EP0638686A1 - Verfahren und Verwendung reaktiver Dispersionsfarbstoffe zum Färben oder Bedrucken aminierter, textiler Baumwoll- und Baumwoll-/Polyester-Mischgewebe - Google Patents
Verfahren und Verwendung reaktiver Dispersionsfarbstoffe zum Färben oder Bedrucken aminierter, textiler Baumwoll- und Baumwoll-/Polyester-Mischgewebe Download PDFInfo
- Publication number
- EP0638686A1 EP0638686A1 EP94112297A EP94112297A EP0638686A1 EP 0638686 A1 EP0638686 A1 EP 0638686A1 EP 94112297 A EP94112297 A EP 94112297A EP 94112297 A EP94112297 A EP 94112297A EP 0638686 A1 EP0638686 A1 EP 0638686A1
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- EP
- European Patent Office
- Prior art keywords
- group
- groups
- amino
- methyl
- hydroxyl
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000004043 dyeing Methods 0.000 title claims abstract description 40
- 239000000835 fiber Substances 0.000 title claims abstract description 21
- 229920000728 polyester Polymers 0.000 title claims abstract description 16
- 229920000742 Cotton Polymers 0.000 title description 11
- 239000004753 textile Substances 0.000 title description 6
- 238000007639 printing Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 239000000986 disperse dye Substances 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000003792 electrolyte Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- -1 amino, sulfo, hydroxy Chemical group 0.000 claims description 117
- 239000002657 fibrous material Substances 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000003277 amino group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 10
- 125000004185 ester group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- SEMURSKJWYPYKW-UHFFFAOYSA-N 4-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCC1COC(=O)N1 SEMURSKJWYPYKW-UHFFFAOYSA-N 0.000 claims description 3
- HUHZAMBLEKHDBP-UHFFFAOYSA-N 5-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCC1CNC(=O)O1 HUHZAMBLEKHDBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 229920003043 Cellulose fiber Polymers 0.000 abstract description 3
- 229920002678 cellulose Polymers 0.000 abstract description 2
- 239000001913 cellulose Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000004744 fabric Substances 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009981 jet dyeing Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- BWVZLXTZQHILRC-UHFFFAOYSA-N 4-chloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(Cl)=N1 BWVZLXTZQHILRC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 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
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001439 semicarbazido group Chemical group [H]N([H])C(=O)N([H])N([H])* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000009970 yarn dyeing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
- D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
Definitions
- a method was therefore desirable for the future, textile fibers, preferably those that contain the base body of the ⁇ , ⁇ -glucose and the polyester at the same time, using only one class of dyes, i.e. without intermediate rinsing processes or changes in the pH value of the dyeing liquors.
- the present invention therefore relates to a process for dyeing materials made from hydroxyl-containing fibers, such as cellulose fibers, or from mixed fiber materials made from hydroxyl-containing fibers and polyester fibers, which is characterized in that the hydroxyl-containing fiber material is a hydroxyl-containing fiber material modified with an amino group-containing compound and a fiber-reactive dye Disperse dye is used and the coloring in an aqueous, low-electrolyte or completely electrolyte-free medium and in the absence of an alkaline or alkali-donating agent, such as at a pH between 5 and 7, preferably between 5.5 and 6.5, and at Temperature between 100 and 210 ° C, preferably between 110 and 190 ° C, is carried out.
- hydroxyl-containing fibers such as cellulose fibers
- Dyeing processes are also understood to mean the printing processes customary in the art for printing on textile materials and dyeing using ink jet printers.
- Modified fiber materials containing hydroxy groups which can be used in the process according to the invention are, for example, those described in Canadian Patent Nos. 1,267,490 and 2,084,585, in European Patent Application Publication No. 0 286 597 and in Japanese Patent Application Publication Hei -5-5279 are described, furthermore such fiber materials that with those in the German Laid-Open Patent Application No. 2,930,738 have been pretreated and modified as aftertreatment agents, and furthermore in particular hydroxy group-containing fiber materials which have been modified in accordance with the information in European Patent Application Publication No. 0 546 476 or with the compounds of the general formula (1) described below.
- the information in the patent documents mentioned about the modified fiber materials and their production should be part of the disclosure of the present application.
- ester group ER is a sulfato group of the formula -OSO3M, where M is hydrogen or an alkali metal, for example sodium, potassium or lithium, and the amino group-containing compound N is particularly preferred - ( ⁇ -sulfatoethyl) piperazine.
