CN1059456C - 偶氮染料及其制法和用途 - Google Patents
偶氮染料及其制法和用途 Download PDFInfo
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- CN1059456C CN1059456C CN94104167A CN94104167A CN1059456C CN 1059456 C CN1059456 C CN 1059456C CN 94104167 A CN94104167 A CN 94104167A CN 94104167 A CN94104167 A CN 94104167A CN 1059456 C CN1059456 C CN 1059456C
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- Prior art keywords
- hydrogen
- dyestuff
- chlorine
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- methyl
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- 239000000987 azo dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 25
- 238000004043 dyeing Methods 0.000 claims abstract description 20
- 229920000728 polyester Polymers 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000460 chlorine Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000006193 diazotization reaction Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- -1 4Be hydrogen Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000007639 printing Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- 239000004753 textile Substances 0.000 abstract description 18
- 239000000986 disperse dye Substances 0.000 abstract 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 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000000047 product Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical class [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- JYESXCFBVNUOSJ-UHFFFAOYSA-N (4-nitrophenyl)cyanamide Chemical class [O-][N+](=O)C1=CC=C(NC#N)C=C1 JYESXCFBVNUOSJ-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-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
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical class C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VGDKCRMZIWPMPW-UHFFFAOYSA-N n-(3-aminophenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(N)=C1 VGDKCRMZIWPMPW-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 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
- 238000010992 reflux Methods 0.000 description 1
- 238000010019 resist printing Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
- B41M5/388—Azo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Coloring (AREA)
Abstract
本发明公开了一种式(1)的分散染料,式中各取代基定义如说明书中所示。这类染料特别适用于聚酯纺织材料的染色,并具有优异耐光性的特色。
Description
