CN111057162A - Modified guar gum and preparation method and application thereof - Google Patents
Modified guar gum and preparation method and application thereof Download PDFInfo
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- CN111057162A CN111057162A CN201911337647.2A CN201911337647A CN111057162A CN 111057162 A CN111057162 A CN 111057162A CN 201911337647 A CN201911337647 A CN 201911337647A CN 111057162 A CN111057162 A CN 111057162A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
- C08B37/0096—Guar, guar gum, guar flour, guaran, i.e. (beta-1,4) linked D-mannose units in the main chain branched with D-galactose units in (alpha-1,6), e.g. from Cyamopsis Tetragonolobus; Derivatives thereof
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Abstract
The invention provides modified guar gum and a preparation method and application thereof. The molecular structure of the modified guar gum is shown as formula 1, wherein R is a guar gum molecule, and X is Br‑Or Cl‑(ii) a The modified guar gum is the guar gum containing the grafted chain, wherein the grafted chain is connected with guar gum molecules through a C-N bond, carbon in the C-N bond is provided by a side chain on the guar gum, and the mass percentage of the grafted chain in the modified guar gum is 0.1-0.2%. Meanwhile, the invention provides a preparation method of the modified guar gum, which comprises the steps of enabling the guar gum powder and the chlorite under the protection of nitrogen and catalysisThe sulfone is halogenated to obtain a modified guar gum precursor, and then the modified guar gum precursor and N-benzyl-N-methyldodecylamine are subjected to nitrogen alkylation reaction to obtain the product of the invention. The modified guar gum has definite bacteriostatic and bactericidal effects; the modified starch is used as a thickening agent material, does not need to be protected by adding a bactericide during production or use, and still has high viscosity retention rate.
Description
Technical Field
The invention relates to the technical field of thickening agent materials, and particularly relates to modified guar gum and a preparation method and application thereof.
Background
Guar gum is extracted from the endosperm of the seed of guar, which is native to india, pakistan, etc., and the main component is galactomannan, whose structure is a backbone formed by D-mannose linked by β -1,4 glycosidic bonds, and a multi-branched polysaccharide consisting of side chains formed by D-galactose via α -1,6 glycosidic bonds on some of the mannose, with galactose randomly distributed on the branches as seen throughout the molecule, in two or three multiples, this substantially linear, branched structure determines the guar gum behavior to be significantly different from those of unbranched, water-insoluble glucomannan, the molecular weight of guar gum is 100-200 million, the ratio of mannose to galactose is about 1:1.5-2 guar gum is readily soluble in water, forming highly viscous liquids, the viscosity of 0.6% aqueous solutions can generally reach 4000-6000mpa.s, whereas the viscosity of aqueous solutions of guar gum can reach about 48 hours at 30 ℃, the viscosity is significantly reduced due to the degradation of bacteria in the water, but the guar gum is not reported to have improved by the chemical degradation of guar gum molecules, such as hydroxypropyl methyl guar gum.
Disclosure of Invention
The invention aims to provide a modified guar gum, a preparation method and application thereof aiming at overcoming the technical defects of the prior art, so as to solve the technical problem that the modified guar gum with the structure is not available in the prior art.
The invention also aims to solve the technical problem of how to endow the guar gum with bacteriostatic and bactericidal effects by a chemical modification method.
The invention also aims to solve the technical problem of how to efficiently prepare the modified guar gum product.
Another technical problem to be solved by the present invention is how to extend the industrial use of guar or its modified products.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a modified guar gum has a molecular structure shown in formula 1:
wherein R is a guar molecule;
x is Br-Or Cl-。
Preferably, in formula 1, the rest except for R is a grafted chain, wherein the grafted chain is connected with the guar molecule through a C-N bond; the carbon in the C-N bond is provided by a side chain on the guar molecule; the mass percentage content of the grafting chain in the modified guar gum is 0.1-0.2%.
