CN103249780A - 分散性偶氮染料 - Google Patents
分散性偶氮染料 Download PDFInfo
- Publication number
- CN103249780A CN103249780A CN2011800611207A CN201180061120A CN103249780A CN 103249780 A CN103249780 A CN 103249780A CN 2011800611207 A CN2011800611207 A CN 2011800611207A CN 201180061120 A CN201180061120 A CN 201180061120A CN 103249780 A CN103249780 A CN 103249780A
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- formula
- trifluoromethyl
- hydrogen
- fluorine
- 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.)
- Granted
Links
- 239000000987 azo dye Substances 0.000 title abstract 2
- 239000000975 dye Substances 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000004043 dyeing Methods 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 20
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- 230000008878 coupling Effects 0.000 claims abstract description 11
- 238000010168 coupling process Methods 0.000 claims abstract description 11
- 238000005859 coupling reaction Methods 0.000 claims abstract description 11
- 238000007639 printing Methods 0.000 claims abstract description 10
- 239000004753 textile Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 239000002657 fibrous material Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006193 diazotization reaction Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000006606 n-butoxy group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- -1 2,6-diaminosubstituted pyridine Chemical class 0.000 abstract description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 5
- 239000000835 fiber Substances 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000006243 chemical reaction Methods 0.000 description 4
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 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
- MBSASSANIQDGOD-UHFFFAOYSA-N 2,5-diamino-4-methyl-6-phenylpyridine-3-carbonitrile Chemical compound NC1=NC(=C(C(=C1C#N)C)N)C1=CC=CC=C1 MBSASSANIQDGOD-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- PLAWCFOMHQCJBK-UHFFFAOYSA-N 1-(2,2-dimethylpropylperoxy)pentane Chemical compound CCCCCOOCC(C)(C)C PLAWCFOMHQCJBK-UHFFFAOYSA-N 0.000 description 1
