CN116694103A - 一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用 - Google Patents
一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用 Download PDFInfo
- Publication number
- CN116694103A CN116694103A CN202310691315.4A CN202310691315A CN116694103A CN 116694103 A CN116694103 A CN 116694103A CN 202310691315 A CN202310691315 A CN 202310691315A CN 116694103 A CN116694103 A CN 116694103A
- Authority
- CN
- China
- Prior art keywords
- disperse dye
- pyrazolone
- benzothiazole
- dye
- solution
- 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 73
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 amino pyrazolone benzothiazole Chemical compound 0.000 claims abstract description 38
- 238000004043 dyeing Methods 0.000 claims abstract description 32
- 229920000742 Cotton Polymers 0.000 claims abstract description 20
- 239000012954 diazonium Substances 0.000 claims abstract description 17
- 239000000975 dye Substances 0.000 claims abstract description 11
- 229920000728 polyester Polymers 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 9
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006149 azo coupling reaction Methods 0.000 claims abstract description 8
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000008878 coupling Effects 0.000 claims abstract description 7
- 238000010168 coupling process Methods 0.000 claims abstract description 7
- 238000000967 suction filtration Methods 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 27
- 239000000835 fiber Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000001989 diazonium salts Chemical class 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 229920003043 Cellulose fiber Polymers 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 235000009120 camo Nutrition 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 235000005607 chanvre indien Nutrition 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 239000011487 hemp Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 2
- 238000009979 jig dyeing Methods 0.000 abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000004744 fabric Substances 0.000 description 20
- 238000005406 washing Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229940079101 sodium sulfide Drugs 0.000 description 2
- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000004045 reactive dyeing Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
-
- 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
-
- 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
- D06P1/38—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 reactive dyes
- D06P1/382—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 reactive dyes reactive group directly attached to heterocyclic group
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/043—Material containing basic nitrogen containing amide groups using dispersed 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/10—Material containing basic nitrogen containing amide groups using reactive 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
- D06P3/528—Polyesters using reactive 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
-
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6033—Natural or regenerated cellulose using dispersed dyes
- D06P3/6041—Natural or regenerated cellulose using dispersed dyes using specified 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
- D06P3/8252—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and reactive dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Abstract
本发明公开一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用，属于染色技术领域。本发明首先对2‑氨基‑6‑硝基苯并噻唑重氮化，所得重氮化溶液与3‑甲基‑1‑苯基‑5‑吡唑啉酮的偶合得到重氮偶合产物；对合成的重氮偶合产物进行硝基还原得到氨基吡唑啉酮苯并噻唑分散染料，最后，在氨基吡唑啉酮苯并噻唑分散染料上接枝均三嗪活性基团；抽滤、烘干，得到吡唑啉酮苯并噻唑均三嗪活性分散染料。本发明制备的分散染料具有较高的分子量，从而提高了染料的上染率和固色率，该分散染料和活性分散染料适用于在超临界CO2体系下对涤/棉65/35的同色拼染，具有很大的开发应用潜力。
Description
技术领域
本发明属于染色技术领域，具体涉及一类具有偶氮苯并噻唑结构的分散染料、制备方法及其在超临界二氧化碳同色拼染中的应用。
背景技术
涤棉纤维兼具了涤和棉两种纤维的优良特性，其中棉纤维的存在导致常规分散染料无法对其进行有效上染，因此，研究开发可用于涤棉纤维染色的新的分散染料显得尤为重要。此外，涤棉纤维的传统染色方法以水为介质，通常采用分散染料和活性染料进行两浴法染色，染色工艺复杂，用时长，耗能多，且用水量大，污水处理复杂，对环境造成较重影响。
芳香族伯胺和亚硝酸作用(在强酸介质下)可以生成重氮盐，重氮盐与芳胺在中性或弱酸性介质中能够发生偶联反应，然而通过重氮偶合反应制备具有偶氮苯并噻唑结构的分散染料的相关研究还未见报道。
发明内容
鉴于此，本发明的目的是提供一类具有偶氮苯并噻唑结构的分散染料、制备方法及其在超临界二氧化碳同色拼染中的应用，显著提高涤棉混纺织物染色效果，实现涤棉混纺织物的一浴法无助剂染色。
为了实现本发明的目的，本发明提供如下技术方案：
本发明提供一类具有偶氮苯并噻唑结构的分散染料，所述的染料包括氨基吡唑啉酮苯并噻唑分散染料和吡唑啉酮苯并噻唑均三嗪活性分散染料，氨基吡唑啉酮苯并噻唑分散染料的结构式如式I所示，吡唑啉酮苯并噻唑均三嗪活性分散染料的结构式如式II所示：
本发明另一方面提供上述的具有偶氮苯并噻唑结构的分散染料的制备方法，包括以下步骤：
(1)2-氨基-6-硝基苯并噻唑的重氮化：将2-氨基-6-硝基苯并噻唑溶解在混酸溶液中，冷却至0-5℃，加入HNO2，搅拌反应1-5h，得到一种澄清的淡黄色重氮盐III溶液；
