CN101528856A - 分散偶氮染料 - Google Patents
分散偶氮染料 Download PDFInfo
- Publication number
- CN101528856A CN101528856A CNA2007800390890A CN200780039089A CN101528856A CN 101528856 A CN101528856 A CN 101528856A CN A2007800390890 A CNA2007800390890 A CN A2007800390890A CN 200780039089 A CN200780039089 A CN 200780039089A CN 101528856 A CN101528856 A CN 101528856A
- Authority
- CN
- China
- Prior art keywords
- methyl
- hydrogen
- amino
- nitroaniline
- formula
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 60
- 239000000460 chlorine Substances 0.000 claims description 56
- 239000000975 dye Substances 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 19
- 238000006193 diazotization reaction Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- -1 fluorosulfonyl Chemical group 0.000 claims description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 238000007639 printing Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- JIASUGKVEFLKQN-UHFFFAOYSA-N 5-nitro-1,2-benzothiazol-7-amine Chemical compound NC1=CC([N+]([O-])=O)=CC2=C1SN=C2 JIASUGKVEFLKQN-UHFFFAOYSA-N 0.000 claims description 8
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 claims description 7
- OQYHBXHZAXVUKW-UHFFFAOYSA-N S1C=NC=C1.NC1=CC(=CC=C1)[N+](=O)[O-] Chemical compound S1C=NC=C1.NC1=CC(=CC=C1)[N+](=O)[O-] OQYHBXHZAXVUKW-UHFFFAOYSA-N 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 7
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- FVNSRFMQXKMHTQ-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) thiocyanate Chemical compound C1=C(SC#N)C=C2SC(N)=NC2=C1 FVNSRFMQXKMHTQ-UHFFFAOYSA-N 0.000 claims description 5
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 claims description 5
- IICFGCMPQMPNRU-UHFFFAOYSA-N 2-amino-5-nitrothiophene-3-carboxylic acid Chemical compound NC=1SC([N+]([O-])=O)=CC=1C(O)=O IICFGCMPQMPNRU-UHFFFAOYSA-N 0.000 claims description 5
- VLMRGLCBIFWPGL-UHFFFAOYSA-N 2-chloro-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(Cl)=C1 VLMRGLCBIFWPGL-UHFFFAOYSA-N 0.000 claims description 5
- ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229960005081 diclofenamide Drugs 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 239000004758 synthetic textile Substances 0.000 claims description 2
- 239000000976 ink Substances 0.000 abstract 1
- 238000007641 inkjet printing Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000006185 dispersion Substances 0.000 description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- 235000019260 propionic acid Nutrition 0.000 description 9
- 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 9
- 238000001914 filtration Methods 0.000 description 8
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002932 luster Substances 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- JACCLQAUXMZURT-UHFFFAOYSA-N 3-(n-ethylanilino)propanoic acid Chemical compound OC(=O)CCN(CC)C1=CC=CC=C1 JACCLQAUXMZURT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- DZRZHFOFVWAKGT-UHFFFAOYSA-N 3,5-dinitrothiophen-2-amine Chemical compound NC=1SC([N+]([O-])=O)=CC=1[N+]([O-])=O DZRZHFOFVWAKGT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WEPOCZPVIPDYKZ-UHFFFAOYSA-N C(C)(=O)OC=C.C(C)N(CC(C(=O)O)C)C1=CC=CC=C1 Chemical compound C(C)(=O)OC=C.C(C)N(CC(C(=O)O)C)C1=CC=CC=C1 WEPOCZPVIPDYKZ-UHFFFAOYSA-N 0.000 description 1
