TWI586704B - A lignin-sugar type surfactant, preparation method and its application - Google Patents

Description

Lignin-sugar type surfactant, preparation method and application thereof

The lignin-glycotype surfactant of the invention is a reaction reaction of lignin which is biodegradable and non-toxic to human body and propylene glycol, and uses different molecular weight polyethylene glycol and maleic anhydride reactant as a spacer. a saccharide and a reaction product of lignin and a diol, wherein the saccharide is combined with a hydrophilic saccharide by a condensation reaction technique to greatly improve water solubility and exhibit excellent properties possessed by the present invention, and the present invention The lignin-glycoside surfactant has excellent dispersing ability, emulsifying ability, wettability, lubricity, and improving the luster texture characteristics. At the same time, it has the characteristics of biodegradable natural environment and can be widely used in dyeing and finishing. Cosmetics, cleaning products, pharmaceuticals, food emulsification and other related industrial uses.

In recent years, due to the rapid development of industry, there have been two serious problems affecting human survival, one is the energy crisis and the other is environmental pollution. The energy crisis is mainly caused by the large consumption of oil. The goods used by human beings are over-reliant on petroleum raw materials, resulting in a shortage of petroleum energy. Because of the petroleum-based products, many of them are not easily decomposed naturally. A large amount of waste causes serious environmental pollution on the earth. In order to reduce this phenomenon, the treatment technology of pollutants, the engineering technology to reduce pollutants and the development of decomposable raw materials are highly valued.

Therefore, environmental protection and safety are the main driving forces for the future development of the surfactant industry. It is of great significance to carry out environmental safety assessments on the possible hazards of surfactant contamination, degradation performance and cumulative performance in the environment. It is generally believed in the prior art that cationic surfactants are relatively toxic and commonly used for sterilization; anionic surfactants have certain toxicity; nonionic surfactants are relatively less toxic, but some degradation products are highly toxic. It is often discarded after use and is likely to cause environmental pollution. Therefore, in addition to considering its interface activity and functionality, it is important to assess whether environmental pollution is caused when using surfactants.

Biosurfactant is a biologically active secondary metabolite secreted by microorganisms during metabolism. It is the same as general surfactant. Biosurfactant is also transmitted through hydrophilic and hydrophobic groups. Composition, but biosurfactants have potential advantages over synthetic surfactants, including: biodegradable, non-toxic or low-toxic, with good environmental compatibility, etc., so they can be used as additives for cosmetics and pharmaceuticals; Industrial waste production to reduce industrial waste; better foaming, higher selectivity and specificity under certain environmental conditions (such as high, low temperature, pH, salt concentration); It can be used in special fields. At present, the application of biological surfactants has been involved in many fields such as petroleum, chemical industry and environment.

Decomposable surfactants, also known as temporary surfactants or controlled half-lives, are initially defined as: acid, alkali, and salt after completion of their application. The action of heat or light can be broken down into a non-interfacial active substance or a type of surfactant that is converted into a new interfacial active compound. Surfactant molecular pole The weak bond with limited stability is often contained between the sexual end and the hydrophobic chain, and the cleavage of the weak bond can directly destroy the interfacial activity of the molecule, that is, the primary decomposition of the surfactant. The decomposable surfactant can be generally classified into two types, an acetal type and a ketal type, depending on the decomposable functional group. Compared with general surfactants, decomposable surfactants have a better environmental concept, and such surfactants can eliminate some complicated situations. In recent years, people's understanding of decomposable surfactants has been deepened and developed. The magnitude of the environmental impact and the speed of biodegradability have gradually become an important indicator for judging the quality of surfactants.

The reactive surfactant refers to a surfactant having a reactive group, which not only has an interfacial activity, but also chemically reacts with the adsorbed matrix and is permanently bonded to the surface of the substrate as a part of the matrix. Two typical characteristics of reactive surfactants are: 1. It has interfacial activity, can participate in chemical reactions, and does not lose its interfacial activity after reaction; 2. In addition to hydrophilic groups and hydrophobic groups, its molecular structure There should be a reactive group. In many cases, the use of reactive emulsifiers can well solve the problems caused by traditional chemical agents, and prepare polymers with clean surfaces and functional groups. The emergence of reactive surfactants opens up new areas of surfactant synthesis and application. It can be widely used in various aspects such as emulsion polymerization, solution polymerization, dispersion polymerization, functional polymers, and preparation of nanomaterials.

