CN114524965B - Method for preparing epoxy porous material or aromatic glyceryl ether compound by using anhydride cured epoxy resin - Google Patents
Method for preparing epoxy porous material or aromatic glyceryl ether compound by using anhydride cured epoxy resin Download PDFInfo
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- CN114524965B CN114524965B CN202210154022.8A CN202210154022A CN114524965B CN 114524965 B CN114524965 B CN 114524965B CN 202210154022 A CN202210154022 A CN 202210154022A CN 114524965 B CN114524965 B CN 114524965B
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- epoxy resin
- aromatic
- anhydride
- porous material
- ether compound
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 58
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 58
- 150000008064 anhydrides Chemical class 0.000 title claims abstract description 40
- -1 aromatic glyceryl ether compound Chemical class 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000011148 porous material Substances 0.000 title claims abstract description 26
- 239000004593 Epoxy Substances 0.000 title claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 56
- 238000006731 degradation reaction Methods 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 230000015556 catabolic process Effects 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 7
- 229960003178 choline chloride Drugs 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 6
- 235000019743 Choline chloride Nutrition 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 5
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 2
- RTFFRZWAOUGYSN-UHFFFAOYSA-N CCCCC(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Cl Chemical compound CCCCC(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Cl RTFFRZWAOUGYSN-UHFFFAOYSA-N 0.000 claims description 2
- DASNDJBQHOUCAV-UHFFFAOYSA-N CCCCP(CCCC)(CCCC)CCCC.Br Chemical compound CCCCP(CCCC)(CCCC)CCCC.Br DASNDJBQHOUCAV-UHFFFAOYSA-N 0.000 claims description 2
- GBYIPEFQQCCCJP-UHFFFAOYSA-N Cl.C(C)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound Cl.C(C)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 GBYIPEFQQCCCJP-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000004714 phosphonium salts Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 30
- 239000011347 resin Substances 0.000 abstract description 30
- 239000003054 catalyst Substances 0.000 abstract description 15
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000011084 recovery Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- 229920000049 Carbon (fiber) Polymers 0.000 description 5
- 239000004917 carbon fiber Substances 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 230000000593 degrading effect Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- KJAVMJDVWBHWFG-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium oxalic acid chloride Chemical compound [Cl-].OC(=O)C(O)=O.C[N+](C)(C)CCO KJAVMJDVWBHWFG-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/26—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing carboxylic acid groups, their anhydrides or esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/28—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic compounds containing nitrogen, sulfur or phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- 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
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
The invention discloses a method for preparing an epoxy porous material or an aromatic glyceride compound by using anhydride cured epoxy resin, belonging to the technical field of degradation and recovery of thermosetting resin. The invention mainly solves the problems of easy volatilization of solvent, difficult recovery, pretreatment of resin and the like in the preparation process of the functional material of the existing anhydride curing epoxy resin. The invention mixes binary or ternary solvent system and anhydride curing epoxy resin, and obtains epoxy resin porous materials or aromatic glyceryl ether compounds with different morphologies by adjusting the solvent composition, temperature and time and controlling the reaction progress. The invention has the advantages of simple and convenient solvent preparation, low cost, low toxicity, good solubility, high degradation activity and no need of adding extra catalyst.
Description
Technical Field
The invention belongs to the technical field of degradation and recovery of thermosetting resin, and particularly relates to a method for preparing an epoxy porous material or an aromatic glyceride compound from anhydride cured epoxy resin.
