MXPA98004413A - Interfacing of fiber cellular materials - Google Patents
Interfacing of fiber cellular materialsInfo
- Publication number
- MXPA98004413A MXPA98004413A MXPA/A/1998/004413A MX9804413A MXPA98004413A MX PA98004413 A MXPA98004413 A MX PA98004413A MX 9804413 A MX9804413 A MX 9804413A MX PA98004413 A MXPA98004413 A MX PA98004413A
- Authority
- MX
- Mexico
- Prior art keywords
- radical
- formula
- alkyl
- substituted
- process according
- Prior art date
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 title description 3
- 230000001413 cellular Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 61
- 239000002657 fibrous material Substances 0.000 claims abstract description 40
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
- 229920003043 Cellulose fiber Polymers 0.000 claims abstract description 9
- 239000004627 regenerated cellulose Substances 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- -1 heteroaromatic radical Chemical class 0.000 claims description 104
- 150000003254 radicals Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000000985 reactive dye Substances 0.000 claims description 8
- 238000005063 solubilization Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 7
- FBBHPHRBJLLIFM-UHFFFAOYSA-O pyridin-1-ium-1-carboxylic acid Chemical compound OC(=O)[N+]1=CC=CC=C1 FBBHPHRBJLLIFM-UHFFFAOYSA-O 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- JYZIHLWOWKMNNX-UHFFFAOYSA-N Benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N Benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001439 semicarbazido group Chemical group [H]N([H])C(=O)N([H])N([H])* 0.000 claims description 2
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 239000000047 product Substances 0.000 description 30
- 239000004744 fabric Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 229920000297 Rayon Polymers 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229920002456 HOTAIR Polymers 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atoms Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003490 calendering Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 description 2
- RTNUTCOTGVKVBR-UHFFFAOYSA-N 4-chlorotriazine Chemical group ClC1=CC=NN=N1 RTNUTCOTGVKVBR-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000004970 halomethyl group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2H-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2H-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- PRJRZFGWMPNWBH-UHFFFAOYSA-N 4,5-dichlorotriazine Chemical compound ClC1=CN=NN=C1Cl PRJRZFGWMPNWBH-UHFFFAOYSA-N 0.000 description 1
- DUIMWXDLDBNUFD-UHFFFAOYSA-N 4-pyrimidin-2-ylmorpholine Chemical compound C1COCCN1C1=NC=CC=N1 DUIMWXDLDBNUFD-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N Cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N Glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 229940015043 Glyoxal Drugs 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium Ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 102000014961 Protein Precursors Human genes 0.000 description 1
- 108010078762 Protein Precursors Proteins 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N Sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N iodine atom Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000011528 polyamide (building material) Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissues Anatomy 0.000 description 1
- BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Abstract
The present invention relates to the process for interlacing cellulosic fiber materials, especially cellulosic fiber materials that are from 20 to 100% by weight of natural or regenerated cellulose fibers, comprises applying to the cellulosic fiber materials, wherein the cellulosic fibers comprise natural or regenerated cellulose, at least one product of the general formula (1), wherein A is an aliphatic, aromatic or heteroaromatic radical, R is a radical reactive to the fiber, and n is 1, 2, 3 or 4, provided that the radical [R] n includes at least two groups reactive to fibers, and is useful for achieving permanent finishing effects, for example, in the area of easy care, dimensional stability and shrinkage resistance
Description
INTERLACING OF CELLULOSE FIBER MATERIALS
DESCRIPTION OF THE INVENTION
The present invention relates to a process for interlacing cellulosic fiber materials. The cellulosic fiber materials are interlaced to impart permanent finishing effects, for example, in the area of resistance to crease formation, easy care, dimensional stability, and shrinkage resistance. It is known to treat cellulosic fiber materials, such as textiles, with products that confer permanent finishing effects, for example shrinkage and crease resistance. The products used for this purpose include, for example, products obtained through the addition of formaldehyde to amide groups. These N-methylol compounds normally continue to comprise free formaldehyde remnants and can remove formaldehyde to a certain degree when subjected to a heat treatment, which can lead to an annoying odor and intolerance. This disadvantage of the N-methylol compounds can be reduced or avoided by using products with a low formaldehyde content or formaldehyde-free as interleavers for cellulose. The contemplated products have etherified N-methylol groups or do not contain any -N-CH2-O- group. An example of the last class of compounds is N, N'-dialkyl-4,5-dihydroxyimidazolidinones (N, N -
dialkylhydroxyethylene ureas), which can be obtained by reacting N. N'-dialkylureas with glyoxal. Similarly, the etherification products of the aforementioned compounds with polyhydric alcohols are known as crosslinkers for cellulosic materials. The disadvantage of the formaldehyde-free cellulose crosslinkers of the prior art is that the desired level of effect is not achieved in all cases. In addition, known products generally require temperatures of about 160 ° C or higher for an adequate crosslinking reaction with cellulose, which is undesirable. The formaldehyde-free interlayers, in addition, require relatively high or very high usage levels and additions and frequently lead to undesirable yellowing of the treated fiber materials. It is an object of the present invention to provide a method for interlacing cellulosic fiber materials, for example, in order to obtain a highly effective formaldehyde free finish of the fiber materials, which do not have the disadvantages described. The process makes it possible to carry out the reaction of the crosslinker with the cellulose (cure) at comparatively low temperatures, i.e., temperatures less than 1 50 ° C, and must lead to a higher level of resistance to crease or effect. It is easy to care for as far as possible using familiar freelanders of formaldehyde. This object is achieved through a procedure for
interlacing cellulosic fiber materials, especially cellulosic fiber materials, which are from 20 to 100% by weight of natural or regenerated cellulose, which comprises applying to the cellulosic fiber materials, wherein the cellulosic fibers comprise natural or regenerated cellulose, at least one product of the general formula (1):
> -E »J O).
wherein A is an aliphatic, aromatic or heteroaromatic radical, R is a radical reactive to the fiber, and n is 1, 2, 3 or 4, provided that the radical [R] n includes at least two reactive groups to the fiber. A is preferably an aromatic radical, which may be unsubstituted or substituted by C 1 -C 4 alkyl, for example, methyl or ethyl, C 1 -C alkoxy, for example methoxy or ethoxy, halogen, eg, fluorine, bromine or especially chlorine, carboxyl or preferably one or more water solubilization groups. Water solubilization groups include especially sulfo groups (-SO3H). An aromatic radical A is preferably a benzene radical, which can be substituted by one or two sulfo groups. The aromatic radical A preferably also can be free of water solubilization groups, if at least one of the radicals R contains a water solubilization group, for example, a sulfate group.
