TWI588214B - 酸性染料之用途 - Google Patents
酸性染料之用途 Download PDFInfo
- Publication number
- TWI588214B TWI588214B TW098122066A TW98122066A TWI588214B TW I588214 B TWI588214 B TW I588214B TW 098122066 A TW098122066 A TW 098122066A TW 98122066 A TW98122066 A TW 98122066A TW I588214 B TWI588214 B TW I588214B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- unsubstituted
- dye
- parts
- group
- Prior art date
Links
- 239000000980 acid dye Substances 0.000 title description 7
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 title description 4
- 238000004043 dyeing Methods 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000004952 Polyamide Substances 0.000 claims description 13
- 229920002647 polyamide Polymers 0.000 claims description 13
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
- 238000007639 printing Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 239000002657 fibrous material Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 12
- -1 isobutyl (2-methylpropyl) Chemical group 0.000 description 11
- 239000000835 fiber Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241001416177 Vicugna pacos Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 210000000085 cashmere Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009500 colour coating Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 210000000050 mohair Anatomy 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
- C09B35/031—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound containing a six membered ring with one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
- C09B35/21—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene of diarylmethane or triarylmethane
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/26—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl urea
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
- C09B35/30—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O— from two identical coupling components
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
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- 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
-
- 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
- D06P3/001—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/021—Material containing basic nitrogen using acid dyes
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- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
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- 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