Background
The anhydride cured epoxy resin is a thermosetting resin with a special three-dimensional network structure, which is formed by reacting resin containing epoxy active groups with an anhydride curing agent and curing and crosslinking through ester bonds, and is widely applied to the fields of wind-electricity energy sources, aerospace, transportation, sports equipment, bridge construction and the like. Anhydride cured epoxy resin is difficult to degrade in nature, so that a large amount of leftover materials and wastes generated in industrial production and life cannot be well treated, and serious environmental pollution and resource waste are caused. At present, the chemical recovery method of the anhydride curing epoxy resin mainly comprises the methods of hydrolysis, alcoholysis, aminolysis, acidolysis and the like. The hydrolysis process of the anhydride curing epoxy resin often needs to add an acidic or alkaline catalyst to catalyze the resin to degrade, and the alkaline catalyst is consumed by ester bond hydrolysis in the resin and cannot be recycled; and acid catalysts such as metal salts and organic acids have large catalyst consumption and the products are easy to be carbonized. The alcoholysis, aminolysis and acidolysis methods use substances such as micromolecular alcohols, amines, acetic acid and the like as solvents, the solvents are easy to volatilize, the solvents are lost, and part of the solvents are corrosive and irritant, so that the environment is harmed; and the resin degradation also requires the addition of an additional catalyst. Patent CN 110157038 discloses a method for rapidly degrading and separating ester bond-containing polymer resin at low temperature, which uses alcohols and ketones as solvents after pretreatment of the ester bond-containing resin, and uses alkaline alkoxide, metal salt, metal oxide or hydroxide as catalysts to break ester bonds in the resin, but the resin needs pretreatment, alkaline catalysts need to be added in the reaction, and the catalysts are easy to consume and cannot be recovered. Patent CN 109897216 discloses a method for recycling waste thermosetting resin and its composite material, which comprises pre-treating thermosetting resin in polyhalogenated hydrocarbon or organic amine, and degrading the treated resin in polyamine or mixture of polyamine and organic solvent to obtain oleogel. Patent CN 111393703 discloses a method for preparing functional material by using thermosetting resin and its application, after the resin is crushed, it is placed in protonic acid of sulfuric acid, hydrochloric acid and nitric acid or lewis acid and hydrogen peroxide, and mixed and treated, so that its environmental hazard is large. In summary, the existing method for degrading the anhydride-cured epoxy resin has the problems that the resin needs to be pretreated, the reaction solvent is easy to volatilize, and the catalyst needs to be additionally added.
Disclosure of Invention
Aiming at the problems that the solvent is easy to volatilize and difficult to recycle and the resin needs to be pretreated in the preparation process of the existing anhydride curing epoxy resin depolymerization and functional materials thereof, the invention provides the method for preparing the epoxy porous material or the aromatic glycerol ether compound from the anhydride curing epoxy resin, which has the advantages of simple and convenient solvent preparation, low cost, low toxicity, good solubility, simple degradation method and no need of additional catalyst.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a method for preparing an epoxy porous material or an aromatic glycerol ether compound from anhydride cured epoxy resin comprises the following steps: mixing the binary or ternary solvent system and the anhydride curing epoxy resin, and controlling the degradation reaction progress degree by adjusting the solvent composition, the temperature and the time to obtain the epoxy resin porous material or the aromatic glycerol ether compound with different morphologies. The solvent system has the advantages of water compatibility, low volatility, incombustibility, degradability, recycling, low raw material cost, easy preparation and the like. The solvent system can be used as a reactant and a catalyst in the degradation of the anhydride curing epoxy resin, and simultaneously can be used as a solvent to promote the swelling of the resin; in the process, other substances are not required to be additionally added as catalysts, and the degradation system is simple; the ester bonds in the resin are selectively broken and the ether bonds remain.
Further, the binary or ternary solvent system is composed of a combination of hydrogen bond acceptors and hydrogen bond donors. Compared with the traditional solvent, the catalyst has the advantages of stable property and good swelling promoting effect in the degradation process of the anhydride curing epoxy resin, and no catalyst is needed to be added in the system.
Further, the hydrogen bond acceptor comprises one or a mixture of a plurality of any ratios of quaternary ammonium salt substances, quaternary phosphonium salt substances and zwitterions; the hydrogen bond donor comprises one or a mixture of a plurality of water, urea and derivatives thereof, polyalcohol substances, carboxylic acid substances, sulfonic acid substances and polyamine substances in any ratio.
