてｐＨ５に調整し染色浴を得た。次いで前記染色用ポット中の染色浴に実施例８で用いた新合繊織物（ファインデニールポリエステル繊維）１５ｇを投入し、１３０℃で４０分間染色した。その後、通常の方法で前記新合繊織物を還元洗浄して、その後乾燥し、染色物Ｄをそれぞれ得た。得られた染色物Ｄについて、染色物Ｂ及びＣの場合と同様に耐光堅牢度を測定したところ、良好な耐光堅牢度を示した。
以下にインクジェット捺染用インクの調製方法について説明する。 A method for preparing ink for inkjet textile printing will be described below.
（実施例１３）
［インク用分散液［１−１］の調製］
前記式［１−１］で表される染料（２０部）、分散剤としてアニオン性界面活性剤の特殊芳香族スルホン酸ナトリウムのホルマリン縮合物（花王（株）製、商品名「デモールＳＮＢ」）（１０部）、「ユニトックス４８０」（米国ペトロライト社製、前記化学式（Ｉ）の化合物でＲが炭素数３０の直鎖状アルキル基、ｎが約４０、ＨＬＢが１６に相当する）（３部）、水（１２７部）を含む混合物に、直径０．４ｍｍのジルコンビーズ（３３０部）を使用して、サンドミルにて３５時間微粒子化して、染料濃度１２．５％のインク用分散液［１−１］を得た。前記染料の平均粒径は０．１０μｍであった。(Example 13)
[Preparation of Ink Dispersion [1-1]]
Dye (20 parts) represented by the formula [1-1], a formalin condensate of a special aromatic sodium sulfonate as an anionic surfactant as a dispersant (trade name “Demol SNB” manufactured by Kao Corporation) (10 parts), “Unitox 480” (manufactured by Petrolite, USA, R is a linear alkyl group having 30 carbon atoms, n is about 40, and HLB corresponds to 16). Part) and water (127 parts), using a 0.4 mm diameter zircon bead (330 parts) and finely pulverizing for 35 hours with a sand mill, a dispersion for ink having a dye concentration of 12.5% [ 1-1] was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［１−２］の調製］
前記式［１−１］で表される染料に代えて、前記式［１−２］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［１−２］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [1-2]]
In the case of the dispersion liquid for ink [1-1] except that the dye represented by the formula [1-2] (20 parts) is used instead of the dye represented by the formula [1-1] Similarly, an ink dispersion [1-2] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［３］の調製］
前記式［１−１］で表される染料に代えて、前記式［３］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［３］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [3]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [3] (20 parts) was used except that the same as in the case of the ink dispersion [1-1]. Thus, an ink dispersion [3] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［４−３］の調製］
前記式［１−１］で表される染料に代えて、前記式［４−３］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［４−３］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [4-3]]
In the case of the dispersion liquid for ink [1-1] except that the dye represented by the formula [4-3] (20 parts) is used instead of the dye represented by the formula [1-1] Similarly, an ink dispersion [4-3] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［５］の調製］
前記式［１−１］で表される染料に代えて、前記式［５］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［５］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [5]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [5] (20 parts) was used except that the same as in the case of the ink dispersion [1-1]. Thus, an ink dispersion [5] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［８−３］の調製］
前記式［１−１］で表される染料に代えて、前記式［８−３］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［８−３］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [8-3]]
In the case of the dispersion liquid for ink [1-1], in place of the dye represented by the formula [1-1], a dye represented by the formula [8-3] (20 parts) is used. Similarly, an ink dispersion [8-3] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［１２］の調製］
前記式［１−１］で表される染料に代えて、前記式［１２］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［１２］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [12]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [12] (20 parts) was used except that the same as in the case of the ink dispersion [1-1]. Thus, an ink dispersion [12] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
［インク用分散液［１３−１］の調製］
前記式［１−１］で表される染料に代えて、前記式［１３−１］で表される染料（２０部）を使用する以外は、インク用分散液［１−１］の場合と同様にして染料濃度１２．５％のインク用分散液［１３−１］を得た。前記染料の平均粒径は０．１０μｍであった。[Preparation of Ink Dispersion [13-1]]
In the case of the dispersion liquid for ink [1-1], except that the dye represented by the formula [13-1] (20 parts) is used instead of the dye represented by the formula [1-1], Similarly, an ink dispersion [13-1] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.