(2)重氮盐III与3-甲基-1-苯基-5-吡唑啉酮的偶合：将3-甲基-1-苯基-5-吡唑啉酮溶于碱性溶液中，滴加重氮盐III溶液，将pH值调节到酸性，在0-5℃下反应2-5h，抽滤，干燥，得到重氮偶合产物IV；
(3)重氮偶合产物IV的硝基还原：将重氮偶合产物IV完全溶解于醇溶液中，在40～80℃下搅拌，逐滴加入溶有硫化钠和碳酸氢钠的水溶液，回流反应2-5h，冷却，抽滤，得到分散染料I；
(4)分散染料I接枝均三嗪活性基团：将分散染料I加入有机溶剂和水的混合溶液中，0-5℃下搅拌至完全溶解，滴加含有1～2倍当量三聚氯氰的有机溶剂，调节pH至6.5～7.5，搅拌反应2～5h，得到活性分散染料II；
基于上述技术方案，进一步地，步骤(1)中所述的混酸溶液是由体积比为2:1～1:2的浓硫酸和浓磷酸混合而成；HNO2与2-氨基-6-硝基苯并噻唑的摩尔比为2:1～1:1。
基于上述技术方案，进一步地，步骤(2)中碱性溶液为NaOH溶液、KOH溶液中的一种或两种的混合溶液；3-甲基-1-苯基-5-吡唑啉酮与重氮盐III的摩尔比为1:1。
基于上述技术方案，进一步地，步骤(3)中醇溶液为甲醇、乙醇、丙醇中的一种或两种以上的混合溶液；硫化钠、碳酸氢钠与重氮偶合产物IV的摩尔比均为2:1～1:1。
基于上述技术方案，进一步地，步骤(4)中所述的有机溶剂所述的有机溶剂包括二氧六环；有机溶剂与水的体积比为5:1～2:1。
基于上述技术方案，进一步地，步骤(2)和步骤(4)中所述烘干的条件为：40～80℃烘干10～24h。
本发明还提供所述的具有偶氮苯并噻唑结构的分散染料在超临界CO2无水染色中的应用。
基于上述技术方案，进一步地，以超临界CO2流体为染色介质，采用所述的具有偶氮苯并噻唑结构的分散染料中的一种或两种组合对待染纺织品进行染色。
基于上述技术方案，进一步地，待染纺织品为纤维素纤维、蛋白质纤维、化学纤维中的一种或两种以上形成的混纺织物。
基于上述技术方案，进一步地，所述纤维素纤维为棉纤维、麻纤维，所述蛋白质纤维为毛纤维、丝纤维，所述化学纤维为涤纶。
基于上述技术方案，进一步地，所述染色具体过程为：将0.5-2.5％(o.w.f)的染料置于染料釜内，再将待染纺织品置于染色釜内，于80-150℃、16-25MPa的条件下染色40-150min。
与现有技术相比，本发明的有益效果为：
1.本发明提供的偶氮苯并噻唑型活性分散染料可以满足对涤纶、棉的反应着色要求，具有良好的染色性能，染色产品耐洗色牢度和耐摩擦色牢度可达到4-5级以上。
2.本发明合成的分散染料与其对应的活性分散染料具有同源性，可在超临界CO2体系中对混纺织物进行同色拼染。在对涤/棉65/35进行拼染时，满足对涤棉的反应着色要求，具有良好的染色性能，染色产品耐洗色牢度和耐摩擦色牢度可达到4-5级。
附图说明
图1为氨基吡唑啉酮苯并噻唑分散染料(B1)、吡唑啉酮苯并噻唑均三嗪活性分散染料(B2)的紫外吸收光谱。
图2为氨基吡唑啉酮苯并噻唑分散染料(B1)、吡唑啉酮苯并噻唑均三嗪活性分散染料(B2)的红外光谱。
图3为氨基吡唑啉酮苯并噻唑分散染料核磁氢谱图。
图4为氨基吡唑啉酮苯并噻唑分散染料核磁碳谱图。
图5为吡唑啉酮苯并噻唑均三嗪活性分散染料核磁氢谱图。
图6为吡唑啉酮苯并噻唑均三嗪活性分散染料核磁碳谱图。
具体实施方式
本发明的目的是通过以下技术方案来实现：氨基吡唑啉酮苯并噻唑分散染料、吡唑啉酮苯并噻唑均三嗪活性分散染料的合成。
实施例1
本实施例提供一种具有偶氮苯并噻唑结构的分散染料的合成方法，包括以下步骤：
(1)将2-氨基-6-硝基苯并噻唑(2.25g，0.01mol)溶解在含有11mL硫酸(H2SO4，98％)和17mL磷酸(H3PO4，80％)的混合溶液中；将混合溶液加热至78℃，搅拌3h，将亮黄色溶液冷却至0-5℃，此后，将NaNO2(0.69g，0.01mol)溶解在5mL H2SO4(98％)中以生成HNO2，将其逐滴添加到上述混合物中，搅拌反应3h，并通过添加尿素去除多余的HNO2，并使用淀粉KI试纸检测，直至淀粉KI试纸1-2s内不变色，得到一种澄清的淡黄色重氮盐溶液；
(2)将3-甲基-1-苯基-5-吡唑啉酮(1.74g，0.01mol)溶于NaOH溶液(50mL，0.8mol/L)中，缓慢添加重氮盐溶液，通过添加30％(w/v)NaOH溶液将混合物的pH值调节到弱酸性，在0-5℃下反应2.5-3h，抽滤得到固体产物，在60℃真空干燥箱中干燥24h，得到重氮偶合染料母体1.68g(75％)；合成路线如下：
(3)取重氮偶合染料母体(3.8g，0.01mol)完全溶解于乙醇中，在60℃下搅拌，将九水硫化钠(2.4g，0.01mol)和碳酸氢钠(0.88g，0.01mol)溶于10mL水中，逐滴加入到上述溶液中，回流反应3-4h，得到氨基吡唑啉酮苯并噻唑分散染料；合成路线如下：
上述方法制得的氨基吡唑啉酮苯并噻唑分散染料的紫外吸收光谱、红外光谱、核磁氢谱图和核磁碳谱图分别如图1-4所示，表明成功合成了氨基吡唑啉酮苯并噻唑分散染料。
实施例2
取实施例1中的氨基吡唑啉酮苯并噻唑分散染料(1.752g，0.005mol)溶于146mL二氧六环中，加入48mL水，0-5℃下搅拌15min至完全溶解，将三聚氯氰(0.92g，0.005mol)溶解于40mL二氧六环中，滴加到上述溶液中，通过Na2CO3调节pH＝7，冰浴条件下快速搅拌反应3h，得到吡唑啉酮苯并噻唑均三嗪活性分散染料；合成路线如下：