Under the trend of stable development in the world, surfactants provide an excellent environment for the development of related industries, and the structure, items, performance and technical requirements of products are also getting higher and higher. Therefore, the development of safe, mild, natural, biodegradable and special surfactants provides a good foundation for the development and application of new products.

The object of the present invention is to use a natural polymer lignin as a raw material, and to modify a green environmentally friendly surfactant with a sugar, in addition to reducing the surface tension, good wettability, and emulsification and dispersion interface effect, and It has low toxicity, biodegradability and is harmless to the human body.

And the present invention can be used to increase the separation of its main components in lignocellulosic biomass. In order to avoid wasting low-value by-products and recovering solvents for the extraction of biomass raw materials, based on this point of view, lignin should not be considered as waste, but as raw materials for the production of value-added products. Green chemistry and energy reuse have great potential for development in today's society.

The lignin-glycotype surfactant of the invention is a surfactant having the structure of the general formula (I), Wherein Lignin represents a lignin residue, R ₁ and R _{2 are} simultaneously hydrogen or OCH ₃ , or each is a different hydrogen or OCH ₃ , R is a diol compound residue, and G is a saccharide residue. Wherein the diol compound is selected from the group consisting of diol compounds having a carbon number of 2 to 6, and n represents the number of repeating units of the polyoxyethylene ether segment, and the value thereof is from 10 to 5,000, wherein the saccharide compound is selected from the group consisting of a monosaccharide, a disaccharide, and a C ₄ to The oligosaccharide of C ₂₀ is selected from at least one of a polyhydroxy aldehyde, or a polyhydroxy ketone, a sugar alcohol, and a condensate thereof. Wherein the polyoxyethylene ether segment is composed of polyethylene glycol (PEG), polyethylene oxide (PEO), and polyoxyethylene (POE).

The lignin-glycotype surfactant of the present invention, wherein lignin (Lignin) is selected from the following structures Guaiacyl Syringyl Hydroxy-phenyl

The lignin-glycotype surfactant of the present invention, wherein the saccharide compound is selected from the group consisting of polyhydroxy aldehydes, or polyhydroxy ketones, sugar alcohols and condensates thereof, and comprises monosaccharides, disaccharides, such as glucose, sorbose, sorbitol. (hexyl hexaol), xylose, D-xylose, xylitol, fructose, galactose, maltose, sucrose, lactose, lactitol. The chemical formula is as follows (1)~(12):

The lignin-glycotype surfactant of the invention is a reactant A which reacts lignin with a diol compound, a reactant B which reacts maleic anhydride with polyethylene glycol, and then a reaction of reactant A with reactant B. The reactant C is obtained, and the reactant C is further reacted with a saccharide compound to obtain a product. A reactant which reacts with biodegradable, non-toxic lignin and propylene glycol, and uses a polyethylene glycol having a different molecular weight and a maleic anhydride reactant as a spacer to bind the saccharide and the reactant of the lignin and the diol. The saccharide (for example, Glucose) combines hydrophobic lignin with hydrophilic saccharide by a condensation reaction technique to greatly improve water solubility and exhibit its excellent characteristics, making it more widely used. Industrial applicability, in addition, further improves the efficiency of biodegradability. The lignin-glycotype surfactant of the invention has excellent dispersing ability, emulsifying ability, wettability, lubricity, and improving luster texture characteristics, and has the characteristics of biodegradable natural environment and can be widely used for dyeing. It has excellent industrial applicability and market substitution in the related industrial applications such as cosmetics, cleaning products, pharmaceuticals, and food emulsification.

The lignin-glycotype surfactant of the invention has wide application in the industry as a wetting and emulsifying agent because of its low cost and high application value, and because of its smoothness, oil control, long-lasting, waterproof and luster effect, It has become increasingly important in the application of pharmaceuticals and cosmetics. Lignin itself is water-insoluble, and it is still inconvenient in practical applications. The research team has modified this water-insoluble lignin with sugar, maleic anhydride and polyethylene glycol to become water-soluble with polyester. Polymer, this series of polymers has excellent interfacial properties, including surface tension, foaming, Wetness. In terms of application properties, this series of water-soluble polymers can be applied to acid dye-dyed nylon fibers as a leveling agent to increase the affinity with dyes and reduce the diffusion rate of dye-surfactant complexes.