Further, the quaternary ammonium salt substance comprises one or a mixture of a plurality of choline chloride, tetramethyl ammonium chloride, tetraethyl ammonium chloride, tetramethyl ammonium bromide, tetraethyl ammonium bromide and tetrabutyl ammonium bromide in any ratio; the quaternary phosphine salt substance comprises one or a mixture of a plurality of tetrabutyl phosphine bromide, methyltriphenyl phosphine bromide, ethyltriphenyl phosphine chloride and butyltriphenyl phosphine chloride in any ratio; the zwitterion is betaine and the like; the urea and the derivative thereof comprise one or a mixture of a plurality of urea, biuret, hydroxymethyl urea and isobutylidene biurea in any ratio; the polyalcohol substance comprises one or a mixture of more than one of ethylene glycol, glycerol, propylene glycol, butanediol, hexanediol, diethylene glycol and dipropylene glycol in any ratio; the carboxylic acid substance comprises one or a mixture of a plurality of oxalic acid, lactic acid, malic acid and trichloroacetic acid in any ratio; the sulfonic acid substance comprises one or a mixture of several of methane sulfonic acid, p-toluene sulfonic acid, dodecylbenzene sulfonic acid and trifluoro methane sulfonic acid in any ratio; the polyamine substance comprises one or a mixture of several of ethylenediamine, diethylenetriamine and triethylenetetramine in any ratio. The hydrogen bond donor provides active groups which react with ester bonds in the resin, so that the ester bonds in the resin can realize selective bond breaking; the solvent formed by the hydrogen bond donor and the hydrogen bond acceptor has stable property, good solubility in water, easy separation and recovery of products and recycling of a solvent system.
Further, the anhydride-cured epoxy resin comprises pure anhydride-cured epoxy resin, carbon fiber reinforced anhydride-cured epoxy resin and glass fiber reinforced anhydride-cured epoxy resin.
Further, the mass ratio of the binary or ternary solvent system to the anhydride curing epoxy resin is 2-10:1. When the proportion of the binary or ternary solvent system is low, the resin is difficult to be immersed by the solvent, and ester bonds in the resin cannot be degraded; when the proportion of the binary or ternary solvent system is high, the reaction economy is poor.
Further, when the anhydride cured epoxy resin is completely degraded, the obtained product is an aromatic glycerol ether compound; when the anhydride cured epoxy resin is partially degraded, the obtained product is an epoxy resin porous material. The degree of degradation of the anhydride-cured epoxy resin varies, and the depolymerization products obtained vary.
Further, when the anhydride curing epoxy resin is completely degraded, adding water into the degradation system after the reaction until substances are separated out, and separating out components to obtain the aromatic glycerol ether compound with high added value; when the anhydride curing epoxy resin is partially degraded, solid components in the system are directly separated, and the epoxy resin porous material is obtained by washing and drying. The degradation product aromatic glyceryl ether compound has higher solubility in the binary or ternary solvent system, and the aromatic glyceryl ether compound can be separated out by adding water into the system and adjusting the polarity of the degradation system; whereas porous materials are insoluble in the degradation system.
Further, the heating mode of the reaction is one of conventional heating or microwave heating. The degradation reaction can be heated by using a traditional heating mode and a microwave reactor, so that the reaction is more efficiently carried out.
Further, the temperature of the degradation reaction is 40-230 ℃; the degradation reaction time is 30 s-12 h. When the reaction temperature is below this range, the resin cannot be degraded; when the reaction temperature is high, cleavage of the C-C bond and the C-O ether bond in the resin easily occurs, thereby producing a large amount of by-products and even charring.
Further, the recycling method of the binary or ternary solvent system comprises (1) when the product is an aromatic glycerol ether compound, removing water from the separated solvent, and continuing to be used for the next degradation reaction; (2) When the product is epoxy resin porous material, the degradation liquid is directly recycled. The solvent system can be recycled for a plurality of times.
Compared with the prior art, the invention has the following advantages:
(1) The binary or ternary solvent system is not easy to volatilize and can be fully recovered;
(2) The degradation system does not need to additionally add a catalyst, and is simple and low in cost;
(3) The product is easy to separate, and the added value of the product is high;
(4) The resin does not need to be pretreated, and the operation is simple and convenient;
(5) The method is also applicable to unsaturated polyester resin and vinyl resin.
Drawings
FIG. 1 is a schematic diagram showing a comparison of porous materials obtained before an anhydride curing epoxy resin reaction and after a degradation reaction (wherein FIG. a is before an anhydride curing epoxy resin reaction and wherein b is after a degradation reaction);
FIG. 2 is a schematic diagram of the structural formula of an anhydride cured epoxy resin;
fig. 3 is a schematic view of recycled carbon fiber.
