TWI830702B - 分散偶氮染料 - Google Patents
分散偶氮染料 Download PDFInfo
- Publication number
- TWI830702B TWI830702B TW107121909A TW107121909A TWI830702B TW I830702 B TWI830702 B TW I830702B TW 107121909 A TW107121909 A TW 107121909A TW 107121909 A TW107121909 A TW 107121909A TW I830702 B TWI830702 B TW I830702B
- Authority
- TW
- Taiwan
- Prior art keywords
- disperse blue
- dye
- formula
- disperse
- dyes
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000004043 dyeing Methods 0.000 claims abstract description 19
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 17
- -1 bromo, nitro, cyano, methyl Chemical group 0.000 claims abstract description 16
- 238000007639 printing Methods 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 239000000835 fiber Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 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 23
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 claims description 22
- 239000002657 fibrous material Substances 0.000 claims description 19
- 229920000728 polyester Polymers 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 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
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- ZRLYFONGBAKSBB-OFWBYEQRSA-N 2-[(2z)-2-[[4-(dihexylamino)-2-methylphenyl]methylidene]-1,1-dioxo-1-benzothiophen-3-ylidene]propanedinitrile Chemical compound CC1=CC(N(CCCCCC)CCCCCC)=CC=C1\C=C\1S(=O)(=O)C2=CC=CC=C2C/1=C(C#N)C#N ZRLYFONGBAKSBB-OFWBYEQRSA-N 0.000 claims description 2
- 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
- WBCXRDHKXHADQF-UHFFFAOYSA-N 4,11-diamino-2-(3-methoxypropyl)naphtho[2,3-f]isoindole-1,3,5,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(N(CCCOC)C1=O)=O)C1=C2N WBCXRDHKXHADQF-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 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
- 239000000975 dye Substances 0.000 abstract description 55
- 239000000463 material Substances 0.000 abstract description 13
- 239000004753 textile Substances 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 4