The preparation method of the lignin-glycotype surfactant of the invention utilizes the reactant A which reacts lignin with the diol compound, the reactant B which reacts maleic anhydride with polyethylene glycol, and then reacts the reactant A with the reaction. The condensation reaction of the substance B gives the reactant C, and the reactant C is further reacted with a saccharide compound to obtain a product. A reactant which reacts with biodegradable, non-toxic lignin and propylene glycol, and uses a polyethylene glycol having a different molecular weight and a maleic anhydride reactant as a spacer to bind the saccharide and the reactant of the lignin and the diol. The saccharide (for example, Glucose) combines hydrophobic lignin with hydrophilic saccharide by a condensation reaction technique to greatly improve water solubility and exhibit its excellent characteristics, making it more widely used. Industrial applicability, in addition, further improves the efficiency of biodegradability.

Preparation of lignin-saccharide surfactant of the invention

The synthetic steps including the following (a) to (d):

(a) The lignin is reacted with the diol compound, and the catalyst is slowly heated. The reaction is carried out at 60 to 200 ° C for about 2 to 8 hours, and then cooled to about 60 to 90 ° C. The reaction is terminated by adding NaOH, and the temperature is raised to 110 °. Exhaust gas at 160 ° C to remove excess propylene glycol and water for 2 to 8 hours.

(b) reacting polyethylene glycol and an acid anhydride compound, placing in a bottle and heating to 40-80 ° C, stirring to uniformly mix the acid anhydride compound and polyethylene glycol, and then slowly adding the catalyst to 100-180 ° C, reaction 2 ~8 hours.

(c) The product of the step (a) and the product of the step (b) are placed in a reaction flask and heated to 100 to 200 ° C, and the water is removed by a water-flow evacuation.

(d) Step (C) product C and saccharide are reacted at 70 ° C to 110 ° C for 6 to 10 hours to obtain a series of crude lignin-saccharide surfactants, which are then filtered with ethanol as solvent. The unreacted material was removed, and the upper layer of the filtrate was extracted, and the solvent was removed using a vacuum concentrator to obtain a final product.

The preparation of the lignin-saccharide surfactant of the present invention, wherein the catalyst is selected from the group consisting of titanium (IV) tetraisopropoxide, sulfuric acid, hydrochloric acid or a group thereof.

The synthesis reaction formula of the lignin-glycotype surfactant of the invention is as follows: wherein the sugar is glucose and the diol compound is propylene glycol as an example.

Step1:

Step2:

Step3:

Step4:

Structural analysis of the lignin-glycotype surfactant of the present invention:

Infrared absorption spectrometer

Perkin-Elmer Spectrum One, CT, the product was concentrated, the vacuum oven was completely solvent removed, and the product was applied to a test bench in AIR to analyze and identify the functional groups of each synthesized product.

The test results are shown in Table 1 and Figure 1.

Performance analysis of the lignin-saccharide surfactant of the present invention:

Surface tension measurement

CBVP-A3, Kyowa Kaimenagaku Co. LTD., Japan., was tested using a digital pendant white gold sheet surface tension meter.

(1) First complete the calibration procedures for the instrument.

(2) Wash the platinum tablets with alcohol and pure water, then burn the platinum tablets to the fire red with alcohol lamp to cool and then hang on the hook.

(3) After washing and drying the glass culture dish, about 10 ml of the test solution is injected, and placed on a lifting platform.

(4) Start the instrument switch to make the lifting platform rise slowly. When the liquid level of the liquid to be tested touches the platinum piece, the lifting platform will automatically stop and record the surface tension value when it is stable.

(5) Repeat the above steps 3 times and find the average value. The result of this test is shown in Figure 2.

2. Determination of contact angle.

FTA, FTA-125, tested with a photographic contact angle meter.

(1) Adjust the focal length and brightness contrast of the lens to complete the calibration procedures.

(2) Prepare sample solutions of different concentrations.

(3) Select the test board to be wetted (PVC, Acrylic)

(4) The sample solution is dropped on the test board, and the screen is calculated by the computer to display the contact angle value.

(5) Repeat the procedure 3 times to measure the average value.

The result of this test is shown in Figure 3.

3. Foaming determination

Model KD-10, Daiei Kagaku Seiki MFG. Co. LTD., Japan, determined by the Ross and Miles method.

(1) Prepare 500 ml of a 1 wt% sample solution and place it in the sample tank.