A aliphatic can be, for example, an alkyl radical of C? -C 18, preferably a C 2 -C 2 alkyl radical, which can be interrupted by one or more heterogeneous atoms, for example, oxygen, and which can be replaced by one or more water solubilization groups. Examples of suitable water solubilization groups are the sulfo groups and the hydroxyl groups. A heteroaromatic is, for example, a morpholino, pyrimidine or triazine radical, which can be substituted, for example, by halogen. The radicals reactive to the fibers are radicals capable of reacting with the hydroxyl groups of cellulose, the amino, carboxyl, hydroxyl or thiol groups in the case of wool and silk or with the amino or possibly carboxyl groups of synthetic polyamides with the formation of bonds covalent chemicals. The fiber-reactive groups are generally linked directly or through a bridge member to the colorless radical A. Examples of suitable reactive groups to fibers include those which contain at least one separable substituent on an aliphatic, aromatic or heterocyclic radical, or in which the radicals mentioned contain a radical suitable for reaction with the fiber material, for example, a triazine radical. Examples of the fiber-reactive groups include radicals reactive to fibers containing 4, 5 or 6 carbo- or heterocyclic rings substituted by a separable atom or group. Examples of heterocyclic radicals include radicals which contain
minus a separable substituent attached to a heterocyclic ring; and those containing at least one reactive substituent attached to a 5- or 6-membered heterocyclic ring, such as a monoazine, diazine, triazine, pyridine, pyrimidine, pyridazine, pyrazine, thiazine, oxazine or an asymmetric or symmetrical triazine ring. The radicals reactive to heterocyclic fibers mentioned further contain, via a direct bond or via a bridge member, more radicals reactive to fibers, such as the radicals described, for example. The fiber reactive groups further include those having at least one activated unsaturated group, especially an unsaturated aliphatic group, for example, a vinyl, halovinyl, styryl, acryloyl or methacryloyl group, or at least one polymerizable ring system. Examples of such groups are unsaturated groups substituted by halogen, such as the halomaleic acid and halopropionic acid radicals, a- or β-bromo- or -chloro-acryloyl groups, halogenated nylcetyl vi groups, halocrotonyl or halomethacryloyl groups. Also suitable are groups which, for example, through the hydrogen halide bond, are easily converted to halogen-containing unsaturated groups, for example, dichloro- or dibromo-propionyl. In the present it is understood that halogen means not only fluorine, chlorine, bromine and iodine atoms, but also pseudohalogen atoms, for example, cyano. The process of the present invention provides good results in the use of compounds containing an a-bromoacryloyl group. Among the compounds that contain a double
polymerizable link, preference is given to those containing at least one acryloyl, methacryloyl, a-bromoacyloyl, a-chloroacryloyl, vinyl or vinylsulfonyl radical; very preferably those containing at least one acryloyl, a-bromoacryloyl or vinylsulfonyl radical. Examples of more separable atoms or groups are ammonium, including hydrazinium, sulfate, thiosulfate, phosphate, acetoxy, propionoxy or carboxypyridinium. In formula (1), one of the four reactive radicals is not necessarily linked to radical A; rather, it is also possible that two or three active radicals can be linked together directly or via bridge members. The bridging member between the colorless radical A and the fiber-reactive radical, or between two or three fiber-reactive radicals, can be not only a direct bond, but also one of a very wide variety of radicals. The bridge member is, for example, an aliphatic, aromatic or heterocyclic radical; The bridge member can also be assembled from several of these radicals. The bridging member may contain at least one functional group, for example, carbonyl or amino, in which case the amino group may further be substituted by unsubstituted or substituted C 1 -C 4 alkyl with halogen, hydroxyl, cyano, alkoxy, Ci-C, C?-C4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfate An example of a suitable aliphatic radical is an alkylene radical having from 1 to 7 carbon atoms or a branched isomer of the
same. The carbon chain of the alkylene radical can be interrupted by a heterogeneous atom, for example an oxygen atom. An example of a suitable aromatic radical is a phenyl radical, which can be substituted by a C 1 -C 4 alkyl, for example, methyl or ethyl, C 1 -C 4 alkoxy, for example, methoxy or ethoxy, halogen, example, fluorine, bromine or especially chlorine, carboxyl or sulfo, and an example of a suitable heterocyclic radical is a piperazine radical. Examples of said bridge members are the following radicals:
-CO-N (R1) - (CH2) 2-3-; -C N (R,) - (CH2) 2-O- (CH2) 2-; -NÍR ^ -CO-ÍCH ^; -N (R,) -; -NÍ ^ MCHzk-O-íCHzk-; -O-ÍCH ^ -; -CHz-N (R?) -; (CH 2) 2 -CO-N 1 (CH 2).
-CO-
In the above-mentioned formulas, R is hydrogen or a C?-C4 alkyl, which can be substituted by halogen, hydroxyl, cyano, C?-C alco alkoxy, C?-C, carboxy, sulfamoyl, alkoxycarbonyl, sulfo or sulfate. The radicals A and [R] n in formula (1) are preferably linked together via a bridge member containing the amino group -N (R1) -, particularly preferably via the bridging member -N (R1) -, where R1 is as defined above.