- DVEDDJLSVKOPSJ-UHFFFAOYSA-N CCN(CCC(=O)O)C1=CC=CC(=C1)CN Chemical compound CCN(CCC(=O)O)C1=CC=CC(=C1)CN DVEDDJLSVKOPSJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000628997 Flos Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- FYONQYLEJJYXJN-UHFFFAOYSA-N N(=O)O.C[Na] Chemical compound N(=O)O.C[Na] FYONQYLEJJYXJN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005112 continuous flow technique Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
-
- 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
- C09B29/0811—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
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
-
- 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
-
- 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
-
- 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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Abstract
本发明涉及式(I)的染料、其制备方法、其用途及含有该染料的喷墨印花用油墨，式(I)中D、R1至R5、m及n如权利要求1中定义。
Description
技术领域
本发明涉及分散染料的领域。
背景技术
含有不饱和醇的酯基的分散偶氮染料可自文献中得知。特别地，在偶联成分中含有烯丙酯基团的分散偶氮染料已众所周知，例如描述于US5,428,138、US 5,639,282及US 2004/0143108 A1中。
令人惊讶地，本发明的发明人发现如果使用如下文定义的在偶联成分含有乙烯酯基团的染料，则可获得与疏水性纤维用标准染料相比具有改善的耐洗性的在聚酯上的染色。
发明内容
本发明涉及式(I)的染料
其中
D为重氮成分；
R1为氢、(C1-C4)烷基、羟基、-NHCOR6或-NHSO2R6；
R2为氢、卤素或(C1-C4)烷氧基；
R3为氢或甲基；
R4为氢，(C1-C6)烷基，取代的(C1-C6)烷基，被选自-O-、-S-及-NR7的1、2或3个杂原子中断的(C2-C6)烷基，被选自-O-、-S-及-NR7的1、2或3个杂原子中断的取代的(C2-C6)烷基，(C2-C6)烯基，取代的(C2-C6)烯基，苄基，或苯乙基；
R5为氢或甲基；
R6为(C1-C4)烷基、苯基或取代的苯基；
R7为(C1-C4)烷基、苯基或取代的苯基；
m为0、1或2；及
n为0或1。
重氮成分D可以为所有用于制备分散染料的重氮成分。这类偶联成分描述于文献中，且为本领域的技术人员所周知。
优选的重氮成分D具有式(IIa)
其中
G1为氢、卤素、氰基或硝基；
G2为氢、卤素或硝基；
G3为氢、卤素、甲磺酰基、氟磺酰基或硝基；及
G4为氢、卤素、三氟甲基、氰基或硝基；
或者D具有式(IIb)
其中
G5为氢或卤素；及
G6为氢、卤素、硝基、-SO2CH3或-SCN；
或者D具有式(IIc)
其中
G7为氢或卤素；
或者D具有式(IId)
其中
G8为硝基、氰基、-CHO或式(IIe)的基团
其中G11及G12独立地为氢、卤素、硝基或氰基；
G9为氢或卤素；及
G10为硝基、氰基、-COCH3或-COO-G13；其中G13为C1-C4烷基；
或者D具有式(IIf)
D的特别优选的实例衍生自下列胺：3，4-二氯苯胺、2-三氟甲基-4-硝基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2-氯-4-硝基苯胺、4-氯-2-硝基苯胺、2-溴-4-硝基苯胺、2-氯-4-甲磺酰基苯胺、2，6-二氯-4-硝基苯胺、2，6-二溴-4-硝基苯胺、2-氯-6-溴-4-硝基苯胺、2，5-二氯-4-硝基苯胺、2-氰基-4-硝基苯胺、2-氰基-6-氯-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2，4-二硝基苯胺、2-氯-4，6-二硝基苯胺、2-溴-4，6-二硝基苯胺、2-氨基-5-硝基噻唑、2-氨基-3，5-二硝基噻吩、2-氨基-5-硝基噻吩-3-羧酸乙酯、2-氨基-3-氰基-4-氯-5-甲酰基噻吩、2-氨基-5-(4-硝基苯基偶氮基)-噻吩-3-甲腈、7-氨基-5-硝基苯并异噻唑、2-氨基-6-硝基苯并噻唑、2-氨基-6-甲磺酰基苯并噻唑、2-氨基-6-硫氰酸根合苯并噻唑及2-氨基-5，6/6，7-二氯苯并噻唑。
在本说明书的定义中，烷基可以为直链或支链，优选地为甲基、乙基、正丙基、异丙基或正丁基。另外地，高达6个碳原子的烷基还可以为戊基或己基。相同逻辑也可适用在烷氧基及烯基上，烷氧基优选地为甲氧基、乙氧基或丙氧基，烯基优选地为乙烯基及烯丙基。
被选自-O-、-S-及-NR7的1、2或3个杂原子中断的(C2-C6)烷基的实例，为-CH2-O-CH2-、-(CH2)2-O-(CH2)2-、-CH2-S-CH2-、-(CH2)2-S-(CH2)2-、-CH2-NR7’-CH2-或-(CH2)2-NR7’-(CH2)2-，其中R7’为氢或甲基。
烷基、被中断的烷基、或烯基的取代基优选地为羟基、氰基、卤素、-COOH、-COOR8、-OC(O)R8、氨基、-NHC(O)R8及-NHSO2R8，其中R8为(C1-C4)烷基、苯基或取代的苯基。
取代的苯基带有1、2或3个取代基。这类取代基的实例为(C1-C6)烷基、(C1-C6)烷氧基、卤素、氰基及硝基。
卤素优选地为氟、氯或溴，其中在G1、G2、G3、G4、G5、G6、G7、G9、G11及G12的情况中卤素特别优选地为氯或溴。
在式(I)的优选染料中
R1为氢、甲基或-NHCOCH3；
R2为氢、氯、甲氧基或乙氧基；
