JP2010138402A - Method of processing resin - Google Patents
Method of processing resin Download PDFInfo
- Publication number
- JP2010138402A JP2010138402A JP2010012074A JP2010012074A JP2010138402A JP 2010138402 A JP2010138402 A JP 2010138402A JP 2010012074 A JP2010012074 A JP 2010012074A JP 2010012074 A JP2010012074 A JP 2010012074A JP 2010138402 A JP2010138402 A JP 2010138402A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- carbon material
- treatment liquid
- anhydride
- acid anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 229920005989 resin Polymers 0.000 title claims abstract description 32
- 239000011347 resin Substances 0.000 title claims abstract description 32
- 239000007788 liquid Substances 0.000 claims abstract description 49
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003109 Karl Fischer titration Methods 0.000 claims abstract description 4
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 4
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims abstract 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims abstract 2
- 235000019798 tripotassium phosphate Nutrition 0.000 claims abstract 2
- 238000003672 processing method Methods 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 abstract description 54
- 229920000647 polyepoxide Polymers 0.000 abstract description 54
- 239000003575 carbonaceous material Substances 0.000 abstract description 48
- 239000002131 composite material Substances 0.000 abstract description 33
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 229910001868 water Inorganic materials 0.000 abstract description 14
- 238000000197 pyrolysis Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 19
- 150000001339 alkali metal compounds Chemical class 0.000 description 19
- 238000000926 separation method Methods 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 12
- -1 alkali metal salt Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000005979 thermal decomposition reaction Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920000049 Carbon (fiber) Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004917 carbon fiber Substances 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XINCECQTMHSORG-UHFFFAOYSA-N Isoamyl isovalerate Chemical compound CC(C)CCOC(=O)CC(C)C XINCECQTMHSORG-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 description 2
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-N 2,2-diethylpropanedioic acid Chemical compound CCC(CC)(C(O)=O)C(O)=O LTMRRSWNXVJMBA-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- HQLKZWRSOHTERR-UHFFFAOYSA-N 2-Ethylbutyl acetate Chemical compound CCC(CC)COC(C)=O HQLKZWRSOHTERR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
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- 150000002222 fluorine compounds Chemical class 0.000 description 1
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
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- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 description 1
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- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
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- 150000002596 lactones Chemical class 0.000 description 1
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
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- 239000012778 molding material Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 description 1
- LJAGLQVRUZWQGK-UHFFFAOYSA-N oxecane-2,10-dione Chemical compound O=C1CCCCCCCC(=O)O1 LJAGLQVRUZWQGK-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 229930193351 phorone Natural products 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 206010035653 pneumoconiosis Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical group CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Processes Of Treating Macromolecular Substances (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
Description
本発明は、航空機部品、自動車部品、運動器具、電気器具、その他各種構造材に用いられる炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液および分離方法に関する。 The present invention relates to a treatment liquid and a separation method for a carbon material / anhydride-cured epoxy resin composite material used for aircraft parts, automobile parts, exercise equipment, electrical equipment, and other various structural materials.
酸無水物硬化エポキシ樹脂は、強度、耐熱性、電気特性、炭素材料との接着性などに優れるため、炭素材料／樹脂硬化物複合材料として広く利用されている。しかしながら、酸無水物硬化エポキシ樹脂は熱硬化するため、加熱しても溶融せず、汎用溶剤には不溶になるため、再利用が困難であった。そこで、粉砕等によって機械的に分離を行っているが、得られた樹脂硬化物と炭素材料の分離物の純度は著しく低い。また、粉砕された炭素繊維は繊維長が短く、再び炭素繊維／樹脂複合材料に使用した場合には、その強度は著しく低下する。 An acid anhydride cured epoxy resin is widely used as a carbon material / resin cured material composite material because it is excellent in strength, heat resistance, electrical properties, adhesion to a carbon material, and the like. However, since the acid anhydride-cured epoxy resin is thermally cured, it does not melt even when heated and becomes insoluble in a general-purpose solvent, so that it is difficult to reuse. Therefore, although mechanical separation is performed by pulverization or the like, the purity of the obtained cured resin product and carbon material is extremely low. In addition, the pulverized carbon fiber has a short fiber length, and when used again for a carbon fiber / resin composite material, its strength is significantly reduced.
