CN111892697A - Lignin-based polymer aggregate and preparation method and application thereof - Google Patents
Lignin-based polymer aggregate and preparation method and application thereof Download PDFInfo
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- CN111892697A CN111892697A CN202010735190.7A CN202010735190A CN111892697A CN 111892697 A CN111892697 A CN 111892697A CN 202010735190 A CN202010735190 A CN 202010735190A CN 111892697 A CN111892697 A CN 111892697A
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- Prior art keywords
- lignin
- based polymer
- bridged
- alkane
- ethylenedioxythiophene
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- 229920005610 lignin Polymers 0.000 title claims abstract description 67
- 229920000642 polymer Polymers 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title abstract description 19
- 239000004020 conductor Substances 0.000 claims abstract description 22
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000001338 self-assembly Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 229920001732 Lignosulfonate Polymers 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Chemical group 0.000 claims description 5
- 229910052700 potassium Chemical group 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000000502 dialysis Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 125000002081 peroxide group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 12
- 238000002347 injection Methods 0.000 abstract description 3
- 239000007924 injection Substances 0.000 abstract description 3
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 5
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 239000002088 nanocapsule Substances 0.000 description 5
- 229920005552 sodium lignosulfonate Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108010022355 Fibroins Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 229920001222 biopolymer Polymers 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000686 essence Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000473 manganese(VI) oxide Inorganic materials 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002121 nanofiber Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920002643 polyglutamic acid Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- KZDTZHQLABJVLE-UHFFFAOYSA-N 1,8-diiodooctane Chemical compound ICCCCCCCCI KZDTZHQLABJVLE-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920001046 Nanocellulose Polymers 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940045110 chitosan Drugs 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 229910052749 magnesium Chemical group 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- -1 polyphenol compounds Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229940006186 sodium polystyrene sulfonate Drugs 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/35—Macromonomers, i.e. comprising more than 10 repeat units
- C08G2261/354—Macromonomers, i.e. comprising more than 10 repeat units containing hetero atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/512—Hole transport
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/79—Post-treatment doping
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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- Y02E10/549—Organic PV cells
Abstract
The invention discloses a lignin-based polymer aggregate and a preparation method and application thereof. The lignin-based polymer aggregate is self-assembled by alkane-bridged lignin-based polymers. The lignin-based polymer aggregate has a regular structure, is simple to prepare, has wide raw material sources, is biodegradable, and can be used as a hole injection/transmission material to be doped into poly (3, 4-ethylenedioxythiophene) to prepare a conductive material, so that the conductive material has excellent energy conversion efficiency, can be applied to solar cells, and has a wide application prospect.
Description
Technical Field
The invention relates to a lignin-based polymer aggregate and a preparation method and application thereof, belonging to the technical field of natural high-molecular functional materials.
Background
The biopolymer has the characteristics of environmental protection, degradability, wide source and low cost, and can form a controllable aggregate through the self-assembly behavior of the biopolymer in a solution, and the aggregate has certain biocompatibility and degradability, can be used for loading drugs, food and the like, and arouses the strong interest of scientific researchers, for example:
CN 102058562A discloses a preparation method of gamma-polyglutamic acid/chitosan nano-capsules, which is implemented by carrying out gamma-polyglutamic acid, chitosan and Mg2+The nano capsule can be used as a medicine carrier in the pharmaceutical industry and can also be used for embedding functional food and essence;
CN 102702703A discloses a beta-PMA/gelatin nanocapsule and a preparation method thereof, the nanocapsule is prepared by self-assembly of beta-polymalic acid and gelatin, and the nanocapsule can be used for loading medicines, foods, essences and the like;
CN 102977381 a discloses a tussah silk fibroin microsphere and a preparation method thereof, wherein citric acid or acetic acid buffer solution is added into tussah silk fibroin solution, and then ultrasonic and stirring treatment is performed to prepare the tussah silk fibroin microsphere, which can be used as a carrier of bioactive substances;
CN 102924929A discloses a nanoparticle for encapsulating polyphenol active substances and a preparation method thereof, wherein a covalent conjugate is obtained by the reaction of protein and polysaccharide, and then the covalent conjugate and polyphenol compounds are self-assembled in an aqueous solution through a non-covalent bond acting force to prepare the nanoparticle, and the nanoparticle has high encapsulation efficiency, high loading capacity and good protective activity on the polyphenol active substances;
CN 101700235A discloses a self-assembly compound film-controlled slow-release preparation and a preparation method thereof, wherein skeleton type tablets or granules are prepared by biological polymers (such as chitosan, sodium alginate, carrageenan, sodium carboxymethylcellulose and the like) with different charges, then the skeleton type tablets or granules and the biological polymers with different charges interact to form insoluble compound films, and a skeleton system is automatically converted into the self-assembly compound film-controlled slow-release tablets or granules;
CN 101528052A discloses an aerated food and a preparation method thereof, wherein the aerated food in a stable foam form is prepared by assembling cellulose and surface active particles under the mutual attraction action of an air-water interface;
CN 102000363A discloses a preparation method of CA/CS/CNTs composite nanofiber with good biocompatibility, which comprises the step of soaking a nano cellulose membrane prepared from cellulose acetate in prepared chitosan and carbon nanotube liquid for self-assembly to prepare the composite nanofiber with high porosity and good biocompatibility.
