CN115418020B - Recycling method of polyimide foam waste - Google Patents
Recycling method of polyimide foam waste Download PDFInfo
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- CN115418020B CN115418020B CN202211225708.8A CN202211225708A CN115418020B CN 115418020 B CN115418020 B CN 115418020B CN 202211225708 A CN202211225708 A CN 202211225708A CN 115418020 B CN115418020 B CN 115418020B
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- China
- Prior art keywords
- polyimide foam
- foam waste
- dianhydride
- polyimide
- recycling
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- 239000004642 Polyimide Substances 0.000 title claims abstract description 107
- 229920001721 polyimide Polymers 0.000 title claims abstract description 107
- 239000006260 foam Substances 0.000 title claims abstract description 85
- 239000002699 waste material Substances 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004064 recycling Methods 0.000 title claims abstract description 27
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002243 precursor Substances 0.000 claims abstract description 21
- 239000006261 foam material Substances 0.000 claims abstract description 16
- 239000000853 adhesive Substances 0.000 claims abstract description 13
- 230000001070 adhesive effect Effects 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 7
- 239000004088 foaming agent Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 claims description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 238000010298 pulverizing process Methods 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- -1 4-phenoxyphenyl Chemical group 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- MBVGJZDLUQNERS-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazole-4,5-dicarbonitrile Chemical compound FC(F)(F)C1=NC(C#N)=C(C#N)N1 MBVGJZDLUQNERS-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920002545 silicone oil Polymers 0.000 claims description 3
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 claims description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012972 dimethylethanolamine Substances 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- 238000005187 foaming Methods 0.000 abstract description 6
- 238000001723 curing Methods 0.000 description 15
- 238000011084 recovery Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000011415 microwave curing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/125—Water, e.g. hydrated salts
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
-
- 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
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/142—Compounds containing oxygen but no halogen atom
-
- 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
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/10—Water or water-releasing compounds
-
- 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
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/12—Organic compounds only containing carbon, hydrogen and oxygen atoms, e.g. ketone or alcohol
-
- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- 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
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
Abstract
The invention belongs to the technical field of polyimide foam waste recycling, and particularly relates to a polyimide foam waste recycling method, which comprises the following steps: crushing polyimide foam waste, fully mixing the crushed polyimide foam with dianhydride, a foaming agent, a solvent, an auxiliary agent and an adhesive, adding isocyanate, stirring to obtain a polyimide foam precursor, pouring the polyimide foam precursor into a mould, foaming and self-curing, and heating and curing after the self-curing is finished to obtain a polyimide foam material; the method can recycle the polyimide foam waste, fully and effectively utilize the polyimide foam waste, improve the polyimide foam utilization rate and reduce the polyimide foam product cost.
Description
Technical Field
The invention belongs to the technical field of polyimide foam waste recycling, and particularly relates to a recycling method of polyimide foam waste.
Background
The polyimide foam material is a heat insulation material with excellent performances of light weight, low heat conductivity coefficient, high and low temperature resistance, intrinsic flame retardance, environmental protection, no toxicity, irradiation resistance, sound absorption, easy processing and installation and the like, and can be used in the fields of aerospace, ships, rail transit and the like. Along with the vigorous development of the industries, the demands of polyimide foam materials are increased, but waste materials generated in the production and manufacturing processes of the polyimide foam materials are increased, and the polyimide foam waste materials are treated in a traditional mode to pollute the environment and be unfavorable for the effective utilization of resources, so that the recycling of the polyimide foam material waste materials is urgent.
The existing treatment mode of polyimide foam material waste mainly comprises 1. Mixing leftover materials and raw materials, reacting and foaming; 2. decomposing and recycling powder; 3. decomposing and recycling monomers; 4. other materials were prepared. CN 109942884A discloses a method for preparing polyimide foam pipe sleeve by adding aromatic dianhydride into isocyanate and heating, mixing with end-capping agent and polyimide foam leftover materials, placing in an industrial microwave oven for microwave foaming, wherein the technical scheme adopts industrial microwave curing, and the curing process is not easy to control. CN 106432792A discloses a method for preparing polyimide powder by washing, sterilizing and pulverizing polyimide waste, adding a first organic solvent to dissolve and filter, adding a second organic solvent to separate polyimide powder, and finally centrifuging and drying. The method utilizes a chemical decomposition mode to recycle polyimide wastes into polyimide powder, and the yield is 79-81%, but the chemical decomposition recycling amount is smaller, and the method has certain limit on the treatment of more leftover materials. CN 109503614A discloses a method for introducing nitrogen into polyimide waste and adding hydrazine hydrate with a certain content to carry out hydrazinolysis, thus obtaining hydrazine hydrate solution containing aromatic tetra-aromatic bicyclic hydrazine and aromatic diamine, and obtaining diamine and dianhydride monomers by filtering, water washing and other modes respectively. The method has the advantages that the purity of the obtained monomer is over 99 percent, the recovery rate of the monomer is over 97 percent, but the reaction process is complex, and the requirements on equipment and environment are high. CN 110607174A discloses a method for preparing graphene from polyimide by two-stage heating treatment and constant temperature for a period of time, then preparing the product into electrode materials such as rod and sheet, etc. as positive electrode for electrolysis to obtain graphene carbon dots.
