ES2692440T3 - Colorantes ácidos - Google Patents
Colorantes ácidos Download PDFInfo
- Publication number
- ES2692440T3 ES2692440T3 ES09780688.9T ES09780688T ES2692440T3 ES 2692440 T3 ES2692440 T3 ES 2692440T3 ES 09780688 T ES09780688 T ES 09780688T ES 2692440 T3 ES2692440 T3 ES 2692440T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- alkyl
- substituted
- unsubstituted
- substituents
- 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.)
- Active
Links
- 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 8
- 239000000980 acid dye Substances 0.000 title description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 98
- 125000001424 substituent group Chemical group 0.000 claims abstract description 58
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 40
- 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 claims abstract description 36
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 17
- 238000000034 method Methods 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 238000007639 printing Methods 0.000 claims description 13
- 239000004952 Polyamide Substances 0.000 claims description 9
- 229920002647 polyamide Polymers 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000000975 dye Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000835 fiber Substances 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- -1 isobutyl (2-methylpropyl) Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- GVAJGFIURUODAH-UHFFFAOYSA-N 4-[1-(4-aminophenyl)-2-ethylhexyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C(CC)CCCC)C1=CC=C(N)C=C1 GVAJGFIURUODAH-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
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 241001416177 Vicugna pacos Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 210000000077 angora Anatomy 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 238000009835 boiling Methods 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
- 210000000085 cashmere Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000004744 fabric Substances 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 150000002739 metals Chemical class 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001778 nylon Polymers 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 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
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
-
- 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
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08160945 | 2008-07-23 | ||
| EP08160945 | 2008-07-23 | ||
| PCT/EP2009/059128 WO2010010032A2 (en) | 2008-07-23 | 2009-07-16 | Acid dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2692440T3 true ES2692440T3 (es) | 2018-12-03 |
Family
ID=40149728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09780688.9T Active ES2692440T3 (es) | 2008-07-23 | 2009-07-16 | Colorantes ácidos |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2307508B1 (enExample) |
| JP (1) | JP2011528740A (enExample) |
| KR (1) | KR20110031504A (enExample) |
| CN (1) | CN102105538B (enExample) |
| BR (1) | BRPI0915988B1 (enExample) |
| ES (1) | ES2692440T3 (enExample) |
| MX (1) | MX2011000824A (enExample) |
| PT (1) | PT2307508T (enExample) |
| TW (1) | TWI583672B (enExample) |
| WO (1) | WO2010010032A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2868703A1 (en) * | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for their production and their use |
| EP2910608B1 (en) * | 2014-02-25 | 2017-05-31 | Archroma IP GmbH | Dimeric anionic monoazo dyes |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124566A (en) * | 1964-03-10 | Disazo dyestuffs | ||
| US4143034A (en) * | 1977-03-09 | 1979-03-06 | Sterling Drug Inc. | Polyaminomethylated monoazo and disazo colorants |
| JPS5930509A (ja) * | 1982-08-13 | 1984-02-18 | Fuji Photo Film Co Ltd | カラ−固体撮像素子 |
| JPS59101607A (ja) * | 1982-12-02 | 1984-06-12 | Fuji Photo Film Co Ltd | カラ−撮像装置 |
| JPS62156180A (ja) * | 1985-12-28 | 1987-07-11 | Ricoh Co Ltd | インクジエツト記録用水性インク |
| US5068319A (en) * | 1990-03-29 | 1991-11-26 | Hoechst Celanese Corporation | Biz-diazotized diaryl diamine coupled dyes having improved solubility in organic solvent |
| KR100309901B1 (ko) * | 1993-02-02 | 2002-09-25 | 스미또모 가가꾸 고오교오 가부시끼가이샤 | 칼라필터용아조염료및칼라필터의제조방법 |
-
2009
- 2009-07-16 PT PT09780688T patent/PT2307508T/pt unknown
- 2009-07-16 JP JP2011519127A patent/JP2011528740A/ja active Pending
- 2009-07-16 KR KR1020117004071A patent/KR20110031504A/ko not_active Ceased
- 2009-07-16 ES ES09780688.9T patent/ES2692440T3/es active Active
- 2009-07-16 CN CN200980128433.2A patent/CN102105538B/zh not_active Expired - Fee Related
- 2009-07-16 EP EP09780688.9A patent/EP2307508B1/en not_active Not-in-force
- 2009-07-16 WO PCT/EP2009/059128 patent/WO2010010032A2/en not_active Ceased
- 2009-07-16 BR BRPI0915988-6A patent/BRPI0915988B1/pt not_active IP Right Cessation
- 2009-07-16 MX MX2011000824A patent/MX2011000824A/es active IP Right Grant
- 2009-07-22 TW TW098124755A patent/TWI583672B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0915988B1 (pt) | 2019-03-26 |
| BRPI0915988A2 (pt) | 2018-10-30 |
| TW201012804A (en) | 2010-04-01 |
| CN102105538A (zh) | 2011-06-22 |
| TWI583672B (zh) | 2017-05-21 |
| CN102105538B (zh) | 2014-10-15 |
| JP2011528740A (ja) | 2011-11-24 |
| EP2307508A2 (en) | 2011-04-13 |
| WO2010010032A3 (en) | 2010-07-29 |
| MX2011000824A (es) | 2011-02-25 |
| WO2010010032A2 (en) | 2010-01-28 |
| PT2307508T (pt) | 2018-11-13 |
| KR20110031504A (ko) | 2011-03-28 |
| EP2307508B1 (en) | 2018-09-05 |
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