EP0546476B1 - Verfahren zur Herstellung eines modifizierten Faser- materials und Verfahren zum Färben des modifizierten Fasermaterials mit anionischen Farbstoffen - Google Patents
Verfahren zur Herstellung eines modifizierten Faser- materials und Verfahren zum Färben des modifizierten Fasermaterials mit anionischen Farbstoffen Download PDFInfo
- Publication number
- EP0546476B1 EP0546476B1 EP92120726A EP92120726A EP0546476B1 EP 0546476 B1 EP0546476 B1 EP 0546476B1 EP 92120726 A EP92120726 A EP 92120726A EP 92120726 A EP92120726 A EP 92120726A EP 0546476 B1 EP0546476 B1 EP 0546476B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- sulfato
- groups
- amino
- carbon atoms
- 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.)
- Expired - Lifetime
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- 238000004043 dyeing Methods 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 93
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 12
- 239000002657 fibrous material Substances 0.000 title claims description 70
- 239000000975 dye Substances 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000000463 material Substances 0.000 claims abstract description 42
- 125000004185 ester group Chemical group 0.000 claims abstract description 38
- 239000000243 solution Substances 0.000 claims abstract description 33
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 23
- 239000003513 alkali Substances 0.000 claims abstract description 21
- 239000003792 electrolyte Substances 0.000 claims abstract description 21
- 239000000835 fiber Substances 0.000 claims abstract description 20
- 150000007824 aliphatic compounds Chemical class 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 230000004048 modification Effects 0.000 claims abstract description 5
- 238000012986 modification Methods 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 3
- -1 amino, sulfo, hydroxyl Chemical group 0.000 claims description 177
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 41
- 125000003277 amino group Chemical group 0.000 claims description 41
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229920000728 polyester Polymers 0.000 claims description 15
- 239000000985 reactive dye Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000986 disperse dye Substances 0.000 claims description 12
- 229920003043 Cellulose fiber Polymers 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 26
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 64
- 229920000742 Cotton Polymers 0.000 description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- 238000010521 absorption reaction Methods 0.000 description 19
- 239000000080 wetting agent Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 239000002736 nonionic surfactant Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000987 azo dye Substances 0.000 description 7
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- 238000005406 washing Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000001007 phthalocyanine dye Substances 0.000 description 5
- 239000002985 plastic film Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920006255 plastic film Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- AOLYLEFSPFALGJ-UHFFFAOYSA-N copper formazan Chemical compound [Cu].NN=CN=N AOLYLEFSPFALGJ-UHFFFAOYSA-N 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000009981 jet dyeing Methods 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 239000000661 sodium alginate Substances 0.000 description 3
- 235000010413 sodium alginate Nutrition 0.000 description 3
- 229940005550 sodium alginate Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241001584775 Tunga penetrans Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- 230000007935 neutral effect Effects 0.000 description 2
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 1
- HKGUIHSMIUZNSS-UHFFFAOYSA-N 1,1-dimethyl-2-propan-2-ylhydrazine Chemical compound CC(C)NN(C)C HKGUIHSMIUZNSS-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
- AMOCRPYGDBWXEK-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=CC=NC(S(C)(=O)=O)=N1 AMOCRPYGDBWXEK-UHFFFAOYSA-N 0.000 description 1
- LXSLRBQXKPGTHX-UHFFFAOYSA-N 2-(benzenesulfonyl)-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1S(=O)(=O)C1=CC=CC=C1 LXSLRBQXKPGTHX-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- CTRXDTYTAAKVSM-UHFFFAOYSA-N 3-{[ethyl({4-[(4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)(2-sulfophenyl)methylidene]cyclohexa-2,5-dien-1-ylidene})azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S(O)(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 CTRXDTYTAAKVSM-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- FFISWZPYNKWIRR-UHFFFAOYSA-N 5-oxidophenazin-5-ium Chemical compound C1=CC=C2[N+]([O-])=C(C=CC=C3)C3=NC2=C1 FFISWZPYNKWIRR-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PBWGZYPICGDRCF-UHFFFAOYSA-N CNC(=C=C)NCC Chemical group CNC(=C=C)NCC PBWGZYPICGDRCF-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
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- 206010013786 Dry skin Diseases 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
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- 229920002292 Nylon 6 Polymers 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GUTBHOXHMJMIQV-UHFFFAOYSA-N amino ethyl sulfate Chemical group CCOS(=O)(=O)ON GUTBHOXHMJMIQV-UHFFFAOYSA-N 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000004999 nitroaryl group Chemical group 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009970 yarn dyeing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- 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
- D06P1/39—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 acid 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/62—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—Compounds containing nitrogen
-
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
-
- 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
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
-
- 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
- Y10S8/93—Pretreatment before dyeing
Definitions
- the use of alkaline agents is particularly necessary to fix the technically important reactive dyes on the fiber.
- a dyeing process which can be carried out with little or no salt and at the same time only with the use of small amounts of an alkaline agent or entirely without such an alkaline auxiliary is therefore particularly advantageous in the dyeing process using fiber-reactive dyes.
- a fiber material is used as the textile material used which has been pretreated and modified by a compound which is a saturated aliphatic compound of 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, optionally substituted by 1 or 2 or more, such as 3 to 5, hydroxyl groups which contains at least one primary, secondary or tertiary amino group or quaternary ammonium group and at least one hydrolysable ester group, the aliphatic radical (s) being (s) being straight-chain, branched and / or cyclic and optionally by one or more , such as two or three, hetero groups, such as amino groups and d Oxygen atoms, which can be interrupted and the amino group (s) can also be part of a saturated heterocyclic radical,
- the amino and ester group-containing compounds used according to the invention in particular those containing sulfuric acid ester groups, cannot form an ethyleneimine structure because of their constitution; they are able to react with the cellulose fiber according to a nucleophilic substitution.