On the basis of the technical scheme, the invention further provides a preparation method of the modified guar gum, which comprises the following steps:
1) in the presence of a catalyst in a nitrogen protective atmosphere, performing a halogenation reaction on guar gum powder and thionyl chloride to obtain a modified guar gum precursor;
2) and maintaining the nitrogen protective atmosphere, and performing nitrogen alkylation reaction on the modified guar gum precursor and N-benzyl-N-methyldodecylamine to obtain the modified guar gum.
Preferably, the solvent for the halogenation reaction is dichloromethane or dichloroethane; the catalyst is N, N-Dimethylformamide (DMF) or triethylamine.
Preferably, the mass ratio of the guar gum powder, the thionyl chloride, the catalyst and the N-benzyl-N-methyldodecylamine is 1: 0.05-0.1: 0.002-0.003: 0.001-0.002.
Preferably, the temperature of the halogenation reaction is 25-50 ℃; the time of the halogenation reaction is 2-4 h.
Preferably, after the halogenation reaction is complete, the following post-treatment steps are performed: the solid was separated from the liquid and washed with dichloromethane.
Preferably, the solvent for the nitrogen alkylation reaction is tetrahydrofuran; the temperature of the nitrogen alkylation reaction is 60-80 ℃; the duration of the nitrogen alkylation reaction is 8-12 h.
Preferably, after completion of the nitrogen alkylation reaction, the following post-treatment steps are performed: solid-liquid separation, washing with 50% ethanol water solution, and drying.
On the basis of the technical scheme, the invention further provides the application of the modified guar gum as a thickening agent material.
The invention provides modified guar gum and a preparation method and application thereof. Molecules of the modified guar gumThe structure is shown as formula 1, wherein R is guar gum molecule, X is Br-Or Cl-. The modified guar gum is the guar gum containing the grafted chain, wherein the grafted chain is connected with guar gum molecules through a C-N bond, carbon in the C-N bond is provided by a side chain on the guar gum, and the mass percentage of the grafted chain in the modified guar gum is 0.1-0.2%. Meanwhile, the invention provides a preparation method of the modified guar gum, which comprises the steps of carrying out halogenation reaction on guar gum powder and thionyl chloride under the conditions of nitrogen protection and catalysis to obtain a modified guar gum precursor, and then carrying out nitrogen alkylation reaction on the modified guar gum precursor and N-benzyl-N-methyldodecylamine to obtain a product of the modified guar gum.
The molecular structure of the modified guar gum provided by the invention contains benzyl quaternary ammonium salt groups, so that the modified guar gum has exact bacteriostatic and bactericidal effects; based on the beneficial properties, the composite material is suitable as a thickening agent material, and does not need to be protected by adding a bactericide during production or use. The modified guar gum is used as a thickening agent material, and has longer viscosity retention time under the condition of not adding a bactericide; experiment verification shows that the viscosity retention rate after 48 hours reaches 98.3% under the condition of 30 ℃.
According to the invention, guar gum powder is used as a raw material, the guar gum with the bacteriostatic and bactericidal effects is synthesized, the domestic blank is filled, and the guar gum has guiding significance in the field of guar gum modification.
Detailed Description
Hereinafter, specific embodiments of the present invention will be described in detail. Well-known structures or functions may not be described in detail in the following embodiments in order to avoid unnecessarily obscuring the details. Approximating language, as used herein in the following examples, may be applied to identify quantitative representations that could permissibly vary in number without resulting in a change in the basic function. Unless defined otherwise, technical and scientific terms used in the following examples have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
A modified guar gum has a molecular structure shown in formula 1:
wherein R is a guar molecule; x is Br-Or Cl-。
In the formula 1, the rest part except R is a grafted chain, wherein the grafted chain is connected with a guar gum molecule through a C-N bond; the carbon in the C-N bond is provided by a side chain on the guar molecule; the mass percentage content of the grafting chain in the modified guar gum is 0.1-0.2%.
The grafting point of the guar gum is not particularly limited in the invention, and a plurality of hydroxyl groups in the repeating unit of the guar gum can be used as the grafting point.
