CN116427189A - Fiber dyeing method and photochromic intelligent fabric based on DAAs - Google Patents
Fiber dyeing method and photochromic intelligent fabric based on DAAs Download PDFInfo
- Publication number
- CN116427189A CN116427189A CN202310454501.6A CN202310454501A CN116427189A CN 116427189 A CN116427189 A CN 116427189A CN 202310454501 A CN202310454501 A CN 202310454501A CN 116427189 A CN116427189 A CN 116427189A
- Authority
- CN
- China
- Prior art keywords
- fiber
- daas
- drying
- dyeing method
- dyeing
- 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
- 239000000835 fiber Substances 0.000 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims abstract description 64
- 238000004043 dyeing Methods 0.000 title claims abstract description 63
- 239000004744 fabric Substances 0.000 title claims abstract description 35
- 239000000543 intermediate Substances 0.000 claims abstract description 64
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 51
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002243 precursor Substances 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- 238000001035 drying Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 30
- 238000005406 washing Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 17
- 238000001291 vacuum drying Methods 0.000 claims description 16
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000000967 suction filtration Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- 239000013067 intermediate product Substances 0.000 claims description 9
- 238000002791 soaking Methods 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 6
- 238000005516 engineering process Methods 0.000 claims description 6
- 238000011049 filling Methods 0.000 claims description 6
- 238000005303 weighing Methods 0.000 claims description 6
- QEDCHCLHHGGYBT-UHFFFAOYSA-N 5-bromo-2,3-dihydro-1h-indole Chemical compound BrC1=CC=C2NCCC2=C1 QEDCHCLHHGGYBT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- 229940101545 mi-acid Drugs 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 32
- 229920000728 polyester Polymers 0.000 abstract description 12
- 239000000986 disperse dye Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 238000006317 isomerization reaction Methods 0.000 description 11
- 230000008859 change Effects 0.000 description 10
- 238000000985 reflectance spectrum Methods 0.000 description 9
- 230000006870 function Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004378 air conditioning Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 229910000906 Bronze Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 208000012886 Vertigo Diseases 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000010974 bronze Substances 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012621 metal-organic framework Substances 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 206010063385 Intellectualisation Diseases 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001988 diarylethenes Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- -1 polyoxometallates Chemical class 0.000 description 1
- 235000020004 porter Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005316 response function Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
Images
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
- D06P1/004—Dyeing with phototropic dyes; Obtaining camouflage effects
-
- 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
- D06P1/008—Preparing dyes in situ
-
- 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
-
- 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
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
- Y02P70/62—Manufacturing or production processes characterised by the final manufactured product related technologies for production or treatment of textile or flexible materials or products thereof, including footwear
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention provides a fiber dyeing method and a photochromic intelligent fabric based on DAAs, which comprises the following steps: reacting furfural with DAAs molecular precursors to obtain DAAs intermediates; dissolving the intermediate of DAAs in DMSO to prepare an intermediate dye solution; dyeing the fiber by using an intermediate dye liquor; the fiber was impregnated with intermediate B containing an aromatic ring as a donor for DASAs to complete fiber dyeing. Based on the technical scheme of the invention, the problem that the existing polyester fiber can only be dyed by using disperse dye with small molecular weight can be effectively solved, and the application range of DAAs as the photochromic intelligent fabric dye can be effectively enriched.
Description
Technical Field
The invention relates to the fields of photosensitive materials, clothing textile and printing and dyeing, in particular to a fiber dyeing method and a photochromic intelligent fabric based on DAAs.
Background
The intellectualization of clothing accessories, which is one of the most closely related aspects to human beings, is of great interest. The color of the clothing is of self-evident importance, the clothing with different colors has rich and beautiful wearing meanings, but people gradually find that the traditional dyeing and finishing technology is mainly characterized in that the color of the existing clothing is prepared by various dyes, the color cannot be intelligently changed once being molded, the application of the color clothing in more fields is greatly limited by the color with single functions, and therefore, the research of the color-changing fibers is very important for realizing practical application such as intelligent color-changing clothing. Compared with the traditional fabric, the intelligent fabric integrates various functions, such as an environmental stimulus response function, a physical sign monitoring function, a temperature self-adaptive adjusting function and the like. Intelligent fabrics with different functions have been widely studied and applied at present, and are an important development direction of textile science and materials science. Among the intelligent fabrics, the fabric with the photochromic property can correspondingly change the color along with the change of the ambient light, and has the practical functions of decoration, temperature control, camouflage, stealth and the like.