本发明涉及分散染料及其制备以及其在纺织材料染色上的应用。
分散染料(即没有水增溶基的染料)在本技术领域里早已熟知,且常用于疏水纺织材料的染色。然而,所得染色的耐热迁移性能往往不能满足要求。这种问题特别会在印染红色到蓝色色调的情况下发生。
为了弥补上述缺陷,已开发了一些特殊染料,由于其分子尺寸和/或体溶度的缘故,其扩散能力尽可能低。然而,用这种性质的染料染色常常会产生困难,因为这类染料不能在尽染法染色中使用,或仅能有限地使用,甚至在热溶法中,这些染料通常要求过高的固色温度,这是不受欢迎的。
因此,本发明涉及这样一些分散染料,其所产生的染色非常耐热迁移而且在尽染和热溶法以及织物印花时仍然具有良好的提升。而且这些染料还适用于拔染印花。
本发明的染料具有如下结构式:式中,D是苯、萘、联苯、偶氮苯、噻吩、苯并噻唑、苯并异噻唑、噻唑、噻二唑、吲唑、苯并三唑、吡唑、蒽醌、萘酚酰亚胺、色酮或二苯并呋喃系列重氮成分的基团;X是氢、甲基、卤素或-NH-CO-R,其中,R是甲基、乙基、丙基、异丙基、乙氧基或氨基;Y是氢、卤素、甲氧基或-O-(CH2)m-OR′,其中R′是氢、CH3或CH2CH2CN,和n是1-6的整数;R3是C1-C6烷基,和R4是氢、C1-C6烷基或烯丙基。
在结构式(1)特别有用的染料中,X优选-NH-CO-R或Cl,其中R的定义同上。Y优选氢、氯基或氟基。R3优选CH3、C2H5、C3H7和C4H9。特别优选CH3。R4优选氢或烯丙基。特别优选氢。
在结构式(1)特别有用的染料中,D是如下结构式的基团式中,A1优选氢、氯基、氰基、硝基、甲基或COOCH3;A2是氢、卤素或氰基;A3是氢、氯基、COOCH3或COOCH(CH3)2以及A4是氢、甲基、氯基、硝基、COOCH3、SO2CH3、OSO2-C6H5或SO2C2H5。在这些染料中,A1是氯基或氰基、A2是氢或氯基、A3是氢或氯基和A4是硝基或SO2CH3的染料特别具有重要价值。
结构式(1)的新偶氮染料可采用其已知的方法制备。该染料可以方便地通过重氮化如下结构式的化合物进行制备:然后将该化合物的重氮化盐偶合成下式的偶合成分:以上结构式(3)和(4)中,A1、A2、A3、A4、X、Y、R3和R4的定义与结构式(1)和(2)中的相同。
结构式(3)化合物的重氮化按其已知的方法进行,典型的是在酸性介质(用盐酸或硫酸水溶液介质较适宜)中用亚硝酸钠。不过,也可以用其它的重氮化剂进行,而用亚硝基硫酸较适宜。该重氮化的反应介质可以含另外的酸,典型的是磷酸、硫酸、乙酸、丙酸、盐酸或这些酸的混合物,例如磷酸和乙酸的混合物。进行重氮化的温度范围为-10-30℃,典型的为-10℃-室温。
同样可按已知的方法将结构式(3)重氮化的化合物偶合为结构式(4)的偶合成分,该反应适宜在酸、水溶液或水溶液-有机介质中进行,优选温度范围为-10-30℃,更优选温度范围为-10-10℃。所用的酸典型的是盐酸、乙酸、硫酸或磷酸。重氮化和偶合反应适宜采用一罐法,即,在相同的反应介质中进行。
结构式(3)的重氮基成分是已知的化合物或可按其已知的方法制备。
结构式(4)的偶合成分同样可按其已知的方法制备。
结构式(1)的新化合物可以作为染料印染半合成和优选的合成疏水纤维材料,特别是纺织材料。包含半合成或合成的疏水纺织材料混纺的纺织材料也可以用该新化合物染色或印花。
具体的半合成纺织材料是二代乙酸纤维素和三乙酸纤维素。
合成的疏水纺织材料主要包括直链芳族聚酯类,该类聚酯典型的是由对苯二酸和二醇类,特别是乙二醇,或对苯二酸和1,4-双(羟甲基)环己烷的缩合物制成的;或由聚碳酸酯例如由α,α-二甲基-4,4′-二羟基二苯甲烷和光气,或由聚氯乙烯和聚酰胺纤维组成。
这类新化合物用已知的染色方法施用到纺织材料上。聚酯材料适宜采用尽染法于水分散体中,并在常用的阴离子或非离子洗涤剂且通常在常用的溶胀剂(载体)的存在下,在温度范围为80-140℃下进行染色。二代乙酸纤维素优选在温度范围为65-85℃下染色,而三乙酸纤维素在温度115℃以下染色。
这类新染料不会在染浴中同时使羊毛和棉织品染色,或仅有很小的染色效果(很好地防染),因此,这类染料也可以用于聚酯/羊毛和聚酯/纤维素混纺织物的染色。
这类新染料适用于热溶法染色、尽染和印花。
这类纺织材料可以呈任一种形式,包括纤维、纱线或无纺织物或纺织织物或针织织物。
在使用前,可以方便地将这类新染料转化成一种染料配方。这可通过该染料研磨到平均粒度为0.1-10微米而进行。可在分散剂存在下进行研磨。典型的方法是,将该染料与分散剂在一起研磨,或与分散剂捏和成浆状,然后,进行真空干燥或喷雾干燥。印染浆和染浴可以通过在所得的配方中添加水而制成。
常用的增稠剂可用于印花。这种增稠剂的说明性实例是改性的或未改性的天然产物,具有代表性的是藻酸盐、糊精、阿拉伯胶、结晶树胶、角豆树胶、黄蓍胶、羧甲基纤维素、羟乙基纤维素、淀粉或合成的产品包括聚丙烯酰胺、聚丙烯酸或其共聚物或聚乙烯醇。
以上列举的材料,特别是聚酯材料用新染料染色可以得到优异使用性能的匀染色调,特别是具有耐热定形、耐褶裥、抗氯和耐湿的性能,例如耐水、耐汗和耐洗褪色。该染料还显示出优异的耐磨度特色。可选出来特别加以说明的是优良的耐热迁移和优异的耐光性的染色。
这类新染料也可以方便地用来与其它的染料一起获得各种各样的色调。当然,也可以使用这些新染料相互的混合物。
此外,这类新染料非常适用于由超临界CO2制得的疏水纺织材料的染色。
