TWI422647B - 酸染料 - Google Patents
酸染料 Download PDFInfo
- Publication number
- TWI422647B TWI422647B TW096117063A TW96117063A TWI422647B TW I422647 B TWI422647 B TW I422647B TW 096117063 A TW096117063 A TW 096117063A TW 96117063 A TW96117063 A TW 96117063A TW I422647 B TWI422647 B TW I422647B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- unbranched
- branched
- Prior art date
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 7
- 239000000980 acid dye Substances 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 238000004043 dyeing Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 229920002647 polyamide Polymers 0.000 claims description 9
- 210000002268 wool Anatomy 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- -1 alkali metal salt Chemical class 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 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
- 239000000463 material Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004677 Nylon Substances 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
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- BQGRVFPPZJPWPB-UHFFFAOYSA-N 3-[(n-ethylanilino)methyl]benzenesulfonic acid Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 BQGRVFPPZJPWPB-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
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 239000003086 colorant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010411 cooking 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
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 239000010446 mirabilite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 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
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002759 woven fabric Substances 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
- C09B35/025—Disazo dyes characterised by two coupling components of the same type in which the coupling component is an amine or polyamine
-
- 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
- C09B35/037—Disazo dyes characterised by two coupling components of different types
-
- 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
- C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
- C09B35/215—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene of diarylethane or diarylethene
-
- 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—
-
- 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
- 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—
- C09B35/32—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 different 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
-
- 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
- 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
Description
本發明係關於新穎酸染料、其製備方法及其用於染色有機基材之用途。
酸染料已為人們習知且亦已習知具有橋接成員之染料。然而,業內仍需要具有經改良性質之酸染料。
本發明提供通式(I)之化合物
其中R1
、R2
、R9
及R10
皆獨立為未經取代無支鏈C1-6
烷基或未經取代具支鏈C3-6
烷基或經取代無支鏈C1-6
烷基或經取代具支鏈C3-6
烷基、或芳基、或-(CH2
)p
-芳基,其中p=1、2、3或4,R3
及R8
為氫、未經取代無支鏈C1-6
烷基或未經取代具支鏈C3-6
烷基或經取代無支鏈C1-6
烷基或經取代具支鏈C3-6
烷基或未經取代無支鏈C1-6
烷氧基或未經取代具支鏈C3-6
烷氧基或經取代無支鏈C1-6
烷氧基或經取代具支鏈C3-6
烷氧基、或鹵素、或具有經取代或未經取代無支鏈C1-6
烷基之-NHCO-(C1-6
烷基)、或具有經取代或未經取代具支鏈C3-6
烷基之-NHCO-(C3-6
烷基)、或-NHCONH2
,BR係式-A-B-A-之橋接基團,其中A為經取代苯基或經取代萘基或未經取代苯基或未經取代萘基,且B為橋接-[(CR6
R7
)-(CR6'
R7'
)m
-(CR6"
R7"
)n
-(CR6'''
R7'''
)o
]-,其中m、n及o具有1或0之意義,且R6
、R7
、R6'
、R7'
、R6"
、R7"
、R6'''
及R7'''
皆獨立為氫、未經取代無支鏈C1-6
烷基、經取代無支鏈C1-6
烷基、經取代具支鏈C3-6
烷基或未經取代具支鏈C3-6
烷基、未經取代無支鏈C1-6
烷氧基、未經取代或經取代苯基或R6
與R7
一起或R6'
與R7'
一起或R6"
與R7"
一起或R6'''
與R7'''
一起形成一個五或六員脂肪族環,或B為橋接碸,或B為橋接磺醯胺或B為橋接甲醯胺或B為橋接,且式(I)化合物具有1、2或3個磺酸基。
在較佳之通式(I)化合物中,R1
及R9
皆為未經取代無支鏈C1-6