- D06P3/6008—Natural or regenerated cellulose using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H13/00—Pulp or paper, comprising synthetic cellulose or non-cellulose fibres or web-forming material
- D21H13/10—Organic non-cellulose fibres
- D21H13/20—Organic non-cellulose fibres from macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H13/26—Polyamides; Polyimides
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Description
本發明係關於一種酸性染料之新穎用途，其製備方法及其用於為有機基材染色的用途。
眾所周知酸性染料，且亦了解具有橋連部分的染料。驚訝的發現用於為多聚纖維(特定言之聚醯胺纖維)進行大量染色之某些酸性染料可用於在水性介質中為紡織纖維染色。該等聚醯胺纖維可以為人造聚醯胺纖維(所有尼龍種類)或天然聚醯胺纖維，例如：羊毛或蠶絲。
本發明係關於一種通式(I)化合物之用途 其中R0表示經取代的C1至C4烷基或未經取代的C1至C4烷基，R1表示H、經取代的C1至C4烷基或未經取代的C1至C4烷基、磺基、-CO-NH-(C1至C4烷基)或CN，R2表示H或未經取代的C1至C4烷基，R3表示H、磺基、經取代之C1至C4烷基或未經取代的C1至C4烷基、經取代的C1至C4烷氧基或未經取代的C1至C4烷氧基，R4表示H、磺基、經取代的C1至C4烷基或未經取代的C1至C4烷基、經取代的C1至C4烷氧基或未經取代的C1至C4烷氧基，其係用於在水性介質中，為由天然或合成的聚醯胺組成之纖維材料進行染色或印刷。
較佳之式(I)化合物具有至少一個陰離子性取代基，以一個或兩個或三個陰離子性取代基較佳，其中以兩個陰離子性取代基最佳。
式(I)化合物之至少一個陰離子性取代基之位置較佳係由取代基R1及/或R3中之一決定。其中一個取代基之較佳位置亦可能意味著該取代基係陰離子性基團。
較佳之陰離子性取代基為羧基及/或磺基，並且以磺基特別佳。
經取代之C1至C4烷基之較佳取代基係選自以下取代基：-OH、-O(C1至C4-烷基)、-SO3H、-COOH、-NH(C1至C4-烷基)。經取代之C1至C4烷基之更佳取代基係選自以下取代基：-OH、-O(C1至C4-烷基)、-SO3H、-COOH、-NH(C1至C4-烷基)。烷基為直鏈或分支鏈。最佳之烷基為甲基、乙基、丙基、異丙基、丁基、異丁基(2-甲基丙基)、戊基、異戊基(3-甲基丁基)、己基、庚基、辛基或壬基。
經取代之C1至C4烷氧基之較佳取代基係選自以下取代基：-OH、-O(C1至C4-烷基)、-SO3H、-COOH、-NH(C1至C4-烷基)。烷氧基為直鏈或分支鏈。
經取代之芳基之較佳取代基係選自以下取代基：-OH、-O(C1至C4-烷基)、-SO3H、經取代的C1至C4烷基、未經取代的烷基、經取代的C1至C4烷氧基與未經取代的C1至C4烷氧基。
在較佳的通式(I)化合物中：R0表示未經取代的C1至C2烷基，R1表示經取代的C1至C2烷基或未經取代的C1至C2烷基、磺基、-CO-NH-(C1至C2烷基)或CN，R2表示未經取代的C1至C3烷基，R3表示H、磺基、未經取代的C1至C2烷基、未經取代的C1至C2烷氧基，R4表示H、未經取代的C1至C2烷基、未經取代的C1至C2烷氧基。
在甚至更佳之通式(I)化合物中：R0表示烷基，R1表示-CH2-SO3H或-CN，R2表示乙基，R3表示H、甲基、甲氧基或磺基，R4表示H、甲基或甲氧基。
在最佳之通式(I)化合物中：R0表示甲基，R1表示-CH2-SO3H基，R2表示乙基，R3表示H、甲基，R4表示H、甲基或甲氧基(較佳為H)
較佳之式(I)化合物如式(I')
本發明亦提供一種製備式(I)化合物之方法。本發明之式(I)化合物可在常規條件下，用常規的方法製備。
在此等方法中，式(II)化合物(由文獻資料所知)之兩個胺基官能團
依一般方式重氮化，及偶合至共兩當量之式(III)化合物上
在該過程中，該特定二胺冷卻至0至10℃或0至5℃較佳，並加入亞硝醯基硫酸或亞硝酸鈉，使其重氮化。之後，經雙-重氮化的二胺可與化合物(III)反應，在水溶液中較佳。
可用常規方法，自反應介質中分離式(I)染料，例如：使用鹼金屬鹽鹽析，過濾並乾燥，如果適合時，在減壓及加溫的條件下進行。
視反應及/或分離條件所定，式(I)染料可呈游離酸、鹽或混合鹽的形式獲得，其中混合鹽包含一個或多個選自鹼金屬離子中的陽離子，例如鈉離子、或銨離子或烷基銨陽離子，例如一-、二-或三-甲基或-乙基銨陽離子。染料可以用常規的方法，從游離酸轉化成鹽或混合鹽，或反之亦然，或從一種鹽轉化成另一種鹽。如有需要，染料可進一步透析過濾純化，從陰離子性染料粗產物中分離出不需要的鹽與合成的副產物。
自粗製染料溶液中排除不需要的鹽與合成的副產物及部份排除水之方法係使用半通透膜，在施加壓力下進行，得到沒有不要的鹽與合成之副產物之染料溶液，且若有需要可用常規方法得到固體形式。
式(I)染料與其鹽特別適用於為由黃色調或黃綠色調之天然或合成聚醯胺組成之纖維材料進行染色或印刷。式(I)染料與其鹽適用於生產噴墨印刷墨水，並可使用此等噴墨印刷墨水印刷由天然或合成聚醯胺或纖維素組成之纖維材料(例如：紙)。
本發明因此在另一態樣提供一種以式(I)染料、其鹽與混合物於在天然或合成聚醯胺組成之纖維材料上進行染色及/或印刷之用途。另一態樣為噴墨印刷墨水之製法，及印刷在由天然或合成聚醯胺組成之纖維材料上之用途。
在水性介質中的染色或來自水性介質的染色係依已知方法進行，例如，在Ullmanns Encyklopdie der technischen Chemie,4版，1982,22卷，658-673卷或M.Peter與H.K.Rouette,rundlagen der Textilveredlung編輯，第13版,1989,535-556頁與566-574頁中說明之染色過程。在盡染過程中之染色溫度較佳為30至140℃，80至120℃更佳，而80至100℃最佳，並且液體比率範圍較佳為3：1至40：1。
