CN102782211A - 分散染料 - Google Patents
分散染料 Download PDFInfo
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- CN102782211A CN102782211A CN2010800613250A CN201080061325A CN102782211A CN 102782211 A CN102782211 A CN 102782211A CN 2010800613250 A CN2010800613250 A CN 2010800613250A CN 201080061325 A CN201080061325 A CN 201080061325A CN 102782211 A CN102782211 A CN 102782211A
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 14
- 229910006095 SO2F Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 77
- 239000000975 dye Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000987 azo dye Substances 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003906 humectant Substances 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 13
- 229920000728 polyester Polymers 0.000 abstract description 10
- 238000005406 washing Methods 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 description 15
- 230000008022 sublimation Effects 0.000 description 15
- 238000004043 dyeing Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229920002994 synthetic fiber Polymers 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000004758 synthetic textile Substances 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 238000010014 continuous dyeing Methods 0.000 description 3
- 238000010016 exhaust dyeing Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(C(CC*)=CCN=NC1=CC=SC(*)=CC1=*)N(*)* Chemical compound CCC(C(CC*)=CCN=NC1=CC=SC(*)=CC1=*)N(*)* 0.000 description 2
- ZBEPMOZEXLGCTF-UHFFFAOYSA-N O=C(C1CC1)N1CCCC(C1)NC1=NC(=CC=N1)N1C(CC#N)=CN=C1C1=CC2=C(OC=C2)C=C1 Chemical compound O=C(C1CC1)N1CCCC(C1)NC1=NC(=CC=N1)N1C(CC#N)=CN=C1C1=CC2=C(OC=C2)C=C1 ZBEPMOZEXLGCTF-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 150000003142 primary aromatic amines Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WJCVQGXSVFSDMW-UHFFFAOYSA-N C(#N)CC(C(=O)O)CN(C1=CC=CC=C1)CC.C(C)N(C1=CC=CC=C1)CCC(=O)OCC#N Chemical compound C(#N)CC(C(=O)O)CN(C1=CC=CC=C1)CC.C(C)N(C1=CC=CC=C1)CCC(=O)OCC#N WJCVQGXSVFSDMW-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WDENQIQQYWYTPO-IBGZPJMESA-N acalabrutinib Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C(=O)NC=2N=CC=CC=2)=C2N1C=CN=C2N WDENQIQQYWYTPO-IBGZPJMESA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
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- 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
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- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
