EP0051261A1 - Procédé pour réaliser des impressions au rongeant-réserve sur des matières textiles - Google Patents
Procédé pour réaliser des impressions au rongeant-réserve sur des matières textiles Download PDFInfo
- Publication number
- EP0051261A1 EP0051261A1 EP81109077A EP81109077A EP0051261A1 EP 0051261 A1 EP0051261 A1 EP 0051261A1 EP 81109077 A EP81109077 A EP 81109077A EP 81109077 A EP81109077 A EP 81109077A EP 0051261 A1 EP0051261 A1 EP 0051261A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- hydroxy
- substituted
- methoxy
- alkyl
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000004753 textile Substances 0.000 title claims abstract description 29
- 239000000463 material Substances 0.000 title claims abstract description 25
- 230000008569 process Effects 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000975 dye Substances 0.000 claims abstract description 76
- 238000007639 printing Methods 0.000 claims abstract description 63
- 238000005530 etching Methods 0.000 claims abstract description 59
- 239000000986 disperse dye Substances 0.000 claims abstract description 43
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 31
- 239000000835 fiber Substances 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- -1 methyl-substituted phenylsulfonyl Chemical group 0.000 claims description 170
- 125000004432 carbon atom Chemical group C* 0.000 claims description 75
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 27
- 239000003513 alkali Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000004744 fabric Substances 0.000 claims description 26
- 239000000985 reactive dye Substances 0.000 claims description 25
- 229920000728 polyester Polymers 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 15
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 229920003043 Cellulose fiber Polymers 0.000 claims description 5
- 229940079826 hydrogen sulfite Drugs 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052751 metal Chemical group 0.000 claims description 2
- 239000002184 metal Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 2
- LNQUWGZAZIOHMM-UHFFFAOYSA-N ethoxy-hydroxy-methoxy-lambda3-chlorane Chemical group CCOCl(O)OC LNQUWGZAZIOHMM-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000010019 resist printing Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 150000003254 radicals Chemical class 0.000 description 18
- 239000006185 dispersion Substances 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- CVXIRTCLVZZRKV-UHFFFAOYSA-N 1,4-dichlorophthalazine-6-carbonyl chloride Chemical compound ClC1=NN=C(Cl)C2=CC(C(=O)Cl)=CC=C21 CVXIRTCLVZZRKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 3
- 239000001000 anthraquinone dye Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940015043 glyoxal Drugs 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 2
- XJNDXSGINZSFDF-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=C(Cl)N=C(Cl)N=C1Cl XJNDXSGINZSFDF-UHFFFAOYSA-N 0.000 description 2
- DZTIFMWYYHCREC-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=CN=C(Cl)N=C1Cl DZTIFMWYYHCREC-UHFFFAOYSA-N 0.000 description 2
- PLVFHLAXDQSLCL-UHFFFAOYSA-N 2,6-dichloro-1h-triazin-4-amine Chemical compound NC1=NN(Cl)NC(Cl)=C1 PLVFHLAXDQSLCL-UHFFFAOYSA-N 0.000 description 2
- CTSJEGLSMYPRJK-UHFFFAOYSA-N 2,6-dichloro-n-methyl-1h-triazin-4-amine Chemical compound CNC1=NN(Cl)NC(Cl)=C1 CTSJEGLSMYPRJK-UHFFFAOYSA-N 0.000 description 2
- WULMCOUFBKKFQE-UHFFFAOYSA-N 2,6-dichloro-n-phenyl-1h-triazin-4-amine Chemical compound ClN1NC(Cl)=CC(NC=2C=CC=CC=2)=N1 WULMCOUFBKKFQE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- UGKIAJNNQAMSHX-UHFFFAOYSA-N 3,6-dichloropyridazine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NN=C1Cl UGKIAJNNQAMSHX-UHFFFAOYSA-N 0.000 description 2
- NZXOCWXWWQNPOF-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1Cl NZXOCWXWWQNPOF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000001005 nitro dye Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OZICRFXCUVKDRG-UHFFFAOYSA-N 2-[2-hydroxyethyl(propyl)amino]ethanol Chemical compound CCCN(CCO)CCO OZICRFXCUVKDRG-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NLVRKBJMZFTLFP-UHFFFAOYSA-N 3-chloropropanoic acid;hydrochloride Chemical compound Cl.OC(=O)CCCl NLVRKBJMZFTLFP-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000017309 Hypericum perforatum Nutrition 0.000 description 1
- 244000141009 Hypericum perforatum Species 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical group OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SIIHCIXCQJPDGU-UHFFFAOYSA-N [CH2]C(O)CO Chemical compound [CH2]C(O)CO SIIHCIXCQJPDGU-UHFFFAOYSA-N 0.000 description 1