本発明者らは、常圧下、２００℃以下の低い温度でエポキシ樹脂硬化物を分解除去し、プリント配線板の回路を形成するための処理液として、アルカリ金属化合物、アミド系溶媒、アルコール系溶媒からなるエッチング液を開示した（特許文献１〜５参照）。しかし、これらの発明はいずれも樹脂硬化物の一部分をエッチング除去することにより、電気回路等を形成することを目的とするものであり、炭素材料とエポキシ樹脂硬化物の分離を目的とするものではない。さらに、エッチング対象として、無機充填剤、無機繊維を含むことは必須ではなく、このことからも炭素材料と酸無水物硬化エポキシ樹脂の分離を目的とするものではないことは明らかである。 The present inventors decomposed and removed the cured epoxy resin at a low temperature of 200 ° C. or lower under normal pressure, and used as a treatment liquid for forming a circuit of a printed wiring board, an alkali metal compound, an amide solvent, an alcohol solvent. The etching liquid which consists of was disclosed (refer patent documents 1-5). However, all of these inventions are intended to form an electric circuit by etching away a part of the cured resin, and not intended to separate the carbon material and the cured epoxy resin. Absent. Furthermore, it is not essential to include an inorganic filler and inorganic fiber as an etching target, and it is clear that this is not intended to separate the carbon material and the acid anhydride-cured epoxy resin.
無機物と樹脂硬化物の分離を目的とする発明としては、特許文献６〜８等に示されるように、成形材料からシリカを分離回収するために、９００℃以上の温度で樹脂を熱分解させる方法がある。また、特許文献９には、熱硬化性樹脂の熱分解により無機物を回収する方法が示されている。これらの発明は、樹脂を熱分解してガス化するため、エネルギーとして再利用することはできても、樹脂分解物を再利用することはできない。また、樹脂を分解させるためには、通常３００℃以上の高温が必要であり、炭素材料は変質して再利用できなくなる場合がある。 As an invention aiming at separation of an inorganic substance and a cured resin product, as shown in Patent Documents 6 to 8, etc., a method of thermally decomposing a resin at a temperature of 900 ° C. or higher in order to separate and recover silica from a molding material There is. Patent Document 9 discloses a method for recovering an inorganic substance by thermal decomposition of a thermosetting resin. In these inventions, since the resin is thermally decomposed and gasified, it can be reused as energy, but the resin decomposed product cannot be reused. Further, in order to decompose the resin, a high temperature of 300 ° C. or higher is usually required, and the carbon material may be altered and cannot be reused.
エポキシ樹脂の熱分解法としては、特許文献１０に示されるように、水酸基の供給源とともに熱分解する方法もあるが、当該公報に明記されているように、熱分解に必要な温度は一般に３７０〜３９０℃である。当該公報では、「樹脂の熱分解は、樹脂が約３４０〜９００℃の温度範囲内、特に３５０℃〜４５０℃前後となるように加熱するのが好ましい」と述べている。したがって、３００℃以下の温度で、特殊な溶媒、触媒を使用して分解にすることは、一般的な意味での「熱分解」には当たらないことは明らかである。 As a thermal decomposition method of an epoxy resin, as disclosed in Patent Document 10, there is a method of thermal decomposition together with a hydroxyl group supply source. However, as specified in the publication, a temperature required for the thermal decomposition is generally 370. ~ 390 ° C. The publication states that "in the thermal decomposition of the resin, it is preferable to heat the resin within a temperature range of about 340 to 900 ° C, particularly around 350 to 450 ° C." Therefore, it is obvious that decomposition using a special solvent or catalyst at a temperature of 300 ° C. or less does not correspond to “thermal decomposition” in a general sense.
