JP2020525580A - 分散アゾ染料 - Google Patents
分散アゾ染料 Download PDFInfo
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- JP2020525580A JP2020525580A JP2019571229A JP2019571229A JP2020525580A JP 2020525580 A JP2020525580 A JP 2020525580A JP 2019571229 A JP2019571229 A JP 2019571229A JP 2019571229 A JP2019571229 A JP 2019571229A JP 2020525580 A JP2020525580 A JP 2020525580A
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- 239000000987 azo dye Substances 0.000 title description 2
- 239000000463 material Substances 0.000 claims abstract description 21
- 238000004043 dyeing Methods 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 12
- 239000002657 fibrous material Substances 0.000 claims abstract description 12
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- -1 methoxycarbonylmethyl group Chemical group 0.000 claims abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
- 239000004753 textile Substances 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 238000007639 printing Methods 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 229920000728 polyester Polymers 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- LEGWLJGBFZBZSC-UHFFFAOYSA-N n-[2-[(2,6-dicyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(C#N)C=C([N+]([O-])=O)C=C1C#N LEGWLJGBFZBZSC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- JSRUDOBCTLPTFO-UHFFFAOYSA-N 2-[5-acetamido-n-(2-acetyloxyethyl)-4-[(2-bromo-4,6-dinitrophenyl)diazenyl]-2-methoxyanilino]ethyl acetate Chemical compound C1=C(N(CCOC(C)=O)CCOC(C)=O)C(OC)=CC(N=NC=2C(=CC(=CC=2Br)[N+]([O-])=O)[N+]([O-])=O)=C1NC(C)=O JSRUDOBCTLPTFO-UHFFFAOYSA-N 0.000 claims description 2
- XREZMAAQVYVESP-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-4-fluorophenoxy]ethoxy]-5-fluoroanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC(F)=CC=C1OCCOC1=CC=C(F)C=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O XREZMAAQVYVESP-UHFFFAOYSA-N 0.000 claims description 2
- VHLFTCNAACYPDY-UHFFFAOYSA-N methyl 3-[n-ethyl-4-[(5-nitro-2,1-benzothiazol-3-yl)diazenyl]anilino]propanoate Chemical compound C1=CC(N(CCC(=O)OC)CC)=CC=C1N=NC1=C2C=C([N+]([O-])=O)C=CC2=NS1 VHLFTCNAACYPDY-UHFFFAOYSA-N 0.000 claims description 2
- QBCBEQSWSOZGPB-UHFFFAOYSA-N n-[5-[bis(2-methoxyethyl)amino]-2-[(5-nitro-2,1-benzothiazol-3-yl)diazenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CCOC)CCOC)=CC=C1N=NC1=C2C=C([N+]([O-])=O)C=CC2=NS1 QBCBEQSWSOZGPB-UHFFFAOYSA-N 0.000 claims description 2
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 5
- 210000004243 sweat Anatomy 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- XKNLKANSESPUNO-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(CN(C2=CC(=CC=C2)NC(C)=O)CC)C=CC=1 Chemical compound [N+](=O)([O-])C=1C=C(CN(C2=CC(=CC=C2)NC(C)=O)CC)C=CC=1 XKNLKANSESPUNO-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002156 mixing Methods 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