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000010016 exhaust dyeing Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004744 fabric Substances 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
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- 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
- 244000215068 Acacia senegal Species 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 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
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- 229920001612 Hydroxyethyl starch Polymers 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
- 229920001615 Tragacanth Polymers 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 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
- 238000000889 atomisation Methods 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
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 150000001989 diazonium salts Chemical class 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
- 235000013312 flour Nutrition 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
- 239000012943 hotmelt Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000007641 inkjet printing 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
- 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
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
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
- 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
-
- 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
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
本發明係關於下式分散偶氮染料
其中R1為溴、硝基、氰基、甲基、甲氧基或三氟甲基；R2為氫、氯、溴或三氟甲基；R3為氫、氯、溴、甲氧基、三氟甲基、硝基或氰基；且R4為甲基、乙基、正丙基、2-甲氧基乙基、甲氧基羰基甲基或2-甲氧基羰基乙基；其限制條件為在R2表示氯或溴的情況下R1為氰基，本發明亦關於一種製備此類染料之方法及此類染料在半合成且尤其是合成的疏水性纖維材料，更尤其是紡織材料的染色或印花中之用途。
Description
本發明係關於具有經乙醯胺基取代之苯胺偶合組分的分散染料、製備此類染料的方法及此類染料在半合成且尤其是合成的疏水性纖維材料、更尤其是紡織材料的染色或印花之用途。
衍生自硝基苯胺重氮組分及乙醯胺基苯胺偶合組分的分散偶氮染料早已為公眾所知，例如從FR 2008404知曉，且被用於疏水性纖維材料的染色。然而發現，使用目前已知之染料獲得的染色或印花並非在所有情況下都能滿足當前要求，尤其是在其耐光堅牢度、耐洗堅牢度及耐汗漬堅牢度特性方面。尤其在藍色染料領域中，需要能夠給出具有良好的耐光堅牢度、耐洗堅牢度及耐汗漬堅牢度特性的具有明亮色澤的染色的新染料。
現已意外發現，根據本發明之染料在很大程度上滿足以上所提及之準則。
因此，本發明係關於分散染料，其能產生具有極佳的耐光堅牢度、耐洗堅牢度及耐汗漬堅牢度的染色物，且另外在竭染法(exhaust process)及熱熔染色法(thermosol process)及在織物印花均展現良好積色(build-up)。
根據本發明之染料對應於下式
