CN116082855A - Method for preparing disperse dye by using TDA tar - Google Patents
Method for preparing disperse dye by using TDA tar Download PDFInfo
- Publication number
- CN116082855A CN116082855A CN202310000364.9A CN202310000364A CN116082855A CN 116082855 A CN116082855 A CN 116082855A CN 202310000364 A CN202310000364 A CN 202310000364A CN 116082855 A CN116082855 A CN 116082855A
- Authority
- CN
- China
- Prior art keywords
- acid
- tar
- tda
- tda tar
- dye
- 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.)
- Pending
Links
- 239000000986 disperse dye Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000004043 dyeing Methods 0.000 claims abstract description 27
- 239000012065 filter cake Substances 0.000 claims abstract description 21
- LUEWUZLMQUOBSB-FSKGGBMCSA-N (2s,3s,4s,5s,6r)-2-[(2r,3s,4r,5r,6s)-6-[(2r,3s,4r,5s,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5s,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](OC3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-FSKGGBMCSA-N 0.000 claims abstract description 16
- 229920002581 Glucomannan Polymers 0.000 claims abstract description 16
- 229940046240 glucomannan Drugs 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 11
- 239000004753 textile Substances 0.000 claims abstract description 8
- -1 nitrophenol compound Chemical class 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000007670 refining Methods 0.000 claims abstract description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 238000005406 washing Methods 0.000 claims description 33
- 230000018044 dehydration Effects 0.000 claims description 24
- 238000006297 dehydration reaction Methods 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000835 fiber Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000000967 suction filtration Methods 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- SYDNSSSQVSOXTN-UHFFFAOYSA-N 2-nitro-p-cresol Chemical compound CC1=CC=C(O)C([N+]([O-])=O)=C1 SYDNSSSQVSOXTN-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 claims description 2
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical class CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 claims description 2
- CSSGKHVRDGATJL-UHFFFAOYSA-N 3-fluoro-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(F)=C1 CSSGKHVRDGATJL-UHFFFAOYSA-N 0.000 claims description 2
- ZHRLVDHMIJDWSS-UHFFFAOYSA-N 4-fluoro-2-nitrophenol Chemical compound OC1=CC=C(F)C=C1[N+]([O-])=O ZHRLVDHMIJDWSS-UHFFFAOYSA-N 0.000 claims description 2
- ORPHLVJBJOCHBR-UHFFFAOYSA-N 403-19-0 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1F ORPHLVJBJOCHBR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000011082 depyrogenation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 210000002268 wool Anatomy 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 44
- 239000003513 alkali Substances 0.000 abstract description 12
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 9
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000004744 fabric Substances 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 150000004998 toluenediamines Chemical class 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 238000004044 disperse dyeing Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- ZDFGMUPYJLPKGD-UHFFFAOYSA-N 3-[n-(2-hydroxyethyl)-4-[(6-methylsulfonyl-1,3-benzothiazol-2-yl)diazenyl]anilino]propanenitrile Chemical compound S1C2=CC(S(=O)(=O)C)=CC=C2N=C1N=NC1=CC=C(N(CCO)CCC#N)C=C1 ZDFGMUPYJLPKGD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007774 longterm Effects 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
-
- 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
-
- 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
- C09B67/0055—Mixtures of two or more disazo 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
- 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
- C09B67/006—Preparation of organic pigments
-
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- 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
- D06P1/19—Nitro 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention discloses a method for preparing disperse dye by using TDA tar, which comprises the steps of refining and concentrating dinitrotoluene hydrogenation reaction liquid to obtain TDA tar; reacting TDA tar with nitrophenol compound and acid to obtain TDA tar disperse dye; the TDA tar disperse dye reacts with glucomannan and acid, and the modified TDA tar disperse dye filter cake is obtained after purification and is applied to dyeing of textile materials. The invention realizes the resource utilization of TDA tar, avoids the problem of environmental pollution, and has excellent environmental friendliness; the invention adopts the glucomannan to crosslink and modify the TDA tar disperse dye, which obviously improves the alkali resistance, the dye uptake and the color fastness of the dye, has the advantages of low cost and low toxicity, and expands the application range of the dye.
