EP0013378B1 - Procédé pour la réalisation d'effets de réserve sur des matières textiles fibreuses mixtes polyester-cellulose - Google Patents
Procédé pour la réalisation d'effets de réserve sur des matières textiles fibreuses mixtes polyester-cellulose Download PDFInfo
- Publication number
- EP0013378B1 EP0013378B1 EP79105182A EP79105182A EP0013378B1 EP 0013378 B1 EP0013378 B1 EP 0013378B1 EP 79105182 A EP79105182 A EP 79105182A EP 79105182 A EP79105182 A EP 79105182A EP 0013378 B1 EP0013378 B1 EP 0013378B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- bromine
- alkyl
- chlorine
- weight
- 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
Links
- 238000000034 method Methods 0.000 title claims description 33
- 230000008569 process Effects 0.000 title claims description 25
- 239000004753 textile Substances 0.000 title claims description 21
- 239000000463 material Substances 0.000 title claims description 20
- 230000000694 effects Effects 0.000 title claims description 16
- 229920002678 cellulose Polymers 0.000 title claims description 9
- 239000001913 cellulose Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 cyano, hydroxyl Chemical group 0.000 claims description 108
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 239000000975 dye Substances 0.000 claims description 56
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 40
- 229910052794 bromium Inorganic materials 0.000 claims description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 39
- 238000007639 printing Methods 0.000 claims description 37
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229920000742 Cotton Polymers 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000010695 polyglycol Substances 0.000 claims description 6
- 229920000151 polyglycol Polymers 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Chemical group 0.000 claims description 3
- 239000002184 metal Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000000985 reactive dye Substances 0.000 description 38
- 239000003513 alkali Substances 0.000 description 27
- 239000000986 disperse dye Substances 0.000 description 27
- 238000005530 etching Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000835 fiber Substances 0.000 description 18
- 239000004744 fabric Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229920003043 Cellulose fiber Polymers 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 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 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- 229940015043 glyoxal Drugs 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229940079826 hydrogen sulfite Drugs 0.000 description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000004584 polyacrylic acid Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000004280 Sodium formate Substances 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 4
- 235000019254 sodium formate Nutrition 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001000 anthraquinone dye Substances 0.000 description 3
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 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 2
- 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
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 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
- CGIHHZTTZZMCRK-UHFFFAOYSA-N 3-chloroquinoxaline-6-carbonyl chloride Chemical compound N1=CC(Cl)=NC2=CC(C(=O)Cl)=CC=C21 CGIHHZTTZZMCRK-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 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 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 125000003118 aryl 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
- 150000001875 compounds Chemical class 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 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 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 239000001005 nitro dye Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229920001522 polyglycol ester Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 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
- 230000009467 reduction Effects 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JGIGXKSJLSQJGQ-UHFFFAOYSA-K trisodium 5-[[4-chloro-6-(N-methylanilino)-1,3,5-triazin-2-yl]amino]-4-hydroxy-3-[(2-sulfonatophenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].CN(c1ccccc1)c1nc(Cl)nc(Nc2cc(cc3cc(c(N=Nc4ccccc4S([O-])(=O)=O)c(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)n1 JGIGXKSJLSQJGQ-UHFFFAOYSA-K 0.000 description 2
- OXLITIGRBOEDEZ-UHFFFAOYSA-N 1,5-diamino-4,8-dihydroxy-2-(4-hydroxyphenyl)anthracene-9,10-dione Chemical compound C=1C(O)=C2C(=O)C=3C(N)=CC=C(O)C=3C(=O)C2=C(N)C=1C1=CC=C(O)C=C1 OXLITIGRBOEDEZ-UHFFFAOYSA-N 0.000 description 1
- ZRDUNOGZJOMOGI-UHFFFAOYSA-N 1-[5-[(3,6-dichloropyridazine-4-carbonyl)amino]-2-methyl-3-sulfophenyl]-5-oxo-4-[(2-sulfophenyl)diazenyl]-4h-pyrazole-3-carboxylic acid Chemical compound C1=C(S(O)(=O)=O)C(C)=C(N2C(C(N=NC=3C(=CC=CC=3)S(O)(=O)=O)C(=N2)C(O)=O)=O)C=C1NC(=O)C1=CC(Cl)=NN=C1Cl ZRDUNOGZJOMOGI-UHFFFAOYSA-N 0.000 description 1
- WPNCZPHIKSFVSG-UHFFFAOYSA-N 1-amino-4-[3-[(3,6-dichloropyridazine-4-carbonyl)amino]-2,4,6-trimethyl-5-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound CC1=C(S(O)(=O)=O)C(C)=C(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(N)=C(C=2)S(O)(=O)=O)C(C)=C1NC(=O)C1=CC(Cl)=NN=C1Cl WPNCZPHIKSFVSG-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- SPSSDDOTEZKOOV-UHFFFAOYSA-N 2,3-dichloroquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=NC2=C1 SPSSDDOTEZKOOV-UHFFFAOYSA-N 0.000 description 1
- 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
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-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
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-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
- JADVVTZXHQUFLS-UHFFFAOYSA-N 3,4-dichloropyridazine Chemical group ClC1=CC=NN=C1Cl JADVVTZXHQUFLS-UHFFFAOYSA-N 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
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- ZCMWRFQVYXHUQN-UHFFFAOYSA-N 4,11-diamino-1-imino-2-(3-methoxypropyl)naphtho[2,3-f]isoindole-3,5,10-trione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(N(CCCOC)C1=N)=O)C1=C2N ZCMWRFQVYXHUQN-UHFFFAOYSA-N 0.000 description 1
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-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
- WLJUQHJNPIQOMP-UHFFFAOYSA-N C(#N)BrCl Chemical compound C(#N)BrCl WLJUQHJNPIQOMP-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 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
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006226 butoxyethyl group 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
- 150000001735 carboxylic acids Chemical class 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
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- 150000002148 esters Chemical class 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 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
- 230000003165 hydrotropic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000434 metal complex dye Substances 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
- BYMNHMLASYXHRV-UHFFFAOYSA-N methyl 3-[3-acetamido-n-(3-methoxy-3-oxopropyl)-4-[(4-nitrophenyl)diazenyl]anilino]propanoate Chemical compound CC(=O)NC1=CC(N(CCC(=O)OC)CCC(=O)OC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 BYMNHMLASYXHRV-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- BUFTYJOYPAXWBW-UHFFFAOYSA-N n-chlorotriazin-4-amine Chemical compound ClNC1=CC=NN=N1 BUFTYJOYPAXWBW-UHFFFAOYSA-N 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
- 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
- 125000004344 phenylpropyl group Chemical group 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 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
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-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
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 159000000000 sodium salts Chemical class 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
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YFIWOVRNIAJHTA-UHFFFAOYSA-K trisodium 7-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]-methylamino]-4-hydroxy-3-[(4-methoxy-2-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].COc1ccc(N=Nc2c(O)c3ccc(cc3cc2S([O-])(=O)=O)N(C)c2nc(Cl)nc(Nc3ccc(cc3)S([O-])(=O)=O)n2)c(c1)S([O-])(=O)=O YFIWOVRNIAJHTA-UHFFFAOYSA-K 0.000 description 1
- DLPITEUCXDBWSF-UHFFFAOYSA-K trisodium N-[8-oxido-7-[[2-oxido-4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]-3,6-disulfonaphthalen-1-yl]ethanimidate Chemical compound CC(=NC1=C2C(=CC(=C1)S(=O)(=O)O)C=C(C(=C2[O-])N=NC3=C(C=C(C=C3)S(=O)(=O)CCOS(=O)(=O)O)[O-])S(=O)(=O)O)[O-].[Na+].[Na+].[Na+] DLPITEUCXDBWSF-UHFFFAOYSA-K 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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 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 by introducing both types of dye into the padding liquor.
- German Patent Specification 2,326,522 describes a process for producing reserve effects with reactive dyes on native or regenerated cellulose fiber materials.
- the textile material is printed with sulfites, thiosulfates or thioureas as a reservation agent, alkalis as a fixing agent and reactive dyes, which a) react with the reservation agent and have the ß-sulfatoethylsulfonyl or ß-sulfatoethylsulfonamide group as reactive group and b) do not have on fixing react with the reservation agents and have as a reactive group the chloraminotriazine, dichloropyrimidine, trichloropyrimidine, dichlorotriazine, monochlorotriazine, quaternized chlorotriazine or the dichloropyridazine group, in the form or overpressure process, then dries and fixes the dyes by steaming or Hot air treatment.
- the known etching printing process is therefore modified in such a way that the textile material is first padded with a dye liquor containing disperse dye and reactive dye and dried or dried, but no fixation of the Dye, that is, solution of the disperse dye in the hydrophobic fiber, may take place.
- the desired pattern is then printed on the dried or dried-on padded fabric with the etching paste, and the padded and printed fabric is then subjected to a heat treatment, at the same time the base dye immersed in the non-printed areas in the polyester and the reactive dye is fixed on the cellulose and the dye is destroyed at the printed areas, ie no coloring takes place.
- this method is also referred to as 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 fluctuate between yellow-brown and dull violet or reddish gray tones and which soils the white background at the etched areas. This leads to white etchings which appear to be unclean or, in the event that a colored etch is to be produced, to a falsification of the shade of the etchant-resistant dye. To overcome this difficulty, etching pastes are used which contain relatively strong reducing or oxidizing agents, such as. B.
- Alkyl radicals with 1 to 6 carbon atoms, which R 1 in formula I can represent, are, for example, methyl; Ethyl; Propyl; Isopropyl; Butyl; 1- and 2-isobutyl; Pentyl- (1), - (2) and - (3); 2- or 3-methylbutyl- (1) or - (2); Hexyl- (1), - (2) or- (3); 1-, 2- or 3-ethylbutyl- (1) or - (2); 2-, 3- or 4-methylpentyl- (1).
- substituents for which X 1 in formula I can stand are: chlorine; Bromine; Ethyl; Methyl; Propyl; Isopropyl; Butyl- (1) or - (2); Isobutyl; ⁇ -chloro, bromine, cyano or hydroxyethyl; ⁇ -chloro, bromine, cyano or hydroxypropyl; y-chloro, bromine, cyan or hydroxypropyl; ⁇ - or y-chloro, bromine, cyano or hydroxybutyl (1); 3-chloro, bromine, cyan or hydroxybutyl (2); Methoxy, ethoxy, propoxy, isopropoxy; But-1-or-2-oxy; Isobutoxy; ⁇ -hydroxyethoxy; ⁇ - or ⁇ -hydroxypropoxy; Hydroxyisopropoxy; ⁇ -, y- or ⁇ -hydroxybutoxy; Hydroxyisobutoxy; ß-methoxyethoxy; ß-
- substituents which Y 1 can represent are: methyl; Ethyl; Propyl- (1) or - (2); n-butyl- (1) or - (2); Isobutyl- (1), - (2) or - (3); 2-chloroethyl; 2-chloropropyl; 3-chloropropyl; 2-bromoethyl; 2-cyanoethyl; 2-cyanopropyl; 3-cyanopropyl; 1- or 2-hydroxyethyl; 2- or 3-hydroxypropyl- (1); Methoxy; Ethoxy; Propoxy; Isopropoxy; Butoxy; Isobutoxy; ⁇ -hydroxyethoxy; 2- or 3-hydroxypropoxy; 2- or 4-hydroxy-but-2-oxy; Methoxyethoxy; Athoxymethoxy; 2- or 3-methoxyprop-1-oxy; 2- or 3-ethoxyprop-l-oxy; 2- or 4-methoxybut-1-oxy; 2- or 4-ethoxybut-1-oxy; 4-methoxybut-1-oxy; 2-
- Optionally substituted lower alkyl groups with 1 to 6 carbon atoms are for example: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl-1, -2 or -3, Hexyl-1, -2 or -3, 2-chloro, bromine or cyanoethyl, 2- or 3-chloro, bromine or cyanopropyl- (1); 2-, 3- or 4-chloro, bromine or cyanobutyl- (1); 1-, 3- or 4-chloro, bromine or cyanobutyl- (2); Methoxy, ethoxy, propoxy, isopropoxy or butoxyethyl; ß- (ß-Hydroxyethoxy) ethyl; 2- or 3-methoxy or ethoxy propyl (1); Benzyl; Phenethyl; Phenylpropyl; Acetyloxy, pro
- Alkenyl groups which R 2 or R 3 represent are, for example: allyl; Methallyl; Crotyl; Buten-3-yl- (1); Buten-3-yl- (2); Penten-2-, -3- or -4-yl- (1); Penten-3- or -4-yl- (2); Hexen-2-, -3-, -4-or -5-yl- (1).
- Dyes of the formula I in which R 1 is hydrogen and R 2 is free from alkoxycarbonyl and hydroxyalkoxycarbonyl groups are particularly preferred for use in the process according to the invention.
- Another preferred group of dyes of the formula I comprises those dyes which contain hydroxyl groups in the radicals R 2 and / or R 3 , in particular those in which R 2 is ethyl or ⁇ -hydroxyethyl and R 3ß -hydroxyethyl.
- Another class of disperse monoazo dyes which is particularly preferred for the use according to the invention are the dyes of the formula wherein X 1 is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxyalkoxy with a total of 3 to 6 carbon atoms, hydroxyalkyl with 2 to 4 carbon atoms, chlorine; Y 1 represents chlorine, alkyl having 1 to 4 carbon atoms or - NH - CO - Y 2 and R i , R 2 , R 3 and Y 2 have the meanings given above.
- Preferred -NH-CO-Y 2 groups are alkanoylamino groups with unsubstituted alkanoyl radicals with 2 to 4 carbon atoms, in particular acetylamino groups.
- dyes which have a combination of preferred features are particularly preferred for use in the process according to the invention wherein R 2 is ethyl or ⁇ -hydroxyethyl, or dyes of the formulas
- the dyes of the formula II used in the process according to the invention and their preparation are known from German Offenlegungsschrift 2,612,741. They can exist in a number of possible tautomeric forms. For the sake of convenience, the dyes are only formulated in one of the possible forms. However, it should be noted that the invention also encompasses the use of dyes in any of the possible tautomeric forms.
- lower alkyl and “lower alkoxy” refer to alkyl or alkoxy radicals having 1 to 4 carbon atoms.
- substituents which may be present on the phenyl radical D are lower alkyl radicals, such as. As methyl, lower alkoxy radicals, such as. B. methoxy and ethoxy, lower alkylcarbonyl radicals, such as. B. acetyl, lower alkyl sulfonyl radicals, such as. B. ethyl sulfonyl, lower alkylcarbonylamino radicals, such as. B. acetylamino, N-lower alkyl and N, N-di-lower alkylcarbamoyl radicals, such as. B.
- B. N-ethyl sulfamoyl and N, N-dimethyl sulfamoyl, N-lower alkyl and N, N-di-lower alkyl sulfamato radicals (-O ⁇ S0 2 NH 2 ), such as. B.
- N-methylsulfamato and N, N-diethylsulfamato, examples of lower alkyl radicals X 2 and Z are ethyl and methyl.
- examples of lower alkylcarbonyl radicals X 2 are acetyl and propionyl.
- An example of a lower alkyl sulfonyl radical X 2 is ethyl sulfonyl.
- An example of a lower alkylcarbonylamino radical X 2 is acetylamino.
- the reactive dyes used in the process according to the invention contain one of the fiber-reactive radicals of the formulas III to VI given above. It is common to the radicals of the formulas 111 to V that they form a vinylsulfonyl group in the presence of alkali with the elimination of a sulfate or halide anion. This group formed in the presence of alkali fixes in the same way as the vinylsulfonyl radical of the formula V which is bonded directly to the dye radical by adding one of the OH groups of the cellulose to the vinyl double bond. Reactive dyes that have one of the reactive radicals mentioned above can all technically important dye groups belong to.
- Examples of reactive dyes which are suitable for carrying out the process according to the invention are the monoazo dyes CI-Yellow 13-17 and 72-74, Orange 7, 15, 16, 23, 24, 55, Red 21-23, 35, 36 , 50, 63, 103-107, 112-114, 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.
- etchable reactive dyes are those which contain at least one fiber-reactive radical of the formulas IV or V as reactive anchor.
- the amounts of the dyes which are contained in the padding liquors to be used according to the invention are, as usual, matched to the depth of color of the desired color and intensity of the reserve 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 that is prepared for a base color of a certain shade contains, in the event that the substrate 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 disperse dyes, and in the event that Substrate mainly contains polyester fibers, a high proportion of disperse dyes and a low proportion of reactive dyes.
- the method according to the invention is primarily intended for the finishing of textiles made of cellulose polyester fibers.
- the quantity ratio of the two types of fibers is not subject to any restrictions, taking into account the criteria given above for the composition of the padding liquor, and in the limit case, the process can also be used to produce reserve effects on pure cellulose textiles or pure polyester textiles, in which case the padding liquors are exclusively etchable and optionally contain non-etchable reactive dyes or exclusively etchable and possibly non-etchable disperse dyes.
- the reserve paste to be used in carrying out the process according to the invention contains either an alkali sulfite or an alkali hydrogen sulfite in combination with alkali carbonate or alkali hydrogen carbonate as a reservation agent.
- the alkali hydrogen sulfite can also be replaced in whole or in part by an equivalent amount of an alkali hydrogen sulfite-aldehyde adduct. It is also possible to produce this adduct in the reserve paste itself by adding alkali hydrogen sulfite, alkali hydrogen carbonate and an aldehyde to the reserve paste.
- alkali sulfite alkali hydrogen sulfite and alkali hydrogen carbonate
- the sodium or potassium salts preferably the sodium salts
- aldehydes which can be contained as alkali hydrogen sulfite adducts in the reserve pastes, come in principle all technically easily accessible, such as. B. formaldehyde, acetaldehyde, glyoxal, benzaldehyde, into consideration.
- 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 reservation agent in the printing pastes is expediently 25 to 250 g / kg, preferably 50 to 130 g / kg, calculated on sodium bisulfite.
- the reserve pastes contain, in addition to the reservation agents mentioned, the usual additives contained in textile printing pastes, in particular thickeners, such as. B. alginates, starch products, synthetic polymeric thickeners, mineral oils, hydrotropic substances such as urea, and wetting, penetration and dye-promoting additives.
- thickeners such as. B. alginates, starch products, synthetic polymeric thickeners, mineral oils, hydrotropic substances such as urea, and wetting, penetration and dye-promoting additives.
- nonionic detergents which can expediently be contained in the etching printing pastes, is particularly favorable for the etching process.
- z. B. glycerol and / or polyglycols such as polyethylene glycol with an average molecular weight of 300 to 400.
- the process according to the invention is carried out in a manner known per se by padding the textile material composed of polyester and cellulose fibers with dye liquors, the one or more of the above-mentioned alkali-etchable disperse dyes and one or more reactive dyes fe which have one of the above-mentioned reactive radicals of the formulas 111 to VI, preferably the ß-sulfatoethylsulfonyl or ß-sulfatoethylsulfonamide groups, in addition to the known customary dyeing aids, such as, for example, dispersants, wetting agents, foam suppressants and padding aids and, if colored etching prints are to be produced , additionally contain dispersing and reactive dyes that are resistant to the etchant, and squeezing the padded fabric webs to a liquor absorption of 50-120%.
- the customary dyeing aids such as, for example, dispersants, wetting agents, foam suppressants and padding aids and, if colored
- the fabric webs are then dried by warm air with any preceding infrared radiation, the temperature being approximately 80 to a maximum of approximately 150 ° C. with a corresponding reduction in time.
- the fabric webs prepared in this way are then printed with the etching reserve printing paste, which contains the reservation agents described above and the additives known in printing pastes for textile printing, in particular thickeners.
- the padded and printed textile fabrics are subjected to a heat treatment between 100 and 190 ° C.
- the heat is preferably supplied by superheated steam.
- the heat treatment causes a) an inhibition of the reservable disperse and reactive dyes at the points printed with the reserve paste and a fixation of the possibly available, non-reservable dispersion and reactive dyes, b) a fixation of the disperse dyes at the points not printed with the reserve paste and, if so the padding liquor contained an alkali metal formate, including the reactive dyes.
- Inhibition of the dye is to be provided with the change in the dye molecule caused by the reservation agent, which leads to the dye in question no longer staining the substrate.
- the reactive dyes are then fixed in the base coloring, ie at the points not printed with reserve paste.
- the dyeings or prints are rinsed hot and cold and dried.
- a special embodiment of the method according to the invention consists in that the padding liquor contains, in addition to reservable disperse and reactive dyes, those which are resistant to the reservation agent and are therefore not destroyed by the etching reserve printing pastes to be used according to the invention. If you proceed as indicated above, you get multi-colored designs.
- a further embodiment of the method according to the invention is that the reservable dyes are not applied to the entire fabric by padding with a pad liquor, but are also printed on the fabric in the form of printing pastes and then overprinted with the etching reserve printing paste. The textile prints are then fixed and completed as described above.
- 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 are dissolved.
- the padding liquors or printing pastes which are to be used 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 settings of the disperse dyes and solutions or settings of the reactive dyes.
- Disperse dyes which are resistant to the reservation agent and which can be combined with the reservable dye of the formula to produce multicolored designs are the known commercial dyes from the group of azo or azomethine, quinophthalone, nitro or anthraquinone dyes.
- Some examples of resistant disperse dyes are:
- a mercerized blended fabric made of polyester-cotton 50:50 is padded with a fleet of 20 parts by weight of the liquid commercial form of 5- (4-nitro-2-methylphen-1-yl) -azo-4-methyl-3-cyan-2, 6-dihydroxypyridine, 20 parts by weight of the liquid commercial form of CI Disperse Violet 48, 40 parts by weight of the commercial form of a mixture of 40% by weight C.I. Reactive Yellow 17 and 60% by weight C.I. Reactive Violet 5, 200 parts by weight of water at 80 ° C., 687 parts by weight of water cold, 10 parts by weight of sodium m-nitrobenzenesulfonate, 20 parts by weight of an anti-migration agent based on polyacrylic acid and 3 parts by weight of monosodium phosphate.
- a printing paste which is produced as follows: 30 parts by weight of the commercial form from C.I. Reactive Red 24, 30 parts by weight of the liquid commercial form of C.I. Disperse Red 132, 100 parts by weight of urea and 10 parts by weight of sodium m-nitrobenzenesulfonate are dissolved in 150 parts by weight of water at 80.degree.
- This solution is stirred into 500 parts by weight of a stock thickener, the 230 parts by weight of an aqueous 4% alginate thickener, 80 parts by weight of an aqueous 10% strength starch ether thickener, 85 parts by weight of water, 25 parts by weight of an aqueous 10% solution of the condensation product of polyglycol 2000 with stearic acid and 80 Contains parts by weight of heavy gasoline.
- 100 parts by weight of the etching reserve are added, which was previously prepared by mixing 65 parts by weight of a 40% aqueous glyoxal solution, 310 parts by weight of sodium bisulfite solution 38 ° Bé, 125 parts by weight of water and 500 parts by weight of sodium hydrogen carbonate.
- a leached mixed fabric made of polyester cellulose 70:30 is padded with the dye liquor described in Example 1, carefully dried in a hot flue at 80-100 ° C. and overprinted in film printing with a printing paste consisting of 40 parts by weight of the liquid commercial form of C.I. Disperse Red 200, 30 parts by weight of the commercial form by C.I. Reactive Red 33, 80 parts by weight of urea, 274 parts by weight of water at 80 ° C, 10 parts by weight of sodium m-nitrobenzenesulfonate, 500 parts by weight of stock thickening according to Example 1, 30 parts by weight of sodium carbonate, 30 parts by weight of sodium bisulfite solution 38 ° Be, 6 parts by weight of 40% glyoxal solution.
- Example 1 After drying, the steam is steamed for 7 minutes to increase the reserve effect, and then the disperse dyes and the reactive dyes which are resistant to alkali sulfites are fixed in a high-temperature steamer at 185 ° C. for 6 minutes. Then, to fix the base coloring, padding is carried out with the fixing solution specified in Example 1, steaming at 110-115 ° C. for 10 seconds and completion as indicated in Example 1.
- a mercerized blend of 65:35 polyester-cotton is padded with a batch consisting of 100 parts by weight of a 20% liquid setting of the dye of the formula 40 parts by weight of the liquid commercial form of CI Reactive Blue 122, 808 parts by weight of water cold, 10 parts by weight of sodium m-nitrobenzenesulfonate, 20 parts by weight of a polyacrylic acid-based antimigrant, 2 parts by weight of monosodium phosphate, 20 parts by weight of sodium formate.
- a leached knitted fabric made of polyester COLVERA 70: 30 is padded with the following liquor: 50 parts by weight of the liquid commercial form from C.I. Disperse Red 278, 40 parts by weight of the commercial form of C.I. Reactive Red 63, 200 parts by weight of water at 80 ° C., 660 parts by weight of water cold, 10 parts by weight of sodium m-nitrobenzenesulfonate, 20 parts by weight of an antimigrant based on polyacrylic acid, 20 parts by weight of sodium formate.
- a block fabric of polyester and mercerized cotton in the ratio 65:35 is padded with a dye liquor composed of 150 parts by weight of a 20% liquid setting of the dye of the formula 40 parts by weight of the commercial form of CI Reactive Blue 122, 767 parts by weight of water, 3 parts by weight of sodium chlorate, 20 parts by weight of an antimigrant based on polyacrylic acid, 20 parts by weight of sodium formate. It is carefully dried in a hot flue at 80-100 ° C. and overprinted in rouleaux printing with a printing paste consisting of 60 parts by weight of the dye of the formula 60 parts by weight of the liquid commercial form of C: I. Disperse Blue 87, 255 parts by weight of water, 600 parts by weight of a 4% solution of sodium alginate, 25 parts by weight of sodium sulfite.
- a mercerized blended fabric of 65:35 polyester-cotton is padded with an approach consisting of: 50 parts by weight of the liquid commercial form of 5- (4-nitro-2-methylphen-1-yl) -azo-4-methyl-3-cyan 2,6-dihydroxypyridine, 40 parts by weight of the commercial form of CI Reactive Yellow 42, 867 parts by weight of water, 3 parts by weight of sodium chlorate, 20 parts by weight of an anti-migration agent based on polyacrylic acid, 20 parts by weight of sodium formate. It is carefully dried in a hot flue at 80-100 ° C and overprinted in roulette with a printing paste made from 60 parts by weight of the commercial form from C.I. Reactive Red 24, 40 parts by weight of the liquid commercial form of C.I. Disperse Red 132, 275 parts by weight of water, 600 parts by weight of a 4% solution of sodium alginate, 25 parts by weight of sodium sulfite.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Claims (6)
ou des colorants qui, sous l'une des formes tautomères possibles, répondent à la formule Il
et une pâte de réserve qui contient, comme agent de réserve:
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2856283 | 1978-12-27 | ||
DE19782856283 DE2856283A1 (de) | 1978-12-27 | 1978-12-27 | Verfahren zur herstellung von reserveeffekten auf polyester-zellulose-mischfaser-textilien |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0013378A1 EP0013378A1 (fr) | 1980-07-23 |
EP0013378B1 true EP0013378B1 (fr) | 1982-11-17 |
Family
ID=6058465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79105182A Expired EP0013378B1 (fr) | 1978-12-27 | 1979-12-14 | Procédé pour la réalisation d'effets de réserve sur des matières textiles fibreuses mixtes polyester-cellulose |
Country Status (4)
Country | Link |
---|---|
US (1) | US4265629A (fr) |
EP (1) | EP0013378B1 (fr) |
JP (1) | JPS5830439B2 (fr) |
DE (2) | DE2856283A1 (fr) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1114240B (it) * | 1979-05-18 | 1986-01-27 | Acna | Monoazocoloranti per la tintura e stampa di fibre chimiche |
DE2930541A1 (de) * | 1979-07-27 | 1981-02-12 | Hoechst Ag | Verfahren zur herstellung von reserveeffekten auf mischmaterialien aus polyester- und cellulosefasern |
DE3019726A1 (de) * | 1980-05-23 | 1981-12-03 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von reserveeffekten auf polyester-zellulose-mischfaser-textilien |
DE3019739A1 (de) * | 1980-05-23 | 1981-12-03 | Cassella Ag, 6000 Frankfurt | Verfahren zum bedrucken von synthetischem hydrophobem fasermaterial |
DE3021269A1 (de) * | 1980-06-06 | 1981-12-17 | Cassella Ag, 6000 Frankfurt | Verfahren zum faerben und bedrucken von synthetischen hydrophobem fasermaterial |
DE3036576A1 (de) * | 1980-09-27 | 1982-05-19 | Cassella Ag, 6000 Frankfurt | Wasserunloeslicher azofarbstoff, verfahren zu seiner herstellung und seine verwendung |
DE3041014A1 (de) * | 1980-10-31 | 1982-06-16 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von aetzreservedrucken von textilmaterialien |
DE3042144A1 (de) * | 1980-11-08 | 1982-07-22 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von aetzreservedrucken auf textilmaschinen |
DE3106036A1 (de) * | 1981-02-19 | 1982-09-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zum bedrucken von synthesefasern |
DE3113732A1 (de) * | 1981-04-04 | 1982-10-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zum bedrucken von synthesefasern |
DE3118193A1 (de) * | 1981-05-08 | 1982-11-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zum bedrucken von textilien |
DE3135433A1 (de) * | 1981-09-08 | 1983-03-24 | Cassella Ag, 6000 Frankfurt | Azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
US4441883A (en) * | 1981-09-11 | 1984-04-10 | Allied Corporation | Dyeing method for control of multicolored pattern nylon carpet |
DE3209329A1 (de) * | 1982-03-15 | 1983-09-15 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von ausbrenneffekten auf textilmaterialien |
DE3312488A1 (de) * | 1983-04-07 | 1984-10-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung alkalisch aetzbarer faerbungen und drucke |
DE3439532A1 (de) * | 1984-10-29 | 1986-04-30 | Hoechst Ag, 6230 Frankfurt | Verfahren zum erzeugen von weiss- und buntreserven auf polyamidfasermaterialien |
JPS6219105A (ja) * | 1985-07-18 | 1987-01-27 | ワイケイケイ株式会社 | 図柄、文字入り面フアスナ−の製造方法 |
US9718944B2 (en) | 2015-04-02 | 2017-08-01 | Cnh Industrial Canada, Ltd. | Method of coloring biocomposite materials |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2659719A (en) * | 1951-06-23 | 1953-11-17 | Eastman Kodak Co | 2-amino-5-nitrothiazole azo dye compounds |
DE1810306B2 (de) * | 1968-11-22 | 1973-02-01 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | Verfahren zur herstellung von reserveeffekten mit reaktivfarbstoffen unter reaktivfarbstoffen oder aus mischungen von reaktivfarbstoffen unterschiedlicher fixierbarkeit |
NL7403593A (fr) * | 1973-03-23 | 1974-09-25 | ||
ZA744836B (en) * | 1973-08-16 | 1975-08-27 | Hoechst Ag | Process for obtaining multicolor effects |
US4134723A (en) * | 1975-03-25 | 1979-01-16 | Imperial Chemical Industries Limited | Coloration process |
GB1543724A (en) * | 1975-08-13 | 1979-04-04 | Ici Ltd | Process for the production of discharge printing effects on synthetic textile materials |
GB1512321A (en) * | 1976-01-05 | 1978-06-01 | Ici Ltd | Colouration process for cellulose textile materials |
JPS5459483A (en) * | 1977-10-20 | 1979-05-14 | Meisei Chemical Works Ltd | Resist style method |
-
1978
- 1978-12-27 DE DE19782856283 patent/DE2856283A1/de not_active Withdrawn
-
1979
- 1979-12-14 EP EP79105182A patent/EP0013378B1/fr not_active Expired
- 1979-12-14 DE DE7979105182T patent/DE2964074D1/de not_active Expired
- 1979-12-19 US US06/105,204 patent/US4265629A/en not_active Expired - Lifetime
- 1979-12-26 JP JP54168436A patent/JPS5830439B2/ja not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE2856283A1 (de) | 1980-07-17 |
JPS5590689A (en) | 1980-07-09 |
US4265629A (en) | 1981-05-05 |
EP0013378A1 (fr) | 1980-07-23 |
DE2964074D1 (en) | 1982-12-23 |
JPS5830439B2 (ja) | 1983-06-29 |
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