The condition that the radical [R] n contains at least two fiber-reactive groups means that the compound of the formula (1) contains at least two of the fiber-reactive groups mentioned, for example, for n = 1, a dichloro- or difluoro-triazine radical, which has two separable halogen atoms, which are capable of reacting with the cellulose fiber or when n = 2, for example, a 4-monochloro- or 4-monofluoro-triazin radical -2-yl containing in the 6-position a fiber-reactive group, for example, a vinylsulfonyl group, which is attached directly or through a bridge member. The important reactive radicals R contain one or two fluoro- or chlorotriazine groups and optionally an aliphatic reactive group, especially of the vinylsulfonyl type, or contain two vinylsulfonyl reactive radicals. In important compounds of the formula (1), the colorless reactive radical A is an unsubstituted or sulfo-substituted benzene radical, and the radical reactive to fibers R comprises one or two fluoro- or chlorotriazine groups, which are attached via a member of bridge and containing an additional reactive radical, especially a vinylsulfonyl radical, via a bridge member. In more important compounds of the formula (1), the colorless radical A is an unsubstituted or sulfo-substituted benzene radical and the radical reactive to fibers R comprises two vinylsulfonyl radicals attached directly or through a bridge member. The reactive groups of interest are 1, 3, 5-triazine radicals of the formula:
wherein Tt is fluorine, chlorine or carboxypyridinium, and the substituent TO the triazine ring is fluorine, chlorine, -NH2, an alkylamino radical of C? -C6, N, N-di-alkylamino of C? -C6, cyclohexylamino, NN-dicyclohexylamino, benzylamino, phenethylamino, phenylamino, naphthylamino, N-C-C6-N-cyclohexylamino N-alkyl or Ci-C-N-phenylamino N-alkyl or is morpholino, piperidino, piperazino, hydrazino or semicarbazido, or is an amino group substituted by a furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole or benzoxazole radical. The alkyl, cycloalkyl, aralkyl and aryl radicals and also the heterocyclic radicals can also be substituted, for example, by C 1 -C 4 alkyl, for example methyl or ethyl, C 1 -C 4 alkoxy, for example, methoxy or ethoxy, halogen, for example, fluorine, bromine or especially chlorine, carboxyl or sulfo. The aforementioned condition that the radical [R] "contains at least two fiber-reactive groups means that Vi is fluorine or chlorine when n = 1 and R is a radical of the formula (2). V, in the formula (2), is in particular preferably fluorine, chlorine, phenylamino or N-C-C-N-phenylamino alkyl, wherein the phenyl rings can be substituted by halogen, such as fluorine, chlorine groups or bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C-C4 alkyl, C? -C4 alkoxy, acylamino, such as
acetylamino or benzoylamino, ureido, hydroxyl, carboxyl, sulfomethyl or especially sulfo. Reactive radicals to fibers of interest also include, for example, those of the formula:
wherein T2 and T3 are independently fluorine, chlorine or carboxypyridinium and B is a bridging member. The bridging member B in formula (2 ') can be, for example, a radical of the formula:
/ \ n -N- X- N- N N \ R / R, "/
wherein Ri 'and R' are independently hydrogen or unsubstituted or substituted C? -C alkyl by halogen, hydroxyl, cyano. C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl, carboxyl, sulphamoyl, sulfo or sulfate, and X is a C 2 -C 6 alkylene radical or Cs-C 9 cycloalkylene unsubstituted or substituted by hydroxyl, sulfo, sulfate, alkoxy C 1 -C 4, carboxyl or halogen, or is a phenylene, biphenylene or naphthylene radical unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, sulfo, halogen or carboxyl.
The most interesting reactive groups are those of the formula:
wherein T4 is fluorine, chlorine or carboxypyridinium and V2 is a radical of the formula:
wherein R 1 is hydrogen or C 1 -C 4 alkyl, which can be substituted by halogen, hydroxyl, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy, carboxyl, sulfamoyl, sulfo or sulfate; B-i is a direct link or a radical:
-PCH2 - 0 - ofcHfJ-
m is 1, 2, 3, 4, 5 or 6; and R 'is a radical of the formula:
- (alq) - CH2- S02- Z (4a)
(4b) -N- (alq) -CH2 - SO- Z
-N- (CH2) -0- (CH2) -SO- Z (4c)
- N- (alq -N-Halq'J-SO- Z (4d) R "
(CH2) -S02-Z -N. '(C? -SO ^ Z (4f)
/ \ N I N- (CH2) t SO2-Z (4g) \ /
wherein R "is hydrogen or C? -C6 alkyl, alk is an alkylene radical having from 1 to 7 carbon atoms, T is hydrogen, halogen, hydroxyl, sulfate, carboxyl, cyano, C? -C4 alkanoyloxy, C 1 -C 4 alkoxycarbonyl, carbamoyl or a radical -SO 2 -Z, V is hydrogen, substituted or unsubstituted C 1 -C 4 alkyl or a radical of the formula:
- (alq) -CH- SO2 ~ Z (4h) I T
wherein (alk) is as defined above, each alk 'is independently a polymethylene radical having from 2 to 6 carbon atoms, Z is β-sulfatoethyl, β-thiosulfatoethyl, β-phosphate ethyl, β-acyloxyethyl, β-haloethyl or vinyl, r and t each are independently 1, 2, 3, 4, 5 or 6 and s is 2, 3, 4, 5 or 6; and the benzene ring in the formula (4) may contain more substituents; or wherein V2 is a directly attached radical of formula (4a), (4b), (4c), (4d), (4e), (4f) or (4g), wherein R ', T, alk, V , alq ', Z, p, q, r, syt are each as defined above; or where V2 is a radical of the formula:
wherein Rt and Z are each as defined above and the benzene ring can also be substituted. Possible additional substituents for the benzene rings of the compounds of the formulas (4) and (4 ') are halogen, such as fluorine, chlorine or bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C -? - C alkyl , C? -C4 alkoxy, acylamino groups, such as acetylamino or benzoylamino, ureido, hydroxyl, carboxyl,
sulfomethyl and sulfo. The radical Bi contains from 1 to 6, preferably from 1 to 4 carbon atoms. Examples of Bi are methylene, ethylene, propylene, butylene, methyleneoxy, ethyleneoxy, propyleneoxy and butyleneoxy. When BT is - O - (CH2) m - it binds to the benzene ring through the oxygen atom. Bi is preferably a direct link. ß-HalQßtilo Z is preferably β-chloroethyl and β-acyloxyethyl Z is preferably β-acetoxyethyl. The alkylene radical alk is preferably methylene, ethylene, methylmethylene, propylene or butylene. Alcanoloxy T is especially acetyloxy, propionyloxy or butyryloxy, and alkoxycarbonyl T is especially methoxycarbonyl, ethoxycarbonyl or propyloxycarbonyl. Alkyl V can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl. Examples of R "are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl and, preferably, hydrogen. Polymethylene radicals alk are preferably ethylene, propylene or butylene. The index t is preferably 2, 3 or 4. The indices r and s are independently preferably 2. Preferred radicals V 2 are those of the formula (4), wherein B 1 is a direct bond and R is a radical of the formula 4a), or wherein V2 is a radical of the formula (4b), (4c) or (4f), which is directly linked to the triazine ring, or wherein V2 is a radical of the formula (4 '). Also of interest are the reactive groups of the formulas.