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/0813—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 OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
-
- 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
- C09B29/0815—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 -C(=O)-
-
- 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
- D06P1/18—Azo 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
- 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
- D06P3/40—Cellulose acetate
- D06P3/46—Cellulose triacetate
- D06P3/48—Cellulose triacetate using dispersed 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)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
【化1】
(式中、
R1は、ブロモ基、ニトロ基、シアノ基、メチル基、メトキシ基又はトリフルオロメチル基であり、
R2は、水素原子、クロロ基、ブロモ基又はトリフルオロメチル基であり、
R3は、水素原子、クロロ基、ブロモ基、メトキシ基、トリフルオロメチル基、ニトロ基又はシアノ基であり、及び
R4は、メチル基、エチル基、n−プロピル基、2−メトキシエチル基、メトキシカルボニルメチル基又は2−メトキシカルボニルエチル基であるが、
但し、R2がクロロ基又はブロモ基を表す場合、R1はシアノ基であり、及びR2はトリフルオロメチル基を表す場合、R1はシアノ基又はニトロ基である。)
で表される分散アゾ染料、該染料の調製方法、並びに半合成の及び、特に、合成の疎水性繊維材料、より特には織物材料の染色又は捺染におけるそれらの使用に関する。
Description
で表される染料に相当する。
式(2)
使用される酸の例は、塩酸、酢酸、プロピオン酸、硫酸及びリン酸である。
ルー376、シー.アイ.ディスパースブルー378、シー.アイ.ディスパースブルー380、シー.アイ.ディスパースグリーン9、シー.アイ.ディスパースバイオレット107、「国際公開第2014/016072号」において記載された式(101)乃至(179)で表される化合物、「国際公開第2009/013122号」において記載された式(101)乃至(106)で表される化合物、及び「中国特許101955691」において記載された式II−2、II−3、II−4及びIII−1乃至III−8で表される化合物から成る群から選択される少なくとも一種さらなる染料を含む染料混合物に関する。
本発明に係る染料はまた、例えば、熱転写捺染等の現代の複製方法に適している。
RT=室温
実施例I.1
A.ジアゾ化
濃硫酸20gを、実験室反応装置中に入れた。氷5gを添加した後、溶液を室温まで冷やした。この温度で、2−ブロモ−4−ニトロ−6−シアノアニリン6.01gを追加した。室温で30分間撹拌し、そして、10℃まで冷却した後、40%のニトロシル硫酸8.2gを滴下添加した。該反応混合物を10℃でさらに60分間撹拌した。その後、過剰な亜硝酸塩をスルファミン酸の添加により分解した。
B.カップリング
「仏国特許出願2008404」の実施例1aに記載された方法に従って調製された7.83gの微粉状のN−3−ニトロベンジル−N−エチル−3−アセチルアミノアニリンを10mlのエタノールの中で懸濁し、氷20gと混ぜた。撹拌しながら、ステップAから得られたジアゾニウム塩の溶液を60分内に滴下添加した。該反応混合物を、室温で一晩撹拌した。濾過、洗浄及び乾燥後、式(101)で表される染料11.75g(83%)が得られた。
II.1ポリエステル染色
実施例I.1で調製した式(101)で表される染料1質量部を、商業的に入手できる分散剤4部及び水15部と共に粉砕した。その配合物を用いて、135℃で、高温吸尽方法にてポリエステル織布上に、1%の染色物(該染料及び該基質に基づく)が生成された。
試験結果:該染色物の耐光堅牢性は、AATCC61試験及びISO105試験の結果と同様優れていた。該染料のビルドアップ性は非常に良好であった。
Claims (10)
- 式(1)
R1は、ブロモ基、ニトロ基、シアノ基、メチル基、メトキシ基又はトリフルオロメチル基であり、
R2は、水素原子、クロロ基、ブロモ基又はトリフルオロメチル基であり、
R3は、水素原子、クロロ基、ブロモ基、メトキシ基、トリフルオロメチル基、ニトロ基又はシアノ基であり、及び
R4は、メチル基、エチル基、n−プロピル基、2−メトキシエチル基、メトキシカルボニルメチル基又は2−メトキシカルボニルエチル基であるが、
但し、R2がクロロ基又はブロモ基を表す場合、R1はシアノ基であり、及びR2はトリフルオロメチル基を表す場合、R1はシアノ基又はニトロ基である。)
で表される染料。 - R1はシアノ基である、請求項1に記載の式(1)で表される染料。
- R2はクロロ基である、請求項1又は請求項2に記載の式(1)で表される染料。
- R3は水素原子である、請求項1乃至請求項3のいずれか一項に記載の式(1)で表される染料。
- R4はメチル基、エチル基、メトキシカルボニルメチル基又は2−メトキシカルボニルエチル基である、請求項1乃至請求項4のいずれか一項に記載の式(1)で表される染料。
- 式(2)
- 請求項1に記載の式(1)で表される少なくとも1種の染料及び