- RQILFETZQXVWKX-UHFFFAOYSA-N ac1l570z Chemical compound C1=CC=C2N(C(C3=CC=C4C(=O)N(C(C=5C(C#N)=CC6=C3C4=5)=O)CCCOC)=O)C6=NC2=C1 RQILFETZQXVWKX-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000006009 dihaloalkoxy group Chemical group 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical class O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 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
- 125000005394 methallyl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910013664 m—(OCH2CH2)n—OH Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NPSSWQJHYLDCNV-UHFFFAOYSA-N prop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=C NPSSWQJHYLDCNV-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical group CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/15—Locally discharging the dyes
- D06P5/17—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/12—Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
Definitions
- the present invention relates to a method for the manufacture lu ng of ⁇ tzreservedrucken on textile materials consisting of hydbphoben fibers, preferably polyester fibers, or if such fibers in admixture with cellulose fibers contained, wherein to the textile material a confuseharmbarer disperse dye and optionally a bmwstoffbe responsibler disperse dye in the form of a dye liquor or applied printing paste and then dried or partially dried, is then printing and a discharge reserve printing paste, optionally containing in addition to the etchant or caustic resistant dyes in the desired pattern, and subsequent heat treatment at temperatures of 100-230 0 C.
- the textile material is colored at the printed areas by the indestructible dye.
- Colored prints on a dark background can also be obtained if the dark background is made with a mixture of an etchable and a differently colored, non-etchable dye.
- the dye can be dissolved in the hydrophobic fiber.
- the desired pattern is then printed on the dried or dried-on padded fabric with the etching printing paste and the padded and printed fabric is then subjected to a heat treatment, with the base dye immigrating into the polyester at the unprinted areas, i.e. is fixed and the dye is destroyed at the printed areas, i.e. no coloring takes place.
- this method is also called etching reserve pressure.
- etching reserve printing which is simple in itself, involves a number of technical difficulties which often make its use more difficult. It is usually not easy to completely destroy the base dye with the etchant. If this does not succeed, a colored residue remains on the etched areas, the shade of which can vary between yellow-brown and dull violet or reddish gray tones and which soils the white background at the etched areas. This leads to white etching which appears to be unclean or, in the event that a colored etching is to be produced, to a falsification of the shade of the etching-resistant dye.
- etching pastes which contain relatively strong reducing or oxidizing agents, such as sodium dithionite in combination with alkali, alkali formaldehyde sulfoxylates or even heavy metal salts, such as tin-2-chloride.
- strong etching agents such as sodium dithionite in combination with alkali, alkali formaldehyde sulfoxylates or even heavy metal salts, such as tin-2-chloride.
- this etchant are generally not bi l - lig, and in the case of Schwermetallrienstoff they represent an additional environmental burden or cause them additional expenses in sewage treatment.
- dyes that are resistant to such etchants, so that the selection of etch-resistant dyes that can be used to produce colored etchings is relatively small.
- Disperse dyes are required for the background coloring, which can be etched with pure white agents.
- Disperse dyes are known from German published patent application 26 12 740, 26 12 741, 26 12 742, 26 12 790, 26 12 791, 26 12 792 which contain at least two esterified carboxyl groups in their molecule. Such dyes saponify when treated with aqueous alkalis to form alkali-soluble dyes containing carboxylate groups.
- the use of such dyes as disperse dyes for dyeing polyester materials has the advantage that unfixed dye residues can be washed off the textile material by simple treatment with alkaline agents.
- the diazo or coupling components that are required for the production of dyes containing carboxylic acid ester groups are not common substances in the large chemical industry, but have to be produced separately for these types of dyes, which is generally uneconomical.
- the need to use pure white etchable dispersion dyes in the process of etching reserve printing on hydrophobic textile materials under relatively mild etching conditions could therefore not be satisfied by the types of dyes specified above.