R3为氢或甲基；
R4为氢、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、苄基、-CH2-O-CH2-或-(CH2)2-O-(CH2)2-；
R5为氢或甲基；
m为0、1或2；
n为0或1；及
D如上面给出的那样所定义或优选地具有式(IIa)至(IIf)的含义中的一种。
在式(I)的特别优选的染料中
R1为氢、甲基或-NHCOCH3；
R2为氢、氯、甲氧基或乙氧基；
R3为氢或甲基；
R4为氢、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、苄基、-CH2-O-CH2-或-(CH2)2-O-(CH2)2-；
R5为氢或甲基；
m为0、1或2；
n为0或1；及
D衍生自3，4-二氯苯胺、2-三氟甲基-4-硝基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2-氯-4-硝基苯胺、4-氯-2-硝基苯胺、2-溴-4-硝基苯胺、2-氯-4-甲磺酰基苯胺、2，6-二氯-4-硝基苯胺、2，6-二溴-4-硝基苯胺、2-氯-6-溴-4-硝基苯胺、2，5-二氯-4-硝基苯胺、2-氰基-4-硝基苯胺、2-氰基-6-氯-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2，4-二硝基苯胺、2-氯-4，6-二硝基苯胺、2-溴-4，6-二硝基苯胺、2-氨基-5-硝基噻唑、2-氨基-3，5-二硝基噻吩、2-氨基-5-硝基噻吩-3-羧酸乙酯、2-氨基-3-氰基-4-氯-5-甲酰基噻吩、2-氨基-5-(4-硝基苯基偶氮基)-噻吩-3-甲腈、7-氨基-5-硝基苯并异噻唑、2-氨基-6-硝基苯并噻唑、2-氨基-6-甲磺酰基苯并噻唑、2-氨基-6-硫氰酸根合苯并噻唑或2-氨基-6，7-二氯苯并噻唑。
式(I)的更特别优选的染料对应于式(Ia)
其中
G1为氢、氯、溴、氰基或硝基；
G2为氢、氯或硝基；
G3为氢、氯、硝基或甲磺酰基；
G4为氢、氯、溴、三氟甲基、氰基或硝基；
R1为氢、甲基或-NHCOCH3；
R2为氢或甲氧基；及
R4为氢、乙基、丁基或苄基。
式(I)的更特别优选的染料对应于式(Ib)
其中
G5为氢或氯；
G6为氯、硝基、-SO2CH3或-SCN；
R1为氢或甲基；及
R4为乙基或苄基。
式(I)的更特别优选的染料对应于式(Ic)
其中
R1为氢或甲基；及
R4为乙基或苄基。
式(I)的更特别优选的染料对应于式(Id)
其中
G8为硝基、-CHO或-N＝N-C6H4-p-NO2；
G9为氢或氯；
G10为硝基、氰基或-COOC2H5；
R1为氢或甲基；及
R4为乙基或苄基。
式(I)的更特别优选的染料对应于式(Ie)
其中
R1为氢或甲基；及
D具有式(IIa)至(IIf)的含义中的一种，且优选地衍生自3，4-二氯苯胺、2-三氟甲基-4-硝基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2-氯-4-硝基苯胺、4-氯-2-硝基苯胺、2-溴-4-硝基苯胺、2-氯-4-甲磺酰基苯胺、2，6-二氯-4-硝基苯胺、2，6-二溴-4-硝基苯胺、2-氯-6-溴-4-硝基苯胺、2，5-二氯-4-硝基苯胺、2-氰基-4-硝基苯胺、2-氰基-6-氯-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2，4-二硝基苯胺、2-氯-4，6-二硝基苯胺、2-溴-4，6-二硝基苯胺、2-氨基-5-硝基噻唑、2-氨基-3，5-二硝基噻吩、2-氨基-5-硝基噻吩-3-羧酸乙酯、2-氨基-3-氰基-4-氯-5-甲酰基噻吩、2-氨基-5-(4-硝基苯基偶氮基)-噻吩-3-甲腈、7-氨基-5-硝基苯并异噻唑、2-氨基-6-硝基苯并噻唑、2-氨基-6-甲磺酰基苯并噻唑、2-氨基-6-硫氰酸根合苯并噻唑或2-氨基-6，7-二氯苯并噻唑，而特别优选地衍生自2-氰基-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2-氨基-6-硝基苯并噻唑或7-氨基-5-硝基苯并异噻唑。
式(I)的更特别优选的染料对应于式(If)
其中
R1为氢或甲基；
R3为氢或甲基；
R5为氢或甲基；及
D具有式(IIa)至(IIf)的含义中的一种，且优选地衍生自3，4-二氯苯胺、2-三氟甲基-4-硝基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2-氯-4-硝基苯胺、4-氯-2-硝基苯胺、2-溴-4-硝基苯胺、2-氯-4-甲磺酰基苯胺、2，6-二氯-4-硝基苯胺、2，6-二溴-4-硝基苯胺、2-氯-6-溴-4-硝基苯胺、2，5-二氯-4-硝基苯胺、2-氰基-4-硝基苯胺、2-氰基-6-氯-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2，4-二硝基苯胺、2-氯-4，6-二硝基苯胺、2-溴-4，6-二硝基苯胺、2-氨基-5-硝基噻唑、2-氨基-3，5-二硝基噻吩、2-氨基-5-硝基噻吩-3-羧酸乙酯、2-氨基-3-氰基-4-氯-5-甲酰基噻吩、2-氨基-5-(4-硝基苯基偶氮基)-噻吩-3-甲腈、7-氨基-5-硝基苯并异噻唑、2-氨基-6-硝基苯并噻唑、2-氨基-6-甲磺酰基苯并噻唑、2-氨基-6-硫氰酸根合苯并噻唑或2-氨基-6，7-二氯苯并噻唑，而特别优选地衍生自2-氰基-4-硝基苯胺、2-氯-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2-氨基-6-硝基苯并噻唑或7-氨基-5-硝基苯并异噻唑。
式(I)的染料可通过制备偶氮化合物用的一般方法而获得，例如通过式(III)的胺的重氮化
D-NH2 (III)
其中D如上面给出的那样所定义，
及偶联至式(IV)的化合物
其中R1至R5、m及n如上面给出的那样所定义。
典型地，式(III)的胺可在-10至10℃温度下于酸性介质，如乙酸、丙酸或盐酸中，使用亚硝基化剂如亚硝酰基硫酸、亚硝酸钠或甲基亚硝酸钠而重氮化。偶联至式(IV)的化合物可通过在文献中所描述且本领域的技术人员已知的条件下将重氮化的胺添加于式(IV)的化合物中而实现。
在偶联后，式(I)的化合物可通过任何方便的手段如过滤而自反应混合物中回收。
含有乙烯酯的式(IV)的化合物可通过本领域普通技术人员知悉且描述于文献中的许多方法而由市售原料或文献所描述的原料制备。例如，烯醇酯官能可如Organic Synthesis，J.Wiley and sons，Inc.，CollectiveVolume IV，page 977中所描述的那样而获得。所需的烯醇乙酸酯前体可购得或制得。例如，烯醇乙酸酯化合物的合成描述于US 2,466,737中。
式(III)的化合物是已知的，或者可在本领域的技术人员已知的标准条件下轻易地制备。
式(I)的染料可用于染色及印花合成织物材料，特别是聚酯织物材料及其与例如纤维素材料如绵的纤维共混物，式(I)的染料可赋予这些织物材料以具有优异耐洗性的颜色。