or
where Ri is as defined above and Xi and X2 are both chloro, or i is fluorine, provided that the radical [R] p in formula (1) contains at least two reactive groups to fibers. Preferred aliphatic reactive groups are those of the formulas: -SO2Z (5a),
-SO2-NH-Z (5b),
-NH-CO- (CH2) 3-SO2Z (5c),
-CO-NH-CH2CH2-SO2Z (5d) and
-NH-CO-Z! (5e), where Z is as defined above, Zi has the meanings of Z and can also be halomethyl or a, β-dihaloethyl. The halogen in halomethyl, ß-haloethyl or a, ß-dihaloethyl Zi is suitably chloro or bromo in particular. Particularly preferred aliphatic reactive groups are those of the formula (5a) and also those of the formulas (5c) and (5d). Here, Z is in particular β-sulfatoethyl or β-haloethyl. Preference is given to the compounds of the formula (1a):
where Q is the radical CY or is especially a nitrogen atom, Y is chlorine, V3 and W3 are each independently fluorine, chlorine, R2-X2'-, R3-X3'- or hydroxyl, R2 and R3 are each independently a colorless aliphatic radical and especially an alkyl radical of Ci-Cs with or without interruption by oxygen atoms, an aromatic radical, especially a phenyl radical unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or sulfo, or a heteroaromatic radical, X X2 'and X3' are each independently, -S-, -N (R ") -, NH-CO-phen-NH- or -NH-
CO-phen-CO-NH-, R4 is hydrogen, C1-C5 alkyl, Cs-C6 cycloalkyl or phenyl, fen is an unsubstituted or substituted phenylene group, and n is 1, 2, 3, or 4, provided that the radical [R] n in the formula (1a) contains at least two groups reactive to fibers. A in formula (1a) is how it was defined under formula (1). Preferred compounds of the formula (1a), wherein A is an aliphatic radical, are, for example, made up of the formula:
c? N? A. (6) Cl
wherein X is -NR5- or -S-, Ai is an aliphatic radical having 1 to 18 carbon atoms, which is free of sulfo groups, and R5 is hydrogen or C? -C4 alkyl or has the meanings of A1 independently of A ^ An aliphatic radical Ai with from 1 to 18 carbon atoms is, for example, an alkyl radical of C? -C? β, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl , sec-butyl, tert-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, heptadecyl or octadecyl, in which case the alkyl radical may be substituted, for example, by hydroxyl or alkoxy , and in which case the alkyl chain may be singly or in multitude interrupted, for example by oxygen, sulfur, amino, carboxyamido, aminocarbonyl, ureido, sulfonamido, aminosulfonyl, carboxyl and
carbonyloxy. Alkyl of C? -C Rs is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or isobutyl. A- \ is preferably a linear or branched d-C18 alkyl, especially C? -C? 8 alkyl substituted by -OR6, in which case the alkyl chain may be interrupted by one or more -Q- radicals, or is alkyl of linear or branched C1-C18, especially C?-C8 alkyl, in which case the alkyl chain is interrupted by one or more radicals -Qt-, where -Q1- is -O-, -S-, -NR7- , -CONR7-, NR7CO-, NR7-CO-NR7-, -SO NR7, -NR7-SO2-, -COO-, -OCO-, -NR7-COO- or -OCOO-, R6 is hydrogen or C-alkyl ? -C4, and R is hydrogen or C? -C4 alkyl. Alkyl of C? -C? 8 or C? -C8 alkyl Ai may also be optionally substituted by one or more substituents, for example, by carboxyl, carboxyamido or sulfonamido. X4 is preferably -NRS-, R5 is preferably methyl and in particular preferably hydrogen. Alkyl of C? -C R4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or isobutyl. Alkyl of C? -C4 R7 is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or isobutyl. R6 is preferably methyl and in particular preferably hydrogen. R7 is preferably hydrogen.
