CN109054429A - 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 - Google Patents
一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN109054429A CN109054429A CN201810737156.6A CN201810737156A CN109054429A CN 109054429 A CN109054429 A CN 109054429A CN 201810737156 A CN201810737156 A CN 201810737156A CN 109054429 A CN109054429 A CN 109054429A
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- fastness
- azo dye
- acetamide group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 239000000987 azo dye Substances 0.000 title claims abstract description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000000975 dye Substances 0.000 claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 23
- 238000004043 dyeing Methods 0.000 claims abstract description 16
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- -1 polypropylene Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229920004933 Terylene® Polymers 0.000 claims description 3
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 3
- 229920002972 Acrylic fiber Polymers 0.000 claims description 2
- 229920006052 Chinlon® Polymers 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 229920002334 Spandex Polymers 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 239000004759 spandex Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 abstract description 4
- 230000008022 sublimation Effects 0.000 abstract description 4
- 239000004753 textile Substances 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 210000004243 sweat Anatomy 0.000 abstract 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 10
- 239000000986 disperse dye Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 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 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
标准样 | 批次样 | o.w.f(%) | 光源 | dL* | da* | db* | dC* |
分散红60 | 实施例1 | 2.5 | D65/10 | -0.06 | -0.05 | 0.11 | -0.06 |
分散红60 | 实施例2 | 2.5 | D65/10 | 0.08 | -0.10 | 0.01 | -0.10 |
分散红60 | 实施例3 | 2.5 | D65/10 | 0.09 | -0.16 | 0.06 | -0.02 |
分散红60 | 实施例4 | 2.5 | D65/10 | 0.15 | -0.09 | 0.05 | -0.07 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201810737156.6A CN109054429B (zh) | 2018-07-06 | 2018-07-06 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201810737156.6A CN109054429B (zh) | 2018-07-06 | 2018-07-06 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
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CN109054429A true CN109054429A (zh) | 2018-12-21 |
CN109054429B CN109054429B (zh) | 2020-06-09 |
Family
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CN201810737156.6A Active CN109054429B (zh) | 2018-07-06 | 2018-07-06 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
Country Status (1)
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CN (1) | CN109054429B (zh) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980634A (en) * | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
CN1491259A (zh) * | 2001-02-07 | 2004-04-21 | �������⻯ѧƷ�ع�����˾ | 邻苯二甲酰亚胺基偶氮染料、其制备方法及其应用 |
CN1711319A (zh) * | 2002-11-11 | 2005-12-21 | 西巴特殊化学品控股有限公司 | 邻苯二甲酰亚胺-偶氮染料,其制备方法和其应用 |
KR20130130966A (ko) * | 2012-05-23 | 2013-12-03 | 공명도 | 고 습윤견뢰도의 흑색 및 네이비블루 분산염료 조성물 |
CN104520498A (zh) * | 2012-07-27 | 2015-04-15 | 亨斯迈先进材料(瑞士)有限公司 | 分散偶氮染料、其制备方法及其用途 |
-
2018
- 2018-07-06 CN CN201810737156.6A patent/CN109054429B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980634A (en) * | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
CN1491259A (zh) * | 2001-02-07 | 2004-04-21 | �������⻯ѧƷ�ع�����˾ | 邻苯二甲酰亚胺基偶氮染料、其制备方法及其应用 |
CN1711319A (zh) * | 2002-11-11 | 2005-12-21 | 西巴特殊化学品控股有限公司 | 邻苯二甲酰亚胺-偶氮染料,其制备方法和其应用 |
KR20130130966A (ko) * | 2012-05-23 | 2013-12-03 | 공명도 | 고 습윤견뢰도의 흑색 및 네이비블루 분산염료 조성물 |
CN104520498A (zh) * | 2012-07-27 | 2015-04-15 | 亨斯迈先进材料(瑞士)有限公司 | 分散偶氮染料、其制备方法及其用途 |
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Publication number | Publication date |
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CN109054429B (zh) | 2020-06-09 |
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Address after: 312073 new second village, Ma On Zhen, Keqiao District, Shaoxing, Zhejiang Applicant after: Zhejiang Wanfeng Chemical Co.,Ltd. Address before: 312073 new second village, Ma On Zhen, Keqiao District, Shaoxing, Zhejiang Applicant before: ZHEJIANG WANFENG CHEMICAL Co.,Ltd. |
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Denomination of invention: A azo dye compound containing an acetamide group and its preparation method and application Effective date of registration: 20230822 Granted publication date: 20200609 Pledgee: Zhejiang Shaoxing Ruifeng Rural Commercial Bank Co.,Ltd. Binhai sub branch Pledgor: Zhejiang Wanfeng Chemical Co.,Ltd. Registration number: Y2023980053262 |