Therefore, the prior art also has the problems of difficult full utilization of polyimide foam waste, high operation difficulty, difficult process control and the like, so that the research of a method which has the advantages of high waste recycling rate, energy conservation and environmental protection is significant.
Disclosure of Invention
The invention provides a recycling method of polyimide foam waste aiming at the defects of the prior art.
The method is realized by the following technical scheme:
a recycling method of polyimide foam waste comprises the following steps:
(1) Putting the polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Fully mixing polyimide foam waste powder with dianhydride, a foaming agent, a solvent, an auxiliary agent and an adhesive, adding isocyanate, and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mould to foam and self-cure, and then heating and curing to obtain the polyimide foam material.
In step (2), the dianhydride is 3,3',4' -diphenylether tetracarboxylic dianhydride (ODPA), 2, 3',4' -diphenylether tetracarboxylic dianhydride (alpha-ODPA), 3',4,4' -biphenyltetracarboxylic dianhydride (BPDA), 2, 3',4' -biphenyltetracarboxylic dianhydride (alpha-BPDA), 3', one or more of 4,4' -Benzophenone Tetracarboxylic Dianhydride (BTDA), pyromellitic dianhydride (PMDA), 2-bis [4- (3, 4-phenoxyphenyl) ] propane dianhydride (BPADA), 3',4' -biphenyl sulfone tetracarboxylic dianhydride (DSDA) are mixed;
in the step (2), the foaming agent is one or more of water, methanol, ethanol, acetone, glycol, glycerol, pentaerythritol, isopropanol, glycol butyl ether and polyethylene glycol.
In the step (2), the solvent is one or more of N, N '-Dimethylformamide (DMF), N' -dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), dimethyl sulfoxide (DMSO) and Tetrahydrofuran (THF);
in the step (2), the auxiliary agent is one or more of diethanolamine, triethanolamine, triethylene diamine, dimethylethanolamine, dipropylene glycol, triethylenediamine, organotin and AK series silicone oil.
In the step (2), the adhesive is epoxy resin adhesive.
In step (2), the isocyanate is one or more of polyphenyl polymethylene polyisocyanate (PAPI), toluene Diisocyanate (TDI), diphenylmethane diisocyanate (MDI), hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), xylylene Diisocyanate (XDI), tetramethylxylylene diisocyanate (TMXDI), methylcyclohexane diisocyanate (HTDI).
In the step (2), the mass ratio of the polyimide foam waste powder to dianhydride, foaming agent, solvent, auxiliary agent, adhesive and isocyanate is (50-100): (5-20): (1-5): (5-8): (1-5): (60-110).
In the step (3), the heating and curing are oven heating, the temperature is 180-280 ℃, and the time is 0.5-3 h.
The invention adopts the principle that the baking oven is adopted for heating and curing, the curing mode is simple, the polyimide intermediate is formed through the reaction of dianhydride, isocyanate and the like, polyimide waste powder is uniformly mixed with the polyimide intermediate, and the adhesiveness between the powder and the polyimide intermediate is reinforced through the adhesive, so that 100% recovery of foam waste is realized.
The beneficial effects are that:
the method is suitable for polyimide urethane foam with different densities, and has the advantages of high recovery efficiency, simple equipment requirement, high recovery utilization rate, high industrial product efficiency and low recovery cost.
Detailed Description
The following detailed description of the invention is provided in further detail, but the invention is not limited to these embodiments, any modifications or substitutions in the basic spirit of the present examples, which still fall within the scope of the invention as claimed.