- the amount of alkali used can be reduced by 75%; the fixing times can also be drastically reduced. Since in the process according to the invention the application can be carried out analogously to conventional dyeing processes, the process according to the invention can be integrated into a continuous process for the general pretreatment of fiber materials where the alkali necessary for fixing is already present.
- the process according to the invention for dyeing fiber materials modified according to the invention permits the one-off dyeing of polyester / cotton blended fabrics with reactive and disperse dyes without damage to the disperse dye, precisely because alkali is not present in this single-bath dyeing process.
- the compounds which can be used according to the invention for modifying fiber materials contain as ester groups at least one hydrolyzable ester group, such as the esters of sulfuric acid, phosphoric acid, a lower alkane carboxylic acid (the term "lower” here and hereinafter means that the groups are alkyl radicals of 1 to 4 C) -Atoms contain or are), such as acetic acid, benzenesulfonic acid and their derivatives substituted on the benzene nucleus by substituents from the group of sulfo, carboxy, lower alkyl, lower alkoxy and nitro, such as p-toluenesulfonic acid and mesitylsulfonic acid (the acidic esters of sulfuric acid and phosphoric acid are also known as sulfato and phosphato groups, respectively, and correspond to general formula -OSO3M or -OPO3M2, in which M represents a hydrogen atom or an alkali metal, such as sodium, potassium or lithium
- the fiber-modifying compounds preferably contain only one ester group. If the fiber-modifying compounds do not contain an azacyclic radical, they preferably have at least one hydroxyl group.
- the compounds which cannot be used according to the invention have the general formula (A) (H2N) p - ALK - ER (A) in which p is the number 1 or 2, ER is an ester group and ALK is a straight-chain or branched alkylene radical of 2 to 6 carbon atoms which is optionally interrupted by 1 or more hetero groups and is not substituted by a hydroxyl group.
- the present invention thus relates to a process for dyeing fiber materials with water-soluble, anionic dyes, preferably with fiber-reactive dyes, which is characterized in that the dyeing is carried out using low-electrolyte or completely electrolyte-free and / or low-alkali or completely alkali-free dye solutions (dye liquors, printing pastes) and using a fiber material pretreated and modified with the above-mentioned compounds containing ester and amino groups.
- Such compounds containing ester and amino groups which can be used according to the invention are, for example, N- ( ⁇ -sulfatoethyl) piperazine, N- [ ⁇ - ( ⁇ '-sulfatoethoxy) ethyl] piperazine, N- ( ⁇ -sulfato- ⁇ -hydroxypropyl) -piperidine, N- ( ⁇ -sulfato- ⁇ -hydroxy-propyl) -pyrrolidine, N- ( ⁇ -sulfatoethyl) -piperidine, the salts of 3-sulfato-2-hydroxy-1- (trimethylammonium) propane, such as 3 -Sulfato-2-hydroxy-1- (trimethylammonium) propane sulfate, 2-sulfato-3-hydroxy-1-amino propane, 3-sulfato-2-hydroxy-1-amino propane, 1-sulfato-3 -hydroxy-2-amino-propane, 3-hydroxy-1-sulfato-2-amino-propane, 2,3
- Esterification and acylating agents which can be used to prepare the compounds containing ester and amino groups that can be used according to the invention from starting compounds are, for example, sulfuric acid, phosphoric acid, polyphosphoric acid, alkane carboxylic acids of 2 to 5 carbon atoms and their chlorides or anhydrides, such as acetic acid (glacial acetic acid ) and acetic anhydride, benzenesulfonic acid and those substituted on the benzene nucleus by substituents from the group consisting of sulfo, carboxy, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and nitro or benzenesulfonic acids or their sulfochlorides.
- the sulfato compound can be prepared from the corresponding hydroxy compounds by adding the hydroxy compounds in the required amount, ie preferably an equimolar amount, of concentrated sulfuric acid and stirring them at a temperature between 5 and 30 ° C for some time until the solution is complete. They are isolated from the sulfuric acid solution by pouring the solution onto ice and neutralization, by precipitating the sulfate ions using calcium carbonate as calcium sulfate and then filtering and evaporating the aqueous solution.
- the sulfato compounds can be obtained as crystalline or semi-crystalline substances which can be used directly in the process of modifying the fiber material.
- Fiber materials are understood to mean natural and synthetic fiber materials which contain hydroxyl and / or carbonamide groups, such as silk, wool and other animal hair, as well as synthetic polyemide fiber materials and polyurethane fiber materials, for example polyamide-4, polyamide-6 and polyamide-11, and in particular fiber materials which Base bodies of ⁇ , ⁇ -glucose contain, such as cellulose fiber materials, for example cotton, hemp, jute and linen, and their regenerated derivatives, such as viscose silk and rayon, or mixtures of such fiber materials.
- anionic dyes are meant those which are anionic, i.e. contain acidic groups, such as sulfo and carboxy groups, or their salts, such as alkali metal salts, and are accordingly water-soluble.
- anionic dyes which have a fiber-reactive group, i.e. a group that is usually able to react with the carbonamide or hydroxy groups of the fiber material and to be able to form a connection with them.