- DVCMHLZPRDGHKK-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(2-methoxyethoxy)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCCOC)=CC(O)=C3C(=O)C2=C1 DVCMHLZPRDGHKK-UHFFFAOYSA-N 0.000 description 1
- RQLMZSLFKGNXTO-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(6-hydroxyhexoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCCCCCO)=C2N RQLMZSLFKGNXTO-UHFFFAOYSA-N 0.000 description 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- FEJPWLNPOFOBSP-UHFFFAOYSA-N 2-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-ethylanilino]ethanol Chemical compound C1=CC(N(CCO)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl FEJPWLNPOFOBSP-UHFFFAOYSA-N 0.000 description 1
- ROPYWXVRNREIQD-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ROPYWXVRNREIQD-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BCLCKENDTZITFB-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)aniline Chemical compound CC1=CC=C(C(F)(F)F)C=C1N BCLCKENDTZITFB-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AIARLPIXVMHZLJ-UHFFFAOYSA-N 4,8-diamino-2-bromo-1,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=C(Br)C(O)=C2C(=O)C2=C1C(O)=CC=C2N AIARLPIXVMHZLJ-UHFFFAOYSA-N 0.000 description 1
- ALXCWDABTQQKAH-UHFFFAOYSA-N 4-(1-amino-4-hydroxy-9,10-dioxoanthracen-2-yl)oxy-n-(3-ethoxypropyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCCOCC)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N ALXCWDABTQQKAH-UHFFFAOYSA-N 0.000 description 1
- PMDYLCUKSLBUHO-UHFFFAOYSA-N 4-amino-2-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C#N)C(C(F)(F)F)=C1 PMDYLCUKSLBUHO-UHFFFAOYSA-N 0.000 description 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
- BBFRYSKTTHYWQZ-UHFFFAOYSA-N 4-anilino-3-nitro-n-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC=2C=CC=CC=2)=CC=C1NC1=CC=CC=C1 BBFRYSKTTHYWQZ-UHFFFAOYSA-N 0.000 description 1
- CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- JBCDCYFEJQHTTA-UHFFFAOYSA-N 4-methyl-3-(trifluoromethyl)aniline Chemical compound CC1=CC=C(N)C=C1C(F)(F)F JBCDCYFEJQHTTA-UHFFFAOYSA-N 0.000 description 1
- XCKGFJPFEHHHQA-UHFFFAOYSA-N 5-methyl-2-phenyl-4-phenyldiazenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC=C1 XCKGFJPFEHHHQA-UHFFFAOYSA-N 0.000 description 1