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- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
- C09B29/0817—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR having N(-aliphatic residue-COOR)2 as substituents
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- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
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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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种通式(1)的分散染料，其中，X、Y和Z独立地为氢、卤素、氰基、硝基或SO2F；其中X、Y和Z的至少一个为SO2F。R1为氢、甲基、羟基或NHR4；R2为氢、氯或甲氧基；R3为氢、(C1-C4)烷基或-CH2(CH2)nCOOCH2CN；R5为氢、(C1-C4)烷基或-CH2(CH2)mCOOCH2CN；R4为-COCH3、-COC2H5、-SO2CH3或SO2C2H5；n和m独立地为0、1或2，附带条件为：-在Y和Z都为Cl时，R1不为甲基。-在R2为氢且R3和R4都为烷基时，R1选自NHSO2CH3或NHSO2C2H5。通式(1)的分散染料对聚酯和聚酯混纺物具有优异的耐洗性和耐光性。
Description
技术领域
本发明涉及一种新的分散染料及其应用。
背景技术
传统上，分散染料用于以通常的浸染染色、连续染色和印刷技术对合成纤维及其与其它纤维如纤维素、聚氨酯、尼龙和毛绒的混纺物进行染色。
印度专利申请2162/KOLNP/2009，其为WO2008/074719的印度相同申请且名称为“分散染料混合物”，公开了用于对合成纺织材料着色的偶氮分散染料与蒽醌或苯并二呋喃酮染料的混合物。所述专利着重于分散染料混合物以实现所需的牢度性能。
印度专利号IN190551(1700/DEL/94)，其为WO950200014的印度相同申请，涉及单偶氮染料、对合成纺织材料着色的方法、着色后的合成纺织物、用于塑料的本体染色的方法、着色后的塑料、特定的新偶氮染料以及包含偶氮染料的组合物。IN190551的分案申请号IN197577(935/DEL/2002)和IN196765(936/DEL/2002)也教导了用于制备偶氮染料化合物的方法。
最近，随着流行、时尚和市场需要的变化，混纺织物的消耗明显增加。这些新织物由使用细旦聚酯纤维或与聚氨酯、尼龙和毛绒的混纺纤维的微尺寸纤维制成。这些新着色织物的牢度性能在耐光性和升华牢度上变差，尤其是在用常规分散染料染色或印刷时的耐洗性变差。
为了克服用于合成纺织物的分散染料的耐光性和耐洗性的局限，本发明的发明人已开发了一系列具有优异的综合牢度性能，尤其是耐洗性的分散染料。
发明内容
本发明的一个目的在于提供偶氮分散染料。
本发明的另一目的在于提供对聚酯纤维具有优异的耐洗性的偶氮分散染料。
本发明的又一目的在于提供对合成纺织材料着色的方法。
根据本发明的一个方面，提供一种以下通式的分散染料，
其中，
X、Y和Z独立地为氢、卤素、氰基、硝基或SO2F；
其中X、Y和Z的至少一个为SO2F。
R1为氢、甲基、羟基或NHR4；
R2为氢、氯或甲氧基；
R3为氢、(C1-C4)烷基或-CH2(CH2)nCOOCH2CN；
R5为氢、(C1-C4)烷基或-CH2(CH2)mCOOCH2CN；
R4为-COCH3、-COC2H5、-SO2CH3或SO2C2H5；
n和m独立地为0、1或2。
附带条件为：
-在Y和Z都为Cl时，R1不为甲基。
-在R2为氢且R3和R5都为烷基时，R1选自NHSO2CH3或NHSO2C2H5。
在上述通式(1)中限定的分散染料对聚酯纤维具有优异的耐洗性和耐光性。
具体实施方式
偶氮分散染料通常通过芳族伯胺的重氮化作用并随后与合适的偶联组分偶联来制备。
本发明涉及分散染料和对纤维应用这些染料的方法。
上述分散染料用于以通常的浸染染色、连续染色和印刷技术对聚酯及其与其它纤维如纤维素、聚氨酯、尼龙和毛绒的混纺物进行染色。最近，着色织物的牢度性能由于使用细旦聚酯纤维或与聚氨酯、尼龙和毛绒的混纺纤维而在耐光性和升华牢度，尤其是耐洗性上变差。在染色和印刷领域中需要承受此应用的优异染料。
为了解决这些问题，本发明的发明人已设计了如通式(1)所示的具有优异的耐洗性的新偶氮分散染料。
其中，
X、Y和Z独立地为氢、卤素、氰基、硝基或SO2F；
其中X、Y和Z的至少一个为SO2F。
R1为氢、甲基、羟基或NHR4；
R2为氢、氯或甲氧基；
R3为氢、(C1-C4)烷基或-CH2(CH2)nCOOCH2CN；
R5为氢、(C1-C4)烷基或-CH2(CH2)mCOOCH2CN；
R4为-COCH3、-COC2H5、-SO2CH3或SO2C2H5；
n和m独立地为0、1或2。
附带条件为：
-在Y和Z都为Cl时，R1不为甲基。
-在R2为氢且R3和R5都为烷基时，R1选自NHSO2CH3或NHSO2C2H5。
在适宜的条件下，芳族伯胺能够成功地重氮化并与特别开发的偶联组分偶联以获得通式(1)的新分散染料。这些新分散染料具有优异的耐洗性和耐光性。