酸無水物硬化エポキシ樹脂にはエステル結合が存在するが、エステル結合を多量に有する熱硬化性樹脂として不飽和ポリエステル樹脂硬化物がある。これを化学的に分解する方法としては、特許文献１１に示されるような塩基と親水性溶媒を用いる方法、特許文献１２に示されるような塩基と一価のアルコールを用いる方法、特許文献１３に示されるようなグリコールを用いる方法、特許文献１４に示されるようなジカルボン酸またはジアミンを用いる方法、特許文献１５に示されるようなジエタノールアミンを用いる方法、特許文献１６に示されるように超臨界アルコールを用いる方法などがある。これらの方法は腐食性の化学物質を使用するため、安全上好ましくない。また、これら腐食性の化学物質を使用しない場合には、分解速度が著しく遅いため、処理前に粉砕等の操作が必要となり、安全衛生面並びに経済面から実用的ではない。また、超臨界あるいは亜臨界流体を利用する場合は、高圧容器を必要とするため、安全上並びに経済性の点で好ましくない。 An acid anhydride-cured epoxy resin has an ester bond, but there is an unsaturated polyester resin cured product as a thermosetting resin having a large amount of ester bonds. As a method of chemically decomposing this, a method using a base and a hydrophilic solvent as shown in Patent Document 11, a method using a base and a monovalent alcohol as shown in Patent Document 12, A method using glycol as shown, a method using dicarboxylic acid or diamine as shown in Patent Document 14, a method using diethanolamine as shown in Patent Document 15, and a supercritical alcohol as shown in Patent Document 16. There are methods to use. Since these methods use corrosive chemicals, they are not preferable for safety. In addition, when these corrosive chemicals are not used, the decomposition rate is extremely slow, and thus operations such as pulverization are required before processing, which is not practical from the viewpoints of health and safety and economy. In addition, when a supercritical or subcritical fluid is used, a high pressure vessel is required, which is not preferable in terms of safety and economy.
本発明は、前述の通り、従来技術では解決できなかった炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離技術の課題を解決することを目的とする。すなわち、安全衛生上および経済性に優れ、なおかつ通常熱分解に必要とされる温度以下で効率的に炭素材料／酸無水物硬化エポキシ樹脂複合材料を処理し、分離することのできる処理液および分離方法を提供する。 As described above, an object of the present invention is to solve the problem of the carbon / acid anhydride-cured epoxy resin composite technology that could not be solved by the prior art. That is, a treatment liquid and separation that are excellent in safety and hygiene and economy, and that can efficiently process and separate a carbon material / anhydride-cured epoxy resin composite material at a temperature lower than ordinarily required for thermal decomposition. Provide a method.
上記課題を解決するために、本発明は、以下の（１）〜（１４）をその特徴とするものである。 In order to solve the above problems, the present invention is characterized by the following (1) to (14).
（１）水分を除去したアルカリ金属化合物と、有機溶媒と、を含むことを特徴とする炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (1) A carbon material / acid anhydride cured epoxy resin composite treatment liquid comprising an alkali metal compound from which moisture has been removed and an organic solvent.
（２）前記水分を除去したアルカリ金属化合物の水分含有率が５％未満であることを特徴とする上記（１）記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (2) The carbon material / acid anhydride cured epoxy resin composite treatment liquid according to (1) above, wherein the moisture content of the alkali metal compound from which moisture has been removed is less than 5%.
（３）前記アルカリ金属化合物がアルカリ金属塩であることを特徴とする上記（１）または（２）記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (3) The treatment liquid for a carbon material / acid anhydride-cured epoxy resin composite material according to (1) or (2), wherein the alkali metal compound is an alkali metal salt.
（４）前記アルカリ金属塩がアルカリ金属リン酸塩であることを特徴とする上記（３）記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (4) The treatment liquid for a carbon material / acid anhydride-cured epoxy resin composite material according to (3), wherein the alkali metal salt is an alkali metal phosphate.
（５）前記有機溶媒がアルコール系溶媒であることを特徴とする上記（１）〜（４）のいずれか１項記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (5) The treatment liquid for a carbon material / acid anhydride-cured epoxy resin composite material according to any one of (1) to (4) above, wherein the organic solvent is an alcohol solvent.
（６）前記アルコール系溶媒がモノアルコール系溶媒であることを特徴とする上記（５）記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (6) The treatment liquid for a carbon material / acid anhydride-cured epoxy resin composite material according to the above (5), wherein the alcohol solvent is a monoalcohol solvent.
（７）処理対象となる炭素材料／酸無水物硬化エポキシ樹脂複合材料の炭素材料が、炭素繊維であることを特徴とする上記（１）〜（６）のいずれか１項記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の処理液。 (7) The carbon material / any one of (1) to (6) above, wherein the carbon material of the carbon material / acid anhydride cured epoxy resin composite material to be treated is carbon fiber Treatment liquid for acid anhydride cured epoxy resin composite material.
（８）上記（１）〜（７）のいずれか１項記載の処理液を用いて炭素材料／酸無水物硬化エポキシ樹脂複合材料の樹脂硬化物のみを分解および／または溶解処理する工程、および前記処理液中に含まれる炭素材料と樹脂硬化物の溶液及び／または分解生成物とを分離する工程、を含むことを特徴とする炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (8) a step of decomposing and / or dissolving only the resin cured product of the carbon material / acid anhydride-cured epoxy resin composite using the treatment liquid according to any one of (1) to (7), and A method for separating a carbon material / anhydride-cured epoxy resin composite material, comprising: separating a carbon material and a solution and / or decomposition product of a resin cured product contained in the treatment liquid.