- XDWUSBKLDNVDDQ-UHFFFAOYSA-N 6-phenylpyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=N1 XDWUSBKLDNVDDQ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 240000008886 Ceratonia siliqua Species 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
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 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
- 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 1
- GTZOZDOTOWNSJH-UHFFFAOYSA-N [O].CCCCCCC Chemical compound [O].CCCCCCC GTZOZDOTOWNSJH-UHFFFAOYSA-N 0.000 description 1
- CVYNBVMJLPTTFD-UHFFFAOYSA-N [O].CCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCC CVYNBVMJLPTTFD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- BXIGAWRFDMDLTL-UHFFFAOYSA-N n-(4-amino-3-methoxy-9,10-dioxoanthracen-1-yl)-4-methylbenzenesulfonamide Chemical compound C=12C(=O)C3=CC=CC=C3C(=O)C2=C(N)C(OC)=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 BXIGAWRFDMDLTL-UHFFFAOYSA-N 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及基于具有至少一个含氟取代基的偶氮组分和2,6-二氨基取代的吡啶偶合组分的分散性偶氮染料、制备所述染料的方法及其在半合成且特别是合成的疏水性纤维材料、更特别是纺织材料的染色或印刷中的用途。
Description
本发明涉及基于具有至少一个含氟取代基的偶氮组分的分散性染料、制备所述染料的方法及其在半合成且特别是合成的疏水性纤维材料、更特别是纺织材料的染色或印刷中的用途。
早就已知具有苯胺偶氮组分和2,6-二氨基取代的吡啶偶合组分的分散性偶氮染料且将其用于疏水性纤维材料的染色中。然而,发现使用目前已知的染料得到的染色品或印刷品并非在所有情况下都满足汽车工业的现行要求,特别是在其耐光牢度性质,尤其是其耐热光牢度方面。
现在已经惊奇地发现根据本发明的染料在很大程度上满足上述标准。
本发明因此涉及产生具有很好的耐光牢度的染色品且另外在浸染和热溶过程中及在织物印刷中都显示出良好的累积的分散性染料。
根据本发明的染料对应于下式:
其中R1为氟、三氟甲基、三氟甲氧基或三氟甲基磺酰基,
R2和R3各自彼此独立地代表氢、C1-C12烷基、C1-C12烷氧基、卤素、氰基、硝基、三氟甲基或-COOR6,其中R6为未被取代或被一个或多个C1-C12烷氧基、羟基、氨基或卤素原子取代的C1-C12烷基,
R4和R5表示氢或未被取代或被一个或多个C1-C12烷基、C1-C12烷氧基或三氟甲基取代的苯基,
其限制条件为基团R4和R5中的一个为氢且另一个为未被取代或被取代的苯基,
且其限制条件为,如果R1代表在偶氮基邻位上的三氟甲基,则R2和R3中的至少一个不为氢。
当基团R1、R2或R6中的任一个或者R4或R5的取代基中的任一个为烷基时,所述(一个或多个)烷基可为直链或支链的。烷基的实例有甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、新戊基、正己基、正庚基、正辛基、异辛基、正癸基和正十二烷基。
被取代的烷基例如为2-羟基乙基、2-羟基丙基、4-羟基丁基、2-氨基乙基、2-氨基丙基、4-氨基丁基、氰基甲基、2-氰基乙基、2-氯乙基、2-溴甲基和4-氯丁基。
烷氧基的实例有甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、新戊氧基、正己氧基、正庚氧基、正辛氧基、异辛氧基、正癸氧基和正十二烷氧基。
合适的卤素取代基有氟且特别是氯和溴。
在式(1)中,R1优选为氟或三氟甲基。
还优选式(1)的染料,其中R2和R3表示氢、氟、氯、溴、氰基或硝基。
在式(1)中,R4和R5优选表示氢或被三氟甲基、正丙基、正丁基或正丁氧基取代的苯基。
优选由下式表示的式(1)染料:
其中R1为氟或三氟甲基,
R2表示氟、氯、溴或硝基,
R3代表氢、溴、氰基或硝基,且
R4和R5如上定义。
在式(1a)中的R4和R5优选为氢或苯基。
本发明还涉及制备如上定义的式(1)偶氮染料的方法,其中根据常用方法使下式的化合物重氮化:
其中R1、R2和R3如上定义,
且随后与下式的偶合组分偶合:
其中R4和R5如上定义。
式(2)的苯胺为已知的或可根据已知方法制备。一些为市售的。
合适的式(2)苯胺例如为3-三氟甲基-6-甲基苯胺、3-三氟甲基-4-甲基苯胺、2-氯-4-三氟甲氧基苯胺、2-氯-4-三氟甲基苯胺、2-氯-5-三氟甲基苯胺、4-氯-2-三氟甲基苯胺、4-氯-3-三氟甲基苯胺、3,5-双-(三氟甲基)苯胺、3-三氟甲基-4-氰基苯胺、3-三氟甲基-4-硝基苯胺、2-溴-4-三氟甲氧基苯胺、4-溴-2-三氟甲氧基苯胺、2-溴-4-三氟甲基苯胺、4-溴-5-三氟甲基苯胺、4-溴-2-三氟甲基苯胺、4-溴-3-三氟甲基苯胺、2-氟-3-三氟甲基苯胺、2-氟-5-三氟甲基苯胺、2-氟-6-三氟甲基苯胺、4-氟-2-三氟甲基苯胺、4-氟-3-三氟甲基苯胺、2-硝基-4-三氟甲基苯胺、3-硝基-6-三氟甲基苯胺、4-硝基-2-三氟甲基苯胺、2,4-二硝基-6-三氟甲基苯胺、2-溴-4-硝基-6-三氟甲基苯胺和2-氰基-4-硝基-6-三氟甲基苯胺。
式(3)的偶合组分同样为已知的且可通过已知方法,例如通过在US
3,853,895中描述的方法得到。
根据该方法,使2,6-二氯-3-氰基-4-甲基吡啶依次与氨和任选被取代的苯胺反应。由于在离析物(educt)中的两个氯原子的不同反应性,通常得到两种异构产物。
例如,在第一步骤中2,6-二氯-3-氰基-4-甲基吡啶与苯胺的反应产生2-苯基氨基-3-氰基-4-甲基-6-氯吡啶与2-氯-3-氰基-4-甲基-6-苯基氨基吡啶的混合物。
因此,通过与氨的随后反应得到的最终产物主要由以相同异构体比率的2-苯基氨基-3-氰基-4-甲基-6-氨基吡啶与2-氨基-3-氰基-4-甲基-6-苯基氨基吡啶组成。
本发明因此还涉及包含至少两种结构不同的根据权利要求1的式(1)偶氮染料的染料混合物。
所述重氮化以本身已知的方式进行,例如在酸性介质、例如含盐酸或含硫酸的水性介质中用亚硝酸钠进行。然而,所述重氮化也可使用其他重氮化剂进行,例如使用亚硝基硫酸进行。在所述重氮化中,在反应介质中可存在另外的酸,例如磷酸、硫酸、乙酸、丙酸或盐酸或者所述酸的混合物,例如丙酸与乙酸的混合物。所述重氮化有利地在-10℃至30℃、例如-10℃至室温的温度下进行。
重氮化化合物与式(3)的偶合组分的偶合同样以已知方式进行,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。
所使用的酸的实例有盐酸、乙酸、丙酸、硫酸和磷酸。
本发明还涉及包含至少一种式(1)染料和至少一种不同于式(1)的染料的染料混合物。
可有利地与根据本发明的式(1)染料混合的合适染料例如为C.I.分散黄42、C.I.分散黄51、C.I.分散黄65、C.I. 分散黄251、C.I.溶剂黄163、C.I.分散橙157、Palanil Red FFB、C.I.分散红55、C.I.分散红55:1、C.I.分散红59、C.I.分散红60、C.I.分散红75、C.I.分散红86、C.I.分散红91、C.I.分散红92、C.I.分散红133、C.I.分散红146、C.I.分散红191、C.I.分散红279、C.I.分散红302、C.I.分散红302:1、C.I.分散红380、C.I.分散红381、C.I.分散红385、C.I.分散紫57、C.I.分散蓝27、C.I.分散蓝54、C.I.分散蓝56、C.I.分散蓝60、C.I.分散蓝77和C.I.分散蓝379。
根据本发明的染料混合物可例如通过将各个染料简单地混合在一起来制备。
在根据本发明的染料混合物中各个染料的量可以在宽范围内改变。
根据本发明的染料混合物有利地含有至少10重量%、优选至少20重量%且特别是至少40重量%的一种或多种式(1)染料。
根据本发明的染料和染料混合物可用于半合成且特别是合成的疏水性纤维材料、更特别是纺织材料的染色或印刷中。由含有所述半合成和/或合成的疏水性纤维材料的共混物构成的纺织材料同样可使用根据本发明的染料或染料混合物染色或印刷。
所考虑的半合成纤维材料特别是二倍半乙酸纤维素(cellulose 2½ acetate)和三乙酸纤维素。
合成的疏水性纤维材料特别是由直链芳族聚酯、例如对苯二甲酸与二醇、特别是乙二醇的那些,或对苯二甲酸与1,4-双(羟基甲基)环己烷的缩合产物;聚碳酸酯,例如α,α-二甲基-4,4-二羟基-二苯甲烷与光气的聚碳酸酯;和基于聚氯乙烯及基于聚酰胺的纤维组成。
根据本发明的染料和染料混合物对纤维材料的施用根据已知染色方法进行。例如,聚酯纤维材料在浸染方法中在存在常用的阴离子或非离子分散剂和任选的常用的溶胀剂(载剂)的情况下在80-140℃的温度下自水性分散液染色。二倍半乙酸纤维素优选在65-85℃下染色且三乙酸纤维素优选在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将使所述材料仅略微着色(非常好的保留性),使得它们也可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根据热溶法、浸染法染色且适合印刷法。
所述纤维材料可为多种加工形式,例如以纤维、纱线或无纺织物的形式、以机织织物或针织织物的形式。