Detailed Description
The following description of the embodiments of the present invention will be made more apparent and fully hereinafter with reference to the accompanying drawings, in which some, but not all embodiments of the invention are shown. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
Oxalic acid and choline chloride with the mass ratio of 4:1 are heated and stirred to form a binary solvent system, 1 g anhydride curing epoxy resin (shown in figure 2) and 4 g oxalic acid-choline chloride solvent are mixed and reacted at 180 ℃ for 12 h, solids in the system are separated after the reaction, the solid is washed and dried, and a porous material (shown in figure 1) is obtained, wherein the oxalic acid-choline chloride solvent in the system can be used for the next reaction.
Example 2
Urea and choline chloride with the molar ratio of 2:1 are heated and stirred to form a binary solvent system, 1 g carbon fiber reinforced anhydride curing epoxy resin and 2 g urea-choline chloride solvent are mixed and react at 230 ℃ for 10 h, carbon fibers (shown in figure 3) in the system are taken out after the reaction, water is added into the system until substances are separated out, the separated-out components are separated out, a high-added-value aromatic glyceryl ether compound is obtained, and the solvent is dried for moisture and can be continuously used in the next degradation reaction.
Example 3
1:1, mixing 1 g glass fiber reinforced anhydride cured epoxy resin and 10 g trifluoro methanesulfonic acid-tetrabutyl phosphine bromide solvent, heating by microwave at 40 ℃ for 30 s, taking out glass fiber in the system after reaction, adding water into the system until substances are separated out, separating out components to obtain high added value aromatic glyceryl ether compound, drying the solvent moisture, and continuously using in the next degradation reaction.
Example 4
Lactic acid and betaine with the molar ratio of 2:1 are heated and stirred to form a binary solvent system, 1 g anhydride curing epoxy resin and 6 g lactic acid-betaine solvent are mixed, the mixture is heated by microwaves at the temperature of 100 ℃ for 2 h, solids in the system are separated after the reaction, the solids are washed and dried, and a porous material is obtained, wherein the lactic acid-betaine solvent in the system can be used for the next reaction.
Example 5
Ethylene glycol and tetramethyl ammonium chloride with the molar ratio of 2:1 are heated and stirred to form a binary solvent system, 1 g glass fiber reinforced anhydride curing epoxy resin and 5 g ethylene glycol-tetramethyl ammonium chloride solvent are mixed, microwave heating is carried out for 20 min at 80 ℃, solids in the system are separated after reaction, washing and drying are carried out, and the porous material is obtained, wherein the ethylene glycol-tetramethyl ammonium chloride solvent in the system can be used for the next reaction.
Example 6
The molar ratio of water, ethylenediamine and tetraethyl ammonium chloride is 0.5:1, heating and stirring are carried out to form a ternary solvent system, 1 g anhydride curing epoxy resin and 3g water-ethylenediamine-tetraethyl ammonium chloride solvent are mixed, 1 h is added into the system by microwaves at 160 ℃, water is added into the system after the reaction until substances are separated out, the separated-out components are separated out, a high-added-value aromatic glyceryl ether compound is obtained, and the solvent is dried by moisture and can be continuously used in the next degradation reaction.
Example 7
Ethylene glycol and tetramethyl ammonium chloride with the molar ratio of 2:1 are heated and stirred to form a binary solvent system, 1 g glass fiber reinforced anhydride cured epoxy resin and 5 g ethylene glycol-tetramethyl ammonium chloride solvent are mixed, and heated at 130 ℃ for 20 h, and the resin is carbonized, so that an aromatic glycerol ether compound or a porous material can not be obtained.
Example 8
Urea and choline chloride with the molar ratio of 2:1 are heated and stirred to form a binary solvent system, 1 g carbon fiber reinforced anhydride curing epoxy resin and 3g urea-choline chloride solvent are mixed and reacted at 30 ℃ for 10 h, and the resin cannot be degraded.