（実施例１４）
以下にブラックインクの例について説明し、その配合割合を表６に示す。
［ブラックインク［２７］の調製］
インク用分散液［１−１］（５６部）、インク用分散液［１２］（８４部）及びインク用分散液［１３−１］（８４部）の混合液に、水溶性有機溶剤としてグリセリン（１００部）及び表面調整剤としてポリエーテル変性ポリジメチルシロキサン（ビックケミー・ジャパン（株）製、商品名「ＢＹＫ−３４８」）（１．０部）を添加し、そこへ水を加え全量を４００部として染料濃度を７％に調整したインクを作成した。各染料の重量割合は、式［１−１］で表される染料：式［１２］で表される染料：式［１３−１］で表される染料＝２５：３７．５：３７．５であった。(Example 14)
Examples of black ink will be described below, and the blending ratio is shown in Table 6.
[Preparation of black ink [27]]
Glycerin as a water-soluble organic solvent in a mixture of the ink dispersion [1-1] (56 parts), the ink dispersion [12] (84 parts) and the ink dispersion [13-1] (84 parts) (100 parts) and polyether-modified polydimethylsiloxane (manufactured by BYK Japan Japan Co., Ltd., trade name “BYK-348”) (1.0 part) as a surface conditioner (1.0 part) was added, and water was added thereto to make a total amount of 400 As a part, an ink having a dye concentration adjusted to 7% was prepared. The weight ratio of each dye is as follows: Dye represented by formula [1-1]: Dye represented by formula [12]: Dye represented by formula [13-1] = 25: 37.5: 37.5 Met.
［ブラックインク［２８］の調製］
インク用分散液［１−２］（４０部）、インク用分散液［３］（１８部）、インク用分散液［８−３］（１１部）、インク用分散液［１２］（６７部）及びインク用分散液［１３−１］（８８部）の混合液に、水溶性有機溶剤としてグリセリン（１００部）及び表面調整剤として商品名「ＢＹＫ−３４８」（ビックケミー・ジャパン（株）製）（１．０部）を添加し、そこへ水を加え全量を４００部として染料濃度を７％に調整したインクを作成した。各染料の重量割合は、式［１−２］で表される染料：式［３］で表される染料：式［８−３］で表される染料：式［１２］で表される染料：式［１３−１］で表される染料＝１８：８：５：３０：３９であった。
Ink dispersion liquid [1-2] (40 parts), Ink dispersion liquid [3] (18 parts), Ink dispersion liquid [8-3] (11 parts), Ink dispersion liquid [12] (67 parts) ) And dispersion liquid [13-1] (88 parts) for ink, glycerin (100 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) as a surface conditioner. ) (1.0 part) was added, and water was added thereto to prepare an ink having a total amount of 400 parts and a dye concentration adjusted to 7%. The weight ratio of each dye is the dye represented by the formula [1-2]: the dye represented by the formula [3]: the dye represented by the formula [8-3]: the dye represented by the formula [12]. : Dye represented by formula [13-1] = 18: 8: 5: 30: 39.
（実施例１５）
以下にオレンジインクの例について説明し、その配合割合を表７に示す。
［オレンジインク［２９］の調製］
インク用分散液［１−１］（１０１部）及びインク用分散液［３］（４３部）の混合液に、分散剤として商品名「デモール ＳＮＢ」（花王（株）製）の１０％水溶液（４０部）、水溶性有機溶剤としてグリセリン（１１０部）及び表面調整剤として商品名「ＢＹＫ−３４８」（ビックケミー・ジャパン（株）製）（１．０部）を添加し、そこへ水を加え全量を４００部として染料濃度を４．５％に調整したインクを作成した。各染料の重量割合は、式［１−１］で表される染料：式［３］で表される染料＝７０：３０であった。(Example 15)
Examples of orange ink will be described below, and the blending ratio is shown in Table 7.