以式(I)的染料来染色所提及的纤维物品可以本身已知的方式在80℃至110℃下通过竭染方法或在110℃至140℃的染色釜中通过HT方法，以及通过所谓的热固法，优选由水性分散体中、及如果适当的话在载体存在下进行，热固法中上述物品以染色液体压染、并随后在约180℃至230℃下固着。
所提及的纤维物品还可以本身已知的方式通过如下步骤来印花：将式(I)的染料掺入印花糊料中，及在180℃至230℃温度下、如果适当的话在载体存在下，以HT蒸汽、加压蒸汽或干热来处理该使用糊料印刷过的物品，以便使染料固着。
在上述应用所使用的染色液体及印花糊料中，式(I)的染料应当存在于尽可能最细的分散体中。染料的细分散体以本身已知的方式通过如下步骤来实现：将制备期间所得的染料连同分散剂悬浮于液体介质、优选悬浮于水中，并使该混合物暴露于剪切力的作用中，以机械方式粉碎最初存在的粒子至最佳比表面积实现及染料的沉降尽可能低的程度。染料的粒度通常在0.5与5μm之间，优选为约1μm。
使用的分散剂可以为非离子性或阴离子性。非离子性分散剂为例如环氧烷如环氧乙烷或环氧丙烷与可烷基化的化合物如脂肪醇、脂肪胺、脂肪酸、酚、烷基酚及羧酸胺的反应产物。阴离子性分散剂为例如木质素磺酸盐、烷基磺酸盐或烷基芳基磺酸盐或烷基芳基聚二醇醚硫酸盐。
对大部分的使用方法而言，该所获得的染料配方应当为可流动的。所以，染料及分散剂含量在这些例子中会有所限制。一般而言，使分散体达到高达50重量％的染料含量及高达25重量％的分散剂含量。基于经济原因，染料含量通常不会低于15重量％。
该分散体也可含有其它辅助剂，例如充当氧化剂或杀真菌剂的辅助剂。这类试剂为在本领域中已知的。由此制得的染料分散体可非常有利地用于印花糊料及染色液体的制备。
对某些用途领域而言，优选粉末配方。这些粉末包含染料、分散剂及其它辅助剂，诸如湿润剂、氧化剂、防腐剂及除尘剂。
用于粉状染料配方的优选制备方法包括例如通过真空干燥、冻干，通过于辊筒式干燥器上干燥，优选喷雾干燥，自上述的液体染料分散体中除去液体。
另外，本发明的式(I)染料也可有利地用在数字喷墨印花用的油墨中。
因此，本发明也涉及喷墨印花用的油墨，其含有至少一种式(I)的染料。
用于数字喷墨印花的油墨通常为水性油墨，其进一步含有0.1至20％的分散剂。可用的分散剂包括例如磺化或磺甲基化的木质素、芳族磺酸的甲醛缩合物、取代或未取代的酚衍生物的甲醛缩合物、聚丙烯酸酯及其共聚物、氧化苯乙烯聚醚、改性的聚氨酯、环氧烷与可烷基化的化合物的反应产物，可烷基化的化合物为例如脂肪醇、脂肪胺、脂肪酸、羧酰胺类、树脂酸及取代或未取代的酚。
用于连续流动过程的油墨可通过添加电解质而将电导率调整在0.5至25mS/cm范围内。
有用的电解质包括例如硝酸锂及硝酸钾。
此外，本发明的油墨可进一步含有总量为1-60重量％、优选为5-40重量％的典型喷墨有机溶剂。
实施例1
3-{[4-(2-氯-4-硝基苯基偶氮基)-苯基]-乙基-氨基}-丙酸乙烯酯
放入5.2份2-氯-4-硝基苯胺、20份丙酸及30份乙酸并冷却至5℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在10℃以下。将重氮化混合物于5-10℃再搅拌2小时。向单独的容器内放入6.5份3-(乙基-苯基-氨基)-丙酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌过夜，并通过过滤分离出产物，以水清洗并干燥，即可产生9.9份3-{[4-(2-氯-4-硝基苯基偶氮基)-苯基]-乙基-氨基}-丙酸乙烯酯。λmax＝510nm(DMF)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的红色色泽。
根据实施例1所述的步骤，制备表1的实施例2至64的式(Ia)染料。
表1
| 实施例 | G1 | G2 | G3 | G4 | R1 | R2 | R4 | λmax(nm)DMF |
| 2 | Cl | H | NO2 | Cl | H | H | C2H5 | 432* |
| 3 | Cl | H | NO2 | Br | H | H | C2H5 | 448 |
| 4 | Br | H | NO2 | Br | H | H | C2H5 | 446 |
| 5 | Cl | H | NO2 | Cl | H | H | C4H9 | 450 |
| 6 | Cl | H | NO2 | Br | H | H | C4H9 | 450 |
| 7 | Br | H | NO2 | Br | H | H | C4H9 | 448 |
| 8 | Cl | H | NO2 | Cl | H | H | CH2C6H5 | 436 |
| 9 | Cl | H | NO2 | Br | H | H | CH2C6H5 | 436 |
| 10 | Br | H | NO2 | Br | H | H | CH2C6H5 | 438 |
| 11 | H | Cl | Cl | H | H | H | C2H5 | 433* |
| 12 | H | H | NO2 | H | H | H | C2H5 | 481 |
| 13 | H | H | NO2 | CF3 | H | H | C2H5 | 516 |
| 14 | H | H | NO2 | H | CH3 | H | C2H5 | 500 |
| 15 | NO2 | H | H | H | CH3 | H | C2H5 | 496 |
| 16 | H | NO2 | H | H | CH3 | H | C2H5 | 484 |
| 17 | Cl | H | NO2 | H | CH3 | H | C2H5 | 525 |
| 18 | Cl | H | SO2CH3 | H | CH3 | H | C2H5 | 468* |
| 19 | NO2 | H | Cl | H | CH3 | H | C2H5 | 518 |
| 20 | Br | H | NO2 | H | CH3 | H | C2H5 | 523 |
| 21 | Cl | H | NO2 | Cl | CH3 | H | C2H5 | 462 |
| 22 | Cl | H | NO2 | Br | CH3 | H | C2H5 | 466 |
| 23 | Br | H | NO2 | Br | CH3 | H | C2H5 | 466 |
| 24 | H | Cl | NO2 | Cl | CH3 | H | C2H5 | 522 |
| 25 | H | H | NO2 | CF3 | CH3 | H | C2H5 | 530 |
| 26 | CN | H | NO2 | Cl | CH3 | H | C2H5 | 562 |
| 27 | CN | H | NO2 | Br | CH3 | H | C2H5 | 560 |
| 28 | Cl | H | NO2 | NO2 | CH3 | H | C2H5 | 560 |
| 实施例 | G1 | G2 | G3 | G4 | R1 | R2 | R4 | λmax(nm)DMF |
| 29 | CN | H | NO2 | H | CH3 | H | C2H5 | 551 |
