CN105860570A - 一种卤代苯并噻唑-偶氮分散染料单体化合物及其制备方法和应用 - Google Patents
一种卤代苯并噻唑-偶氮分散染料单体化合物及其制备方法和应用 Download PDFInfo
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- CN105860570A CN105860570A CN201610216593.4A CN201610216593A CN105860570A CN 105860570 A CN105860570 A CN 105860570A CN 201610216593 A CN201610216593 A CN 201610216593A CN 105860570 A CN105860570 A CN 105860570A
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- compound
- benzothiazole
- azo dispersion
- monomer compound
- hydrogen
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- 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
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 239000000178 monomer Substances 0.000 title claims abstract description 24
- 239000000986 disperse dye Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000000975 dye Substances 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- LQOBMKYCRQDMTN-UHFFFAOYSA-N 3-(2-ethylphenyl)pentan-3-amine;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1C(N)(CC)CC LQOBMKYCRQDMTN-UHFFFAOYSA-N 0.000 claims description 3
- GHKHTBMTSUEBJD-UHFFFAOYSA-N 5,6-dichloro-1,3-benzothiazol-2-amine Chemical compound ClC1=C(Cl)C=C2SC(N)=NC2=C1 GHKHTBMTSUEBJD-UHFFFAOYSA-N 0.000 claims description 3
- 229920006221 acetate fiber Polymers 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 claims description 2
- 229920002972 Acrylic fiber Polymers 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 241000158728 Meliaceae Species 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 229920002334 Spandex Polymers 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- -1 diffusant Substances 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical group O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 239000004759 spandex Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- 238000007639 printing Methods 0.000 abstract description 8
- 238000000859 sublimation Methods 0.000 abstract description 6
- 230000008022 sublimation Effects 0.000 abstract description 6
- 239000004744 fabric Substances 0.000 abstract description 5
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 230000005012 migration Effects 0.000 abstract description 2
- 0 CC([C@](C=C1)N=Nc([s]c2c3)nc2cc(Br)c3Br)C=C1N(*)*=C Chemical compound CC([C@](C=C1)N=Nc([s]c2c3)nc2cc(Br)c3Br)C=C1N(*)*=C 0.000 description 7
- 238000004043 dyeing Methods 0.000 description 5
- 239000004218 Orcein Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 235000019248 orcein Nutrition 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229920004933 Terylene® Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- YKHFWFMWXBZUHK-UHFFFAOYSA-N 6,7-dichloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C(Cl)=C2SC(N)=NC2=C1 YKHFWFMWXBZUHK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000322338 Loeseliastrum Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000012932 acetate dye Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000012360 testing method 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
- C09B29/0074—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
- 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
-
- 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
- C09B67/008—Preparations of disperse dyes or solvent dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Description
升华牢度(级) | |
实施例2 | 5 |
实施例3 | 5 |
实施例4 | 4-5 |
实施例5 | 5 |
实施例6 | 5 |
对比例1 | 3 |
实施例 | K/S | dL | da | db | dE |
对比例1 | 14.36 | - | - | - | - |
实施例2 | 16.32 | 0.17 | 0.05 | -0.15 | 0.23 |
实施例3 | 15.20 | -0.07 | 0.15 | 0.17 | 0.23 |
实施例6 | 14.29 | -0.12 | 0.10 | 0.01 | 0.16 |