本发明的具体方面提供了一种组合物，包括本发明的分散染料和另外的常用于着色应用的至少一种其它成分如分散剂，以及可选择的表面活性剂或湿润剂。作为固体介质中的单一组分或混合物，该染料组合物通常包括总染料的10wt％至65wt％，优选20wt％至50wt％。
优选的分散剂为木质素磺酸盐类、萘磺酸/甲醛缩合物类和苯酚/甲酚/磺胺酸/甲醛缩合物类。湿润剂的优选实例为可磺化或磷化的烷基芳基乙氧基化物，且可存在的其它成分的典型实例为无机盐类、消泡剂如矿物油或壬醇、有机液体类和缓冲剂类。基于染料混合物的重量，分散剂可以80％至400％的量存在。基于染料混合物的重量，湿润剂可以0.1％至20％的量使用。
本发明的分散染料或分散染料的混合物在水介质中通过利用玻璃珠或沙子的适宜分散剂研磨。上述组合物可进一步具有分散剂、填料和其它表面活性剂，并可通过诸如喷雾干燥的技术进行干燥以提供包含染料的15wt％至65wt％的固体组合物。
在对纤维材料染色时，在水中用分散剂以普通方法研磨染料，并将制得的染料以液体形式或液体喷雾干燥后的粉末形式用于染色或印刷。将每种制得的染料以本发明的单一、或者两种或更多种的混合物的形式用于染色和印刷。
在浸染染色时，通过高温染色、载体染色和连续染色以优异的牢度对聚酯纤维、组合纤维和混纺纤维进行染色。通式(1)的染料可单独或作为通式(1)的衍生物的混合物用于染色和印刷。
在印刷时，通过直接印刷或拔染以优异的牢度加工聚酯纤维、纺织材料。
将参照以下实施例详细说明本发明的实施方式，其中，除非另作说明，否则份数为重量份。
实施例：
本发明具体解释如下，但本发明不限于这些实施例。
实施例-1：
结构式(2)
用以下方法合成实施例1的结构式(2)。
在0～5℃将40％的亚硝酰硫酸3ml加入到2：5-二氯代氟代磺酰苯胺2.0g、乙酸和丙酸(86∶14，25ml)的混合物中，并在低于5℃下搅拌2小时。将偶联剂N-乙基-N-氰基甲氧基羰基乙基苯胺(3-(乙基(苯基)氨基)丙酸氰基甲酯)2.1g溶解在甲醇100ml中，并在0～5℃将上述合成的重氮化的溶液加入到该偶联剂溶液中。在低于5℃下搅拌该反应物料1小时，过滤掉结晶固体并用水洗涤。
得到7.0g的50％的湿滤饼。产率为80％。实施例1的染料在丙酮中的λmax为515nm。
然后将2.0g制得的湿压滤饼用2.0g的萘磺酸-甲醛缩合物、50g水和500g的玻璃珠(平均直径为0.8mm)研磨24小时，研磨后，过滤物料以分离玻璃珠。
在100ml水中加入2.0g制得的所得液体，并用乙酸保持pH4，并将10g的聚酯片加入到该染料浴中以进行浸染染色。
将该染料浴加热至135℃并保持40分钟。在适当地漂洗、洗涤并干燥后，染色后的材料提供具有优异的耐洗性、耐光性和升华牢度的红宝石深色。
染色织物的牢度性能由以下测试方法评价。
耐洗性依照测试方法AATCC 61 2A，耐光性依照测试方法ISO 105 B02，且升华测试在180℃下30秒和在210℃下30秒。
实施例-2
用与实施例-1中描述的相同方法合成通式(3)的染料以得到表中描述的以下染料：
| 实施例 | R1 | R2 | R3 | R4 | m | λmax(nm) |
| 2-1 | H | H | C3H7 | --- | 1 | 517 |
| 2-2 | H | H | C2H5 | --- | 2 | 522 |
| 2-3 | NHR4 | H | C2H5 | SO2CH3 | 1 | 530 |
| 2-4 | NHR4 | H | C2H5 | COCH3 | 1 | 537 |
| 2-5 | OH | H | C4H9(n) | --- | 1 | 520 |
这些染料显示了优异的耐洗性、耐光性和升华牢度。
实施例-3
用与实施例-1中描述的相同方法合成通式(4)的染料以得到表中描述的以下染料：
| 实施例 | X | Y | R4 | R3和R5 | λmax(nm) |
| 3-1 | Cl | Cl | C2H5 | C2H5 | 537 |
| 3-2 | Cl | Cl | CH3 | C2H5 | 537 |
| 3-3 | NO2 | H | CH3 | C2H5 | 545 |
| 3-4 | NO2 | Cl | CH3 | C2H5 | 551 |
| 3-5 | Cl | Cl | CH3 | C2H4OCH3 | 527 |
| 3-6 | Cl | Cl | CH3 | C4H9(n) | 539 |
这些染料提供了非常好的明亮色，并显示了优异的耐洗性、耐光性和升华牢度。
实施例-4：
用与实施例-1中描述的相同方法合成通式(5)的染料以得到表中描述的以下染料：
| 实施例 | Y | Z | R1 | R2 | R3 | R4 | m | λmax(nm) |
| 4-1 | NO2 | H | H | H | C2H5 | --- | 1 | 520 |
| 4-2 | NO2 | H | H | H | C2H5 | --- | 0 | 511 |
| 4-3 | NO2 | H | NHR4 | H | C2H5 | COCH3 | 1 | 532 |
| 4-4 | Cl | Cl | H | H | C2H5 | --- | 0 | 418 |
| 4-5 | Cl | Cl | H | H | CH2COOCH2CN | --- | 1 | 417 |
| 4-6 | CN | H | H | H | C2H5 | --- | 1 | 543 |
这些染料显示了优异的耐洗性、耐光性和升华牢度。
实施例-5：
用与实施例-1中描述的相同方法合成通式(6)的染料以得到表中描述的以下染料：
| 实施例 | X | Z | R1 | R2 | R3 | R4 | m | λmax(nm) |
