CN115490880B - Preparation method and application of modified lignin - Google Patents
Preparation method and application of modified lignin Download PDFInfo
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- CN115490880B CN115490880B CN202211237234.9A CN202211237234A CN115490880B CN 115490880 B CN115490880 B CN 115490880B CN 202211237234 A CN202211237234 A CN 202211237234A CN 115490880 B CN115490880 B CN 115490880B
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- 229920005610 lignin Polymers 0.000 title claims abstract description 75
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 229920001971 elastomer Polymers 0.000 claims abstract description 30
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 22
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 6
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 230000002787 reinforcement Effects 0.000 claims description 5
- -1 toluene Diisocyanamide Chemical compound 0.000 claims description 5
- 239000003929 acidic solution Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000011159 matrix material Substances 0.000 abstract description 7
- 230000003014 reinforcing effect Effects 0.000 abstract description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000005303 weighing Methods 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
Abstract
The invention relates to modified lignin, which comprises the following raw materials in parts by mass: 100 parts of lignin, 1-20 parts of modifying auxiliary agent A and 2-8 parts of modifying auxiliary agent B, wherein the modifying auxiliary agent A comprises one or more of phenol, dimethylphenol, methylphenol, terephthalic acid and bisphenol A; the modifying aid 2 comprises one or more of melamine, toluene Diisocyanato (TDI) and diphenylmethane diisocyanate (MDI). The invention also provides a preparation method of the modified lignin and application of the modified lignin in the field of rubber. The modified auxiliary agent used in the invention has higher activity, and the prepared modified lignin is easy to crosslink with a rubber macromolecular chain, so that the tensile strength and the tearing strength of the rubber matrix are improved, and the reinforcing effect of the lignin on the rubber matrix can be improved to a great extent.
Description
Technical Field
The invention relates to a preparation method and application of modified lignin, and belongs to the technical field of material chemistry.
Background
Lignin is a non-crystalline, highly branched three-dimensional network aromatic ring-containing phenolic biopolymer. Lignin is widely present in higher plant cells, and is a renewable natural polymer second to the world reserves in nature, next to cellulose. It is estimated that about 5 x 10 can be produced annually worldwide 8 -36×10 8 Tons. In the plant body, lignin, cellulose, hemicellulose and the like form a supermolecular system together, and the lignin is bonded with the cellulose to strengthen the mechanical strength of the plant body. The lignin has a complex structure, and although the complete structure of the natural lignin is not known so far, many years of researches show that the lignin contains more active groups such as aromatic groups, alcoholic hydroxyl groups, carboxyl groups, methoxy groups, conjugated double bonds and the like and has certain chemical activity. The lignin can react with materials such as rubber, plastics and the like in a grafting, crosslinking and other manners, and hydroxyl active groups in the lignin can form aromatic hydrogen bonds with pi electron clouds of conjugated double bonds in the rubber; the oxygen atoms in the methoxy, hydroxyl, carbonyl and other groups have no electron pair in common and can form lignin-metal chelate with metal ions in a coordination bond way, and the reactivity of lignin molecules is utilizedA cross-linked network structure is constructed, so that lignin plays a role in reinforcing and plasticizing.
Lignin has the above-mentioned various functional groups, but its reinforcing effect on rubber is not great, and even the strength of rubber products can be affected under certain conditions. Therefore, the lignin is modified by using the hard-segment auxiliary agent, and the modified auxiliary agent used by the invention has higher activity, is easy to crosslink a macromolecular chain of the rubber, and can greatly improve the reinforcing effect of the lignin on the rubber matrix.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to modify lignin by using a hard-segment auxiliary agent (modification auxiliary agent A), the modified lignin is easy to crosslink with a rubber macromolecular chain, and the reinforcing effect of the lignin on a rubber matrix can be improved to a great extent.
The technical scheme provided by the invention is as follows:
a modified lignin, comprising the following raw materials in parts by mass: 100 parts of lignin, 1-20 parts of modifying auxiliary agent A and 2-8 parts of modifying auxiliary agent B;
the modifying auxiliary A comprises one or more of phenol, dimethylphenol, methylphenol, terephthalic acid and bisphenol A;
the modifying additive B comprises one or more of melamine, toluene Diisocyanamide (TDI) and diphenylmethane diisocyanate (MDI).
The preparation method of the modified lignin mainly comprises the following preparation steps:
step 1: dissolving lignin in an alkaline medicament, regulating the pH value to 8-13, and heating to a reaction temperature T1;
step 2: adding a modifying auxiliary agent A to react for a certain time t1;
step 3: cooling to 50-60 ℃, adding an acidic solution, adjusting the system to be in an acidic environment, adding a modifying auxiliary agent B, heating to a temperature T2, and reacting for a period of time T2;
step 4: washing with water, oven drying, and pulverizing to obtain modified lignin.