- Y in addition also —NHCOZ, in which Z represents methyl, ethyl, propyl or i-propyl, which can be substituted by hydroxy, chlorine, bromine, cyano, phenyl or phenoxy or alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group, Alkyl with 2 to 8 carbon atoms, which is interrupted one to three times by oxygen and can be substituted by hydroxy, phenyl, amino, N-alkylamino with 1 to 4 carbon atoms, R 1 is hydrogen, alkyl with 1 - 4 C atoms by chlorine, bromine, cyan, by alkoxycarbonyl having 1 to 2 C atoms in the alkoxy group optionally substituted by hydroxyl, methoxy, ethoxy, chlorine, bromine or cyan, by alkanoyloxy having 2 to 4 C atoms Phenoxyacetoxy, monosubstituted by alkylaminocarbonyloxy having 1 to 4 carbon atom
- R 2 alkyl with 1 to 4 carbon atoms which is monosubstituted by chlorine, bromine, cyan, by alkanoyloxy with 2 to 4 carbon atoms, alkylaminocarbonyloxy with 2 to 4 carbon atoms or hydroxy or disubstituted by hydroxy or simultaneously by chlorine and hydroxy may be substituted, alkenyl having 3 to 4 carbon atoms or alkyl having 3 to 8 carbon atoms, the carbon chain of which is interrupted by 1 to 3 oxygen atoms and may be substituted one or more times by hydroxyl, chlorine, bromine or cyano,
- Etching reserve printing paste which contains a base as etchant which produces at least a pH of 8 in 5% strength aqueous solution.
- Alkyl or alkoxy radicals even if they are part of other radicals, can be straight-chain or branched.
- alkyl radicals with 1 to 4 carbon atoms in the alkylsulfonyl and dialkylphosphono substituents which can represent X 1 9 X 2 or X 3 are methyl, ethyl, propyl, butyl and i-butyl.
- substituents which can represent Y 1 are: hydrogen, chlorine, bromine, methyl, ethyl, propyl, i-propyl, n-butyl, butyl-2, i-butyl, t-butyl, hydroxymethyl, a- or ⁇ -hydroxyethyl, a-hydroxy-n-propyl, -i-propyl, -n-butyl, -butyl-2 or -i-butyl, dihydroxypropyl; Methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, i-butoxy, sec.-butoxy, ß-hydro xyethoxy, ⁇ -hydroxypropoxy, y-hydroxypropoxy, ⁇ -hydroxybutoxy, ⁇ -hydroxybutoxy, ⁇ , y-dihydroxypropoxy; Methoxycarbonylmethoxy, ethoxycarbonylmethoxy, 2- (methoxycarbonyl) ethoxy, 2-
- Substituents for which Y 2 can represent are, for example, hydrogen, chlorine, bromine; Methyl, ethyl, propyl, i-propyl, n-butyl, butyl-2, i-butyl, t-butyl; Hydroxymethyl, a- or ⁇ -hydroxyethyl, a-hydroxy-n-propyl, -i-propyl, -butyl, -butyl-2.
- Alkyl radicals for which R 1 and / or R 2 can stand are, for example, methyl, ethyl, propyl, i-propyl, n-butyl, i-butyl, sec-butyl; 2-chloro, 2-bromo or 2-cyanoethyl; 2- or 3-chloro, bromine or cyanopropyl; 2-, 3- or 4-chloro, bromine or cyanobutyl; 2,3-dihydroxypropyl, 2-hydroxy-3-chloropropyl; 2-acetoxy-, 2-propionyloxy- or 2-butyryloxyethyl, 2- or 3-acetoxy-, - propionyloxy- or-butyryloxypropyl, 3- or 4-acetoxy-, - propionyloxy- or-butyryloxy-butyl; Methyl, ethyl, propyl or butyl aminocarbonyloxethyl, methyl, ethyl, propyl or
- R 1 can furthermore be, for example: benzyl, phenethyl, phenoxyethyl, prop-3-yl, but-4-yl, but-3-yl or but-2-yl; Cyclohexyl, cyclopentyl; Methoxy, ethoxy, propoxy, hydroxyethoxy, chloroethoxy or methoxyethoxycarbonylethyl, carbonyl-1-methylethyl or carbonyl-2-methylethyl; 2-acetoxy, 2-propionyloxy or 2-butyryloxyethyl, 2- or 3-acetoxy, propionyloxy or butyryloxy propyl, 3- or 4-acetoxy, propionyloxy or butyryloxy butyl.
- Bases which are contained in the etching reserve printing paste as etching agents and which produce at least a pH of 8 in 5% aqueous solution are known in large numbers.
- bases are the hydroxides of the alkali and alkaline earth metals, salts of alkaline earth and alkali metals with weak organic or inorganic acids, such as, for example, alkali acetate, alkali metal carbonates or bicarbonates, trialkali phosphates, ammonia or else aliphatic amines, such as, for example, triethyl or tripropyl or tributylamine, ethanolamine, dinethyl- or diethylethanolamine, diethanolamine, methyl-, ethyl- or propyl-diethanolamine or triethanolamine.