| 30 | NO2 | H | NO2 | H | CH3 | H | C2H5 | 552 |
| 31 | Br | H | NO2 | NO2 | CH3 | H | C2H5 | 558 |
| 32 | H | H | NO2 | H | CH3 | H | C4H9 | 506 |
| 33 | Cl | H | NO2 | H | CH3 | H | C4H9 | 528 |
| 34 | Cl | H | NO2 | Cl | CH3 | H | C4H9 | 470 |
| 35 | Cl | H | NO2 | Br | CH3 | H | C4H9 | 471 |
| 36 | Br | H | NO2 | Br | CH3 | H | C4H9 | 468 |
| 37 | CN | H | NO2 | Cl | CH3 | H | C4H9 | 564 |
| 38 | CN | H | NO2 | Br | CH3 | H | C4H9 | 566 |
| 39 | Cl | H | NO2 | NO2 | CH3 | H | C4H9 | 567 |
| 40 | CN | H | NO2 | H | CH3 | H | C4H9 | 558 |
| 41 | NO2 | H | NO2 | H | CH3 | H | C4H9 | 555 |
| 42 | Br | H | NO2 | NO2 | CH3 | H | C4H9 | 564 |
| 43 | NO2 | H | H | H | CH3 | H | CH2C6H5 | 494 |
| 44 | NO2 | H | Cl | H | CH3 | H | CH2C6H5 | 514 |
| 45 | Cl | H | NO2 | Cl | CH3 | H | CH2C6H5 | 424* |
| 46 | Cl | H | NO2 | Br | CH3 | H | CH2C6H5 | 460 |
| 47 | Br | H | NO2 | Br | CH3 | H | CH2C6H5 | 462 |
| 48 | CN | H | NO2 | Cl | CH3 | H | CH2C6H5 | 556 |
| 49 | CN | H | NO2 | Br | CH3 | H | CH2C6H5 | 556 |
| 50 | Cl | H | NO2 | NO2 | CH3 | H | CH2C6H5 | 553 |
| 51 | CN | H | NO2 | H | CH3 | H | CH2C6H5 | 544 |
| 52 | NO2 | H | NO2 | H | CH3 | H | CH2C6H5 | 546 |
| 53 | Br | H | NO2 | NO2 | CH3 | H | CH2C6H5 | 552 |
| 54 | Cl | H | NO2 | H | NHAc | H | C2H5 | 542 |
| 55 | NO2 | H | NO2 | H | NHAc | H | C2H5 | 556 |
| 56 | Br | H | NO2 | CN | NHAc | H | C2H5 | 590 |
| 57 | NO2 | H | NO2 | Cl | NHAc | H | C2H5 | 568 |
| 58 | NO2 | H | NO2 | Br | NHAc | H | C2H5 | 566 |
| 59 | NO2 | H | NO2 | H | NHAc | OCH3 | H | 576 |
| 60 | NO2 | H | NO2 | Cl | NHAc | OCH3 | H | 594 |
| 61 | NO2 | H | NO2 | Br | NHAc | OCH3 | H | 594 |
| 62 | NO2 | H | NO2 | H | NHAc | OCH3 | C2H5 | 591 |
| 63 | NO2 | H | NO2 | Cl | NHAc | OCH3 | C2H5 | 598* |
| 64 | NO2 | H | NO2 | Br | NHAc | OCH3 | C2H5 | 611 |
*＝在丙酮中测得的λmax
实施例65
3-{[4-(5，6/6，7-二氯苯并噻唑-2-基偶氮基)-苯基]-乙基-氨基}-丙酸乙烯酯
放入6.5份2-氨基-5，6/6，7-二氯苯并噻唑、20份丙酸及30份乙酸并冷却至5℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在10℃以下。在5-10℃下搅拌该重氮化混合物另外的2小时。向单独的容器内放入6.5份3-(乙基-苯基-氨基)-丙酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌过夜，并通过过滤分离出产物，以水清洗并干燥，即可产生11.7份3-{[4-(5，6/6，7-二氯苯并噻唑-2-基偶氮基)-苯基]-乙基-氨基}-丙酸乙烯酯。λmax＝530nm(DMF)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的红色色泽。
根据实施例65所述的步骤，制备表2的实施例66至80的式(Ib)染料。
表2
| 实施例 | G6 | G5 | R1 | R4 | λmax(nm)DMF |
| 66 | Cl | 5/7-Cl | H | CH2C6H5 | 525 |
| 67 | NO2 | H | H | C2H5 | 550 |
| 68 | NO2 | H | H | CH2C6H5 | 542 |
| 69 | SO2CH3 | H | H | C2H5 | 538 |
| 70 | SO2CH3 | H | H | CH2C6H5 | 526 |
| 71 | SCN | H | H | C2H5 | 540 |
| 72 | SCN | H | H | CH2C6H5 | 532 |
| 73 | Cl | 5/7-Cl | CH3 | C2H5 | 542 |
| 74 | Cl | 5/7-Cl | CH3 | CH2C6H5 | 540 |
| 75 | NO2 | H | CH3 | C2H5 | 562 |
| 76 | NO2 | H | CH3 | CH2C6H5 | 554 |
| 77 | SO2CH3 | H | CH3 | C2H5 | 549 |
| 78 | SO2CH3 | H | CH3 | CH2C6H5 | 542 |
| 79 | SCN | H | CH3 | C2H5 | 551 |
| 80 | SCN | H | CH3 | CH2C6H5 | 544 |
实施例81
3-{乙基-[4-(5-硝基-苯并[c]异噻唑-3-基偶氮基)-苯基]-氨基}-丙酸乙烯酯