Description
Technical Field
The invention belongs to the field of dye chemical industry, and particularly relates to a method for preparing disperse dye by using TDA tar.
Background
Toluene Diamine (TDA) is a main raw material for producing toluene diisocyanate, and is obtained by catalytic hydrogenation of dinitrotoluene, and heavy component tar is produced in the reaction process. In the past, TDA tar is generally buried, which causes pollution to soil and water quality, and at present, incineration treatment is mainly adopted, but harmful substances such as nitrogen oxides, sulfur oxides, dioxin and the like are generated, so that atmospheric pollution is caused.
In order to avoid the problem of environmental pollution caused by the treatment of TDA tar, methods for converting and applying the TDA tar are disclosed.
Patent CN109790104a provides a method for reacting TDA tar with hydrogen to produce valuable products such as methylcyclohexylamine and methylcyclohexyldiamine in the presence of a hydrogenation noble metal catalyst. Patent CN206669760U provides a TDA tar liquid incineration system for TDA tar burns more fully and tail gas up to standard. The method has the problems of complex treatment process, high cost or incomplete treatment.
In recent years, the polyester printing and dyeing industry adopts a disperse dyeing one-bath method, and mainly adopts alkali-resistant disperse dye, so that dyed fabrics have the advantages of soft hand feeling, good leveling property, few defects and the like, and meanwhile, the consumption of water resources and the discharge of printing and dyeing wastewater are reduced.
The disperse dyeing one bath method requires that the disperse dye has high alkali resistance, and the performance is difficult to meet by common azo dyes. The patent CN115044224A improves the alkali resistance and the vividness of azo disperse dyes by introducing coupling reagent of fluorine-containing aromatic amine. CN114940834a uses fluorine-containing aniline derivative or heterocyclic derivative as diazo component, uses hydroxy-and cyano-containing aniline derivative as coupling component, and the alkali resistance and oxidation resistance of the synthesized disperse dye are improved. Patent CN111978756a enhances the alkali resistance and oxidation resistance of thiazole heterocyclic azo disperse dyes by synthesizing the disperse dyes. The fluorine element is introduced into the dye, so that the cost is high, the stability is poor, the dye-uptake and the color fastness are low, and the dye-uptake and the color fastness are harmful to the health of human bodies and the environment after long-term contact, so that the application range is limited.
Disclosure of Invention
Aiming at the problems, the invention aims to provide a method for preparing disperse dye by using TDA tar, which realizes the recycling of the TDA tar, avoids the problem of environmental pollution and has excellent environmental friendliness; on the other hand, the glucomannan is adopted to modify the TDA tar dye, so that the alkali resistance, the dye uptake and the color fastness of the dye are obviously improved, and meanwhile, the dye has the advantages of low cost and low toxicity, and the application range of the dye is widened.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a method for preparing disperse dye by using TDA tar, comprising the following steps:
1) Dissolving TDA tar with a solvent I, uniformly mixing with a nitrophenol compound, regulating the pH of a reaction solution to 3-7 with an acid solution, stirring for reaction, carrying out suction filtration, washing with water, and drying to obtain a TDA tar disperse dye filter cake.
2) Dissolving the TDA tar disperse dye filter cake with a second solvent, adding glucomannan, adjusting the pH of the reaction solution to 3-7 with an acid solution, reacting, carrying out suction filtration, washing with water, and drying to obtain the disperse dye filter cake.
Preferably, the TDA tar in the step 1) is obtained by concentrating dinitrotoluene hydrogenation reaction liquid.
Preferably, the TDA tar is concentrated and then used as the raw material in the step 1), and the concentration can be performed by adopting a dehydration rectifying tower, a deparaffinization rectifying tower and an evaporator for refining, wherein the toluene diamine content is 20-50wt%, preferably 35-45wt%.