本发明另外的目的是上述的结构式(1)偶氮染料的使用以及半合成或合成的疏水材料(优选纺织材料)的染色和印花的方法,该方法包括将一种或多种结构式(1)的化合物印染所述材料或掺入其中。疏水纤维材料优选聚酯纺织材料。另一些可用本发明方法和优选的操作条件处理的材质,已在上述有关该新化合物使用的详细说明中进行了讨论。
用本发明的方法染色或印花的疏水纤维材料(优选聚酯纺织材料)也构成本发明的目的。
结构式(1)的新染料也适用于现代化的压印法,例如传热印花法。
下列非限制性实施例旨在对本发明作详细说明,其中,除非另有说明,份数和百分率均以重量计。实施例1 将10.7克间甲苯胺、45毫升2-氯丙酸甲酯、10克碳酸钠和0.5克溴化钠的混合物在125-130℃下搅拌18小时。随后,将该反应混合物冷却到室温,并用乙酸乙酯/水的混合物萃取。然后将乙酸乙酯相在旋转式汽化器中浓缩,得到17克如下式的黄棕色的油用传统的方法将3.3克2-氰基-4-硝基苯胺在浓硫酸中重氮化,并将所得重氮化的盐在pH3-5下偶合为等当量的上述偶合成分。将该粗制品通过过滤分离,并与100毫升甲醇混合,在回流温度下将该混合物搅拌2小时,趁热过滤。将过滤产物干燥,即得到6克结晶,其熔点为175-177℃。该染料具有如下结构式并可将聚酯纺织材料染成红色色调。所得染色具有坚固的牢度,特别是具有良好的耐热迁移和耐光性能。实施例2 将16.4克3-丙酰胺基苯胺、11.7克粉状碳酸钠、1.6克溴化钠和50毫升2-氯丙酸甲酯的混合物在120-130℃下搅拌5小时。随后,将该反应混合物冷却到120℃,趁热过滤,并用20毫升2-氯丙酸甲酯洗涤该过滤产物。然后将滤液在旋转式汽化器中浓缩,得到25克如下式的粉末用传统的方法将17.3克2-氯基-4-硝基苯胺在浓硫酸中重氮化,并将所得重氮化的盐在pH3-5下偶合为等当量的上述偶合成分。将该粗制品通过过滤分离,并与100克水混合,将该混合物在95-97℃下搅拌1小时,然后,冷却到70℃,过滤。将过滤产物干燥,即得到红色的粉末,其熔点为165-167℃。该染料具有如下结构式并可将聚酯纺织材料染成鲜艳的红色色调。实施例3-101 下列染料可按实施例1和2中所述的方法制得。这些染料可将聚酯纺织材料染成后列表1-8中所示的色调。
Claims (14)
2.根据权利要求1的染料,其中R4是氢。
3.根据权利要求1或2的染料,其中X是-NH-CO-R或氯,R的定义与权利要求1中的相同。
4.根据权利要求1或2的染料,其中R3是CH3。
5.根据权利要求1的染料,其中D是下式基团其中A1是氢,氯或氰基,A2是氢,卤素或氰基,A3是氢,氯,COOCH3或COOCH(CH3)2和A4是硝基,SO2CH3,OSO2C6H5或SO2C2H5。
6.根据权利要求5的染料,其中A1是氯或氰基。
7.根据权利要求5的染料,其中A3是氢或氯。
8.根据权利要求5的染料,其中A4是硝基或SO2CH3。
9.根据权利要求5的染料,其中A1是氯或氰基,A2是氢中氯,A3是氢或氯,和A4是硝基或SO2CH3。
12.根据权利要求11的方法,其中R4是氢。
13.一种半合成或合成的疏水材料的染色或印花的方法,该方法包括将如权利要求1所定义的一种或多种化合物施用于或掺入所述的材料。
14.根据权利要求13的方法,其中半合成或合成的疏水材料是聚酯纤维材料。
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CN105439896A (zh) * | 2014-09-28 | 2016-03-30 | 上海安诺其集团股份有限公司 | 一种偶氮苯胺类的化合物 |
CN105523959A (zh) * | 2014-09-28 | 2016-04-27 | 上海安诺其集团股份有限公司 | 一种偶氮苯胺类的化合物的制备方法 |
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PL193092B1 (pl) * | 1997-07-15 | 2007-01-31 | Ciba Sc Holding Ag | Barwnik zawiesinowy, sposób wytwarzania barwnika, skladnik sprzęgający, zastosowanie barwnika oraz peparat barwiący |
TW522163B (en) * | 1998-04-23 | 2003-03-01 | Ciba Sc Holding Ag | Dye, coupling component and processes for the preparation of the same |
EP0952190B1 (de) * | 1998-04-23 | 2003-06-04 | Ciba SC Holding AG | Dispersionsfarbstoffe |
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ES2108959T3 (es) | 1998-01-01 |
EP0623654B1 (de) | 1997-09-24 |
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DE59404127D1 (de) | 1997-10-30 |
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