- Alkaline earth metal hydroxides such as calcium hydroxide, alkali metal hydroxides such as sodium or potassium hydroxide, or alkali metal salts of weak inorganic acids such as sodium carbonate or trisodium phosphate are usually used as bases.
- the concentration of the base in the etching reserve printing pastes is expediently 25 to 250 g / kg, preferably 50 to 130 g / kg.
- the etching reserve printing pastes contain the usual additives contained in textile printing pastes, in particular thickeners such as alginates, starch products, synthetic polymeric thickeners, mineral oils, hydrotropic substances such as urea, as well as additives which promote wetting, penetration and dye absorption.
- thickeners such as alginates, starch products, synthetic polymeric thickeners, mineral oils, hydrotropic substances such as urea, as well as additives which promote wetting, penetration and dye absorption.
- nonionic detergents which are expediently contained in the etching reserve printing pastes, such as, for example, glycerol and / or polyglycols, such as polyethylene glycol with an average molecular weight of 300 to 400, is particularly favorable for the etching process.
- Preferred combinations X 1 / X 2 are nitro / methyl or ethylsulfonyl, nitro / trifluoromethyl, cyano / methyl or ethylsulfonyl, methylsulfonyl / methylsulfonyl, ethylsulfonyl / ethylsulfonyl.
- Very particularly preferred combinations X 1 / X 2 are nitro / cyan, nitro / nitro, nitro / methoxy or ethoxycarbonyl, cyan / cyan.
- Preferred combinations X 1 / X 2 / X 3 are methylsulfonyl / methylsulfonyl / alkoxycarbonyl, ethylsulfonyl / ethylsulfonyl / alkoxycarbonyl and nitro / methyl or ethylsulfonyl / alkoxycarbonyl, the alkoxy radical of the alkoxycarbonyl group carrying optionally substituted 1 to 4 carbon atoms.
- Very particularly preferred combinations of X 1 / X 2 / X 3 are N it ro / Cyan / Nitro, Nitro / nitro / Nitro, Nitro / Nitro / cyano, nitro / methoxy or ethoxycarbonyl / Nitro, Nitro / Cyan / optionally substituted alkoxycarbonyl, Nitro / nitro / optionally substituted alkoxycarbonyl, cyan / cyan / optionally substituted alkoxycarbonyl, nitro / nitro / aminosulfonyl or optionally substituted alkylaminosulfonyl, nitro / cyan / amino- or optionally substituted alkylaminosulfonyl or cyan / cyan / amino- or optionally substituted alkylaminosulfonyl.
- a further preferred group of dyes of the formula I comprises those dyes which are in the radicals R1 and / or R 2 and / or in the alkyl or alkoxy radicals which are Y1 or Y 2 and / or in the alkyl radicals which are Z stand, carry one or more hydroxyl groups.
- R1 and / or R 2 and / or in the alkyl or alkoxy radicals which are Y1 or Y 2 and / or in the alkyl radicals which are Z stand carry one or more hydroxyl groups.
- the 2-hydroxyethyl and the 2,3-dihydroxypropyl radical are particularly preferred.
- R 1 and R 2 are alkyl radicals with 3 to 8 carbon atoms, for Z alkyl radicals with 2 to 8 carbon atoms and for Y 1 and Y 2 alkoxy radicals with 3 to 8 carbon atoms, the carbon chain of the alkyl - and alkoxy radicals interrupted by 1 to 3 oxygen atoms and optionally substituted by hydroxy.
- Preferred dyes are also dyes of the general formula I which carry alkoxycarbonylalkyl groups in the radicals R 1 , Y 1 , Y and Z.
- Alkoxycarbonyl-methyl, alkoxycarbonyl-ethyl or alkoxycarbonyl-methylethyl radicals are particularly preferred for R 1 and alkoxycarbonyl- or alkoxycarbonyl-alkyl having 1 to 4 carbon atoms in the alkyl group for Z.
- Alkoxy radicals in the alkoxycarbonylalkyl groups which stand for R 1 or Z are preferably methoxy, ethoxy, i-propoxy, n-propoxy, methoxyethoxy or ethoxyethoxy.
- the process according to the invention is preferably suitable for textile materials which consist of hydrophobic fibers, in particular polyester fibers. However, it is also suitable for textile materials that predominantly use hydrophobic fibers alongside other fibers, e.g. Cell or cotton.
- the white-etchable disperse dyes of the formula I can be applied to the textile material in the form of liquors or printing pastes.
- the textile material is impregnated with the dye liquor in a manner known per se, for example padded or splashed.