- the compounds of the formula (1) can be prepared according to known procedures, as are described in numerous publications (see Houben-Weyl, Methods of Organic Chemistry, 4th edition, Volume E4, pages 82-88 and 192ff.) , for example by reacting an alkanediol which has a latent nitrogen-containing functional group in the side chain with phosgene in aqueous solution at a pH between 7 and 9 to produce the heterocycloaliphatic carbonates or, for example, by Reaction of aminoalkanols with phosgene in aqueous solution to the heterocycloaliphatic carbamic acid compounds (2-oxo-1,3-oxazolidines).
- the modification of the fiber materials containing hydroxy groups with the compounds of the general formula (1) can be carried out analogously to the information in European patent application publication No. 0 546 476, for example in such a way that the compound of the formula (1) is dissolved in an aqueous, alkaline solution at a temperature between 60 and 200 ° C, preferably between 90 and 190 ° C, can act on the original hydroxy group-containing fiber material.
- the compound of the general formula (1) is present in the alkaline aqueous solution in a concentration between 0.1 and 20% by weight, preferably between 5 and 10% by weight.
- Sodium hydroxide, sodium carbonate and potassium carbonate for example, can be selected as an alkaline agent, which is generally in a concentration between 0.1 and 20% by weight, preferably between 5 and 10 wt .-%, is included and gives the solution a pH between 10 and 14.
- the fiber material to be dyed according to the invention in the method according to the invention can be used in all processing states, such as yarn, flake, sliver and piece goods, such as woven and knitted fabrics.
- Dyeing proofs that can be used according to the invention are, for example, the various pull-out dyeing processes, such as dyeing on the jigger or on the reel runner or dyeing from a long or short liquor, dyeing in jet dyeing machines or using a block-hot steam fixing method for pure modified ones Fiber materials containing hydroxy groups as well as the high-temperature exhaust process and thermal insulation process for polyester fibers or mixed fibers made of polyester fibers and modified fibers containing hydroxy groups.
- a dyeing temperature in the range from 100 to 140 ° C., preferably 110 to 130 ° C., is sufficient for dyeing the modified fiber materials containing hydroxyl groups, such as the modified cotton fiber.
- a dyeing temperature of above 120 ° C., preferably above 130 ° C., in particular from 170 to 210 ° C. is appropriate for dyeing the polyester fiber components when using an exhaust process.
- Mixed fiber materials which can be used according to the invention are usually dyed above 180 ° C. when used by the thermal insulation process.
- Dyeing proofs which can be used according to the invention are also the customary printing processes for the production of prints on textile fiber materials, including ink-jet printing and transfer printing.
- the suitable temperature range for fixing the fiber-reactive disperse dye must be selected depending on the type of fiber used.
- the fiber-reactive disperse dye which was applied to a mixed fabric of modified cellulose fiber and polyester fiber that can be used according to the invention, for example by the ink-jet technique, can be fixed on the fiber material after a short predrying phase using a thermal insulation method.
- the dyeings of the modified hydroxyl-containing fiber materials obtainable in the manner according to the invention do not require any further aftertreatment after removal from the dyebath or after the dye has been fixed on the substrate, in particular no complicated aftertreatment process, including washing. As a rule, it is sufficient to rinse the colored substrate one or more times warm or hot and optionally cold water, which can optionally contain a nonionic wetting agent. A final boiling treatment of the dyed substrate with a washing solution to improve the fastness properties is not necessary.
- Fiber-reactive disperse dyes which can be used according to the invention in the dyeing process according to the invention are dyes which, apart from the fiber-reactive group, contain no water-solubilizing group, the fiber-reactive group itself not being or possessing a water-solubilizing group or having only such a water-solubilizing group which is split off under the dyeing conditions, such as, for example, the ⁇ -sulfatoethylsulfonyl group, which is capable of transitioning into the vinylsulfonyl group at temperatures above 100.degree.
- Fiber-reactive groups are generally understood to mean those parts of the molecule which contain hydroxyl groups of the fiber materials, such as, for example, cellulose or the amino and thiol groups of fiber materials, such as, for example, wool and silk, or of synthetic polymers, such as polyamides, or the amino groups of those with amino compounds modified hydroxy group-containing fiber materials and can form a covalent chemical bond with these groups.
