CN110770304A - 分散性偶氮染料 - Google Patents
分散性偶氮染料 Download PDFInfo
- Publication number
- CN110770304A CN110770304A CN201880043790.8A CN201880043790A CN110770304A CN 110770304 A CN110770304 A CN 110770304A CN 201880043790 A CN201880043790 A CN 201880043790A CN 110770304 A CN110770304 A CN 110770304A
- Authority
- CN
- China
- Prior art keywords
- disperse blue
- formula
- dye
- disperse
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000000987 azo dye Substances 0.000 title description 3
- 239000000463 material Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000004043 dyeing Methods 0.000 claims abstract description 17
- -1 nitro, cyano, methyl Chemical group 0.000 claims abstract description 16
- 239000000835 fiber Substances 0.000 claims abstract description 14
- 239000000460 chlorine Substances 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 238000007639 printing Methods 0.000 claims abstract description 9
- 239000004753 textile Substances 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([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 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000001309 chloro group Chemical group Cl* 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
- 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
- 239000000203 mixture Substances 0.000 claims description 22
- 229920000728 polyester Polymers 0.000 claims description 11
- 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
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 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
- 238000004519 manufacturing process Methods 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
- 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 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 50
- 238000002360 preparation method Methods 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000009472 formulation Methods 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
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate 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
- 239000000243 solution Substances 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
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 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
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose 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