因此，本發明亦提供一種在水性介質中，在由天然或合成聚醯胺組成之纖維材料上進行染色或印刷之方法，其包括之步驟為提供一種由天然或合成聚醯胺組成之基材，提供一種式(I)化合物(其中所有取代基均如上定義)及其鹽或混合物，並且使用該化合物或化合物群、其鹽或其混合物在該基材上染色或印刷或噴墨印刷。
待染色之基材可呈例如紗、紡織布、毛圈編織布或地毯之形式。甚至可以在精細的基材(例如羔羊毛、喀什米爾羊絨、羊駝毛與馬海毛)上永久存在全成型染色。本發明之染料特別適用於為細絲纖維(微纖維)染色。
根據本發明之染料及其鹽可與已知的酸性染料高度相容。因此，式(I)染料、其鹽或混合物可單獨用於染色或印刷方法，或另作為與其它同類酸性染料(亦即，與具有類似染色性質(如，例如色牢度及基材在染缸中之盡染率)的酸性染料)的組合色調染料或作為印刷組合物中之組分。本發明之染料可特別與具有適宜發色團的其他染料一起使用。於組合色調染料或印刷組合物中之染料比率係由所需得到的色彩指定。
如上所述，式(I)染料極適用於為天然或合成聚醯胺(亦即羊毛、絲及所有尼龍類型)染色，其中每一個自水性介質中得到的染色具有高色牢度，尤其可得到良好的耐光性與耐濕性(沖洗、鹼性汗液)。式(I)染料及其鹽具有高盡染率。式(I)染料及其鹽的上色能力同樣非常良好。在同一基材上的同色調染色之品質出衆。且在人造光下所有染色具有一致色彩。此外耐蒸與耐煮性良好。
式(I)染料之決定性優勢在於其不含金屬且提供相當均勻的染色。
根據本發明之化合物可用於單獨染色或由於其良好的相容性，因此可作為組合物的要素之一，與其他具有類似的染色性質(例如在整體色牢度、盡染值等等方面)之同等級染料組合。所得的組合色調染色具有類似個別染色的色牢度。
本發明之式(I)染料亦可作為三原色染色或印刷之黃色組成。三原色染色或印刷可利用所有常用的已知染色與印刷方法，如，例如：連續法、盡染法、泡沫染色方法與噴墨印刷方法。
用於本發明製法之三原色染色混合物中之個別染色組成份之組合物依所需要的色彩決定。例如棕色色彩較佳係使用20%至40%重量比之黃色組成份、40%至60%重量比之本發明橙色或紅色組成份與10%至20%重量比之藍色組成份。
如上所述，黃色組成份可由如式(I)之單一成份或不同橙色個別成份之混合物組成。以兩個與三個組成份較佳。
特別佳之紅色及/或藍色色彩組成份分別說明於WO 2002/46318或WO 99/51681。
在以下實施例中，份量數及百分比係按重量計算，並且溫度以攝氏溫度表示。
取24.8份(0.1 mol)之3,3'-二胺基-二苯基碸根據已知方法，使用13.8份(0.2 mol)之亞硝酸鈉，於0至5℃，於200份水與60份鹽酸(約30%)中，進行四氮化。取49.4份(0.2 mol)如下式化合物
下表1包含的染料可以採用實例1所述之相似方法，使用相應的起始材料製備。這些染料在聚醯胺纖維與羊毛上形成之黃色具有良好耐光度與耐濕性。λmax以nm表示(奈米，於1%醋酸溶液中測定)
取100份的尼龍-6布料浸入溫度40℃之染缸中，其係由2000份水、1份弱陽離子性活性均染劑(其基於乙氧基化胺基丙基脂肪酸醯胺，並且對染料具有親和力)、0.25份製備實例2之染料組成，並用1至2份40%醋酸將pH調至5。於40℃下10分鐘之後，依每分鐘升高1℃之速度加熱染缸至98℃，之後煮沸45至60分鐘。此後，以15分鐘時間降溫至70℃。將染物移出染缸，依次以熱水及冷水洗滌後，乾燥。所獲得的結果係具有極佳耐光性與耐濕性之黃色聚醯胺染色加工品。
取100份的尼龍-6,6布料浸入溫度40℃之染缸，其係由2000份水，1份弱陽離子性活性均染劑(其基於乙氧基化胺基丙基脂肪酸醯胺並且對染料具有親和力)、0.3份製備實例2之染料組成，並用1至2份40%醋酸將pH調至5.5。於40℃下10分鐘之後，以每分鐘上升1.5℃之速度加熱染缸至120℃，並維持在此溫度15至25分鐘。此後，以25分鐘時間降溫至70℃。將染物移出染缸，依次以熱水與冷水洗滌後再乾燥。所獲得的結果係具有良好均染性、極佳耐光性與耐濕性之黃色聚醯胺染物。
取100份的羊毛布料浸入溫度40℃之染缸，其係由4000份水，1份弱兩性均染劑(其係基於硫酸化之乙氧基化脂肪酸醯胺並且對染料具有親和力)、0.4份製備實例2之染料組成，並用1至2份40%醋酸將pH調至5。於40℃下10分鐘之後，以每分鐘上升1℃之速度加熱染缸至沸騰，之後保持煮沸40至60分鐘。此後，以20分鐘時間降溫至70℃。將染物移出染缸，依次以熱水與冷水洗滌後再乾燥。所獲得之結果係具有極佳耐光性與耐濕性之黃色羊毛染物。
取100份尼龍-6編織材料於50℃由下列組成之溶液中軋染：40份製備實例2之染料，100份尿素，20份基於丁基二甘醇之非離子性增溶劑，15-20份醋酸(將pH調至4)，10份弱陽離子性-活性均染劑，其基於乙氧基化胺\基丙基脂肪酸醯胺，並對染料具有親和力，810-815份水(將軋染液補足至1000份)。
將所浸漬之材料捲起，並置於在飽和蒸汽條件下之85至98℃蒸氣室內3至6小時進行固定。然後依次以熱水與冷水洗滌染物並乾燥。獲得的結果為在材料上具有良好均染性及良好耐光性與耐濕性之黃色尼龍染物
使用每100份含有以下組成之軋染液軋染一種由尼龍-6組成紡織物之大量薄片材料：1份製備實例2之染料，4份自商品購得之基於刺槐豆粉醚之增稠劑，2份較高碳數烷基苯酚之非離子性環氧乙烷加合物，1份60%乙酸。
接下來用每1000份含有以下組成之糊液印刷：20份自商品之購得之烷氧基化脂肪烷基胺(替代產品)，20份自商品購得之基於刺槐豆粉醚之增稠劑，印刷物於100℃之飽和水蒸氣中固定6分鐘，洗滌並乾燥。結果獲得具有黃色與白色圖案之均染顏色塗覆材料。
取100份尼龍-6,6布料紡織品浸入溫度40℃之染缸，其係由2000份水，1份弱陽離子性活性均染劑(其基於乙氧基化胺基丙基脂肪酸醯胺並且對染料具有親和力)、1.5份實例2染料、0.2份專利申請案WO 2002/46318製備實例8之紅色染料：