- Particularly interesting fiber-reactive radicals are fluorine and chloro-1,3,5-triazine radicals of the formula (4) in which Hal is chlorine or fluorine and Q is an amino, alkylamino, N, N-dialkylamino, cycloalkylamino, N, N-dicycloalkylamino, aralkylamino, arylamino, N-alkyl-N-cyclohexylamino, N-alkyl -N-arylamino group or an amino group which contains a heterocyclic radical which may have a further fused-on carbocyclic ring, or amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring which optionally contains further heteroatoms, and hydrazino and semicarbazido groups, where the alkyl radicals mentioned can be straight-chain or branched and low molecular weight and higher molecular weight, preferably those having 1 to 6 carbon atoms.
- Suitable cycloalkyl, aralkyl and aryl radicals are, in particular, cyclohexyl, benzyl, phenethyl, phenyl and naphthyl radicals; Heterocyclic residues are especially furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole residues.
- Suitable amino groups, in which the amino nitrogen atom is a member of an N-heterocyclic ring are preferably residues of six-membered N-heterocyclic compounds which may contain nitrogen, oxygen or sulfur as further heteroatoms.
- alkyl, cycloalkyl, aralkyl and aryl radicals, the heterocyclic radicals and the N-heterocyclic rings can additionally be substituted, for example by halogen, such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C1 -C4 alkyl, C1-C4 alkoxy, acylamino groups such as acetylamino or benzoylamino, or ureido.
- halogen such as fluorine, chlorine and bromine
- sulfamoyl carbamoyl
- C1 -C4 alkyl C1-C4 alkoxy
- acylamino groups such as acetylamino or benzoylamino, or ureido.
- amino groups are: -NH2, methylamino, ethylamino, propylamino, isopropylamino, butylamino, hexylamino, ⁇ -methoxyethylamino, ⁇ -methoxypropylamino, ⁇ -ethoxyethylamino, N, N-dimethylamino, N, N-diethylamino, ⁇ -chloroethylamino , ⁇ -cyanoethylamino, ⁇ -cyanopropylamino, benzylamino, phenethylamino, cyclohexylamino, phenylamino, toluidino, xylidino, chloranilino, anisidino, phenetidino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, morpholino, piperidino Semicarbazi
- Q can be an amino radical of the general formula -NR10R11, in which R10 is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, and R11 is phenyl which is formed by a fiber-reactive radical of the vinylsulfone series directly or via a methylamino , Ethylamino-, methylene, ethylene or propylene group is substituted and which can still be substituted by 1 or 2 substituents from the group methoxy, ethoxy, methyl, ethyl and chlorine, or R11 is alkyl of 2 to 4 carbon atoms, such as Ethyl or n-propyl, which is substituted by a fiber-reactive group of the vinyl sulfone series, or alkylene phenyl with an alkylene radical of 1 to 4 carbon atoms, the phenyl of which is substituted by a fiber-reactive radical of the vinyl sulfone series, or in which R10
- Such fiber-reactive disperse dyes are described, for example, in US Pat. Nos. 3,974,160, 3,959,338, 4,025,646, 4,473,499, 4,500,455, 4,515,716 and 4,837,390, in Swiss Patent No. 564,515 and in Japanese Patent Application Publication Hei-3-247 665.
- the information in these patent official documents relating to these fiber-reactive disperse dyes is intended to be part of the disclosure of the present application.
- aqueous pretreatment liquor which contains 750 parts of N- (2-sulfatoethyl) piperazine and 450 parts of sodium hydroxide.
- the fleet is heated to 130 ° C with continuous goods guidance in the apparatus.
- the liquor is left at this temperature for 30 minutes, then cooled to 80 ° C. and the cotton material is washed first with cold water, then with warm water at 60 ° C., a commercially available wetting agent being used, and again thoroughly with cold water to.
- the pretreated but still wet product is mixed with 20,000 parts of water in the same machine.
- 10 parts of a polyester / cotton blend fabric are in a liquor ratio of 1:10 with a liquor containing 50 parts of N- (2-sulfatoethyl) piperazine and 20 parts of sodium hydroxide per 1000 parts of water for 15 min pretreated at 95 ° C.
- This process is followed by a washing process, first with cold, then with 60 ° C hot Water, which may contain a commercially available nonionic surfactant. After washing again with cold water, the fabric pretreated in this way is fed directly into a single-bath dyeing process.
- 30 parts of bleached cotton yarn are exposed on a package in a yarn dyeing apparatus in 450 parts of a pretreatment liquor consisting of 50 parts of N- (2-sulfatoethyl) piperazine, 30 parts of sodium hydroxide and 1000 parts of water, by heating the liquor heated to 130 ° C alternately pumps from the inside to the outside and from the outside to the inside through the coil. After 30 minutes, the liquor is cooled, the dyed material is rinsed thoroughly with cold water and then washed at 60 ° C. for about 5 minutes, a nonionic surfactant being able to be used. After a new rinse cycle, the yarn is directly subjected to a dyeing process.