- the invention further relates to a process for modifying a fiber material, which is characterized in that a saturated aliphatic compound of 3 to 15 carbon atoms containing ester and amino groups and optionally substituted by 1 or 2 or more, such as 3 to 5, hydroxyl groups , preferably from 3 to 12 carbon atoms, with at least one primary, secondary, tertiary or quaternary amino group and at least one hydrolyzable ester group in which the aliphatic radical (s) is straight-chain, branched and / or cyclic ( are) and may optionally be interrupted by one or more, such as two or three, hetero groups, such as amino groups and oxygen atoms, and the amino group (s) can also be part of a saturated heterocyclic radical, with the exception of compounds of general formula (A), in aqueous, alkaline solution at a temperature between 60 and 230 ° C, preferably between n 90 and 190 ° C, can act on a fiber material.
- the invention relates to the use of such ester and amino group-containing compounds as defined above for modifying fiber materials, in particular with the aim of being able to use them for dyeing with water-soluble, anionic dyes without or only with small amounts of electrolyte salts and alkaline agents.
- the inventive method of modifying the fiber material can be carried out, for example, by contacting the fiber material with the aliphatic compound containing amino and ester groups in an alkaline aqueous solution.
- concentration of this compound in the alkaline aqueous solution is generally between 1 and 20% by weight, preferably between 5 and 10% by weight.
- the alkaline agent such as sodium hydroxide, sodium carbonate and potassium carbonate, can be present in a concentration between 1 and 20% by weight; the alkaline agent is preferably used in a concentration between 1.5 and 10% by weight, the amount depending both on the amount of use of the amino and ester group-containing aliphatic compound and on the material to be pretreated. This will avoid high alkali concentrations in polyester materials.
- the alkaline, aqueous solution containing the amino and ester group-containing aliphatic compound has a pH between 10 and 14.
- the fiber material which is both modified according to the invention and used in the modified form in the dyeing process according to the invention, can in all processing states, such as yarn, flake, sliver and piece goods (fabric), and also in a mixture with other fiber materials, such as in Form of cotton / polyester fiber materials and in the form of blended fabrics with other fiber materials.
- New compounds which can be used according to the invention are, for example, N- ( ⁇ -sulfato- ⁇ -hydroxypropyl) piperidine, N- ( ⁇ -sulfatoethyl) piperidine, N- ( ⁇ -sulfato- ⁇ -hydroxypropyl) piperidine, N - ( ⁇ -sulfato- ⁇ -hydroxypropyl) pyrrolidine, 3-sulfato-2-hydroxy-1-aminopropane, 2-sulfato-3-hydroxy-1-aminopropane, the salts of 2-sulfato- 3-hydroxy and 3-sulfato-2-hydroxy-1- (trimethylammonium) propane and their derivatives with an ester group other than the sulfato group.
- the aliphatic compounds containing ester and amino groups which can be used according to the invention can be brought into contact with the fiber material in a variety of ways in an alkaline aqueous solution, for example by treating the fiber material in an alkaline, aqueous solution of the compound containing ester and amino groups (analogous to a Dye-drawing process) at a temperature between 15 and 100 ° C, the modification of the fiber material already taking place, in particular at the higher temperatures, such as above 80 ° C.
- Other possibilities are to pad the fiber material with the aqueous, alkaline solution, to splash or to spray the solution onto the fiber material.
- the fiber material is impregnated with this alkaline, aqueous solution by introducing the fiber material into this solution or by padding (padding), the impregnated material is then squeezed off by excess liquor, so that the absorption of this aqueous, alkaline solution is between 50 and 120 % By weight, preferably between 70 and 100% by weight, based on the fiber material.
- the impregnation (by padding, splashing or treatment in the solution itself) takes place at a temperature between 10 and 60 ° C., preferably at a temperature between 15 and 30 ° C.
- a liquid absorption of preferably between 10 and 50% by weight is selected.
- the fiber material is a mercerized cellulose fiber material
- the compound containing amino and ester groups that can be used according to the invention can also advantageously be applied to the cellulose fiber material to be modified directly after the mercerization process, in which the mercerized material still contains the alkali, for example by using the one obtainable after the mercerization process.
- material impregnated with the aqueous alkali if necessary, squeezed to a required liquid content and the alkaline impregnated material impregnated with the aqueous solution of the compound containing amino and ester groups which can be used according to the invention, the impregnation being carried out by padding, spraying and similar process steps which are customary and known in the art can be.
- the impregnated material is dried; the drying of the fiber-modifying amino group-containing compound is carried out at the same time, a temperature between 100 and 230 ° C., preferably between 130 and 190 ° C., being chosen for the drying and fixing.
- a temperature between 100 and 230 ° C., preferably between 130 and 190 ° C., being chosen for the drying and fixing.
- drying and simultaneous fixing take place by treatment with hot air for 0.5 to 3 minutes.
- the fiber-modifying compound containing amino groups can also be fixed on the fiber material by simple drying at higher temperatures; it can be hung up in drying cabinets to dry and fix the modifying compound on the fiber material and exposed to the required higher temperatures, such as 80 to 105 ° C.
- the modified fiber material is aftertreated by rinsing with cold and hot water and optionally by treatment in an aqueous bath containing a small amount of an acid, such as acetic acid, to remove the alkali from the fiber material and then drying.
- a neutral-reacting fiber material should be used in the dyeing process if possible.
- the dyeing of fiber materials modified in this way is carried out analogously to known dyeing methods and printing processes for dyeing or printing fiber materials with water-soluble textile dyes, such as anionic dyes, in particular fiber-reactive dyes, and using the temperature ranges and customary amounts of dye known for this purpose, but with the exception according to the invention, that for the dyebaths, padding liquors and printing pastes of the dyeing process according to the invention, an addition of alkaline compounds, such as are usually used for fixing fiber-reactive dyes, such as sodium carbonate, potassium carbonate, sodium hydroxide solution and water glass, can be largely or completely excluded and that further the usual addition Electrolyte salts, which are intended in particular to increase the migration of the dye on the fiber, are not required or only to a small extent, for example up to a maximum of 10 g per liter of dye bath or dye liquor.
- the dyeing process according to the invention is accordingly carried out within a pH range between 4 and 8, preferably between 4.5 and 7.
- Dyeing processes which can be used according to the invention are, for example, the various extraction processes, such as dyeing on the jigger and on the reel runner or dyeing from a long or short liquor, dyeing in jet dyeing machines, dyeing using the pad-cold-dwell method or after a block-hot steam fixing process. With the pull-out process you can work in the usual liquor ratio of 1: 3 to 1:20.
- the dyeing temperature can be between 30 and 90 ° C, preferably it is at a temperature below 60 ° C; As can be seen from the above-mentioned application of the block-cold retention process according to the invention, dyeing is also advantageously possible at room temperature (10 to 30 ° C.).
- the use of the customary, often necessary dyeing aids such as surfactants (wetting agents), thiourea, thiodiethylene glycol, thickeners, leveling aids, auxiliaries which improve the solubility of dyes in the concentrated padding liquors, such as condensation products of formaldehyde and optionally alkyl-substituted Naphthalenesulfonic acids, and especially urea, can be omitted entirely or to a considerable extent.
- surfactants wetting agents
- thiourea thiodiethylene glycol
- thickeners thickeners
- leveling aids auxiliaries which improve the solubility of dyes in the concentrated padding liquors, such as condensation products of formaldehyde and optionally alkyl-substituted Naphthalenesulfonic acids, and especially urea
- the modified fiber material according to the invention can be dyed using a purely aqueous dye solution, in which only extremely small amounts of electrolyte salts (such as sodium chloride and sodium sulfate), which are contained in the dye powders as adjusting agents, are additionally dissolved.
- electrolyte salts such as sodium chloride and sodium sulfate
- the present invention can also be used advantageously for single-bath dyeing processes for dyeing mixtures of cellulose and polyester fibers, if in addition a disperse dye used for dyeing Polyester fiber materials is suitable, is used with a reactive dye in the common dye bath. Since many disperse dyes are sensitive to alkali, especially when using higher temperatures, they cannot be used in single-bath dyeing of cellulose / polyester mixed fiber materials, since the use of high temperatures in the alkali-containing bath in the dyeing of the polyester fiber by the disperse dye leads to damage to the disperse dye.
- the present invention makes it possible to dye free of alkali, so that in the aqueous, alkali-free dye liquor, the reactive dye can be fixed first at low temperature, for example at a dyeing temperature between 30 and 80 ° C., and then the polyester fiber with the disperse dye in the usual way at temperatures above 100 ° C, such as between 110 and 140 ° C, colored.
- All water-soluble, preferably anionic dyes which preferably have one or more sulfo and / or carboxy groups and which can optionally contain fiber-reactive groups, are suitable for the dyeing methods according to the invention.
- fiber-reactive dyes they can belong to the class of azo development dyes, direct dyes, vat dyes and acid dyes, which include, for example, azo dyes, copper complex, cobalt complex and chromium complex azo dyes, copper and nickel phthalocyanine dyes, anthraquinone and copper formazan - And triphendioxazine dyes.
- azo development dyes direct dyes
- vat dyes and acid dyes which include, for example, azo dyes, copper complex, cobalt complex and chromium complex azo dyes, copper and nickel phthalocyanine dyes, anthraquinone and copper formazan - And triphendioxazine dyes.
- azo dyes copper complex, cobalt complex and
- Fiber-reactive dyes are organic dyes which contain 1, 2, 3 or 4 fiber-reactive radicals from the aliphatic, aromatic or heterocyclic series. Such dyes have been extensively described in the literature.
- the dyes can belong to a wide variety of dye classes, such as the class of monoazo, disazo, polyazo, metal complex azo, such as 1: 1 copper, 1: 2 chromium and 1: 2 cobalt complex monoazo and disazo dyes, also the range of anthraquinone dyes, copper and cobalt phthalocyanine dyes, copper formazan dyes, azomethine, nitroaryl, dioxazine , Triphendioxazin, phenazin and stilbene dyes.
- Fiber-reactive dyes are understood to mean those which have a “fiber-reactive” group, ie a group which contains the hydroxyl groups of cellulose, the amino, carboxy, hydroxyl and thiol groups of wool and silk or the amino and possibly carboxy groups of synthetic polyamides are able to react to form covalent chemical bonds.
- the fiber-reactive residue can be bound to the dye residue directly or via a bridge member; preferably it is directly or via an optionally monoalkylated amino group, such as a group represented by the formula -NH-, -N (CH3) -, -N (C2H5) - or -N (C3H7) -, or via an aliphatic radical, such as one Methylene, ethylene or propylene radical or an alkylene radical of 2 to 8 carbon atoms, which can be interrupted by one or two oxi and / or amino groups, or via a bridge member containing an amino group, such as a phenylamino group, to the Dye residue bound.
- an optionally monoalkylated amino group such as a group represented by the formula -NH-, -N (CH3) -, -N (C2H5) - or -N (C3H7) -
- an aliphatic radical such as one Methylene, ethylene or propylene radical or an alkylene radical of 2
- Particularly interesting fiber-reactive radicals are fluorine and chloro-1,3,5-triazine radicals of the formula (2) in which Hal is chlorine or fluorine and Q is an amino, alkylamino, N, N-dialkylamino, cycloalkylamino, N, N-dicycloalkylamino, aralkylamino, arylamino, N-alkyl-N-cyclohexylamino, N- Alkyl-N-arylamino group or an amino group which contains a heterocyclic radical which may have a further fused-on carbocyclic ring, or amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring which optionally contains further heteroatoms, and hydrazino and semicarbazido groups , where the alkyl radicals mentioned can be straight-chain or branched and low molecular weight and higher molecular weight, preferably those having 1 to 6 carbon atoms.