Preferably, the nitrophenol compound of step 1) may be one or more of nitrocresols, amino-containing nitrophenols or fluoronitrophenols, preferably 2-nitrop-cresol, 2, 6-dinitrop-cresol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 2-fluoro-4-nitrophenol, 3-fluoro-4-nitrophenol, 4-fluoro-2-nitrophenol;
preferably, the acid for adjusting the pH of the reaction solution in the step 1) can be an inorganic acid or an organic acid, preferably one or more of sulfamic acid, oxalic acid, sulfuric acid, hydrochloric acid and phosphoric acid, and the acid concentration is generally 3-10wt%;
preferably, the mass ratio of TDA tar to solvent one is 1: 2-5, wherein the mass ratio of the TDA tar to the nitrophenol compound is 1:0.1 to 0.5;
preferably, the solvent one comprises one or more of alcohols, ketones, ethers or amides, preferably methanol, ethanol, acetone, tetrahydrofuran, 1, 4-dioxane, N-dimethylformamide, N-dimethylacetamide.
Preferably, the pH of the reaction solution is 4 to 6; the reaction temperature is 40-80 ℃ and the reaction time is 0.5-2 h.
Preferably, the solvent two comprises alcohols, ketones or carboxylic acids, preferably one or more of methanol, ethanol, acetone, formic acid, acetic acid.
Preferably, the acid in the step 2) is an organic acid or an inorganic acid, preferably one or more of sulfamic acid, sulfuric acid, hydrochloric acid and phosphoric acid, and the acid concentration is 3-10wt%;
preferably, the mass ratio of the TDA tar to the solvent II is 1: 2-5, wherein the mass ratio of the TDA tar to the glucomannan is 1:0.1 to 0.5;
preferably, the reaction in the step 2) can be carried out under the ultrasonic condition, and the ultrasonic frequency is 50-125 Hz; the reaction temperature is 100-140 ℃ and the reaction time is 10-20 h;
more preferably, the pH of the reaction solution after the acid addition adjustment in the step 2) is 4 to 6.
The invention also provides the use of the disperse dyes prepared by the process according to the invention for dyeing textile materials.
Preferably, the textile material is one or more of cotton cloth, linen, silk, woolen cloth, leather, chemical fiber and blending.
Preferably, the dyeing condition PH is 2-14.
The concentrated TDA tar is subjected to secondary conversion with nitrophenol and acid solution, diazotization, coupling, dehydration, oxidation and other reactions are carried out, so that the residual anilines and diazobenzene substances in the TDA tar are converted into azobenzene substances, azoxybenzene substances and phenazine substances, and the TDA tar disperse dye is obtained after purification. Azo substances in the dye have certain alkali resistance, amino groups and nitro groups on the benzene ring can further enhance the alkali resistance, phenazine substances are beneficial to improving the washing fastness and the light fastness of textiles, and the alkali resistance, the dye uptake and the color fastness of the dye still need to be further improved.
The invention further carries out crosslinking reaction on the TDA tar disperse dye and the glucomannan, and the molecules are connected through ether bonds or hydrogen bonds in the crosslinking process to obtain the modified TDA tar disperse dye.
The invention has the remarkable advantages that:
1) The modified TDA tar disperse dye is obtained by secondarily converting the TDA tar and crosslinking the glucomannan, so that the recycling of the TDA tar is realized, the problem of environmental pollution is avoided, and the modified TDA tar disperse dye has excellent environmental friendliness.
2) The invention adopts the glucomannan to crosslink and modify the TDA tar disperse dye, which obviously improves the alkali resistance, the dye uptake and the color fastness of the dye, has the advantages of low cost and low toxicity, and expands the application range of the dye.
Detailed Description
The invention is further described in detail below with reference to examples for the purpose of further disclosure, but not limitation.
TDA tar was obtained from Toluene Diisocyanate (TDI) production equipment from Wanhua chemical Fujian.
The dyeing method comprises the following steps:
1g of dye filter cake is taken, ground and uniformly mixed with 100ml of water, 10g of polyester fiber cloth is taken, the weight of dye to the fabric is 4% owf, and the bath ratio is 1:15, respectively preparing NaOH solutions of 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10g/L to prepare dye baths with different PH values, respectively placing 10g of polyester fiber cloth into the different dye baths at 30 ℃, heating to 130 ℃ within 40min, preserving heat for 70min, washing with water, and drying to obtain the dyed polyester fiber cloth.