Lignin is a biopolymer which is rich in sources in nature, has a complex structure, and the research on preparing nano/micron materials through the aggregation behavior of lignin in a solution is very little, so that the lignin needs to be developed and utilized.
Disclosure of Invention
The invention aims to provide a lignin-based polymer aggregate and a preparation method and application thereof.
The technical scheme adopted by the invention is as follows:
a lignin-based polymer aggregate is formed by self-assembling alkane-bridged lignin-based polymers; the alkane-bridged lignin-based polymer has the structural formula:
Preferably, the weight average molecular weight of the alkane-bridged lignin-based polymer is 5000-500000 Da.
Further preferably, the alkane-bridged lignin-based polymer has a weight average molecular weight of 10000 to 100000 Da.
Preferably, the lignin-based polymer aggregates are polyhedrons.
More preferably, the lignin-based polymer aggregate is one of a cube and a cuboid, and the side length is 0.01-10 μm.
The preparation method of the lignin-based polymer aggregate comprises the following steps: dispersing the alkane-bridged lignin-based polymer in water, adding an organic solvent to obtain a mixed solution, stirring, and standing to obtain the lignin-based polymer aggregate.
Preferably, the organic solvent is at least one of tetrahydrofuran, dioxane, dimethyl sulfoxide, dimethylformamide, methanol, ethanol, isopropanol, n-butanol and acetone.
Preferably, the volume ratio of the water to the organic solvent is 1: (0.01-9).
More preferably, the volume ratio of the water to the organic solvent is 1: (3-7).
Preferably, the concentration of the alkane-bridged lignin-based polymer in the mixed solution is 0.1-100 g/L.
Further preferably, the concentration of the alkane-bridged lignin-based polymer in the mixed solution is 0.1-10 g/L.
The poly 3, 4-ethylenedioxythiophene conductive material is doped with the lignin-based polymer aggregate.
The preparation method of the poly 3, 4-ethylenedioxythiophene conductive material comprises the following steps: dispersing the alkane-bridged lignin-based polymer in water, adding 3, 4-ethylenedioxythiophene, adjusting the pH of the system to 1-4, stirring, adding an initiator, stirring for reaction, and dialyzing by using a dialysis bag to remove salt to obtain a poly-3, 4-ethylenedioxythiophene conductive material; the alkane-bridged lignin-based polymer has the structural formula:
Preferably, the initiator is a peroxide initiator.
Further preferably, the initiator is at least one of ammonium persulfate, sodium persulfate and potassium persulfate.
A solar cell comprises the poly 3, 4-ethylenedioxythiophene conductive material.
The invention has the beneficial effects that: the lignin-based polymer aggregate has a regular structure, is simple to prepare, has wide raw material sources, is biodegradable, and can be used as a hole injection/transmission material to be doped into poly (3, 4-ethylenedioxythiophene) to prepare a conductive material, so that the conductive material has excellent energy conversion efficiency, can be applied to solar cells, and has a wide application prospect.
Drawings
Fig. 1 is an SEM image of the lignin-based polymer aggregate in example 1.
Fig. 2 is an SEM image of the lignin-based polymer aggregate in example 2.
Fig. 3 is an SEM image of the lignin-based polymer aggregate in example 3.
Fig. 4 is a graph of the hole mobility test results for the alkane-bridged lignin-based polymers of examples 1 and 2.
FIG. 5 is a UV spectrum of the poly (3, 4-ethylenedioxythiophene) conductive materials of examples 4 and 5.
Fig. 6 is a performance test chart of the poly 3, 4-ethylenedioxythiophene conductive material used in the solar cell in example 4 and example 5.
Detailed Description
The invention will be further explained and illustrated with reference to specific examples.
