EP1836262A2 - Colorants reactifs contenant de la triphendioxazine, procede de production associe et utilisation desdits colorants - Google Patents
Colorants reactifs contenant de la triphendioxazine, procede de production associe et utilisation desdits colorantsInfo
- Publication number
- EP1836262A2 EP1836262A2 EP05826413A EP05826413A EP1836262A2 EP 1836262 A2 EP1836262 A2 EP 1836262A2 EP 05826413 A EP05826413 A EP 05826413A EP 05826413 A EP05826413 A EP 05826413A EP 1836262 A2 EP1836262 A2 EP 1836262A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrogen
- alkyl
- general formula
- phenyl
- group
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title abstract description 26
- 239000000975 dye Substances 0.000 title description 57
- 238000007639 printing Methods 0.000 claims abstract description 33
- 238000004043 dyeing Methods 0.000 claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- -1 phenylene, substituted phenylene Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 239000004753 textile Substances 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 239000011734 sodium Chemical group 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052700 potassium Chemical group 0.000 claims description 6
- 239000011591 potassium Chemical group 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000005521 carbonamide group Chemical group 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000008569 process Effects 0.000 description 16
- 235000002639 sodium chloride Nutrition 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000835 fiber Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000004744 fabric Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000002657 fibrous material Substances 0.000 description 10
- 239000004952 Polyamide Substances 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229920002647 polyamide Polymers 0.000 description 9
- 210000002268 wool Anatomy 0.000 description 9
- 229920003043 Cellulose fiber Polymers 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000985 reactive dye Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000004627 regenerated cellulose Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- 229940015975 1,2-hexanediol Drugs 0.000 description 2
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- 229920000926 Galactomannan Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 125000005385 peroxodisulfate group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
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- 239000002736 nonionic surfactant Substances 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 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
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4405—Dioxazine dyes
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/046—Specific dyes not provided for in group C09B62/06 - C09B62/10
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/205—Specific dyes not provided for in groups C09B62/22 - C09B62/26
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- the present invention is in the field of fiber-reactive dyes and relates to dyes having a triphendioxazine structure.
- WO 99/51681 already discloses triphendioxazine dyes which contain reactive anchors. However, these have a number of technical disadvantages in the dyeing of textile materials.
- Object of the present invention is to provide dyes having improved properties.
- the present invention thus relates to triphendioxazine dyes of the general formula I.
- a 1 and A 2 are independently hydrogen, phenyl, (CVC 6 ) -alkyl or substituted (dC 6 ) -alkyl;
- B is phenylene, substituted phenylene, naphthylene or substituted
- Naphthylene is;
- R 1 is hydrogen, (C r C 6 ) alkyl or phenyl;
- Y 1 represents a group of the general formula II or III
- X 1 to X 3 independently of one another denote hydrogen, cyano or halogen, where at least one radical X 2 or X 3 is halogen;
- X 4 is chlorine or fluorine
- R 2 and R 3 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl
- R 2 and R 3 together with the N atom bearing them, form a five- or six-membered saturated ring containing one or two -O- groups or
- R 7 is hydrogen or (C r C 6 ) alkyl
- M is hydrogen, ammonium, an alkali metal or the equivalent of a
- R 4 and R 5 independently of one another represent hydrogen, (C 1 -C 6) -alkyl or
- R 6 is hydrogen, (C 1 -C 6 ) alkyl or phenyl
- (C 1 -C 6 ) -Alkyl groups may be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, i-propyl, sec-propyl, n-butyl, sec-butyl. i-butyl, tert. Butyl, n-pentyl or n-hexyl mean.
- (C 1 -C 6 ) -alkoxy groups ! which may thus mean, for example, methoxy or ethoxy.
- (C 3 -C 8 ) -cycloalkyl is preferably cyclopentyl and cyclohexyl, but may also be cyclobutly and cycloheptyl.
- Halogen may be, for example, fluorine, chlorine or bromine.
- an alkali metal represented by M is lithium, sodium and potassium, while an alkaline earth metal whose equivalent of M may be especially calcium.
- M is in particular hydrogen, lithium, sodium and potassium, with hydrogen and sodium being particularly preferred.