The invention also provides a preparation method of the modified guar gum in the technical scheme, which comprises the following steps:
(1) under the protection of nitrogen and the action of a catalyst, performing a halogenation reaction on guar gum powder and thionyl chloride to obtain a modified guar gum precursor;
(2) and maintaining the protective atmosphere, and performing nitrogen alkylation reaction on the modified guar gum precursor and N-benzyl-N-methyldodecylamine to obtain the modified guar gum.
In a protective atmosphere, under the action of a catalyst, guar gum powder and thionyl chloride are subjected to a halogenation reaction to obtain a modified guar gum precursor. In the invention, in the halogenation reaction process, the catalyst N, N-dimethylformamide is taken as Lewis base to catalyze thionyl chloride to perform chlorination reaction with hydroxyl on the carbon atom at the 6 th position on the guar gum molecular chain.
In the present invention, the protective atmosphere is preferably a nitrogen or inert gas atmosphere. In the present invention, the protective atmosphere prevents the guar from side reactions with oxygen. In the present invention, the protective atmosphere is preferably a fluid protective atmosphere.
The source of the guar gum is not particularly limited, and the guar gum powder sold in the market can be directly purchased.
In the present invention, the catalyst is preferably N, N-dimethylformamide (i.e., DMF); the mass ratio of the guar gum to the catalyst is preferably 1: 0.002-0.003, and more preferably 1: 0.002-0.0025.
In the invention, the mass ratio of the guar gum to the thionyl chloride is preferably 1: 0.05-0.1
In the present invention, the halogenated solvent is preferably dichloromethane. The amount of the solvent is not particularly limited, and in the embodiment of the invention, the solid-to-liquid ratio of the guar gum to the solvent is preferably 1g: 10-20 mL.
In the invention, the temperature of halogenation is preferably 20-50 ℃, and more preferably 25-30 ℃; the time of the halogenation reaction is preferably 2-4 h, and more preferably 2.5-3.5 h.
The present invention is not limited to a specific sequence of addition and a specific sequence of operation of the halogenation reaction, and those skilled in the art can follow a conventional sequence of addition and operation method. In the embodiment of the invention, guar gum is preferably dissolved in a solvent, then the temperature is raised to the temperature required by the halogenation reaction in a protective atmosphere, and then a catalyst and thionyl chloride are added to carry out the halogenation reaction. The temperature rise rate of the temperature required for raising the temperature to the halogenation reaction is not particularly limited, and can be any temperature rise rate.
In the present invention, the halogenation reaction is preferably carried out under stirring; the stirring speed is not particularly limited, and the conventional speed can be adopted.
After the halogenation reaction is finished, the method preferably further comprises a first post-treatment, wherein the first post-treatment comprises solid-liquid separation, washing and drying which are sequentially carried out.
The solid-liquid separation mode in the first post-treatment is not particularly limited, and any conventional solid-liquid separation method such as suction filtration can be used. In the present invention, it is preferable that the mixed solution obtained by the radical polymerization graft reaction is naturally cooled to room temperature, and then solid-liquid separation is performed.
After the solid-liquid separation is completed, the solid matter obtained by the solid-liquid separation is preferably washed in the present invention. In the present invention, the washing can remove unreacted thionyl chloride and catalyst in the product.
In the present invention, the washing in the first post-treatment is preferably dichloromethane washing. The washing mode of the invention is not particularly limited, and the washing mode can be a conventional washing mode, such as soaking washing. The amount of washing liquid used for washing the dichloromethane is not particularly limited, and in the embodiment of the invention, the solid-to-liquid ratio of the amount of washing liquid used for washing the guar gum is preferably 1g: 1-10 mL. The number of washing times of the dichloromethane is not particularly limited, and the thionyl chloride and the catalyst can be removed, and the washing degree is based on that the thionyl chloride and the catalyst cannot be detected by thin layer chromatography (namely TLC test). After washing is completed, the modified guar gum precursor solution is preferably dried to obtain the modified guar gum precursor. The drying mode is not particularly limited, and the modified guar gum precursor with constant weight can be obtained. In the embodiment of the invention, the drying is preferably vacuum drying, and the temperature of the vacuum drying is preferably 55-60 ℃.