The performance test method comprises the following steps:
1) Alkali resistance: the dye was used to dye textile materials in different pH and different concentration NaOH dyebaths, respectively, and the highest pH resistance and the highest NaOH resistance (g/L) were evaluated.
2) Dye-uptake rate: after the dyeing is finished, the absorbance of the dye liquor is analyzed by an ultraviolet spectrophotometer at the maximum absorption wavelength, and the dye uptake calculation formula is as follows: dye uptake = (1-At/A0) ×100%, where A0 is the dye liquor absorbance At the start of dyeing and At is the dye liquor absorbance after dyeing to fixation.
3) Color fastness: according to GB/T3920-2018 "fabrics color fastness to rubbing test color fastness", a manual rubbing fastness meter is adopted to measure the rubbing color fastness of the sample; according to GB/T3921-2008 "fastness to washing for textile color fastness test", a washing fastness tester is adopted to test the fastness to washing of the sample.
Example 1:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. The kettle liquid of the deparasiting rectifying tower enters an evaporator, the temperature of the evaporator is 210 ℃, the pressure of the evaporator is 3kPaa, and TDA tar with 35 weight percent of m-toluenediamine is obtained from the bottom of the evaporator. 100g of TDA tar is dissolved by 300g of acetone, evenly mixed with 30g of 2-nitro-p-cresol, the pH of the reaction solution is adjusted to 4 by 5wt% sulfamic acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed by water and dried to obtain a TDA tar disperse dye filter cake. 10g of TDA tar dye filter cake is dissolved by 40g of acetone, 2.5g of glucomannan is added, the pH of the reaction solution is adjusted to 5 by 5wt% of sulfamic acid solution, the reaction is carried out for 15 hours at 100 Hz and 110 ℃, and the modified TDA tar disperse dye is obtained through suction filtration, water washing and drying.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 12, the highest NaOH-resistant concentration is 10g/L, the dye-uptake is 98.3%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 5, the washing color fastness is fading 5, and the washing color fastness is staining 5.
Example 2:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. Feeding the residue of the deparasiting rectifying tower into an evaporator, wherein the temperature of the evaporator is 207 ℃, the pressure of the evaporator is 3kPaa, and obtaining TDA tar with the m-toluenediamine content of 45wt% from the bottom of the evaporator. 100g of TDA tar is dissolved by 300g of acetone, evenly mixed with 20g of 2, 6-dinitro-p-cresol, the pH of the reaction solution is adjusted to 5 by 5wt% of phosphoric acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed by water and dried to obtain a TDA tar disperse dye filter cake. 10g of TDA tar dye filter cake is dissolved by 40g of acetone, 2.5g of glucomannan and 5wt% of phosphoric acid solution are added to adjust the pH of the reaction solution to 5, and the reaction is carried out for 15 hours at the temperature of 100 Hz and 110 ℃, and the modified TDA tar-based disperse dye is obtained through suction filtration, water washing and drying.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 13, the highest NaOH-resistant concentration is 10g/L, the dye-uptake is 97.4%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 5, the washing color fastness is fade 4, and the washing color fastness is stained 5.
Example 3:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. Feeding the residue of the deparasiting rectifying tower into an evaporator, wherein the temperature of the evaporator is 207 ℃, the pressure of the evaporator is 3kPaa, and obtaining TDA tar with the m-toluenediamine content of 45wt% from the bottom of the evaporator. 100g of TDA tar is dissolved by 300g of ethanol, evenly mixed with 45g of 2-amino-4-nitrophenol, the pH of the reaction solution is adjusted to 6 by 5wt% of sulfamic acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed by water and dried to obtain a TDA tar disperse dye filter cake. Dissolving 10g of TDA tar dye filter cake with 40g of ethanol, adding 1.5g of glucomannan and 5wt% sulfamic acid solution to adjust the pH of the reaction solution to 5, reacting for 15h at 80 Hz and 110 ℃, carrying out suction filtration, washing with water, and drying to obtain the modified TDA tar disperse dye.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 12, the highest NaOH-resistant concentration is 8/L, the dye-uptake is 96.2%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 5, the washing color fastness is fade 5, and the washing color fastness is stained 4.