-Q? - is preferably -O-, -S- or -NH-. Of particular interest for the process of the present invention are the compounds of the formula (6), wherein -X-A represents the following radicals: -NHCH2CH2SCH2CH2OH, -NHCH2CH2CONHCH2CH2OH, -NHCH2CH2CH2CONHCH2CH2OH, -NHCH2CONHCH2CH2CH2OH, -NHCH2CONHCH2CH2CH2OH, -NHCH2CON (CH2CH2OH) 2, -NHCH2CH2NHCOCH2CH2CH2 OH, -NHCH2CH2CH2NHCOCH2CH2CH2OH, -NHCH2CH2CH2CONHCH2CH2CH2OH. Of particular importance for the process of the present invention are the compounds of the formulas:
Cl - NH-CH2-CH (OH) -CH2OH N ^ (6f),
Cl
Cl
CI. .N NH- (CH2) 2-NHSO2- (CH2) 3OH N ^ N (6m), and Cl
Cl N NH- (CH 2) 2-NHSO 2 - (CH 2) 4 OH N ^ N (6n). Cl
The compounds of the formulas (6f) and (6g) are the most important for the process of the present invention. The compounds of the formula (6) used in the process of the present invention are prepared in a conventional manner, for example, by reacting a trichlorotriazine of the formula:
c, N? CI N? N (7) Cl
with an equimolar amount of a compound of the formula:
HX4 - A, (8),
wherein X4 and Ai are each as defined under formula (6), and isolating the final product resulting from formula (6). The novel compounds of the formulas (6a) to (6n) are prepared in a similar manner by reacting a trichlorotriazine of the formula (7) with, for example, an amine of the formula: NH2-CH2CH2OCH2CH2OH (8a), NH2-CH2CH (OH) CH2OH (8b), NH2-CH2CH2CON (CH2CH2OH) 2 (8c), NH2-CH2CH2CH2CONHCH2CH2CH2OH (8d), NH2-CH2CH2NHCONHCH2CH2OH (8e), NH2-CH2CH2CH2SO2NHCH2CH2CH2OH (8f), NH2-CH2CH2NHSO2CH2CH2CH2OH (8g), or NH2- CH2CH2NHSO2CH2CH2CH2CH2OH (8h). The amines of the formulas (8a) to (8h) are either known or can be prepared by known methods. It is highly preferable that the compounds of the formula (1)
contain at least one reactive group of the formulas, (2), (2 '), (3), (4i) to (41), (5a) to (5e) and (6), wherein A, Ai, R ,, Ti, T2, T3, T4, Vi, V2, B, Xi, X, X, Z and Z, each one is subjected to the previous definitions and preferences. Of particular interest are those compounds of the formula (1), which contain a reactive group of the formulas (2), (2 '), (3), (4¡) to (41) and (5a) to (5e) ), where Ri, Ti, T2, T3, T4, Vi, V2, B, Xi, X, Z and Zi are each subject to the above definitions and preferences. A very particular preference is given to the compounds of the formula (1b):
wherein T5 is fluorine or especially chlorine and Ri is hydrogen, methyl or ethyl. Other preferred compounds in the process of the present invention conform to formula (1c):
NyY
where T5 and Ri are each as defined under the formula (1 b). In a particularly preferred embodiment of the process of the present invention, T5 is chloro and Ri is hydrogen in the compound of the formula (1c) used. More particularly, the two groups -NR- are arranged in or on the benzene nucleus. The process of the present invention is preferably carried out using the compounds of the formula:
^ -frl (1d)
wherein A2 is an unsubstituted or sulfo-substituted benzene radical, Rio is a radical of the formula (2), (2), (2 ') or (3), or wherein Rio is a radial -SO2-Z, where Z is as defined above, and n is 1, 2, 3 or 4, provided that the radical [R] n contains at least two reactive groups to fibers. When A is a heteroaromatic racial, additional compounds of interest for use in the process of the present invention conform to the formula.
wherein Ri and Z are each as defined under formula (4) or (4h), respectively, and Hai is halogen, preferably chloro. In the formula (1 e), Hai is especially chlorine, Ri is hydrogen and -SO2-Z is arranged meta or para to the amino group and is β-sulfatoethyl-sulfonyl. The process of the present invention is useful for obtaining permanent finishing effects, especially to improve the resistance to crease formation, easy care properties, dimensional stability and shrinkage resistance of fiber materials comprising not less than 20% by weight of natural or regenerated cellulose fibers. When the proportion of the cellulose fiber in less than 20% by weight, the effect of the finish is too small to achieve the advantages of the process. The fiber materials may include cellulose fibers in a mixture with other fibers, especially composed of polyester or polyamide, or may consist exclusively of cellulose fibers. Suitable cellulose fibers include not only natural fibers such as cotton, but also fibers composed of regenerated cellulose, for example, short viscose rayon fibers. Also suitable are modal fibers, for example, polynosic fibers, and cupro fibers. The "lyocell" fiber is not used in the process of the present invention. The fiber materials suitable for the treatment, especially after the treatment, via the process of the present invention are especially textile fabrics or stitches. Without
However, yarns whose resistance to stress can be increased through the application of the process of the present invention are also contemplated. An important and preferred field of use for the process of the present invention is the sponge tissue material. The high-quality sponge fabric shows a reduced fiber release, especially after application in laundry dryers. In the case of viscose fibers, the process of the present invention can prevent or at least reduce any change to the surface of the fiber, for example, due to the dyeing process. The method of the present invention has a number of advantages. The fiber materials to which the aforementioned products have been applied need only be dried at 80 to 130 ° C to obtain good easy-care effects. Temperatures of up to 150 ° C or more, as is necessary in the case of known formaldehyde-free crosslinkers, do not need to be used. In the process of the present invention, an alkaline interlacing liquor can also be applied through the wet-batch technique whereby, after application and a puncture procedure, for example, during the calendering of pad, the fiber material, for example in the form of a textile fabric, is stored at room temperature in a state where it is protected against drying and, after a certain drying period of, for example, 20 hours, is rinsed with water and dried. At least partial entanglement occurs during the
residence in the wet state. The process of the present invention can also be used to reduce the formation of dry specks, especially important in the case of fabrics covering furniture. After application of the interlayer in the wet entanglement process, the finished and dried fiber materials often exhibit better whiteness than in the case of using known methods involving heat setting. In addition, the damage resistance of the finished fiber materials is often appreciably better than in known methods. The process of the present invention, moreover, is advantageously combined with other processes, for example, with a reactive dye in an alkaline medium or other processes which are carried out in an alkaline medium. The combination of the process of the present invention with the dyeing and fixing of reactive dyes is of great advantage. The process of the present invention, moreover, frequently offers the advantage of less damage to the photoresist of direct and reactive metals than in the case of existing processes. In the process of the present invention, to the fiber materials, which are preferably textile fabrics or stitches, a product of the formula (1) has been applied. However, it is also possible to apply mixtures of a plurality of products that fall within the formula (1). In addition, other desired products can be applied to these fiber materials at the same time as a n or o
more products of the formula (1), for example, water repellents, oil repellents, or flame retardants. The application of said product mixtures can be effected through an individual treatment liquor, for example, through pad calendering, in which case the wet harvesting is generally not less than 50%, preferably from 60 to 80% , when these product mixtures are homogeneous mixtures. It is particularly advantageous for economic and ecological reasons to carry out the process of the present invention in such a way that a product of the formula (1) or a product mixture is applied to the fiber materials in the form of an aqueous solution or dispersion alkaline of this product or these products and the fiber materials are subsequently dried. They are preferably dried within the temperature range of 80 to 130 ° C, for example, by means of hot air; if necessary, however, other temperatures can also be used, for example, up to 140 ° C. In addition to the aforementioned addition of other products to the treatment liquor, a preferred embodiment of the process of the present invention also includes a reactive dye in a single operation. In this case, the treatment liquor comprises a reactive dye as well as one or more products of the formula (1) and optionally other products. This preferred embodiment of the process of the present invention is contemplated especially for alkaline treatment liquors, whose pH is preferably within the range of 7 to 13 at 20 ° C.