（９）大気圧下で行うことを特徴とする上記（８）記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (9) The carbon material / acid anhydride-cured epoxy resin composite material separation method according to the above (8), which is carried out under atmospheric pressure.
（１０）処理中における前記処理液の温度が２５０℃以下であること特徴とする上記（８）または（９）記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (10) The carbon material / acid anhydride cured epoxy resin composite material separation method according to (8) or (9) above, wherein the temperature of the treatment liquid during treatment is 250 ° C. or less.
（１１）処理中における前記処理液の温度が２００℃以下であることを特徴とする上記（８）〜（１０）のいずれか１項記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (11) Separation of carbon material / acid anhydride cured epoxy resin composite material according to any one of (8) to (10) above, wherein the temperature of the treatment liquid during treatment is 200 ° C. or less Method.
（１２）処理対象となる炭素材料／酸無水物硬化エポキシ樹脂複合材料が１．０ｃｍ３以上１．５ｍ３以下の大きさであることを特徴とする上記（８）〜（１１）のいずれか１項記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (12) Any of (8) to (11) above, wherein the carbon material / acid anhydride cured epoxy resin composite material to be treated has a size of 1.0 cm 3 or more and 1.5 m 3 or less. 2. A method for separating the carbon material / acid anhydride cured epoxy resin composite material according to item 1.
（１３）分離された前記炭素材料が再利用可能であることを特徴とする上記（８）〜（１２）のいずれか１項記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (13) The carbon material / acid anhydride-cured epoxy resin composite separation method according to any one of (8) to (12) above, wherein the separated carbon material is reusable.
（１４）分離された樹脂硬化物の溶液及び／または分解生成物が再利用可能であることを特徴とする上記（８）〜（１３）のいずれか１項記載の炭素材料／酸無水物硬化エポキシ樹脂複合材料の分離方法。 (14) The carbon material / acid anhydride curing according to any one of (8) to (13) above, wherein the solution and / or decomposition product of the separated resin cured product is reusable. Separation method of epoxy resin composite material.
本発明によれば、炭素材料／酸無水物硬化エポキシ樹脂複合材料を処理する際に水分を除去したアルカリ金属化合物を含む処理液を用いることで、安全衛生上および経済性に優れ、なおかつ通常熱分解に必要とされる温度以下で効率的に炭素材料／酸無水物硬化エポキシ樹脂複合材料を処理し、これを炭素材料と樹脂硬化物の溶液および／または分解生成物とに分離することができる。 According to the present invention, by using a treatment liquid containing an alkali metal compound from which moisture has been removed when treating a carbon material / anhydride-cured epoxy resin composite material, it is excellent in safety and hygiene and economy, and is usually heated. The carbon material / anhydride cured epoxy resin composite can be efficiently processed below the temperature required for decomposition and separated into a carbon material and a cured resin solution and / or a decomposition product. .
本発明の処理対象となる炭素材料／酸無水物硬化エポキシ樹脂複合材料に含まれる炭素材料は、炭素を主成分とする材料であればどのようなものでもよく、例えば、アクリルを原料とする炭素繊維、ピッチを原料とする炭素繊維、カーボンブラック、グラファイト、活性炭、ダイヤモンド、コークス、カーボンナノチューブ、フラーレンあるいはこれらの混合物などがある。 The carbon material contained in the carbon material / acid anhydride cured epoxy resin composite material to be treated in the present invention may be any material as long as it is a material mainly composed of carbon. Examples thereof include carbon, carbon fiber, carbon black, graphite, activated carbon, diamond, coke, carbon nanotube, fullerene, or a mixture thereof.
本発明において処理対象となる炭素材料／酸無水物硬化エポキシ樹脂複合材料に含まれる酸無水物硬化エポキシ樹脂は、エポキシ樹脂とその硬化剤である無水物を反応させて得ることができ、この他にも架橋剤、硬化促進剤、触媒、エラストマ、難燃剤、炭素材料以外の非相溶性材料などを使用しうる。 The acid anhydride-cured epoxy resin contained in the carbon material / acid anhydride-cured epoxy resin composite material to be treated in the present invention can be obtained by reacting an epoxy resin with an anhydride that is a curing agent thereof. In addition, crosslinking agents, curing accelerators, catalysts, elastomers, flame retardants, incompatible materials other than carbon materials, and the like can be used.