The first thing was observed in the nineteenth century, and the photochromic phenomena of inorganic and organic compounds were also found in the 40 s. The invention of the time-resolved spectroscopy technology of Porter accelerates the progress of the research of the photochromic substance. Photochromic materials are mainly classified into organic photochromic materials and inorganic photochromic materials. The organic photochromic material mainly comprises spiropyrans, fulgides, azobenzene, diarylethenes, spirooxazines and the like, and the inorganic photochromic material mainly comprises transition metal oxides, metal halides, polyoxometallates, rare earth complexes and the like. However, the inorganic photochromic materials have the defects of low photosensitive rate, poor color-changing reversibility and the like, so that the wide application and development of the inorganic photochromic materials are also limited to a great extent, for example, WO 3 The occurrence of photochromism whisker forms tungsten bronze material, and the tungsten bronze whisker is formed outside to WO 3 Providing protons or hydrogen atoms, so a simple WO 3 Poor photochromic sensitivity and even no discoloration. In textile applications, only reversible organic photochromic materials are of practical importance. At present, the photochromic intelligent fabric is characterized in that an organic photochromic compound is attached to the surface of the fabric or the inside of the fiber by a physical method or a chemical method, so that the fabric has a photochromic function, and the mechanism of the photochromic is thatThe organic photochromic compound can generate cis-trans isomerism or ring-opening-closing isomerism and other reactions under the light stimulus of specific wavelength, and the two states have different selective absorption of the light wavelength, so that different colors are displayed.
The physical method is to mix photochromic dye powder with a binder such as resin and then print the fabric, or uniformly disperse the photochromic compound in the spinning solution during the fiber spinning stage, or fix the photochromic microcapsules on the surface of the fabric by means of ink printing. Among them, the melt blending requires that the photochromic dye should withstand high temperatures.
Chemical processes, that is to say the bonding of the dye to the fibre, are carried out, for example, by impregnating the fibre or fabric with a spiropyran derivative-containing monomer, typically vinyl acetate or styrene, by graft polymerization techniques, the monomer being grafted into the fibre. Graft polymerization is more complex than conventional dye dyeing processes, and polymerization generally requires vacuum conditions. At present, the conventional dyeing and printing technology is seldom adopted for processing.
Polyester fibers are hydrophobic fibers, and the fibers lack groups capable of combining with dyes, cannot be dyed by water-soluble dyes, and can be dyed by nonionic disperse dyes which have small molecular weight, do not contain strong ionic water-soluble groups and have low solubility. The dyeing method of polyester fiber mainly comprises a high-temperature high-pressure dyeing method, a carrier dyeing method and a hot melt dyeing method at present. Among them, the high-temperature and high-pressure dyeing method is the most mainstream and common dyeing method because of the advantages of simple operation and environmental friendliness. The polyester structure is compact, the polyester is boiled and dyed at normal pressure, and dye is difficult to diffuse into the fiber to dye the fiber thoroughly. Thus, the glass transition temperature T is achieved by a high temperature and high pressure method (generally 120-150deg.C, pressurized by 2 atm) g In the above process, the fiber macromolecular chain segment moves vigorously, the intermolecular gaps of the polymer are increased, the free volume is increased, and the dyeing rate is improved. The carrier dyeing method has relatively less strict requirements on temperature, uses o-methyl phenol or methyl salicylate and the like as carriers, has small molecular weight, and can play a plasticizing role on the fiber before dyeing the fiber, thereby reducing the acting force among fiber moleculesThe chain segment movement of the amorphous area of the fiber is promoted, the dye is beneficial to dyeing, but the carrier is mostly toxic and harmful to human bodies, and the dyeing process causes great pollution to the environment. The hot melt dyeing method is to fully mix the dye and the polyester fiber melt and spin the mixture, and has strict requirements on the high temperature resistance of the dye and needs to resist the high temperature of more than 250 ℃.
Most of photochromic fabrics in the current stage have complex manufacturing process and low manufacturing cost, and most of photochromic fabrics are activated by ultraviolet light to realize photochromic in the visible light band. In the mainstream dyeing technology of polyester fiber at present, only small molecular disperse dye can be used for dyeing the color into the fiber, and other dyeing methods only fix the color on the surface of the fiber. The invention provides a preparation method of a photochromic intelligent fabric based on a donor acceptor Stenhaus adduct, which can effectively solve the problems that most of the existing photochromic intelligent fabrics are complex in preparation process, high in cost and incapable of changing color under visible light/white light, can effectively solve the problem that the existing polyester fiber can only be dyed by using a disperse dye with small molecular weight, and can effectively enrich the application range of DAAs as the photochromic intelligent fabric dye.
The donor-acceptor Stenhaus adducts (DAAs) are novel photochromic molecules with excellent performance, and have the advantages of easily available raw material sources, mild synthesis reaction conditions, easy modification, high yield and no pollution to the environment, and are structurally and functionally significant. DASAs molecules are composed of three parts, an electron donor moiety, an electron acceptor moiety, and a trien pi bridge structure attached thereto (fig. 1). DASAs molecules can transition from a colored state to a colorless state upon irradiation with visible light, and can return from the colorless state to the colored state after heat treatment (fig. 1).