用1至2份40%醋酸將pH值調至5。於40℃下10分鐘之後，以每分鐘上升1℃之速度加熱染缸至98℃，之後煮沸45至60分鐘。此後，以15分鐘時間降溫至70℃。將染物移出染缸，依次以熱水與冷水洗滌後再乾燥。所獲得的結果係具有極佳耐光性與耐濕性之灰色聚醯胺染物。
取100份經過鉻韖及合成性再韖之濕性刮平全粒面皮革於55℃之染缸中染色30分鐘，其係由300份水與2份製備實例2染料組成。在添加4份60%亞硫酸化魚油之乳液後，將皮革進行加脂處理45分鐘。然後用8.5%甲酸酸化，並碾磨10分鐘(最終染缸之pH為3.5至4.0)。然後洗滌皮革，滴乾，並依一般方式進行最後修飾。結果得到均染清晰橙色彩並具有良好色牢度之染色皮革。
亦可由染料1、3與4進行應用實例A至G，得到相似結果。
取3份製備實例3染料溶於60℃之82份去礦物質水與15份二乙二醇中。冷卻至室溫，並得到橙色印刷墨水，其非常適合噴墨印刷在紙或聚醯胺與羊毛紡織品上。
亦可由染料1、3與4進行應用實例H，得到相似結果。
染缸係由1000份水，80份煆燒之芒硝鹽，1份之硝基苯-3-磺酸鈉與1份製備實例2之染料組成，以10分鐘時間加熱染缸至80℃。然後，添加100份絲光棉。接下來於80℃下染色5分鐘，並且以15分鐘時間加熱至95℃。於95℃下10分鐘後，添加3份碳酸鈉，接著於95℃下20分鐘後再加7份碳酸鈉，30分鐘後再加10份碳酸鈉30分鐘。此後，持續在95℃下染色60分鐘。將染好之材料移出染缸並於流動之去礦物質水中洗滌3分鐘。接下來每次使用5000份沸騰之去礦物質水中洗滌10分鐘，共洗滌2次，然後在流動之去礦物質水中，於60℃下洗滌3分鐘，並且以冷自來水洗滌1分鐘。乾燥後得到具有良好色牢度之明亮黃色染色棉。
取0.2份製備實例2之染料溶於100份熱水中，並將其冷卻至室溫。添加此溶液至已於含2,000份水之打漿機中攪爛之100份經化學漂白之亞硫酸鹽紙漿中。在材料混合15分鐘後，依一般方式使用樹脂上膠劑與硫酸鋁上膠。從此材料中生產出來之紙為具有良好耐濕性之黃色調。
亦可由染料1、3與4進行應用實例I與J，得到相似結果。
Claims (5)
- 一種通式(I)化合物之用途，
- 如請求項1之用途，其特徵在於式(I)化合物具有至少一個陰離子性取代基。
- 如請求項2之用途，其特徵在於R0 表示未經取代的C1至C2烷基，R1 表示經取代的C1至C2烷基或未經取代的C1至C2烷基、磺基、-CO-NH-(C1至C2烷基)或CN，R2 表示未經取代的C1至C3烷基，R3 表示H、磺基、未經取代的C1至C2烷基、未經取代的C1至C2烷氧基，R4 表示H、未經取代的C1至C2烷基、未經取代的C至C2烷氧基。
- 如請求項3之用途，其特徵在於R0 表示甲基，R1 表示-CH2-SO3H或-CN，R2 表示乙基，R3 表示H、甲基、甲氧基或磺基，R4 表示H、甲基或甲氧基。
- 如請求項1之用途，其中式(I)化合物製法係由式(II)化合物中兩個胺官能基均進行重氮化，
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| EP08011926 | 2008-07-02 | ||
| EP08160083 | 2008-07-10 |
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| TWI588214B true TWI588214B (zh) | 2017-06-21 |
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| TW098122066A TWI588214B (zh) | 2008-07-02 | 2009-06-30 | 酸性染料之用途 |
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| KR (2) | KR101649484B1 (zh) |
| CN (2) | CN102076780B (zh) |
| BR (2) | BRPI0914939B1 (zh) |
| ES (2) | ES2383581T3 (zh) |
| MX (2) | MX2010014526A (zh) |
| PT (2) | PT2307510E (zh) |
| TW (2) | TWI461408B (zh) |
| WO (2) | WO2010000780A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI659138B (zh) * | 2017-10-25 | 2019-05-11 | Everlight Chemical Industrial Corporation | 酸性染料組成物及其於染尼龍織物上的用途 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2258683A1 (en) * | 2009-05-14 | 2010-12-08 | Clariant International Ltd. | Bisazo compounds |
| PT2258685E (pt) * | 2009-05-14 | 2013-12-10 | Clariant Finance Bv Ltd | Compostos bisazo |
| ES2403068T3 (es) * | 2010-07-29 | 2013-05-13 | Clariant Finance (Bvi) Limited | Tintes ácidos |
| ES2497191T3 (es) * | 2011-10-22 | 2014-09-22 | Clariant International Ltd. | Colorantes ácidos trisazoicos basados en piridonas |