After the modified guar gum precursor is obtained, the protective atmosphere is maintained, and the modified guar gum precursor and N-benzyl-N-methyldodecylamine undergo a nitrogen alkylation reaction to obtain modified guar gum;
in the invention, the mass ratio of the guar gum to the N-benzyl-N-methyldodecylamine is preferably 1: 0.001-0.002.
In the present invention, the solvent for the amination reaction is preferably tetrahydrofuran. The amount of the solvent is not particularly limited, and in the embodiment of the invention, the solid-to-liquid ratio of the modified guar gum precursor to the solvent for the nitrogen alkylation reaction is preferably 1g: 1-10 mL.
In the invention, the temperature of the amination reaction is preferably 60-80 ℃, and more preferably 65-75 ℃; the time of the amination reaction is preferably 6-8 hours, and more preferably 7-8 hours.
The specific operation of the amination step is not particularly limited in the present invention, and in the embodiment of the present invention, the modified guar gum precursor and N-benzyl-N-methyldodecylamine are preferably mixed, and then heated to the temperature required for the amination reaction to perform the nitrogen alkylation reaction. The temperature rise rate of the present invention is not particularly limited, and may be any temperature rise rate.
After the nitrogen alkylation reaction is completed, the present invention preferably further comprises a second post-treatment, and the second post-treatment preferably comprises solid-liquid separation, washing and drying which are sequentially performed.
The solid-liquid separation mode in the second post-treatment is not particularly limited, and any conventional solid-liquid separation method such as suction filtration can be used in the present invention. In the invention, preferably, the mixed solution obtained by the nitrogen alkylation reaction is naturally cooled to room temperature, and then solid-liquid separation is carried out.
After the solid-liquid separation is completed, the product obtained by the solid-liquid separation is preferably washed in the invention.
In the present invention, the washing in the second post-treatment is preferably performed as 50% ethanol aqueous solution washing. In the present invention, the washing may remove N-benzyl-N-methyldodecylamine.
The number of washing with the aqueous ethanol solution is not particularly limited in the present invention, and in the examples of the present invention, the number of washing with the aqueous ethanol solution is preferably 1 more, and the number of washing with ethanol is preferably determined such that no N-benzyl-N-methyldodecylamine is detected by thin layer chromatography (i.e., TLC test).
In the present invention, the drying in the second post-treatment is not particularly limited, and any drying method known to those skilled in the art can be used to obtain a constant weight. In the embodiment of the invention, the drying is preferably vacuum drying, and the temperature of the vacuum drying is preferably 50-60 ℃.
The invention adopts the medium petrochemical standard Q/SH 10250784 to measure the bactericidal performance of the modified guar gum.
The modified guar gum and the preparation method and application thereof provided by the present invention are described in detail below with reference to the following examples, which should not be construed as limiting the scope of the present invention.
Example 1
Dispersing 10.0g of guar gum in 100mL of dichloromethane, heating to 30 ℃, stirring, introducing nitrogen to replace air in a reactor, adding 0.1g (0.84mmol) of thionyl chloride and 0.02g (0.27mmol) of catalyst DMF, stirring at constant temperature in a nitrogen atmosphere for 2.5 hours, and stopping heating; after the system is cooled to room temperature, obtaining a crude modified guar gum precursor product through suction filtration;
washing the crude product with 50mL of dichloromethane in sequence; carrying out vacuum drying on the obtained solid to obtain 10.03g of modified guar gum precursor;
mixing 10.03g of modified guar gum precursor, 0.02g (0.07mmol) of N-benzyl-N-methyldodecylamine and 50ml of N, N-dimethylformamide, introducing nitrogen for protection, and heating for 8 hours at the constant temperature of 70 ℃ in a water bath; then filtering the system to obtain a crude modified guar gum product;
washing the crude modified guar gum product with 150mL of 50% ethanol water solution for multiple times until N-benzyl-N-methyldodecylamine in a TLC detection washing liquid is washed; the washed product was dried under vacuum at 50 ℃ to constant weight to give 10.05g of modified guar.