What is not described in detail in the present specification belongs to the prior art known to those skilled in the art. While the foregoing describes illustrative embodiments of the present invention to facilitate an understanding of the present invention by those skilled in the art, it should be understood that the present invention is not limited to the scope of the embodiments, but is to be construed as protected by the accompanying claims insofar as various changes are within the spirit and scope of the present invention as defined and defined by the appended claims.
Claims (5)
1. A method for preparing epoxy porous material or aromatic glycerol ether compound by using anhydride cured epoxy resin is characterized in that: the method comprises the following steps: mixing a binary or ternary solvent system and anhydride curing epoxy resin, and controlling the degradation reaction progress degree by adjusting the solvent composition, the temperature and the time to obtain epoxy resin porous materials or aromatic glyceryl ether compounds with different morphologies; the binary or ternary solvent system is formed by combining a hydrogen bond acceptor and a hydrogen bond donor; the hydrogen bond acceptor comprises one or a mixture of a plurality of quaternary ammonium salt substances, quaternary phosphonium salt substances and zwitterions in any ratio; the hydrogen bond donor comprises one or a mixture of a plurality of water, urea and derivatives thereof, polyalcohol substances, carboxylic acid substances, sulfonic acid substances and polyamine substances in any ratio;
the mass ratio of the binary or ternary solvent system to the anhydride curing epoxy resin is 2-10:1;
when the anhydride curing epoxy resin is completely degraded, the obtained product is an aromatic glycerol ether compound; when the anhydride curing epoxy resin is partially degraded, the obtained product is an epoxy resin porous material;
the temperature of the degradation reaction is 40-230 ℃; the degradation reaction time is 30 s-12 h.
2. The method for preparing an epoxy porous material or an aromatic glycerin ether compound from an anhydride-cured epoxy resin according to claim 1, wherein: the quaternary ammonium salt substance comprises one or a mixture of a plurality of choline chloride, tetramethyl ammonium chloride, tetraethyl ammonium chloride, tetramethyl ammonium bromide, tetraethyl ammonium bromide and tetrabutyl ammonium bromide in any ratio; the quaternary phosphine salt substance comprises one or a mixture of a plurality of tetrabutyl phosphine bromide, methyltriphenyl phosphine bromide, ethyltriphenyl phosphine chloride and butyltriphenyl phosphine chloride in any ratio; the zwitterionic is betaine; the urea and the derivative thereof comprise one or a mixture of a plurality of urea, biuret, hydroxymethyl urea and isobutylidene biurea in any ratio; the polyalcohol substance comprises one or a mixture of more than one of ethylene glycol, glycerol, propylene glycol, butanediol, hexanediol, diethylene glycol and dipropylene glycol in any ratio; the carboxylic acid substance comprises one or a mixture of a plurality of oxalic acid, lactic acid, malic acid and trichloroacetic acid in any ratio; the sulfonic acid substance comprises one or a mixture of several of methane sulfonic acid, p-toluene sulfonic acid, dodecylbenzene sulfonic acid and trifluoro methane sulfonic acid in any ratio; the polyamine substance comprises one or a mixture of several of ethylenediamine, diethylenetriamine and triethylenetetramine in any ratio.
3. The method for preparing an epoxy porous material or an aromatic glycerin ether compound from an anhydride-cured epoxy resin according to claim 2, wherein: the heating mode of the reaction is one of traditional heating or microwave heating.
4. A method for preparing an epoxy porous material or an aromatic glycerin ether compound from an anhydride-cured epoxy resin according to claim 3, wherein: when the anhydride curing epoxy resin is completely degraded, adding water into the degradation system after the reaction until substances are separated out, and separating out components to obtain the aromatic glycerol ether compound with high added value; when the anhydride curing epoxy resin is partially degraded, solid components in the system are directly separated, and the epoxy resin porous material is obtained by washing and drying.
5. The method for preparing an epoxy porous material or an aromatic glycerol ether compound from an anhydride-cured epoxy resin according to any one of claims 1 to 4, wherein the method comprises the following steps: the recycling method of the binary or ternary solvent system comprises (1) when the product is an aromatic glycerol ether compound, removing water from the separated solvent, and continuing to be used for the next degradation reaction; (2) When the product is epoxy resin porous material, the degradation liquid is directly recycled.
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