シー.アイ.ディスパースブルー60、シー.アイ.ディスパースブルー79:1、シー.アイ.ディスパースブルー72:2、シー.アイ.ディスパースブルー148、シー.アイ.ディスパースブルー149、シー.アイ.ディスパースブルー165、シー.アイ.ディスパースブルー165:1、シー.アイ.ディスパースブルー207、シー.アイ.ディスパースブルー284、シー.アイ.ディスパースブルー295、シー.アイ.ディスパースブルー316、シー.アイ.ディスパースブルー337、シー.アイ.ディスパースブルー354、シー.アイ.ディスパースブルー366、シー.アイ.ディスパースブルー367、シー.アイ.ディスパースブルー368、シー.アイ.ディスパースブルー376、シー.アイ.ディスパースブルー378、シー.アイ.ディスパースブルー380、シー.アイ.ディスパースグリーン9、シー.アイ.ディスパースバイオレット107、「国際公開第2014/016072号」において記載された式(101)乃至(179)で表される化合物、「国際公開第2009/013122号」において記載された式(101)乃至(106)で表される化合物、及び「中国特許101955691」において記載された式II−2、II−3、II−4及びIII−1乃至III−8で表される化合物から成る群から選択される少なくとも一種さらなる染料を含む、染料混合物。 - 半合成の又は合成の疎水性繊維材料、特に織物材料の染色又は捺染方法であって、請求項1に記載の式(1)で表される少なくとも一種の染料又は請求項7に記載の染料混合物を該材料に塗布する、又は該材料中に混和する方法。
- 前記疎水性材料、好ましくは織物材料がポリエステル繊維を含有する請求項8に記載の方法。
- 請求項8又は請求項9に記載の染色された又は捺染された材料。
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PCT/EP2018/062523 WO2019001832A1 (en) | 2017-06-28 | 2018-05-15 | DISCOVERED AZOIC DYES |
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TWI811654B (zh) * | 2021-03-31 | 2023-08-11 | 財團法人紡織產業綜合研究所 | 紡織品的雙面均染方法及使用其製造而成的多彩紗線 |
Citations (3)
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GB1275603A (en) * | 1968-05-13 | 1972-05-24 | Eastman Kodak Co | Monoazo compounds and their use as disperse dyes |
JPS62115070A (ja) * | 1985-11-09 | 1987-05-26 | カセラ・アクチエンゲゼルシヤフト | 青色分散染料の混合物 |
JP2014516390A (ja) * | 2011-04-20 | 2014-07-10 | ハンツマン アドバンスト マテリアルズ (スイッツァランド) ゲーエムベーハー | ポリエステルの染色方法 |
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FR2008404A1 (en) | 1968-05-13 | 1970-01-23 | Eastman Kodak Co | Insoluble monoazo dyes for polyester fibres |
JPH0762258A (ja) * | 1993-08-26 | 1995-03-07 | Sumitomo Chem Co Ltd | ベンゾジフラノン含有赤色着色性組成物及びそれを用いる疎水性材料の着色方法 |
KR100356768B1 (ko) | 1994-04-19 | 2003-09-02 | 니폰 가야꾸 가부시끼가이샤 | 분산염료조성물및이를사용한소수성섬유물질의염색방법 |
GB9809454D0 (en) * | 1998-05-01 | 1998-07-01 | Basf Ag | Disperse dye mixture |
GB0130316D0 (en) * | 2001-12-19 | 2002-02-06 | Clariant Int Ltd | Composition for printing recording materials |
JP2010533751A (ja) | 2007-07-20 | 2010-10-28 | ハンツマン アドバンスト マテリアルズ (スイッツァランド) ゲーエムベーハー | アゾ染料 |
CN101955691B (zh) | 2010-08-26 | 2013-12-25 | 浙江龙盛集团股份有限公司 | 一种分散深蓝染料组合物 |
CN102732056B (zh) * | 2012-06-01 | 2013-09-11 | 浙江吉华集团股份有限公司 | 一种分散染料混合物及其应用 |
US9376570B2 (en) | 2012-07-27 | 2016-06-28 | Huntsman International Llc | Disperse azo dyes, a process for the preparation thereof and the use thereof |
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GB1275603A (en) * | 1968-05-13 | 1972-05-24 | Eastman Kodak Co | Monoazo compounds and their use as disperse dyes |
JPS62115070A (ja) * | 1985-11-09 | 1987-05-26 | カセラ・アクチエンゲゼルシヤフト | 青色分散染料の混合物 |
JP2014516390A (ja) * | 2011-04-20 | 2014-07-10 | ハンツマン アドバンスト マテリアルズ (スイッツァランド) ゲーエムベーハー | ポリエステルの染色方法 |
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