放入5.9份7-氨基-5-硝基苯并异噻唑、30份98％硫酸及8份85％磷酸，在60℃加热达30分钟，然后冷却至5℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在10℃以下。在5-10℃下搅拌该重氮化混合物另外的2小时。向单独的容器内放入6.5份3-(乙基-苯基-氨基)-丙酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌过夜，并通过过滤分离出产物，以水清洗并干燥，即可产生10.1份3-{乙基-[4-(5-硝基-苯并[c]异噻唑-3-基偶氮基)-苯基]-氨基}-丙酸乙烯酯。λmax＝606nm(DMF)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的蓝色色泽。
根据实施例81所述的步骤，制备表3的实施例82至84的式(Ic)染料。
表3
| 实施例 | R1 | R4 | λmax(nm)DMF |
| 82 | H | CH2C6H5 | 594 |
| 83 | CH3 | C2H5 | 620 |
| 84 | CH3 | CH2C6H5 | 610 |
实施例85
3-{[4-(3，5-二硝基-噻吩-2-基偶氮基)-苯基]-乙基-氨基}-丙酸乙烯酯
放入5.7份2-氨基-3，5-二硝基噻吩、20份丙酸及30份乙酸并冷却至2℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在4℃以下。在2-4℃下搅拌该重氮化混合物另外的2小时。向单独的容器内放入6.5份3-(乙基-苯基-氨基)-丙酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌过夜，并通过过滤分离出产物，随后以水、甲醇清洗并再次以水清洗，然后干燥，即可产生7.4份3-{[4-(3，5-二硝基-噻吩-2-基偶氮基)-苯基]-乙基-氨基}-丙酸乙烯酯。λmax＝626nm(丙酮)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的蓝色色泽。
根据实施例85所述的步骤，制备表4的实施例86至97的式(Id)染料。
表4
| 实施例 | G10 | G9 | G8 | R1 | R4 | λmax(nm)DMF |
| 86 | CO2C2H5 | H | NO2 | H | C2H5 | 602 |
| 87 | CN | Cl | CHO | H | C2H5 | 596 |
| 88 | CN | H | N＝NC6H4-p-NO2 | H | C2H5 | 662 |
| 89 | NO2 | H | NO2 | H | CH2C6H5 | 629 |
| 90 | CO2C2H5 | H | NO2 | H | CH2C6H5 | 584 |
| 91 | CN | Cl | CHO | H | CH2C6H5 | 590 |
| 92 | NO2 | H | NO2 | CH3 | C2H5 | 651 |
| 93 | CO2C2H5 | H | NO2 | CH3 | C2H5 | 612 |
| 94 | CN | Cl | CHO | CH3 | C2H5 | 610 |
| 95 | NO2 | H | NO2 | CH3 | CH2C6H5 | 645 |
| 96 | CO2C2H5 | H | NO2 | CH3 | CH2C6H5 | 605 |
| 97 | CN | Cl | CHO | CH3 | CH2C6H5 | 606 |
实施例98
3-{乙基-[3-甲基-4-(5-硝基-噻唑-2-基偶氮基)-苯基]-氨基}-丙酸乙烯酯
放入4.4份2-氨基-5-硝基噻唑、20份丙酸及30份乙酸并冷却至5℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在10℃以下。在5-10℃下搅拌该重氮化混合物另外的2小时。向单独的容器内放入7.0份3-(乙基-[3-甲基苯基]-氨基)-丙酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌过夜，并通过过滤分离出产物，随后以水、甲醇清洗并再次以水清洗，然后干燥，即可产生9.5份3-{乙基-[3-甲基-4-(5-硝基-噻唑-2-基偶氮基)-苯基]-氨基}-丙酸乙烯酯。λmax＝602nm(DMF)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的紫色色泽。
实施例99
4-{[4-(2-氯-4-硝基苯基偶氮基)-苯基]-乙基-氨基}-丁酸乙烯酯
放入5.2份2-氯-4-硝基苯胺、20份丙酸及30份乙酸并冷却至5℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在10℃以下。在5-10℃下搅拌该重氮化混合物另外的2小时。向单独的容器内放入7.0份4-(乙基-苯基-氨基)-丁酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌至过夜，并通过过滤分离出产物，以水清洗并干燥，即可产生10.4份4-{[4-(2-氯-4-硝基苯基偶氮基)-苯基]-乙基-氨基}-丁酸乙烯酯。λmax＝509nm(DMF)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的红色色泽。
根据实施例99所述的步骤，制备表5的实施例100至106的式(Ie)染料，但实施例102及106除外。在这些情况中，如实施例81所述，重氮化反应在硫酸与磷酸的混合物中进行，而非在丙酸与乙酸的混合物中进行。
表5
实施例107
3-{[4-(2-氯-4-硝基苯基偶氮基)-苯基]-乙基-氨基}-2-甲基-丙酸乙烯酯
放入5.2份2-氯-4-硝基苯胺、20份丙酸及30份乙酸并冷却至5℃。添加11.4份的40％(w/w)亚硝酰基硫酸，同时使温度维持在10℃以下。在5-10℃下搅拌该重氮化混合物另外的2小时。向单独的容器内放入7.0份3-(乙基-苯基-氨基)-2-甲基丙酸乙烯酯、100份甲醇、1份氨基磺酸及100份冰。在搅拌下，缓慢添加该重氮化混合物，接着添加另外的300份冰。使反应混合物搅拌过夜，并通过过滤分离出产物，以水清洗并干燥，即可产生9.4份3-{[4-(2-氯-4-硝基苯基偶氮基)-苯基]-乙基-氨基}-2-甲基-丙酸乙烯酯。λmax＝511nm(DMF)。
当由水性分散体施加到聚酯材料时，看到具有优异耐湿性及耐光性的红色色泽。
根据实施例107所述的步骤，制备表6的实施例108至120的染料，但实施例109、113、116及120除外。在这些情况中，如实施例81所述，重氮化反应在硫酸与磷酸的混合物中进行，而非在丙酸与乙酸的混合物中进行。
表6
实施例121
聚酯的织物利用在水中含有50g/l的8％藻酸钠溶液、100g/l的8-12％半乳甘露聚糖溶液及5g/l磷酸二氢钠的液体预处理，然后干燥。吸湿率(wet pickup)为70％。
利用按需(drop-on-demand)(泡沫喷射)喷墨印花头，以含有下列组份的水性油墨来印花由此预处理过的织物：
6％的根据实施例1的染料
1.5％的分散剂Disperbyk 190
10％的2-丙醇
20％的聚乙二醇200
0.01％杀菌剂Mergal K9N及