Claims (10)
Priority Applications (1)
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CN201610216593.4A CN105860570B (zh) | 2016-04-08 | 2016-04-08 | 一种卤代苯并噻唑-偶氮分散染料单体化合物及其制备方法和应用 |
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CN201610216593.4A CN105860570B (zh) | 2016-04-08 | 2016-04-08 | 一种卤代苯并噻唑-偶氮分散染料单体化合物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105860570A true CN105860570A (zh) | 2016-08-17 |
CN105860570B CN105860570B (zh) | 2018-07-31 |
Family
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Family Applications (1)
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CN201610216593.4A Active CN105860570B (zh) | 2016-04-08 | 2016-04-08 | 一种卤代苯并噻唑-偶氮分散染料单体化合物及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105860570B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113214185A (zh) * | 2021-05-11 | 2021-08-06 | 青海施丹弗化工有限责任公司 | 一种苯并噻唑类重氮偶合连续化反应的方法 |
CN117210028A (zh) * | 2023-11-09 | 2023-12-12 | 上海安诺其集团股份有限公司 | 艳蓝分散染料及制备方法和应用 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2326721A (en) * | 1941-01-15 | 1943-08-10 | Resinous Prod & Chemical Co | Cyanoethyl ether of tertiary amino alcohols |
DE1086369B (de) * | 1957-05-20 | 1960-08-04 | Ciba Geigy | Verfahren zur Herstellung von Monoazofarbstoffen |
US3686162A (en) * | 1969-01-24 | 1972-08-22 | Ciba Geigy Ag | Monoazo dyestuffs containing a benzthiazolyl radical |
CN101649129A (zh) * | 2009-07-30 | 2010-02-17 | 浙江龙盛染料化工有限公司 | 一种适用于碱性染色的分散染料组合物 |
CN104479393A (zh) * | 2014-11-18 | 2015-04-01 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的大红色分散染料及其制备方法 |
CN104479407A (zh) * | 2014-11-19 | 2015-04-01 | 蓬莱嘉信染料化工股份有限公司 | 黄色分散染料组合物及其制备方法和应用 |
CN104727164A (zh) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | 一种可碱性染色的分散染料混合物的应用 |
CN104725895A (zh) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | 一种可碱性染色的分散染料混合物的制备方法 |
CN105111787A (zh) * | 2015-07-30 | 2015-12-02 | 杭州吉华江东化工有限公司 | 一种分散染料混合物及其应用 |
-
2016
- 2016-04-08 CN CN201610216593.4A patent/CN105860570B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2326721A (en) * | 1941-01-15 | 1943-08-10 | Resinous Prod & Chemical Co | Cyanoethyl ether of tertiary amino alcohols |
DE1086369B (de) * | 1957-05-20 | 1960-08-04 | Ciba Geigy | Verfahren zur Herstellung von Monoazofarbstoffen |
US3686162A (en) * | 1969-01-24 | 1972-08-22 | Ciba Geigy Ag | Monoazo dyestuffs containing a benzthiazolyl radical |
CN101649129A (zh) * | 2009-07-30 | 2010-02-17 | 浙江龙盛染料化工有限公司 | 一种适用于碱性染色的分散染料组合物 |
CN104727164A (zh) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | 一种可碱性染色的分散染料混合物的应用 |
CN104725895A (zh) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | 一种可碱性染色的分散染料混合物的制备方法 |
CN104479393A (zh) * | 2014-11-18 | 2015-04-01 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的大红色分散染料及其制备方法 |
CN104479407A (zh) * | 2014-11-19 | 2015-04-01 | 蓬莱嘉信染料化工股份有限公司 | 黄色分散染料组合物及其制备方法和应用 |
CN105111787A (zh) * | 2015-07-30 | 2015-12-02 | 杭州吉华江东化工有限公司 | 一种分散染料混合物及其应用 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113214185A (zh) * | 2021-05-11 | 2021-08-06 | 青海施丹弗化工有限责任公司 | 一种苯并噻唑类重氮偶合连续化反应的方法 |
CN117210028A (zh) * | 2023-11-09 | 2023-12-12 | 上海安诺其集团股份有限公司 | 艳蓝分散染料及制备方法和应用 |
CN117210028B (zh) * | 2023-11-09 | 2024-01-30 | 上海安诺其集团股份有限公司 | 艳蓝分散染料及制备方法和应用 |
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Address after: 312073 new second village, Ma On Zhen, Keqiao District, Shaoxing, Zhejiang Patentee after: Zhejiang Wanfeng Chemical Co., Ltd Address before: 312073 new second village, Ma On Zhen, Keqiao District, Shaoxing, Zhejiang Patentee before: Zhejiang Wanfeng Chemical Co., Ltd. |