CN112825961A - Lignin feed additive and preparation method and application thereof - Google Patents

Lignin feed additive and preparation method and application thereof Download PDF

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Publication number
CN112825961A
CN112825961A CN202011314432.1A CN202011314432A CN112825961A CN 112825961 A CN112825961 A CN 112825961A CN 202011314432 A CN202011314432 A CN 202011314432A CN 112825961 A CN112825961 A CN 112825961A
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lignin
feed additive
stirring
washing
drying
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杨晓慧
李卓
景菲
胡立红
周永红
尚倩倩
贾普友
薄采颖
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Institute of Chemical Industry of Forest Products of CAF
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/20—Animal feeding-stuffs from material of animal origin
    • A23K10/26—Animal feeding-stuffs from material of animal origin from waste material, e.g. feathers, bones or skin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

A lignin feed additive and a preparation method and application thereof are disclosed, wherein 1g of lignin is suspended in 10-50 mL of molten salt hydrate according to the proportion, 50-500 mu L of inorganic acid is added, and stirring reaction is carried out for 0.5-5 h at 90-150 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of an anhydrous organic solvent, adding guanidino hydrochloride and triethylamine, stirring and reacting at 80 ℃ for 6-12 h, washing with water, and drying to obtain the lignin feed additive. The bacteriostatic study shows that: after depolymerization and guanidine modification, the bacteriostatic ability of the modified lignin is obviously enhanced, and researches show that: the inhibition rate of the compound on escherichia coli (ATCC 25922) and staphylococcus aureus (ATCC 6538) is as high as 97%. Therefore, the lignin feed additive has great application potential in the aspect of feed additives.