Example 1:
a lignin-based polymer aggregate, the method of making comprising the steps of:
1) dispersing 20g of sodium lignosulfonate in 150mL of water, and then adding 10g of potassium carbonate and 10g of tetrabutylammonium bromide to obtain an intermediate reaction solution A; adding 10g of 1, 6-dibromohexane into a reaction bottle, slowly dropping the reaction solution A into the reaction bottle at 60 ℃ by using a constant-pressure dropping funnel, finishing dropping for 1h, reacting at 90 ℃ for 10h after finishing dropping, cooling to room temperature, purifying and drying to obtain an alkane bridged lignin-based polymer (ASL-1, with the weight-average molecular weight of 60000 Da);
2) preparing a 1g/L aqueous solution of the alkane-bridged lignin-based polymer, adding 5mL of the aqueous solution into 5mL of water, adding 50mL of acetone, stirring for 4h, and standing to obtain a lignin-based polymer aggregate.
Example 2:
a lignin-based polymer aggregate, the method of making comprising the steps of:
1) dispersing 20g of sodium lignosulfonate in 100mL of water, adding 2g of sodium hydroxide and 0.5g of potassium iodide, heating to 60 ℃, slowly injecting 100g of 1, 2-dibromoethane by using a syringe, completing the addition for 1.5h, reacting for 24h at 60 ℃, cooling to room temperature, purifying and drying to obtain an alkane bridged lignin-based polymer (ASL-2, weight average molecular weight of 20000 Da);
2) preparing 10g/L aqueous solution of the alkane-bridged lignin-based polymer, adding 10mL of the aqueous solution into 70mL of ethanol, stirring for 4h, and standing to obtain the lignin-based polymer aggregate.
Example 3:
a lignin-based polymer aggregate, the method of making comprising the steps of:
1) dispersing 20g of sodium lignosulfonate in 200mL of water, adding 4g of potassium hydroxide and 2g of sodium iodide, heating to 60 ℃, slowly injecting 1g of 1, 10-dibromosunflower alkane by using a syringe, adding the 1, 10-dibromosunflower alkane for 0.5h, reacting for 4h at 100 ℃, cooling to room temperature, purifying and drying to obtain an alkane bridged lignin-based polymer (ASL-3, weight average molecular weight of 150000 Da);
2) preparing the alkane-bridged lignin-based polymer into 0.5g/L aqueous solution, adding 50mL of the aqueous solution into 150mL of dioxane, stirring for 3h, and standing to obtain the lignin-based polymer aggregate.
Example 4:
a poly 3, 4-ethylenedioxythiophene conductive material and a preparation method thereof comprise the following steps:
dispersing 5g of alkane bridged lignin-based polymer (same as example 1) in 150mL of water, adding 5g of 3, 4-ethylenedioxythiophene, adjusting the pH of the system to 2 with hydrochloric acid, stirring for 0.5h, dropwise adding 50mL of ammonium persulfate aqueous solution (containing 9.6g of ammonium persulfate) by using a peristaltic pump, stirring for 24h after dropwise adding, and dialyzing and desalting by using a dialysis bag with the molecular weight of 1000Da to obtain the poly-3, 4-ethylenedioxythiophene conductive material (PEDOT: ASL).
Example 5:
a poly 3, 4-ethylenedioxythiophene conductive material and a preparation method thereof comprise the following steps:
dispersing 5g of alkane bridged lignin-based polymer (same as example 2) in 180mL of water, adding 5g of 3, 4-ethylenedioxythiophene, adjusting the pH of the system to 2 with hydrochloric acid, stirring for 0.5h, dropwise adding 50mL of ammonium persulfate aqueous solution (containing 9.6g of ammonium persulfate) by using a peristaltic pump, completing dropwise adding for 1.5h, stirring for 24h after completing dropwise adding, and dialyzing by using a dialysis bag with the molecular weight of 1000Da for desalting to obtain the poly-3, 4-ethylenedioxythiophene conductive material (PEDOT: ASL).
Note:
the preparation method of the alkane-bridged lignin-based polymer in the present invention is referred to CN 104004200 a.
The same effect can be obtained by replacing sodium lignosulfonate with potassium lignosulfonate.
And (3) performance testing:
1) SEM images of the lignin-based polymer aggregates of examples 1 to 3 are shown in FIGS. 1 to 3, respectively.
As can be seen from FIGS. 1 to 3: the alkane-bridged lignin-based polymer self-assembles in solution through aggregation behavior to obtain aggregates (including cubes and cuboids) with extremely regular shapes.
2) The alkane-bridged lignin-based polymers of examples 1 and 2 were prepared as ITO/MnO as a hole transport material (HTL)3/HTL/MnO3Single-hole component of/Al structure (ITO layer, MnO)3Layer, HTL layer, MnO3The thickness of each layer and the Al layer was 10nm), and the hole mobility was measured, and the test results are shown in fig. 4.