| 5-1 | NO2 | H | H | H | C2H5 | --- | 1 | 523 |
| 5-2 | SO2F | H | H | H | C2H5 | --- | 1 | 511 |
| 5-3 | NO2 | H | NHR4 | H | CH2COOCH2CN | COCH3 | 0 | 546 |
| 5-4 | NO2 | Cl | NHR4 | H | C2H5 | SO2CH3 | 1 | 570 |
| 5-5 | NO2 | Cl | NHR4 | OCH3 | C2H5 | COCH3 | 1 | 602 |
这些染料显示了优异的耐洗性、耐光性和升华牢度。
实施例-6：
用与实施例-1中描述的相同方法合成通式(7)的染料以得到表中描述的以下染料：
| 实施例 | Y | Z | R1 | R2 | R3 | R4 | - | λmax(nm) |
| 6-1 | Cl | Cl | H | H | C2H5 | --- | 1 | 513 |
| 6-2 | Cl | Cl | OH | H | C2H5 | --- | 1 | 535 |
| 6-3 | NO2 | H | H | H | CH2COOCH2CN | --- | 1 | 519 |
| 6-4 | Cl | Cl | NHR4 | H | C2H4COOCH2CN | COCH3 | 1 | 526 |
| 6-5 | Cl | H | CH3 | H | C2H5 | --- | 1 | 516 |
这些染料显示了优异的耐洗性、耐光性和升华牢度。
对比例-1：
将WO95/20014的表-1中记为实施例-37的以下染料与本专利中记为染料实施例-1的染料比较耐光性、耐洗性和升华牢度如下。
耐洗性依照测试方法AATCC 61 2A，耐光性依照测试方法ISO 105 B02，且升华测试在180℃下30秒和在210℃下30秒
本专利的实施例-1的染料和WO95/20014的染料-37为非常相似的化学制品，区别仅在于氨基上的乙基和C2H4COOCH2CN，但特性区别非常大，尤其是在耐洗性以及升华牢度和耐光性上。该对比例对逻辑法提供确认，引入两个C2H4COOCH2CN取代基代替WO95/20014中的仅一个C2H4COOCH2CN取代基以改善耐洗性。引入两个C2H4COOCH2CN取代基提供更优异的耐洗性，同样也使升华牢度和耐光性得到改善。
对比例2
在另一个提高WO95/20014的对比染料实施例-37的耐光性能的方法中，本专利的发明人已在偶联组分的3-(间)位上引入-NHSO2CH3或-NHSO2C2H5取代基，且以下的对比数据清楚地显示了通过预期改变而实现的优异性能。
耐洗性依照测试方法AATCC 61 2A，耐光性依照测试方法ISO 105 B02，且升华测试在180℃下30秒和在210℃下30秒
本专利的实施例-3-2的染料和WO95/20014的染料-37为非常相似的化学制品，区别仅在于偶联组分上-NHSO2CH3之间的区别。但特性区别非常大，尤其是在耐洗性以及升华牢度和耐光性上。该对比例进一步对采用的逻辑法提供确认，通过引入-NHSO2CH3取代基改善WO95/20014的对比染料-37的耐光性能。
尽管已结合具体实施方式说明了本发明，但明显，本领域技术人员鉴于上述说明明显可进行多种替换、修改和变更。因此，意在包括在所附权利要求的精神和范围内解释的所有此类替换、修改和变更。
权利要求书(按照条约第19条的修改)
1.一种通式(1)的新偶氮分散染料，
其中，
X、Y和Z独立地为氢、卤素、氰基、硝基或SO2F；
其中X、Y和Z的至少一个为SO2F；
R1为氢、甲基、羟基或NHR4；
R2为氢、氯或甲氧基；
R3为氢、(C1-C4)烷基或-CH2(CH2)mCOOCH2CN；
R4为-COCH3、-COC2H5、-SO2CH3或SO2C2H5；
n和m独立地为0、1或2，
附带条件为：
在Y和Z都为Cl时，R1不为甲基。
2.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为式(2)的化合物：
3.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(3)的化合物：
其中
| R1 | R2 | R3 | R4 | n |
| H | H | C3H7 | --- | 1 |
| H | H | C2H5 | --- | 2 |
| NHR4 | H | C2H5 | SO2CH3 | 1 |
| NHR4 | H | C2H5 | COCH3 | 1 |
| OH | H | C4H9(n) | --- | 1 |
。
4.一种通式(4)的新偶氮分散染料，
其中，
| X | Y | R3 | R5 | R4 |
| Cl | Cl | C2H5 | C2H5 | CH3 |
| Cl | Cl | C2H5 | C2H5 | C2H5 |
| NO2 | H | CH3 | C2H5 | CH3 |
| NO2 | H | CH3 | C2H5 | C2H5 |
| NO2 | Cl | CH3 | C2H5 | CH3 |
| NO2 | Cl | CH3 | C2H5 | C2H5 |
| Cl | Cl | CH3 | C2H4OCH3 | CH3 |
| Cl | Cl | CH3 | C2H4OCH3 | C2H5 |
| Cl | Cl | CH3 | C4H9(n) | CH3 |
| Cl | Cl | CH3 | C4H9(n) | C2H5 |
。
5.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(5)的化合物：