上述方法制得的吡唑啉酮苯并噻唑均三嗪活性分散染料的紫外吸收光谱、红外光谱、分别如图1-2所示，由图2可知，合成的活性分散染料在600-900cm-1处出现了苯环上C-H的面外弯曲振动峰，在1400-1600cm-1间出现了苯环的骨架外振动峰，在800cm-1处出现了C-Cl的伸缩振动吸收峰，3400cm-1左右出现了-NH的伸缩振动吸收峰，表明分散染料母体成功接枝二氯均三嗪活性基团生成活性分散染料；吡唑啉酮苯并噻唑均三嗪活性分散染料的核磁氢谱图和核磁碳谱图分别如图3-4所示，进一步表明成功合成了吡唑啉酮苯并噻唑均三嗪活性分散染料。
实施例3
一种涤纶织物超临界CO2无水染色方法：将2％(o.w.f)的氨基吡唑啉酮苯并噻唑分散染料与待染涤纶织物置于釜体中，以超临界CO2流体为染色介质，于120℃、24MPa的条件下对待染色60min。染色涤纶织物K/S值可达15.96，耐水洗色牢度和耐摩擦色牢度为4-5级。
实施例4
一种棉织物超临界CO2无水染色方法：将1.5％(o.w.f)的吡唑啉酮苯并噻唑均三嗪活性分散染料与待染棉织物置于釜体中，以超临界CO2流体为染色介质，于120℃、24MPa的条件下对待染色60min。染色棉织物K/S值可达7.48，耐水洗色牢度和耐摩擦色牢度为4级。
实施例5
一种涤/棉65/35织物的超临界CO2无水拼染方法：将质量比为1：1的2.5％(o.w.f)的氨基吡唑啉酮苯并噻唑分散染料、吡唑啉酮苯并噻唑均三嗪活性分散染料与待染涤/棉65/35织物置于釜体中，以超临界CO2流体为染色介质，于120℃、24MPa的条件下对待染色60min。染色涤棉织物K/S值可达9，耐水洗色牢度和耐摩擦色牢度为4-5级。
实施例6
一种麻织物超临界CO2无水染色方法：将1.5％(o.w.f)的吡唑啉酮苯并噻唑均三嗪活性分散染料与待染麻织物置于釜体中，以超临界CO2流体为染色介质，于120℃、24MPa的条件下对待染色60min。染色麻织物K/S值可达8.5，耐水洗色牢度和耐摩擦色牢度为4-5级。
实施例7
一种毛织物超临界CO2无水染色方法：将1.5％(o.w.f)的吡唑啉酮苯并噻唑均三嗪活性分散染料与待染毛织物置于釜体中，以超临界CO2流体为染色介质，于120℃、24MPa的条件下对待染色60min。染色毛织物K/S值可达10.3，耐水洗色牢度和耐摩擦色牢度为4-5级。
实施例8
一种丝织物超临界CO2无水染色方法：将1.5％(o.w.f)的吡唑啉酮苯并噻唑均三嗪活性分散染料与待染丝织物置于釜体中，以超临界CO2流体为染色介质，于120℃、24MPa的条件下对待染色60min。染色丝织物K/S值可达8.25，耐水洗色牢度和耐摩擦色牢度为4-5级。
Claims (10)
1.一类具有偶氮苯并噻唑结构的分散染料，其特征在于，所述的染料包括氨基吡唑啉酮苯并噻唑分散染料和吡唑啉酮苯并噻唑均三嗪活性分散染料，氨基吡唑啉酮苯并噻唑分散染料的结构式如式I所示，吡唑啉酮苯并噻唑均三嗪活性分散染料的结构式如式II所示：
2.权利要求1所述的具有偶氮苯并噻唑结构的分散染料的制备方法，其特征在于，包括以下步骤：
(1)2-氨基-6-硝基苯并噻唑的重氮化：将2-氨基-6-硝基苯并噻唑溶解在混酸溶液中，冷却至0-5℃，加入HNO2，搅拌反应1-5h，得到一种澄清的淡黄色重氮盐III溶液；
(2)重氮盐III与3-甲基-1-苯基-5-吡唑啉酮的偶合：将3-甲基-1-苯基-5-吡唑啉酮溶于碱性溶液中，滴加重氮盐III溶液，将pH值调节到酸性，在0-5℃下反应2-5h，抽滤，干燥，得到重氮偶合产物IV；
(3)重氮偶合产物IV的硝基还原：将重氮偶合产物IV完全溶解于醇溶液中，在40～80℃下搅拌，逐滴加入溶有硫化钠和碳酸氢钠的水溶液，回流反应2-5h，冷却，抽滤，得到分散染料I；
(4)分散染料I接枝均三嗪活性基团：将分散染料I加入有机溶剂和水的混合溶液中，0-5℃下搅拌至完全溶解，滴加含有1～2倍当量三聚氯氰的有机溶剂，调节pH至6.5～7.5，搅拌反应2～5h，得到活性分散染料II；
3.根据权利要求2所述的制备方法，其特征在于，步骤(1)中所述的混酸溶液是由体积比为2:1～1:2的浓硫酸和浓磷酸混合而成；HNO2与2-氨基-6-硝基苯并噻唑的摩尔比为2:1～1:1。
4.根据权利要求2所述的制备方法，其特征在于，步骤(2)中碱性溶液为NaOH溶液、KOH溶液中的一种或两种的混合溶液；3-甲基-1-苯基-5-吡唑啉酮与重氮盐III的摩尔比为1:1。
5.根据权利要求2所述的制备方法，其特征在于，步骤(3)中醇溶液为甲醇、乙醇、丙醇中的一种或两种以上的混合溶液；硫化钠、碳酸氢钠与重氮偶合产物IV的摩尔比均为2:1～1:1。
6.根据权利要求2所述的制备方法，其特征在于，步骤(4)中所述的有机溶剂所述的有机溶剂包括二氧六环；有机溶剂与水的体积比为5:1～2:1。
7.权利要求1所述的具有偶氮苯并噻唑结构的分散染料在超临界CO2无水染色中的应用，其特征在于，以超临界CO2流体为染色介质，采用所述的具有偶氮苯并噻唑结构的分散染料中的一种或两种组合对待染纺织品进行染色。
8.根据权利要求7所述的应用，其特征在于，待染纺织品为纤维素纤维、蛋白质纤维、化学纤维中的一种或两种以上形成的混纺织物。
9.根据权利要求8所述的应用，其特征在于，所述纤维素纤维为棉纤维、麻纤维，所述蛋白质纤维为毛纤维、丝纤维，所述化学纤维为涤纶。