With respect to the stability of the solutions or dispersions, it is usually advantageous that the solutions or dispersions, preferably aqueous solutions or dispersions, which will be used in the process of the present invention have a pH in storage that is not below 7.0 and does not above 10.0, in some cases not above 9.0. The desired pH, for example within the range of 7 to 10, can be fixed or stabilized with Na 2 CO 3, K 2 CO 3, KHCO 3 or NaHCO 3, for example. The amount of alkali, for example of NaOH or KOH, required for the treatment of fiber materials (crosslinking reaction with cellulose) and / or for reactive staining should not be added just before use. Metal salts which are present in the alkaline aqueous medium and which are within the scope of formula (1) and are useful for the process of the present invention, can be monovalent and polyvalent metal cation salts. Particularly preferred monovalent metals or metal cations are sodium and potassium. The sodium or potassium salts of the water-soluble compounds of the formula (1) are particularly preferred. A preferred embodiment of the process of the present invention in this manner comprises using water-soluble products of the formula (1); these water soluble products in particular are sodium or potassium salts, which are used in aqueous finishing liquors. If only these sodium or potassium salts are used, they are preferably alkaline aqueous solutions. In
presence of other additives, which are insoluble in water but dispersible in water, the process of the present invention is preferably carried out using aqueous dispersions. The dispersants required to disperse said additional finishing agents in water are known to one skilled in the art. The aqueous dispersions, which comprise other products as well as also at least one compound of the formula (1) likewise preferably have an alkaline pH within the range of a pH of 7 to 13. The treatment of the fiber materials through of the process of the present invention can be carried out by commonly known methods. It is particularly advantageous to apply solutions or dispersants comprising at least one product of the formula (1) through pad calendering. This treatment is preferably carried out with an aqueous liquor comprising from 1 to 12% by weight, based on the total liquor, of one or more products of the formula (1). Typically, the fiber material comprises from about 1 to 6% by weight of the formula (1), based on the total weight of the finished fiber material, after the subsequent puncture. The subsequent drying can be carried out in a known apparatus, for example, through hot air, and preferably it is carried out within the temperature range of 80 to 130 ° C. During the drying process, a temperature gradient may be present. The drying is accompanied by a reaction (entanglement) of the product of the
formula (1) with cellulose. This reaction is achieved by the presence of an alkaline pH. As well as drying with hot air, it is also possible to treat saturated steam at temperatures between 98 and 105 ° C, for example, or to combine the hot air treatment with the saturated steam treatment. The entanglement with the OH groups of cellulose in this way is achieved by the presence of alkaline compounds. Even if the alkali compounds of the formula (1), for example metal salts of water-soluble compounds of the formula (1), are already used for the process of the present invention, it is advisable to add more alkaline compounds to the liquors of treatment. Especially sodium hydroxide and potassium hydroxide are highly useful for this purpose. Instead of the additional inclusion of these alkaline compounds in the treatment liquors, the process of the present invention can also be carried out in two stages. This is achieved, for example, through a first step of applying a first aqueous treatment liquor to the fiber materials, which comprises a product of the formula (1) and has a pH at which this liquor has a high stability , for example a pH of 7 to 10. This first aqueous treatment liquor may comprise other products, such as reactive dyes. The first treatment liquor can be applied through pad cayandraje. After calendering, the fiber material is dried. The second stage involves applying a second aqueous treatment liquor that
it comprises the amount of the alkaline compound necessary for the interlacing with cellulose. This alkaline compound is preferably sodium hydroxide or potassium hydroxide. The application of the second liquor is followed by drying, for example, from 80 to 130 ° C, during which the entanglement occurs. The second treatment liquor can be, for example, a solution of sodium hydroxide or aqueous potassium hydroxide of relatively high concentration, for example, between 30 and 60% by weight. At the temperatures employed, for example 80 to 1 30 ° C, the presence of alkaline compounds causes it to be present in entanglement (cure) with cellulose. For this reason, the treatment of the fiber materials with the treatment liquid is preferably carried out at a pH within the range of 7 to 1 3 (measured at 20 ° C). The fiber materials treated by the process of the present invention are remarkable for good permanent finishing effects, especially easy care, dimensional stability and shrinkage resistance. The compounds used in the process of the present invention can be applied to the fiber material and fixed on the fiber in various forms, especially in the form of aqueous solvents, preferably through the exhaust method. After fixing, the treated fiber materials are washed thoroughly with cold and hot water, optionally in
presence of an agent, which has a dispersing effect and promotes the diffusion of unfixed portions. The compounds of formula (1) which contain a solubilization group in water, for example a sulfo or sulfate group, are either present in the form of their free acid or preferably as their salts such as, for example, the salts of alkali metal, alkaline earth metal or ammonium metal, or as salts of an organic amine. Examples are the sodium, potassium, lithium or ammonium salts or the triethanolamine salt. The compounds of the formula (1) are either known or can be prepared similarly to known compounds. For example, the compounds of the formula (1) are, for example, reactive dye precursors, as described in WO 96/00399 or can be prepared similarly thereto. For the process of the present invention, the amounts in which the compounds of the formula (1) are used in the treatment baths, especially in dyebaths together with dyes, preferably reactive dyes, can vary within wide limits. In general, without advantageous amounts of 0.01 to 20% by weight, especially of 0. 1 to 15% by weight, by weight of the fiber. The treatment by the process of the present invention is preferably carried out through the exhaust method. The treatment generally occurs in an aqueous medium at a liquor ratio of, for example, 2: 1 to 60: 1,
especially from 5: 1 to 20: 1. The temperature for the treatment varies from, for example, 20 to 100 ° C, especially 40 to 90 ° C, preferably 55 to 80 ° C. In a particular preferred embodiment of the process of the present invention, the entanglement of the cellulosic fiber is carried out prior to dyeing or together with its dyeing, especially after manufacture of the fiber. In a particularly preferred embodiment of the process of the present invention, the entanglement of the cellulosic fiber materials is carried out together with their staining. The compounds of the formula (1) are notable for their high reactivity, good fixability and very good development capacity. Therefore, they can be applied through the escape staining method at low staining temperatures. The fixation yields are high and the non-fixed portions are easily washed, the difference between the degree of escape and the degree of fixation being notoriously small; that is, the loss of hydrolysis being very small. The following examples illustrate the invention. Temperatures are reported in degrees Celsius. The parts and percentages are by weight, unless otherwise stated. Parts by weight refer to parts by volume as the kilogram refers to liter.