其中R1為溴、硝基、氰基、甲基、甲氧基或三氟甲基；R2為氫、氯、溴或三氟甲基；R3為氫、氯、溴、甲氧基、三氟甲基、硝基或氰基；且R4為甲基、乙基、正丙基、2-甲氧基乙基、甲氧基羰基甲基或2-甲氧基羰基乙基；其限制條件為，在R2表示氯或溴的情況下R1為氰基，且在R2表示三氟甲基的情況下R1為氰基或硝基。
在式(1)中，R1較佳為氰基。
其中R2為氯的式(1)染料更佳。
其中R3為氫的式(1)染料特佳。
式(1)中之R4較佳為甲基、乙基、甲氧基羰基甲基或2-甲氧基羰基乙基。
本發明亦關於一種製備如上文所定義之式(1)染料的方法，其包含使下式化合物重氮化
及使由此獲得之重氮化合物偶合至下式偶合組分
其中R1、R2、R3及R4具有上文關於式(1)所給出之含義。
式(2)之重氮組分以及式(3)之偶合組分係已知的或可以本身已知的方式製備。一些是市售的。
重氮化以本身已知的方式進行，例如採用亞硝酸鈉，在酸性，例如含鹽酸或含硫酸的水性介質中。然而，重氮化亦可以使用其他重氮化劑進行，例如使用亞硝基硫酸。在重氮化時，在反應介質中可能存在額外的酸，例如磷酸、硫酸、乙酸、丙酸或鹽酸或該等酸之混合物，例如丙酸與乙酸之混合物。重氮化有利地在-10℃至30℃，例如-10℃至室溫之溫度下進行。
經重氮化之化合物與式(3)之偶合組分的偶合同樣以已知方式進行，例如在酸性、水性或水性有機介質中，有利地在-10至30℃，尤其是低於10℃之溫度下。所用酸之實例為鹽酸、乙酸、丙酸、硫酸及磷酸。
本發明另外關於一種染料混合物，其包含至少一種如上文所定義之式(1)染料及至少一種選自由以下組成之群的其他染料：C.I.分散藍60、C.I.分散藍79：1、C.I.分散藍72：2、C.I.分散藍148、C.I.分散藍149、C.I.分散藍165、C.I.分散藍165：1、C.I.分散藍207、C.I.分散藍284、C.I.分散藍295、C.I.分散藍316、C.I.分散藍337、C.I.分散藍354、C.I.分散藍366、C.I.分散藍367、C.I.分散藍368、C.I.分散藍376、C.I.分散藍378、C.I.分散藍380、C.I.分散綠9、C.I.分散紫107、WO 2014/016072中所述之式(101)至式(179)之化合物、WO 2009/013122中所述之式(101)至式(106)之化合物及CN 101955691中所述之式II-2、式II-3、式II-4及式III-1至式III-8之化合物。
根據本發明之染料混合物可例如藉由簡單地混合個別染料來製備。
根據本發明之染料混合物中之個別染料之量可以在一個寬範圍內變化。
根據本發明之染料混合物有利地含有至少20重量%、較佳至少30重量%且尤其至少40重量%的一或多種式(1)染料。
根據本發明之染料及染料混合物可用於半合成且尤其合成的疏水性纖維材料、更尤其是紡織材料的染色或印花。由含有此類半合成及/或合成的疏水性纖維材料的混合物構成的紡織材料同樣可以使用根據本發明之染料或染料混合物染色或印花。
可考慮的半合成纖維材料尤其為2½乙酸纖維素及三乙酸纖維素。
合成疏水性纖維材料尤其由以下各者組成：線性芳族聚酯(例如對苯二甲酸)及二醇(尤其乙二醇)，或對苯二甲酸與1,4-雙(羥基甲基)環己烷之縮合產物；聚碳酸酯，例如α,α-二甲基-4,4-二羥基-二苯基甲烷及光氣之聚碳酸酯；及基於聚氯乙烯或聚醯胺之纖維。
根據本發明之染料及染料混合物於纖維材料之應用根據已知染色程序實現。舉例而言，在慣用陰離子或非離子分散劑及視情況選用之慣用膨潤劑(載體)存在下，在80℃至140℃之溫度下，在竭染法中自水性分散液對聚酯纖維材料進行染色。2½乙酸纖維素較佳在65℃至85℃下染色，且三乙酸纖維素在65℃至115℃之溫度下染色。
根據本發明之染料及染料混合物不會使同時存在於染浴中之羊毛及棉著色，或使此類材料僅稍微著色(極佳防染(reservation))，以使得其亦可令人滿意地用於聚酯/羊毛及聚酯/纖維素纖維混紡織物的染色。
根據本發明之染料及染料混合物適合於根據熱熔染色法、竭染法及印花法染色，印花法如網版印花或噴墨印花。
該等纖維材料可呈多種加工形式，例如呈纖維、紗線或非織物形式，呈編織物或針織物形式。
在使用前將根據本發明之染料及染料混合物轉化成染料製劑係有利的。出於此目的，研磨染料，以使其粒度平均為0.1微米至10微米。研磨可在分散劑存在下進行。舉例而言，經乾燥之染料與分散劑一起研磨或以糊料形式與分散劑揉合，且隨後在真空中或藉由霧化乾燥。由此獲得之製劑可以在添加水之後使用以製備印花糊料及染浴。
關於印花，將使用慣用增稠劑，例如經改質或未改質之天然產物，例如海藻酸鹽、大英粉(British gum)、阿拉伯膠(gum arabic)、結晶膠、刺槐豆粉、黃蓍、羧甲基纖維素、羥乙基纖維素、澱粉或合成產物，例如聚丙烯醯胺、聚丙烯酸或其共聚物或聚乙烯醇。
根據本發明之染料及染料混合物賦予該等所提及之材料、尤其是聚酯材料具有極佳的使用堅牢度特性的均勻色澤，該等特性尤其諸如良好的耐光堅牢度、耐熱固著(thermofixing)堅牢度、耐褶堅牢度、耐氯堅牢度及耐濕堅牢度，例如耐水堅牢度、耐汗漬堅牢度及耐洗堅牢度；成品染色亦以極佳的耐摩擦堅牢度著稱。應該特別提及所得染色有良好的耐光堅牢度、耐汗漬堅牢度且尤其是耐洗堅牢度特性。