- the dye liquors can be one or more disperse dyes of the formula 1 in addition to the known dyeing aids, such as dispersing agents agents, wetting agents, foam suppressants and block aids.
- the impregnated fabric web is squeezed to a liquor absorption of 50 to 120%.
- the fabric webs are then dried by warm air with any preceding infrared radiation, the temperature being approximately 80 ° C., maximum approximately 90 ° C. with a corresponding reduction in time.
- the fabric webs prepared in this way are then printed with an etching reserve printing paste which contains one of the bases specified in more detail above as an etching agent and the known additives, in particular thickening agents, which are customary in printing pastes for textile printing.
- the impregnated and printed fabric webs are then subjected to a heat treatment between 100 and 230 ° C. In the lower temperature range of approximately 100 to 110 ° C., the heat is preferably supplied by superheated steam. For heat treatments that are carried out between 160 and 230 ° C, hot air is preferably used as the heat transfer medium.
- the textiles are post-treated in the manner customary for polyester , rinsed hot and cold and dried.
- a particular embodiment of the process according to the invention consists in that the dye liquor contains, in addition to dispersion dyes of the formula I, one or more dispersion dyes which are alkali-resistant and are therefore not destroyed by the alkaline etching reserve printing pastes to be used according to the invention. If one proceeds as above, then multicolored designs are obtained.
- the disperse dyes of the formula I can also be printed onto the fabric in the form of printing pastes and then overprinted with the etching reserve printing paste.
- the textile prints are then fixed and finished as described above.
- multi-colored designs are obtained.
- etching reserve printing pastes which in turn contain alkali-resistant disperse dyes are printed on the fund impregnated or printed with disperse dyes of the formula I. With subsequent fixation and completion of the textile materials as described above, multicolored designs are also obtained here.
- etching reserve prints can be applied not only to textile materials which consist of hydrophobic fibers, in particular polyester fibers, or predominantly contain such fibers, but also to textile materials which contain hydrophobic fibers, in particular polyester fibers, and cellulose fibers in comparable proportions.
- Such polyester / cellulose blended fabrics can have, for example, a weight ratio of polyester / cellulose of 75:25, 65:35 or 50:50.
- the dye liquor or printing paste which contains at least one white-etchable disperse dye of the formula I and optionally one or more etch-resistant disperse dyes, also contains at least one etchable reactive dye with a reactive residue of formula or or or in which X is hydrogen or a metal cation, in particular the sodium cation, and Hal is halogen, in particular chlorine or bromine, and optionally contains one or more etch-resistant reactive dyes and if the etching reserve printing paste contains an alkali metal sulfate or alkali metal hydrogen carbonate and optionally an aldehyde, and if not otherwise, in addition to alkali metal carbonate or alkali metal hydrogen carbonate work as already stated.
- the etchable reactive dyes to be used contain one of the above-mentioned fiber-reactive radicals of the formulas II to V.
- the radicals of the formulas II to IV have in common that they are in the presence of alkali with the elimination of a sulfate or Halide anion form a vinylsulfonyl group. This group formed in the presence of alkali fixes on cotton or cellulose in the same way as the vinylsulfonyl radical of the formula V bonded directly to the dye radical by adding an OH group of the cellulose to the vinyl double bond.
- Etchable reactive dyes which have one of the reactive radicals mentioned above can belong to all technically important dye groups.
- Suitable reactive dyes are the monoazo dyes CI-Yellow 13 to 17 and 72 to 74, -Orange 7, 15, 16, 23, 24, 55, -Red 21 to 23, 35 36, 50, 63, 103 to 107, 112 to 114, -Blue 28, -Brown 16; the disazo dyes CI-Blue 76, -Blue 98, -Black 5, 31; the mono- or disazo metal complex dyes CI-Violet 4.5, -Blue 20, -Brown 18; the anthraquinone dyes CI-Violet 22, -Blue 19 and 27; the phthalocyanine dyes CI-Blue 21, 38, 77, 91 and Green 14 called.
- Particularly preferred as etchable reactive dyes are those which contain at least one fiber-reactive radical of the formulas III or IV as reactive anchor.
- the amounts of the disperse and reactive dyes which are contained in the padding liquors or printing pastes in the treatment of mixed fabrics are, as usual, matched to the depth of color of the desired color and intensity of the reactive effect.
- the amount of dyes suitable for one of the fiber types involved also corresponds to the mass fraction of this fiber type in the total fiber mass.