- 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 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
- 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
- 239000000969 carrier Substances 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
- 239000013078 crystal Substances 0.000 description 1
- 235000019425 dextrin Nutrition 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002009 diols 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
- 238000009998 heat setting Methods 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000003801 milling Methods 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
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 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
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000010076 replication Effects 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
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037303 wrinkles Effects 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
本发明涉及具有式(1)：
的分散性偶氮染料，其中R1是溴、硝基、氰基、甲基、甲氧基或三氟甲基；R2是氢、氯、溴或三氟甲基；R3是氢、氯、溴、甲氧基、三氟甲基、硝基或氰基；并且R4是甲基、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；条件是在R2表示氯或溴的情况下R1是氰基，涉及制备此类染料的方法及其在半合成、特别是合成疏水性纤维材料、更特别是纺织材料的染色或印刷中的用途。
Description
本发明涉及具有乙酰氨基取代的苯胺偶联组分的分散性染料、制备这样的染料的方法及其在半合成、特别是合成疏水性纤维材料、更特别是纺织材料的染色或印刷中的用途。
由硝基苯胺重氮组分和乙酰氨基苯胺偶联组分获得的分散性偶氮染料早已为人所知(例如FR 2008404)并被用于疏水性纤维材料的染色。然而，已经发现使用目前已知的染料获得的染色品或印刷品并非在所有情况下都满足当前的要求，特别是在耐光牢度、耐洗牢度和耐汗渍牢度特性方面。特别地，在蓝色染料领域中，需要产生明亮色泽的染色品的新染料，该染色品具有良好的耐光牢度、耐洗牢度和耐汗渍牢度特性。
令人惊讶的是，现已发现根据本发明的染料在很大程度上满足上述标准。
因此，本发明涉及产生具有非常好的耐光牢度、耐洗牢度和耐汗渍牢度的染色品并且另外在尽染和热溶工艺以及纺织品印刷中均显示出良好的提升性(build-up)的分散性染料。
根据本发明的染料对应于式：
其中：
R1是溴、硝基、氰基、甲基、甲氧基或三氟甲基；
R2是氢、氯、溴或三氟甲基；
R3是氢、氯、溴、甲氧基、三氟甲基、硝基或氰基；并且
R4是甲基、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；
条件是在R2表示氯或溴的情况下R1是氰基以及在R2表示三氟甲基的情况下R1是氰基或硝基。
在式(1)中，R1优选是氰基。
进一步优选地，在式(1)的染料中，R2是氯。
特别优选地，在式(1)的染料中，R3是氢。
在式(1)中，R4优选是甲基、乙基、甲氧基羰基甲基或2-甲氧基羰基乙基。
本发明还涉及制备如上定义的式(1)的染料的方法，所述方法包括将式：
其中R1、R2、R3和R4具有如上对式(1)给出的含义。
式(2)的重氮组分以及式(3)的偶联组分是已知的或可以以本身已知的方式制备。一些是可商购的。
所述重氮化以本身已知的方式进行，例如在酸性，例如含盐酸或含硫酸的水性介质中使用亚硝酸钠进行。然而，所述重氮化也可以使用其他重氮化剂，例如使用亚硝基硫酸进行。在所述重氮化中，在反应介质中可以存在另外的酸，例如磷酸、硫酸、乙酸、丙酸或盐酸或此类酸的混合物，例如丙酸和乙酸的混合物。所述重氮化有利地在-10℃至30℃、例如-10℃至室温的温度下进行。
将重氮化化合物偶联至式(3)的偶联组分同样以已知的方式进行，例如在酸性、水性或水性-有机介质中，有利地在-10℃至30℃、特别是低于10℃的温度下进行。所用酸的实例是盐酸、乙酸、丙酸、硫酸和磷酸。