根據本發明之染料及染料混合物亦可連同其他染料一起用於製備混合色澤，結果令人滿意。
根據本發明之染料及染料混合物亦非常適合自超臨界CO2對疏水性纖維材料進行染色。
本發明亦關於以上提及之根據本發明之染料及染料混合物的用途以及對半合成或合成的疏水性纖維材料、尤其是紡織材料進行染色或印花的方法，其中將根據本發明之染料施加至該等材料或摻入彼等材料中。該等疏水 性纖維材料較佳為紡織聚酯材料。可用根據本發明之方法以及較佳製程條件處理的其他基材可見於上文根據本發明之染料之用途的詳細說明中。
本發明亦關於藉由該方法染色或印花之疏水性纖維材料，尤其是聚酯紡織材料。
根據本發明之染料亦適合現代再現法(modern reproduction process)，例如熱轉移印花。
以下實施例用於說明本發明。在實施例中，除非另有指示，否則份數係重量份且百分比係重量百分比。溫度以攝氏度為單位給出。重量份與體積份之間的關係與公克與立方公分之間的關係相同。
RT=室溫
I.製備實施例
實施例I.1
A.重氮化
將20g濃硫酸置放於實驗室反應設備中。在添加5g冰之後，將溶液冷卻至室溫。在此溫度下，添加6.01g 2-溴-4-硝基-6-氰基苯胺。在室溫下攪拌30分鐘且冷卻至10℃之後，逐滴添加8.2g 40%亞硝基硫酸。將反應混合物在10℃下再攪拌60分鐘。隨後，藉由添加胺磺酸來消滅過量亞硝酸鹽。
B.偶合
將根據FR 2008404之實施例1a中所述之方法製備的7.83g細粉狀 N-3-硝基苯甲基-N-乙基-3-乙醯胺基苯胺懸浮於10ml乙醇中且與20g冰混合。
在攪拌下，在60分鐘內逐滴添加在步驟A中所獲得的之重氮鹽溶液。在室溫下攪拌混合物隔夜。在過濾、洗滌及乾燥之後，獲得11.75g(83%)式(101)染料。
表1中所列出之染料(102)至(1252)以類似於實施例I.1中所述之方法製備。
II.應用實施例
II.1：聚酯之染色
將1重量份在實施例I.1中製備之式(101)染料與四份市售分散劑及15份水一起碾磨。使用彼調配物，在135℃下藉由高溫竭染法，在編織聚酯上產生1%染色(以染料及基材計)。
測試結果：染色之耐光堅牢度極佳，AATCC 61及ISO 105測試 之結果同樣極佳。染料之積色特性極佳。
Claims (10)
- 一種式(1)染料，其具有以下結構式：
- 如請求項1所述之式(1)染料，其中R3為氫。
- 如請求項1或2所述之式(1)染料，其中R4為甲基、乙基、甲氧基羰基甲基或2-甲氧基羰基乙基。
- 一種製備如請求項1所述之式(1)染料的方法，其包含使下式化合物重氮化
- 一種染料混合物，其包含至少一種如請求項1所述之式(1)染料及至少一種選自由以下組成之群的其他染料：C.I.分散藍60、C.I.分散藍79：1、C.I.分散藍72：2、C.I.分散藍148、C.I.分散藍149、C.I.分散藍165、C.I.分散藍165：1、C.I.分散藍207、C.I.分散藍284、C.I.分散藍295、C.I.分散藍316、C.I.分散藍337、C.I.分散藍354、C.I.分散藍366、C.I.分散藍367、C.I.分散藍368、C.I.分散藍376、C.I.分散藍378、C.I.分散藍380、C.I.分散綠9及C.I.分散紫107。
- 一種對半合成或合成的疏水性纖維材料進行染色的方法，其包含向該疏水性纖維材料施加或摻入至少一種如請求項1所述之式(1)染料或如請求項5所述之染料混合物。
- 如請求項6所述之方法，其中該疏水性纖維材料含有聚酯纖維。
- 一種對半合成或合成的疏水性纖維材料進行印花的方法，其包含向該疏水性纖維材料施加或摻入至少一種如請求項1所述之式(1)染料或如請求項5所述之染料混合物。
- 如請求項8所述之方法，其中該疏水性纖維材料含有聚酯纖維。
- 一種疏水性纖維材料，其根據請求項6至9中任一項所述之方法染色或印花。
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| US11479912B2 (en) | 2022-10-25 |
| EP3645632B1 (en) | 2023-03-29 |
| CN110770304A (zh) | 2020-02-07 |
| US20200199813A1 (en) | 2020-06-25 |
| WO2019001832A1 (en) | 2019-01-03 |
| JP2020525580A (ja) | 2020-08-27 |
| PT3645632T (pt) | 2023-04-20 |
| BR112019026104A8 (pt) | 2023-05-09 |
| MX2019014471A (es) | 2020-01-23 |
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