烷基或未經取代具支鏈C3-6
烷基或經取代無支鏈C1-6
烷基或經取代具支鏈C3-6
烷基,R2
及R10
皆為芳基、或-(CH2
)p
-芳基,其中p=1、2、3或4,R3
及R8
為氫、未經取代無支鏈C1-6
烷基或未經取代具支鏈C3-6
烷基或經取代無支鏈C1-6
烷基或經取代具支鏈C3-6
烷基或未經取代無支鏈C1-6
烷氧基或未經取代具支鏈C3-6
烷氧基或經取代無支鏈C1-6
烷氧基或經取代具支鏈C3-6
烷氧基,BR係式-A-B-A-之橋接基團,其中A為經取代苯基或經取代萘基或未經取代苯基或未經取代萘基,且B為橋接-[(CR6
R7
)-(CR6'
R7'
)m
-(CR6"
R7"
)n
-(CR6'''
R7'''
)o
]-,其中m、n及o具有1或0之意義,且R6
、R7
、R6'
、R7'
、R6"
、R7"
、R6'''
及R7'''
皆獨立為氫、未經取代無支鏈C1-6
烷基、經取代無支鏈C1-6
烷基、經取代具支鏈C3-6
烷基或未經取代具支鏈C3-6
烷基、未經取代無支鏈C1-6
烷氧基、未經取代或經取代苯基或R6
與R7
一起或R6'
與R7'
一起或R6"
與R7"
一起或R6'''
與R7'''
一起形成一個五或六員脂肪族環,或B為橋接碸,或B為橋接磺醯胺或B為橋接甲醯胺或B為橋接。
較佳地,1、2或3個磺酸基較佳係基團R1
、R2
、R9
及R10
上之取代基或其他取代基。若基團R1
、R2
、R9
及R10
中存在芳基部分,則較佳該等1、2或3個磺酸基連接至基團R1
、R2
、R9
及R10
之芳基部分。更佳地,該等1、2或3個磺酸基位於基團R2
及/或R10
上。在較佳之式(I)化合物中,該橋成員BR中無陰離子取代基。
該等較佳之式(I)化合物具有2個磺酸基。
芳基較佳為經取代苯基或經取代萘基或未經取代苯基或未經取代萘基。該等經取代芳基較佳經硝基或磺酸基取代。尤其較佳者係磺酸基作為該等芳基上之取代基。
極為較佳者進一步係其中R2
及/或R10
為經取代或未經取代-(CH2
)p
-苯基或經取代或未經取代-(CH2
)p
-萘基(其中p=1、2、3或4,較佳p為1或2)且其中極為較佳者為-CH2
-苯基之式(I)化合物。
該等較佳-CH2
-苯基較佳經硝基及/或磺酸基取代,極為較佳者係磺酸基作為該較佳-CH2
-苯基之取代基。
尤其較佳之-CH2
-苯基具有以下式
該等具支鏈C3-6
烷基或無支鏈C1-6
烷基及該等無支鏈C1-6
烷氧基或具支鏈C3-6
烷氧基可進一步經羥基或氰基取代。較佳地,該等烷基及/或烷氧基未經進一步取代。
在較佳之式(I)化合物中,該等較佳烷基及較佳烷氧基係甲基、乙基、丙基、甲氧基及乙氧基。極為較佳者係甲基、乙基及甲氧基。
在較佳之式(I)化合物中,該等尤其較佳橋具有結構(II-1)或(II-2)或(II-3)或(II-4)或(II-5):
或
或
或
或
其中R4
、R4'
、R5
及R5'
皆獨立為氫、未經取代無支鏈C1-6
烷基或未經取代具支鏈C3-6
烷基或經取代無支鏈C1-6
烷基或經取代具支鏈C3-6
烷基或未經取代無支鏈C1-6
烷氧基或未經取代具支鏈C3-6
烷氧基或經取代無支鏈C1-6
烷氧基或經取代具支鏈C3-6
烷氧基、或鹵素或具有經取代或未經取代無支鏈C1-6
烷基之-NHCO-(C1-6
烷基)、或具有經取代或未經取代具支鏈C3-6
烷基之-NHCO-(C3-6
烷基)、或-NHCONH2
,R6
、R7
、R6'
、R7'
、R6"
、R7"
、R6'''
及R7'''
皆獨立為氫、未經取代無支鏈C1-6
烷基、未經取代無支鏈C1-6
烷氧基、未經取代或經取代苯基,或R6
與R7
一起或R6'
與R7'
一起或R6"
與R7"
一起或R6'''
與R7'''
一起形成一個五或六員脂肪族環,或m、n及o具有1或0之意義。
根據橋結構(II-1)或(II-2)或(II-3)或(II-4),橋結構(II-3)係較佳橋BR。在較佳結構(II-3)中,m為1,n及o各自為0且具有以下結構(II-3')
其中R4'
、R5'
、R4
、R5
、R6
、R7
、R6'
及R7'
皆具有上述意義。
較佳地,R4'
與R5'
皆為氫且R4
及R5