(2) The fixed motor flow rate is 400ml/min. After the aqueous solution is pressed out by the circulating pump, it is continuously injected into the receiving tray through the nozzle. When the liquid reaches the certain height, the liquid will automatically overflow and maintain the liquid level to a certain height.

(3) The overflowed sample solution is automatically recycled back to the test tank for recycling. After 1 hour of circulation, the foam height in the measuring cylinder is recorded, which is the maximum foam height of the sample.

(4) Turn off the pump and record the foam height after 5 minutes. This is the foam stability.

The result of this test is shown in Figure 4.

4. Fluorescence spectrometry

Fluorescence spectrometer: Aminco-Bowman Series 2 Luminescence Spectrometer, Thermo Spectronic, Model FA-357.

(1) Fine scale 0.0101g pyrene fluorescent reagent was dissolved in 500 ml of 95% Ethanol solution, 0.2 g of pyrene-ethanol solution was weighed in a 100 ml beaker (A beaker), and Ethanol was dried in an oven at 50 °C.

(2) Prepare 20 ml of different concentration of auxiliary solution in a 100 ml beaker (B beaker).

(3) Pour 20ml of the auxiliary solution in the B beaker into the Pyrene Fluorescent Reagent of the A beaker and place it on the ultrasonic oscillator for 15 minutes.

(4) Measurement by a fluorescence spectrometer, Excitation wavelength: 335 nm, Emission wavelength: 350 to 450 nm.

The result of this test is shown in Figure 5.

5. Emulsifying ability

(1) Formulating a 1 wt% auxiliary solution.

(2) Weigh 10% by weight (O/W) of the olive oil auxiliary solution and 10% by weight (O/W) of the squalane auxiliary solution.

(3) Stirring was carried out for 10 min at a rotational speed of 11,000 rpm with a homogenizer (Ultra Turrax T25 Homogenizer), and allowed to stand for 10 min.

(4) The interface potential of each emulsion was measured by an interface potentiometer (Colloidal Dynamics, Zeta Probe Analyzer).

(5) The particle size and distribution of each emulsion droplet were measured by a Particle Size Distribution Analyzer.

The results of this test are shown in Figures 6-8.

The lignin-glycotype surfactant of the invention has excellent dispersing emulsifying ability, wet lubricity, and improving luster texture characteristics, and has the characteristics of biodegradable natural environment, and can be widely applied to dyeing and finishing, It has excellent industrial applicability and market substitution in related industrial applications such as cosmetics, cleaning products, pharmaceuticals, and food emulsification.

Figure 1. FT-IR spectrum of the lignin-saccharide surfactant of the present invention

Figure 2. Surface tension diagram of lignin-glucose surfactant and commercially available anionic and nonionic particles of the present invention.

Figure 3. Contact angle diagram of lignin-glycotype surfactant and commercially available anion and non-ion of the present invention

Figure 4. Lignin-glycophoric surfactant of the present invention and commercially available anionic and nonionic foaming diagrams

Figure 5. Fluorescence spectrum of lignin-glucose surfactant and commercially available anion and non-ion of the present invention

Figure 6. Interface potential diagram of lignin-glycophoric surfactant and commercially available anion and nonion in the present invention.

Figure 7. Initial granules of the lignin-sugar type surfactant and commercially available anionic and nonionic particles of the present invention.

Figure 8. The average particle size of the lignin-glycophoric surfactant and commercially available anionic and nonionic particles of the present invention.

Preparation of lignin-glycotype surfactant

Use materials:

(1) Lignin

structure:

(2) Propylene glycol (PG)

structure:

(3) Maleic anhydride (MA)

structure:

(4) Polyethylene glycol (PEG)

structure:

Polyoxyethylene ether segment, molecular weight: 2000, 4000, 6000, 8000, 10000 (g / mol) of polyethylene glycol (PEG)

(5) Glucose (Glucose, G)

structure:

(6) Sucrose (Sugar)

The preparation method of the lignin-saccharide surfactant of the present invention comprises the steps of synthesizing (a) to (d) as follows:

(a) 1mole lignin and propylene glycol 1mole were placed in a four-neck reaction flask equipped with a Teflon stir bar and a temperature control rod, and 1 g of catalyst: Titanium (IV) isopropoxide was added. 98%, Mw=284; C ₁₂ H ₂₈ O ₄ , ACROS) slowly warmed to about 120 ° C, the reaction was about 4 hours, then cooled to about 90 ° C, the reaction was terminated by adding about 1.5 g of NaOH, and the temperature was raised to 110-160 ° C. Excess propylene glycol and water were removed by suction and reduced pressure for about 4 hours.

