CN114524965A - Method for preparing porous material and chemicals from anhydride cured epoxy resin - Google Patents
Method for preparing porous material and chemicals from anhydride cured epoxy resin Download PDFInfo
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- CN114524965A CN114524965A CN202210154022.8A CN202210154022A CN114524965A CN 114524965 A CN114524965 A CN 114524965A CN 202210154022 A CN202210154022 A CN 202210154022A CN 114524965 A CN114524965 A CN 114524965A
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- epoxy resin
- anhydride
- chemicals
- porous materials
- cured epoxy
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 63
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 63
- 239000000126 substance Substances 0.000 title claims abstract description 50
- 150000008064 anhydrides Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000011148 porous material Substances 0.000 title claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 58
- 238000006731 degradation reaction Methods 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- -1 aromatic glyceryl ether compounds Chemical class 0.000 claims abstract description 22
- 230000015556 catabolic process Effects 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 19
- 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
- 238000002156 mixing Methods 0.000 claims description 11
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 238000001035 drying Methods 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
- 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
- 239000007787 solid Substances 0.000 claims description 5
- 238000005406 washing 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
- 150000004714 phosphonium salts Chemical group 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
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- 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
- QFHMNFAUXJAINK-UHFFFAOYSA-N [1-(carbamoylamino)-2-methylpropyl]urea Chemical compound NC(=O)NC(C(C)C)NC(N)=O QFHMNFAUXJAINK-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
- MFIUDWFSVDFDDY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 MFIUDWFSVDFDDY-UHFFFAOYSA-M 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
- NJXBVBPTDHBAID-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 NJXBVBPTDHBAID-UHFFFAOYSA-M 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
- 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
- 229960001124 trientine Drugs 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 30
- 239000011347 resin Substances 0.000 abstract description 30
- 239000003054 catalyst Substances 0.000 abstract description 16
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004917 carbon fiber Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004593 Epoxy 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 238000010586 diagram Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000011521 glass Substances 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
- 230000000717 retained effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method 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
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- 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 porous materials and chemicals by using anhydride cured epoxy resin, belonging to the technical field of thermosetting resin degradation and recovery. The invention mainly solves the problems that the solvent is easy to volatilize and difficult to recover, the resin needs to be pretreated and the like in the processes of depolymerizing the anhydride curing epoxy resin and preparing the functional material thereof at present. According to the invention, a binary or ternary solvent system and anhydride curing epoxy resin are mixed, and the reaction progress degree is controlled by adjusting the solvent composition, temperature and time, so that epoxy resin porous materials or aromatic glyceryl ether compounds with different morphologies are obtained. The invention has the advantages of simple 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 thermosetting resin degradation and recovery, and particularly relates to a method for preparing a porous material and chemicals by using 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 anhydride curing agents and curing and crosslinking through ester bonds, and is widely applied to the fields of wind power energy, aerospace, transportation, sports equipment, bridge construction and the like. The anhydride curing epoxy resin is difficult to degrade in nature, so a large amount of leftover materials and wastes generated in industrial production and life cannot be well treated, and the problems of serious environmental pollution and resource waste are caused. At present, the chemical recovery method of the anhydride curing epoxy resin mainly comprises hydrolysis, alcoholysis, aminolysis, acidolysis and the like. Acid or alkaline catalysts are often needed to be added to catalyze the degradation of the resin in the hydrolysis process of the anhydride curing epoxy resin, and the ester bonds of the alkaline catalysts in the resin are hydrolyzed and consumed, so that the alkaline catalysts cannot be recycled; the acidic catalyst such as metal salts and organic acids has large catalyst dosage and the product is easy to generate a carbonization process. In the alcoholysis, aminolysis and acidolysis method, substances such as micromolecular alcohols, amines and acetic acid are used as solvents, the solvents are volatile to cause solvent loss, and part of the solvents are corrosive and irritant and cause harm to the environment; and additional catalyst addition is required for resin degradation. Patent CN 110157038 discloses a method for low-temperature rapid degradation and separation of ester bond-containing polymer resin, which is to use alcohols and ketones as solvents after pretreatment of ester bond-containing resin, and alkali alkoxide, metal salt, metal oxide or hydroxide as catalysts to break ester bonds in resin, but the resin needs pretreatment, an alkali catalyst needs to be added in the reaction, and the catalyst is easy to consume and cannot be recycled. Patent CN 109897216 discloses a method for recycling waste thermosetting resin and composite material thereof, which comprises the steps of placing thermosetting resin in polyhalogenated hydrocarbon or organic amine for pretreatment, and then degrading the treated resin in polyamine or mixture of polyamine and organic solvent to prepare oleogel. Patent CN 111393703 discloses a method for preparing functional materials from thermosetting resin and application thereof, wherein the resin is crushed and then placed in protonic acid such as sulfuric acid, hydrochloric acid, nitric acid, etc. or lewis acid and hydrogen peroxide for mixing and processing, which is harmful to environment. In conclusion, the existing methods for degrading anhydride cured epoxy resin have the problems that the resin needs to be pretreated, the reaction solvent is volatile, a catalyst needs to be additionally added and the like.