皆獨立為氫、未經取代無支鏈C1-6
烷基或未經取代具支鏈C3-6
烷基、或經取代無支鏈C1-6
烷基或經取代具支鏈C3-6
烷基或未經取代無支鏈C1-6
烷氧基或未經取代具支鏈C3-6
烷氧基或經取代無支鏈C1-6
烷氧基或經取代具支鏈C3-6
烷氧基。最佳地,R4'
、R5'
、R4
及R5
各自皆為氫。
較佳地,R6
、R7
、R6'
、R7'
、R6"
、R7"
、R6'''
及R7'''
皆獨立為氫或甲基或乙基或苯基。最佳地,R6
、R7
、R6'
及R7'
各自為氫(且m為1,n及o各自為0)。
本發明亦提供一種製備式(I)化合物之方法。本發明之式(I)化合物可於常用條件下以常用方法製備。
在該等方法中,將自文獻中習知之下式(II)化合物的兩個銨官能團H2
N-BR-NH2
(II),方便地重氮化並全部偶合至2當量式(IIIa)化合物及式(IIIb)化合物
其中該等取代基各自皆如以上所定義且式(IIIa)化合物與式(IIIb)化合物之和係2當量。
熟悉該項技術者應清楚,在此一反應程序中將獲得不同可能化合物之統計混合物,其中該二胺(II)係經雙重氮化且然後與式(IIIa)與(IIIb)化合物之混合物反應。此外,在組份(IIIa)及/或(IIIb)中之一包含位置同分異構體之情況下,熟悉該項技術者應清楚,此同樣將獲得額外不同可能化合物之統計混合物。例如,式(IIIa)化合物可由化合物(IIIa')與(IIIa")組成,例如15重量%式(IIIa')化合物與85重量%式(IIIa")化合物
在該等方法中,將該具體二胺冷卻至0-10℃或較佳至0-5℃並藉由添加亞硝基硫酸或亞硝酸鈉重氮化。然後,使該雙重氮化二胺與化合物(IIIa)或與化合物(IIIb)、較佳在水溶液中反應。
式(I)染料可藉由已知方法從反應介質中分離出來,例如藉由用鹼金屬鹽鹽析、過濾及乾燥,若適宜在降低壓力及高溫下乾燥。
視反應及/或分離條件而定,式(I)染料可以游離酸、鹽或作為含有(例如)一或多種選自鹼金屬離子(例如鈉離子)、或銨離子或烷基銨陽離子(例如單-、二-、或三甲基-或-乙基銨陽離子)之陽離子的混合鹽存在。該染料可藉由傳統方法由游離酸轉化成鹽或混合鹽,或者反之,或由一種鹽轉化為另一種鹽。該染料可視需要藉由濾析進一步純化,在此情況下可將不期望的鹽及合成副產物自粗製陰離子染料中分離出去。
自粗製染料溶液中去除不期望鹽及合成副產物及部分去除水係借助半透膜藉由施加壓力來實施,藉此以常用方式獲得無不期望鹽及合成副產物之呈溶液形式且當需要時呈固體形式之染料。
式(I)染料及其鹽尤其適用於將由天然或合成聚醯胺構成之纖維材料染色或印刷成黃色至紫色色調。式(I)染料及其鹽代適用於生產噴墨印刷油墨且使用該等噴墨印刷油墨對由天然或合成聚醯胺或纖維素構成之纖維材料(例如紙)進行印刷。
因此,本發明之另一態樣提供以式(I)染料、其鹽及混合物於對由天然或合成聚醯胺構成之纖維材料進行染色及/或印刷上之用途。另一態樣係製造噴墨印刷油墨之方法及其於對由天然或合成聚醯胺構成之纖維材料進行印刷上之用途。
染色係根據習知方法實施,參見例如Ullmanns Encyklopdie der technischen Chemie(第4版,1982年,第22卷,第658-673頁)或M.Peter及H.K.Rouette之書Grundlagen der Textilveredlung(第13版,1989年,第535-556及566-574頁)中所述之染色方法。在浸染製程中溫度較佳為30至140℃,更佳為80至120℃且最佳溫度為80至100℃,且液體比介於3:1至40:1之間。
欲染色基材可為例如紗線、機織物、成圈針織物或地毯形式。甚至可能持久地於嬌嫩之基材上實施造型染色,該等基材實例係羔羊毛、喀什米爾羊毛、羊駝毛及馬海毛(mohair)。本發明染料尤其用於細丹尼爾(denier)纖維(微纖維)之染色。
本發明之染料及其鹽與習知酸性染料高度相容。因此,式(I)染料、其鹽或混合物可於印刷或染色製程中單獨使用,或者作為一種拼色組合染色或印刷組合物中之一組份,與其它相同類型酸性染料(亦即與具對等染色性質,例如牢度性及自染浴至基材上之上染率之酸性染料)一起使用。本發明之染料尤其可與某些具有合適發色團之其他染料一起使用。在拼色組合染色或印刷組合物中所存在染料之比例取決於欲獲得之色調。