As can be seen from fig. 4: the alkane-bridged lignin-based polymer has higher mobility, mainly the strong aggregation behavior and the electron migration caused by phenolic hydroxyl groups on lignin molecules, so the alkane-bridged lignin-based polymer can be used as a hole injection/transport material.
3) The ultraviolet spectrums of the poly 3, 4-ethylenedioxythiophene conductive materials of examples 4 and 5 are shown in FIG. 5.
As can be seen from fig. 5: the absorption peaks at 220nm and 280nm are ultraviolet absorption peaks of sodium lignosulfonate, and the absorption peaks at 600-900 nm are ultraviolet absorption broad peaks of PEDOT, which indicates that the PEDOT and ASL conductive material is successfully prepared.
4) Testing the device performance of the solar cell: PTB7 and PTB7-Th are adopted as donor materials, PC71BM is an acceptor material and is taken as the activity of the polymer solar cell by blending the BM and the acceptor materialThe structure of the battery device is ITO/HTL/PTB7: PC71BM/Al. The preparation process comprises the following steps: spin-coating a hole transport layer material with a thickness of 20nm on the treated ITO conductive glass, annealing at 120 deg.C for 20min, and placing the active layer material PTB7: PC in a glove box under nitrogen atmosphere71A mixed solution of chloroform and 1, 8-diiodooctane of BM is spin-coated on the hole transport layer and then is lower than 5 × 10-4Evaporating an Al electrode with the thickness of 100nm under the vacuum condition of Pa, and controlling the effective device area to be 0.16cm2The current-voltage characteristics of the device are tested by using a Keithley2400 test unit, and the light intensity is 100mW/cm2Next, the photovoltaic device was calibrated using an AM 1.5G solar simulator (Orielmodel 91192).
The performance test chart of the solar cell device prepared by using the poly 3, 4-ethylenedioxythiophene conductive material in the embodiments 4 and 5 as the hole transport layer material is shown in fig. 6, and the performance parameters are shown in the following table:
TABLE 1 Performance parameters Table for solar cell devices
Note:
PEDOT and PEDOT PSS-4083 are both commercially available products.
As can be seen from fig. 6: the performance of the P-type PEDOT material prepared by doping ASL is very close to that of a commercial PEDOT/PSS-4083 product, and particularly the PEDOT/ASL material in the embodiment 4 can be applied to organic photoelectric devices instead of sodium polystyrene sulfonate PSS.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A lignin-based polymer aggregate characterized by: the self-assembly is formed by self-assembly of alkane-bridged lignin-based polymers; the alkane-bridged lignin-based polymer has the structural formula:
2. The lignin-based polymer aggregate according to claim 1, characterized in that: the weight average molecular weight of the alkane-bridged lignin-based polymer is 5000-500000 Da.
3. The method for producing lignin-based polymer aggregates according to claim 1 or 2, characterized in that: the method comprises the following steps: dispersing the alkane-bridged lignin-based polymer in water, adding an organic solvent to obtain a mixed solution, stirring, and standing to obtain the lignin-based polymer aggregate.
4. The method of producing lignin-based polymer aggregates according to claim 3, characterized in that: the organic solvent is at least one of tetrahydrofuran, dioxane, dimethyl sulfoxide, dimethylformamide, methanol, ethanol, isopropanol, n-butanol and acetone.
5. The method for producing lignin-based polymer aggregates according to claim 3 or 4, characterized in that: the volume ratio of the water to the organic solvent is 1: (0.01-9).
6. The method for producing lignin-based polymer aggregates according to claim 3 or 4, characterized in that: the concentration of the alkane-bridged lignin-based polymer in the mixed solution is 0.1-100 g/L.
7. A poly 3, 4-ethylenedioxythiophene conductive material is characterized in that: doped with the lignin-based polymer aggregate of claim 1 or 2.
8. The method for preparing a poly (3, 4-ethylenedioxythiophene) conductive material according to claim 7, wherein: the method comprises the following steps: dispersing the alkane-bridged lignin-based polymer in water, adding 3, 4-ethylenedioxythiophene, adjusting the pH of the system to 1-4, stirring, adding an initiator, stirring for reaction, and dialyzing by using a dialysis bag to remove salt to obtain a poly-3, 4-ethylenedioxythiophene conductive material; the alkane-bridged lignin-based polymer has the structural formula:
9. The method for preparing the poly 3, 4-ethylenedioxythiophene conductive material according to claim 8, wherein: the initiator is a peroxide initiator.
10. A solar cell, characterized by: comprising the poly 3, 4-ethylenedioxythiophene conductive material of claim 7.
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| CN112768611A (en) * | 2021-01-11 | 2021-05-07 | 陈云 | Preparation method of trans-organic-inorganic hybrid perovskite solar cell |
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