[Preparation of orange ink [29]]
A 10% aqueous solution of a trade name “Demol SNB” (manufactured by Kao Corporation) as a dispersant in a mixture of the ink dispersion [1-1] (101 parts) and the ink dispersion [3] (43 parts). (40 parts), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) (1.0 part) as a surface conditioner are added, and water is added thereto. In addition, an ink was prepared in which the total amount was 400 parts and the dye concentration was adjusted to 4.5%. The weight ratio of each dye was the dye represented by the formula [1-1]: the dye represented by the formula [3] = 70: 30.
［オレンジインク［３０］の調製］
インク用分散液［１−１］（９４部）及びインク用分散液［４−３］（５０部）の混合液に、分散剤として商品名「デモール ＳＮＢ」（花王（株）製）の１０％水溶液（４０部）、水溶性有機溶剤としてグリセリン（１１０部）及び、表面調整剤として商品名「ＢＹＫ−３４８」（ビックケミー・ジャパン（株）製）（１．０部）を添加し、そこへ水を加え全量を４００部として染料濃度を４．５％に調整したインクを作成した。各染料の重量割合は、式［１−１］で表される染料：式［４−３］で表される染料＝６５：３５であった。[Preparation of orange ink [30]]
In the mixed liquid of the ink dispersion [1-1] (94 parts) and the ink dispersion [4-3] (50 parts), 10 of the trade name “Demol SNB” (manufactured by Kao Corporation) as a dispersant. % Aqueous solution (40 parts), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by BYK Japan KK) (1.0 part) as a surface conditioner, there Water was added to make a total amount of 400 parts, and an ink having a dye concentration adjusted to 4.5% was prepared. The weight ratio of each dye was the dye represented by the formula [1-1]: the dye represented by the formula [4-3] = 65: 35.
［オレンジインク［３１］の調製］
インク用分散液［１−１］（１０１部）及びインク用分散液［５］（４３部）の混合液に、分散剤として「デモール ＳＮＢ」（花王（株）製）の１０％水溶液（４０部）、水溶性有機溶剤としてグリセリン（１１０部）、表面調整剤として商品名「ＢＹＫ−３４８」（ビックケミー・ジャパン（株）製）（１．０部）を添加し、そこへ水を加え全量を４００部として染料濃度を４．５％に調整したインクを作成した。各染料の重量割合は、式［１−１］で表される染料：式［５］で表される染料＝７０：３０であった。[Preparation of orange ink [31]]
A 10% aqueous solution (40) of “Demol SNB” (manufactured by Kao Corporation) as a dispersant in a mixture of the ink dispersion [1-1] (101 parts) and the ink dispersion [5] (43 parts). Part), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) (1.0 part) as a surface conditioner, and water is added to the whole amount. Ink was prepared by adjusting the dye concentration to 4.5%. The weight ratio of each dye was the dye represented by the formula [1-1]: the dye represented by the formula [5] = 70: 30.
［オレンジインク［３２］の調製］
インク用分散液［１−１］（８９部）及びインク用分散液［６−１］（５５部）の混合液に、分散剤として「デモール ＳＮＢ」（花王（株）製）の１０％水溶液（４０部）、水溶性有機溶剤としてグリセリン（１１０部）、表面調整剤として商品名「ＢＹＫ−３４８」（ビックケミー・ジャパン（株）製）（１．０部）を添加し、そこへ水を加え全量を４００部として染料濃度を４．５％に調整したインクを作成した。各染料の重量割合は、式［１−１］で表される染料：式［６−１］で表される染料＝６２：３８であった。
A 10% aqueous solution of “Demol SNB” (manufactured by Kao Corporation) as a dispersant in a mixture of the ink dispersion [1-1] (89 parts) and the ink dispersion [6-1] (55 parts). (40 parts), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) (1.0 part) as a surface conditioner are added, and water is added thereto. In addition, an ink was prepared in which the total amount was 400 parts and the dye concentration was adjusted to 4.5%. The weight ratio of each dye was dye represented by formula [1-1]: dye represented by formula [6-1] = 62: 38.
（実施例１６）［インクジェット捺染用インクによる染色］
前記インクジェット捺染用インク［２７］〜［３２］をそれぞれ別々にピエゾ方式インクジェットプリンタにセットして、滲み防止等の前処理を施した１５００ｍｍ幅×１０ｍ長のレギュラーポリエステル布上に印字解像度３６０×３６０ｄｐｉで単色・塗りつぶし印刷を行った。その結果、いずれのインクジェット捺染用インク［２７］〜［３２］についても、目詰まりも発生せず良好な吐出安定性を示した。さらに、該ポリエステル布を乾燥後、１７５℃の過熱蒸気中で７分間熱処理を行い、前記ポリエステル布を染色した。未固着の染料、分散剤等の添加剤及び前処理剤等を還元洗浄及び水洗により除去し、乾燥することにより、それぞれの色相の染色物Ｅを得た。得られた染色物Ｅの耐光堅牢度を前記トヨタ法に基づいて測定したところ、いずれも良好な耐光堅牢度を示した。Example 16 [Dyeing with Inkjet Textile Ink]
Ink-jet textile printing inks [27] to [32] are individually set in a piezo-type ink jet printer and printed on a regular polyester cloth of 1500 mm width × 10 m length subjected to pretreatment such as bleeding prevention, with a printing resolution of 360 × 360 dpi. A single color / filled print was performed. As a result, any of the inkjet printing inks [27] to [32] exhibited good ejection stability without causing clogging. Further, the polyester cloth was dried and then heat-treated in superheated steam at 175 ° C. for 7 minutes to dye the polyester cloth. Unfixed dyes, additives such as dispersants, pretreatment agents and the like were removed by reduction washing and water washing, and dried to obtain a dyed product E of each hue. When the light fastness of the obtained dyed product E was measured based on the Toyota method, all showed good light fastness.
Claims (17)
下記式［２］で表される染料、下記式［３］で表される染料、下記式［４］で表される染料、下記式［５］で表される染料、及び下記式［６］で表される染料から選ばれる少なくとも一種の黄色系染料とを含み、
黄色から橙色系であることを特徴とする分散染料組成物。
Dye represented by the following formula [2], dye represented by the following formula [3], dye represented by the following formula [4], dye represented by the following formula [5], and formula [6] And at least one yellow dye selected from the dyes represented by
A disperse dye composition characterized by being yellow to orange.
下記式［７］で表される染料、下記式［８］で表される染料、下記式［９］で表される染料、下記式［１０］で表される染料、及び下記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料と、
下記式［１２］で表される染料、下記式［１３］で表される染料、下記式［１４］で表される染料、下記式［１５］で表される染料、及び下記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料とを含むことを特徴とする分散染料組成物。
Dye represented by the following formula [7], dye represented by the following formula [8], dye represented by the following formula [9], dye represented by the following formula [10], and formula [11] At least one red dye selected from the dyes represented by:
Dye represented by the following formula [12], dye represented by the following formula [13], dye represented by the following formula [14], dye represented by the following formula [15], and formula [16] A disperse dye composition comprising at least one blue dye selected from the dyes represented by formula (1).
前記赤色系染料を３〜５０重量％、及び
前記青色系染料を１０〜９０重量％含む請求項９に記載の分散染料組成物。5 to 50% by weight of the orange disperse dye according to claim 1 or the disperse dye composition according to claim 5.
The disperse dye composition according to claim 9, comprising 3 to 50% by weight of the red dye and 10 to 90% by weight of the blue dye.
下記式［７］で表される染料、下記式［８］で表される染料、下記式［９］で表される染料、下記式［１０］で表される染料、及び下記式［１１］で表される染料から選ばれる少なくとも１種の赤色系染料と、
下記式［１２］で表される染料、下記式［１３］で表される染料、下記式［１４］で表される染料、下記式［１５］で表される染料、及び下記式［１６］で表される染料から選ばれる少なくとも１種の青色系染料とを含むことを特徴とする分散染料組成物。
Dye represented by the following formula [7], dye represented by the following formula [8], dye represented by the following formula [9], dye represented by the following formula [10], and formula [11] At least one red dye selected from the dyes represented by:
Dye represented by the following formula [12], dye represented by the following formula [13], dye represented by the following formula [14], dye represented by the following formula [15], and formula [16] A disperse dye composition comprising at least one blue dye selected from the dyes represented by formula (1).
