CN108727864B - 一种含氟活性荧光染料 - Google Patents
一种含氟活性荧光染料 Download PDFInfo
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 5
- 239000011737 fluorine Substances 0.000 title claims abstract description 5
- 239000004744 fabric Substances 0.000 claims description 11
- 239000000835 fiber Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 2
- 239000000985 reactive dye Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 238000002360 preparation method Methods 0.000 abstract description 5
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- -1 filtering is added Chemical compound 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- 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
- C09B62/043—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 containing two or more triazine rings linked together by a non-chromophoric link
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- 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
- C09B62/046—Specific dyes not provided for in group C09B62/06 - C09B62/10
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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Abstract
本发明公开了一种1,8‑萘酰亚胺类含氟活性荧光染料。该活性荧光染料是具有如下通式（Ⅰ）结构的化合物。本发明提供的活性荧光染料制备工艺简单，荧光效果好，产品溶解度高，色泽鲜艳，应用性能优异，使用方便，是一种适用性强的活性荧光染料。
Description
技术领域
本发明涉及一种荧光染料，特别是涉及一种活性荧光染料的制备和用途。
背景技术
荧光染料的视觉效果既包括对可见光选择吸收后产生的颜色，又包括它们发射出来的荧光。它属于一种功能性染料，既具有常规染料的着色性能，又能发射出荧光，使得织物的饱和度和鲜艳度提高。目前，市场上的纺织品用荧光染料大多数是分散染料和阳离子染料，主要用于涤纶和腈纶的染色，而适用于毛织物染色的活性类荧光染料品种却鲜有报道。
1,8-萘酰亚胺类荧光染料是一类重要的功能染料,目前已广泛用于染料、颜料和荧光增白剂。
发明内容
本发明所要解决的技术问题是提供一种1,8-萘酰亚胺结构的活性荧光染料，可以对棉和黏胶纤维、纱线和织物进行染色，用来制备荧光纤维、纱线和织物。具体地，本发明提供了下式（Ⅰ）的化合物：
（Ⅰ）
该化合物合成方法包括如下步骤：
A、化合物（Ⅱ）的合成
（Ⅱ）
250ml三口瓶中加入0.2mol4-氨基-3,6-二磺基-1,8-萘醛酸酐二钾盐，0.6mol对苯二胺，适量水，加热回流至反应完全。冷却至室温，加入适量醋酸钾盐析，过滤，乙醇洗去醋酸钾，干燥得产品（Ⅱ）。
B、化合物（Ⅲ）的合成
（Ⅲ）
化合物（Ⅱ）与三聚氟氰按照摩尔比1：2～1：3在水溶液中进行反应，先将化合物（Ⅱ）到水中，维持温度0～3℃。然后滴入三聚氟氰和丙酮的混合液，滴加时间40～60min，搅拌反应1～3h，反应完后按体积20～25%加食盐盐析，再搅拌1～2h，压滤。到得到化合物（Ⅲ）。
C、化合物（Ⅰ）的合成
化合物（Ⅲ）与对苯二胺按照摩尔比2：0.9～2：1在水溶液中进行反应，滴加NaOH水溶液保持反应液pH=6.5，30～40℃搅拌反应5～7h，反应完后盐析，压滤，烘干，粉碎，到得到化合物（Ⅰ）。
该染料对纤维染色工艺为：化合物（Ⅰ）用量0.05～10%(o.w.f，对织物重)，浴比1：20～1：100，室温入染，加元明粉5～20%(o.w.f，对织物重)，2℃/min升温到40～60℃，加纯碱5～20%(o.w.f，对织物重)，保温40～60min，染毕，水洗、皂洗、水洗。
本发明所生产的活性染料，含有双一氟三嗪反应基，该反应基团可以与纤维素纤维上的羟基反应形成共价键，取代反应固着在纤维上, 具有良好的染色性能。
具体实施方式
上面对本发明活性荧光染料的结构、制备方法及应用进行了说明，下面将通过实施例对本发明工作进一步的说明。
实施例1：
本实施例提供了式（Ⅰ）化合物的制备方法：
具体制备方法如下：
该化合物合成方法包括如下步骤：
A、化合物（Ⅱ）的合成
250ml三口瓶中加入0.2mol4-氨基-3,6-二磺基-1,8-萘醛酸酐二钾盐，0.6mol对苯二胺，适量水，加热回流至反应完全。冷却至室温，加入适量醋酸钾盐析，过滤，乙醇洗去醋酸钾，干燥得产品（Ⅱ）。
B、化合物（Ⅲ）的合成
化合物（Ⅱ）与三聚氟氰按照摩尔比1：3在水溶液中进行反应，先将化合物（Ⅱ）到水中，维持温度0～3℃。然后滴入三聚氟氰和丙酮的混合液，滴加时间40～60min，搅拌反应2h，反应完后按体积25%加食盐盐析，再搅拌1h，压滤。到得到化合物（Ⅲ）。
C、化合物（Ⅰ）的合成
化合物（Ⅲ）与对苯二胺按照摩尔比2：1在水溶液中进行反应，滴加NaOH水溶液保持反应液pH=6.5，30～40℃搅拌反应6h，反应完后盐析，压滤，烘干，粉碎，到得到化合物（Ⅰ）。
实施例2：
本实施例提供了式（Ⅰ）化合物对棉织物的染色方法：
具体染色方法如下：
化合物（Ⅰ）用量2.0%(o.w.f，对织物重)，浴比1：50，室温入染，加元明粉5%(o.w.f，对织物重)，2℃/min升温到60℃，加纯碱10%(o.w.f，对织物重)，保温60min，染毕，水洗、皂洗、水洗。
Claims (2)
1.一种含氟活性荧光染料，其具有如式（Ⅰ）所示的结构：
（Ⅰ）。
2.一种如权利要求 1 所述的含氟活性荧光染料的应用，其特征在于作为活性染料对棉或黏胶纤维、纱线或织物进行染色。
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051134A (en) * | 1974-11-23 | 1977-09-27 | Bayer Aktiengesellschaft | Reactive dyestuffs |
| US4473693A (en) * | 1978-08-04 | 1984-09-25 | Stewart Walter W | Aminonaphthalimide dyes for intracellular labelling |
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2018
- 2018-03-31 CN CN201810287445.0A patent/CN108727864B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051134A (en) * | 1974-11-23 | 1977-09-27 | Bayer Aktiengesellschaft | Reactive dyestuffs |
| US4473693A (en) * | 1978-08-04 | 1984-09-25 | Stewart Walter W | Aminonaphthalimide dyes for intracellular labelling |
Non-Patent Citations (1)
| Title |
|---|
| X-型1,8萘酰亚胺类活性荧光染料的研究;赵同丰等;《染料工业》;19980615(第03期);第1-3页 * |
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Effective date of registration: 20201216 Address after: 224400 No. 5 Liuyang Road, Funing Economic Development Zone, Yancheng City, Jiangsu Province (A) Patentee after: Yancheng Leke Arts and Crafts Manufacturing Co.,Ltd. Address before: Room 1614, 16 / F, North building, innovation building, big data Industrial Park, Yannan high tech Zone, Yancheng City, Jiangsu Province 224000 (CNK) Patentee before: Yancheng Guanjia Technology Consulting Service Co.,Ltd. |
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20191105 |