- a pretreatment liquor consisting of 50 parts of N- (2-sulfatoethyl) piperazine, 30 parts of sodium hydroxide and 1000 parts of water
- the dyeing machine is filled with 450 parts of an aqueous liquor, which contains 0.6 part of the fiber-reactive disperse dye known from Example 102 of German Offenlegungsschrift 2 008 811, and the liquor is heated to 120 ° C., the liquor being led applied in the pretreatment process. After 30 minutes at 120 ° C., the cooled liquor is removed and the colored material is rinsed and washed in the usual way. You get a yellow colored yarn with good fastness properties.
- 10 parts of a polyester / cotton blend are with an aqueous liquor containing 50 parts of N- (2-sulfatoethyl) piperazine and 30 parts of sodium hydroxide per 1000 parts of water, with a liquor absorption of 80%, based on the weight of the fabric , padded and then subjected to heat setting at 180 ° C for 45 seconds.
- the material is then rinsed cold and hot washed at 60 ° C for 10 minutes, using a non-ionic wetting agent.
- the material After rinsing again with cold water, the material is transferred to an HT dyeing machine and treated at a liquor ratio of 1:20 with an aqueous liquor which contains 0.15 part of the fiber-reactive disperse dye known from Example 109 of German Offenlegungsschrift 2 008 811 .
- the fiber mixture is dyed at 130 ° C. for 30 minutes.
- the dyeing obtained is aftertreated by rinsing and soaping in the customary manner. A blue color is obtained on both fiber fractions with the very good fastness properties customary according to the prior art.
- the procedure is, for example, analogous to that of Examples 1 to 4 above, but using one of the fiber-reactive dyes specified in the table examples below.
- a strongly colored dyeing is obtained in the shade specified for the respective dye for both fiber components in a uniform shade and good fastness properties.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
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- Coloring (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4327301 | 1993-08-13 | ||
DE4327301A DE4327301A1 (de) | 1993-08-13 | 1993-08-13 | Verfahren und Verwendung reaktiver Dispersionsfarbstoffe zum Färben oder Bedrucken aminierter, textiler Baumwoll- und Baumwoll-/Polyester-Mischgewebe |
Publications (1)
Publication Number | Publication Date |
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EP0638686A1 true EP0638686A1 (de) | 1995-02-15 |
Family
ID=6495169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94112297A Withdrawn EP0638686A1 (de) | 1993-08-13 | 1994-08-05 | Verfahren und Verwendung reaktiver Dispersionsfarbstoffe zum Färben oder Bedrucken aminierter, textiler Baumwoll- und Baumwoll-/Polyester-Mischgewebe |
Country Status (6)
Country | Link |
---|---|
US (1) | US5498267A (cs) |
EP (1) | EP0638686A1 (cs) |
JP (1) | JPH07145574A (cs) |
BR (1) | BR9403236A (cs) |
DE (1) | DE4327301A1 (cs) |
TW (1) | TW290604B (cs) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0690166A3 (de) * | 1994-06-29 | 1996-05-01 | Hoechst Ag | Verfahren zum Färben aminierter Cellulose-/Polyester-Mischgewebe mit faserreaktiven Dispersionsfarbstoffen |
WO2004081279A1 (de) * | 2003-03-13 | 2004-09-23 | Lenzing Aktiengesellschaft | Verfahren zum färben einer mischung aus zwei oder mehr unterschiedlichen fasertypen |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6623532B2 (en) * | 2000-09-06 | 2003-09-23 | Seiren Co., Ltd. | Ink-jet printing method and printed goods |
JP2012082546A (ja) * | 2010-10-08 | 2012-04-26 | Mimaki Engineering Co Ltd | 分散染料(昇華型)によるインクジェット捺染に供される布帛の前処理剤及びその利用 |
ECSP11011300A (es) * | 2011-09-02 | 2012-07-31 | King Ernesto Quintana | Compuesto químico especial único formulado para cambiar, mejorar y optimizar los procesos comunmente utilizados en la industria textil |