- Suitable cycloalkyl, aralkyl and aryl radicals are, in particular, cyclohexyl, benzyl, phenethyl, phenyl and naphthyl radicals; Heterocyclic residues are especially furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole residues.
- the amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring are preferably residues of six-membered N-heterocyclic rings Compounds into consideration which may contain nitrogen, oxygen or sulfur as further heteroatoms.
- alkyl, cycloalkyl, aralkyl and aryl radicals, the heterocyclic radicals and the N-heterocyclic rings can additionally be substituted, for example by halogen, such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C1 -C4-alkyl, C1-C4-alkoxy, acylamino groups such as acetylamino or benzoylamino, ureido, hydroxy, carboxy, sulfomethyl or sulfo.
- halogen such as fluorine, chlorine and bromine
- sulfamoyl carbamoyl, C1 -C4-alkyl, C1-C4-alkoxy
- acylamino groups such as acetylamino or benzoylamino, ureido
- amino groups are: - NH2, methylamino, ethylamino, propylamino, isopropylamino, butylamino, hexylamino, ⁇ -methoxyethylamino, ⁇ -methoxypropylamino, ⁇ -ethoxyethylamino, N, N-dimethylamino, N, N-diethylamino, ⁇ -chloroethylamino , ⁇ -cyanoethylamino, ⁇ -cyanopropylamino, ⁇ -carboxyethylamino, sulfomethylamino, ⁇ -sulfoethylamino, ⁇ -hydroxyethylamino, N, N-di- ⁇ -hydroxyethylamino, ⁇ -hydroxypropylamino, benzylamino, phenethylamino, cyclohexylamino, phenyl,
- Q can be an amino radical of the general formula -NR10R11, in which R10 is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, and R11 is phenyl which is formed by a fiber-reactive radical of the vinylsulfone series directly or via a methylamino , Ethylamino, methylene, ethylene or propylene group is substituted and which can also be substituted by 1 or 2 substituents from the group methoxy, ethoxy, methyl, ethyl, chlorine, carboxy and sulfo, or R11 alkyl of 2 to 4 C- Atoms is, such as ethyl or n-propyl, which is substituted by a fiber-reactive group of the vinylsulfone series, or alkylenephenyl with an alkylene radical of 1 to 4 carbon atoms, the phenyl of which is substituted by a fiber-reactive radical of the vinylsulfone series
- Fiber-reactive groups of the vinyl sulfone series are those of the general formula -SO2-Y, in which Y is vinyl or ethyl which is substituted in the ⁇ -position by an alkaline eliminable substituent, such as, for example, chlorine, sulfato, phosphato, thiosulfato, acetyloxy, sulfobenzoyloxy and dimethylamino.
- an alkaline eliminable substituent such as, for example, chlorine, sulfato, phosphato, thiosulfato, acetyloxy, sulfobenzoyloxy and dimethylamino.
- the dyeings of the modified cellulose fiber materials obtainable in accordance with the invention require no further aftertreatment after removal from the dyebath or after completion of the fixation of the dye on the substrate, in particular no complex posttreatment process including washing.
- a fiber-reactive aftertreatment agent is advisable if the fiber material modified according to the invention has been dyed only in slight depths of shade or if a dye has been used which does not have satisfactory fiber reactivity. In these cases, there are still sufficient dye-reactive spots on the modified fiber, which, for example, can react with other dyes in rinsing baths contaminated with these dyes.
- This aftertreatment deactivates the still active areas of the fiber modified according to the invention, and one also obtains one contaminated with dyes in a technical process Rinse water the originally desired clear color.
- a final boiling treatment of the colored substrate with a washing solution to improve the fastness properties is not necessary.
- N- ( ⁇ -sulfato- ⁇ -hydroxy-propyl) piperidine 100 parts of N- ( ⁇ , ⁇ -dihydroxy-propyl) piperidine are slowly added to 67 parts of 100% sulfuric acid with stirring at 20 ° C. . The mixture is stirred for a further hour and the piperidine compound according to the invention is isolated in the manner described in Example A. It is initially obtained as an oily product which crystallizes after some time. It melts at 170 to 175 ° C with decomposition.
- N- ( ⁇ -sulfato- ⁇ -hydroxy-propyl) pyrrolidine 50 parts of N- ( ⁇ , ⁇ -dihydroxy-propyl) pyrrolidine in 98 parts of 100% sulfuric acid are slowly added with stirring at 20 ° C. . The batch is stirred for a further hour and the compound formed is then isolated as an oily product in the manner given in Example A.
- 1 H-NMR analysis in D6-dimethyl sulfoxide): 4.0 ppm (m, 1H); 3.76 / 3.68 ppm (2dd, 2H); 3.0 ppm (m, 2H); 1.95 ppm (s, br, 4H); 3.1 ppm (s, br, 4H).
- a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
- a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
- a mercerized and bleached cotton fabric is impregnated with an aqueous solution of 50 parts of sodium hydroxide and 100 parts of the monosulfate of 2,3-dihydroxy-1-aminopropane in 1000 parts of water at a temperature between 25 and 30 ° C with a liquor absorption of 85% and then treated to fix the aminopropane compound on the fiber material for about 3 minutes with hot air at 150 ° C., the impregnated fabric drying at the same time.
- the modified material is then freed from excess alkali by treatment with cold water at 60 ° C.
- the modified, dried material is dyed in a conventional exhaust process.
- 10 parts of this material in 200 parts by volume of an aqueous dye solution the 0.2 parts of a 50% electrolyte-containing dye powder of the dye of the formula known from German Offenlegungsschrift No. 24 12 964 contains dissolved.
- the dyeing takes place at 60 ° C. for 60 minutes.
- the dyed fabric is then rinsed with cold and warm water at 30 to 35 ° C, which may optionally contain a commercially available nonionic surfactant, then washed again with cold water and dried if necessary.
- a strong blue dyeing is obtained which, in terms of fastness properties and its other qualities, is similar to dyeings which are obtained using the customary dyeing methods of the prior art.
- a cotton fabric modified according to the information in Example 3a) is dyed in accordance with a pad-cold-dyed dyeing process.
- an aqueous dye solution containing 20 parts of 1000 parts by volume of a 50% electrolyte-containing dye powder of, for example, copper phthalocyanine dye of the formula known from German Patent No. 1,179,317 and contains 3 parts of a commercially available nonionic wetting agent dissolved, by means of a padder with a liquor absorption of 80%, based on the weight of the fabric, applied to the fabric at 25 ° C.
- the fabric padded with the dye solution is wound onto a dock, wrapped in a plastic film and left at 20 to 25 ° C for 16 hours and then with cold and hot water, which may or may not contain a commercially available wetting agent, and then again if necessary cold water rinsed and dried.
- a strong, uniformly colored turquoise coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
- a cotton fabric modified as described in Example 1 a) is printed with an aqueous printing paste containing 20 parts of the dye of the formula in 1000 parts (known from Example 258 of German Offenlegungsschrift No. 1 644 204) and contains 400 parts of an approximately 4% aqueous sodium alginate thickener.
- the printed cotton fabric is first dried at 60 to 80 ° C and then steamed for 5 minutes with superheated steam from 101 to 103 ° C, then treated by rinsing with cold and hot water, by boiling treatment in a bath containing a neutral, nonionic detergent, again rinsed with cold and hot water and dried.
- a uniform, scarlet-colored print is obtained which has good fastness properties.
- a cotton fabric modified as described in Example 1 a) is printed with an aqueous printing paste containing 20 parts of the dye of the formula in 1000 parts (known from Example 3 of German Offenlegungsschrift No. 2 557 141) and contains 400 parts of an aqueous, 4% strength sodium alginate thickener.
- the printed fabric is first dried at about 60 to 80 ° C and then steamed for 5 minutes with superheated steam at 101 to 103 ° C.
- 10 parts of a cotton fabric modified according to the information in Example 1 a) is represented by 200 parts of an aqueous solution of 0.2 part of the dye (known from Color Index under CI No. 51320).
- the cotton fabric is dyed in this dye solution for 60 minutes at 60 ° C.
- the aftertreatment of the dyeing obtained is carried out in a customary manner, for example analogously to the instructions in Example 6.
- a strong blue dyeing is obtained which has very good fastness to use, in particular good fastness to washing.
- Example 1a 10 parts of a cotton fabric modified as described in Example 1a is dissolved in 200 parts of an aqueous solution of 0.2 part of the copper phthalocyanine dye of the formula known, for example, from British Patent No. 1,046,520 given and dyed for 60 minutes at a dyeing temperature of 80 ° C.
- the dyeing obtained is then rinsed with cold and warm water at 30 to 35 ° C., which may contain a commercially available nonionic surfactant, and then rinsed again with cold water and dried. You get a high quality turquoise color with good fastness properties.
- a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
- a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
- a strongly colored red dyeing is obtained which, in terms of fastness properties and its qualities, is similar to dyeings which are obtained using the customary dyeing methods of the prior art.
- a fabric made of cotton tricot is treated with a solution of 50 parts of N- ( ⁇ -sulfatoethyl) piperidine and 50 parts of sodium hydroxide in 1000 parts of water for 30 minutes at 130 ° C. in a liquor ratio of 1:20. Then the modified material with cold and 60 ° C washed with hot water to remove excess alkali and dried.
- the modified cotton fabric obtained is dyed analogously to a conventional pull-out dyeing process: 100 parts of the fabric are placed in 2000 parts by volume of an aqueous dye solution which contains 2 parts of the 50% electrolyte-containing dye powder described in Example 1 dissolved. The fabric is moved therein and the dyebath is heated to 60 ° C. within 30 minutes and the dyeing is then continued at 60 ° C. for 60 minutes. The dyed material is removed from the bath and rinsed with cold and hot water, if appropriate with the addition of a commercially available wetting agent, if necessary then rinsed again with cold water and dried.
- a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
- 10 parts of a cotton jersey are treated in 200 parts of an aqueous solution of 10 parts of 3-sulfato-2-hydroxy-1- (trimethylammonium) propane sulfate and 5 parts of sodium hydroxide in a pressure vessel at 130 ° C. for 30 minutes.
- the modified material is then washed intensively and dried.
- 10 parts of this modified cotton fabric are in 200 parts of an aqueous solution of 0.2 parts of the dye of the formula known, for example, from German Offenlegungsschrift No. 19 43 904 dyed at 60 ° C for 60 minutes.
- the dyeing obtained is then rinsed with cold and warm water at 30 to 35 ° C., which may contain a commercially available nonionic surfactant, and then rinsed again with cold water and dried.
- a high-quality red coloring with good fastness properties is obtained.
- the modified cotton fabric obtained is dyed analogously to a conventional pull-out process:
- a strong, level, level red dyeing is obtained, the fastness properties of which are equivalent to the fastness of the dyeings obtainable by the methods of the prior art.
- a polyester / cotton blend fabric modified according to Example 19a) is treated in an HT dyeing machine with an aqueous dye liquor which, based on the weight of the dry fabric, contains 1.5% of the disperse dye known, for example, from German Laid-Open Specification No. 1 131 639 of the formula and contains 1.5% of the fiber-reactive azo dye described in Example 1.
- First dye at 60 ° C for 30 minutes and then after increasing to 130 ° C for a further 30 minutes at this temperature. The dyeing obtained is then completed in the manner given in Example 19b). A vivid orange color is obtained on both fiber parts.
- Example 20 The procedure of Example 20 is followed to produce a dyeing of a polyester / cotton blend, but using the disperse dye of the formula known, for example, from Japanese Patent Application Publication Sho-54-069139 and using the fiber-reactive copper phthalocyanine dye of the formula known, for example, from German Patent Application No. 1,283,997 and after the usual completion receives a lively blue-colored blended fabric with high level of coloration and with high fastness to use.
- 100 parts of a bleached cotton fabric are impregnated in a jigger with 1000 parts of an aqueous solution of 50 parts of N- ( ⁇ -sulfatoethyl) piperazine and 25 parts of sodium hydroxide at 95 ° C. for 30 minutes.
- the liquor is then drained off and the textile material in the same apparatus first in a conventional washing process, then in a dyeing process using 1500 parts of an aqueous solution with 2 parts of an approximately 50% electrolyte-containing dye powder, for example from example 106 of the European patent application.
- Publication No. 0 457 715 known fiber-reactive azo dye of the formula Subjected at 60 ° C for 30 minutes.
- the dyeing obtained is aftertreated and finished in the usual way. A strong red color with good general fastness properties is obtained.
- a cellulose fiber material modified according to the invention such as, for example, from a cellulose fiber material modified according to the above exemplary embodiments, and this using one of the customary dyeing methods, such as printing processes, exhausting methods or padding methods, for example analogously to one of the dyeing methods described in the above exemplary embodiments, subject to a dyeing process using one of the dyes specified in the following table examples, for example known from German specification No. 2,835,035 in the manner according to the invention, ie without the use of an alkali and without or only with very little use of an electrolyte, the dyeing process used Material can also be a modified cellulose fiber material in a mixture with a polyester fiber material. Based on the cellulose fiber material, strong, clear dyeings and prints are obtained with the hue given in the respective table example and the fastness properties good for the respective dye.
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TW223669B (xx) * | 1992-07-24 | 1994-05-11 | Hoechst Ag | |
TW228543B (xx) * | 1992-09-26 | 1994-08-21 | Hoechst Ag | |
TW360645B (en) * | 1992-11-21 | 1999-06-11 | Hoechst Ag | N-(2-sulfatoethyl) piperazine sulfate and it preparation |
DE4306432A1 (de) * | 1993-03-02 | 1994-09-08 | Hoechst Ag | Verfahren zum Bedrucken und Färben von Textilien (Inverser Reservedruck) |
DE4327301A1 (de) * | 1993-08-13 | 1995-02-16 | Hoechst Ag | Verfahren und Verwendung reaktiver Dispersionsfarbstoffe zum Färben oder Bedrucken aminierter, textiler Baumwoll- und Baumwoll-/Polyester-Mischgewebe |
DE4402210A1 (de) * | 1994-01-26 | 1995-07-27 | Hoechst Ag | Verfahren zur Herstellung aminierter Baumwollfasern |
ES2126794T3 (es) * | 1994-01-29 | 1999-04-01 | Dystar Textilfarben Gmbh & Co | Fibras sinteticas celulosicas aminadas. |
DE59502732D1 (de) * | 1994-05-17 | 1998-08-13 | Dystar Textilfarben Gmbh & Co | Aminierung von cellulosischen Synthesefasern |
DE4417211A1 (de) * | 1994-05-17 | 1995-11-23 | Hoechst Ag | Aminierung von Regeneratcellulose |
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DE4446540A1 (de) * | 1994-12-24 | 1996-06-27 | Hoechst Ag | Verfahren zur Herstellung von wasserlöslichen Aminoalkylderivaten von Polysacchariden |
DE19547649C2 (de) * | 1995-12-20 | 1999-05-06 | Dystar Textilfarben Gmbh & Co | Wäßrige Lösung von N-(2-Sulfatoethyl)piperazin-sulfat, Verfahren zu deren Herstellung und deren Verwendung zum Modifizieren von cellulosehaltigen Fasermaterialien |
DE19605578C2 (de) | 1996-02-15 | 2001-03-29 | Dystar Textilfarben Gmbh & Co | Verfahren zur Herstellung eines anionischen Textilfarbstoffen bedruckten textilen Materials |
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DE19859385A1 (de) | 1998-12-22 | 2000-06-29 | Basf Ag | Verfahren zur Herstellung von enzymhaltigen Granulaten |