エポキシ樹脂としては、分子内にエポキシ樹脂を有するものであればどのようなものでもよく、例えば、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、
ビスフェノールＳ型エポキシ樹脂、脂環式エポキシ樹脂、脂肪族鎖状エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビスフェノールＡノボラック型エポキシ樹脂、ビフェノールのジグリシジリエーテル化物、ナフタレンジオールのジグリシジリエーテル化物、フェノール類のジグリシジリエーテル化物、アルコール類のジグリシジリエーテル化物、及びこれらのアルキル置換体、ハロゲン化物、水素添加物などがある。これらは併用しても良く、エポキシ樹脂以外の成分が不純物として含まれていてもよい。
As the epoxy resin, any epoxy resin can be used as long as it has an epoxy resin in the molecule. For example, bisphenol A type epoxy resin, bisphenol F type epoxy resin,
Bisphenol S epoxy resin, cycloaliphatic epoxy resin, aliphatic chain epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, bisphenol A novolac epoxy resin, diglycidyl etherified product of biphenol, naphthalenediol Examples thereof include a silylid ether compound, a diglycidyl ether compound of phenols, a diglycidyl ether compound of alcohols, and alkyl-substituted products, halides and hydrogenated products thereof. These may be used in combination, and components other than the epoxy resin may be contained as impurities.
酸無水物の例としては、無水フタル酸、テトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸、無水メチルナジック酸、ドデシル無水コハク酸、無水クロレンディック酸、無水イタコン酸、無水コハク酸、無水マレイン酸、無水ピロメリット酸、ベンゾフェノンテトラカルボン酸二無水物、エチレングリコールビストリメリテート、メチルシクロヘキセンテトラカルボン酸二無水物、グリセロールトリストリメリテート、ポリアジピン酸無水物、ポリアゼライン酸無水物、ポリセバシン酸無水物、無水トリメリット酸などがある。これらの酸無水物系硬化剤は、単独、或いは、組み合わせて用いることもできる。 Examples of acid anhydrides include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyl nadic anhydride, dodecyl succinic anhydride, chlorendic anhydride , Itaconic anhydride, succinic anhydride, maleic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, ethylene glycol bistrimellitate, methylcyclohexene tetracarboxylic dianhydride, glycerol trislimitate, polyadipic anhydride Products, poly azelaic anhydride, poly sebacic anhydride, trimellitic anhydride and the like. These acid anhydride curing agents can be used alone or in combination.
硬化促進剤としては、例えば、第三級アミン、イミダゾール類、第四級アンモニウム塩、有機リン化合物等があるが、これに限定されるものではない。 Examples of the curing accelerator include, but are not limited to, tertiary amines, imidazoles, quaternary ammonium salts, and organic phosphorus compounds.
上記炭素材料と酸無水物硬化エポキシ樹脂、ならびに任意の成分を混合し、室温から２５０℃程度の範囲で所定時間加熱することで処理対象となる炭素材料／酸無水物硬化エポキシ樹脂複合材料得ることができる。 Obtaining a carbon material / acid anhydride cured epoxy resin composite material to be treated by mixing the above carbon material, acid anhydride cured epoxy resin, and optional components, and heating for a predetermined time in the range of room temperature to about 250 ° C. Can do.
本発明の処理液は、水分を除去したアルカリ金属化合物と有機溶媒とを必須成分として含むことを特徴とするものである。なお、本発明において、「水分を除去したアルカリ金属化合物」とは、アルカリ金属化合物の水和物を乾燥することによりその水分を除去したもの、もしくはアルカリ金属化合物の無水物を意味し、好ましくはその水分含有率は５％以下であり、より好ましくは２％以下であり、特に好ましくは１％以下である。５％を超える水分がアルカリ金属化合物に含まれていると、処理効率を低下させる可能性があるが、１％以下であれば水分の影響はほとんど顕れない。なお、水分含有率は、カールフィッシャー滴定法を用いて測定することが可能である。 The treatment liquid of the present invention comprises an alkali metal compound from which moisture has been removed and an organic solvent as essential components. In the present invention, the term “alkali metal compound from which moisture has been removed” means an alkali metal compound from which moisture has been removed by drying an alkali metal compound hydrate, or an alkali metal compound anhydride, preferably The water content is 5% or less, more preferably 2% or less, and particularly preferably 1% or less. If the alkali metal compound contains more than 5% moisture, the treatment efficiency may be reduced, but if it is 1% or less, the influence of moisture hardly appears. The water content can be measured using the Karl Fischer titration method.