- a standing for Y 2 group which can be eliminated by the action of alkali is, for example chloro, -OSO 3 M, -S 2 O 3 M, -OPO 3 M 2 and (C 2 -C 5) alkanoyloxy, such For example, acetyloxy, and sulfobenzoyloxy.
- a preferred meaning for Y 2 is sulfato.
- Substituted alkyl represented by A 1 or A 2 is, for example, substituted by hydroxy, amino or sulfato and is preferably hydroxyethyl, sulfatoethyl or aminoethyl.
- a 1 and A 2 preferably have the same meaning and more preferably both are hydrogen.
- Substituents of phenylene and naphthylene groups standing for B are, for example, (C 1 -C 6 ) -alkyl, in particular methyl, ethyl, propyl and butyl, and halogen, in particular chlorine.
- B is preferably 1, 4-phenylene, 1, 3-phenylene, 2,6-naphthylene or 2,7-naphthylene.
- R 1 is preferably hydrogen, methyl, ethyl or phenyl, with hydrogen and methyl being particularly preferred.
- R 1 is preferably hydrogen, methyl, ethyl or phenyl, with hydrogen and methyl being particularly preferred.
- a 1 and A 2 are hydrogen;
- B is 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene or 2,7-naphthylene; and
- R 1 is hydrogen, methyl, ethyl or phenyl.
- Inventive Triphendioxazinfarbstoffe of the general formula I in which Y 1 is a group of the general formula II, may be present in mixtures with one another, in which the individual dyes differ in particular only in the reactive group of the general formula II.
- Preferred mixtures of this type contain, for example, a reactive dye in which Y 1 is a group of the formula IIa
- X 1 to X 3 are preferably cyano, fluorine or chlorine.
- Particularly preferred groups of the formula II have the structures Mc to Mf
- the structure -NR 2 R 3 is preferably derived from the following amines HNR 2 R 3 : ammonia, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, tert-butylamine, n-pentylamine, n-hexylamine, cyclohexylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, methylethylamine, Ethanolamine, diethanolamine, 2-methoxyethylamine, 2-ethoxyethylamine, sulfatoethylamine, aminoacetic acid, N-methylaminoacetic acid, taurine, N-methyltaurine, methylaminomethanesulfonic acid
- R • sc. O -.d-je -., R-n R3 contain an -SO 2 Z group, the following being
- R 8 is hydrogen, (C 1 -C 4 ) -alkyl, in particular methyl, or phenyl;
- R9, R10 and R 13 is hydrogen, (C r C4) alkyl, especially methyl and ethyl, or by hydroxy, -SO 3 M, -OSO 3 M, -COOM or cyano-substituted (Ci-C 4) - AI kyl, in particular hydroxyethyl, sulfoethyl or sulfatoethyl; R 11 and R 12 are independently hydrogen, (Ci-C 4 ) -alkyl, in particular
- R 14 is hydrogen or -SO 3 M
- R 15 is hydrogen, (C 1 -C 4 ) -alkyl or phenyl
- M is hydrogen, sodium or potassium.
- R 16 is hydrogen, (dC 4) -alkyl or by hydroxy, -SO 3 M, -OSO 3 M, -COOM or cyano (dC 4) -alkyl; R 17 is hydrogen or -SO 3 M; X 5 is defined as indicated above; and M is hydrogen, sodium or potassium.
- Particularly preferred groups of the general formula III have the structures IIIa to IIIc
- Inventive Triphendioxazinfarbstoffe of the general formula I which contain a radical -SO 2 Z, may have different structure with respect to the fiber-reactive group -SO 2 Z with otherwise the same structure.
- the proportion of the dye in vinylsulfonyl form may be up to about 95 mol%, based on the particular dye chromophore.
- the triphendioxazine dyes of the general formula I according to the invention are generally present as a dye preparation in solid, dissolved or finely dispersed form.
- they generally contain the usual in water-soluble and especially fiber-reactive dyes electrolyte salts, such as sodium chloride, potassium chloride and sodium sulfate, and may further contain the usual in commercial dyes aids, such as buffer substances having a pH in aqueous solution between 3 and 7 such as sodium acetate, sodium borate, sodium bicarbonate, sodium dihydrogen phosphate, sodium tricitrate and Dinathumhydrogenphosphat, small amounts of siccatives or, if they are in liquid, aqueous solution (including the level of thickening agents, as are common in printing pastes), substances that ensure the durability of these preparations, such as mildewproofing agents.