其中，
| Y | Z | R1 | R2 | R3 | R4 | n |
| NO2 | H | H | H | C2H5 | --- | 1 |
| NO2 | H | H | H | C2H5 | --- | 0 |
| NO2 | H | NHR4 | H | C2H5 | COCH3 | 1 |
| Cl | Cl | H | H | C2H5 | --- | 0 |
| Cl | Cl | H | H | CH2COOCH2CN | --- | 1 |
| CN | H | H | H | C2H5 | --- | 1 |
。
6.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(6)的化合物：
其中，
| X | Z | R1 | R2 | R3 | R4 | n |
| NO2 | H | H | H | C2H5 | --- | 1 |
| SO2F | H | H | H | C2H5 | --- | 1 |
| NO2 | H | NHR4 | H | CH2COOCH2CN | COCH3 | 0 |
| NO2 | Cl | NHR4 | H | C2H5 | SO2CH3 | 1 |
| NO2 | Cl | NHR4 | OCH3 | C2H5 | COCH3 | 1 |
。
7.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(7)的化合物：
其中，
| Y | Z | R1 | R2 | R3 | R4 | n |
| Cl | Cl | H | H | C2H5 | --- | 1 |
| Cl | Cl | OH | H | C2H5 | --- | 1 |
| NO2 | H | H | H | CH2COOCH2CN | --- | 1 |
| Cl | Cl | NHR4 | H | C2H4COOCH2CN | COCH3 | 1 |
| Cl | H | CH3 | H | C2H5 | --- | 1 |
。
8.一种根据前述任一项权利要求的分散染料组合物，包含：通式(1)的偶氮染料或其混合物；在染料混合物的80wt％至400wt％的范围内的分散剂；以及可选的在所述染料混合物的0.1wt％至20wt％的范围内的湿润剂。
9.一种根据前述任一项权利要求所述的作为单一组分、或者两种或更多种染料的组合的染色材料。
Claims (9)
1.一种通式(1)的新偶氮分散染料，
其中，
X、Y和Z独立地为氢、卤素、氰基、硝基或SO2F；
其中X、Y和Z的至少一个为SO2F；
R1为氢、甲基、羟基或NHR4；
R2为氢、氯或甲氧基；
R3为氢、(C1-C4)烷基或-CH2(CH2)nCOOCH2CN；
R5为氢、(C1-C4)烷基或-CH2(CH2)mCOOCH2CN；
R4为-COCH3、-COC2H5、-SO2CH3或SO2C2H5；
n和m独立地为0、1或2，
附带条件为：
-在Y和Z都为Cl时，R1不为甲基，
-在R2为氢且R3和R4都为烷基时，R1选自NHSO2CH3或NHSO2C2H5。
2.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为式(2)的化合物：
3.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(3)的化合物：
其中
。
4.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(4)的化合物：
其中，
。
5.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(5)的化合物：
其中，
。
6.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(6)的化合物：
其中，
7.根据权利要求1所述的新偶氮分散染料，其中，所述通式(1)的化合物为通式(7)的化合物：
其中，
。
8.一种根据前述任一项权利要求的分散染料组合物，包含：通式(1)的偶氮染料或其混合物；在染料混合物的80wt％至400wt％的范围内的分散剂；以及可选的在所述染料混合物的0.1wt％至20wt％的范围内的湿润剂。
9.一种根据前述任一项权利要求所述的作为单一组分、或者两种或更多种染料的组合的染色材料。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2980/MUM/2009 | 2009-12-23 | ||
| IN2980MU2009 | 2009-12-23 | ||
| PCT/IN2010/000851 WO2011077462A2 (en) | 2009-12-23 | 2010-12-23 | Disperse dyes |
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| Publication Number | Publication Date |
|---|---|
| CN102782211A true CN102782211A (zh) | 2012-11-14 |
| CN102782211B CN102782211B (zh) | 2016-01-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201080061325.0A Expired - Fee Related CN102782211B (zh) | 2009-12-23 | 2010-12-23 | 分散染料 |