- a padding liquor which is prepared for a base dyeing of a certain color shade, in the case that the mixed fabric predominantly contains cellulose fibers, a high proportion of etchable and possibly non-etchable reactive dyes and a low proportion of etchable and possibly non-etchable dispersion dyes and in the case that the substrate predominantly Contains polyester fibers, a high proportion or only disperse dyes and a low proportion or no reactive dyes.
- an etching reserve printing paste is used which, in addition to alkali carbonate or alkali hydrogen carbonate, also contains an alkali sulfite or alkali hydrogen sulfite as a reservation agent for the reactive dyes.
- the alkali hydrogen sulfite can also be replaced in whole or in part by an equivalent amount of an alkali hydrogen sulfite-aldehyde adduct.
- alkali hydrogen sulfite alkali hydrogen carbonate and an aldehyde
- alkali hydrogen sulfite alkali hydrogen carbonate
- the sodium or potassium salts preferably the sodium salts
- Aldehydes which may be present in the reserve pastes as alkali metal bisulfite adducts are in principle all those which are technically readily accessible, such as, for example, formaldehyde, acetaldehyde, glyoxal, benzaldehyde.
- aldehyde-alkali hydrogen sulfite adducts are in equilibrium with the individual components of the adduct, preference is given to those aldehydes which, in the free state, do not have too high a vapor pressure and therefore cannot give rise to unpleasant odors.
- Glyoxal for example, is particularly suitable for the use according to the invention.
- the use of separately prepared addition compounds of these two components offers particular advantages in the preparation of printing pastes which contain sodium bisulfite in combination with an aldehyde.
- the use of such an adduct avoids the troublesome foaming that can occur in the most unfavorable cases when printing pastes containing alkali metal bicarbonate are produced.
- the concentration of the total of the reservation agents in the printing pastes is expediently 25 to 250 g / kg, preferably 50 to 130 g / kg.
- etching reserve prints on polyester / cellulose blended fabrics are the same as in the treatment of fabrics which consist of polyester or predominantly contain polyester.
- the heat treatment a) inhibits the etchable dispersion and reactive dyes at the points printed with the etching reserve printing paste and fixes any non-reservable dispersion and reactive dyes that are present, b) fixes the dispersion dyes at the points not printed with etching reserve printing paste, and, if so the padding liquor or printing paste contained an alkali metal formate, and at the same time a fixation of the reactive dyes.
- Inhibition of the dye is to be understood here as meaning the change in the dye molecule caused by the reservation agent, which leads to the dye in question no longer staining the substrate. In the two-phase process, i.e.
- the reactive dyes are then fixed in the base coloring, i.e. in the areas not printed with etching reserve printing paste, in a manner known per se. Finally, the dyeings or prints on the blended fabrics are rinsed hot and cold and dried.
- a particular embodiment of the process according to the invention on blended fabrics consists in that the padding liquor or printing paste contains, in addition to etchable disperse and reactive dyes, additionally etch-resistant disperse and reactive dyes, which are therefore those used according to the invention Etching reserve printing pastes cannot be destroyed. If one proceeds as above, then multicolored designs are obtained.
- a further possibility for carrying out the process according to the invention in mixed fabrics is that etching reserve printing pastes are printed on the fund, which are sealed or printed with reservable dyes, which in turn contain dispersing and reactive dyes which are resistant to the reservation agent. With subsequent fixation and completion of the textile materials as described above, multicolored designs are also obtained here.
- the disperse dyes of the formula I are present in the padding liquors or in the printing pastes in finely dispersed form, as is customary and known for disperse dyes, while the reactive dyes which may be present are dissolved.
- the padding liquors or printing pastes which are to be used in the process according to the invention are also prepared in a manner known per se by mixing the liquor or printing paste constituents with the necessary amount of water and liquid finely dispersed or solid redispersible formulations of the disperse dyes and solutions or formulations of reactive dyes.
- Disperse dyes which can be combined with the dye of the formula I to produce multicolored designs, are the known commercial dyes from the group of azo or azomethine, quinophthalone, nitro or anthraquinone dyes.
- alkali-resistant disperse dyes are:
- disperse dyes of the formula I to be used according to the invention are e.g. from German Offenlegungsschriften 12 90 915, 17 19 066, 18 09 920, 19 62 402, French Patents 145 833, 865 904, 816 950 and 1 465 508 and from Journal of the Chemical Society, Perkin I, 1979, p. 2634, known.
