JP2018035343A - 合成繊維を染色するための染料としてのインディゴ誘導体の使用、新規インディゴ誘導体、及び合成繊維を染色する方法 - Google Patents
合成繊維を染色するための染料としてのインディゴ誘導体の使用、新規インディゴ誘導体、及び合成繊維を染色する方法 Download PDFInfo
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- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 235000000177 Indigofera tinctoria Nutrition 0.000 title claims abstract description 62
- 229940097275 indigo Drugs 0.000 title claims abstract description 62
- 229920002994 synthetic fiber Polymers 0.000 title claims abstract description 60
- 239000012209 synthetic fiber Substances 0.000 title claims abstract description 58
- 238000004043 dyeing Methods 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 20
- 230000000694 effects Effects 0.000 claims abstract description 16
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229920002302 Nylon 6,6 Polymers 0.000 claims abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 3
- 229920000572 Nylon 6/12 Polymers 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 33
- 238000010438 heat treatment Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 8
- 239000002657 fibrous material Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- -1 polyethylene terephthalate Polymers 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 5
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 5
- 238000002845 discoloration Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 4
- 229920002292 Nylon 6 Polymers 0.000 claims description 3
- 229920000299 Nylon 12 Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000979 synthetic dye Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 20
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002759 woven fabric Substances 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000009981 jet dyeing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VIFKLIUAPGUEBV-UHFFFAOYSA-N 2-(3-hydroxy-1h-indol-2-yl)-1h-indol-3-ol Chemical compound N1C2=CC=CC=C2C(O)=C1C1=C(O)C2=CC=CC=C2N1 VIFKLIUAPGUEBV-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 2
- 230000005661 hydrophobic surface Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- COHYTHOBJLSHDF-BUHFOSPRSA-N indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 206010033546 Pallor Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005517 mercerization Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0083—Solutions of dyes
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- 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
- D06P1/22—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 vat dyestuffs including indigo
- D06P1/228—Indigo
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- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/042—Material containing basic nitrogen containing amide groups using vat or sulfur dyes
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- 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
- D06P3/523—Polyesters using vat or sulfur dyes
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- 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
- D06P3/82—Textiles which contain different kinds of fibres
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- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
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- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
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- 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
- D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
- D06P5/2066—Thermic treatments of textile materials
- D06P5/2077—Thermic treatments of textile materials after dyeing