上記アルカリ金属化合物としては、リチウム、ナトリウム、カリウム、ルビジウム、セシウム等のアルカリ金属を含む化合物であればどのようなものでもよく、例えば、リチウム、ナトリウム、カリウム、ルビジウム、セシウム等の水素化物、水酸化物、ホウ水素化物、アミド化合物、フッ化物、塩化物、臭化物、ヨウ化物、ホウ酸塩、リン酸塩、炭酸塩、硫酸塩、硝酸塩、有機酸塩、アルコラート、フェノラートなどがある。中でもアルカリ金属塩は、有害性が少ないことから好ましい。さらに、アルカリ金属リン酸塩は、酸無水物硬化エポキシ樹脂を分解し、溶解する作用が強い上に、取り扱いが容易でかつ安全であるためより好ましい。これらの化合物は単独で使用しても、数種類を混合して使用してもよい。また、アルカリ金属化合物以外に、どのようなものを併用してもよく、不純物が含まれていてもかまわない。 The alkali metal compound may be any compound as long as it contains an alkali metal such as lithium, sodium, potassium, rubidium, and cesium. For example, hydride such as lithium, sodium, potassium, rubidium, and cesium, water There are oxides, borohydrides, amide compounds, fluorides, chlorides, bromides, iodides, borates, phosphates, carbonates, sulfates, nitrates, organic acid salts, alcoholates, phenolates and the like. Of these, alkali metal salts are preferred because they are less harmful. Furthermore, the alkali metal phosphate is more preferable because it has a strong action of decomposing and dissolving the acid anhydride-cured epoxy resin and is easy to handle and safe. These compounds may be used alone or in combination of several kinds. In addition to the alkali metal compound, any material may be used in combination, and impurities may be contained.
アルカリ金属化合物の水分を除去する方法は、アルカリ金属化合物が分解もしくは酸化等の変質をしない条件下における方法であればよく、加熱による乾燥、減圧乾燥、凍結乾燥、乾燥剤を利用する乾燥などがある。 The method for removing the moisture of the alkali metal compound may be a method under conditions where the alkali metal compound is not decomposed or altered, such as oxidation, such as drying by heating, drying under reduced pressure, freeze drying, drying using a desiccant, etc. is there.
加熱による乾燥の場合、加熱温度の範囲は１００℃以上熱分解温度以下であることが好ましい。１００℃以下では効率よく水分を除去できない可能性があり、熱分解温度以上では、加熱後の塩を処理液に添加しても、酸無水物硬化エポキシ樹脂の分解もしくは溶解が生じない可能性がある。 In the case of drying by heating, the range of the heating temperature is preferably 100 ° C. or more and the pyrolysis temperature or less. There is a possibility that moisture cannot be efficiently removed at a temperature of 100 ° C. or lower, and at a temperature higher than the thermal decomposition temperature, there is a possibility that the acid anhydride-cured epoxy resin will not be decomposed or dissolved even if a salt after heating is added to the treatment liquid. is there.
１００℃以上の加熱で分解等が生じる塩は、減圧下で乾燥してもよい。減圧の範囲は真空から大気圧以下であれば良く、１００℃以下に加熱してもよい。 Salts that decompose when heated at 100 ° C. or higher may be dried under reduced pressure. The range of the reduced pressure may be from vacuum to atmospheric pressure or lower, and may be heated to 100 ° C. or lower.
加熱を行わない場合は、乾燥剤を用いて乾燥しても良い。底部に、塩化カルシウム、青色シリカゲル、濃硫酸、五酸化リンなどの乾燥剤を入れたデシケーター内での乾燥が好ましい。さらにデシケーター内を上記と同様に減圧してもよい。 When not heating, you may dry using a desiccant. Drying in a desiccator containing a desiccant such as calcium chloride, blue silica gel, concentrated sulfuric acid, phosphorus pentoxide at the bottom is preferred. Further, the inside of the desiccator may be decompressed in the same manner as described above.