DASAs have been used as a class of excellent photochromic materials and in different scenes due to their freely switching nature between colored and colorless. However, DASAs, like other conventional photochromic molecules, are difficult to exhibit rapid and efficient photochromic properties under solid conditions due to intermolecular packing. This further limits the application of DASAs in photochromic materials. In previous work, many groups of subjects focused on the application potential of DASAs as solid photochromic materials and produced different solid photochromic materials by using metal-organic framework materials, polymer materials, etc. as substrates, respectively. We have found that the isomerisation properties of DAAs in the solid state are closely related to their physicochemical environment. By controlling the surrounding physical and chemical environment, the isomerization property of DAAs in a solid state can be effectively improved, and the application of the solid photochromic material is further realized.
Disclosure of Invention
In view of the above problems in the prior art, the present application proposes a fiber dyeing method comprising the steps of:
s1, reacting furfural with DAAs molecular precursors to obtain DAAs intermediates;
s2, dissolving the intermediate of DAAs in DMSO to prepare an intermediate dye solution; dyeing the fiber by using an intermediate dye liquor;
s3, using the intermediate B containing the aromatic ring as a donor of DAAs to infiltrate the fiber, and finishing fiber dyeing.
Preferably, the DASAs molecular precursors include at least one of milbezier acid, 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one.
Preferably, the specific process of step S1 is: reacting Mi's acid with furfural to obtain a yellow crude product of the intermediate A of DAAs; washing the obtained yellow crude product with water, and filtering to remove water; removing impurities in the intermediate product in an extraction mode by sequentially using saturated sodium bisulphite and saturated sodium chloride aqueous solution, and further removing water in the intermediate product by using anhydrous magnesium sulfate or anhydrous sodium sulfate as a water removing agent in a suction filtration mode; finally purifying the obtained intermediate product by adopting a column chromatography technology, and adopting dichloromethane as an eluent; finally, the purified intermediate is obtained, and then the solvent is removed by rotary evaporation to obtain yellow solid.
Preferably, the specific process of step S2 is: and (2) weighing 0.22g of DAAs intermediate A obtained in the step (S1), taking 10mL of DMSO by using a syringe, dissolving the intermediate in the DMSO to prepare a dye solution with the mass fraction of the intermediate 1 of 2%, filling the dye solution into an eggplant-shaped bottle, adding 0.1g of PET fiber, heating the obtained product from normal temperature to 130 ℃ in an oil bath pot, and then preserving the heat for about 30min. Taking out the fiber with tweezers, washing the fiber with water, and then placing the fiber into a vacuum drying oven for drying;
preferably, the specific process of step S3 is: and (2) drying the fiber dyed by the DAAs intermediate obtained in the step (S2), taking out, sucking excessive N-methylaniline serving as a donor of the DAAs by using a rubber head dropper, fully soaking the fiber, reacting for 30min, washing the unreacted N-methylaniline on the surface of the fiber by using dichloromethane, drying in a vacuum drying oven, and setting the drying temperature to 40 ℃ for 4-5h.
Preferably, the specific process of step S1 is: heating and stirring 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one and furfural at 50 ℃ for reaction for 4-5 hours, and then sequentially carrying out washing, suction filtration, extraction, drying, secondary suction filtration, column chromatography purification and rotary evaporation to obtain an intermediate C of DAAs; the molar ratio of 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one to furfural is 1:1.
preferably, the specific process of step S2 is: weighing 0.11g of DAAs intermediate C obtained in the step S1, taking 10mL of DMSO by using a syringe, dissolving the intermediate C in the DMSO to prepare a dye liquor with the mass fraction of the intermediate C of 1%, filling the dye liquor into an eggplant-shaped bottle, adding 0.1g of PET fiber, heating to 130 ℃ from normal temperature in an oil bath pot, and preserving heat for about 30min; and then taking out the fiber, washing the fiber with water, and putting the fiber into a vacuum drying oven for drying.
Preferably, the specific process of step S3 is: and (3) taking out the dyed fiber of the dried DAAs intermediate C obtained in the step (S2), taking excessive indoline as a donor of DAAs by using a rubber head dropper, fully soaking the fiber, reacting for 30min, washing off unreacted indoline on the surface of the fiber by using dichloromethane, drying in a vacuum drying oven, and setting the drying temperature to 40 ℃ and drying for 4-5h.
Preferably, the specific process of step S3 is: taking out the dyed fiber of the dried DAAs intermediate C obtained in the step S2, sucking excessive 5-bromoindoline by using a rubber head dropper, fully soaking the fiber, and reacting for 30min to fully react the 5-bromoindoline with the DAAs intermediate C successfully dyed into the PET fiber in the step S2; and washing off unreacted indoline on the surface of the fiber by using dichloromethane, putting the fiber into a vacuum drying oven for drying, setting the drying temperature to 40 ℃, and drying for 4-5 hours.