Example 4:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. And (3) feeding the residue of the deparaffinization rectifying tower into an evaporator, wherein the temperature of the evaporator is 200 ℃, the pressure of the evaporator is 3kPaa, and obtaining TDA tar with the m-toluenediamine content of 50wt% from the bottom of the evaporator. 100g of TDA tar is dissolved by 300g of ethanol, evenly mixed with 15g of 2-nitro-p-cresol, the pH of the reaction solution is regulated to 4 by 5wt% of sulfuric acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed by water and dried to obtain a TDA tar disperse dye filter cake. 10g of TDA tar dye filter cake is dissolved by 40g of ethanol solution, 1.1g of glucomannan and 5wt% sulfuric acid solution are added to adjust the pH of the reaction solution to 5, and the reaction is carried out for 15 hours at 100 Hz and 110 ℃, and the modified TDA tar-based disperse dye is obtained through suction filtration, water washing and drying.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 10, the highest NaOH-resistant concentration is 7g/L, the dye-uptake is 94.7%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 4, the washing color fastness is fade 4, and the washing color fastness is stained 5.
Example 5:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. The kettle liquid of the deparasiting rectifying tower enters an evaporator, the temperature of the evaporator is 210 ℃, the pressure of the evaporator is 3kPaa, and TDA tar with 35 weight percent of m-toluenediamine is obtained from the bottom of the evaporator. 100g of TDA tar is dissolved by 300g of N, N-dimethylformamide, evenly mixed with 30g of 2-nitro-p-cresol, the pH of the reaction solution is regulated to 4 by 5wt% of sulfamic acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed and dried to obtain a TDA tar disperse dye filter cake. 10g of TDA tar dye filter cake is dissolved by 45g of formic acid solution, 5g of glucomannan and 5wt% sulfamic acid solution are added to adjust the pH of the reaction solution to 5, and the reaction is carried out for 15 hours at the temperature of 120 Hz and 110 ℃, and the modified TDA tar disperse dye is obtained through suction filtration, water washing and drying.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 12, the highest NaOH-resistant concentration is 10g/L, the dye-uptake is 97.9%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 5, the washing color fastness is fading 5, and the washing color fastness is staining 5.
Example 6:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. The kettle liquid of the deparasiting rectifying tower enters an evaporator, the temperature of the evaporator is 210 ℃, the pressure of the evaporator is 3kPaa, and TDA tar with 35 weight percent of m-toluenediamine is obtained from the bottom of the evaporator. 100g of TDA tar is dissolved by 400g of tetrahydrofuran, evenly mixed with 30g of 2-amino-4-nitrophenol, the pH of the reaction solution is adjusted to 4 by 5wt% of oxalic acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed by water and dried to obtain a TDA tar disperse dye filter cake. 10g of TDA tar dye filter cake is dissolved by 40g of acetic acid solution, 2.5g of glucomannan and 5wt% of oxalic acid solution are added to adjust the pH of the reaction solution to 5, the reaction is carried out for 15 hours at 125 Hz and 140 ℃, and the modified TDA tar disperse dye is obtained through suction filtration, water washing and drying.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 11, the highest NaOH-resistant concentration is 9g/L, the dye-uptake is 98.8%, the rubbing color fastness is dry 5, the wet rubbing color fastness is wet 5, the washing color fastness is fade 4, and the washing color fastness is stained 4.
Comparative example 1:
adding dinitrotoluene hydrogenation reaction liquid into a dehydration rectifying tower, wherein the temperature of a tower kettle is 220 ℃, and the pressure of the tower kettle is 110kPaa. The dehydration rectifying tower kettle liquid enters a dehydration rectifying tower, the temperature of the tower kettle is 195 ℃, and the pressure of the tower kettle is 7kPaa. The kettle liquid of the deparasiting rectifying tower enters an evaporator, the temperature of the evaporator is 210 ℃, the pressure of the evaporator is 3kPaa, and TDA tar with 35 weight percent of m-toluenediamine is obtained from the bottom of the evaporator. 100g of TDA tar is dissolved by 300g of acetone, evenly mixed with 30g of 2-nitro-p-cresol, the pH of the reaction solution is adjusted to 4 by 5wt% sulfamic acid solution, stirred and reacted for 1.5 hours at 65 ℃, filtered, washed by water and dried to obtain a TDA tar disperse dye filter cake.
