CN113308894A - Acid-induced color-changing intelligent textile and preparation method thereof - Google Patents
Acid-induced color-changing intelligent textile and preparation method thereof Download PDFInfo
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/418—Cyclic amides, e.g. lactams; Amides of oxalic acid
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
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Abstract
The invention provides an acid-induced color-changing intelligent textile and a preparation method thereof. The preparation method comprises the steps of taking a textile containing hydroxyl as a grafting main body, taking a rhodamine-naphthalimide fluorescent material as an acid-induced discoloration matrix, and carrying out covalent fixation on the surface of the textile grafting main body treated by a silane coupling agent through a two-step method to prepare the acid-induced discoloration intelligent textile. The acid-induced color-changing intelligent textile has the advantages of high response speed, excellent fastness and small detection interval, and can adapt to strong acid conditions; the technical defect that dye molecules are combined with a matrix through physical adsorption and electrostatic action by adopting a simple dipping or coating process in the prior art, so that the dye molecules are not combined firmly enough and easily fall off is effectively overcome; the technical defects of complex process or the need of harsh conditions such as strong acid, strong alkali, oxidation and the like in the prior art in a chemical bonding mode are overcome.
Description
Technical Field
The invention relates to the technical field of intelligent textile preparation, in particular to an acid-induced color-changing intelligent textile and a preparation method thereof.
Background
The acid-base response color-changing textile can be applied to various scenes, such as medical dressings, and the wound healing degree can be known by observing the color change of the dressings; the color-changing protective clothing can also be integrated into protective clothing, and the safety degree of the environment can be sensed according to the color change of the clothing when a wearer is in the environment with the danger of acid exposure; meanwhile, the preservative color developing card can be made into a food preservative color developing card, and the putrefaction degree of the food can be judged according to the change of the pH value of the food; in addition, the pH value is closely related to the metabolic process of the human body, and the intelligent wearable textile can monitor various body fluids in real time. Therefore, the development of a novel portable intelligent environment-friendly acid-base response chromogenic material has wide application prospect.
However, the preparation of acid-discoloration textiles is currently mostly based only on simple impregnation or coating treatments. For example, patent application No. cn201910112752.x discloses an intelligent sweat acid-base color-changing garment, which is made by soaking yarn or fabric in natural dye and can change color within 80 s. The patent with the application number of CN202010593515.2 discloses a fabric sensor with a pH response color change function, and a preparation method and application thereof. However, in these methods, the dye molecules and the textile only rely on physical adsorption and electrostatic interaction, and there is no strong chemical bond, which results in that the dye molecules are easy to fall off during the use process, and there is a risk of secondary pollution to human body or environment. Therefore, how to fix the dye molecules on the textile through stable chemical bond covalent interaction is very important.
In recent years, some scientists have tried to prepare intelligent sensing textiles by covalently grafting such molecules onto cotton fabrics, for example, Sensors & Actuators: b.chemical.2018,275, 439-445 have reported a synthetic method for grafting naphthalimide molecular probes onto cotton fabrics through covalent bonds, but the preparation process of the method is complicated, and reagents such as strong acid and strong base are required, which is not favorable for practical application.
In view of the above, there is a need to design an improved intelligent textile with dual sensing of acid-induced color change and fluorescence and a preparation method thereof, so as to solve the above problems.
Disclosure of Invention
The invention aims to provide an acid-induced color-changing intelligent textile and a preparation method thereof.
In order to realize the aim, the invention provides a preparation method of an acid-induced color-changing intelligent textile, which comprises the following steps:
s1, adding the hydroxyl-containing textile and an aminosilane coupling agent into ethanol according to a preset proportion, stirring for 16-40 h at room temperature, washing with ethanol, and drying for post-treatment to obtain an aminated coupled textile;
s2, adding organic base into an organic solvent according to a preset proportion, uniformly mixing, adding a rhodamine-naphthalimide material, and fully mixing to obtain a mixed solution;
s3, adding the coupled textile into the mixed solution, reacting for 18-32 hours at 70-90 ℃ in a nitrogen protective atmosphere, and cleaning and drying the reacted textile with ethanol to obtain the acid-induced color-changing intelligent textile.
As a further improvement of the invention, the textile surface contains hydroxyl groups, which includes but is not limited to one of cotton fabric, non-woven fabric and regenerated cellulose fabric.
As a further improvement of the invention, the structural formula of the rhodamine-naphthalimide material is as follows:
wherein, the R group is one of halogen substituent, nitro and sulfonic group.
As a further improvement of the present invention, in step S1, the mass ratio of the textile to the aminosilane coupling agent is 1: (0.8-1.6), and the concentration of the aminosilane coupling agent is 8-12%.
As a further improvement of the invention, the aminosilane coupling agent is one of aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane and N- [3- (trimethoxysilyl) propyl ] ethylenediamine.
In a further improvement of the present invention, in step S2, the organic base is one of triethylamine, N-diisopropylethylamine, triethylenediamine, and pyridine.
As a further improvement of the invention, in step S2, the molar ratio of the organic base to the rhodamine-naphthalimide material is (5-6): 1.
As a further improvement of the invention, the organic solvent is one of ethylene glycol methyl ether, ethylene glycol, tetrahydrofuran, dimethyl sulfoxide, nitrogen-dimethyl formamide and nitrogen, nitrogen-dimethyl acetamide.
In order to realize the purpose, the invention also provides the acid-induced color-changing intelligent textile prepared by the preparation method, and the structural formula of the acid-induced color-changing intelligent textile is as follows:
as a further improvement of the invention, the performance parameters of acid-induced color change of the acid-induced color change intelligent textile are as follows: the color depth of the obtained textile shows a good linear and obvious gradient relation along with the change of acidity within the range of pH value of 3-6. In an acidic solution with pH 2, the intelligent fabric can change color obviously within 1s, and the color is well maintained within 24 h. Meanwhile, the obtained fabric has better binding fastness with dye, and is suitable for use in practical environment.
The invention has the beneficial effects that:
1. the invention provides an acid-induced color-changing intelligent textile, which takes a textile containing hydroxyl as a grafting main body and a rhodamine-naphthalimide material as an acid-induced color-changing matrix, wherein brominated naphthalimide provides a connection effect (a grafting reaction of a naphthalimide derivative, namely, a leaving group such as naphthalimide 4-site halogen or nitryl and the like on a cotton fabric containing hydroxyl or other textiles), and covalent fixation is carried out on the surface of the textile grafting main body treated by a silane coupling agent through a two-step method; the response speed is high, the fastness is excellent, the detection interval is small (0.5 pH value), and the method can adapt to strong acid conditions; the technical defects that a single rhodamine immobilization mode is complex and single naphthalimide cannot provide naked-eye color change are overcome, and the technical defect that in the prior art, a dye molecule and a matrix are combined through physical adsorption and electrostatic action by adopting a simple dipping or coating process, so that the dye molecule is not high in combining fastness and is easy to fall off is effectively overcome; the technical defects of complex process or the need of harsh conditions such as strong acid, strong alkali, oxidation and the like in the prior art in a chemical bonding mode are overcome.
2. The preparation method of the acid-induced color-changing intelligent textile provided by the invention has the advantages that the synthesis process is simple, the harsh conditions of strong acid, strong alkali, oxidation and the like are not needed, and the mass production can be realized; in addition, the preparation method has the advantages that the used medicines are simple and easy to obtain in the formula, and the reaction conditions are mild, so that the original properties of textiles such as cotton fabrics can not be damaged.
3. The acid-induced color-changing intelligent textile provided by the invention is wide in application range, not only can be applied to the field of clothes, but also can be applied to the fields of special factory warning agents, medical dressings, food safety detection and the like.
Drawings
FIG. 1 is a K/S change diagram of the acid-induced color-changing intelligent cotton fabric provided by the embodiment 1 of the invention in response to different pH values.
Fig. 2 is a graph showing the change of the acid-induced color-changing intelligent cotton fabric provided by the embodiment 1 of the invention in response to different pH values.
Fig. 3 is a time-dependent change-in-pH response diagram of the acid-induced color-changing intelligent cotton fabric provided in embodiment 1 of the present invention.
FIG. 4 is a graph showing the change of fluorescence gradient of the acid-induced color-changing intelligent cotton fabric provided in embodiment 1 in response to different pH values.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in detail with reference to the accompanying drawings and specific embodiments.
It should be noted that, in order to avoid obscuring the present invention with unnecessary details, only the structures and/or processing steps closely related to the aspects of the present invention are shown in the drawings, and other details not closely related to the present invention are omitted.
In addition, it is also to be noted that the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
The invention provides a preparation method of an acid-induced color-changing intelligent textile, which comprises the following steps:
s1, adding the hydroxyl-containing textile and the aminosilane coupling agent into ethanol according to a preset proportion, stirring for 16-40 h at room temperature, washing with ethanol, and drying for post-treatment to obtain a coupled textile;
s2, adding organic base into an organic solvent according to a preset proportion, uniformly mixing, adding a rhodamine-naphthalimide material, and fully mixing to obtain a mixed solution;
s3, adding the coupled textile into the mixed solution, reacting for 18-32 hours at 70-90 ℃ in a nitrogen protective atmosphere, and cleaning and drying the reacted textile with ethanol to obtain the acid-induced color-changing intelligent textile.
Preferably, the textile surface contains hydroxyl groups, which include but are not limited to one of cotton fabric, non-woven fabric, and regenerated cellulose fabric.
Preferably, the structural formula of the rhodamine-naphthalimide material is as follows:
wherein, the R group is one of halogen substituent, nitro and sulfonic group.
Preferably, in step S1, the mass ratio of the textile to the aminosilane coupling agent is 1: (0.8-1.6), and the concentration of the aminosilane coupling agent is 8-12%.
Preferably, the aminosilane coupling agent is one of aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane and N- [3- (trimethoxysilyl) propyl ] ethylenediamine.
Preferably, in step S2, the organic base is one of triethylamine, N-diisopropylethylamine, triethylenediamine, and pyridine.
Preferably, in step S2, the molar ratio of the organic base to the rhodamine-naphthalimide material is (5-6): 1.
Preferably, the organic solvent is one of ethylene glycol methyl ether, ethylene glycol, tetrahydrofuran, dimethyl sulfoxide, nitrogen-dimethylformamide and nitrogen, nitrogen-dimethylacetamide.
Example 1
s1, 21 g Aminopropyltriethoxysilane (ATPES) was added to the flask, 189 g ethanol was added to the flask, and finally 15 pieces of commercially available white cotton fabric (3cm x 3cm) were added to the flask, stirred at room temperature for 24 hours, and finally washed with ethanol and dried to obtain coupled cotton.
S2, adding 225mL of ethylene glycol monomethyl ether into a flask, adding 4.5 g of triethylamine, and finally adding 5 g of rhodamine-naphthalimide material, and fully mixing to obtain a mixed solution; the structural formula of the rhodamine-naphthalimide material is as follows:
S3, adding the coupling cotton cloth into the mixed solution, reacting for 24 hours at 80 ℃ in a nitrogen protection atmosphere, and washing and drying the obtained white probe cotton fabric with ethanol to obtain the acid-induced color-changing intelligent cotton fabric.
The preparation route of the intelligent acid-induced discoloration and fluorescence double-sensing cotton fabric prepared in the embodiment 1 is as follows:
the acid-induced color change intelligent cotton fabric has the following structural formula change:
and (3) performance testing:
respectively adding an acid-induced color change and fluorescence dual-sensing intelligent cotton fabric (3cm by 3cm) into 20ml of solutions with different pH values, and carrying out performance test.
Referring to FIG. 1, the color depth KS shows a good linear relationship with the pH within a range of pH 3 to 6.
Referring to fig. 2, in the range of pH 3-6, the obtained cotton fabric is obviously discolored and shows obvious gradient change with the increase of acidity.
Referring to fig. 3, in an acidic solution with pH 2, the intelligent cotton fabric discolored significantly within 1s, and the color was well maintained within 24 h. Meanwhile, the solution still keeps clear, and the color change phenomenon caused by the falling of the dye does not occur, so that the obtained cotton fabric and the dye have better binding fastness and are suitable for being used in the actual environment.
Referring to fig. 4, in the range of pH 1-6, the fluorescence gradient change of the obtained cotton fabric is not very obvious, which is mainly due to the fact that the cotton fabric has texture and unevenness on the surface, and the fluorescence gradient change of the intelligent fabric is influenced to a certain extent.
Example 2
s1, 21 g Aminopropyltriethoxysilane (ATPES) was added to the flask, 189 g ethanol was added to the flask, and finally the cellulose membrane (regenerated cellulose fabric) (3cm × 3cm) was added to the flask, stirred at room temperature for 24 hours, washed with ethanol, and dried to obtain a coupled cellulose membrane.
S2, adding 225mL of ethylene glycol monomethyl ether into a flask, adding 4.5 g of triethylamine, and finally adding 5 g of rhodamine-naphthalimide material, and fully mixing to obtain a mixed solution; the structural formula of the rhodamine-naphthalimide material is as follows:
S3, adding the coupled cellulose membrane into the mixed solution, reacting for 24 hours at 80 ℃ in a nitrogen protective atmosphere, and washing and drying the obtained cellulose membrane with ethanol to obtain the acid discoloration intelligent cellulose membrane.
And (3) performance testing:
to 20ml of each solution at different pH, an acid-discolored smart cellulose membrane (3 cm. times.3 cm) was added and tested for performance.
The performance of the acid-induced color-changing intelligent cellulose membrane prepared in the embodiment 2 is that the color depth shows good linear and gradient relation with the change of acidity in the range of pH value of 3-6 of the obtained textile. Within the pH value range of 3-6, the acid-induced discoloration intelligent cellulose membrane is obvious in discoloration and shows obvious gradient change along with the increase of acidity.
Meanwhile, in view of the smooth and flat surface condition of the cellulose membrane, compared with the cotton fabric in example 1, the acid-induced color-changing intelligent cellulose membrane in example 2 can show a certain fluorescence gradient change, and the effect of the acid-induced color-changing intelligent cellulose membrane is better than that of the fluorescence gradient change in example 1. In the embodiment 2 of the invention, two fluorescent groups, namely rhodamine and naphthalimide, are adopted, and under different acidic conditions, the interaction verification effect shown in the following structural formula can be achieved to a certain extent, so that the acid-induced discoloration intelligent cellulose membrane has the functions of acid-induced discoloration and fluorescence dual sensing. The structural formula change of the intelligent textile in the acid discoloration and fluorescence double sensing process is as follows:
example 3
s1, 21 g Aminopropyltriethoxysilane (ATPES) was added to the flask, 189 g ethanol was added to the flask, and finally the cellulose membrane (3cm × 3cm) was added to the flask, stirred at room temperature for 24 hours, washed with ethanol, and dried to obtain a coupled cellulose membrane.
S2, adding 225mL of ethylene glycol monomethyl ether into a flask, adding 4.5 g of triethylamine, and finally adding 5 g of rhodamine-naphthalimide material, and fully mixing to obtain a mixed solution; the structural formula of the rhodamine-naphthalimide material is as follows:
s3, adding the coupled cellulose membrane into the mixed solution, reacting for 24 hours at 80 ℃ in a nitrogen protective atmosphere, washing and drying the cellulose membrane with ethanol to obtain the acid discoloration intelligent cellulose membrane, wherein the structural formula of the acid discoloration intelligent cellulose membrane is as follows:
and (3) performance testing:
to 20ml of each solution at different pH, an acid-discolored smart cellulose membrane (3 cm. times.3 cm) was added and tested for performance.
The property of the acid-induced color-changing intelligent cellulose membrane prepared in the embodiment 3 is that the color depth shows good linear and gradient relation with the change of acidity in the range of pH value of 3-6 of the obtained textile. Within the pH value range of 3-6, the acid-induced discoloration intelligent cellulose membrane is obvious in discoloration and shows obvious gradient change along with the increase of acidity.
Comparative example 1
The difference from example 1 is: setting different process parameters, wherein the specific process parameters are set in step S3, and the reaction temperature is 40 ℃; the rest is the same as embodiment 1, and is not described herein again.
The performance of the intelligent acid-induced color-changing textile prepared in the comparative example 1 is that the color depth shows a certain linear and gradient relation with the change of acidity in the range of pH value of 3-6 of the obtained textile. However, the color depth is small as a whole, which is not easy to distinguish.
Comparative example 2
The difference from example 1 is: setting different process parameters, wherein the specific process parameters are that dichloroethane is adopted as the solvent in the mixed solution in the step S2; the rest is the same as embodiment 1, and is not described herein again.
The performance of the intelligent acid-induced color-changing textile prepared in the comparative example 2 is that the color depth shows a certain linear and gradient relation with the change of acidity in the range of pH value of 3-6 of the obtained textile. However, the color depth is generally shallow, which is not easy to distinguish.
Comparative example 3
The difference from example 1 is: setting different process parameters, wherein the specific process parameters are set in step S2, replacing the organic base with inorganic base, and using inorganic base potassium carbonate; the rest is the same as embodiment 1, and is not described herein again.
The performance of the intelligent acid-induced color-changing textile prepared in the comparative example 3 is that the color depth shows a certain linear and gradient relation with the change of acidity in the range of pH value of 3-6 of the obtained textile. However, the color depth is generally shallow, which is not easy to distinguish.
In conclusion, the invention provides an acid-induced color-changing intelligent textile and a preparation method thereof. The preparation method comprises the steps of taking a textile containing hydroxyl as a grafting main body, taking a rhodamine-naphthalimide fluorescent material as an acid-induced discoloration matrix, and carrying out covalent fixation on the surface of the textile grafting main body treated by a silane coupling agent through a two-step method to prepare the acid-induced discoloration and fluorescence dual-sensing intelligent textile. The acid-induced color-changing intelligent textile has the advantages of high response speed, excellent fastness and small detection interval, and can adapt to strong acid conditions; the technical defect that dye molecules are combined with a matrix through physical adsorption and electrostatic action by adopting a simple dipping or coating process in the prior art, so that the dye molecules are not combined firmly enough and easily fall off is effectively overcome; the technical defects of complex process or the need of harsh conditions such as strong acid, strong alkali, oxidation and the like in the prior art in a chemical bonding mode are overcome.
Although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof without departing from the spirit and scope of the present invention.
Claims (10)
1. A preparation method of an acid-induced color-changing intelligent textile is characterized by comprising the following steps: the method comprises the following steps:
s1, adding the hydroxyl-containing textile and an aminosilane coupling agent into ethanol according to a preset proportion, stirring for 16-40 h at room temperature, washing with ethanol, and drying for post-treatment to obtain an aminated coupled textile;
s2, adding organic base into an organic solvent according to a preset proportion, uniformly mixing, adding a rhodamine-naphthalimide material, and fully mixing to obtain a mixed solution;
s3, adding the coupled textile into the mixed solution, reacting for 18-32 hours at 70-90 ℃ in a nitrogen protective atmosphere, and cleaning and drying the reacted textile with ethanol to obtain the acid-induced color-changing intelligent textile.
2. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: the textile surface contains hydroxyl groups, and the hydroxyl groups include but are not limited to one of cotton fabrics, non-woven fabrics and regenerated cellulose fabrics.
3. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: the structural formula of the rhodamine-naphthalimide material is as follows:
Wherein, the R group is one of halogen substituent, nitro and sulfonic group.
4. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: in step S1, the mass ratio of the textile to the aminosilane coupling agent is 1: (0.8-1.6), and the concentration of the aminosilane coupling agent is 8-12%.
5. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: the amino silane coupling agent is one of aminopropyl triethoxysilane, 3-aminopropyl trimethoxysilane and N- [3- (trimethoxysilyl) propyl ] ethylenediamine.
6. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: in step S2, the organic base is one of triethylamine, N-diisopropylethylamine, triethylenediamine, and pyridine.
7. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: in step S2, the molar ratio of the organic base to the rhodamine-naphthalimide material is (5-6): 1.
8. The method for preparing acid-induced color-changing intelligent textiles according to claim 1, wherein the method comprises the following steps: the organic solvent is one of ethylene glycol methyl ether, ethylene glycol, tetrahydrofuran, dimethyl sulfoxide, nitrogen-dimethyl formamide and nitrogen, nitrogen-dimethyl acetamide.
9. A acid-induced color-changing intelligent textile prepared according to the preparation method of the acid-induced color-changing intelligent textile of any one of claims 1 to 8, characterized in that: the acid-induced color-changing intelligent textile has the structural formula as follows:
or
10. The acid-chromic smart textile according to claim 9, wherein: the acid-induced color change intelligent textile has the advantages that the color depth shows good linear and obvious gradient relation along with the change of acidity in the range of pH value of 3-6; in an acidic solution with pH 2, the intelligent fabric can change color obviously within 1s, and the color is well maintained within 24 h.
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