Preferably, the alkaline agent in the step 1 is sodium hydroxide solution; the reaction temperature T1 is 80-100 ℃.
Preferably, the reaction time t1 in the step 2 is 1-2h.
Preferably, the acidic solution in step 3 comprises hydrochloric acid and/or acetic acid; the pH of the acidic environment is 3-6.
Preferably, the reaction temperature T2 in the step 3 is 70-90 ℃; the reaction time t2 is 2-3h.
Preferably, the lignin in the step 4 is washed with water and then has a pH of 6-8.
Preferably, the lignin prepared by the steps has a particle size of: d50 is less than or equal to 2 mu m, and D100 is less than or equal to 10 mu m.
The invention also provides application of the modified lignin serving as a rubber reinforcing agent in the rubber field.
In the invention, the modifying auxiliary agent A is a hard segment substance, and the reason for adding the modifying auxiliary agent A into lignin can improve the hardness of the lignin, so that the reinforcement of a rubber matrix is also improved; the modifying additive B is a functional substance, and can increase the reactivity of lignin and polysulfide, disulfide or monosulfide bonds. After modification, the functional groups in the lignin can open double bonds and sulfur bonds, and then are connected and associated to a rubber matrix, so that the reinforcing effect of the lignin on the rubber is enhanced.
Compared with the prior art, the invention has the following advantages:
1. the modified auxiliary agent used in the invention has higher unsaturation degree, and hydroxyl ions and hydrogen ions in the solvent can play a role in catalysis, thereby being beneficial to the reaction of the auxiliary agent and lignin macromolecules.
2. The modified auxiliary agent used in the invention has higher activity, and the prepared modified lignin is used as a rubber reinforcing agent, is easy to crosslink with a rubber macromolecular chain, and can improve the reinforcing effect of a rubber matrix to a great extent.
3. The papermaking waste liquid is recycled, so that the concept of green development at present is met, and the environmental protection pressure is relieved.
4. The invention uses the alkalinity of the papermaking waste liquid as a catalyst, thereby reducing the cost investment.
Detailed Description
The invention will be further illustrated with reference to the following examples, although the scope of the invention is not limited thereto.
Example 1
The preparation method of the modified lignin mainly comprises the following preparation steps:
step 1, weighing 100 parts of lignin samples, adding the lignin samples into a reaction kettle, adding sodium hydroxide solution to completely dissolve lignin, adjusting the pH value to 8, starting stirring and heating to 90 ℃;
step 2, weighing 1 part of dimethyl phenol, adding into a reaction kettle, and reacting for 1.5 hours;
step 3, cooling to 55 ℃, adding hydrochloric acid to adjust the pH of the reaction environment to 3, adding 8 parts of TDI, heating to 80 ℃, and reacting for 3 hours;
and step 4, washing 3 times with deionized water after the reaction is finished until the pH is 6, drying, and crushing.
Example 2
The preparation method of the modified lignin mainly comprises the following preparation steps:
step 1, weighing 100 parts of lignin samples, adding the lignin samples into a reaction kettle, adding sodium hydroxide solution to completely dissolve lignin, adjusting the pH value to 10, starting stirring and heating to 100 ℃;
step 2, weighing 10 parts of phenol, adding into a reaction kettle, and reacting for 2 hours;
step 3, cooling to 60 ℃, adding hydrochloric acid, adjusting the pH of the reaction environment to 4, adding 5 parts of melamine, heating to 70 ℃, and reacting for 2.5 hours;
and step 4, washing 3 times with deionized water after the reaction is finished until the pH is 8, drying, and crushing.
Example 3
The preparation method of the modified lignin mainly comprises the following preparation steps:
step 1, weighing 100 parts of lignin samples, adding the lignin samples into a reaction kettle, adding sodium hydroxide solution to completely dissolve lignin, adjusting the pH value to 13, starting stirring and heating to 80 ℃;
step 2, weighing 10 parts of methyl phenol and 10 parts of terephthalic acid, adding the mixture into a reaction kettle, and reacting for 1h;
step 3, cooling to 50 ℃, adding hydrochloric acid, adjusting the pH of the reaction environment to 6, adding 2 parts of MDI, heating to 90 ℃, and reacting for 2 hours;
and step 4, washing 3 times with deionized water after the reaction is finished until the pH is 6.5, drying, and crushing.