有利的是,在使用之前将根据本发明的染料和染料混合物转化成染料制剂。为此,将所述染料研磨以使得其粒度平均为0.1-10微米。该研磨可在存在分散剂的情况下进行。例如,将干燥的染料在有分散剂的情况下研磨或用分散剂以浆料形式捏合且随后在真空中或通过雾化干燥。如此得到的制剂可在添加水之后用以制备印刷浆料和染浴。
对于印刷,将使用常用的增稠剂,例如改性或未改性的天然产物,例如海藻酸盐、英国树胶(British gum)、***树胶、结晶树胶、槐豆粉、黄蓍胶、羧甲基纤维素、羟乙基纤维素、淀粉或合成产品,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给予所述材料、特别是聚酯材料具有很好的使用牢度性质、诸如特别是良好的耐光牢度、耐热固着牢度、耐褶裥牢度、耐氯牢度和耐湿牢度如耐水牢度、耐汗牢度和耐洗牢度的稳定色调(level
colour);最终染色品还以很好的耐磨牢度而与众不同。应该特别提到所得染色品对于光、特别是热光的良好牢度性质。
根据本发明的染料和染料混合物还可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自超临界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用于半合成或合成的疏水性纤维材料、特别是纺织材料的染色或印刷的方法,其中将根据本发明的染料施用于所述材料或结合到所述材料中。所述疏水性纤维材料优选为纺织聚酯材料。可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在上文在根据本发明的染料的用途的详述中见到。
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合现代复制方法,例如热转印。
以下实施例用来说明本发明。在实施例中,除非另有陈述,否则份为重量份且百分数为重量%。温度以摄氏度给出。在重量份与体积份之间的关系与在克与立方厘米之间的关系相同。
I. 制备实施例
实施例I.1
A. 重氮化
将10.67g的1M-亚硝基硫酸置于实验室反应设备中。在15-20℃下,引入3.2g
2,4-二溴-6-三氟甲基苯胺。在15-20℃下搅拌2小时之后,将该混合物注入80g冰水中且再搅拌10分钟。过量的亚硝酸盐通过加入氨基磺酸破坏掉。
B. 偶合
将2.3g的2-苯基氨基-3-氰基-4-甲基-6-氨基吡啶与2-氨基-3-氰基-4-甲基-6-苯基氨基吡啶在40ml 80%乙酸中的混合物置于实验室反应设备中且向其中加入2滴Surfynol
104 E (2,4,7,9-四甲基-5-癸炔-4,7-二醇)。在加入30g冰之后,逐滴缓慢加入在A下制备的重氮盐的溶液,以使得内部温度< 15℃。将该混合物搅拌1小时,同时通过加入冰保持温度< 15℃且通过加入30%
NaOH调节pH到3.0-3.5。在加热到50℃之后,将该混合物搅拌30分钟,且然后在吸气下滤出固体,将其用去离子水洗涤并干燥。得到4.8g (8.6mmol,86%产率)的式(101a)和(101b)的金黄色染料的混合物。
实施例I.2
A. 重氮化
在室温下将3.2g 2-氯-5-三氟甲基苯胺溶解于20g的50%硫酸中。在搅拌下加入0.1g冰和5.55g 1M 亚硝基硫酸。在15-20℃下搅拌5小时之后,将该混合物注入65ml乙酸中且再搅拌10分钟。过量的亚硝酸盐通过加入0.5g氨基磺酸破坏掉。
B. 偶合
在5℃下将3.58g的2-苯基氨基-3-氰基-4-甲基-6-氨基吡啶与2-氨基-3-氰基-4-甲基-6-苯基氨基吡啶的混合物加到0.5g Surfynol 104 E (2,4,7,9-四甲基-5-癸炔-4,7-二醇)和0.5g Baykanol®(分散剂,由Lanxess供应)在65ml 80%乙酸中的溶液中。在冷却下逐滴缓慢加入在A下制备的重氮盐的溶液,以使得内部温度为0-5℃。随后,搅拌混合物直至内部温度约为室温且然后在吸气下滤出固体,将其用去离子水洗涤并干燥。得到6.1g
(14mmol,88%产率)的式(102a)和(102b)的染料的混合物。
类似于在实施例I.1中描述的方法制备在表1中列出的染料(102)-(106)。
II. 应用实施例
实施例II.1:
在高温浸染方法中在135℃下在含有1%的染料(101)-(105)中的一种的染浴中将聚酯织物的样品染色。所得染色品表现出≥6的光牢度值。
Claims (10)
2.根据权利要求1的式(1)染料,其中R1为氟或三氟甲基。
3.根据权利要求1或2的式(1)染料,其中R2和R3表示氢、氟、氯、溴、氰基或硝基。
4.根据前述权利要求中任一项的的式(1)染料,其中R4和R5表示氢或被三氟甲基、正丙基、正丁基或正丁氧基取代的苯基。
5.根据权利要求1的式(1)染料,其由下式表示:
其中R1为氟或三氟甲基,
R2表示氟、氯、溴或硝基,
R3代表氢、溴、氰基或硝基,且
R4和R5如在权利要求1中定义。
6.根据权利要求5的式(1a)染料,其中R4和R5为氢或苯基。
8.染料混合物,其包含至少两种结构不同的根据权利要求1的式(1)偶氮染料。