And (3) dyeing the polyester fiber cloth by using the dye under different dyeing bath conditions. The highest PH value is evaluated to be 8, the highest NaOH-resistant concentration is 3g/L, the dye-uptake is 95.2%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 3, the washing color fastness is fade 3, and the washing color fastness is stained 4.
Comparative example 2:
commercially available disperse red 97 dye is used for dyeing polyester fiber cloth under different dyeing bath conditions. The highest PH value is 5, the highest NaOH-resistant concentration is 0g/L, the dye-uptake is 95.4%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 4, the washing color fastness is fading 5, and the washing color fastness is staining 4.
Comparative example 3:
the polyester fiber cloth is dyed with commercially available disperse red 137 dye under different dye bath conditions. The highest PH value is 6, the highest NaOH-resistant concentration is 0g/L, the dye-uptake is 94.5%, the rubbing color fastness is dry 4, the wet rubbing color fastness is wet 5, the washing color fastness is fade 4, and the washing color fastness is stained 4.
TABLE 1 evaluation results of Performance of different dyes
The foregoing description is only of the preferred embodiments of the invention, and all changes and modifications that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (7)
1. A method for preparing a disperse dye by using TDA tar, which is characterized by comprising the following steps:
1) Dissolving TDA tar with a solvent I, uniformly mixing with a nitrophenol compound, regulating the pH of a reaction solution to 3-7 with an acid solution, stirring for reaction, carrying out suction filtration, washing with water, and drying to obtain a TDA tar disperse dye filter cake;
2) Dissolving the TDA tar disperse dye filter cake with a second solvent, adding glucomannan, adjusting the pH of the reaction solution to 3-7 with an acid solution, reacting, carrying out suction filtration, washing with water, and drying to obtain the disperse dye filter cake.
2. The method according to claim 1, wherein the TDA tar in step 1) is a tar obtained by concentrating a dinitrotoluene hydrogenation reaction solution;
preferably, the TDA tar is concentrated and then used as the raw material in the step 1), and the concentration adopts a dehydration rectifying tower, a depyrogenation rectifying tower or an evaporator refining mode, wherein the toluene diamine content is 20-50wt%, preferably 35-45wt%.
3. The method according to claim 1 or 2, wherein the nitrophenol compound of step 1) may be one or more of nitrocresols, amino-containing nitrophenols or fluoronitrophenols, preferably 2-nitro-p-cresol, 2, 6-dinitro-p-cresol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 2-fluoro-4-nitrophenol, 3-fluoro-4-nitrophenol, 4-fluoro-2-nitrophenol.
4. The method according to claim 1 or 2, wherein the acid for adjusting the pH of the reaction solution in step 1) is an inorganic acid or an organic acid, preferably one or more of sulfamic acid, oxalic acid, sulfuric acid, hydrochloric acid and phosphoric acid;
preferably, the mass ratio of TDA tar to solvent one is 1: 2-5, wherein the mass ratio of the TDA tar to the nitrophenol compound is 1:0.1 to 0.5;
preferably, the solvent one comprises one or more of alcohols, ketones, ethers or amides, preferably methanol, ethanol, acetone, tetrahydrofuran, 1, 4-dioxane, N-dimethylformamide, N-dimethylacetamide;
preferably, the pH of the reaction solution is 4 to 6; the reaction temperature is 40-80 ℃ and the reaction time is 0.5-2 h.