Disclosure of Invention
Aiming at the problems that the solvent is easy to volatilize and difficult to recover and the resin needs to be pretreated in the depolymerization of the prior anhydride-cured epoxy resin and the preparation process of the functional material thereof, the invention provides the method for preparing the porous material and the chemical by the anhydride-cured epoxy resin, which has the advantages of simple and convenient preparation of the solvent, low cost, low toxicity, good solubility, simple and convenient degradation method and no need of adding extra catalyst.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing porous materials and chemicals from anhydride-cured epoxy resins, comprising the steps of: mixing a binary or ternary solvent system and anhydride curing epoxy resin, and controlling the degree of degradation reaction by adjusting the composition, temperature and time of the solvent to obtain epoxy resin porous materials or aromatic glyceryl ether compounds with different shapes. The solvent system has the advantages of water solubility, low volatility, non-flammability, degradability, recyclability, 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 can be used as a solvent to promote the swelling of the resin; in the process, other substances do not need to be additionally added as catalysts, so that the degradation system is simple; ester bonds in the resin are selectively cleaved and ether bonds are retained.
Further, the binary or ternary solvent system is formed by combining a hydrogen bond acceptor and a hydrogen bond donor. Compared with the traditional solvent, the degradation process of the anhydride curing epoxy resin has the advantages of stable property and good swelling promoting effect, and a catalyst does not need to be added in the system.
Further, the hydrogen bond acceptor comprises one or a mixture of several 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 substances in any ratio of water, urea and derivatives thereof, polyalcohol substances, carboxylic acid substances, sulfonic acid substances and polyamine substances.
Further, the quaternary ammonium salt substance comprises one or a mixture of several of choline chloride, tetramethylammonium chloride, tetraethylammonium chloride, tetramethylammonium bromide, tetraethylammonium bromide and tetrabutylammonium bromide in any ratio; the quaternary phosphonium salt substance comprises one or a mixture of a plurality of tetrabutylphosphonium bromide, methyltriphenylphosphonium bromide, ethyltriphenylphosphonium chloride and butyltriphenylphosphonium chloride in any ratio; the zwitterion is betaine and the like; the urea and the derivatives thereof comprise one or a mixture of a plurality of urea, biuret, hydroxymethyl urea and isobutyl idene diurea in any ratio; the polyalcohol substances comprise one or a mixture of more of ethylene glycol, glycerol, propylene glycol, butanediol, hexanediol, diethylene glycol and dipropylene glycol in any ratio; the carboxylic acid substances comprise 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 a plurality of methanesulfonic acid, p-toluenesulfonic acid, dodecylbenzene sulfonic acid and trifluoromethanesulfonic acid in any ratio; the polyamine substance comprises one or a mixture of several of ethylenediamine, diethylenetriamine and triethylene tetramine in any ratio. The hydrogen bond donor provides an active group which reacts with an ester bond in the resin, so that the ester bond in the resin can realize selective bond breaking; the solvent formed by the hydrogen bond donor and the hydrogen bond acceptor has stable property and good solubility in water, is easy to separate and recycle products, and can be recycled.
Further, the anhydride-cured epoxy resin comprises a pure anhydride-cured epoxy resin, a carbon fiber-reinforced anhydride-cured epoxy resin and a 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 a 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 curing epoxy resin is completely degraded, the obtained product is an aromatic glyceryl ether compound; when the anhydride cured epoxy resin is partially degraded, the obtained product is an epoxy resin porous material. The degradation degree of the anhydride-cured epoxy resin is different, and the obtained depolymerized products are different.