- the disperse dyes of the formula I can be prepared in a manner known per se by diazotization and coupling, as described, for example, in Swiss patent 615 938 or in German patent application 16 44 144. Some of the disperse dyes of the general formula I can also be prepared in a manner known per se so that an amine of the formula VI in which X 1 is chlorine, bromine, nitro, cyano, alkylsulfonyl having 1 to 4 carbon atoms or phenylsulfonyl and X 2 is chlorine or bromine, diazotized and on an amine of the formula VII couples and in the dye of formula VIII thus obtained in which X 1 is chlorine, bromine, nitro, cyan, alkylsulfonyl having 1 to 4 carbon atoms or phenylsulfonyl and X 2 is chlorine or bromine, the radical representing chlorine or bromine is cyan, nitro, alkylsulfonyl having 1 to 4 carbon atoms , Aryl
- 10 parts of the dye of the formula are added in finely divided form to a padding liquor which contains 905 parts of water, 5 parts of citric acid and 60 parts of an acrylic acid-based polymerization product as an anti-migration agent per 1000 parts.
- This padding liquor is used to pad a polyester fabric based on polyethylene glycol terephthalate at 20 to 30 ° C with a squeezing effect of approx. 80%.
- the padded fabric is carefully dried at 60 to 80 ° C. After drying is overprinted with a printing paste containing 500 parts of an aqueous 10% St. John's wort ether thickener, 260 parts of water, 80 parts of calcined sodium carbonate, 80 parts of polyethylene glycol 400 and 80 parts of glycerol per 1000 parts.
- Example 1 Instead of the dye in Example 1, 20 parts of the dye used and otherwise proceed as indicated in Example 1. A blue print is obtained with very good coloristic properties, in particular good fastness to light, dry heat fixation, rubbing and washing, and a very good white background with sharp contours at the etched areas.
- Example 1 Instead of the dye in Example 1, 20 parts of the dye of the formula used and otherwise proceed as indicated in Example 1. You get a red print with very good coloristic properties, especially good light, dry heat fixation, rub and wash fastness and a very good white background with sharp contours.
- Example 1 instead of the dye in Example 1, 20 parts of the dye of the formula used and otherwise proceed as indicated in Example 1. An orange-colored print is obtained with very good coloristic properties, in particular good light, dry heat fixation, rub and wash fastness and very good white background with sharp contours.
- a mercerized mixed fabric of polyester / cotton 65:35 is padded with a batch consisting of 100 parts of a 20% liquid setting of the dye of the formula 40 parts of the liquid commercial form of CI Reactive Blue 122, 808 parts of cold water, 10 parts of sodium m-nitrobenzenesulfonate, 20 parts of a polyacrylic acid-based antimigrant, 2 parts of monosodium phosphate, 20 parts of sodium formate.
- the stock thickener consists of 230 parts of an aqueous 4% alginate thickener, 80 parts of an aqueous 10% starch ether thickener, 85 parts of water, 25 parts of an aqueous 10% solution of the condensation product of polyglycol 2000 with stearic acid and 80 parts of heavy gasoline.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803041014 DE3041014A1 (de) | 1980-10-31 | 1980-10-31 | Verfahren zur herstellung von aetzreservedrucken von textilmaterialien |
| DE3041014 | 1980-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0051261A1 true EP0051261A1 (fr) | 1982-05-12 |
Family
ID=6115621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP81109077A Ceased EP0051261A1 (fr) | 1980-10-31 | 1981-10-28 | Procédé pour réaliser des impressions au rongeant-réserve sur des matières textiles |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4386935A (fr) |
| EP (1) | EP0051261A1 (fr) |
| JP (1) | JPS57106785A (fr) |
| DE (1) | DE3041014A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0121875A3 (fr) * | 1983-04-07 | 1984-12-19 | BASF Aktiengesellschaft | Procédé de production de teintures et d'impressions rongeables en milieu alcalin |
| US6173063B1 (en) * | 1998-10-06 | 2001-01-09 | Gn Resound As | Output regulator for feedback reduction in hearing aids |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3209329A1 (de) * | 1982-03-15 | 1983-09-15 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von ausbrenneffekten auf textilmaterialien |