- the triphendioxazine dyestuffs of the general formula I according to the invention are present as dyestuff powders or as dyestuff granules with a content of 10 to 80% by weight, based on the dyestuff powder or the granules, of an electrolyte salt, which is also referred to as adjusting agent.
- Granules have in particular grain sizes of 50 to 500 Dm.
- These solid preparations may also contain the mentioned buffer substances in a total amount of up to 10 wt .-%, based on the preparation.
- the total dye content in these aqueous solutions is up to about 50% by weight, for example 5 and 50% by weight, the electrolyte salt content in these aqueous solutions preferably being below 10 Wt .-%, based on the aqueous solution is.
- the aqueous solutions (liquid preparations) may contain the mentioned buffer substances usually in an amount of up to 10% by weight, for example 0.1 to 10% by weight. Preference is given to up to 2% by weight, for example from 0.1 to 2% by weight.
- Preferred preparations of the triphendioxazine dyes of the general formula I according to the invention can be prepared, for example, by grinding a triphendioxazine dye of the general formula I in the presence of water in suitable mills and, if a pulverulent preparation is to be prepared, subsequently removing the liquid.
- Suitable mills are, for example, ball, vibrating, pearl or sand mills.
- the Triphendioxazinfarbstoff preferably in the form of an aqueous Farbstoffpreßkuchens and in the presence of suitable, known in the art auxiliaries, ground to a particle size of 0.5 to 5 Dn.
- a particle size distribution is desirable in which 50 to 90% of the particles have a size ⁇ 1 Dn. It may be advantageous under certain circumstances to premix triphendioxazine dye, auxiliaries and water in a stirred tank or impact trough or to pre-comminute it in a colloid mill.
- the grinding process can be carried out continuously in a mill cascade or discontinuously in a milling apparatus.
- the grinding process is preferably performed at 0 to 100 0 C, particularly preferably at 20 to 40 ° C is performed.
- Suitable aggregates for spray drying are vacuum paddle dryers or preferably atomizing dryers. To atomize the Mahl ashamedes here two-fluid nozzles, pressure nozzles or discs can be used.
- Nonionic dispersants or emulsifiers are, for example, reaction products of alkylene oxides such as ethylene or propylene oxide with alkylatable compounds such as fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, arylalkylarylphenols and carboxylic acid amides such as
- Triphendioxazinfarbstoffe the general formula I can be prepared, for example, characterized in that a compound of general formula V wherein A 1 , A 2 , B, R 1 and M are defined as indicated above, with a compound of general formula VI
- D is fluorine or chlorine and Het is a group of the formulas II or III, is reacted.
- R 1 and B are defined as indicated above, or a salt thereof, in
- Suitable oxidizing agents are, for example, iron (III) salts, peroxodisulfates
- Persulfates permanganate, manganese dioxide, chromic acid, peroxides, peracids,
- Peroxodisulfates and iron (III) salts are preferred.
- triphendioxazine dyes of general formula I in which Y 1 is a group of general formula III may also be prepared by reacting trifluorotriazine or trichlorothazine with a compound of general formula V to give the compound of general formula IX
- a 1 , A 2 , B, R 1 and M are defined as defined above and F / Cl is fluorine or chlorine, and further reaction to Triphendioxazinfarbstoff of the general formula I with an amine HNR 2 R 3 , wherein R 2 and R 3 are defined as indicated above.
- triphendioxazine dyes of the general formula I according to the invention are obtained in the above-described preparation processes as a solution or suspension and can be isolated by salting out. They can also be spray-dried, and evaporation of the solution or suspension is also possible.
- the triphendioxazine dyes of the general formula I according to the invention have valuable performance properties. They are used for dyeing and printing hydroxyl- and / or carboxamido-containing materials, for example in the form of fabrics, such as paper and leather or films, such as polyamide or in the mass, such as polyamide and polyurethane, but especially in the form of Fibers of the materials mentioned used. They are preferred for dyeing and printing cellulose-containing fiber materials of all kinds used. In addition, they are also suitable for dyeing or printing hydroxyl-containing fibers contained in blend fabrics, eg. As mixtures of cotton with polyester fibers or polyamide fibers. It is also possible to use them to print textiles or paper using the ink jet process.
- the present invention thus also relates to the use of Triphendioxazinfarbstoffe invention of the general formula I for dyeing or printing the materials mentioned or methods for dyeing or printing such materials in per se conventional procedures, in which one or more Triphendioxazinfarbstoffe invention of the general formula I uses as a colorant.
- the materials mentioned are preferably used in the form of fiber materials, in particular in the form of textile fibers, such as fabrics or yarns, such as in the form of strands or wound bodies.
- Hydroxy-containing materials are those natural or synthetic
- Cellulose fiber matehales are preferably cotton, but also other vegetable fibers such as linen, hemp, jute and ramie fibers.
- Regenerated cellulose fibers are, for example, cotton wool and
- Carboxamido-containing materials are, for example, synthetic and natural polyamides and polyurethanes, in particular in the form of fibers, for example wool and other animal hair, silk, leather, polyamide-6,6, polyamide-6, polyamide-1 and polyamide-4.
- the Triphendioxazinfarbstoffe invention of the general formula I can be on the substrates mentioned, in particular the above
- Fiber materials apply according to known application techniques and fix.
- cellulose fibers by exhaustion from a long liquor using various acid-binding agents and optionally neutral salts, such as sodium chloride or sodium sulfate, dyeings with very good, color yields.
- acid-binding agents such as sodium chloride or sodium sulfate
- dyeings with very good, color yields.
- the extraction process at a pH of 3 to 7, in particular at a pH of 4 to 6 dyed.
- Liquor ratio can be chosen within a wide range and is for example between 1: 3 and 1:50, preferably between 1: 5 and 1: 30. It is preferably dyed in an aqueous bath at temperatures between 40 and 105 ° C, optionally at a temperature up to 130 ° C under pressure, and optionally in the presence of conventional dyeing auxiliaries. To increase the wet fastness of the dyed material can be removed in an aftertreatment non-fixed dye. This aftertreatment is carried out in particular at a pH of 8 to 9 and temperatures of 75 to 80 ° C. One can proceed in such a way that one brings the material into the warm bath and this gradually heats up to the desired temperature and the
- the neutral salts which accelerate the removal of the dyes can also be added to the bath only after the actual dyeing temperature has been reached.
- the acid-binding and the fixing of the dyes on the cellulose fibers causing agents are, for example, water-soluble basic salts of alkali metals and also alkaline earth metals of inorganic or organic acids or compounds which release alkali in the heat.
- alkali metal hydroxides and alkali metal salts of weak to medium inorganic or organic acids are mentioned, of which
- Alkali compounds preferably the sodium and potassium compounds are meant.
- Such acid-binding agents are, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogen phosphate, dinathium hydrogen phosphate, sodium trichloroacetate, water glass or trisodium phosphate.
- Triphendioxazinfarbstoffe of the general formula I according to the invention are characterized by high reactivity, good fixability, very good build-up, and high light and perspiration light fastness. You can Therefore, they are used after the exhaust dyeing process at low dyeing temperatures and require only short steaming times in pad-steam processes.
- the degrees of fixation are high, and the unfixed portions can be easily washed out, the difference between the degree of exhaustion and the degree of fixation remarkably small, ie the Seifbib is very low.
- felt-free or low-felt wool are also possible to use felt-free or low-felt wool (compare, for example, H. Rath, Lehrbuch der Textilchemie, Springer-Verlag, 3rd edition (1972), pp. 295-299), in particular the equipment according to the so-called Hercosett method (p J. Soc. Dyers and Colorists 1972, 93-99, and 1975, 33-44) with very good
- the process of dyeing wool is carried out here in the usual and well-known Därbeweise from an acidic environment.
- acetic acid and / or ammonium sulfate or acetic acid and ammonium acetate or sodium acetate can be added to the dyebath to obtain the desired pH.
- conventional leveling agents such as based on a reaction product of cyanuric chloride with three times the molar amount of an aminobenzenesulfonic acid and / or a Aminonaphthalinsulfonklare or based on a reaction product of, for example, stearylamine with ethylene oxide.
- the dye mixture according to the invention is preferably first subjected to the exhaustion process from acid dyebath having a pH of about 3.5 to 5.5 under the control of the pH and the pH then, towards the end of the dyeing time, in the neutral and possibly weak shifted alkaline range to a pH of 8.5, especially to achieve high color depths, the full reactive binding between the dyes of the dye mixtures of the invention and the fiber bring about. At the same time, the non-reactively bound dye is dissolved.
- the procedure described here preferably also applies to the production of dyeings on fiber materials from other natural polyamides or from synthetic polyamides and polyurethanes.
- dyeing these materials it is possible to use the customary dyeing and printing processes described in the literature and known to the person skilled in the art (see, for example, H.K. Rouette, Handbook of Textile Finishing, Deutscher fraverlag GmbH, Frankfurt am Main).
- Dyeing liquors and printing pastes which consist of dissolved or finely dispersed dyes, can contain other additives besides the triphendioxazine dyes of the general formula I and water.
- Additives are for example wetting agents, anti-foaming agents, leveling agents and the properties of the fabric influencing agents, such as softening agents, additives for flameproofing and dirt, water and oil repellent or water-softening agents.
- printing pastes may also contain natural or synthetic thickeners, such as alginates and cellulose ethers. In dyeing baths and printing pastes, the amounts of dye can vary within wide limits depending on the desired color depth.
- the triphendioxazine dyes of the general formula I are present in amounts of from 0.01 to 15% by weight, in particular in amounts of from 0.1 to 10% by weight, based on the dyestuff or the printing paste.
- triphendioxazine dyes of the general formula I according to the invention are characterized in that unfinished dye components on the fiber material can be washed out very easily after the dyeing process, without whitening, which is involved in the washing process, being soiled by the detaching dye. This results in advantages for the dyeing process, in which washing cycles and thus costs are saved.
- the dyeings and prints prepared with the triphendioxazine dyes of the general formula I according to the invention have, in particular on
- Cellulose fiber materials a high color strength and a high fiber-dye binding stability, both in the acidic and in the alkaline range, continue to have good light fastness and very good wet fastness properties, such as washing, water, seawater, dyeing and perspiration fastness and good pleating fastness, Ironing fastness and rubbing fastness.
- the present invention relates to the use of Triphendioxazinfarbstoffe invention of the general formula I in printing inks for the digital Textile printing, as well as the aforementioned printing inks themselves.
- digital textile printing is understood in the context of the present description, in particular the inkjet method.
- the printing inks of the invention are preferably aqueous and comprise one or more of the triphendioxazine dyes of the general formula I according to the invention, for example in amounts of from 0.1% by weight to 50% by weight, preferably in amounts of from 1% by weight to 30% by weight. % and more preferably in amounts of from 1% to 15% by weight, based on the total weight of the ink. Also may be included combinations of the invention
- a conductivity of 0.5 to 25 mS / m can be set by addition of electrolyte.
- the electrolyte for example, lithium nitrate and potassium nitrate are suitable.
- the printing inks of the invention may contain organic solvents having a total content of 1-50%, preferably 5-30% by weight.
- Suitable organic solvents are, for example, alcohols, for. As methanol, ethanol, 1-propanol, isopropanol, 1-butanol, tert. Butanol, pentyl alcohol, polyhydric alcohols, such as 1, 2-ethanediol, 1, 2,3-propanetriol,
- Amines such as, for example, methylamine, ethylamine, triethylamine, diethylamine, dimethylamine, thymethylamine, dibutylamine, diethanolamine, triethanolamine, N-acetylethanolamine, N-formylethanolamine and ethylenediamine
- urea derivatives such as, for example, urea, thiourea, N-methylurea, N, N ' ⁇ -dimethylurea, ethyleneurea and 1,1,3,3-tetramethylurea
- amides such as, for example, dimethylformamide, dimethylacetamide and acetamide, ketones or ketoalcohols, for example acetone and diacetone alcohol, cyclic ethers, for example tetrahydrofuran, trimethylolethane, trimethylolpropane, 2-butoxyethanol, benzyl alcohol, 2-butoxyethanol, gamma-butyrolactone, epsilon-caprolact
- the printing inks according to the invention may contain the usual additives, such as viscosity moderators to adjust viscosities in the range of 1, 5 to 40.0 mPas in a temperature range from 20 to 50 ° C.
- Preferred inks have a viscosity of 1.5 to 20 mPas and particularly preferred inks have a viscosity of 1.5 to 15 mPas.
