CN109749145B - Preparation method of modified lignin/chitosan rubber reinforced filler - Google Patents
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Abstract
The invention provides a preparation method of modified lignin/chitosan rubber reinforced filler, which comprises the following steps: s1, purifying lignin; s2, oxidizing and sulfonating lignin; s3, compounding lignin/chitosan; s4, synthesizing bis-stearoyl ethyl epoxy propyl ammonium chloride; s5, preparing the modified lignin/chitosan. The modified lignin/chitosan rubber reinforced filler has the following advantages: by modifying the chitosan and the lignin, the reaction activity is further improved, the mechanical property of the rubber is obviously improved, and the chitosan and the lignin have good synergistic effect.
Description
Technical Field
The invention relates to the field of rubber fillers, in particular to a preparation method of a modified lignin/chitosan rubber reinforced filler.
Background
Lignin is present in the xylem of most terrestrial plants, and forms the skeleton of the plant with cellulose and hemicellulose, which is a complex high molecular compound. It is generally accepted that the basic building block of lignin is phenylpropane, and there are 3 basic structures: guaiacyl propane, syringyl propane and p-hydroxyphenyl propane. The lignin has many functional groups on its structural unit, such as aromatic group, phenolic hydroxyl group, alcoholic hydroxyl group, carboxyl group, etc., and the presence of these functional groups makes the lignin have strong reactivity. The lignin can be used as an additive in rubber, and the phenolic group, the carboxyl group and other groups in the molecule of the lignin can improve the anti-aging effect of the material and the physical and mechanical properties of the material.
Chitosan (CS) is a renewable resource obtained by deacetylation of chitin to varying degrees. CS molecules have active hydroxyl and amino, have strong chemical reaction capacity, are easy to undergo reactions such as hydrolysis, alkylation, acylation, hydroxylation, grafting, quaternary ammonium salinization and the like, can generate various derivatives with different performances, and have practical foundation of combining with other substances and endowing the copolymer with self characteristics.
Natural Rubber (NR) is generally a concentrated natural latex or a granulated rubber obtained by a series of processes collected from hevea brasiliensis, and has excellent overall properties. Although CS and NR are natural polymers with unique properties and potential utility value which are very popular in material research, the mutual mixing of CS and NR can endow the new composite with respective characteristics, but can not be realized by simple mixing. The invention relates to the modification of CS as a reinforcing material.
Disclosure of Invention
The technical problem to be solved is as follows: the invention aims to provide a preparation method of modified lignin/chitosan rubber reinforced filler, and the prepared filler has a good reinforcing effect.
The technical scheme is as follows: a preparation method of modified lignin/chitosan rubber reinforced filler comprises the following steps:
s1, purifying lignin: dissolving lignin in dioxane-water solution, centrifuging to obtain centrifugate, adding diethyl ether dropwise into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 70-80 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain the oxidative sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in a dioxane-water solution, dissolving chitosan in an acetic acid water solution, mixing the two solutions, adding glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing distearyl diethylenetriamine and benzene for reaction, dripping epoxy chloropropane, stirring until the reaction is complete, and evaporating out benzene and excessive epoxy chloropropane to obtain distearamide ethyl epoxy propyl ammonium chloride;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water, heating and stirring until the lignin/chitosan composite powder is completely dissolved, adjusting the pH to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting completely under stirring, and then performing suction filtration and drying to obtain the modified lignin/chitosan.
Further, the volume ratio of dioxane to water in the step S1 is 9: 1.
Further, in the step S3, the solution prepared by dissolving the lignin prepared in the step S2 in dioxane-water is prepared into a solution with a concentration of 3%, the chitosan is dissolved in a 2-3% acetic acid aqueous solution to be prepared into a solution with a concentration of 2-5%, the two solutions are mixed according to a volume ratio of 1:0.5-1.5, 0.3-0.8% of glutaraldehyde is added for crosslinking, and finally, the solution is subjected to suction filtration at room temperature, washing and drying in an infrared box to obtain the lignin/chitosan composite powder.
Further, in the step S4, the concentration of the distearyl diethylenetriamine and the epichlorohydrin dissolved in the benzene is 0.8 to 1 mol/L.
Further, in the step S5, the lignin/chitosan composite powder prepared in the step S3 is added into deionized water to prepare a solution with a concentration of 0.5mol/L, the solution is heated to 40-50 ℃ and stirred until the solution is completely dissolved, the pH is adjusted to 10, then bis stearamide ethyl glycidyl ammonium chloride is added dropwise, the reaction is carried out for 1-3 hours under stirring, and then the modified lignin/chitosan is obtained after suction filtration and drying.