10.根据权利要求7所述的应用，其特征在于，所述染色具体过程为：将0.5-2.5％(o.w.f)的染料置于染料釜内，再将待染纺织品置于染色釜内，于80-150℃、16-25MPa的条件下染色40-150min。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310691315.4A CN116694103A (zh) | 2023-06-12 | 2023-06-12 | 一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310691315.4A CN116694103A (zh) | 2023-06-12 | 2023-06-12 | 一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116694103A true CN116694103A (zh) | 2023-09-05 |
Family
ID=87833540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310691315.4A Pending CN116694103A (zh) | 2023-06-12 | 2023-06-12 | 一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116694103A (zh) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2832764A (en) * | 1955-03-31 | 1958-04-29 | Basf Ag | Production of azo dyestuffs |
| US3468873A (en) * | 1966-04-20 | 1969-09-23 | Hoechst Ag | Water-soluble thiazolyl monoazo-dyestuffs |
| US4962040A (en) * | 1986-06-04 | 1990-10-09 | Bayer Aktiengesellschaft | 2-hydrazono-4,6-dinitrobenzthiazolones useful to form dyestuffs and as color formers for detecting peroxide |
| CN105732248A (zh) * | 2014-12-11 | 2016-07-06 | 仲恺农业工程学院 | 一种硝基苯基复杂分子中的硝基还原成氨基的方法 |
| CN106467676A (zh) * | 2015-08-18 | 2017-03-01 | 香港纺织及成衣研发中心有限公司 | 用于超临界二氧化碳流体染色的棉纤维染料及其合成方法 |
| CN107057401A (zh) * | 2017-04-21 | 2017-08-18 | 苏州大学 | 基于蒽醌的二氯均三嗪型活性分散染料及其制备方法 |
| CN107892823A (zh) * | 2017-10-20 | 2018-04-10 | 大连工业大学 | 一类具有偶氮苯并噻唑结构的适合于超临界二氧化碳无水羊毛染色的分散染料及其制备方法 |
| CN114163838A (zh) * | 2021-11-12 | 2022-03-11 | 大连工业大学 | 一种超临界co2染色用黄色活性分散染料及其制备方法和应用 |
-
2023
- 2023-06-12 CN CN202310691315.4A patent/CN116694103A/zh active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2832764A (en) * | 1955-03-31 | 1958-04-29 | Basf Ag | Production of azo dyestuffs |
| US3468873A (en) * | 1966-04-20 | 1969-09-23 | Hoechst Ag | Water-soluble thiazolyl monoazo-dyestuffs |
| US4962040A (en) * | 1986-06-04 | 1990-10-09 | Bayer Aktiengesellschaft | 2-hydrazono-4,6-dinitrobenzthiazolones useful to form dyestuffs and as color formers for detecting peroxide |
| CN105732248A (zh) * | 2014-12-11 | 2016-07-06 | 仲恺农业工程学院 | 一种硝基苯基复杂分子中的硝基还原成氨基的方法 |
| CN106467676A (zh) * | 2015-08-18 | 2017-03-01 | 香港纺织及成衣研发中心有限公司 | 用于超临界二氧化碳流体染色的棉纤维染料及其合成方法 |
| CN107057401A (zh) * | 2017-04-21 | 2017-08-18 | 苏州大学 | 基于蒽醌的二氯均三嗪型活性分散染料及其制备方法 |