US9844949B2 (en) | 2013-02-12 | 2017-12-19 | Sensient Colors Llc | Ink compositions |
CN110359299B (zh) * | 2019-08-23 | 2022-01-11 | 浙江七色彩虹印染有限公司 | 一种涤纶低温染色携染剂及其制备方法和应用 |
JP7732213B2 (ja) * | 2021-03-29 | 2025-09-02 | セイコーエプソン株式会社 | 組成物セットおよび捺染方法 |
Citations (6)
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BE635252A (cs) * | ||||
BE638513A (cs) * | ||||
GB479341A (en) * | 1936-06-03 | 1938-02-03 | British Celanese | Improvements in the treatment of filaments, threads, fabrics, films, and like materials |
FR2226504A1 (cs) * | 1973-04-19 | 1974-11-15 | Ciba Geigy Ag | |
EP0009199A1 (de) * | 1978-09-22 | 1980-04-02 | Hoechst Aktiengesellschaft | Verfahren zur Vorbehandlung von Cellulosefasern, die nach dem Thermotransferverfahren bedruckt werden |
EP0546476A1 (de) * | 1991-12-07 | 1993-06-16 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung eines modifizierten Faser- materials und Verfahren zum Färben des modifizierten Fasermaterials mit anionischen Farbstoffen |
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DE2644436C3 (de) * | 1976-10-01 | 1980-03-13 | Bayer Ag, 5090 Leverkusen | Verfahren zum Färben von Cellulose-Textilmaterialien nach Klotzverfahren |
DE2835035B2 (de) * | 1978-08-10 | 1980-10-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zum Färben von Cellulosefasern mit Reaktivfarbstoffen nach der Ausziehmethode |
JPS55152875A (en) * | 1979-05-14 | 1980-11-28 | Mitsubishi Chem Ind | Anthraquinone dyestuff for cellulose containing fibers |
US4676803A (en) * | 1979-07-07 | 1987-06-30 | Bayer Aktiengesellschaft | Reactive azo dyestuffs, free from anionic groups and containing a basic group and halogenotriazinyl radical and useful for dyeing cellulose/polyester |
US4319881A (en) * | 1979-11-05 | 1982-03-16 | Ciba-Geigy Corporation | Process for printing or pad dyeing of textile material made from cellulose fibres, or from mixtures thereof with synthetic fibres |
-
1993
- 1993-08-13 DE DE4327301A patent/DE4327301A1/de not_active Withdrawn
-
1994
- 1994-07-12 TW TW083106316A patent/TW290604B/zh active
- 1994-08-05 EP EP94112297A patent/EP0638686A1/de not_active Withdrawn
- 1994-08-11 US US08/288,839 patent/US5498267A/en not_active Expired - Fee Related
- 1994-08-12 BR BR9403236A patent/BR9403236A/pt not_active Application Discontinuation
- 1994-08-12 JP JP6190810A patent/JPH07145574A/ja not_active Withdrawn
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BE638513A (cs) * | ||||
GB479341A (en) * | 1936-06-03 | 1938-02-03 | British Celanese | Improvements in the treatment of filaments, threads, fabrics, films, and like materials |
FR2226504A1 (cs) * | 1973-04-19 | 1974-11-15 | Ciba Geigy Ag | |
EP0009199A1 (de) * | 1978-09-22 | 1980-04-02 | Hoechst Aktiengesellschaft | Verfahren zur Vorbehandlung von Cellulosefasern, die nach dem Thermotransferverfahren bedruckt werden |
EP0546476A1 (de) * | 1991-12-07 | 1993-06-16 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung eines modifizierten Faser- materials und Verfahren zum Färben des modifizierten Fasermaterials mit anionischen Farbstoffen |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0690166A3 (de) * | 1994-06-29 | 1996-05-01 | Hoechst Ag | Verfahren zum Färben aminierter Cellulose-/Polyester-Mischgewebe mit faserreaktiven Dispersionsfarbstoffen |
US5578088A (en) * | 1994-06-29 | 1996-11-26 | Hoechst Aktiengesellschaft | Process for dyeing aminated cellulose/polyester blend fabric with fiber-reactive disperse dyestuffs |
WO2004081279A1 (de) * | 2003-03-13 | 2004-09-23 | Lenzing Aktiengesellschaft | Verfahren zum färben einer mischung aus zwei oder mehr unterschiedlichen fasertypen |
Also Published As
Publication number | Publication date |
---|---|
TW290604B (cs) | 1996-11-11 |
US5498267A (en) | 1996-03-12 |
DE4327301A1 (de) | 1995-02-16 |
BR9403236A (pt) | 1995-04-11 |
JPH07145574A (ja) | 1995-06-06 |
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