Description

Lignin feed additive and preparation method and application thereof
Technical Field
The invention belongs to the field of lignin treatment technology and application, and particularly relates to a lignin feed additive, a preparation method thereof and application thereof in bacteriostasis.
Background
In the breeding industry, the concept of 'breeding is more than prevention, and prevention is more than treatment' should be adhered to. With the progress of science and technology, people find that in large-scale livestock and poultry breeding, the abuse of antibiotics not only causes the residual and accumulated toxins in livestock and poultry bodies, pathogenic bacteria generate drug resistance, the immunity of animals is reduced, but also seriously threatens the health of human beings, and the search for green and harmless feed additives is urgent. Practice proves that the plant polyphenol is not easy to have harmful residue and toxic and side effects. Therefore, the plant polyphenol as the feed additive can improve the production performance of animals and prevent diseases, is a pure natural, pollution-free, residue-free and drug-resistant antibiotic substitute, and is a necessary trend for the development of the feed industry in the future.
Lignin is a complex, noncrystalline, three-dimensional network phenolic high molecular polymer, widely exists in cells of higher plants, and is one of the basic chemical compositions of coniferous trees, broad-leaved trees and grasses. Lignin, cellulose, hemicellulose and the like form a supramolecular system in plants, and the lignin is used as a binding agent of the cellulose to enhance the mechanical strength of the plants. Lignin is the second most renewable resource in nature after cellulose, and is estimated to produce about 6X 10 per year worldwide14Ton. However, lignin has a complex molecular structure and low content of active sites such as hydroxyl, resulting in low reactivity and is difficult to be utilized [ Xia Cheng Long, xu Yu Zhi, Liu Xiao Huan, Wang Chun Peng.]. At present, most of lignin is used as fuel to be burnt, and only a small amount of lignin is used for phenolic resin and polyurethaneAnd rubber [ Kosikova B, Gregorova A. journal of Applied Polymer Science,2005,97(3), 924-.]And the like in the preparation of resins and materials. The lignin is a natural high polymer containing polyphenol, and has antibacterial, anticancer, antiviral, and antioxidant effects. Therefore, the renewable lignin is used for the feed additive, so that the resource utilization of the lignin is promoted, the environmental pollution is reduced, and the sustainability of resource utilization can be improved.
However, there are some limitations to the use of lignin feed additives: firstly, the structure complexity, the heterogeneity and the polydispersity of the composite material cause the composite material to have low utilization rate and unstable performance, and more importantly, the composite material is not easy to digest and absorb by animals; in addition, lignin has a low number of free phenol-OH groups, most of which are "blocked" by methoxy and ortho groups resulting in relatively low performance. Therefore, lignin depolymerization reduces the molecular weight and polydispersity of lignin, increases the content of free hydroxyl groups, and becomes a necessary precursor basis for efficient use of lignin. However, most depolymerization processes are accompanied by a repolymerization or condensation reaction of lignin, which increases the structural complexity and heterogeneity of lignin. Acidic lithium bromide trihydrate is commonly used for dissolving and swelling cellulose and hemicellulose, and the research of the inventor finds that the acidic lithium bromide trihydrate can also effectively depolymerize lignin and is less subjected to polycondensation; more importantly, the depolymerization or demethylation of lignin can be effectively regulated and controlled by regulating and controlling reaction conditions. During the reaction process, ether bonds of each structural unit (beta-O-4, alpha-O-4, beta-beta, beta-5) of the lignin can be effectively depolymerized. In addition, guanidine groups are widely used for antibacterial materials, so that the activity of lignin is further enhanced through directional depolymerization of the lignin and modification of guanidine structures; and a series of high-activity lignin-based functional materials are screened out through activity research so as to provide a certain theoretical basis for high additional utilization of lignin.
Disclosure of Invention
The technical problem to be solved is as follows: the invention provides a lignin feed additive and a preparation method and application thereof, lignin is distributed more uniformly and has more stable performance and the reaction activity of the lignin is improved by depolymerizing or demethylating the lignin by molten salt; in addition, a guanidyl structure is introduced through a condensation reaction, so that the reactivity of the guanidyl structure is further enhanced. Research shows that in the application of bacteriostasis, the bacteriostasis performance is obviously improved, thereby providing a theoretical basis for the high added value utilization of lignin.
The technical scheme is as follows: a preparation method of a lignin feed additive is characterized by comprising the following steps: suspending 1g of lignin in 10-50 mL of molten salt hydrate according to a proportion, adding 50-500 mu L of inorganic acid, and stirring and reacting for 0.5-5 h at 90-150 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous organic solvent, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reacting for 6-12 h, washing with water, and drying to obtain the lignin feed additive.
The lignin is Kraft lignin, organic solvent type lignin or enzymolysis lignin.
The above molten salt hydrate is ZnCl2、ZnBr2、CuBr2、CaBr2LiCl or LiBr.
The inorganic acid is HCl, HBr, HNO3Or H2SO4。
The anhydrous organic solvent is tetrahydrofuran, DMF or ethanol.
The lignin feed additive prepared by the preparation method.
The application of the lignin feed additive in preparing antibacterial products.