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| Country | Link |
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| US (1) | US8506652B2 (zh) |
| EP (1) | EP2516728B1 (zh) |
| JP (1) | JP2013515811A (zh) |
| KR (1) | KR101801993B1 (zh) |
| CN (1) | CN102782211B (zh) |
| AR (1) | AR081120A1 (zh) |
| CL (1) | CL2012001716A1 (zh) |
| CO (1) | CO6571910A2 (zh) |
| EC (1) | ECSP12012059A (zh) |
| ES (1) | ES2812502T3 (zh) |
| GT (1) | GT201200211A (zh) |
| MX (1) | MX2012007258A (zh) |
| MY (1) | MY159806A (zh) |
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| WO (1) | WO2011077462A2 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106280535A (zh) * | 2016-08-08 | 2017-01-04 | 绍兴文理学院 | 一种高水洗牢度分散染料及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104059377B (zh) * | 2014-05-29 | 2015-11-18 | 杭州吉华江东化工有限公司 | 一种偶氮分散染料的合成方法 |
| KR101889402B1 (ko) * | 2016-04-04 | 2018-08-17 | 대영산업 주식회사 | 세탁견뢰도 및 승화견뢰도가 우수하고, 스판덱스 황변현상이 없는 분산염료 조성물 |
| CN106084874B (zh) * | 2016-06-14 | 2017-07-18 | 绍兴文理学院 | 一种分散染料及其制备方法与应用 |
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| CN1099776A (zh) * | 1993-05-06 | 1995-03-08 | 希巴-盖吉股份公司 | 偶氮染料 |
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| WO1997027247A1 (en) * | 1996-01-26 | 1997-07-31 | Basf Aktiengesellschaft | Monoazo dyes containing a fluorosulphonyl group and use thereof |
| GB2312433A (en) * | 1996-04-25 | 1997-10-29 | Zeneca Ltd | Ink and toner compositions based on a derivative of 3-alkyl-N-alkyl-N-(alkoxycarbonylalkyl)-4-([2,5-dichloro-4-fluorosulphonylphenyl]azo)aniline |
| CN1288916A (zh) * | 1999-09-20 | 2001-03-28 | 西巴特殊化学品控股有限公司 | 偶氮染料,它们的制备方法及其在疏水性纤维材料染色和印染中的应用 |
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| GB764308A (en) * | 1952-12-24 | 1956-12-28 | Sandoz Ltd | Improvements in or relating to monoazo dyestuffs |
| DE953104C (de) * | 1952-12-24 | 1956-11-29 | Sandoz Ag | Verfahren zur Herstellung von Monoazofarbstoffen |
| GB909843A (en) * | 1959-02-10 | 1962-11-07 | Ici Ltd | New monoazo dyestuffs containing ester groups |
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| GB0625624D0 (en) * | 2006-12-21 | 2007-01-31 | Dystar Textilfarben Gmbh & Co | Disperse dye mixtures |
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- 2010-12-23 US US13/519,023 patent/US8506652B2/en active Active
- 2010-12-23 JP JP2012545526A patent/JP2013515811A/ja active Pending