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| JP5610910B2 (en) * | 2010-08-06 | 2014-10-22 | 株式会社ミマキエンジニアリング | Printing method |
| JP5851417B2 (en) * | 2010-11-19 | 2016-02-03 | 日本化薬株式会社 | Disperse dye and method for dyeing hydrophobic fiber material using the same |
| CN103228741B (en) * | 2010-11-30 | 2015-07-08 | 日本化药株式会社 | Disperse dyes and method for dyeing hydrophobic fiber material using same |
| CN102127315A (en) * | 2010-12-24 | 2011-07-20 | 上海宜连化工科技有限公司 | Blue disperse dye composition with high light fastness and application thereof |
| CN102127313B (en) * | 2010-12-24 | 2014-07-16 | 上海宜连化工科技有限公司 | High-light-fastness red disperse dye composition and use thereof |
| US8506654B2 (en) | 2011-03-29 | 2013-08-13 | Dystar L.P. | Disperse dye mixtures which have a high degree of light fastness and build-up |
| JP5773520B2 (en) | 2011-06-10 | 2015-09-02 | 日本化薬株式会社 | Disperse dye composition and method for dyeing hydrophobic fiber material using the same |
| KR20140045518A (en) * | 2011-08-01 | 2014-04-16 | 닛뽄 가야쿠 가부시키가이샤 | Disperse dye composition and method for dyeing hydrophobic textile materials using same |
| JP5817028B2 (en) * | 2011-08-23 | 2015-11-18 | 東洋インキＳｃホールディングス株式会社 | Coloring composition for color filter, and color filter |
| KR101416893B1 (en) * | 2012-06-08 | 2014-07-08 | 공명도 | Orange disperse dye composition having excellent moisture resistance |
| CN102732059B (en) * | 2012-07-03 | 2014-09-03 | 浙江闰土股份有限公司 | Composite dye composition, composite disperse dye and preparation method thereof |
| CN102827492A (en) * | 2012-09-28 | 2012-12-19 | 吴江市绿洲染料化工有限公司 | Performance-improved disperse blue dye mixture |
| CN102827493A (en) * | 2012-09-28 | 2012-12-19 | 吴江市绿洲染料化工有限公司 | Performance-improved disperse blue dye mixture |
| CN103073922A (en) * | 2013-01-21 | 2013-05-01 | 江苏亚邦染料股份有限公司 | Orange disperse dye composition |
| JP6041152B2 (en) * | 2013-11-13 | 2016-12-07 | セイコーエプソン株式会社 | Inkjet ink composition for sublimation transfer, ink set, and method for producing dyed product |
| JP6285281B2 (en) * | 2014-05-30 | 2018-02-28 | セーレン株式会社 | Inkjet ink set, inkjet printing method, and inkjet printed matter |
| KR101723853B1 (en) * | 2015-07-09 | 2017-04-07 | 일신교역 주식회사 | Dyes composition for heat transfer printing on nylon fabrics |
| TWI561585B (en) * | 2015-12-09 | 2016-12-11 | Ind Tech Res Inst | Dye and dyeing method |
| KR101865357B1 (en) * | 2016-07-13 | 2018-07-13 | 일신교역 주식회사 | Eco-friendly high strength disperse black dyes composition for heat transfer printing of polyester fiber |
| CN106398308B (en) * | 2016-08-31 | 2017-09-22 | 江苏亚邦染料股份有限公司 | A kind of black disperse dye composition, black disperse dye and its colouring method of high light-fast fastness |
| CN108069875B (en) * | 2016-11-16 | 2021-10-08 | 浙江龙盛化工研究有限公司 | Synthesis process of N-cyanoethyl-N-benzoyloxyethylaniline |
| JP6822175B2 (en) * | 2017-01-30 | 2021-01-27 | セイコーエプソン株式会社 | Selection method |
| CN107286703B (en) * | 2017-05-26 | 2019-08-20 | 杭州吉华江东化工有限公司 | A kind of high solarization dispersed black dye mixture and its application |
| CN107556807B (en) * | 2017-09-18 | 2020-11-03 | 江苏龙达纺织科技有限公司 | Environment-friendly ultra-black dye ink |
| KR102060607B1 (en) | 2017-12-29 | 2020-02-11 | 아크로마코리아 주식회사 | The preparing method of disperse orange dye |
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| JP5203545B2 (en) * | 1999-09-20 | 2013-06-05 | チバ ホールディング インコーポレーテッド | Azo dyes, their production process and their use in dyeing or printing hydrophobic fiber materials |
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