- Suitable viscosity moderators are rheological additives, for example: polyvinylcaprolactam, polyvinylpyrrolidone and also their co-polymers, Polyether polyol, associative thickener, polyurea, polyurethane, sodium alginates, modified galactomannans, polyether urea, polyurethane and nonionic
- the printing inks of the invention can surface-active substances for the adjustment of surface tensions of 20 to 65 mN / m, which are optionally adjusted depending on the method used (thermal or piezo technology).
- Suitable surface-active substances are, for example, surfactants of all kinds, preferably nonionic surfactants, butyldiglycol and 1,2-hexanediol.
- the inks may still contain conventional additives such as fungicidal and bacterial growth inhibiting agents in amounts of from 0.01 to 1% by weight based on the total weight of the ink.
- the inks can be prepared in a conventional manner by mixing the components in water.
- the printing inks of the invention are suitable for use in
- Ink-jet printing process for printing a wide variety of preprepared materials, such as silk, leather, wool, polyamide fibers and polyurethanes, and in particular cellulosic fiber materials of all kinds.
- fiber materials are, for example, the natural cellulose fibers, such as cotton, linen and hemp, as well as pulp and regenerated cellulose.
- Printing inks are also suitable for printing pretreated hydroxyl-containing or amino-containing fibers contained in blend fabrics, z. As mixtures of cotton, silk, wool with polyester fibers or polyamide fibers.
- the auxiliaries have to be applied to the textile substrate in a separate pretreatment step.
- the pretreatment of the textile substrate such as, for example, cellulose and regenerated cellulose fibers and silk and wool, takes place before printing with an aqueous alkaline liquor.
- alkali such as sodium carbonate, sodium bicarbonate, sodium acetate, trisodium phosphate, sodium silicate, sodium hydroxide, alkali donors such as Sodium chloroacetate, sodium formate, hydrotropic substances such as urea, reduction inhibitors such as Nathumnitrobenzolsulfonate, and thickeners that prevent the flow of the motifs when applying the ink, these are, for example, sodium alginates, modified polyacrylates or highly etherified galactomannans.
- pre-preparation reagents are applied uniformly to the textile substrate in a defined amount using suitable application equipment, for example a 2- or 3-roll padder, contactless spray technologies, foam application or appropriately adapted inkjet technologies, followed by drying.
- suitable application equipment for example a 2- or 3-roll padder, contactless spray technologies, foam application or appropriately adapted inkjet technologies, followed by drying.
- the textile fiber material is dried at 120 to 150 ° C and then fixed.
- the fixation of the inkjet prints prepared with reactive dyes can be carried out at room temperature, or with saturated steam, with superheated steam, with hot air, with microwaves, with infrared radiation, with laser or electron beams or with other suitable types of energy transfer.
- the prints produced with the printing inks according to the invention have, in particular on cellulose fiber materials, a high color strength and a high fiber-dye bonding stability in both the acidic and in the alkaline range, furthermore good light fastness and very good wet fastness properties, such as washing, water, seawater -, over-dyeing and perspiration, as well as a good pleating, ironing and rubbing fastness.
- the following examples serve to illustrate the present invention.
- the parts are by weight, the percentages are by weight unless otherwise stated. Parts by weight refer to parts by volume such as kilograms to liters.
- the compounds described by formula in the examples are given in the form of the free acid. In general, however, they are in the form of their alkali metal salts, such as lithium, sodium or potassium salts, prepared and isolated and used in the form of their salts for dyeing.
- the starting compounds and components mentioned in the following examples, in particular table examples, in the form of the free acid and components as such or in the form of their salts, preferably alkali metal salts can be used in the synthesis.
- the absorption maxima ( ⁇ ) in the visible range indicated for the dyes according to the invention were determined on the basis of their alkali metal salts in aqueous solution.
- Example 1 a) 74.2 parts of a compound of the formula
- the reaction mixture is cooled to 15-20 ° C, with 2N sodium hydroxide solution to pH 1 1 - 1 1, 5 provided, maintained and stirred.
- the pH is adjusted to 6.5 - 7 and the suspended dye is filtered off and dried. 10 g of the dye obtained are milled in a bead mill (100 g glass beads, diameter 0.3-0.4 mm) in the presence of 70 ml of water at 25 ° C. for 6 hours.