Has the advantages that: the modified lignin/chitosan rubber reinforced filler has the following advantages: by modifying the chitosan and the lignin, the reaction activity is further improved, the mechanical property of the rubber is obviously improved, and the chitosan and the lignin have good synergistic effect.
Detailed Description
Example 1
A preparation method of modified lignin/chitosan rubber reinforced filler comprises the following steps:
s1, purifying lignin: dissolving 5 times of lignin by weight in 100 times of dioxane-water solution with volume ratio of dioxane to water of 9:1, centrifuging to obtain centrifugate, dripping diethyl ether into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 70 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain oxidized and sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in dioxane-water solution to prepare a solution with the concentration of 3%, dissolving chitosan in 2% acetic acid water solution to prepare a solution with the concentration of 5%, mixing the two solutions according to the volume ratio of 1:0.5, adding 0.3% glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing distearyl diethylenetriamine and benzene for reaction, dropwise adding epoxy chloropropane, stirring until the concentration of distearyl diethylenetriamine and epoxy chloropropane dissolved in the benzene is 0.8mol/L, and evaporating the benzene and excessive epoxy chloropropane to obtain distearamide ethyl epoxy propyl ammonium chloride;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water to prepare a solution with the concentration of 0.5mol/L, heating to 40 ℃, stirring until the solution is completely dissolved, adjusting the pH value to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting for 1 hour under stirring, and performing suction filtration and drying to obtain the modified lignin/chitosan.
Example 2
A preparation method of modified lignin/chitosan rubber reinforced filler comprises the following steps:
s1, purifying lignin: dissolving 10 times of weight of lignin in 100 times of weight of dioxane-water solution, wherein the volume ratio of dioxane to water is 9:1, centrifuging to obtain centrifugate, dropwise adding diethyl ether into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 80 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain oxidized and sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in dioxane-water solution to prepare a solution with the concentration of 3%, dissolving chitosan in 3% acetic acid water solution to prepare a solution with the concentration of 2%, mixing the two solutions according to the volume ratio of 1:1.5, adding 0.8% glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing distearyl diethylenetriamine and benzene for reaction, dropwise adding epoxy chloropropane, stirring until the concentration of distearyl diethylenetriamine and epoxy chloropropane dissolved in the benzene is 1mol/L, and evaporating the benzene and excessive epoxy chloropropane after the reaction is completed to obtain distearamide ethyl epoxy propyl ammonium chloride;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water to prepare a solution with the concentration of 0.5mol/L, heating to 50 ℃, stirring until the solution is completely dissolved, adjusting the pH value to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting for 3 hours under stirring, and then carrying out suction filtration and drying to obtain the modified lignin/chitosan.
Example 3
A preparation method of modified lignin/chitosan rubber reinforced filler comprises the following steps:
s1, purifying lignin: dissolving 6 times of lignin by weight in 100 times of dioxane-water solution with the volume ratio of dioxane to water being 9:1, centrifuging to obtain centrifugate, dripping diethyl ether into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 75 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain oxidized and sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in dioxane-water solution to prepare a solution with the concentration of 3%, dissolving chitosan in 2.2% acetic acid water solution to prepare a solution with the concentration of 3-4%, mixing the two solutions according to the volume ratio of 1:1.2, adding 0.4% glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing distearyl diethylenetriamine and benzene for reaction, dropwise adding epoxy chloropropane, stirring until the concentration of distearyl diethylenetriamine and epoxy chloropropane dissolved in the benzene is 0.9mol/L, and evaporating the benzene and excessive epoxy chloropropane after the reaction is completed to obtain distearamide ethyl epoxy propyl ammonium chloride;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water to prepare a solution with the concentration of 0.5mol/L, heating to 45 ℃, stirring until the solution is completely dissolved, adjusting the pH value to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting for 2 hours under stirring, and performing suction filtration and drying to obtain the modified lignin/chitosan.