The application relates to a DAAs-based photochromic intelligent fabric, which uses the fiber dyeing method.
The above-described features may be combined in various suitable ways or replaced by equivalent features as long as the object of the present invention can be achieved.
DASAs have been used as a class of excellent photochromic materials and in different scenes due to their freely switching nature between colored and colorless. However, DASAs, like other conventional photochromic molecules, are difficult to exhibit rapid and efficient photochromic properties under solid conditions due to intermolecular packing. This further limits the application of DASAs in photochromic materials. In previous work, many groups of subjects focused on the application potential of DASAs as solid photochromic materials and produced different solid photochromic materials by using metal-organic framework materials, polymer materials, etc. as substrates, respectively. We have found that the isomerisation properties of DAAs in the solid state are closely related to their physicochemical environment. By controlling the surrounding physical and chemical environment, the isomerization property of DAAs in a solid state can be effectively improved, and the application of the solid photochromic material is further realized.
The application prepares the photochromic fiber based on DAAs, and prepares the fabric with photochromic property through a textile process, so as to realize the controllable and reciprocating color change function of the clothes under the external light stimulation. In previous studies, we noted that the photochromic properties of DASAs in the solid state are closely related to the physicochemical environment in which they are subjected:
(1) From the perspective of physical environment, the phase with softer mechanical property in the material can promote the molecular motion property of DAAs, and further promote the isomerization property of DAAs in a solid state;
(2) From the chemical environment, the special functional group (ester group) in the material can promote the intramolecular proton transfer process in the DAAs isomerization process and further promote the isomerization process of the color change of the DAAs.
Based on the above principle, we use polyester fiber (PET) as the fiber matrix, and DAAs is not suitable for the high-pressure boiling dyeing method of the traditional PET because DAAs is not resistant to high temperature. The method comprises the steps of firstly boiling and dyeing DAAs intermediate into PET fiber under normal pressure, then dyeing the DAAs donor part and the treated fiber, and finally preparing the photochromic fabric from PET with photochromic property through a spinning process.
Based on the system, DAAs is used as dye to dye polyester fiber (PET) to prepare a fabric which can be directly worn on a human body, and the fabric can realize color change under sunlight, and has the following advantages:
1. the air conditioning clothing can be used for adjusting the surface temperature, reflecting light in the daytime and absorbing light at night, and reducing the temperature difference between two states.
2. For interesting color changes, it is expected to make garments with different properties based on DASAs with different colors and different properties. DASAs can also be a great advantage for white light development, and negative-color is a property unique to DASAs relative to other light-sensitive molecules.
3. Has the advantages of polyester fiber (PET) fabric and DAAs molecules. The prepared fabric is soft, strong in elasticity and not easy to deform, can realize reciprocating color change under visible light, has certain fatigue resistance, is low in cost and easy to obtain raw materials, and has environmental friendliness in the manufacturing process
The beneficial effects of the invention are as follows:
(1) According to the invention, DAAs is used for dyeing polyester fiber yarns, and various daily wearable photochromic fabrics can be manufactured through a conventional textile process, so that interesting color change is realized. The fabric can be changed by visible light triggering, and has the advantages of short photoinduction stimulation time, high response speed, repeatable color change and the like. The application of DAAs not only avoids the damage of ultraviolet light to molecular structures, but also widens the selection range of PET fibers to dyes, and shows great potential of DAAs in the field of intelligent fabrics.
(2) According to the invention, DAAs molecules are successfully dyed into PET fibers by a two-step dyeing method, so that the defect that DAAs cannot resist dyeing high temperature at the current stage is avoided, and the deterioration of DAAs at high temperature in the dyeing process is avoided, and the molecular reaction rate is high. And the absorption/release characteristics of DAAs in the color developing/fading process can be used as 'air conditioning clothing' to regulate the surface temperature of the human body.
(3) The materials adopted in the preparation process are cheap and easy to obtain, the preparation and synthesis method is simple and easy to operate, and the preparation method has great potential of low-cost industrialization.