本发明还涉及染料混合物，其包含至少一种如上定义的式(1)的染料和至少一种另外的染料，所述另外的染料选自C.I.分散蓝60、C.I.分散蓝79：1，C.I.分散蓝72：2、C.I.分散蓝148、C.I.分散蓝149、C.I.分散蓝165、C.I.分散蓝165：1、C.I.分散蓝207、C.I.分散蓝284、C.I.分散蓝295、C.I.分散蓝316、C.I.分散蓝337、C.I.分散蓝354、C.I.分散蓝366、C.I.分散蓝367、C.I.分散蓝368、C.I.分散蓝376、C.I.分散蓝378、C.I.分散蓝380、C.I.分散绿9、C.I.分散紫107、WO 2014/016072中描述的式(101)至(179)的化合物、WO 2009/013122中描述的式(101)至(106)的化合物以及CN 101955691中描述的式II-2、II-3、II-4和III-1至III-8的化合物。
根据本发明的染料混合物可以例如通过简单地混合各染料来制备。
根据本发明的染料混合物中的各染料的量可以在宽范围内变化。
根据本发明的染料混合物有利地包含至少20重量％、优选至少30重量％、特别是至少40重量％的一种或多种式(1)的染料。
根据本发明的染料和染料混合物可以用于半合成、特别是合成疏水性纤维材料、更特别是纺织材料的染色或印刷。由包含此类半合成和/或合成疏水性纤维材料的共混物组成的纺织材料同样可以使用根据本发明的染料或染料混合物来染色或印刷。
考虑的半合成纤维材料特别是二倍半乙酸纤维素和三乙酸纤维素。
合成疏水性纤维材料特别包括直链芳族聚酯，例如对苯二甲酸和二醇、特别是乙二醇形成的聚酯，或对苯二甲酸与1,4-双(羟甲基)环己烷的缩合产物；聚碳酸酯，例如α,α-二甲基-4,4-二羟基-二苯基甲烷和光气形成的聚碳酸酯，以及基于聚氯乙烯和基于聚酰胺的纤维。
将根据本发明的染料和染料混合物施加至纤维材料根据已知的染色方法来实施。例如，在尽染工艺中，在常规的阴离子或非离子分散剂和任选的常规溶胀剂(载体)的存在下在80-140℃的温度下由水性分散体将聚酯纤维材料染色。优选将二倍半乙酸纤维素在65-85℃下染色，将三乙酸纤维素在65-115℃下染色。
根据本发明的染料和染料混合物不会使同时存在于染浴中的羊毛和棉花着色，或者只会使此类材料略微着色(非常好的防染性)，因此它们也可以令人满意地用于聚酯/羊毛和聚酯/纤维素纤维混纺织物的染色中。
根据本发明的染料和染料混合物适合于根据热溶工艺、尽染工艺进行的染色以及适合于印刷工艺诸如丝网印刷或喷墨印刷。
所述纤维材料可以为多种加工形式，例如纤维、纱线或无纺织物的形式、机织织物或针织织物的形式。
在使用前将根据本发明的染料和染料混合物转变为染料配制物是有利的。为此目的，将所述染料研磨，以使其平均粒度为0.1-10微米。所述研磨可以在分散剂的存在下进行。例如，将干燥的染料与分散剂一起研磨或与分散剂一起以糊料形式捏合，然后在真空中或通过雾化干燥。如此获得的配制物可以在添加水之后用于制备印刷糊料和染浴。
对于印刷而言，将使用常规的增稠剂，例如改性或未改性的天然产物，例如藻酸盐、糊精、阿拉伯树胶、结晶树胶、刺槐豆粉、黄蓍胶、羧甲基纤维素、羟乙基纤维素、淀粉或合成产物，例如聚丙烯酰胺、聚丙烯酸或其共聚物、或聚乙烯醇。
根据本发明的染料和染料混合物对所提及的材料、特别是聚酯材料赋予具有非常好的使用牢度特性、例如特别是良好的耐光牢度、耐热定型牢度、耐褶皱牢度、耐氯漂牢度和耐湿牢度、例如耐水牢度、耐汗渍牢度和耐洗牢度的均匀色泽(level colour shades)；最终的染色品还具有很好的耐摩擦牢度。应特别提及所得染色品具有良好的耐光牢度、耐汗渍牢度、特别是耐洗牢度的特性。
根据本发明的染料和染料混合物还可以令人满意地用于与其他染料一起制备混合色泽。
根据本发明的染料和染料混合物也非常适合用于从超临界CO2使疏水性纤维材料染色。
本发明还涉及根据本发明的染料和染料混合物的上述用途，以及将半合成或合成疏水性纤维材料、特别是纺织材料染色或印刷的方法，其中，将根据本发明的染料施加至所述材料或并入所述材料中。所述疏水性纤维材料优选是纺织聚酯材料。可以通过根据本发明的方法处理的其他基材以及优选的工艺条件可以见于上文中根据本发明的染料的用途的详细描述。
本发明还涉及通过所述方法染色或印刷的疏水性纤维材料，特别是聚酯纺织材料。
根据本发明的染料也适用于现代复制方法，例如热转印。
以下实施例用于举例说明本发明。在实施例中，除非另有说明，否则份是重量份，百分数是重量百分数。温度以摄氏度给出。重量份和体积份之间的关系与克和立方厘米之间的关系相同。
RT =室温。
I.制备实施例
实施例I.1
A.重氮化
将20g的浓硫酸置于实验室反应设备中。加入5g冰后，将溶液冷却至室温。在此温度下，加入6.01g的2-溴-4-硝基-6-氰基苯胺。在室温下搅拌30分钟并冷却至10℃后，逐滴添加8.2g的40％亚硝基硫酸。将反应混合物在10℃下再搅拌60分钟。之后，通过添加氨基磺酸破坏过量的亚硝酸盐。
B.偶联
将7.83g的根据FR 2008404的实施例1a中描述的方法制备的粉末状N-3-硝基苄基-N-乙基-3-乙酰氨基苯胺悬浮在10ml乙醇中，并与20g冰混合。
在搅拌下，在60分钟内逐滴添加步骤A中获得的重氮盐溶液。将反应混合物在室温下搅拌过夜。在过滤、洗涤并干燥后，获得11.75g(83％)的式(101)的染料。
表1中所列的染料(102)至(1252)的制备类似于实施例I.1中所述的方法。