Example 4
A preparation method of modified lignin/chitosan rubber reinforced filler comprises the following steps:
s1, purifying lignin: dissolving 9 times of lignin by weight in 100 times of dioxane-water solution with the volume ratio of dioxane to water being 9:1, centrifuging to obtain centrifugate, dripping diethyl ether into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 80 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain oxidized and sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in dioxane-water solution to prepare a solution with the concentration of 3%, dissolving chitosan in 2.8% acetic acid water solution to prepare a solution with the concentration of 3-4%, mixing the two solutions according to the volume ratio of 1:0.8, adding 0.6% glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing distearyl diethylenetriamine and benzene for reaction, dropwise adding epoxy chloropropane, stirring until the concentration of distearyl diethylenetriamine and epoxy chloropropane dissolved in the benzene is 0.8mol/L, and evaporating the benzene and excessive epoxy chloropropane to obtain distearamide ethyl epoxy propyl ammonium chloride;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water to prepare a solution with the concentration of 0.5mol/L, heating to 50 ℃, stirring until the solution is completely dissolved, adjusting the pH value to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting for 3 hours under stirring, and then carrying out suction filtration and drying to obtain the modified lignin/chitosan.
Example 5
A preparation method of modified lignin/chitosan rubber reinforced filler comprises the following steps:
s1, purifying lignin: dissolving 8 times of lignin by weight in 100 times of dioxane-water solution with volume ratio of dioxane to water of 9:1, centrifuging to obtain centrifugate, dripping diethyl ether into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 78 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain oxidized and sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in dioxane-water solution to prepare a solution with the concentration of 3%, dissolving chitosan in 2.5% acetic acid water solution to prepare a solution with the concentration of 3.5%, mixing the two solutions according to the volume ratio of 1:1, adding 0.5% glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing distearyl diethylenetriamine and benzene for reaction, dropwise adding epoxy chloropropane, stirring until the concentration of distearyl diethylenetriamine and epoxy chloropropane dissolved in the benzene is 0.9mol/L, and evaporating the benzene and excessive epoxy chloropropane after the reaction is completed to obtain distearamide ethyl epoxy propyl ammonium chloride;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water to prepare a solution with the concentration of 0.5mol/L, heating to 48 ℃, stirring until the solution is completely dissolved, adjusting the pH value to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting for 2 hours under stirring, and performing suction filtration and drying to obtain the modified lignin/chitosan.
Comparative example 1
The procedure of example 1 was repeated except that no lignin was added.
Comparative example 2
The procedure of example 1 was repeated except that no chitosan was added.
The formulation of the rubber samples was as follows: 110 parts of natural rubber, 20 parts of modified lignin/chitosan rubber reinforcing filler, 30 parts of carbon black, 5 parts of stearic acid, 3 parts of ZnO, 5 parts of anti-aging agent, 2 parts of sulfur and 2 parts of vulcanization accelerator.
Physical properties: shore A hardness is measured according to GB/T531, tensile property and tear strength are respectively measured according to GB/T528 and GB/T529, and the tensile rate is 500 mm-min-1。
Claims (1)
1. A preparation method of modified lignin/chitosan rubber reinforced filler is characterized by comprising the following steps:
s1, purifying lignin: dissolving lignin in dioxane-water solution, centrifuging to obtain centrifugate, adding diethyl ether dropwise into the centrifugate to obtain precipitate, washing and drying the precipitate to obtain purified lignin, wherein the volume ratio of dioxane-water is 9: 1;
s2, oxidizing and sulfonating lignin: adding lignin into deionized water containing sodium hydroxide, heating until the lignin is completely dissolved, adjusting the pH value of the solution to 5, then adding hydrogen peroxide and ferrous sulfate for reaction, adding alkali to adjust the pH value of the solution to 9 after the reaction time is reached, adding formaldehyde and diethanol amine, reacting at 70-80 ℃, then heating to 90 ℃, adding sodium sulfite, adding acid to precipitate the lignin after the reaction is complete, washing and drying to obtain the oxidative sulfonated lignin;
s3, compounding lignin/chitosan: dissolving the lignin prepared in the step S2 in dioxane-water solution to prepare a solution with the concentration of 3%, dissolving chitosan in 2-3% acetic acid water solution to prepare a solution with the concentration of 2-5%, mixing the two solutions according to the volume ratio of 1:0.5-1.5, adding 0.3-0.8% of glutaraldehyde for crosslinking, finally performing suction filtration at room temperature, washing, and drying in an infrared box to obtain lignin/chitosan composite powder;
s4, synthesis of bis-stearoyl ethyl epoxy propyl ammonium chloride: heating and refluxing the distearyl diethylenetriamine and the benzene for reaction, dripping epichlorohydrin, stirring until the reaction is complete, and evaporating the benzene and excessive epichlorohydrin to obtain distearamide ethyl epoxypropyl ammonium chloride, wherein the concentration of the distearyl diethylenetriamine and the epichlorohydrin dissolved in the benzene is 0.8-1 mol/L;
s5, preparing modified lignin/chitosan: and (4) adding the lignin/chitosan composite powder prepared in the step (S3) into deionized water to prepare a solution with the concentration of 0.5mol/L, heating to 40-50 ℃, stirring until the solution is completely dissolved, adjusting the pH value to 10, then dropwise adding bis stearamide ethyl epoxy propyl ammonium chloride, reacting for 1-3h under stirring, and then performing suction filtration and drying to obtain the modified lignin/chitosan.