如上所述式(I)之新型染料極適用於天然及合成聚醯胺(即羊毛、絲、及所有耐綸類型)之染色,其中於任一種上之染色皆具有高牢度,尤其具有良好耐光牢度及良好耐濕牢度(洗滌、鹼性汗漬)。式(I)之染料及其鹽具有高上染率。式(I)之染料及其鹽之提升能力同樣極為良好。突出品質係於確定基材上色光一致之染色。此外,在人造光下,所有染色皆具有固定的色調。而且,在蒸煮條件下之牢度良好。
該等新型染料一個突出優點為其不含金屬且提供極高水平之染色。
本發明之化合物可用作單一染料,或者,因其具有良好的相容性,可作為組合成份與其它具有相當染色性質(例如就常規牢度、上染率值等而言)之同類染料一起使用。所獲得之拼色組合染色具有與該單一染料染色類似之牢度。
本發明之式(I)染料亦可用作三原色染色或印刷中之紅色組份。三原色染色或印刷可利用所有常規及習知染色或印刷製程,例如連續製程、浸染製程、泡沫染色製程以及噴墨製程。
本發明方法中所用三原色染料混合物中單一染料組份之成份取決於期望之色調。舉例而言,褐色色調較佳使用20-40重量%的黃色組份、40-60重量%的本發明橙色或紅色組份及10-20重量%的藍色組份。
如上所述橙色組份可由單一組份組成,或由符合式(I)之不同橙色個別組份之混合物組成。較佳者係雙重及三重組合。
尤其較佳之藍色及/或黃色組份闡述於WO 2002/46318中。
在以下實例中,份數及百分比皆以重量計且溫度以攝氏度報告。
將29.1份3-[(乙基苯基胺基)甲基]苯磺酸懸浮於200份水中並藉由添加少量pH為7-7.5的氫氧化鈉溶液(約30%強度)使其溶解。然後將此溶液與雙重氮鹽溶液混合,該雙重氮鹽溶液係以常用方式自43.0份1,2-(4,4'-二胺基聯苯基)乙烷與50份(以體積計)4 N亞硝酸鈉溶液於0-5℃下製得。藉由計量添加15%碳酸鈉溶液將pH保持在7.0-7.5。偶合結束後,將所得下式之染料
利用氯化鈉鹽析、濾出並於50℃下在降低壓力下乾燥。在羊毛且具體而言在聚醯胺纖維上,其產生具有極好耐光牢度及耐濕牢度之橙色染色(λ(最大值)(λmax
)=482 nm)。
下表I及II包含可藉由類似於實例1中所闡述之方法使用相應起始原料製備之染料。該等染料在聚醯胺纖維及羊毛上提供具有極好耐光牢度及耐濕牢度之橙色染色。
染浴溫度為40℃,其由2000份水、1份弱陽離子活性勻染劑(其係以乙氧基化胺基丙基脂肪酸醯胺為主且其對染料具有親和力)、0.25份製備實例1之染料組成並用1-2份40%乙酸調節pH值至5,向其中加入100份耐綸-6織物。於40℃下保持10分鐘後,將該染浴以1℃/分鐘之速率加熱至98℃並然後使其於沸騰狀態下保持45-60分鐘。隨後使其在15分鐘內冷卻至70℃。自該染浴取出染色,用熱水且然後用冷水沖洗並乾燥。最終得到具有良好耐光牢度及耐濕牢度之橙色聚醯胺染色。
染浴溫度為40℃,其由2000份水、1份弱陽離子活性勻染劑(其係以乙氧基化胺基丙基脂肪酸醯胺為主且其對染料具有親和力)、0.3份製備實例1之染料組成並用1-2份40%乙酸調節pH值至5.5,向其中加入100份耐綸-6,6織物。於40℃下保持10分鐘後,將該染浴以1.5℃/分鐘之速率加熱至120℃並將其於此溫度下保持15-25分鐘。隨後將其在25分鐘內冷卻至70℃。自該染浴中取出染色,用熱水且然後用冷水沖洗並乾燥。最終得到具有良好均染性並具有良好的耐光牢度及耐濕牢度之橙色聚醯胺染色。
染浴溫度為40℃,其由4000份水、1份弱兩性勻染劑(其係以硫酸化乙氧基化脂肪酸醯胺為主且其對染料具有親和力)、0.4份製備實例1之染料組成並用1-2份40%乙酸調節pH值至5,向其中加入100份羊毛織物。於40℃下保持10分鐘後,將該染浴以1℃/分鐘的速率加熱至沸騰並然後於沸騰狀態下保持40-60分鐘。隨後將其於20分鐘內冷卻至70℃。自該染浴取出染色,用熱水且然後用冷水沖洗並乾燥。最終得到具有良好耐光牢度及耐濕牢度之橙色羊毛染色。
將100份機織耐綸-6材料用由以下成份組成的50℃染液軋染:40 份 製備實例1之染料,100 份 尿素,20 份 非離子增溶劑(以丁二醇為主),15-20 份 乙酸(以調節pH值至4),10 份 弱陽離子活性勻染劑(其係以乙氧基化胺基丙基脂肪酸醯胺為主且其對染料具有親和力),及810-815 份 水(以補足軋染液至1000份)。