- the pH is adjusted to 4.5 with acetic acid (80%).
- the dyebath is heated to 50 ° C for 10 minutes and then 100 parts of a wool fabric are added.
- the mixture is heated to a temperature of 100 ° C. within 50 minutes and dyed at this temperature for 60 minutes.
- the wool fabric is washed with warm and cold water, then spun and dried. It is a blue color with good light and wet fastness, and good Faseregaltician obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Ink Jet (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004063724A DE102004063724A1 (de) | 2004-12-31 | 2004-12-31 | Reaktive Triphendioxazin-Farbstoffe,Verfahren zu ihrer Herstellung und ihre Verwendung |
PCT/EP2005/056969 WO2006072548A2 (fr) | 2004-12-31 | 2005-12-20 | Colorants reactifs contenant de la triphendioxazine, procede de production associe et utilisation desdits colorants |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1836262A2 true EP1836262A2 (fr) | 2007-09-26 |
Family
ID=36570491
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05826413A Withdrawn EP1836262A2 (fr) | 2004-12-31 | 2005-12-20 | Colorants reactifs contenant de la triphendioxazine, procede de production associe et utilisation desdits colorants |
Country Status (8)
Country | Link |
---|---|
US (1) | US7414129B2 (fr) |
EP (1) | EP1836262A2 (fr) |
JP (1) | JP2008527062A (fr) |
KR (1) | KR20070089982A (fr) |
CN (1) | CN101048466B (fr) |
DE (1) | DE102004063724A1 (fr) |
TW (1) | TW200641057A (fr) |
WO (1) | WO2006072548A2 (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2331783B1 (es) * | 2008-05-20 | 2010-10-27 | Universidad De Granada | Compuesto para el etiquetado de biomoleculas basado en vinilsulfona, preparacion y usos. |
DE102008061843B4 (de) * | 2008-12-15 | 2018-01-18 | Novaled Gmbh | Heterocyclische Verbindungen und deren Verwendung in elektronischen und optoelektronischen Bauelementen |
WO2012064859A2 (fr) * | 2010-11-12 | 2012-05-18 | Invista Technologies S.Ar.L. | Dispersion aqueuse de teinture, d'un agent antitache, et d'une substance chimique fluorée et son utilisation dans la fabrication d'un tapis |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3503564A1 (de) * | 1985-02-02 | 1986-08-07 | Bayer Ag, 5090 Leverkusen | Aminoalkylensulfon-triphendioxazin-farbstoffe |
DE4415692A1 (de) * | 1994-05-04 | 1995-11-09 | Hoechst Ag | Wasserlösliche Triphendioxazinverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe |
TR200002865T2 (tr) * | 1998-04-03 | 2001-04-20 | Clariant International Ltd. | Organik bileşikler. |
-
2004
- 2004-12-31 DE DE102004063724A patent/DE102004063724A1/de not_active Withdrawn
-
2005
- 2005-12-20 JP JP2007548806A patent/JP2008527062A/ja not_active Withdrawn
- 2005-12-20 KR KR1020077015048A patent/KR20070089982A/ko not_active Application Discontinuation
- 2005-12-20 CN CN200580037247XA patent/CN101048466B/zh not_active Expired - Fee Related
- 2005-12-20 WO PCT/EP2005/056969 patent/WO2006072548A2/fr active Application Filing
- 2005-12-20 EP EP05826413A patent/EP1836262A2/fr not_active Withdrawn
- 2005-12-20 US US11/722,906 patent/US7414129B2/en not_active Expired - Fee Related
- 2005-12-29 TW TW094147270A patent/TW200641057A/zh unknown
Non-Patent Citations (1)
Title |
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See references of WO2006072548A2 * |
Also Published As
Publication number | Publication date |
---|---|
KR20070089982A (ko) | 2007-09-04 |
TW200641057A (en) | 2006-12-01 |
WO2006072548A2 (fr) | 2006-07-13 |
CN101048466A (zh) | 2007-10-03 |
JP2008527062A (ja) | 2008-07-24 |
DE102004063724A1 (de) | 2006-07-13 |
US7414129B2 (en) | 2008-08-19 |
US20080114166A1 (en) | 2008-05-15 |
WO2006072548A3 (fr) | 2006-08-31 |
CN101048466B (zh) | 2010-06-09 |
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