(b) 1 mole of polyethylene glycol (2000, 4000, 6000, 8000, 1000) and 2 mole of maleic anhydride were placed in a reaction flask and heated to about 60 ° C to stir to uniformly mix maleic anhydride with polyethylene glycol. Thereafter, 1 g of titanium (IV) tetraisopropoxide was added to slowly raise the temperature to about 150 ° C, and the reaction was carried out for about 5 hours.

(c) Step (a) product A and step (b) product B were placed in a reaction flask to raise the temperature to about 120 ° C, and the water was removed by a water-flow evacuation to remove the external H tube and react for about 3 hours.

(d) 1 mol of step (c) product C and 1 mol of glucose or sucrose, and reacted at about 80 ° C to 90 ° C for about 8 hours to obtain a series of crude lignin-saccharide surfactants. The crude product was removed by suction filtration using ethanol as a solvent, and the upper layer of the filtrate was extracted, and the solvent was removed using a vacuum concentrator to obtain a final product.

Structural Identification Analysis of Lignin-Sugar Type Surfactant of the Invention

The structure of the lignin-glycophoric surfactant molecule synthesized by the present invention is confirmed by (FT-IR), and the infrared spectrum analysis chart mainly determines the molecular structure because all molecules have certain immobilization. The amount of energy causes the bond to stretch and bend, while the atoms oscillate and shake, causing other molecules to vibrate, while a fixed molecule can only bend or vibrate at a specific frequency equivalent to a particular energy level. When a molecule is irradiated with infrared light, the vibrating key absorbs energy only when the frequency of the light is the same as the vibration frequency of the key.

There are at v = 1720-1740cm ^-1 C = O stretching of; glycoforms infrared surfactant results of FT-IR spectroscopy have v = 2850-3000cm ^-1 absorption of stretching vibration of CH ₃ - a lignin present invention, FIG. Vibration absorption; v = 1210-1320cm ^-1 and v = 1000-1300cm ^-1 with OC stretching vibration absorption; at v = 880-995cm ^-1 with =CH stretching vibration absorption; at v = 690-900cm ^-1 CH stretching vibration absorption.

Surface tension of the lignin-glycotype surfactant of the invention

When the surfactant is added to the aqueous solution, the surface tension is lowered. Because the surfactant itself contains a hydrophilic group and a hydrophobic group, the hydrophilic group in the solution will remain in the water, while the hydrophobic group Part of it will attract the prominent water surface arrangement. Such an arrangement reduces the asymmetric hydrogen bonding force of water molecules on the surface, and reduces the surface free energy, thereby causing a decrease in surface tension.

Assuming a temperature of 25 ° C at room temperature, the surface tension value is about 72.8 mN / m, and as the concentration of the surfactant increases, the surface tension value decreases. When the concentration increase reaches a certain level, the surfactant molecules begin to attract and aggregate with the hydrophobic groups in the solution to form the micelles. When the micelles start to form, the concentration is called the critical microcell concentration (Critical Micelle Concentration; CMC). ). The surface tension diagram of the lignin-glycosurfactant of the present invention at different concentrations is known from FIG. 2. With the commercially available surfactant, the surface tension of the nonionic 1820 is the lowest, and the synthesis of the present invention. The lignin-glycosurfactant has a higher surface tension than is commercially available, and PEG 10000 has the lowest surface tension.

Contact angle of lignin-glycotype surfactant of the invention

Surfactants have the ability to reduce the surface tension and free energy of liquids, so they are wettable. The wettability of the liquid on the solid surface can be judged by the size of the contact angle.

The invention compares the relationship between the contact angle of the lignin-glycotype surfactant and the test plate by using different test plates as the wet object, and the contact angle of the water and the synthesized lignin-sugar type surfactant are obviously known from FIG. The difference in contact angle proves that the lignin-saccharide surfactant synthesized by the present invention has good wettability, and the moisturizing effect with PEG6000 is the best.

Foaming property of lignin-glycotype surfactant of the invention

Pure water does not foam, and liquids of two or more components must be present to foam. The foam (Foam) is formed by agglomeration of bubbles, which are separated from each other by a solid film or a liquid film. In terms of the surfactant, the foam is generated at a moment when the hydrophobic group of the surfactant is directed toward the inside of the bubble, and the hydrophilic group faces the absorbing film of the solution phase to form a liquid film having elasticity. Generally in liquid Surfactants are added to the body to reduce the surface tension of the bubbles and form an elastic protective film between the bubbles.