Drawings
The invention will be described in more detail hereinafter on the basis of embodiments and with reference to the accompanying drawings. Wherein:
FIG. 1 shows a general molecular structure schematic and a photoisomerization schematic of DAAs of the present invention;
FIG. 2 shows a schematic representation of the preparation of DAAs molecular intermediate A of the present invention;
FIG. 3 shows a schematic representation of the preparation of DAAs-I molecules of the present invention;
FIG. 4 shows a schematic representation of the preparation of DAAs molecular intermediate C of the present invention;
FIG. 5 shows a schematic representation of the preparation of DAAs-II molecules of the present invention;
FIG. 6 shows a schematic representation of the preparation of DAAs-III molecules of the present invention;
FIG. 7 shows experimental pictures of DAAs-I@PET of the invention;
FIG. 8 shows the illumination (520 nm) UV-visible reflectance spectrum of DASA-I@PET of the invention;
FIG. 9 shows the ultraviolet visible reflectance spectrum of DASA-I@PET of the present invention (60 ℃,10 RH);
FIG. 10 shows experimental pictures of DAAs-II@PET of the present invention;
FIG. 11 shows the illumination (660 nm) UV-visible reflectance spectrum of DASA-II@PET of the invention;
FIG. 12 shows the ultraviolet visible reflectance spectrum of DASA-II@PET of the present invention (55deg.C, 10 RH);
FIG. 13 shows experimental pictures of DAAs-II@PET of the present invention;
FIG. 14 shows the illumination (660 nm) UV-visible reflectance spectrum of DASA-III@PET of the invention;
FIG. 15 shows the ultraviolet visible reflectance spectrum of DASA-III@PET of the invention at room temperature dark recovery (17 ℃, dark conditions).
Detailed Description
The invention will be further described with reference to the accompanying drawings.
The invention provides a fiber dyeing method, which comprises the following steps:
s1, reacting furfural with DAAs molecular precursors to obtain DAAs intermediates;
s2, dissolving the intermediate of DAAs in DMSO to prepare an intermediate dye solution; dyeing the fiber by using an intermediate dye liquor;
s3, using the intermediate B containing the aromatic ring as a donor of DAAs to infiltrate the fiber, and finishing fiber dyeing.
In one embodiment, as shown in fig. 2, in step S1, the milbezier acid and the furfural are heated and stirred at the temperature of 30-40 ℃ for 4-5 hours, and then water is removed by washing and suction filtration in sequence. And then sequentially using saturated sodium bisulphite and saturated sodium chloride aqueous solution to remove impurities in the intermediate product in an extraction mode, and then using anhydrous magnesium sulfate or anhydrous sodium sulfate as a water scavenger to further remove water in the intermediate product in a suction filtration mode. The intermediate product obtained is then finally purified by column chromatography using Dichloromethane (DCM) as eluent. Finally, removing the solvent by rotary evaporation after obtaining the purified intermediate to obtain yellow solid, namely DAAs intermediate A; the molar ratio of the Mi's acid to the furfural is 1:1. and S2, weighing 0.22g of the DAAs intermediate A obtained in the step S1, taking 10mL of DMSO by using a syringe, dissolving the intermediate in the DMSO to prepare a dye solution with the mass fraction of the intermediate A of 2%, filling the dye solution into an eggplant-shaped bottle, adding 0.1g of PET fiber, heating the obtained product from normal temperature to 130 ℃ in an oil bath pot, and then preserving the heat for about 30min. Taking out the fiber with tweezers, washing the fiber with water, and then placing the fiber into a vacuum drying oven for drying; and S3, as shown in FIG. 3, taking out the dyed fiber of the dried DAAs intermediate obtained in the step S2, fully soaking the fiber with excessive N-methylaniline, reacting for 30min, washing the unreacted N-methylaniline on the surface of the fiber with ethanol, putting the fiber into a vacuum drying oven for drying (for example, if the fiber is washed with ethanol or dichloromethane, the drying temperature can be set to be 40 ℃), and drying for 4-5h.
In one embodiment, as shown in fig. 4, step S1, heating and stirring 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one and furfural at 50 ℃ for 4-5 hours, and then sequentially performing water washing, suction filtration, extraction, drying, secondary suction filtration, column chromatography purification and rotary evaporation to obtain DASAs intermediate C; the molar ratio of 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one to furfural is 1:1. and S2, weighing 0.11g of the DAAs intermediate obtained in the step S1, taking 10mL of DMSO by using a syringe, dissolving the intermediate in the DMSO to prepare a dye liquor with the mass fraction of 1% of the intermediate C, filling the dye liquor into an eggplant-shaped bottle, adding 0.1g of PET fiber, heating to 130 ℃ from normal temperature in an oil bath, and then preserving heat for about 30min. Taking out the fiber with tweezers, washing the fiber with water, and then placing the fiber into a vacuum drying oven for drying; and S3, as shown in FIG. 5, taking out the dyed fiber of the dried DAAs intermediate obtained in the step S2, fully soaking the fiber with excessive indoline, reacting for 30min, washing off unreacted indoline on the surface of the fiber by using an organic solvent, placing the fiber into a vacuum drying oven for drying (for example, if the fiber is washed by ethanol or dichloromethane, the drying temperature can be set to be 40 ℃), and drying for 4-5h.
In one embodiment, step S1, carrying out heating stirring reaction on 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one and furfural for 4-5 hours at 50 ℃, and then sequentially carrying out washing, suction filtration, extraction, drying, secondary suction filtration, column chromatography purification and rotary evaporation to obtain a DAAs intermediate C; the molar ratio of 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one to furfural is 1:1. and S2, dissolving the DAAs intermediate obtained in the step S1 in DMSO, adding a proper amount of PET fibers, heating to 130 ℃, and preserving heat for about 30min. Taking out the fiber, washing the fiber with water, and then putting the fiber into a vacuum drying oven for drying; step S3, as shown in FIG. 6, taking out the dyed fiber of the dried DAAs intermediate obtained in step S2, fully soaking the fiber with excessive 5-bromoindoline, reacting for 30min, washing off unreacted indoline on the surface of the fiber with organic solvent ethanol, and drying in a vacuum drying oven (for example, if the fiber is washed with ethanol or dichloromethane, the drying temperature can be set to 40 ℃).
In one embodiment, after the fiber is dyed with the intermediate, it may be washed with solvents such as ethanol, methylene chloride, methanol, EA, and the like, in addition to water.
In one embodiment, after the fibers are dyed with DASAs molecules, the surface of the fibers may be washed with solvents such as ethanol, methanol, EA, and the like in addition to methylene chloride to wash away unreacted receptors.
Experimental pictures of fibers prepared by DAAs-I molecular dyeing (DAAs-I@PET). As shown in FIG. 7, DASA-I molecules were successfully dyed into the interior of PET fibers, which exhibited a purple color, and the color was not easily washed off with an organic solvent without an additional protective layer.
Reflectance spectra of light and heat recovery experiments of fibers prepared by DAAs-I molecular dyeing. Spectral diagrams of the DAAs-I@PET isomerization process from colored to colorless (FIG. 8) and the isomerization process from colorless to colored (FIG. 9). That is, under 520nm light, the purple color of the PET fibers gradually faded over time, and the purple color of the PET fibers reappears in a dry environment at 55 ℃ and 10 RH.
Experimental pictures of fibers prepared by DAAs-II molecular dyeing (DAAs-II@PET). As shown in fig. 10, DASA-ii molecules were successfully dyed into the inside of PET fiber, which exhibited green color, and the color was not easily washed off with an organic solvent, without an additional protective layer.
Reflectance spectra of light and heat recovery experiments of fibers prepared by DAAs-II molecular dyeing. Spectral changes of DASAs-ii @ PET from colored to colorless isomerization process (fig. 11) and colorless to colored isomerization process (fig. 12). I.e. the green colour of the PET fibres fades over time under 660nm light, whereas the green colour of the PET fibres reappears in a dry environment at 55 ℃ and 10 RH.
Experimental pictures of fibers prepared by DAAs-III molecular dyeing. As shown in fig. 13, DASA-iii molecules were dyed inside PET fibers, which exhibited purple color, and the color was not easily washed out with an organic solvent, without an additional protective layer. FIGS. 14-15 are reflectance spectra of light and heat recovery experiments for fibers prepared by DAAs-III molecular dyeing.
The DAAS-based photochromic intelligent fabric provided by the invention can realize repeated color change under the stimulation of visible light, can realize rich and interesting color change, is different from the traditional fabric and other photochromic fabrics, and has great application prospects in various fields such as daily life, sports, military national defense and the like.
The PET fiber dyeing method provided by the invention is different from the traditional dyeing with small molecule disperse dye, and is different from the melt dyeing method and printing dyeing of other photochromic dyes. The DAAs molecules are successfully dyed into the PET fibers, the defect that DAAs cannot resist the high temperature of dyeing at the current stage is avoided, the deterioration of DAAs at the high temperature in the dyeing process is avoided, and the reaction yield is high. And the absorption/release characteristics of DAAs in the color developing/fading process can be used as 'air conditioning clothing' to regulate the surface temperature of the human body.
The materials adopted in the preparation process are cheap and easy to obtain, the preparation and synthesis method is simple and easy to operate, and the preparation method has great potential of low-cost industrialization.
Although the invention herein has been described with reference to particular embodiments, it is to be understood that these embodiments are merely illustrative of the principles and applications of the present invention. It is therefore to be understood that numerous modifications may be made to the illustrative embodiments and that other arrangements may be devised without departing from the spirit and scope of the present invention as defined by the appended claims. It should be understood that the different dependent claims and the features described herein may be combined in ways other than as described in the original claims. It is also to be understood that features described in connection with separate embodiments may be used in other described embodiments.
Claims (10)
1. A method of dyeing fibers, comprising the steps of:
s1, reacting furfural with DAAs molecular precursors to obtain DAAs intermediates;
s2, dissolving the intermediate of DAAs in DMSO to prepare an intermediate dye solution; dyeing the fiber by using an intermediate dye liquor;
s3, using the intermediate B containing the aromatic ring as a donor of DAAs to infiltrate the fiber, and finishing fiber dyeing.
2. The fiber dyeing method of claim 1, wherein the DASAs molecular precursor comprises at least one of milbezier acid, 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one.
3. The fiber dyeing method according to claim 1, wherein the specific process of step S1 is: reacting Mi's acid with furfural to obtain a yellow crude product of the intermediate A of DAAs; washing the obtained yellow crude product with water, and filtering to remove water; removing impurities in the intermediate product in an extraction mode by sequentially using saturated sodium bisulphite and saturated sodium chloride aqueous solution, and further removing water in the intermediate product by using anhydrous magnesium sulfate or anhydrous sodium sulfate as a water removing agent in a suction filtration mode; finally purifying the obtained intermediate product by adopting a column chromatography technology; finally, the purified intermediate is obtained, and then the solvent is removed by rotary evaporation to obtain yellow solid.
4. The fiber dyeing method according to claim 1, wherein the specific process of step S2 is: and (2) weighing 0.22g of DAAs intermediate A obtained in the step (S1), taking 10mL of DMSO by using a syringe, dissolving the intermediate in the DMSO to prepare a dye solution with the mass fraction of the intermediate 1 of 2%, filling the dye solution into an eggplant-shaped bottle, adding 0.1g of PET fiber, heating the obtained product from normal temperature to 130 ℃ in an oil bath pot, and then preserving the heat for about 30min. And taking out the fiber by using tweezers, washing the fiber by using water, and putting the fiber into a vacuum drying oven for drying.
5. The fiber dyeing method according to claim 1, wherein the specific process of step S3 is: and (2) drying the fiber dyed by the DAAs intermediate obtained in the step (S2), taking out, sucking excessive N-methylaniline serving as a donor of the DAAs by using a rubber head dropper, fully soaking the fiber, reacting for 30min, washing the unreacted N-methylaniline on the surface of the fiber by using dichloromethane, drying in a vacuum drying oven, and setting the drying temperature to 40 ℃ for 4-5h.
6. The fiber dyeing method according to claim 1, wherein the specific process of step S1 is: heating and stirring 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one and furfural at 50 ℃ for reaction for 4-5 hours, and then sequentially carrying out washing, suction filtration, extraction, drying, secondary suction filtration, column chromatography purification and rotary evaporation to obtain an intermediate C of DAAs; the molar ratio of 1-phenyl-3-trifluoromethyl-1 (H) -pyrazol-5-one to furfural is 1:1.
7. the fiber dyeing method according to claim 6, wherein the specific process of step S2 is as follows: weighing 0.11g of DAAs intermediate C obtained in the step S1, taking 10mL of DMSO by using a syringe, dissolving the intermediate C in the DMSO to prepare a dye liquor with the mass fraction of the intermediate C of 1%, filling the dye liquor into an eggplant-shaped bottle, adding 0.1g of PET fiber, heating to 130 ℃ from normal temperature in an oil bath pot, and preserving heat for about 30min; and then taking out the fiber, washing the fiber with water, and putting the fiber into a vacuum drying oven for drying.
8. The fiber dyeing method according to claim 7, wherein the specific process of step S3 is: and (3) taking out the dyed fiber of the dried DAAs intermediate C obtained in the step (S2), taking excessive indoline as a donor of DAAs by using a rubber head dropper, fully soaking the fiber, reacting for 30min, washing off unreacted indoline on the surface of the fiber by using dichloromethane, drying in a vacuum drying oven, and setting the drying temperature to 40 ℃ and drying for 4-5h.
9. The fiber dyeing method according to claim 7, wherein the specific process of step S3 is: taking out the dyed fiber of the dried DAAs intermediate C obtained in the step S2, sucking excessive 5-bromoindoline by using a rubber head dropper, fully soaking the fiber, and reacting for 30min to fully react the 5-bromoindoline with the DAAs intermediate C successfully dyed into the PET fiber in the step S2; and washing off unreacted indoline on the surface of the fiber by using dichloromethane, putting the fiber into a vacuum drying oven for drying, setting the drying temperature to 40 ℃, and drying for 4-5 hours.
10. A photochromic intelligent fabric based on DASAs, characterized in that the fiber dyeing method of claim 1 is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310454501.6A CN116427189A (en) | 2023-04-25 | 2023-04-25 | Fiber dyeing method and photochromic intelligent fabric based on DAAs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310454501.6A CN116427189A (en) | 2023-04-25 | 2023-04-25 | Fiber dyeing method and photochromic intelligent fabric based on DAAs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116427189A true CN116427189A (en) | 2023-07-14 |
Family
ID=87087172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310454501.6A Pending CN116427189A (en) | 2023-04-25 | 2023-04-25 | Fiber dyeing method and photochromic intelligent fabric based on DAAs |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116427189A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190127345A1 (en) * | 2016-04-26 | 2019-05-02 | The Regents Of The University Of California | Negative photochromic materials with tunable properties |
| CN109895520A (en) * | 2019-03-19 | 2019-06-18 | 电子科技大学 | Reusable thermosensitive color development material and preparation method thereof and thermosensitive color development paper |
| CN111849248A (en) * | 2020-07-13 | 2020-10-30 | 电子科技大学 | Photochromic anti-counterfeiting bar code and preparation method thereof |
| CN114573544A (en) * | 2022-03-04 | 2022-06-03 | 南京理工大学 | Molecular switch with multiple stimulus responses and synthesis method thereof |
| CN115304552A (en) * | 2022-08-03 | 2022-11-08 | 中山大学 | Reversible photochromic dihydroxy functional monomer and preparation method and application thereof |
-
2023
- 2023-04-25 CN CN202310454501.6A patent/CN116427189A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190127345A1 (en) * | 2016-04-26 | 2019-05-02 | The Regents Of The University Of California | Negative photochromic materials with tunable properties |
| CN109895520A (en) * | 2019-03-19 | 2019-06-18 | 电子科技大学 | Reusable thermosensitive color development material and preparation method thereof and thermosensitive color development paper |
| CN111849248A (en) * | 2020-07-13 | 2020-10-30 | 电子科技大学 | Photochromic anti-counterfeiting bar code and preparation method thereof |
| CN114573544A (en) * | 2022-03-04 | 2022-06-03 | 南京理工大学 | Molecular switch with multiple stimulus responses and synthesis method thereof |
| CN115304552A (en) * | 2022-08-03 | 2022-11-08 | 中山大学 | Reversible photochromic dihydroxy functional monomer and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| SEBASTIAN ULRICH等: "Electrospun colourimetric sensors for detecting volatile amines", SENSORS AND ACTUATORS B: CHEMICAL, vol. 322, 9 July 2020 (2020-07-09), pages 128570 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102071012B (en) | Photosensitive material with Anderson type polyacid and preparation method thereof | |
| CN102071490A (en) | Method for preparing organic photochromic nanofibers | |
| Fan et al. | Preparation of photochromic wool fabrics based on thiol-halogen click chemistry | |
| CN112321485B (en) | PH-sensitive dye for textile material, preparation method and application thereof | |
| Utsumi et al. | Synthesis of a novel family of photochromic amorphous molecular materials based on dithienylethene, their photochromic properties and application for dual image formation | |
| CN107446379B (en) | A kind of synthesis of loop coil class nagative photochromism reactive dye | |
| CN111440193B (en) | Indene-thick naphtho-spirooxazine photochromic compound and preparation method thereof | |
| Hassabo et al. | Chromic dyes for smart textile: A review | |
| CN116427189A (en) | Fiber dyeing method and photochromic intelligent fabric based on DAAs | |
| CN108083969B (en) | Spiroindene compounds, their preparation and use | |
| Gao et al. | Construction of durable and original color constancy photochromic cotton fabrics by a facile esterification strategy | |
| CN113832717B (en) | Spiropyran photochromic cotton fabric and preparation method thereof | |
| CN112662394A (en) | Thermal stimulation fluorescence/visible light color dual-response capsule and synthesis method thereof | |
| Nakao et al. | Synthesis and photochromic properties of spironaphth [1, 2-b] oxazine containing a reactive substituent | |
| EP3257900B1 (en) | Use of indigo-derivatives as irreversible color changeable dyes for textile materials, novel compounds and a process for dyeing textile materials | |
| JP2018028168A5 (en) | ||
| JP4706025B2 (en) | Photochromic compound | |
| CN107337662B (en) | Water-soluble bi-fluorenyl quinoid thiophene derivative, preparation method and dyeing application thereof | |
| CN109898367B (en) | Preparation method of inkless repeatedly erasable nanofiber paper and product thereof | |
| Croitoru et al. | Smart dyes for medical textiles and related therapy | |
| CN117024401B (en) | Triphenylvinyl thiophene compound and preparation method and application thereof | |
| CN104711698A (en) | Photochromic water-repellent non-woven fabric and preparation method thereof | |
| CN111518120A (en) | Synthetic method for improving photochromic property of spiropyran by introducing multi-aromatic ring | |
| Liu | A simple fluorescent switch with four states based on benzothiazole-spiropyran for reversible multicolor displays and anti-counterfeiting | |
| CN114685381B (en) | Donor-acceptor Stenhaus adduct of non-conjugated aniline bridged tetraphenyl ethylene 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 |