| DE102013012244A1 (de) | 2013-07-24 | 2015-01-29 | Clariant International Ltd. | Verwendung von Disazoverbindungen für Color Filter |
| DE102013012855A1 (de) * | 2013-08-01 | 2015-02-05 | Clariant International Ltd. | Zusammensetzungen, enthaltend Disazofarbstoffe und Pigmente |
| EP2868708A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal-free acid dyes, process for the production thereof and their use |
| EP2868715A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for the production thereof and their use |
| EP2868705A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for their production and their use |
| WO2015062929A1 (en) | 2013-10-29 | 2015-05-07 | Dystar Colours Distribution Gmbh | Acid dyes, process for the production thereof and their use |
| EP2868709A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for the production thereof and their use |
| ES2637479T3 (es) * | 2013-10-29 | 2017-10-13 | Dystar Colours Distribution Gmbh | Tintes ácidos, proceso para su producción y su utilización |
| EP2868712A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for the production thereof and their use |
| CN104629401B (zh) * | 2014-12-30 | 2017-03-29 | 南京工业大学 | 一种双偶氮分散染料及其制备方法和用途 |
| CN116023795A (zh) * | 2022-12-22 | 2023-04-28 | 苏州科法曼化学有限公司 | 一种染料化合物及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54143439A (en) * | 1978-04-28 | 1979-11-08 | Ciba Geigy Ag | Azo dye sulfonate and preparation thereof |
| DE3035307A1 (de) * | 1979-09-24 | 1981-04-09 | CIBA-GEIGY AG, CH 4002 Basel | Disazoverbindungen |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH552661A (de) * | 1968-11-12 | 1974-08-15 | Ciba Geigy Ag | Verfahren zur herstellung neuer azofarbstoffe. |
| DE2004487C3 (de) * | 1970-01-31 | 1979-12-06 | Basf Ag, 6700 Ludwigshafen | Wasserlösliche Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| GB1331261A (en) * | 1970-03-23 | 1973-09-26 | Ici Ltd | Water-soluble azo dyestuffs containaing hydroxypyridine residues |
| GB1331445A (en) | 1970-03-31 | 1973-09-26 | Ici Ltd | Azo dyestuffs |
| US3932122A (en) * | 1970-10-23 | 1976-01-13 | Ciba-Geigy Ag | Azo compounds, their manufacture and use |
| US4359418A (en) * | 1979-03-12 | 1982-11-16 | Ciba-Geigy Corporation | Amine salts of azo dyestuffs of the pyridone series |
| US5352334A (en) * | 1985-03-30 | 1994-10-04 | Sandoz Ltd. | The use of metal-free sulfo group free basic disazo compounds containing two identical 6-hydroxypyrid-2-one coupling component radicals for producing colored paper |
| CH667464A5 (de) * | 1985-03-30 | 1988-10-14 | Sandoz Ag | Sulfonsaeuregruppenfreie basische azoverbindungen. |