表1：
(λmax =吸收最大波长)
II.应用实施例
II.1：聚酯的染色
将1重量份的实施例I.1中制备的式(101)的染料与四份市售分散剂和15份水一起研磨。使用该配方，通过在135℃下的高温尽染工艺在聚酯织物上产生1％的染色(基于染料和基材)。
测试结果：该染色品的耐光性以及AATCC 61测试和ISO 105测试的结果都优异。染料的提升性非常好。
Claims (10)
1.下式的染料：
其中：
R1是溴、硝基、氰基、甲基、甲氧基或三氟甲基；
R2是氢、氯、溴或三氟甲基；
R3是氢、氯、溴、甲氧基、三氟甲基、硝基或氰基；并且
R4是甲基、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；
条件是在R2表示氯或溴的情况下R1是氰基以及在R2表示三氟甲基的情况下R1是氰基或硝基。
2.根据权利要求1的式(1)的染料，其中R1是氰基。
3.根据权利要求1或2的式(1)的染料，其中R2是氯。
4.根据权利要求1-3中任一项的式(1)的染料，其中R3是氢。
5.根据权利要求1-4中任一项的式(1)的染料，其中R4是甲基、乙基、甲氧基羰基甲基或2-甲氧基羰基乙基。
6.制备根据权利要求1的式(1)的染料的方法，所述方法包括将式：
的化合物重氮化，并将由此获得的重氮化合物与式：
其中R1、R2、R3和R4具有如权利要求1中对式(1)给出的含义。
7.染料混合物，其包含至少一种根据权利要求1的式(1)的染料和至少一种另外的染料，所述另外的染料选自C.I.分散蓝60、C.I.分散蓝79：1，C.I.分散蓝72：2、C.I.分散蓝148、C.I.分散蓝149、C.I.分散蓝165、C.I.分散蓝165：1、C.I.分散蓝207、C.I.分散蓝284、C.I.分散蓝295、C.I.分散蓝316、C.I.分散蓝337、C.I.分散蓝354、C.I.分散蓝366、C.I.分散蓝367、C.I.分散蓝368、C.I.分散蓝376、C.I.分散蓝378、C.I.分散蓝380、C.I.分散绿9、C.I.分散紫107、WO 2014/016072中描述的式(101)至(179)的化合物、WO 2009/013122中描述的式(101)至(106)的化合物以及CN 101955691中描述的式II-2、II-3、II-4和III-1至III-8的化合物。
8.将半合成或合成疏水性纤维材料，特别是纺织材料染色或印刷的方法，所述方法包括将至少一种根据权利要求1的式(1)的染料或根据权利要求7的染料混合物施加至所述材料或并入所述材料中。
9.根据权利要求8的方法，其中所述疏水性材料，优选纺织材料包括聚酯纤维。
10.根据权利要求8或权利要求9染色或印刷的材料。
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| GB1275603A (en) * | 1968-05-13 | 1972-05-24 | Eastman Kodak Co | Monoazo compounds and their use as disperse dyes |
| US4678476A (en) * | 1985-11-09 | 1987-07-07 | Cassella Aktiengesellschaft | Mixtures of blue mono-azo disperse dyestuffs and their use for dyeing polyester |
| CN103502528A (zh) * | 2011-04-20 | 2014-01-08 | 亨斯迈先进材料（瑞士）有限公司 | 聚酯染色方法 |
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| Publication number | Publication date |
|---|---|
| KR102698054B1 (ko) | 2024-08-26 |
| MY200716A (en) | 2024-01-12 |
| US11479912B2 (en) | 2022-10-25 |
| TWI830702B (zh) | 2024-02-01 |
| PT3645632T (pt) | 2023-04-20 |
| KR20200024233A (ko) | 2020-03-06 |
| JP2020525580A (ja) | 2020-08-27 |
| EP3645632B1 (en) | 2023-03-29 |
| WO2019001832A1 (en) | 2019-01-03 |
| BR112019026104A2 (pt) | 2020-06-30 |
| TW201905105A (zh) | 2019-02-01 |
| US20200199813A1 (en) | 2020-06-25 |
| MX2019014471A (es) | 2020-01-23 |
| ES2943652T3 (es) | 2023-06-15 |
| BR112019026104A8 (pt) | 2023-05-09 |
| EP3645632A1 (en) | 2020-05-06 |
| PL3645632T3 (pl) | 2023-07-31 |
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