EXAMPLE 1
g of viscose cloth was fixed at 50 ° C in a laboratory exhaust dye machine together with 100 ml of a liquor comprising 8 g of Glauber's salt and 1 g of a colorless compound of the formula (100) according to with in Table 1. After 10 minutes of stirring at 50 ° C, 2 g of anhydrous sodium carbonate was added in two portions. The viscose fabric was stirred for a further 20 minutes. The liquor temperature was raised to 60 ° C, and 0.2 ml of a 30% solution of sodium hydroxide was added. After 20 minutes, the bath was pulled and the viscose fabric was rinsed with cold water, boiled and rinsed with cold water once again and dried. The result obtained is a viscose fabric having a higher dimensional stability and superior wet abrasion resistance.
EXAMPLE 2
g of viscose cloth was fixed at 50 ° C in a laboratory exhaust dye machine together with 100 ml of a liquor comprising 8 g of Glauber's salt and 1 g of a colorless compound of the formula (100) according to with Table 1 and 0.1 g of the dye of the formula (200) according to Table 2. After 20 minutes of stirring at 50 ° C, 2 g of anhydrous sodium carbonate were added in two portions. The viscose fabric is
He stirred for 10 more minutes. The liquor temperature was raised to 60 ° C, and 0.2 ml of a 30% solution of sodium hydroxide was added. After 20 minutes, the bath was pulled and the viscose fabric was rinsed with cold water, boiled and rinsed with cold water once again and dried. The result obtained is a marine viscose fabric that has greater dimensional stability and superior wet abrasion resistance. The replacement in Example 1 of the compound of the formula (100) with other compounds indicated in Table 1 also provides a viscose fabric with the reported advantageous properties. The replacement in Example 2 of the dye of the formula (200) with the dye of the formula (201) provides a red viscose fabric with the reported advantageous properties. The replacement in Example 2 of the compound of formula (100) with other compounds specified in Table 1 also offers a viscose fabric having the reported advantageous properties.
TABLE 1
Colorless compounds according to formula (1) in the free acid form:
TABLE 2
Colorants in the form of the free acid of the formula:
EXAMPLE 3
18.5 g of cyanuric chloride were introduced into a mixture consisting of 100 g of finely ground ice and 50 ml of water comprising 0.6 g of a commercially available surfactant and wetted for 15 minutes. Then, with good agitation, 6.1 g of ethanolamine was added dropwise in such a way that the pH of the mixture was kept at about 8.
At the end of the addition of the ethanolamine, approximately 8 g of a 50% aqueous solution of NaOH were added dropwise in such a way that the pH is maintained at 8. The resulting fine suspension is filtered and dried, providing 15.5 g of water. a white powdery compound of the formula:
EXAMPLE 4
Example 3 was repeated with 6.1 g of ethanolamine replaced by an equivalent amount of one of the amines specified in Table 3. The compounds listed in Table 3 were obtained.
TABLE 3
EXAMPLE 5
g of viscose cloth was fixed at 50 ° C in a laboratory exhaust dye machine together with 100 ml of a liquor comprising 8 g of Glauber's salt and 1 g of the first compound in Table 3 and 0.1 g of the dye of the formula (200) according to in Table 2. After 20 minutes of stirring at 50 ° C, 2 g of anhydrous sodium carbonate was added in two portions. The viscose fabric was stirred for a further 10 minutes. The temperature of
liquor was raised to 60 ° C, and 0.2 ml of a 30% solution of sodium hydroxide was added. After 20 minutes, the bath was pulled and the viscose fabric was rinsed with cold water, boiled and rinsed with cold water once again and dried. The result obtained is a marine viscose fabric that has a higher dimensional stability and superior wet abrasion resistance.
EXAMPLE 6
An aqueous suspension comprising, per liter, 85 g of the colorless compound of the formula (100), was mixed in equal parts by volume of an aqueous alkaline solution comprising, per liter, 140 ml of water glass of 38 ° B and 20 g. of sodium hydroxide and the mixture was then placed in pads on a cotton cloth with a wet pickup of 70 to 75%. The fabric thus treated was then treated immediately at 10 ° C with hot air for 5 minutes, the alkali was removed by rinsing with cold and hot water, and the cloth was then dried once more. The result obtained is a fabric having significantly improved crease forming properties.
EXAMPLE 7
An aqueous suspension comprising, per liter, 85 g of the
The colorless compound of the formula (100) was mixed in equal parts by volume with an aqueous alkaline solution comprising, per liter, 60 g of calcined sodium carbonate and the mixture was then placed in pads immediately on a cotton cloth with an wet from 70 to 75%. The cloth thus treated was then immediately dried at 130 ° C with hot air for 2 minutes, treated at 102 ° C with saturated steam for 8 minutes, the alkali was removed by rinsing with cold and hot water, and the cloth was dried once plus. The result obtained is a fabric with significantly improved crease forming properties.
Claims (15)
1. - A process for interlacing cellulosic fiber materials, which comprises applying to the cellulosic fiber materials wherein the cellulosic fibers comprise natural or regenerated cellulose, by at least one product of the general formula (1): wherein A is an aliphatic, aromatic or heteroaromatic radical, R is a radical reactive to the fiber, and n is 1, 2, 3 or 4, provided that the radical [R] p includes at least two fiber-reactive groups.
2 - A method according to claim 1, wherein the fiber materials used are from 20 to 100% by weight cellulosic.