Has the advantages that: firstly, lignin is modified by utilizing acid molten salt hydrate, so that the lignin is more uniform respectively, and the reaction activity is increased; introduction of a guanidyl structure through a condensation reaction, and further enhancement of the biological activity of the guanidyl structure through a synergistic effect; the antibacterial performance is obviously improved, and researches show that: the inhibition rate of the compound on escherichia coli (ATCC 25922) and staphylococcus aureus (ATCC 6538) is as high as 97%.
Drawings
FIG. 1 is an infrared absorption spectrum of lignin; in the infrared absorption peaks of DL, 3316 is a hydroxyl group absorption peak, and 1695 is a carbonyl (C ═ O) vibration absorption peak; among the infrared absorption peaks of LC, 3368 is a hydroxyl group absorption peak, 3200 is an N — H stretching vibration absorption peak, and 1660 is a carbon-nitrogen (C ═ N) and nitrogen-nitrogen (N ═ N) double bond vibration absorption peak. It can thus be demonstrated that the lignin side chains successfully introduce guanidino groups.
FIG. 2 is a graph comparing the antioxidant activity of lignin; l0 is unmodified lignin; DL depolymerized lignin; LC is the example 12 sample (lignin based guanidine compound); as can be seen from the graph, the radical scavenging rate of the unmodified lignin was 41.5%, the radical scavenging rate of the depolymerized lignin was 48%, and the radical scavenging rate of the lignin-based benzophenone was 54.5%. Therefore, after molten salt hydrate depolymerization and demethylation, the reactivity is increased, and the further modification is carried out to enter a benzophenone structure, so that the activity is further enhanced.
FIG. 3 is a graph comparing the bacteriostatic properties of lignin; l0 is unmodified lignin; DL depolymerizing lignin; LC is the sample of example 12 (lignin-based guanidine); as can be seen from the figure, the inhibition rates of the unmodified lignin on Escherichia coli (Escherichia coli ATCC 25922) and Staphylococcus aureus (Staphylococcus aureus ATCC 6538) are respectively 45.45% and 49.33%; after molten salt hydrate depolymerization and demethylation, the phenolic hydroxyl content is increased, the antibacterial performance is increased, and the inhibition rates are respectively 50% and 75.33%; after the guanidino group is introduced, the bacteriostatic activity of the antibacterial agent is further enhanced, and the inhibition rates of the antibacterial agent are 97.77% and 99.99%. In addition, as can be seen from fig. 3, all lignin samples had better inhibitory properties against staphylococcus aureus.
FIG. 4 is a graph comparing the inhibition of Staphylococcus aureus by lignin-based guanidine compounds; as shown, staphylococcus aureus was almost completely inhibited after the addition of 12 samples, relative to the blank sample.
Detailed Description
The preparation method of the molten salt hydrate modified lignin and the lignin feed additive comprises the following specific steps:
the method comprises the following steps: suspending 1g of lignin in 10-50 mL of molten salt hydrate according to a proportion, adding 50-500 mu L of inorganic acid, and stirring and reacting for 0.5-5 h at 90-150 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin;
step two: dissolving the modified lignin in 5mL of anhydrous organic solvent, adding guanidino hydrochloride and triethylamine, stirring at 80 ℃ for reaction for 6-12 h, washing with water, and drying to obtain a lignin feed additive;
step three: the antibacterial performance of the lignin is determined according to the national standard GB 15979-2002.
The lignin is any one or more of Kraft lignin, organic solvent type lignin or enzymatic hydrolysis lignin; the molten salt hydrate is ZnCl2、ZnBr2、CuBr2、CaBr2LiCl, LiBr, etc.; the inorganic acid is HCl, HBr and HNO3Or H2SO4Any one of (a); the anhydrous organic solvent is tetrahydrofuran, DMF or alcohol; the antibacterial performance is determined according to the national standard GB 15979-2002.
Example 1
1g of Kraft lignin suspended in 10mL ZnCl2Uniformly stirring the molten salt hydrate, adding 50 mu L of HCl, and stirring and reacting for 0.5h at 90 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous THF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 6 hours, washing with water, and drying to obtain the lignin feed additive.
Example 2
1g of Kraft lignin was suspended in 10mL CaBr2Uniformly stirring the molten salt hydrate, adding 100 mu L HBr, and stirring and reacting for 2h at 100 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 8 hours, washing with water, and drying to obtain the lignin feed additive.
Example 3
1g of Kraft lignin was suspended in 10mL of CuBr2Stirring the mixture evenly in the molten salt hydrate, and adding 150 mu L of HNO3Stirring and reacting for 1h at 120 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; dissolving the modified lignin in 5mL of absolute ethanol, and addingAdding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring and reacting for 10h at 80 ℃, washing with water, and drying to obtain the lignin feed additive.
Example 4
Suspending 1g organic solvent type lignin in 10mL LiCl molten salt hydrate, stirring well, adding 100 μ L H2SO4Stirring and reacting for 3 hours at the temperature of 130 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 12 hours, washing with water, and drying to obtain the lignin feed additive.
Example 5
Suspending 1g of enzymatic hydrolysis lignin in 10mL of LiBr molten salt hydrate, stirring uniformly, adding 250 mu L of H2SO4Stirring and reacting for 1h at 110 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous THF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 6 hours, washing with water, and drying to obtain the lignin feed additive.
Example 6
Suspending 1g of enzymatic hydrolysis lignin in 10mL of LiCl molten salt hydrate, stirring uniformly, adding 500 μ L of H2SO4Stirring and reacting for 4 hours at 150 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous THF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 6 hours, washing with water, and drying to obtain the lignin feed additive.
Example 7
1g of organosolv lignin suspended in 10mL of CuBr2Stirring the mixture evenly in the molten salt hydrate, and adding 500 mu L of HNO3Stirring and reacting for 5 hours at the temperature of 140 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 6 hours, washing with water, and drying to obtain the lignin feed additive.
Example 8