Further, when the anhydride curing epoxy resin is completely degraded, adding water into the degradation system after reaction until a substance is separated out, and separating out components to obtain the aromatic glycerol ether compound with high additional value; and when the anhydride curing epoxy resin is partially degraded, directly separating solid components in the system, washing with water and drying to obtain the epoxy resin porous material. The degradation product aromatic glycerol ether compound has higher solubility in the binary or ternary solvent system, and the aromatic glycerol ether compound can be separated out by adding water into the system and adjusting the polarity of the degradation system; and the porous material cannot be dissolved in a degradation system.
Further, the heating mode of the reaction is one of traditional heating or microwave heating. The degradation reaction can be carried out by using a traditional heating mode and a microwave reactor, so that the reaction is carried out more efficiently.
Further, the temperature of the degradation reaction is 40-230 ℃; the time of degradation reaction is 30 s-12 h. When the reaction temperature is lower than the range, the resin cannot be degraded; when the reaction temperature is high, the cleavage of the C-C bond and the C-O ether bond in the resin easily occurs, thereby generating a large amount of by-products and even causing carbonization.
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 continuously using the solvent for the next degradation reaction; (2) when the product is an epoxy resin porous material, the degradation liquid is directly recycled. The solvent system can be recycled for many 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 completely recycled;
(2) the degradation system does not need to additionally add a catalyst, is simple and has low 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 a porous material obtained before reaction and after degradation reaction of an acid anhydride-cured epoxy resin (wherein a is before reaction of the acid anhydride-cured epoxy resin and b is after degradation reaction);
FIG. 2 is a schematic view of the structural formula of an anhydride-cured epoxy resin;
fig. 3 is a schematic view of recycled carbon fibers.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below with reference to the accompanying drawings, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Heating and stirring oxalic acid and choline chloride with the mass ratio of 4:1 to form a binary solvent system, mixing 1g of anhydride-cured epoxy resin (shown in figure 2) and 4g of oxalic acid-choline chloride solvent to react at 180 ℃ for 12 hours, separating the solid in the system after the reaction, washing with water and drying to obtain the porous material (shown in figure 1), wherein the oxalic acid-choline chloride solvent in the system can be used for the next reaction.
Example 2
Heating and stirring urea and choline chloride with the molar ratio of 2:1 to form a binary solvent system, mixing 1g of carbon fiber reinforced anhydride cured epoxy resin and 2g of urea-choline chloride solvent at 230 ℃ for reaction for 10 hours, taking out carbon fiber in the system after the reaction (as shown in figure 3), adding water into the system until substances are separated out, separating out components to obtain an aromatic glycerol ether compound with high added value, drying the water in the solvent, and continuously using the aromatic glycerol ether compound in the next degradation reaction.
Example 3
Heating and stirring trifluoromethanesulfonic acid and tetrabutyl phosphonium bromide with a molar ratio of 1:1 to form a binary solvent system, mixing 1g of glass fiber reinforced anhydride-cured epoxy resin and 10g of trifluoromethanesulfonic acid-tetrabutyl phosphonium bromide solvent, heating the mixture at 40 ℃ for 30s with microwaves, taking out glass fibers in the system after reaction, adding water into the system until substances are separated out, separating out components to obtain an aromatic glycerol ether compound with a high additional value, drying water in the solvent, and continuously using the aromatic glycerol ether compound in the next degradation reaction.
Example 4
Heating and stirring lactic acid and betaine with a molar ratio of 2:1 to form a binary solvent system, mixing 1g of anhydride-cured epoxy resin and 6g of lactic acid-betaine solvent, heating for 2 hours at 100 ℃, separating solids in the system after reaction, washing with water and drying to obtain a porous material, wherein the lactic acid-betaine solvent in the system can be used for the next reaction.
Example 5
Heating and stirring ethylene glycol and tetramethylammonium chloride with the molar ratio of 2:1 to form a binary solvent system, mixing 1g of glass fiber reinforced anhydride cured epoxy resin and 5g of ethylene glycol-tetramethylammonium chloride solvent, heating for 20min at 80 ℃, separating the solid in the system after reaction, washing with water and drying to obtain the porous material, wherein the ethylene glycol-tetramethylammonium chloride solvent in the system can be used for the next reaction.
Example 6
Heating and stirring water, ethylenediamine and tetraethylammonium chloride with the molar ratio of 0.5:2:1 to form a ternary solvent system, mixing 1g of anhydride-cured epoxy resin and 3g of water-ethylenediamine-tetraethylammonium chloride solvent, adding the mixture for 1 hour at 160 ℃, adding water into the system after reaction until substances are separated out, separating out components to obtain an aromatic glycerol ether compound with high added value, drying the water in the solvent, and continuously using the aromatic glycerol ether compound in the next degradation reaction.