本発明の処理液に含まれる有機溶媒としては、例えば、アミド系、アルコール系、ケトン系、エーテル系、エステル系などが挙げられるが特に制限されない。これらは単独で使用しても、数種類を混合して使用してもよい。また、これらの溶媒以外に、水以外であればどのようなものを併用してもよく、不純物が含まれていてもかまわない。 Examples of the organic solvent contained in the treatment liquid of the present invention include, but are not particularly limited to, amides, alcohols, ketones, ethers, and esters. These may be used alone or in combination of several kinds. In addition to these solvents, any solvent other than water may be used in combination, and impurities may be contained.
上記アミド系溶媒としては、例えば、ホルムアミド、Ｎ-メチルホルムアミド、Ｎ,Ｎ-ジメチルホルムアミド、Ｎ,Ｎ-ジエチルホルムアミド、アセトアミド、Ｎ-メチルアセトアミド、Ｎ,Ｎ-ジメチルアセトアミド、Ｎ,Ｎ,Ｎ’,Ｎ’-テトラメチル尿素、２-ピロリドン、Ｎ-メチル-２-ピロリドン、カプロラクタム、カルバミド酸エステル等が使用できる。 Examples of the amide solvent include formamide, N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, N, N, N ′. , N′-tetramethylurea, 2-pyrrolidone, N-methyl-2-pyrrolidone, caprolactam, carbamic acid ester and the like can be used.
上記アルコール系溶媒としては、例えば、メタノール、エタノール、１-プロパノール、２-プロパノール、 １-ブタノール、２- ブタノール、iso -ブタノール、tert-ブタノール、１-ペンタノール、２-ペンタノール、３-ペンタノール、２-メチル-１-ブタノール、iso -ペンチルアルコール、tert -ペンチルアルコール、３-メチル-２-ブタノール、ネオペンチルアルコール、１-ヘキサノール、２-メチル-１-ペンタノール、４-メチル-２-ペンタノール、２-エチル-１-ブタノール、１-ヘプタノール、２-ヘプタノール、３-ヘプタノール、シクロヘキサノール、１-メチルシクロヘキサノール、２-メチルシクロヘキサノール、３-メチルシクロヘキサノール、４-メチルシクロヘキサノール、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコール、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、テトラエチレングリコール、ポリエチレングリコール（分子量２００〜４００）、１,２-プロパンジオール、１,３-プロパンジオール、１,２-ブタンジオール、１,３-ブタンジオール、１,４-ブタンジオール、２,３-ブタンジオール、１,５-ペンタンジオール、グリセリン、ジプロピレングリコール、ベンジルアルコールなどがある。 Examples of the alcohol solvent include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, iso-butanol, tert-butanol, 1-pentanol, 2-pentanol, and 3-pen. Tanol, 2-methyl-1-butanol, iso-pentyl alcohol, tert-pentyl alcohol, 3-methyl-2-butanol, neopentyl alcohol, 1-hexanol, 2-methyl-1-pentanol, 4-methyl-2 -Pentanol, 2-ethyl-1-butanol, 1-heptanol, 2-heptanol, 3-heptanol, cyclohexanol, 1-methylcyclohexanol, 2-methylcyclohexanol, 3-methylcyclohexanol, 4-methylcyclohexanol , Ethylene glycol, ethylene glycol monomethyl ether, ethyl Glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol Monoethyl ether, tetraethylene glycol, polyethylene glycol (molecular weight 200-400), 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butane Diol, 2,3-butanediol, 1,5-pentanediol, glycerin, dipropylene glycol It is benzyl alcohol.
上記ケトン系溶媒としては、例えば、アセトン、メチルエチルケトン、２-ペンタノン、３-ペンタノン、２-ヘキサノン、メチルイソブチルケトン、２-ヘプタノン、４-ヘプタノン、ジイソブチルケトン、シクロヘキサノン、メチルシクロヘキサノン、ホロン、イソホロンアセチルアセトン、アセトフェノン、等がある。 Examples of the ketone solvent include acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, methyl isobutyl ketone, 2-heptanone, 4-heptanone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, phorone, isophorone acetylacetone, Acetophenone, etc.
上記エーテル系溶媒としては、例えば、ジプロピルエーテル、ジイソプロピルエーテル、ジブチルエーテル、ジヘキシルエーテル、アニソール、フェネトール、ジオキサン、テトラヒドロフラン、アセタール、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、テトラヒドロフラン、ジオキサン、アセタール等がある。 Examples of the ether solvent include dipropyl ether, diisopropyl ether, dibutyl ether, dihexyl ether, anisole, phenetole, dioxane, tetrahydrofuran, acetal, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, There are dioxane, acetal and the like.