The modified guar gum obtained in this example was tested for its antimicrobial properties using the medium petrochemical standard Q/SH 10250784 method: the viscosity retention rate of the sample after 48 hours at 30 ℃ is measured, and the viscosity retention rate is more than 96%, which indicates that the sample has better bactericidal property.
The viscosity retention of the modified guar gum obtained in this example was determined to be 98.1% using the method described above.
Example 2
The viscosity retention was determined with unmodified guar raw powder according to the medium petrochemical standard Q/SH 10250784.
The guar of this example had a viscosity retention of 65.4%.
Example 3
Modified guar was prepared by modifying the amount of N-benzyl-N-methyldodecylamine added in example 1 to 0.01g, and the other conditions were the same as in example 1.
The modified guar obtained in this example was tested for a retention of viscosity of 95.5% using the method described in example 1.
Example 4
Modified guar was prepared by modifying the amount of N-benzyl-N-methyldodecylamine added in example 1 to 0.015g, and the other conditions were the same as in example 1.
The modified guar obtained in this example was tested for viscosity retention of 97.4% using the method described in example 1.
The embodiments of the present invention have been described in detail, but the description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention. Any modification, equivalent replacement, and improvement made within the scope of the application of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The modified guar gum is characterized in that the molecular structure of the modified guar gum is shown as formula 1:
wherein R is a guar molecule;
x is Br-Or Cl-。
2. Modified guar according to claim 1, in formula 1, the rest other than R is a grafted chain, characterized in that the grafted chain is linked to the guar molecule by a C-N bond; the carbon in the C-N bond is provided by a side chain on the guar molecule; the mass percentage content of the grafting chain in the modified guar gum is 0.1-0.2%.
3. Process for the preparation of modified guar according to claim 1 or 2, characterized in that it comprises the following steps:
1) in the presence of a catalyst in a nitrogen protective atmosphere, performing a halogenation reaction on guar gum powder and thionyl chloride to obtain a modified guar gum precursor;
2) and maintaining the nitrogen protective atmosphere, and performing nitrogen alkylation reaction on the modified guar gum precursor and N-benzyl-N-methyldodecylamine to obtain the modified guar gum.
4. The process according to claim 3, wherein the solvent for the halogenation is dichloromethane or dichloroethane; the catalyst is N, N-dimethylformamide or triethylamine.
5. The preparation method according to claim 3, wherein the mass ratio of the guar gum powder, the thionyl chloride, the catalyst and the N-benzyl-N-methyldodecylamine is 1: 0.05-0.1: 0.002-0.003: 0.001-0.002.
6. The preparation method according to claim 3, wherein the temperature of the halogenation reaction is 25-50 ℃; the time of the halogenation reaction is 2-4 h.
7. The method of claim 3, wherein after completion of the halogenation reaction, the following post-treatment steps are carried out: the solid was separated from the liquid and washed with dichloromethane.
8. The process according to claim 3, wherein the solvent for the nitrogen alkylation reaction is tetrahydrofuran; the temperature of the nitrogen alkylation reaction is 60-80 ℃; the duration of the nitrogen alkylation reaction is 8-12 h.
9. A method according to claim 3, characterized in that, after the completion of the nitrogen alkylation reaction, the following post-treatment steps are carried out: solid-liquid separation, washing with 50% ethanol water solution, and drying.
10. Use of a modified guar according to claim 1 or 2 as thickener material.
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|---|---|---|---|---|
| CN114182573A (en) * | 2021-12-17 | 2022-03-15 | 广东华凯科技股份有限公司 | Antibacterial flame-retardant decorative fiber board |
| CN114182573B (en) * | 2021-12-17 | 2023-04-25 | 广东华凯科技股份有限公司 | Antibacterial flame-retardant decorative fiber board |
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| CN111057162B (en) | 2021-09-24 |
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Inventor after: Liu He Inventor after: Zhu Hu Inventor after: Song Chunliang Inventor after: Chen Haiqiang Inventor before: Liu He |