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| CN115260663B (en) * | 2022-08-11 | 2023-06-16 | 宁波艾克姆新材料股份有限公司 | Environment-friendly low-odor sealing strip and preparation method thereof |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003089506A1 (en) * | 2002-04-22 | 2003-10-30 | Purdue Research Foundation | Hydrogels having enhanced elasticity and mechanical strength properties |
| CN101322920A (en) * | 2007-06-11 | 2008-12-17 | 东北林业大学 | Method for preparing lignose chitosan reaction film |
| CN105820448A (en) * | 2016-04-21 | 2016-08-03 | 安徽伊法拉电气有限公司 | Cellulose resin rubber material |
| CN107081077A (en) * | 2017-05-12 | 2017-08-22 | 大连理工大学 | A kind of Positively charged composite nanofiltration membrane and preparation method thereof |
| CN107880325A (en) * | 2017-12-06 | 2018-04-06 | 范鸣 | A kind of 3D printing material based on modification of chitosan |
| CN108440794A (en) * | 2018-03-12 | 2018-08-24 | 华侨大学 | A kind of preparation method of chitosan nano fiber element nanometer titanium dioxide composite membrane |
| CN108642879A (en) * | 2018-05-10 | 2018-10-12 | 浙江科峰新材料有限公司 | A kind of preparation process of softening agent film |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10109386B2 (en) * | 2013-05-17 | 2018-10-23 | Heraeus Medical Components Llc | Impregnation of a non-conductive material with an intrinsically conductive polymer through in-situ polymerization |
| CN105733106A (en) * | 2016-04-25 | 2016-07-06 | 铜陵百锐设备配件有限公司 | Low-temperature-resistant and corrosion-resistant rubber sealing part |
| CN109054174A (en) * | 2018-07-13 | 2018-12-21 | 安徽义林塑业有限公司 | One kind being packed for the ageing-resistant PP composite material of high fire-retardance |
| CN108864668A (en) * | 2018-07-24 | 2018-11-23 | 常州达奥新材料科技有限公司 | A kind of high-transparency TPE class elastic toy bloom lubrication masterbatch |
| CN109749145B (en) * | 2018-11-29 | 2020-08-21 | 陶伟珍 | Preparation method of modified lignin/chitosan rubber reinforced filler |
-
2018
- 2018-11-29 CN CN201811433559.8A patent/CN109749145B/en active Active
-
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- 2019-09-25 WO PCT/CN2019/107744 patent/WO2020108057A1/en active Application Filing
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003089506A1 (en) * | 2002-04-22 | 2003-10-30 | Purdue Research Foundation | Hydrogels having enhanced elasticity and mechanical strength properties |
| CN101322920A (en) * | 2007-06-11 | 2008-12-17 | 东北林业大学 | Method for preparing lignose chitosan reaction film |
| CN105820448A (en) * | 2016-04-21 | 2016-08-03 | 安徽伊法拉电气有限公司 | Cellulose resin rubber material |
| CN107081077A (en) * | 2017-05-12 | 2017-08-22 | 大连理工大学 | A kind of Positively charged composite nanofiltration membrane and preparation method thereof |
| CN107880325A (en) * | 2017-12-06 | 2018-04-06 | 范鸣 | A kind of 3D printing material based on modification of chitosan |
| CN108440794A (en) * | 2018-03-12 | 2018-08-24 | 华侨大学 | A kind of preparation method of chitosan nano fiber element nanometer titanium dioxide composite membrane |
| CN108642879A (en) * | 2018-05-10 | 2018-10-12 | 浙江科峰新材料有限公司 | A kind of preparation process of softening agent film |
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| WO2020108057A1 (en) | 2020-06-04 |
| CN109749145A (en) | 2019-05-14 |
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