1g of Kraft lignin suspended in 30mL of ZnBr2Stirring the mixture evenly in the molten salt hydrate, and adding 300 mu L of HNO3Stirring and reacting for 2 hours at the temperature of 130 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of absolute ethanol, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 12 hours, washing with water, and drying to obtain the lignin feed additive.
Example 9
1g of Kraft lignin suspended in 50mL ZnCl2Uniformly stirring the molten salt hydrate, adding 150 mu L of HCl, and stirring and reacting for 1h at 110 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous THF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 12 hours, washing with water, and drying to obtain the lignin feed additive.
Example 10
Suspending 1g of organic solvent type lignin in 40mL of LiBr molten salt hydrate, uniformly stirring, adding 150 mu L of HBr, and stirring and reacting for 2h at 100 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous THF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 12 hours, washing with water, and drying to obtain the lignin feed additive.
Example 11
1g of enzymatically hydrolyzed lignin was suspended in 20mL of ZnBr2Uniformly stirring the molten salt hydrate, adding 200 mu L of HCl, and stirring and reacting for 0.5h at 90 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 6-12 h, washing with water, and drying to obtain the lignin feed additive.
Example 12
1g of Kraft lignin was suspended in 10mL LiBr2Uniformly stirring the molten salt hydrate, adding 250 mu L of HCl, and stirring and reacting for 1h at 100 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; then will beAnd (3) dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 12 hours, washing with water, and drying to obtain the lignin feed additive.
Studies have shown (as shown in the table below) that the nitrogen content increases after introduction of a guanidino structure by condensation reactions, and thus, it can be demonstrated that lignin introduces a guanidino structure.
Elemental analysis of modified nano-lignin
Figure BDA0002790875210000061
Example 13
1g of Kraft lignin was suspended in 30mL LiBr2The molten salt hydrate is stirred evenly and added with 300 mu L of H2SO4Stirring and reacting for 1h at 100 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 10 hours, washing with water, and drying to obtain the lignin feed additive.
Example 14
1g of Kraft lignin was suspended in 10mL LiBr2Uniformly stirring the molten salt hydrate, adding 300 mu L of HCl, and stirring and reacting for 1h at 100 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous DMF, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reaction for 6 hours, washing with water, and drying to obtain the lignin feed additive.
Example 15
Determination method of wood antioxidant activity (DPPH): DPPH free radical scavenging capacity was used to test the antioxidant capacity of various lignins. Experimental method 0.025g of lignin was dissolved in a 1, 4-dioxane to water volume ratio of 9: 1 in dioxane solution; adding 0.96mL of 0.05mg/L lignin dioxane solution into 3.54mL of 0.024g/L DPPH ethanol solution; meanwhile, a blank experiment is carried out, and the reaction is carried out for 16min at room temperature in a dark place; after the reaction is finished, measuring a light absorption value at 517nm by using an electronic ultraviolet spectrophotometer; the antioxidant capacity of the lignin to be tested is calculated according to the following formula:
DPPH (clearance) ═ A0-A1)/A0×100％
In the formula: a. the0Is the absorbance of the blank sample measured at 517nm, A1Is the absorbance at 517nm of the lignin sample being measured.
Example 16
The determination of the antibacterial performance of the lignin needs to be carried out according to the national standard GB 15979-2002. The detection principle is as follows: the test sample and the control sample are respectively added into a triangular flask with test bacterial liquid with certain concentration, the triangular flask is oscillated for a certain time at a proper temperature, the viable bacteria concentration of the bacterial liquid in the triangular flask before and after oscillation for a certain time is detected, and the antibacterial (bacteriostatic) rate is calculated, so that the antibacterial effect of the sample is evaluated.
Wherein, (1) calculation of viable bacteria concentration:
the viable bacteria concentration in each sample flask was calculated according to the formula based on the number of colonies obtained on both plates (two significant counts retained).
K＝Z×R
In the formula:
k is the viable bacteria concentration (cfu/mL) in each sample flask;
z is the average value of the number of colonies on the two plates;
and R is dilution multiple.
(2) And (3) judging the test effectiveness:
and (4) calculating the growth value F of the test bacteria according to a formula. The test was judged to be effective for bacteria such as Escherichia coli and Staphylococcus aureus when F was not less than 1.5 and the viable cell concentration in the control flask was higher than that at the time of inoculation. Otherwise, the test is invalid and needs to be carried out again.
F＝lgWt-lgWo
In the formula:
f: test bacteria growth value of the control sample;
wt: the control sample was shaken for 24h for the average viable bacteria concentration (cfu/mL) in the flask after contact;
w0: control "0" contact time mean viable bacteria concentration in flask (cfu/mL).
(3) Calculation of the antibacterial (bacteriostatic) rate:
after oscillating and contacting for 24h, comparing the viable bacteria concentration in the control sample and the sample flask, and calculating the bacteriostasis rate according to a formula.
Y＝(Wt-Qt)/Wt×100％
In the formula:
y: the antibacterial (bacteriostatic) rate of the sample;
wt: the control sample was shaken for 24h for the average viable bacteria concentration (cfu/mL) in the flask after contact;
qt, average value of viable cell concentration in flask after sample 24h shaking contact ((cfu/mL).
(4) Expression of the results:
the results were calculated as the antibacterial activity. When the calculated value of the bacteriostasis rate is negative, the calculated value is expressed as 0; when the calculated value of the bacteriostasis rate is more than or equal to 0, the value is expressed as more than or equal to 0.
The above examples are only for illustrating the technical idea and features of the present invention, and the purpose of the present invention is to enable those skilled in the art to understand the content of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.

Claims (7)

1. A preparation method of a lignin feed additive is characterized by comprising the following steps: suspending 1g of lignin in 10-50 mL of molten salt hydrate according to a proportion, adding 50-500 mu L of inorganic acid, and stirring and reacting for 0.5-5 h at 90-150 ℃; after cooling the reaction liquid, washing and drying to obtain modified lignin; and dissolving the modified lignin in 5mL of anhydrous organic solvent, adding 0.5g of guanidino hydrochloride and 0.5mL of triethylamine, stirring at 80 ℃ for reacting for 6-12 h, washing with water, and drying to obtain the lignin feed additive.
2. The method for preparing the lignin feed additive according to claim 1, wherein the lignin is Kraft lignin, organosolv lignin or enzymatic lignin.
3. The method for preparing lignin feed additive according to claim 1, wherein the molten salt hydrate is ZnCl2、ZnBr2、CuBr2、CaBr2LiCl or LiBr.
4. The method for preparing lignin feed additive according to claim 1, wherein the inorganic acid is HCl, HBr, HNO3Or H2SO4。
5. The method for preparing lignin feed additive according to claim 1, wherein the anhydrous organic solvent is tetrahydrofuran, DMF or ethanol.
6. A lignin feed additive prepared by the method of any one of claims 1 to 5.
7. Use of the lignin feed additive of claim 6 in the preparation of a bacteriostatic product.
CN202011314432.1A 2020-11-21 2020-11-21 Lignin feed additive and preparation method and application thereof Pending CN112825961A (en)

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CN113861244A (en) * 2021-09-14 2021-12-31 中国林业科学研究院林产化学工业研究所 Lignin bacteriostatic agent and preparation method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113861244A (en) * 2021-09-14 2021-12-31 中国林业科学研究院林产化学工业研究所 Lignin bacteriostatic agent and preparation method and application thereof
WO2023040251A1 (en) * 2021-09-14 2023-03-23 中国林业科学研究院林产化学工业研究所 Lignin bacteriostatic agent and preparation method therefor and application thereof

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