5. The method according to any one of claims 1-4, wherein the solvent two comprises alcohols, ketones or carboxylic acids, preferably one or more of methanol, ethanol, acetone, formic acid, acetic acid;
preferably, the acid in step 2) is an organic or inorganic acid, preferably one or more of sulfamic acid, sulfuric acid, hydrochloric acid and phosphoric acid;
preferably, the mass ratio of the TDA tar to the solvent II is 1: 2-5, wherein the mass ratio of the TDA tar to the glucomannan is 1:0.1 to 0.5;
preferably, the reaction in the step 2) is carried out under the ultrasonic condition, and the ultrasonic frequency is 50-125 Hz; the reaction temperature is 100-140 ℃ and the reaction time is 10-20 h;
more preferably, the pH of the reaction solution after the acid addition adjustment in the step 2) is 4 to 6.
6. Use of a disperse dye prepared by the process according to any one of claims 1 to 5 for dyeing textile materials.
7. The use according to claim 6, wherein the textile material is one or more of cotton, linen, silk, wool, leather, chemical fiber, and blends;
preferably, the dyeing condition PH is 2-14.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310000364.9A CN116082855A (en) | 2023-01-03 | 2023-01-03 | Method for preparing disperse dye by using TDA tar |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310000364.9A CN116082855A (en) | 2023-01-03 | 2023-01-03 | Method for preparing disperse dye by using TDA tar |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116082855A true CN116082855A (en) | 2023-05-09 |
Family
ID=86187852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310000364.9A Pending CN116082855A (en) | 2023-01-03 | 2023-01-03 | Method for preparing disperse dye by using TDA tar |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116082855A (en) |
-
2023
- 2023-01-03 CN CN202310000364.9A patent/CN116082855A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 何敬文等: "《药物合成反应》", vol. 1, 31 December 1995, 中国医药科技出版社, pages: 99 - 100 * |
| 宋航: "《制药分离工程》", vol. 1, 31 August 2011, 华东理工大学出版社, pages: 80 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Xiao et al. | Eco-friendly approaches for dyeing multiple type of fabrics with cationic reactive dyes | |
| WO2020048018A1 (en) | Azo dye dedicated for water-free dyeing of natural fiber in supercritical co 2 fluid, and preparation method therefor | |
| CN113292867B (en) | A kind of environment-friendly reactive dye and preparation method thereof | |
| CN112341838A (en) | Reactive dye, reactive dye ink, and preparation method and application thereof | |
| CN109233337B (en) | Black dye composition and dye product | |
| CN114085544B (en) | Disperse dyes with azo structure for dyeing polypropylene fiber and its preparation method and dyeing process | |
| Chen et al. | Study on coloration of silk based on coupling reaction with a diazonium compound | |
| CN116082855A (en) | Method for preparing disperse dye by using TDA tar | |
| CN111484751B (en) | Alkali washable sun-proof orange azo disperse dye and preparation method thereof | |
| CN106590013B (en) | The isomer mixture of CLT acid prepares acid dyes original powder and product | |
| CN109021614B (en) | A kind of high-fixation rate phthalocyanine azo-based two-chromophore reactive dyes and preparation method and application thereof | |
| CN111269429B (en) | Comb-type disperse dye dispersant and preparation method thereof | |
| CN111320882B (en) | Bright red reactive dye mixture and preparation method and application thereof | |
| CN108976844B (en) | Red reactive dye composition and dye product | |
| CN118273146B (en) | Polyester cotton disperse activity one-step one-bath dyeing process | |
| CN117304711B (en) | Reactive dye, preparation method and dyeing application thereof | |
| CN117402507B (en) | Dyeing methods for polyester and reactive dyes containing two diazo groups used | |
| CN107488358A (en) | Acid dye for low-temperature dyeing of wool and preparation method thereof | |
| WO2019223016A1 (en) | Blue anthraquinone active disperse dye and preparation method therefor | |
| CN113201234B (en) | Dark blue disperse dye composition with high washing fastness and application method thereof | |
| CN115725189B (en) | A disazo disperse dye and its synthesis method and application | |
| CN110878176B (en) | A kind of reactive dye compound and preparation method thereof | |
| CN116694100A (en) | Green-light black dye and preparation method and application thereof | |
| CN110746790B (en) | Brown vat dye using naphthalene tetracarboxylic acid as raw material, preparation method and application | |
| CN112409820B (en) | Reactive dye yellow brown and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |