CN108559334B - Method for improving coloring performance of fluorescent dye on wood - Google Patents
Method for improving coloring performance of fluorescent dye on wood Download PDFInfo
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- CN108559334B CN108559334B CN201810379149.3A CN201810379149A CN108559334B CN 108559334 B CN108559334 B CN 108559334B CN 201810379149 A CN201810379149 A CN 201810379149A CN 108559334 B CN108559334 B CN 108559334B
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D15/00—Woodstains
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K5/00—Treating of wood not provided for in groups B27K1/00, B27K3/00
- B27K5/02—Staining or dyeing wood; Bleaching wood
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- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Forests & Forestry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
The invention relates to the technical field of wood processing treatment, and discloses a method for improving the coloring performance of a fluorescent dye on wood, wherein an active agent and metal salt are added into the fluorescent dye, a nitrogen-diacetic acid ethyl ester compound embedded with graphene oxide can form an orderly combined colloid beam, so that a dipole force effect is generated between the fluorescent dye and wood fiber, the fiber affinity is improved, the dye can permeate into the wood and has outstanding light stability and heat stability, the active agent can excite a group with absorption characteristic frequency light to generate electronic transition, the quantum yield is improved, the energy loss generated by intramolecular heat movement is reduced, the chromophore is induced to be converted into a fluorophore, and the fluorescent dye has excellent light fastness, sublimation fastness and light fastness, and in addition, the fluorescent dye can react with amino, hydroxyl, amide and other groups in the fiber for crosslinking, thereby improving the fastness to moisture.
Description
Technical Field
The invention belongs to the technical field of wood processing treatment, and particularly relates to a method for improving the coloring performance of fluorescent dye on wood.
Background
The wood product is an industrial product which takes wood or wood material as raw material and still maintains the basic characteristics of the wood after being processed by a mechanical or chemical method, and the wood product has the characteristics of light weight, good elasticity, beautiful texture, comfortable feeling, environmental friendliness, easy processing and the like, and wood resources can be recycled, so the wood product becomes one of the most important and widely applied raw materials for human beings. Among the four most commonly used materials (steel, wood, cement, plastic) in human, wood is popular with people due to its unique properties such as texture, grain, color, taste, etc.
The application of wood dyeing technology began in 1913, and since then, many scholars made a lot of researches on the basic theory and technology of wood dyeing, so that the practicality and industrialization of wood dyeing technology were rapidly developed. The wood dyeing is one aspect of improving the visual characteristics of the wood, is one of decoration approaches, and can make the wood grains more clear and more beautiful after dyeing treatment and enhance the decoration effect of the appearance color of the wood products. The current fluorescent dye is applied to each field, not only can obtain gorgeous decorative effect, has still played powerful functional effect, and is still very few in the application in wood dyeing field, and fluorescent dye only can apply paint on the timber surface to inside can not permeating timber, easily by the friction fall, the colour is very unstable, can take place to discolour and fade by illumination and climate influence.
Disclosure of Invention
The invention aims to solve the existing problems and provides a method for improving the coloring performance of fluorescent dye on wood, so that the fluorescent dye and wood fiber generate dipole force action, the fiber affinity is improved, the dye can permeate into the wood, and the optical stability and the thermal stability are outstanding.
The invention is realized by the following technical scheme:
a method for improving the coloring performance of fluorescent dye on wood comprises the steps of dissolving the fluorescent dye in an organic solvent with the volume of 2.0-2.2 times, adding a modifier accounting for 1.8-2.0% of the mass of the fluorescent dye, mixing and stirring for 30-40 minutes at 500 revolutions per minute of 400-: 12-15 parts of an active agent, 1.5-1.8 parts of metal salt, 3.0-3.5 parts of an ammonium nitrate solution, 1.0-1.5 parts of octadecanoic acid, 18-20 parts of ethanol, 0.5-0.8 part of a silane coupling agent and 1.0-1.2 parts of an auxiliary agent; the preparation method of the active agent comprises the following steps:
(1) putting a four-neck flask provided with a stirrer, a reflux condenser tube, a thermometer and a dropping funnel into a water bath, weighing 0.18-0.20 mol of N-N-diethanol aniline and 0.25-0.30 mol of phthalic acid, putting the N-N-diethanol aniline and the 0.25-0.30 mol of phthalic acid into the four-neck round-bottom flask, adding 3.5-3.8 g of graphite powder, slowly adding 15-20 ml of concentrated sulfuric acid while stirring under the ice bath condition, continuing stirring after the dripping is finished, and controlling the temperature in the flask to be within the range of 0-5 ℃;
(2) after the heat generated by the reaction is consumed and the temperature does not rise, adding 2.0-2.5 g of potassium permanganate, stirring for 30-40 minutes, dropwise adding 8-10 ml of dimethylformamide under the protection of nitrogen, heating the reaction system to 70-80 ℃ after dropwise adding, refluxing and stirring for reaction for 4-5 hours under the protection of nitrogen, naturally cooling to 25-28 ℃ after the reaction is finished, adding sodium carbonate to adjust the pH value of the system to be within the range of 6.8-7.0, placing the reaction solution in an ice water bath, standing for 20-24 hours, centrifugally washing with deionized water until no sulfate ions exist in the solution, and finally, rotationally evaporating by using a rotary evaporator to remove water.
As a further description of the above scheme, the organic solvent is capable of dissolving the corresponding fluorescent dye.
As a further description of the above scheme, the metal salt consists of the following components in mass percent: 15-20% of copper chlorate, 18-22% of manganese dichloride, 25-30% of ferric chloride and the balance of sodium chloride.
As a further description of the above scheme, the ammonium nitrate solution has a mass concentration of 40-45%.
As a further description of the above scheme, the auxiliary agent contains the following components in percentage by mass: 12-15% of defoaming agent, 20-25% of preservative, 25-30% of flatting agent and the balance of thickening agent.
As a further description of the above scheme, the particle size of the graphite powder in the step (1) is 40-50 microns.
As a further description of the scheme, the mass concentration of the concentrated sulfuric acid in the step (1) is 96-98%.
Compared with the prior art, the invention has the following advantages: in order to solve the problem of poor coloring performance of the existing fluorescent dye on wood products, the invention provides a method for improving the coloring performance of the fluorescent dye on wood, the active agent and metal salt are added into the fluorescent dye, the N, N-dimethylamino ethyl acetate compound embedded with graphene oxide can form an orderly combined colloid beam, so that the action of dipole force between the fluorescent dye and wood fiber is generated, the fiber affinity is improved, the dye can permeate into the wood, the dye has outstanding light stability and heat stability, the active agent can excite a group with light absorption characteristic frequency to generate electron transition, the quantum yield is improved, the energy loss generated by intramolecular thermal motion is reduced, the chromophore is induced to be converted into a fluorophore, and the fluorescent dye has excellent light fastness, sublimation fastness and light fastness, and can also be combined with amino groups in the fiber, The invention can improve the dye uptake of the fluorescent dye to more than 94 percent, the quantum yield is close to 1, the single photon fluorescence excitation wavelength in a fluorescence spectrogram is between 410 and 420 nanometers, the fluorescence intensity is 1.5 times higher than the prior level, the fluorescence performance is not influenced by friction, cleaning and solarization, and the application of the fluorescent compound in the field of wood is expanded.
Detailed Description
In order to make the objects, technical solutions and effects of the present invention clearer and clearer, the present invention is further described with reference to specific embodiments, and it should be understood that the specific embodiments described herein are only used for explaining the present invention and are not used for limiting the technical solutions provided by the present invention.
Example 1
A method for improving the coloring performance of fluorescent dye on wood comprises the steps of dissolving the fluorescent dye in an organic solvent with the volume being 2.0 times that of the fluorescent dye, adding a modifier accounting for 1.8 percent of the mass of the fluorescent dye, mixing and stirring for 30 minutes at the speed of 400 r/min, then placing the mixture in a water bath kettle with the temperature of 55 ℃ for heating and stirring for 1.5 hours, cooling and storing, wherein the modifier comprises the following components in parts by weight: 12 parts of active agent, 1.5 parts of metal salt, 3.0 parts of ammonium nitrate solution, 1.0 part of octadecanoic acid, 18 parts of ethanol, 0.5 part of silane coupling agent and 1.0 part of auxiliary agent; the preparation method of the active agent comprises the following steps:
(1) putting a four-neck flask provided with a stirrer, a reflux condenser tube, a thermometer and a dropping funnel into a water bath, weighing 0.18 mol of N-N-diethanol aniline and 0.25 mol of phthalic acid, putting the weighed N-N-diethanol aniline and the weighed 0.25 mol of phthalic acid into a four-neck round-bottom flask, adding 3.5 g of graphite powder, slowly adding 15 ml of concentrated sulfuric acid while stirring under the ice bath condition, continuing stirring after the dropwise addition is finished, and controlling the temperature in the flask to be within the range of 0-5 ℃;
(2) after the heat generated by the reaction is consumed and the temperature is not increased, adding 2.0 g of potassium permanganate, stirring for 30 minutes, dropwise adding 8 ml of dimethylformamide under the protection of nitrogen, heating the reaction system to 70 ℃ after dropwise adding, refluxing and stirring for reaction for 4 hours under the protection of nitrogen, naturally cooling to 25 ℃ after the reaction is finished, adding sodium carbonate to adjust the pH value of the system to be within the range of 6.8-7.0, placing the reaction solution in an ice water bath, standing for 20 hours, centrifugally washing with deionized water until no sulfate ions exist in the solution, and finally, rotationally evaporating by using a rotary evaporator to remove water.
As a further description of the above scheme, the organic solvent is capable of dissolving the corresponding fluorescent dye.
As a further description of the above scheme, the metal salt consists of the following components in mass percent: 15% of copper chlorate, 18% of manganese dichloride, 25% of ferric chloride and the balance of sodium chloride.
As a further description of the above scheme, the ammonium nitrate solution has a mass concentration of 40%.
As a further description of the above scheme, the auxiliary agent contains the following components in percentage by mass: 12% of defoaming agent, 20% of preservative, 25% of flatting agent and the balance of thickening agent.
As a further description of the above scheme, the particle size of the graphite powder in the step (1) is 40-50 microns.
As a further description of the above scheme, the concentrated sulfuric acid mass concentration in the step (1) is 96%.
Example 2
A method for improving the coloring performance of fluorescent dye on wood comprises the steps of dissolving the fluorescent dye in an organic solvent with the volume being 2.1 times that of the fluorescent dye, adding a modifier accounting for 1.9 percent of the mass of the fluorescent dye, mixing and stirring for 35 minutes at 450 revolutions per minute, then placing the mixture in a water bath kettle at 58 ℃ for heating and stirring for 1.8 hours, cooling and storing, wherein the modifier comprises the following components in parts by weight: 13 parts of active agent, 1.6 parts of metal salt, 3.3 parts of ammonium nitrate solution, 1.3 parts of octadecanoic acid, 19 parts of ethanol, 0.6 part of silane coupling agent and 1.1 parts of auxiliary agent; the preparation method of the active agent comprises the following steps:
(1) putting a four-neck flask provided with a stirrer, a reflux condenser tube, a thermometer and a dropping funnel into a water bath kettle, weighing 0.19 mol of N-N-diethanol aniline and 0.28 mol of phthalic acid, putting the weighed N-N-diethanol aniline and the weighed 0.28 mol of phthalic acid into the four-neck round-bottom flask, adding 3.6 g of graphite powder, slowly adding 18 ml of concentrated sulfuric acid while stirring under the ice bath condition, continuously stirring after the dropwise addition is finished, and controlling the temperature in the flask to be within the range of 0-5 ℃;
(2) after the heat generated by the reaction is consumed and the temperature is not increased, adding 2.2 g of potassium permanganate, stirring for 35 minutes, dropwise adding 9 ml of dimethylformamide under the protection of nitrogen, heating the reaction system to 75 ℃ after the dropwise adding is finished, refluxing and stirring for reaction for 4.5 hours under the protection of nitrogen, naturally cooling to 26 ℃ after the reaction is finished, adding sodium carbonate to adjust the pH value of the system to be within the range of 6.8-7.0, placing the reaction solution in an ice-water bath, standing for 22 hours, centrifugally washing with deionized water until no sulfate ions exist in the solution, and finally, rotationally evaporating by using a rotary evaporator to remove water.
As a further description of the above scheme, the organic solvent is capable of dissolving the corresponding fluorescent dye.
As a further description of the above scheme, the metal salt consists of the following components in mass percent: copper chlorate accounts for 18 percent, manganese dichloride accounts for 20 percent, ferric chloride accounts for 28 percent, and the rest is sodium chloride.
As a further description of the above scheme, the ammonium nitrate solution has a mass concentration of 43%.
As a further description of the above scheme, the auxiliary agent contains the following components in percentage by mass: 13% of defoaming agent, 23% of preservative, 28% of flatting agent and the balance of thickening agent.
As a further description of the above scheme, the particle size of the graphite powder in the step (1) is 40-50 microns.
As a further description of the above scheme, the mass concentration of the concentrated sulfuric acid in the step (1) is 97%.
Example 3
A method for improving the coloring performance of fluorescent dye on wood comprises the steps of dissolving the fluorescent dye in an organic solvent with the volume 2.2 times that of the fluorescent dye, adding a modifier accounting for 2.0 percent of the mass of the fluorescent dye, mixing and stirring for 40 minutes at 500 revolutions per minute, then placing the mixture in a water bath kettle with the temperature of 60 ℃, heating and stirring for 2.0 hours, cooling and storing, wherein the modifier comprises the following components in parts by weight: 15 parts of an active agent, 1.8 parts of metal salt, 3.5 parts of an ammonium nitrate solution, 1.5 parts of octadecanoic acid, 20 parts of ethanol, 0.8 part of a silane coupling agent and 1.2 parts of an auxiliary agent; the preparation method of the active agent comprises the following steps:
(1) putting a four-neck flask provided with a stirrer, a reflux condenser tube, a thermometer and a dropping funnel into a water bath, weighing 0.20 mol of N-N-diethanol aniline and 0.30 mol of phthalic acid, putting the weighed N-N-diethanol aniline and the weighed 0.30 mol of phthalic acid into a four-neck round-bottom flask, adding 3.8 g of graphite powder, slowly adding 20 ml of concentrated sulfuric acid while stirring under the ice bath condition, continuing stirring after the dropwise addition is finished, and controlling the temperature in the flask to be within the range of 0-5 ℃;
(2) after the heat generated by the reaction is consumed and the temperature is not increased, adding 2.5 g of potassium permanganate, stirring for 40 minutes, dropwise adding 10 ml of dimethylformamide under the protection of nitrogen, heating the reaction system to 80 ℃ after the dropwise adding is finished, refluxing and stirring for reaction for 5 hours under the protection of nitrogen, naturally cooling to 28 ℃ after the reaction is finished, adding sodium carbonate to adjust the pH value of the system to be within the range of 6.8-7.0, placing the reaction solution in an ice water bath, standing for 24 hours, centrifugally washing with deionized water until no sulfate ions exist in the solution, and finally, rotationally evaporating by using a rotary evaporator to remove water.
As a further description of the above scheme, the organic solvent is capable of dissolving the corresponding fluorescent dye.
As a further description of the above scheme, the metal salt consists of the following components in mass percent: 20% of copper chlorate, 22% of manganese dichloride, 30% of ferric chloride and the balance of sodium chloride.
As a further description of the above scheme, the ammonium nitrate solution has a mass concentration of 45%.
As a further description of the above scheme, the auxiliary agent contains the following components in percentage by mass: 15% of defoaming agent, 25% of preservative, 30% of flatting agent and the balance of thickening agent.
As a further description of the above scheme, the particle size of the graphite powder in the step (1) is 40-50 microns.
As a further description of the above scheme, the mass concentration of the concentrated sulfuric acid in the step (1) is 98%.
Comparative example 1
The only difference from example 1 is that the preparation addition of the active agent was omitted from the modifier, and the rest remained the same.
Comparative example 2
The only difference from example 2 is that the addition of metal salt, ammonium nitrate solution was omitted from the modifier and the rest was kept the same.
Comparative example 3
The only difference from example 3 is that the addition of graphite powder was omitted from the preparation of the active agent, and the rest remained the same.
Comparative experiment
The method of examples 1-3 and comparative examples 1-3 were used to improve the coloring performance of the fluorescent dye, while setting a comparative test without adding a modifier as a control group, keeping the independent variables of each group consistent, using rhodamine B as the fluorescent dye, ethanol as a solvent, 0.5% of the dye amount (dye to wood weight ratio), adjusting the PH value to 6.0 using a sodium acetate-acetic acid buffer solution, preparing a dye solution, with a bath ratio of 1:150, stirring for 30 minutes using a high-speed beater, sanding using a sand mill, cutting into 5 cm by 3 cm sheets using poplar sheets as the test object, dyeing at 25 ℃, 35 ℃ and 45 ℃ respectively, with the dyeing time of 60 minutes, washing with water and drying for 2-3 hours after finishing, and recording the performance results of the fluorescent dye as shown in table 1.
TABLE 1 dye uptake (%) -of fluorescent dyes at different temperatures for each set of samples
A series of experiments show that: the invention can improve the dye uptake of the fluorescent dye to more than 94 percent, the quantum yield is close to 1, the single-photon fluorescence excitation wavelength in a fluorescence spectrogram is between 410 and 420 nanometers, the fluorescence intensity is 1.5 times higher than the existing level, the fluorescence performance is not influenced by friction, cleaning and solarization, and the application of the fluorescent compound in the field of wood is expanded.
Claims (7)
1. A method for improving the coloring performance of fluorescent dye on wood is characterized in that the fluorescent dye is dissolved in an organic solvent with the volume of 2.0-2.2 times, then a modifier accounting for 1.8-2.0% of the mass of the fluorescent dye is added, the mixture is mixed and stirred for 30-40 minutes at the speed of 400 plus one year/minute, then the mixture is placed in a water bath kettle with the temperature of 55-60 ℃ for heating and stirring for 1.5-2.0 hours, and the mixture is stored after cooling, wherein the modifier comprises the following components in parts by weight: 12-15 parts of an active agent, 1.5-1.8 parts of metal salt, 3.0-3.5 parts of an ammonium nitrate solution, 1.0-1.5 parts of octadecanoic acid, 18-20 parts of ethanol, 0.5-0.8 part of a silane coupling agent and 1.0-1.2 parts of an auxiliary agent; the preparation method of the active agent comprises the following steps:
(1) putting a four-neck flask provided with a stirrer, a reflux condenser tube, a thermometer and a dropping funnel into a water bath, weighing 0.18-0.20 mol of N-N-diethanol aniline and 0.25-0.30 mol of phthalic acid, putting the N-N-diethanol aniline and the 0.25-0.30 mol of phthalic acid into the four-neck round-bottom flask, adding 3.5-3.8 g of graphite powder, slowly adding 15-20 ml of concentrated sulfuric acid while stirring under the ice bath condition, continuing stirring after the dripping is finished, and controlling the temperature in the flask to be within the range of 0-5 ℃;
(2) after the heat generated by the reaction is consumed and the temperature does not rise, adding 2.0-2.5 g of potassium permanganate, stirring for 30-40 minutes, dropwise adding 8-10 ml of dimethylformamide under the protection of nitrogen, heating the reaction system to 70-80 ℃ after dropwise adding, refluxing and stirring for reaction for 4-5 hours under the protection of nitrogen, naturally cooling to 25-28 ℃ after the reaction is finished, adding sodium carbonate to adjust the pH value of the system to be within the range of 6.8-7.0, placing the reaction solution in an ice water bath, standing for 20-24 hours, centrifugally washing with deionized water until no sulfate ions exist in the solution, and finally, rotationally evaporating by using a rotary evaporator to remove water.
2. The method of claim 1, wherein the organic solvent is capable of dissolving the fluorescent dye.
3. The method for improving the coloring performance of fluorescent dye on wood according to claim 1, wherein the metal salt comprises the following components in percentage by mass: 15-20% of copper chlorate, 18-22% of manganese dichloride, 25-30% of ferric chloride and the balance of sodium chloride.
4. The method for improving the coloring performance of fluorescent dye on wood according to claim 1, wherein the mass concentration of the ammonium nitrate solution is 40-45%.
5. The method for improving the coloring performance of the fluorescent dye on the wood according to claim 1, wherein the auxiliary agent comprises the following components in percentage by mass: 12-15% of defoaming agent, 20-25% of preservative, 25-30% of flatting agent and the balance of thickening agent.
6. The method for improving the coloring performance of fluorescent dye on wood according to claim 1, wherein the particle size of the graphite powder in the step (1) is 40-50 μm.
7. The method for improving the coloring performance of fluorescent dye on wood according to claim 1, wherein the mass concentration of the concentrated sulfuric acid in the step (1) is 96-98%.
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| GB510761A (en) * | 1937-08-25 | 1939-08-08 | British Celanese | Improvements in or relating to the colouration of artificial textile materials |
| CN105345904A (en) * | 2015-11-04 | 2016-02-24 | 安徽美景工艺品有限公司 | Oxidized graphene-silica sol enhanced pretreating agent for wicker for wickerwork and preparation method of oxidized graphene-silica sol enhanced pretreating agent |
| CN107287883A (en) * | 2017-07-26 | 2017-10-24 | 山东圣泉新材料股份有限公司 | A kind of preparation method of modified cotton fiber, obtained product and purposes |
| CN107417952A (en) * | 2017-07-28 | 2017-12-01 | 华北电力大学（保定） | A kind of cellulose fluorescent film and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB510761A (en) * | 1937-08-25 | 1939-08-08 | British Celanese | Improvements in or relating to the colouration of artificial textile materials |
| CN105345904A (en) * | 2015-11-04 | 2016-02-24 | 安徽美景工艺品有限公司 | Oxidized graphene-silica sol enhanced pretreating agent for wicker for wickerwork and preparation method of oxidized graphene-silica sol enhanced pretreating agent |
| CN107287883A (en) * | 2017-07-26 | 2017-10-24 | 山东圣泉新材料股份有限公司 | A kind of preparation method of modified cotton fiber, obtained product and purposes |
| CN107417952A (en) * | 2017-07-28 | 2017-12-01 | 华北电力大学（保定） | A kind of cellulose fluorescent film and preparation method thereof |
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