62.49％的水
使印花物完全干燥。通过175℃的饱和蒸汽进行固着达7分钟。
然后，温漂洗该印花物，以95℃的热水让该印花物经受坚牢性清洗，温漂洗，然后干燥。
结果是得到具有优异耐用性及耐洗性的印花物。
Claims (7)
1.式(I)的染料
其中
D为重氮成分；
R1为氢、(C1-C4)烷基、羟基、-NHCOR6或-NHSO2R6；
R2为氢、卤素或(C1-C4)烷氧基；
R3为氢或甲基；
R4为氢，(C1-C6)烷基，取代的(C1-C6)烷基，被选自-O-、-S-及-NR7的1、2或3个杂原子中断的(C2-C6)烷基，被选自-O-、-S-及-NR7的1、2或3个杂原子中断的取代的(C2-C6)烷基，(C2-C6)烯基，取代的(C2-C6)烯基，苄基，或苯乙基；
R5为氢或甲基；
R6为(C1-C4)烷基、苯基或取代的苯基；
R7为(C1-C4)烷基、苯基或取代的苯基；
m为0、1或2；及
n为0或1。
2.根据权利要求1的染料，其中D具有式(IIa)
其中
G1为氢、卤素、氰基或硝基；
G2为氢、卤素或硝基；
G3为氢、卤素、甲磺酰基、氟磺酰基或硝基；及
G4为氢、卤素、三氟甲基、氰基或硝基；
或者D具有式(IIb)
其中
G5为氢或卤素；及
G6为氢、卤素、硝基、-SO2CH3或-SCN；
或者D具有式(IIc)
其中
G7为氢或卤素；
或者D具有式(IId)
其中
G8为硝基、氰基、-CHO或式(IIe)的基团
其中G11及G12独立地为氢、卤素、硝基或氰基；
G9为氢或卤素；及
G10为硝基、氰基、-COCH3或-COO-G13，其中G13为C1-C4烷基；
或者D具有式(IIf)
3.根据权利要求1和/或2的染料，其中D衍生自下列胺：3，4-二氯苯胺、2-三氟甲基-4-硝基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2-氯-4-硝基苯胺、4-氯-2-硝基苯胺、2-溴-4-硝基苯胺、2-氯-4-甲磺酰基苯胺、2，6-二氯-4-硝基苯胺、2，6-二溴-4-硝基苯胺、2-氯-6-溴-4-硝基苯胺、2，5-二氯-4-硝基苯胺、2-氰基-4-硝基苯胺、2-氰基-6-氯-4-硝基苯胺、2-氰基-6-溴-4-硝基苯胺、2，4-二硝基苯胺、2-氯-4，6-二硝基苯胺、2-溴-4，6-二硝基苯胺、2-氨基-5-硝基噻唑、2-氨基-3，5-二硝基噻吩、2-氨基-5-硝基噻吩-3-羧酸乙酯、2-氨基-3-氰基-4-氯-5-甲酰基噻吩、2-氨基-5-(4-硝基苯基偶氮基)-噻吩-3-甲腈、7-氨基-5-硝基苯并异噻唑、2-氨基-6-硝基苯并噻唑、2-氨基-6-甲磺酰基苯并噻唑、2-氨基-6-硫氰酸根合苯并噻唑或2-氨基-6，7-二氯苯并噻唑。
4.根据权利要求1至3中一项或多项的染料，其中
R1为氢、甲基或-NHCOCH3；
R2为氢、氯、甲氧基或乙氧基；
R3为氢或甲基；
R4为氢、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、苄基、-CH2-O-CH2-或-(CH2)2-O-(CH2)2-；
R5为氢或甲基；
m为0、1或2；
n为0或1。
5.根据权利要求1至4中一项或多项的染料的制备方法，该方法包括将式(III)的胺重氮化
D-NH2 (III)
其中D如权利要求1中定义，
并偶联至式(IV)的化合物
其中R1至R5、m及n如权利要求1中定义。
6.根据权利要求1至4中一项或多项的染料在对合成织物材料及其纤维共混物的染色及印花中的用途。
7.喷墨印花用油墨，其包含至少一种根据权利要求1至4中一项或多项的式(I)的染料。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0622473.7A GB0622473D0 (en) | 2006-11-10 | 2006-11-10 | Disperse azo dyestuffs |
| GB0622473.7 | 2006-11-10 | ||
| PCT/EP2007/061806 WO2008055846A1 (en) | 2006-11-10 | 2007-11-02 | Disperse azo dyestuffs |
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| Publication Number | Publication Date |
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| CN101528856A true CN101528856A (zh) | 2009-09-09 |
| CN101528856B CN101528856B (zh) | 2013-07-03 |
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| CN2007800390890A Active CN101528856B (zh) | 2006-11-10 | 2007-11-02 | 分散偶氮染料 |
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| US (1) | US7871446B2 (zh) |
| EP (1) | EP2084232B1 (zh) |
| JP (1) | JP2010509418A (zh) |
| KR (1) | KR101431854B1 (zh) |
| CN (1) | CN101528856B (zh) |
| BR (1) | BRPI0717927A2 (zh) |
| CA (1) | CA2669107A1 (zh) |
| ES (1) | ES2390702T3 (zh) |
| GB (1) | GB0622473D0 (zh) |
| MX (1) | MX2009005010A (zh) |
| PT (1) | PT2084232E (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0625624D0 (en) * | 2006-12-21 | 2007-01-31 | Dystar Textilfarben Gmbh & Co | Disperse dye mixtures |
| US8305744B2 (en) * | 2010-05-14 | 2012-11-06 | Apple Inc. | Shock mounting cover glass in consumer electronics devices |
| EP2785797B1 (en) | 2011-11-30 | 2018-03-21 | Merck Patent GmbH | Particles for electrophoretic displays |
| US9383621B2 (en) | 2011-11-30 | 2016-07-05 | Merck Patent Gmbh | Electrophoretic fluids |