將如此浸染之材料卷起並使其於85-98℃飽和蒸汽條件下在蒸汽室中保持3-6小時實施固色。然後將該染色用熱水及冷水沖洗並乾燥。最終得到橙色耐綸染色,其於整個物件中具有良好均染性及良好耐光牢度及耐濕牢度。
由耐綸-6構成且具有合成基織物的紡織割絨片狀材料用每1000份含如下組份的染液軋染:1 份製備實例1之染料4 份市售增稠劑(以角豆莢粉醚為主)2 份高碳烷基酚之非離子環氧乙烷加成物1 份60%乙酸。
然後,用每1000份含如下組份的漿料印刷:20 份市售烷氧基化脂肪烷基胺(替換產品)20 份市售增稠劑(以角豆莢粉醚為主)。
將印刷於100℃飽和蒸汽中固定6分鐘,沖洗並乾燥。最終得到有橙色及白色圖案之均勻著色覆蓋材料。
染浴溫度為40℃,其由2000份水、1份弱陽離子活性勻染劑(其係以乙氧基化胺胺丙基脂肪酸醯胺為主且對染料具有親和力)、0.2份實例1之染料、1.5份市售C.I.酸性黃236製劑(Nylosan Yellow F-L)及0.5份專利申請案WO 99/51681及EP 1066340 B1製備實例46之藍色染料組成:
專利申請案WO 99/51681及EP 1066340 B1之製備實例46,將其用1-2份40%乙酸調節pH值至5,向其中加入100份機織耐綸-6,6織物。於40℃下保持10分鐘後,染浴以1℃/分鐘之速率加熱至98℃並於沸騰狀態下保持45-60分鐘。隨後將其在15分鐘內冷卻至70℃。自該染浴取出染色,用熱水且然後用冷水沖洗並乾燥。最終得到具有良好耐光牢度及耐濕牢度之均勻灰色聚醯胺染色。
於55℃下將100份鉻鞣及以合成方式重鞣之刮毛-濕潤粒面皮革在300份水及2份製備實例1染料之浴液中染色30分鐘。添加4份60%亞硫酸化魚油之乳液後,將該皮革加脂45分鐘。然後將其用8.5%甲酸酸化並研磨10分鐘(該浴液之最終pH值為3.5-4.0)。然後將該皮革沖洗、滴乾並按常規修整。最終得到以均勻且清晰橙色調染色並具有良好牢度之皮革。
用染料2至140實施應用實例A-G亦可得到類似結果。
於60℃下將3份製備實例3之染料溶於82份脫礦質水及15份二乙二醇中。將其冷卻至室溫獲得橙色印刷油墨,其極適於在紙或聚醯胺及羊毛織物上噴墨印刷。
用染料1或2及4至140實施應用實例H亦可得到類似結果。
將由1000份水、80份經煆燒芒硝、1份硝基苯-3-磺酸鈉及1份實例79之染料組成之染浴在10分鐘內加熱至80℃。然後,添加100份絲光棉。隨後於80℃下染色5分鐘並然後在15分鐘內加熱至95℃。於95℃下10分鐘後,添加3份碳酸鈉,於95℃下20分鐘後再添加7份碳酸鈉且30分鐘後再額外添加10份碳酸鈉。隨後於95℃下持續染色60分鐘。然後將經染色材料自該染浴中取出並在流動脫礦質水中沖洗3分鐘。隨後洗滌兩次,每次皆在5000份沸騰脫礦質水中洗滌10分鐘,且隨後在60℃之流動脫礦質水中沖洗3分鐘並用冷自來水沖洗1分鐘。乾燥後獲得具有良好耐牢度之亮橙色棉花染色。
將0.2份製備實例1之染料溶於100份熱水中並將該溶液冷卻至室溫。將此溶液添加於100份在2000份水中在打漿機中打漿之化學漂白亞硫酸鹽漿中。混合15分鐘後,以常用方式用樹脂膠及硫酸鋁對原料上膠。由此原料製得之紙具有良好耐濕牢度之橙色色調。
用染料1至140實施應用實例I及J可獲得類似結果。
Claims (8)
- 一種通式(I)之化合物
- 如請求項1之化合物,其特徵在於R1 及R9 為未經取代無支鏈C1-6 烷基或未經取代具支鏈C3-6 烷基或經取代無支鏈C1-6 烷基或經取代具支鏈C3-6 烷基,R2 及R10 為芳基、或-(CH2 )p -芳基,其中p=1、2、3或4,R3 及R8 為氫、未經取代無支鏈C1-6 烷基或未經取代具支鏈C3-6 烷基或經取代無支鏈C1-6 烷基或經取代具支鏈C3-6 烷基或未經取代無支鏈C1-6 烷氧基或未經取代具支鏈C3-6 烷氧基或經取代無支鏈C1-6 烷氧基或經取代具支鏈C3-6 烷氧基,BR係式-A-B-A-之橋接基團,其中A為經取代苯基或經取代萘基或未經取代苯基或未經取代萘基,且B為橋接-[(CR6 