Example 1
The embodiment provides a recycling method of polyimide foam waste, which specifically comprises the following steps:
(1) Placing polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Taking 8kg of polyimide foam waste powder, fully mixing 8kg of polyimide foam waste powder with 0.8kg of 3,3',4' -diphenyl ether tetracarboxylic dianhydride, 0.2kg of methanol, 0.6kg of N, N ' -dimethylformamide, 0.2kg of triethanolamine and 0.1kg of epoxy resin adhesive, and then adding 10kg of polyphenyl polymethylene polyisocyanate and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mold for foaming and self-curing, then placing the polyimide foam precursor into an oven, heating and curing for 1h at 200 ℃, cooling and demolding after curing is finished to obtain a polyimide foam material;
the results show that: recovery rate is 100%, density is 20kg/m 3 The thermal conductivity was 0.047W/mK, the limiting oxygen index was 30%, and the tensile strength was 425kPa.
Example 2
The embodiment provides a recycling method of polyimide foam waste, which specifically comprises the following steps:
(1) Placing polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Taking 8kg of polyimide foam waste powder, fully mixing 8kg of polyimide foam waste powder with 0.8kg of 3,3',4' -biphenyl tetracarboxylic dianhydride, 0.2kg of ethylene glycol, 0.6kg of dimethyl sulfoxide, 0.2kg of triethylene diamine and 0.1kg of epoxy resin adhesive, then adding 10kg of diphenylmethane diisocyanate, and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mold for foaming and self-curing, then placing the polyimide foam precursor into an oven for heating and curing for 1h at 200 ℃, and cooling and demolding after curing to obtain a polyimide foam material;
the results show that: recovery rate is 100%, density is 20kg/m 3 The thermal conductivity is 0.041W/m.K, the limiting oxygen index is 35%, and the tensile strength is 536kPa.
Example 3
The embodiment provides a recycling method of polyimide foam waste, which specifically comprises the following steps:
(1) Placing polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Taking 8kg of polyimide foam waste powder, fully mixing 8kg of polyimide foam waste powder with 0.8kg of pyromellitic dianhydride, 0.2kg of polyethylene glycol, 0.6kg of tetrahydrofuran, 0.2kg of organotin and 0.1kg of epoxy resin glue, and then adding 10kg of hexamethylene diisocyanate and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mold for foaming and self-curing, then placing the polyimide foam precursor into an oven for heating and curing for 1h at 200 ℃, and cooling and demolding after curing to obtain a polyimide foam material;
the results show that: the recovery rate is 100 percent,density of 20kg/m 3 The thermal conductivity was 0.052W/mK, the limiting oxygen index was 34%, and the tensile strength was 478kPa.
The limit oxygen index of the polyimide foam material prepared by using the polyimide foam waste material is not different from that of the finished product material, the heat conductivity coefficient of the finished product polyimide foam material is 0.035W/m.K, and the heat conductivity coefficient of the waste molding material is slightly larger than that of the finished product, because the existence of the waste powder has larger pore gap, so that the heat conductivity coefficient is increased; the tensile strength of the finished polyimide foam material is about 80kPa, and the tensile strength of the waste molding material is greatly increased, because the polyimide foam waste is crushed and then molded in the material to play a certain supporting role, and the structural combination of the adhesive reinforcing material is added, so that the mechanical property of the material is enhanced; compared with the cost of the finished product, the cost of recycling the waste is reduced by 50%, so that the recycling method can effectively utilize the waste of the product, can be utilized in the field with lower requirements on heat preservation performance, realizes green production and reduces waste.
Example 4
The embodiment provides a recycling method of polyimide foam waste, which specifically comprises the following steps:
(1) Placing polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Taking and fully mixing 5kg of polyimide foam waste powder with 0.5kg of DSDA0.5kg, 0.1kg of ethylene glycol butyl ether, 0.5kg of DMAC, 0.1kg of dipropylene glycol and 0.3kg of epoxy resin glue, and then adding 6kg of TDI and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mould to foam and self-cure, then placing the polyimide foam precursor into an oven to heat and cure for 3 hours at the temperature of 280 ℃, cooling and demoulding after curing to obtain the polyimide foam material.
Example 5
The embodiment provides a recycling method of polyimide foam waste, which specifically comprises the following steps:
(1) Placing polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Mixing 10kg of polyimide foam waste powder with 2kg of BPADA, 0.5kg of water, 0.8kg of NMP, 0.5kg of AK series silicone oil and 0.5kg of epoxy resin glue, and then adding 11kg of HTDI and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mould to foam and self-solidify, then placing the polyimide foam precursor into an oven to heat and solidify for 0.5h at 180 ℃, cooling and demoulding after solidification to obtain the polyimide foam material.