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Abstract
【解決手段】式(I)で表される新規なインディゴ誘導体。インディゴ誘導体の染料としての使用、合成繊維を染色する方法、及び染色された繊維、並びに染色された繊維を含む物品。前記合成繊維がPA6、PA66、PA612、PET、PBT及びそれらの混合物から選択される、インディゴ誘導体の使用。
(R1及びR2は夫々独立してH、t−Boc又はFmoc基、但し、R1及びR2は、両者共水素ではない;R3及びR4は夫々独立してH、C1−4アルキル、C1-4アルコキシ、ハロゲン、NO2、CHO又は置換フェニル)
【選択図】図1A
Description
この不便さは、合成繊維及び編織布は、疎水性表面を持っているので、インディゴ染色溶液のように水系の染色溶液で染色するのが難しいことが原因である。
但し、
・ R1及びR2は、それぞれ独立して、水素原子、及び、好ましくはt−Boc、Fmoc基、ベンジルカルバメート、トリフェニルメチルアミン、ベンジルアミン、及びトリフロロアセタミドから選択された立体障害された疎水性保護基から選択される。但し、R1及びR2は、両者ともに水素ではない、
・ R3及びR4は、それぞれ独立して、水素、メチルのようなアルキル基、メトキシのようなアルコキシ基、ハロゲン、NO2,CHO、及び任意選択的に置換フェニルから選択される。
(a)式(I)の少なくとも1つのN−保護インディゴ誘導体の少なくとも部分的に塩化された還元形化合物を含む染料溶液を含んだ染色浴を製造すること、及び
(b)単一又は複数の染色槽を使用して、合成繊維を染色して、式(I)のインディゴ誘導体で染色された合成繊維の表面を得ること。
ここで、
− R1’及びR2’は、それぞれ独立して、水素、t−Boc及びFmoc基から選択される、但し、R1’及びR2’は、両者ともに水素ではない。
− R3’及びR4’は、それぞれ独立して、水素、メチルのようなアルキル基、
メトキシのようなアルコキシ基、ハロゲン、NO2、CHO、及び任意選択的に置換フェニル基から選択される。
但し、
− R1’及びR2’の一方がt−Bocで、他方が水素である。又は、
− R1’及びR2’の両者がt−Bocである場合、
R3’及びR4’は、水素でも、ハロゲン原子でもない。
但し、
− R1’及びR2’の両者がFmocである場合、
R3’及びR4’は、両者とも水素原子ではない。
式(I’)の化合物の製造方法は、本発明の別の主題である。
[実施例]
標題の化合物の製造を、下記のスキームに従って実行する。化合物Aを、室温で、4当量のジ−tert−ブチルジカボネート(tBOC2O)及び2当量のN,N’−ジメチルアミノピリジン(DMAP)と一緒に、ジクロロメタン(CH2Cl2)中で、1〜3日間攪拌して、化合物Bを生成する(反応は薄層クロマトグラフでモニタする)。溶媒を、ロータリエバポレータを使用して室温で蒸発させ、次いで水を添加し、混合物を更に30分間攪拌する。混合物を、焼結ディスク濾過ロートで濾過する。その後、炉液を2MのHClで酸化し、一晩中攪拌する。最後に、溶液を、焼結ディスク濾過ロートで濾過し、60℃以下の温度で乾燥する。
標題の化合物の製造を、下記のスキームに従って実行する。
DMAc(30mL)中の、インディゴ溶液(1.5g、5.7mmol)を製造し、水酸化ナトリウム(0.27g,11.2mmol)を添加した。次いで、反応混合物を、0℃に冷却し、窒素雰囲気下で攪拌を続けた。DMAC(30mL)中の、9−フルオレニルメチルクロロホルマート(Fmoc−Cl、3.0g、11.5mmol)溶液を点滴添加し、混合物を更に6時間混合した。混合物を酢酸エチルで3回抽出し、次いで水で3回抽出した。収取した有機層をMgSO4上で乾燥した。カラムクロマトグラフ(クロロホルム/ヘキサン=10/1、及び、次いでクロロホルム/酢酸エチル=10/1)で精製し、次いで(クロロホルム/ヘキサンから)再結晶して、実質的に純粋なCを得た。
染色工程は、従来の還元剤、及び式(I)のN−保護インディゴ誘導体の2つの異なる濃縮液を使用する水系インディゴ誘導体染色溶液を製造することによって実行される。合成繊維として、ポリエステル(PES)ヤーンの編織布を使用する。パドバッチ装置を使用する。染色工程は、1回の浸漬工程及び空気暴露工程を、それぞれ、室温で、3秒及び90秒間継続する。パッドバッチ法のパラメータは、絞り圧力が2バール、及び速度が2m/分であった。絞り工程に続いて、120℃、2分間テンターで乾燥させた。
Claims (14)
- 前記合成繊維は、ポリアミド6(PA6)、ポリアミド66(PA66)、ポリアミド612(PA612)、ポリアミド12(PA12)、ポリエチレンテレフタレート(PET)、ポリブチレンテレフタレート(PBT)、及びそれらの混合物から選択されることを特徴とする請求項1のインディゴ誘導体の使用。
- 前記R1及び/又は前記R2は、t−Boc又はFmoc基であることを特徴とする請求項1又は2のインディゴ誘導体の使用。
- 前記C1−4アルキルは、メチルで、前記C1−4アルコキシは、メトキシであることを特徴とする請求項1〜3のいずれか1項のインディゴ誘導体の使用。
- −前記R1及び前記R2の少なくとも1つはt−Bocであり、かつ
−前記R3及び前記R4は、両者共水素原子又はハロゲン原子であることを特徴とする請求項1〜3のいずれか1項に記載のインディゴ誘導体の使用。 - a) 少なくとも部分的に塩化され、還元形の請求項1〜5のいずれか1項で規定した式(I)の少なくとも1つのN−保護されたインディゴ誘導体を含む染色溶液を含む染色浴を製造すること、及び
b) 単一又は複数の染色タンクを使用して、合成繊維を染色して、請求項1〜5のいずれか1項で規定した式(I)の前記インディゴ誘導体で表面が染色された合成繊維を得ることを含む、式(I)のインディゴ誘導体を使用して、リング効果を挙げて、合成繊維を染色する方法。 - 更に、
c)ステップb)から得た編織布の少なくとも1部を熱処理して、更なる染料又は変色剤の不存在下に、その色を変えるステップを含む請求項6に記載の方法。 - 請求項6又は7の方法によって得られる、熱処理によってリング効果及び変色可能性を示すインディゴで染色された合成繊維材料。
- 前記合成繊維材料は、請求項1〜5のいずれか1項に規定した式(I)の少なくとも1つの化合物で染色された、請求項8の繊維材料。
- 請求項8又は9による繊維材料を含む物品。
- 前記色は、中間使用者及び/又は最終使用者による熱処理によって変えられる請求項10の物品。
- 式(I’)の化合物、
式(I’)において、
・前記R1’及び前記R2’は、それぞれ独立して、水素、t−Boc及びFmoc基から選択される、但し、前記R1’及び前記R2’は、両者共水素ではない。
・前記R3’及び前記R4’は、それぞれ独立して、水素、C1−4アルキル、C1-4アルコキシ、ハロゲン、NO2、CHO、及びフェニルから選択される。
但し、前記R1’及び前記R2’の少なくとも1つがt−Bocで、他方が水素の場合、又は前記R1’及び前記R2’の両者がt−Bocの場合、前記R3’及び前記R4’は、水素でも、ハロゲン原子でもない。
但し、前記R1’及び前記R2’の両者がFmoc基の場合、前記R3’及び前記R4’は、両者共水素原子ではない。 - 前記R1’及び前記R2’の両者が、t−Boc又はFmocであることを特徴とする請求項12の化合物。
- モノ−及びジ−t−Bocインディゴ誘導体から選択される請求項12又は13の化合物。
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EP16195293.2A EP3312337B1 (en) | 2016-10-24 | 2016-10-24 | Use of indigo derivatives for dyeing synthetic textiles, novel indigo derivatives and process for dyeing synthetic textiles |
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