| CN102757660B (zh) * | 2012-07-10 | 2013-12-11 | 浙江龙盛集团股份有限公司 | 一种苯并异噻唑染料单体化合物及分散染料 |
| WO2014019650A1 (en) | 2012-08-01 | 2014-02-06 | Merck Patent Gmbh | Electrophoretic fluids |
| KR20150130450A (ko) | 2013-03-15 | 2015-11-23 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 염료로서의 벤조티아졸-2-일아조-페닐 화합물, 이 염료를 포함하는 조성물, 및 이러한 조성물의 경화도를 결정하는 방법 |
| CN103450707A (zh) * | 2013-09-07 | 2013-12-18 | 张家港市杨舍丝印工艺厂 | 染料组合物及其制备方法(黑色) |
| CN105899582B (zh) | 2013-12-30 | 2018-01-26 | 3M创新有限公司 | 包含多硫醇、不饱和化合物和染料的组合物，以及有关此类组合物的方法 |
| CN105874015B (zh) | 2013-12-30 | 2019-01-18 | 3M创新有限公司 | 染料、由其制备的填料、包括填料的组合物以及确定此类组合物的固化度的方法 |
| EP3313909B1 (en) | 2015-06-29 | 2021-12-08 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
| CN107619379B (zh) * | 2017-10-17 | 2018-07-24 | 安阳师范学院 | 一种2-胺基偶氮芳香化合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2466737A (en) * | 1944-06-06 | 1949-04-12 | Carbide & Carbon Chem Corp | Acylations with enol esters |
| IT1224790B (it) * | 1987-12-04 | 1990-10-24 | Sandoz Ag | Composti azoici, loro preparazione e loro impiego come coloranti dispersi. |
| DE3911120A1 (de) * | 1989-04-06 | 1990-10-11 | Cassella Ag | Monoazofarbstoffe, ihre herstellung und verwendung |
| DE4446943A1 (de) * | 1994-12-28 | 1996-07-04 | Cassella Ag | Verfahren zum Färben von Polyester und polyesterhaltigen Textilmaterialien |
| US6610219B2 (en) * | 2001-02-06 | 2003-08-26 | Battelle Memorial Institute | Functional materials for use in optical systems |
| GB0108318D0 (en) * | 2001-04-03 | 2001-05-23 | Clariant Int Ltd | Organic compounds |
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2006
- 2006-11-10 GB GBGB0622473.7A patent/GB0622473D0/en not_active Ceased
-
2007
- 2007-11-02 EP EP07847095A patent/EP2084232B1/en active Active
- 2007-11-02 ES ES07847095T patent/ES2390702T3/es active Active
- 2007-11-02 CN CN2007800390890A patent/CN101528856B/zh active Active
- 2007-11-02 CA CA002669107A patent/CA2669107A1/en not_active Abandoned
- 2007-11-02 US US12/514,232 patent/US7871446B2/en active Active
- 2007-11-02 WO PCT/EP2007/061806 patent/WO2008055846A1/en active Application Filing
- 2007-11-02 PT PT07847095T patent/PT2084232E/pt unknown
- 2007-11-02 JP JP2009535688A patent/JP2010509418A/ja not_active Withdrawn
- 2007-11-02 KR KR1020097008821A patent/KR101431854B1/ko active IP Right Grant
- 2007-11-02 BR BRPI0717927-8A2A patent/BRPI0717927A2/pt not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2669107A1 (en) | 2008-05-15 |
| TW200844184A (en) | 2008-11-16 |
| JP2010509418A (ja) | 2010-03-25 |
| ES2390702T3 (es) | 2012-11-15 |
| KR101431854B1 (ko) | 2014-08-26 |
| TWI409301B (zh) | 2013-09-21 |
| PT2084232E (pt) | 2012-09-26 |
| EP2084232B1 (en) | 2012-08-15 |
| US7871446B2 (en) | 2011-01-18 |
| EP2084232A1 (en) | 2009-08-05 |
| BRPI0717927A2 (pt) | 2013-11-05 |
| US20100009081A1 (en) | 2010-01-14 |
| WO2008055846A1 (en) | 2008-05-15 |
| GB0622473D0 (en) | 2006-12-20 |
| MX2009005010A (es) | 2009-05-20 |
| KR20090075846A (ko) | 2009-07-09 |
| CN101528856B (zh) | 2013-07-03 |
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