R7 )-(CR6' R7' )m -(CR6" R7" )n -(CR6''' R7''' )o ]-,其中m、n及o具有1或0之意義,且R6 、R7 、R6' 、R7' 、R6" 、R7" 、R6''' 及R7''' 獨立為氫、未經取代無支鏈C1-6 烷基、經取代無支鏈C1-6 烷基、經取代具支鏈C3-6 烷基或未經取代具支鏈C3-6 烷基、未經取代無支鏈C1-6 烷氧基、未經取代或經取代苯基或R6 與R7 一起或R6' 與R7' 一起或R6" 與R7" 一起或R6''' 與R7''' 一起形成一個五或六員脂肪族環,或B為橋接碸,或B為橋接磺醯胺或B為橋接甲醯胺,或B為橋接且式(I)化合物具有1或2或3個磺酸基。
- 如請求項1或2之化合物,其特徵在於式(I)化合物具有2個磺酸基。
- 如請求項1或2之化合物,其特徵在於式(I)化合物之橋接基團BR具有結構(II-1)或(II-2)或(II-3)或(II-4)或(II-5):
- 一種製備如請求項1之式(I)化合物之方法,其特徵在於將下式(II)化合物的兩個胺官能團H2 N-BR-NH2 (II),重氮化並偶合至共2當量下式(IIIa)化合物及下式(IIIb)化合物上
- 一種以如請求項1之式(I)化合物於染色及/或印刷有機基材上之用途。
- 一種以如請求項1之式(I)化合物於染色及/或印刷羊毛、絲及合成聚醯胺上之用途。
- 一種以如請求項1之式(I)化合物於製備噴墨方法用之印刷油墨上之用途。
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EP2251383A1 (en) * | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Organic compounds |
EP2251325A1 (en) * | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Bisazo compounds |
ES2403068T3 (es) * | 2010-07-29 | 2013-05-13 | Clariant Finance (Bvi) Limited | Tintes ácidos |
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MX2008014473A (es) | 2008-11-27 |
EP2027213B1 (en) | 2012-11-21 |
US20090126128A1 (en) | 2009-05-21 |
JP2009538364A (ja) | 2009-11-05 |
KR101340101B1 (ko) | 2013-12-10 |
US20110203058A1 (en) | 2011-08-25 |
US8357210B2 (en) | 2013-01-22 |
CN101448901B (zh) | 2013-08-21 |
CA2646126A1 (en) | 2007-11-22 |
TW200804534A (en) | 2008-01-16 |
JP5341750B2 (ja) | 2013-11-13 |
PT2027213E (pt) | 2013-02-05 |
BRPI0711651B1 (pt) | 2017-02-21 |
WO2007131957A2 (en) | 2007-11-22 |
EP2027213A2 (en) | 2009-02-25 |
WO2007131957A3 (en) | 2008-02-07 |
KR20090010984A (ko) | 2009-01-30 |
AU2007251589A1 (en) | 2007-11-22 |
CN101448901A (zh) | 2009-06-03 |
ES2397184T3 (es) | 2013-03-05 |
BRPI0711651A2 (pt) | 2011-11-29 |
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