9.用于半合成或合成的疏水性纤维材料的染色或印刷的方法,其中将根据权利要求1的式(1)染料或根据权利要求14的染料混合物施用于所述材料或结合到所述材料中。
10.根据权利要求1的式(1)染料在半合成且特别是合成的疏水性纤维材料、更特别是纺织材料的染色或印刷中的用途。
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PCT/EP2011/071170 WO2012084417A1 (en) | 2010-12-20 | 2011-11-28 | Disperse azo dyes |
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Cited By (3)
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CN106280535A (zh) * | 2016-08-08 | 2017-01-04 | 绍兴文理学院 | 一种高水洗牢度分散染料及其制备方法与应用 |
CN108947765A (zh) * | 2018-08-15 | 2018-12-07 | 江苏常源新材料科技有限公司 | 一种双重氮化反应一步合成邻二溴苯的方法 |
CN112375399A (zh) * | 2020-11-19 | 2021-02-19 | 辽宁嘉禾精细化工股份有限公司 | 单偶氮化合物、制备方法及其用途 |
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WO2014040810A1 (en) | 2012-09-12 | 2014-03-20 | Huntsman Advanced Materials (Switzerland) Gmbh | Inks and a process for ink-jet printing textile fibre materials |
KR101823713B1 (ko) * | 2013-03-07 | 2018-01-31 | (주)엘지하우시스 | 광학적 특성 및 내스크래치성이 우수한 비산 방지 필름 및 그 제조 방법 |
EP2995653A1 (en) * | 2014-09-15 | 2016-03-16 | DyStar Colours Distribution GmbH | High wet-fast disperse dyes and mixtures thereof |
TWI707002B (zh) * | 2016-05-25 | 2020-10-11 | 瑞士商杭斯曼高級材料公司 | 分散偶氮染料、其製備方法及其用途 |
WO2018114140A1 (en) | 2016-12-20 | 2018-06-28 | Huntsman Advanced Materials (Switzerland) Gmbh | Inks and a process for ink-jet printing textile fibre materials |
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CN112375399A (zh) * | 2020-11-19 | 2021-02-19 | 辽宁嘉禾精细化工股份有限公司 | 单偶氮化合物、制备方法及其用途 |
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BR112013012541A2 (pt) | 2016-08-02 |
MX340589B (es) | 2016-07-13 |
TW201237110A (en) | 2012-09-16 |
WO2012084417A1 (en) | 2012-06-28 |
MX2013006975A (es) | 2013-08-01 |
EP2655518B1 (en) | 2016-01-06 |
BR112013012541B1 (pt) | 2020-12-01 |
JP2013545859A (ja) | 2013-12-26 |
US20130255011A1 (en) | 2013-10-03 |
TWI547526B (zh) | 2016-09-01 |
ES2563320T3 (es) | 2016-03-14 |
EP2655518A1 (en) | 2013-10-30 |
BR112013012541B8 (pt) | 2023-05-16 |
US9938411B2 (en) | 2018-04-10 |
DK2655518T3 (da) | 2016-03-14 |
KR20130132557A (ko) | 2013-12-04 |
JP5897032B2 (ja) | 2016-03-30 |
KR101940466B1 (ko) | 2019-04-10 |
CN103249780B (zh) | 2015-11-25 |
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