| CN107892823A (zh) * | 2017-10-20 | 2018-04-10 | 大连工业大学 | 一类具有偶氮苯并噻唑结构的适合于超临界二氧化碳无水羊毛染色的分散染料及其制备方法 |
| CN114163838A (zh) * | 2021-11-12 | 2022-03-11 | 大连工业大学 | 一种超临界co2染色用黄色活性分散染料及其制备方法和应用 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0021105B1 (en) | Reactive dyes, process for their preparation and their use for dyeing cellulose fibers | |
| EP0022265B1 (en) | Reactive bisazo dyes, a process for their production and their use for dyeing cellulose fibers and cellulosic textiles | |
| CN109971208B (zh) | 一种活性染料化合物及其制备方法和应用 | |
| CN114163838B (zh) | 一种超临界co2染色用黄色活性分散染料及其制备方法和应用 | |
| US3363972A (en) | Process for dyeing and printing natural nitrogen-containing fibrous materials | |
| US3920386A (en) | Process for the single-bath dyeing of cellulose fibers or mixtures thereof with synthetic fibers with water-insoluble azo dyestuffs produced on the fiber by the exhaustion method | |
| CN105754376A (zh) | 一种偶合组分为n,n-二乙基间氨基苯胺的阳离子活性染料及其制备方法和应用 | |
| JPH0478753B2 (zh) | ||
| Chen et al. | Study on coloration of silk based on coupling reaction with a diazonium compound | |
| US3788801A (en) | Process for the preparation of fast dyeings and prints on fibrous matprocess for the preparation of fast dyeings and prints on fibrous material containing hydroxyl groups or nitrogen | |
| CN116694103A (zh) | 一类具有偶氮苯并噻唑结构的分散染料及其制备方法和应用 | |
| KR100255333B1 (ko) | 모노아조 화합물 및 이 화합물을 사용하는 섬유재료의 염색 또는 날염방법 | |
| CN109796786B (zh) | 一种复合型鲜艳红色活性染料及其制备方法与应用 | |
| CN116694102A (zh) | 具有n,n-二乙基-6-氨基苯并噻唑结构的偶氮型分散染料及其制备方法和应用 | |
| JPS6221904B2 (zh) | ||
| JPS5818472B2 (ja) | セルロ−ズ系繊維の染色法 | |
| CN105733300A (zh) | 一种偶合组分为苯胺的阳离子活性染料及其制备方法和应用 | |
| US3325242A (en) | Process for dyeing and printing with reactive dyestuffs | |
| KR960000173B1 (ko) | 주홍색 모노아조 화합물, 그 제조방법 및 그를 사용한 섬유의 염색 또는 날염방법 | |
| US3211513A (en) | Process for dyeing and printing reactive dyestuffs | |
| JP2534909B2 (ja) | 反応性染料の新しい製法 | |
| Ali et al. | Synthesis and application of new ureido reactive dyes | |
| CN116218254B (zh) | 一种艳红色活性染料及其制备方法 | |
| US4118186A (en) | Process for the fixation of organic dyestuffs on materials having a fibrous structure | |
| CN116694101A (zh) | 一种改性蒽醌型活性分散染料及其制备方法和应用 |
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 |