3. A process according to any of claims 1 or 2, wherein R in the formula (1) is a radical of the formula: wherein Ti is fluorine, chlorine or carboxypyridinium, and Vi is fluorine, chlorine, -NH2, an alkylamino radical of C? -C6, N, N-di-alkylamino of C? -C6, cyclohexylamino, N, N-dicyclo- hexylamino, benzylamino, phenethylamino, phenylamino, naphthylamino, N-C 1 -C 6 -N-cyclohexylamino or N-C 6 -C 6 -N-phenylamino alkyl or is morpholino, piperidino, piperazino, hydrazino or semicarbazido, or is a amino group substituted by a furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole or benzoxazole radical.
4. A process according to any of claims 1 or 2, wherein R in the formula (1) is a radical of the formula: wherein T2 and T3 are independently fluorine, chlorine or carboxypyridinium and B is a bridging member of the formula: -N- X- - N N- I I R, 'a " wherein R ^ and Ri "are independently hydrogen or unsubstituted or substituted C C -C 4 alkyl by halogen, hydroxyl, cyano, C 1 -C 4 alkoxy, Ci-C alkoxycarboxyl, carboxyl, sulfamoyl, sulfo or sulfate, and X is a C2-C6 alkylene radical or C5-C9 cycloalkylene unsubstituted or substituted by hydroxyl, sulfo, sulfate, C? -C4 alkoxy, carboxyl or halogen, or is a phenylene, biphenylene or naphthylene radical unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, sulfo, halogen or carboxyl.
5. A process according to claim 1, wherein the compound used has the formula (1a): wherein A is as defined in claim 1, Q is the radical CY or is a nitrogen atom, Y is chlorine, V3 and W3 are each independently fluorine, chlorine, R2-X2'-, R3-X3'- or hydroxyl, R 2 and R 3 are each independently a colorless aliphatic radical and especially a C 1 -C 8 alkyl radical with or without interruption by oxygen atoms, an aromatic radical, especially a phenyl radical unsubstituted or substituted by C alkyl? -C, C1-C4 alkoxy, halogen or sulfo, or a heteroaromatic radical, X1 ', X2' and X3 'are each independently, -S-, -N (R4) -, NH-CO-phen-NH- or -NH-CO-phen-CO-NH-, R4 is hydrogen, C1-C5 alkyl, C5-C6 cycloalkyl or phenyl, fen is an unsubstituted or substituted phenylene group, and n is 1, 2, 3, or 4, provided that the compound of the formula (1a) contains at least two groups reactive to fibers.
6. A process according to claim 5, wherein compounds of the formula are used: cl? N? X A wherein X is -N RS- or -S-, Ai is an aliphatic radical having 1 to 18 carbon atoms, which is free of sulfo groups, and R5 is hydrogen or C? -C alkyl or has the meanings of Ai independently of Ai.
7. A process according to any of claims 1 or 2, wherein the compound of the formula (1) is a compound of the formula: wherein T5 is fluorine or especially chlorine and R1 is hydrogen, methyl or ethyl.
8. - A process according to claim 1, wherein compounds of the formula (1c) are used: wherein T5 and Ri are each as defined in claim 7.
9. A process according to any of claims 1 to 5, wherein A in formula (1) is an aromatic radical, especially a radical benzene.
10. A process according to claim 9, wherein A in the formula (1) is substituted by at least one solubilization group in water, especially at least one sulfo group. 1.
A process according to any of claims 1 and 2, wherein R in the formula (1) is a radical of the formula: wherein T4 is fluorine, chlorine or carboxypyridinium and V2 is a radical of the formula: wherein Ri is hydrogen or C? -C4 alkyl, which can be substituted by halogen, hydroxyl, cyano, C? -C4 alkoxy, C? -C alkoxycarboxy, sulfamoyl, sulfo or sulfate; Bi is a direct link or a radical: m is 1, 2, 3, 4, 5 or 6; and R 'is a radical of the formula: -N- (alq) - CH- SO¿- (4a) V (4b) -N- (alq) -CH2-SO- Z R " N- (CH2) -0- (CH2) -S02-Z (4c) -N - (alq1) - NH -alk -SO ^ - Z (4d) R " N N- (CH2) -SO2-Z (4g) wherein R "is hydrogen or C? -C6 alkyl, alk is an alkylene radical having from 1 to 7 carbon atoms, T is hydrogen, halogen, hydroxyl, sulfate, carboxyl, cyano, C? -C4 alkanoyloxy, C? -C alkoxycarbonyl, carbamoyl or a radical -SO2-Z, V is hydrogen, substituted or unsubstituted C? -C4 alkyl or a radical of the formula: - (alq) -CH2- SO, -Z (4h) wherein (alk) is as defined above, each alk 'is independently a polymethylene radical having from 2 to 6 carbon atoms, Z is β-sulfatoethyl, β-thiosulfatoethyl, β-phosphate ethyl, β-acyloxyethyl, β-haloethyl or vinyl, r and t each are independently 1, 2, 3, 4, 5 or 6 and s is 2, 3, 4, 5 or 6; and the benzene ring in the formula (4) may contain more substituents; or wherein V2 is a directly attached radical of the formula (4a), (4b), (4c), (4d), (4e), (4f) or (4g), wherein R ', T, alk, V , alq ', Z, p, q, r, syt are each as defined above; or where V2 is a radical of the formula: wherein R (and Z are each as defined above and the benzene ring can be further substituted.)
12. A process according to claim 1, wherein compounds of the formula are used: ^ -M. (1 C) wherein Ai is an unsubstituted or sulfo-substituted benzene radical, Rio is a radical of formula (2), (2 ') or (3), or wherein Rio is the radical -SO2-Z, wherein Z is as defined above, and n is 1, 2, 3 or 4.
13. A process according to any of claims 1 to 12, wherein the compound of the formula (1) is applied to the fiber together with reactive dyes. .
14 - The treated cellulose fiber material according to claim 1.
15. An aqueous solution or dispersion comprising a compound of the formula (1) as set forth in claim 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1337/97 | 1997-06-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA98004413A true MXPA98004413A (en) | 1999-04-06 |
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