- 2010-12-23 MX MX2012007258A patent/MX2012007258A/es active IP Right Grant
- 2010-12-23 EP EP10824270.2A patent/EP2516728B1/en active Active
- 2010-12-23 KR KR1020127019044A patent/KR101801993B1/ko active IP Right Grant
- 2010-12-23 TW TW099145555A patent/TWI509028B/zh not_active IP Right Cessation
- 2010-12-23 CN CN201080061325.0A patent/CN102782211B/zh not_active Expired - Fee Related
- 2010-12-23 MY MYPI2012002894A patent/MY159806A/en unknown
- 2010-12-23 WO PCT/IN2010/000851 patent/WO2011077462A2/en active Application Filing
- 2010-12-23 ES ES10824270T patent/ES2812502T3/es active Active
- 2010-12-23 AR ARP100104937A patent/AR081120A1/es unknown
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- 2012-06-22 CL CL2012001716A patent/CL2012001716A1/es unknown
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Patent Citations (5)
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| CN1099776A (zh) * | 1993-05-06 | 1995-03-08 | 希巴-盖吉股份公司 | 偶氮染料 |
| WO1995020014A1 (en) * | 1994-01-19 | 1995-07-27 | Zeneca Limited | Monoazo dyes containing a fluorosulphonyl group and use thereof |
| WO1997027247A1 (en) * | 1996-01-26 | 1997-07-31 | Basf Aktiengesellschaft | Monoazo dyes containing a fluorosulphonyl group and use thereof |
| GB2312433A (en) * | 1996-04-25 | 1997-10-29 | Zeneca Ltd | Ink and toner compositions based on a derivative of 3-alkyl-N-alkyl-N-(alkoxycarbonylalkyl)-4-([2,5-dichloro-4-fluorosulphonylphenyl]azo)aniline |
| CN1288916A (zh) * | 1999-09-20 | 2001-03-28 | 西巴特殊化学品控股有限公司 | 偶氮染料,它们的制备方法及其在疏水性纤维材料染色和印染中的应用 |
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Also Published As
| Publication number | Publication date |
|---|---|
| GT201200211A (es) | 2014-11-04 |
| EP2516728A2 (en) | 2012-10-31 |
| CL2012001716A1 (es) | 2013-01-11 |
| WO2011077462A4 (en) | 2011-11-10 |
| KR101801993B1 (ko) | 2017-11-27 |
| US20130117947A1 (en) | 2013-05-16 |
| CO6571910A2 (es) | 2012-11-30 |
| MX2012007258A (es) | 2012-10-03 |
| JP2013515811A (ja) | 2013-05-09 |
| KR20120106841A (ko) | 2012-09-26 |
| WO2011077462A2 (en) | 2011-06-30 |
| WO2011077462A3 (en) | 2011-08-18 |
| TW201125929A (en) | 2011-08-01 |
| EP2516728B1 (en) | 2020-05-27 |
| US8506652B2 (en) | 2013-08-13 |
| MY159806A (en) | 2017-02-15 |
| ES2812502T3 (es) | 2021-03-17 |
| ECSP12012059A (es) | 2012-12-28 |
| AR081120A1 (es) | 2012-06-27 |
| TWI509028B (zh) | 2015-11-21 |
| CN102782211B (zh) | 2016-01-20 |
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