| DE3209327A1 (de) * | 1982-03-15 | 1983-09-15 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von aetzreservedrucken auf hydrophoben textilmaterialien |
| US5908775A (en) * | 1995-09-14 | 1999-06-01 | Okasa Prefecture | Method of textile printing by microorganism and microorganism for decolorization of azo-system dye |
| US11566353B2 (en) | 2019-04-05 | 2023-01-31 | Nike, Inc. | Knit component with differing visual effects |
| CN113462190B (zh) * | 2021-06-30 | 2022-12-16 | 嘉禾宜事达(沈阳)化学有限公司 | 一种具有高水洗牢度的偶氮染料化合物、制备方法及应用 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341428A1 (de) * | 1973-08-16 | 1975-03-27 | Hoechst Ag | Verfahren zur erzeugung unregelmaessiger schattenfaerbungen auf polyesterfasern und deren mischungen |
| DE2341427A1 (de) * | 1973-08-16 | 1975-03-27 | Hoechst Ag | Verfahren zur herstellung von mehrfarbeneffekten |
| GB1543724A (en) * | 1975-08-13 | 1979-04-04 | Ici Ltd | Process for the production of discharge printing effects on synthetic textile materials |
| LU81059A1 (fr) * | 1978-03-17 | 1979-06-19 | Acna | Colorants monoazoiques insolubles dans l'eau et procede pour les preparer |
| DE3022429A1 (de) * | 1979-06-29 | 1981-01-08 | Sandoz Ag | Verfahren zum faerben von pes/cel mischtextilien |
| EP0023660A2 (fr) * | 1979-07-27 | 1981-02-11 | Hoechst Aktiengesellschaft | Procédé pour produire des effets de réserve sur des mélanges de fibres de polyester et de fibres cellulosiques |
| EP0036252A2 (fr) * | 1980-03-13 | 1981-09-23 | Imperial Chemical Industries Plc | Procédé d'impression de textiles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252580A (en) * | 1977-10-27 | 1981-02-24 | Messick Louis J | Method of producing a microwave InP/SiO2 insulated gate field effect transistor |
| DE2856283A1 (de) * | 1978-12-27 | 1980-07-17 | Cassella Ag | Verfahren zur herstellung von reserveeffekten auf polyester-zellulose-mischfaser-textilien |
| US4313731A (en) * | 1980-09-12 | 1982-02-02 | Mitsubishi Chemical Industries Limited | Mono-azo compound, mono-azo dye and dyeing process for polyester fibers |
-
1980
- 1980-10-31 DE DE19803041014 patent/DE3041014A1/de not_active Withdrawn
-
1981
- 1981-09-28 US US06/305,998 patent/US4386935A/en not_active Expired - Fee Related
- 1981-10-28 EP EP81109077A patent/EP0051261A1/fr not_active Ceased
- 1981-10-30 JP JP56173110A patent/JPS57106785A/ja active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341428A1 (de) * | 1973-08-16 | 1975-03-27 | Hoechst Ag | Verfahren zur erzeugung unregelmaessiger schattenfaerbungen auf polyesterfasern und deren mischungen |
| DE2341427A1 (de) * | 1973-08-16 | 1975-03-27 | Hoechst Ag | Verfahren zur herstellung von mehrfarbeneffekten |
| GB1543724A (en) * | 1975-08-13 | 1979-04-04 | Ici Ltd | Process for the production of discharge printing effects on synthetic textile materials |
| LU81059A1 (fr) * | 1978-03-17 | 1979-06-19 | Acna | Colorants monoazoiques insolubles dans l'eau et procede pour les preparer |
| DE3022429A1 (de) * | 1979-06-29 | 1981-01-08 | Sandoz Ag | Verfahren zum faerben von pes/cel mischtextilien |
| EP0023660A2 (fr) * | 1979-07-27 | 1981-02-11 | Hoechst Aktiengesellschaft | Procédé pour produire des effets de réserve sur des mélanges de fibres de polyester et de fibres cellulosiques |
| EP0036252A2 (fr) * | 1980-03-13 | 1981-09-23 | Imperial Chemical Industries Plc | Procédé d'impression de textiles |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, Band 83, Nr. 18, 3. November 1975, seite 97, Nr. 148990g Columbus, Ohio, U.S.A. & JP-A-50 050 478 (Toyobo Co., Ltd.) 06-05-1975 * |
| Research Disclosure, Band 198, Oktober 1980, seiten 415-416 Nr. 19827 Havant Hampshire, G.B. "A Process for the Discharge Printing of Aromatic Polyester Textile Materials" * insgesamt * * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0121875A3 (fr) * | 1983-04-07 | 1984-12-19 | BASF Aktiengesellschaft | Procédé de production de teintures et d'impressions rongeables en milieu alcalin |
| US6173063B1 (en) * | 1998-10-06 | 2001-01-09 | Gn Resound As | Output regulator for feedback reduction in hearing aids |
Also Published As
| Publication number | Publication date |
|---|---|
| US4386935A (en) | 1983-06-07 |
| JPS57106785A (en) | 1982-07-02 |
| DE3041014A1 (de) | 1982-06-16 |
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