Finally, it should be noted that the above embodiments are merely representative examples of the present invention. Obviously, the technical solution of the invention is not limited to the above-described embodiments, but many variations are possible. All modifications directly derived or suggested to one skilled in the art from the present disclosure should be considered as being within the scope of the present invention.
Claims (7)
1. The recycling method of polyimide foam waste is characterized by comprising the following steps:
(1) Putting the polyimide foam waste into a pulverizer for pulverizing to obtain polyimide foam waste powder;
(2) Fully mixing polyimide foam waste powder with dianhydride, a foaming agent, a solvent, an auxiliary agent and an adhesive, adding isocyanate, and stirring to obtain a polyimide foam precursor;
(3) Pouring the polyimide foam precursor into a mould to foam and self-cure, and heating and curing to obtain a polyimide foam material;
in the step (2), the adhesive is epoxy resin adhesive;
in the step (2), the mass ratio of the polyimide foam waste powder to dianhydride, foaming agent, solvent, auxiliary agent, adhesive and isocyanate is (50-100): (5-20): (1-5): (5-8): (1-5): (60-110).
2. The method for recycling polyimide foam waste according to claim 1, wherein in the step (2), the dianhydride is 3,3',4' -diphenyl ether tetracarboxylic dianhydride (ODPA), 2, 3',4' -diphenyl ether tetracarboxylic dianhydride (alpha-ODPA), 3',4' -biphenyl tetracarboxylic dianhydride (BPDA), 2, 3',4' -biphenyltetracarboxylic dianhydride (α -BPDA), 3',4' -Benzophenone Tetracarboxylic Dianhydride (BTDA), pyromellitic dianhydride (PMDA), 2-bis [4- (3, 4-phenoxyphenyl) ] propane dianhydride (BPADA), 3',4' -biphenyl sulfone tetracarboxylic dianhydride (DSDA).
3. The method for recycling and reusing polyimide foam waste according to claim 1, wherein in the step (2), the foaming agent is one or more of water, methanol, ethanol, acetone, ethylene glycol, glycerol, pentaerythritol, isopropanol, ethylene glycol butyl ether and polyethylene glycol.
4. The method for recycling polyimide foam waste according to claim 1, wherein in the step (2), the solvent is one or more of N, N '-Dimethylformamide (DMF), N' -dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), dimethylsulfoxide (DMSO), and Tetrahydrofuran (THF).
5. The method for recycling and reusing polyimide foam waste according to claim 1, wherein in the step (2), the auxiliary agent is one or more of diethanolamine, triethanolamine, triethylenediamine, dimethylethanolamine, dipropylene glycol, triethylenediamine, organotin and AK-series silicone oil.
6. The method for recycling polyimide foam waste according to claim 1, wherein in the step (2), the isocyanate is one or more of PAPI, TDI, MDI, HDI, IPDI, XDI, TMXDI, HTDI.
7. The recycling method of polyimide foam waste according to claim 1, wherein in the step (3), the heating and curing are oven heating, the temperature is 180-280 ℃ and the time is 0.5-3 h.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101812232A (en) * | 2010-04-09 | 2010-08-25 | 北京航空航天大学 | Polyimide foam and preparation method thereof |
| CN107540839A (en) * | 2016-06-27 | 2018-01-05 | 上海康达化工新材料股份有限公司 | A kind of heat-insulated Polyimide foams of Lightweight acoustical and preparation method thereof |
| CN109942884A (en) * | 2019-04-01 | 2019-06-28 | 自贡中天胜新材料科技有限公司 | A kind of preparation method of polyimide foam and its heat-insulating cover |
| CN110655790A (en) * | 2019-09-27 | 2020-01-07 | 贵州航天天马机电科技有限公司 | Production method of polyimide foam material |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101812232A (en) * | 2010-04-09 | 2010-08-25 | 北京航空航天大学 | Polyimide foam and preparation method thereof |
| CN107540839A (en) * | 2016-06-27 | 2018-01-05 | 上海康达化工新材料股份有限公司 | A kind of heat-insulated Polyimide foams of Lightweight acoustical and preparation method thereof |
| CN109942884A (en) * | 2019-04-01 | 2019-06-28 | 自贡中天胜新材料科技有限公司 | A kind of preparation method of polyimide foam and its heat-insulating cover |
| CN110655790A (en) * | 2019-09-27 | 2020-01-07 | 贵州航天天马机电科技有限公司 | Production method of polyimide foam material |
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