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ES2471240T3 (es) * | 2002-05-24 | 2014-06-25 | Bayer Cropscience Ag | Procedimiento de preparación de derivados de tioalquilamina |
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JP5639347B2 (ja) * | 2009-06-18 | 2014-12-10 | 旭化成せんい株式会社 | ポリアミド繊維とセルロース繊維とポリウレタン繊維との混用糸状又は布帛染色品 |
JP5639348B2 (ja) * | 2009-06-18 | 2014-12-10 | 旭化成せんい株式会社 | ポリアミド繊維とポリウレタン繊維との混用糸条又は布帛の染色品 |
GB2526044A (en) * | 2014-01-10 | 2015-11-18 | Perachem Ltd | Methods relating to wool treatment |
CN104404761B (zh) * | 2014-11-13 | 2016-10-19 | 广东溢达纺织有限公司 | 一种防沾色纤维素纤维纱线、面料、成衣及其制备方法 |
CN104358154A (zh) * | 2014-11-26 | 2015-02-18 | 四川省宜宾惠美线业有限责任公司 | 纤维素纤维的无盐低碱染色工艺 |
CN104480751A (zh) * | 2014-11-26 | 2015-04-01 | 四川省宜宾惠美线业有限责任公司 | 纤维素纤维的无盐低碱染色方法 |
CN104452358A (zh) * | 2014-11-26 | 2015-03-25 | 四川省宜宾惠美线业有限责任公司 | 一种纤维素纤维的无盐低碱染色方法 |
CN104452355A (zh) * | 2014-11-26 | 2015-03-25 | 四川省宜宾惠美线业有限责任公司 | 纤维素纤维的阳离子化改性染色工艺 |
CN109736106A (zh) * | 2019-01-22 | 2019-05-10 | 乐清市雅格狮丹服饰有限公司 | 一种耐干洗大衣 |
CN114457596B (zh) * | 2022-03-22 | 2023-09-05 | 杭州卓达染整有限公司 | 一种针织醋酸面料的数码印花工艺 |
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GB8313348D0 (en) * | 1983-05-14 | 1983-06-22 | Procter & Gamble Ltd | Liquid detergent compositions |
GB2145726A (en) * | 1983-08-26 | 1985-04-03 | Diversey Corp | Surface active agents |
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US4721512A (en) * | 1985-11-25 | 1988-01-26 | Ciba-Geigy Corporation | Process for aftertreating dyed cellulosic material |
GB8609806D0 (en) * | 1986-04-22 | 1986-05-29 | Unilever Plc | Cleaning composition |
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ES2108040T3 (es) * | 1991-01-22 | 1997-12-16 | Procter & Gamble | Composicion para eliminar costras de carbonato de calcio. |
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-
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- 1992-11-17 TW TW081109199A patent/TW211595B/zh active
- 1992-12-03 FI FI925498A patent/FI925498A/fi not_active Application Discontinuation
- 1992-12-04 ES ES92120726T patent/ES2076657T3/es not_active Expired - Lifetime
- 1992-12-04 IL IL10398992A patent/IL103989A/en not_active IP Right Cessation
- 1992-12-04 TR TR92/1221A patent/TR26594A/xx unknown
- 1992-12-04 CZ CS923574A patent/CZ357492A3/cs unknown
- 1992-12-04 JP JP4325741A patent/JPH05295672A/ja not_active Withdrawn
- 1992-12-04 MX MX9207035A patent/MX9207035A/es not_active IP Right Cessation
- 1992-12-04 AU AU29919/92A patent/AU652870B2/en not_active Ceased
- 1992-12-04 PL PL92296847A patent/PL170575B1/pl unknown
- 1992-12-04 EP EP92120726A patent/EP0546476B1/de not_active Expired - Lifetime
- 1992-12-04 AT AT92120726T patent/ATE126290T1/de not_active IP Right Cessation
- 1992-12-04 DE DE59203225T patent/DE59203225D1/de not_active Expired - Fee Related
- 1992-12-04 DK DK92120726.2T patent/DK0546476T3/da active
- 1992-12-04 CA CA002084585A patent/CA2084585A1/en not_active Abandoned
- 1992-12-04 BR BR9204849A patent/BR9204849A/pt not_active IP Right Cessation
- 1992-12-05 CN CN92114122A patent/CN1046330C/zh not_active Expired - Fee Related
- 1992-12-05 KR KR1019920023418A patent/KR100240355B1/ko not_active IP Right Cessation
- 1992-12-06 EG EG75392A patent/EG20215A/xx active
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1995
- 1995-03-06 US US08/400,184 patent/US5507840A/en not_active Expired - Fee Related
- 1995-06-07 US US08/475,937 patent/US5575821A/en not_active Expired - Fee Related
- 1995-09-13 GR GR950402518T patent/GR3017393T3/el unknown
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Also Published As
Publication number | Publication date |
---|---|
GR3017393T3 (en) | 1995-12-31 |
IL103989A (en) | 1995-03-30 |
PL170575B1 (pl) | 1997-01-31 |
EP0546476A1 (de) | 1993-06-16 |
BR9204849A (pt) | 1993-06-08 |
DE59203225D1 (de) | 1995-09-14 |
ES2076657T3 (es) | 1995-11-01 |
CN1046330C (zh) | 1999-11-10 |
KR100241651B1 (ko) | 2000-03-15 |
FI925498A (fi) | 1993-06-08 |
AU2991992A (en) | 1993-06-10 |
KR100240355B1 (ko) | 2000-01-15 |
JPH05295672A (ja) | 1993-11-09 |
KR930013360A (ko) | 1993-07-21 |
CA2084585A1 (en) | 1993-06-08 |
ATE126290T1 (de) | 1995-08-15 |
CN1073943A (zh) | 1993-07-07 |
IL103989A0 (en) | 1993-05-13 |
DK0546476T3 (da) | 1995-12-27 |
MX9207035A (es) | 1993-06-01 |
PL296847A1 (en) | 1993-08-23 |
AU652870B2 (en) | 1994-09-08 |
US5507840A (en) | 1996-04-16 |
CZ357492A3 (en) | 1993-06-16 |
TW211595B (xx) | 1993-08-21 |
TR26594A (tr) | 1995-03-15 |
EG20215A (en) | 1997-11-30 |
US5575821A (en) | 1996-11-19 |
FI925498A0 (fi) | 1992-12-03 |
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