Example 7
Heating and stirring ethylene glycol and tetramethylammonium chloride with a molar ratio of 2:1 to form a binary solvent system, mixing 1g of glass fiber reinforced anhydride cured epoxy resin and 5g of ethylene glycol-tetramethylammonium chloride solvent, heating at 130 ℃ for 20 hours to carbonize the resin, and thus, an aromatic glycerol ether compound or a porous material cannot be obtained.
Example 8
Heating and stirring urea and choline chloride with the molar ratio of 2:1 to form a binary solvent system, mixing 1g of carbon fiber reinforced anhydride cured epoxy resin and 3g of urea-choline chloride solvent at 30 ℃ for reaction for 10 hours, wherein the resin cannot be degraded.
Those skilled in the art will appreciate that the invention may be practiced without these specific details. Although illustrative embodiments of the present invention have been described above to facilitate the 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, and various changes may be made apparent to those skilled in the art as long as they are within the spirit and scope of the present invention as defined and defined by the appended claims, and all matters of the invention which utilize the inventive concepts are protected.
Claims (10)
1. A method for preparing porous materials and chemicals by curing epoxy resin with anhydride 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 degree of degradation reaction by adjusting the composition, temperature and time of the solvent to obtain epoxy resin porous materials or aromatic glyceryl ether compounds with different shapes.
2. The method of claim 1 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: the binary or ternary solvent system is formed by combining a hydrogen bond acceptor and a hydrogen bond donor.
3. The method of preparing porous materials and chemicals from anhydride cured epoxy resin as claimed in claim 2, wherein: the hydrogen bond acceptor comprises one or a mixture of more 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 substances in any ratio of water, urea and derivatives thereof, polyalcohol substances, carboxylic acid substances, sulfonic acid substances and polyamine substances.
4. The method of claim 3 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: the quaternary ammonium salt substance comprises one or a mixture of more of choline chloride, tetramethylammonium chloride, tetraethylammonium chloride, tetramethylammonium bromide, tetraethylammonium bromide and tetrabutylammonium bromide in any ratio; the quaternary phosphonium salt substance comprises one or a mixture of a plurality of tetrabutylphosphonium bromide, methyltriphenylphosphonium bromide, ethyltriphenylphosphonium chloride and butyltriphenylphosphonium chloride in any ratio; the zwitterion is betaine; the urea and the derivatives thereof comprise one or a mixture of a plurality of urea, biuret, hydroxymethyl urea and isobutyl idene diurea in any ratio; the polyalcohol substances comprise one or a mixture of more of ethylene glycol, glycerol, propylene glycol, butanediol, hexanediol, diethylene glycol and dipropylene glycol in any ratio; the carboxylic acid substances comprise 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 a plurality of methanesulfonic acid, p-toluenesulfonic acid, dodecylbenzene sulfonic acid and trifluoromethanesulfonic acid in any ratio; the polyamine substance comprises one or a mixture of several of ethylenediamine, diethylenetriamine and triethylene tetramine in any ratio.
5. The method of claim 4 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: the heating mode of the reaction is one of traditional heating or microwave heating.
6. The method of claim 5 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: the mass ratio of the binary or ternary solvent system to the anhydride curing epoxy resin is 2-10: 1.
7. The method of claim 6 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: when the anhydride curing epoxy resin is completely degraded, the obtained product is an aromatic glyceryl ether compound; when the anhydride cured epoxy resin is partially degraded, the obtained product is an epoxy resin porous material.
8. The method of claim 7 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: when the anhydride curing epoxy resin is completely degraded, adding water into a degradation system after reaction until a substance is separated out, and separating out components to obtain an aromatic glycerol ether compound with a high additional value; when the anhydride curing epoxy resin is partially degraded, directly separating solid components in the system, washing with water and drying to obtain the epoxy resin porous material.
9. The method of claim 8 for preparing porous materials and chemicals from anhydride cured epoxy resins, wherein: the temperature of the degradation reaction is 40-230 ℃; the time of degradation reaction is 30 s-12 h.
10. The method for preparing porous materials and chemicals from anhydride-cured epoxy resins according to any of claims 1 to 9, wherein: 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 continuously using the solvent for the next degradation reaction; (2) when the product is an epoxy resin porous material, the degradation liquid is directly recycled.
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