| DE4227590A1 (de) * | 1992-08-20 | 1994-02-24 | Basf Ag | Azofarbstoffe mit einer Kupplungskomponente aus der Reihe der N-(Hydroxysulfonylphenylalkyl)pyridone |
| GB0103240D0 (en) * | 2001-02-09 | 2001-03-28 | Clariant Int Ltd | Organic compounds |
| ATE380221T1 (de) * | 2001-03-09 | 2007-12-15 | Ciba Sc Holding Ag | Pyridon-farbstoffe, verfahren zu deren herstellung und verwendung in der herstellung von gefaerbten kunstoffen und polymeren farbpartikel |
| JP4271446B2 (ja) * | 2001-05-07 | 2009-06-03 | チバ ホールディング インコーポレーテッド | ピリドン染料、それらの製造方法ならびに着色プラスチックまたはポリマー性カラー粒子の製造におけるそれらの使用 |
| US6713614B2 (en) * | 2002-06-27 | 2004-03-30 | Xerox Corporation | Dimeric azo pyridone colorants |
| WO2008012322A1 (en) * | 2006-07-28 | 2008-01-31 | Clariant International Ltd | Basic bisazo compounds |
-
2009
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- 2009-07-01 CN CN2009801247526A patent/CN102076780B/zh active Active
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- 2009-07-01 WO PCT/EP2009/058264 patent/WO2010000780A1/en not_active Ceased
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54143439A (en) * | 1978-04-28 | 1979-11-08 | Ciba Geigy Ag | Azo dye sulfonate and preparation thereof |
| DE3035307A1 (de) * | 1979-09-24 | 1981-04-09 | CIBA-GEIGY AG, CH 4002 Basel | Disazoverbindungen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI659138B (zh) * | 2017-10-25 | 2019-05-11 | Everlight Chemical Industrial Corporation | 酸性染料組成物及其於染尼龍織物上的用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110031359A (ko) | 2011-03-25 |
| ES2383581T3 (es) | 2012-06-22 |
| MX2010014526A (es) | 2011-02-22 |
| BRPI0914939B1 (pt) | 2018-06-19 |
| CN102076780A (zh) | 2011-05-25 |
| EP2307510B1 (en) | 2012-02-29 |
| KR20110039542A (ko) | 2011-04-19 |
| BRPI0913833B1 (pt) | 2018-06-12 |
| KR101760661B1 (ko) | 2017-07-24 |
| WO2010000780A1 (en) | 2010-01-07 |
| JP2015038264A (ja) | 2015-02-26 |
| EP2307510A1 (en) | 2011-04-13 |
| TWI461408B (zh) | 2014-11-21 |
| MX2010014525A (es) | 2011-02-22 |
| ES2383580T3 (es) | 2012-06-22 |
| BRPI0914939A2 (pt) | 2015-10-20 |
| EP2307509A1 (en) | 2011-04-13 |
| TW201012802A (en) | 2010-04-01 |
| CN102076779B (zh) | 2013-08-21 |
| CN102076779A (zh) | 2011-05-25 |
| PT2307509E (pt) | 2012-04-12 |
| CN102076780B (zh) | 2013-08-21 |
| WO2010000779A1 (en) | 2010-01-07 |
| BRPI0913833A2 (pt) | 2015-10-20 |
| EP2307509B1 (en) | 2012-02-29 |
| TW201005043A (en) | 2010-02-01 |
| PT2307510E (pt) | 2012-04-12 |
| KR101649484B1 (ko) | 2016-08-19 |
| JP2011526636A (ja) | 2011-10-13 |
| JP2011526635A (ja) | 2011-10-13 |
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