It can be seen from FIG. 4 that the lignin-saccharide surfactant synthesized by the present invention has a foaming value of about 1.2 to 2.5 cm, which shows low foaming property and foam stability, and is more general anionic or nonionic. The type of surfactant is low. The main reason is that the hydrophilic group and the hydrophobic group in the structure of the lignin-glycoactivator are arranged in a disorderly manner, and are not easily arranged neatly and closely around the bubble, that is, it is difficult to form a stable elasticity at the interface. The film is so quickly broken when the bubbles are generated, so the foaming property is low.

Fluorescent properties of the lignin-glycotype surfactant of the invention

In the micro- and micro-environment systems, the use of physical and chemical techniques in research has become an important issue. Using the fluorescent reagent P (Pyrene) to confirm the unique affinity of molecular condensation, to explore the environmental impact of radioactivity, can also be used to describe the characteristics of microcell aggregation, the main spectroscopic instrument parameters include (Excitation) and emission (Emission) spectral form, fine Vibration structure, quantum rate, and polarity in solution.

Figure 5 is a lignin-glycoside surfactant of the present invention and a commercially available anionic, nonionic fluorescence spectrum. The hydrophilicity of the product is judged by the intensity of the fluorescence, and the change in the fluorescence intensity of the product is decreased. The strength and weakness are: (SLS)>(1820)>(PEG10000)>(PEG6000)>(PEG2000), so that the synthetic lignin-glycotype surfactant can increase its fluorescence intensity with the increase of the hydrophobic end, so (PEG10000) has the highest fluorescence intensity, indicating good water solubility and lower surface tension, so it has good interfacial activity.

Emulsifying properties of the lignin-saccharide surfactant of the invention

(1) Interface potential

The most important physical property of the emulsion is emulsification stability, and its stability can be analyzed by the interface potential (Zeta potentials). When a general substance is in contact with water or another solvent, ions are adsorbed on the surface to generate a surface charge. The chargeability of the emulsion or colloid is the same as that of the general electrolyte. The difference is that the emulsion or colloid has larger particles than the electrolyte, so it has more charge than the electrolyte.

As shown in Fig. 6, the interface potential diagram of the emulsion of the lignin-glycotype surfactant as an emulsifier indicates that the absolute value of the zeta potential is: (PEG10000)>(PEG6000)>(PEG2000)>(SLS)> (1820) The larger the absolute value of the zeta potential, the greater the repulsive force between the colloidal particles, the better the dispersibility, the less likely to cause agglomeration, the better the stability of the emulsion, and the absolute interface potential as the carbon chain grows. An increase in the value indicates that the emulsion stability is better.

(2) Particle size analysis

The particle size of the emulsion is between 0.1 and 10 μm. When the particle size of the emulsion is too small, a collision occurs between the particles and the particles, which causes agglutination. The principle of this phenomenon is called Brownian Movement. On the other hand, when the emulsified particles are too large, sedimentation may occur to cause clogging or sedimentation.

The invention uses the emulsified particle size analysis of olive oil, and the initial particle size analysis thereof is shown in Fig. 7. The particle size distribution of the product is: (1820)>(SLS)>PEG10000)>(PEG2000)>(PEG6000), Among the synthesized products, the distribution peak of PEG10000 is higher and narrower than other synthetic products, indicating that the size distribution of the particles is relatively average, and the inherent good emulsion stability is shown in Fig. 8. The average emulsified particle size changes with time, and the emulsified average particle size is known. Increase with time.

Comparing the properties of the lignin-glycosurfactant product of the embodiment of the present invention with the properties of commercially available anionic and nonionic surfactants, the lignin-glycotype surfactant of the present invention is shown to be more Non-ionic surfactants have more excellent properties, such as surface tension, foaming, foam stability, emulsifying properties, etc., and can be used as a good surfactant for green and environmental protection. On the other hand, according to the embodiment of the present invention, the synthesized lignin-glucose type surfactant has the ability to reduce the surface tension of the aqueous solution, and the surface tension is preferably PEG2000. The synthesized lignin-glycophoric surfactant has a smaller contact angle than pure water and the smallest angle of PEG2000, and the relative wettability is also the best. The synthesized lignin-glycosurfactant has a foaming value of about 1.2 to 2.5 cm, has low foaming property and foam stability, and is lower than a general anionic or nonionic surfactant. The lignin-glycoside surfactant synthesized by the invention has the ability to emulsify olive oil, and the conclusion of the particle size and the interface potential is that the emulsion stability is (1820)>(SLS)>(PEG10000)>(PEG6000 )>(PEG2000). The lignin-glycosurfactant synthesized by the invention has a slightly weaker interfacial activity than the commercially available product, but its environmental hazard is more friendly than the commercially available product, so the synthesized surfactant can be assisted. Some commercially available surfactants to reduce environmental pollution.

The features, contents, advantages and advantages of the present invention will be described in detail in the embodiments of the present invention, and the descriptions used herein are merely for the purpose of illustration and description. The scope of the invention in the actual implementation is limited to the scope of the attached list.

Claims (10)

a lignin-glycotype surfactant, which is a surfactant having the structure of the general formula (I), Wherein Lignin represents a lignin residue, R ₁ and R _{2 are} simultaneously hydrogen, or OCH ₃ , or each is a different hydrogen, or OCH ₃ , R is a diol compound residue, and G is a saccharide residue, wherein The diol compound is selected from the group consisting of a diol compound having a carbon number of 2 to 6, and n represents a polyoxyethylene ether segment repeating unit number, and has a value of 10 to 5,000, wherein the saccharide residue is derived from a saccharide compound selected from monosaccharides, a disaccharide, a C ₄ to C ₂₀ oligosaccharide selected from the group consisting of at least one of a polyhydroxy aldehyde, a polyhydroxy ketone, a sugar alcohol, and an oligosaccharide thereof. A lignin-glycosurfactant according to claim 1, wherein the polyoxyethylene ether segment is selected from the group consisting of polyethylene glycol (PEG), polyethylene oxide (PEO), and polyoxyethylene. (POE). A lignin-glycosurfactant according to claim 1, wherein the saccharide compound is selected from the group consisting of glucose, fructose, maltose, sucrose, and sorbitol; wherein the lignin is at least one selected from the group consisting of the following structures; A method for preparing a lignin-glycotype surfactant as claimed in claim 1 The reactant A in which the lignin reacts with the diol compound, the reactant B in which the anhydride compound reacts with the polyethylene glycol, and the reactant A and the reactant B are condensed to obtain the reactant C, and the reactant C is further reacted with the saccharide compound. The product obtained. The preparation method of the lignin-glycosurfactant according to item 4 of the patent application scope, wherein the synthesis steps comprising (a) to (d) are as follows: (a) reacting lignin with a diol compound, adding a catalyst, The temperature is raised to 60~200 °C, the reaction is 2~8 hours, and then cooled to 60~90 °C. The reaction is terminated by adding NaOH, and the temperature is raised to 110~160 °C to extract excess propylene glycol and water and maintain for 2-8 hours. (b) reacting polyethylene glycol and an acid anhydride compound, placing in a bottle and heating to 40-80 ° C, stirring, uniformly mixing the acid anhydride compound and polyethylene glycol, adding the catalyst to the temperature of 100-180 ° C, and reacting 2-8 (c) Step (a) product A and step (b) product B, placed in a reaction flask to raise the temperature to 100 ~ 200 ° C, and use water flow evacuation to remove water; (d) step (c) The product C and the sugar are reacted at 70 ° C to 110 ° C for 6 to 10 hours to obtain a series of crude lignin-saccharide surfactants, which are then removed by ethanol filtration using ethanol as a solvent. The upper layer of the filtrate was extracted and the solvent was removed using a vacuum concentrator to give the final product. A method for preparing a lignin-glycosurfactant according to claim 4, wherein the synthetic catalyst is selected from the group consisting of titanium (IV) tetraisopropoxide, sulfuric acid, hydrochloric acid or a group thereof. A dispersant material which is a main constituent material of the lignin-glycosurfactant according to any one of claims 1 to 3. For example, the dispersant material of claim 7 is used as a fiber dyeing and finishing aid. A dispersion of inorganic nanopowder, cosmetics, pharmaceuticals, or foods. An emulsifier material which is a main constituent material of a lignin-glycosurfactant according to any one of claims 1 to 3. The emulsifier material of claim 9 is used as a cosmetic emulsifier, a food emulsifier, and a pharmaceutical emulsifier.