Example 4
Step 1, weighing 100 parts of lignin samples, adding the lignin samples into a reaction kettle, adding sodium hydroxide solution to completely dissolve lignin, adjusting the pH value to 8, starting stirring and heating to 90 ℃;
step 2, weighing 1.3 parts of bisphenol A, adding into a reaction kettle, and reacting for 1.5 hours;
step 3, cooling to 55 ℃, adding hydrochloric acid, adjusting the pH of the reaction environment to 3, adding 4 parts of melamine, heating to 80 ℃, and reacting for 3 hours;
and step 4, washing 3 times with deionized water after the reaction is finished until the pH is 7.5, drying, and crushing.
Example 5
Step 1, weighing 100 parts of lignin samples, adding the lignin samples into a reaction kettle, adding sodium hydroxide solution to completely dissolve lignin, adjusting the pH value to 10, starting stirring and heating to 100 ℃;
step 2, weighing 5 parts of methyl phenol and 7 parts of dimethyl phenol, adding into a reaction kettle, and reacting for 2 hours;
step 3, cooling to 60 ℃, adding hydrochloric acid, adjusting the pH of the reaction environment to 4, adding 2 parts of melamine and 5 parts of MDI, heating to 70 ℃, and reacting for 2.5 hours;
and step 4, washing 3 times with deionized water after the reaction is finished until the pH is 7, drying, and crushing.
Comparative example 1
The comparative example is unmodified lignin.
Effect of the invention
(1) Raw material formula for rubber preparation
The formula comprises the following components: 100 parts of natural rubber, 45 parts of carbon black, 10 parts of modified lignin/lignin, 2 parts of aromatic oil, 2 parts of stearic acid, 3 parts of zinc oxide, 1.5 parts of sulfur, 0.1 part of scorch retarder and 1.4 parts of accelerator.
(2) Preparation method
The processing technology comprises the following steps:
1. adding natural rubber into an internal mixer, and plasticating for 1min at 40 ℃;
2. adding carbon black, lignin/modified lignin, and mixing the process oil for 15min;
3. adding stearic acid, mixing zinc oxide for 10min, and placing the materials on an open mill for 4h;
4. adding the rubber compound into an internal mixer, adding sulfur, a scorch retarder and an accelerator for mixing for 3min at the temperature of 80 ℃, setting the temperature of the internal mixer to 60 ℃, carrying out thin-pass shaping on the mixed rubber compound on the internal mixer, and discharging and ageing for at most 24h.
And (3) vulcanization process: and weighing a certain mass of rubber compound, shaping and vulcanizing by using a mold with the thickness of 2mm, wherein the temperature of a vulcanizing machine is 140 ℃, the vulcanizing time is 40min, and the pressure is 10MPa.
(3) Performance test results
The tensile strength and tear strength of the samples were measured according to GB/T528-2009 and GB/T529-2008, respectively.
The rubber property data for the examples and comparative examples are shown below.
| Sample of | Tensile Strength/MPa | Tear Strength/MPa |
| Example 1 | 31.7 | 100 |
| Example 2 | 31.0 | 121.2 |
| Example 3 | 30.1 | 113.6 |
| Example 4 | 30.9 | 123.4 |
| Example 5 | 30.2 | 112.9 |
| Comparative example 1 | 28.9 | 95 |
From the above table, it can be seen that the tensile strength and tear strength of the rubber prepared by adding the modified lignin are significantly improved relative to the unmodified lignin.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (4)
1. The application of the modified lignin in rubber reinforcement is characterized in that the preparation raw materials comprise the following components in parts by mass: 100 parts of lignin, 1-20 parts of modifying auxiliary agent A and 2-8 parts of modifying auxiliary agent B;
wherein the modifying auxiliary A comprises one or a combination of a plurality of dimethylphenol, methylphenol and bisphenol A; the modifying auxiliary agent B comprises one or a combination of more of melamine, toluene Diisocyanamide (TDI) and diphenylmethane diisocyanate (MDI);
the preparation method comprises the following steps:
dissolving lignin in an alkaline reagent, regulating the pH value to 8-13, and heating to 80-100 ℃ to obtain an alkaline solution of lignin;
adding a modifying auxiliary agent A into the alkaline solution of the lignin, and reacting for 1-2h;
cooling to 50-60 ℃, adding an acidic solution, regulating the system to be in an acidic environment, adding a modifying auxiliary agent B, heating to 70-90 ℃, and reacting for 2-3 hours to obtain a pre-product;
and washing, drying and crushing the pre-product to obtain the modified lignin.
2. Use of a modified lignin according to claim 1 for rubber reinforcement wherein the alkaline agent is sodium hydroxide solution.
3. Use of a modified lignin according to claim 1 for rubber reinforcement, wherein the acidic solution comprises hydrochloric acid, acetic acid and the acidic environment has a pH of 3 to 6.
4. Use of a modified lignin according to claim 1 for rubber reinforcement, wherein the pH after the water wash is in the range of 6 to 8.
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