上記エステル系溶媒としては、例えば、ギ酸メチル、ギ酸エチル、ギ酸プロピル、ギ酸ブチル、ギ酸イソブチル、ギ酸ペンチル、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸イソプロピル、酢酸ブチル、酢酸イソブチル、酢酸ペンチル、酢酸イソペンチル、３−メトキシブチルアセタート、２−エチルブチルアセタート、２−エチルヘキシルアセタート、酢酸シクロヘキシル、酢酸ベンジル、プロピオン酸メチル、プロピオン酸エチル、プロピオン酸ブチル、プロピオン酸イソペンチル、乳酸メチル、乳酸エチル、乳酸ブチル、酪酸メチル、酪酸エチル、酪酸ブチル、酪酸イソペンチル、イソ酪酸イソブチル、イソ吉草酸エチル、イソ吉草酸イソペンチル、安息香酸メチル、安息香酸エチル、安息香酸プロピル、安息香酸ブチル、γ−ブチロラクトン、シュウ酸ジエチル、シュウ酸ジブチル、マロン酸ジエチル、サリチル酸メチル、エチレングリコールジアセタート、ホウ酸トリブチル、リン酸トリメチル、リン酸トリエチル等がある。 Examples of the ester solvent include methyl formate, ethyl formate, propyl formate, butyl formate, isobutyl formate, pentyl formate, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, isopentyl acetate. 3-methoxybutyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, cyclohexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, butyl propionate, isopentyl propionate, methyl lactate, ethyl lactate, lactic acid Butyl, methyl butyrate, ethyl butyrate, butyl butyrate, isopentyl butyrate, isobutyl isobutyrate, ethyl isovalerate, isopentyl isovalerate, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, γ-buty Lactones, diethyl oxalate, dibutyl oxalate, diethyl malonic acid, methyl salicylate, ethylene glycol diacetate, tributyl borate, trimethyl phosphate, there is triethyl phosphate.
上記の各種溶媒の中で、アルコール系溶媒はエステル交換反応による分解作用が著しく、酸無水物硬化エポキシ樹脂の溶解性が高いため、好ましい。さらには、水酸基を１個持つモノアルコール系溶媒は、分解生成物の副反応が少なく、より好ましい。 Among the above-mentioned various solvents, alcohol solvents are preferable because the decomposition action by the transesterification reaction is remarkable and the solubility of the acid anhydride-cured epoxy resin is high. Furthermore, a monoalcohol-based solvent having one hydroxyl group is more preferable because it has few side reactions of decomposition products.
本発明の処理液は、有機溶媒に対し、アルカリ金属化合物を０．００１〜５０ｗｔ％の濃度で調整することが好ましい。０．００１ｗｔ％未満では樹脂硬化物の分解速度が著しく遅く、５０ｗｔ％を超えると処理液中に多くの未溶解のアルカリ金属化合物が残存するため、処理液を調整することが困難になり、さらに、樹脂硬化物の処理量が少なくなる。より好ましい濃度は、０．０１〜３０ｗｔ％であり、特に好ましい濃度は、０．１〜２０ｗｔ％である。なお、アルカリ金属化合物は、必ずしもすべてが溶媒に溶解する必要はなく、すべてが溶解していない飽和溶液においても、溶質は平衡状態にあり、アルカリ金属化合物が失活した場合にはそれを補うことができる。 In the treatment liquid of the present invention, the alkali metal compound is preferably adjusted to a concentration of 0.001 to 50 wt% with respect to the organic solvent. If it is less than 0.001 wt%, the decomposition rate of the cured resin is extremely slow, and if it exceeds 50 wt%, many undissolved alkali metal compounds remain in the treatment liquid, making it difficult to adjust the treatment liquid. The processing amount of the cured resin is reduced. A more preferable concentration is 0.01 to 30 wt%, and a particularly preferable concentration is 0.1 to 20 wt%. Note that not all alkali metal compounds need to be dissolved in the solvent, and even in saturated solutions where not all of them are dissolved, the solute is in an equilibrium state, and if the alkali metal compound is deactivated, make up for it. Can do.
本発明の処理液を調整する際の温度はどのような温度でもよいが、常圧下で処理する場合には、使用する溶媒の融点以上、沸点以下であることが好ましい。また、処理液を調整する際の雰囲気は、大気中でも不活性気体中でもよく、常圧下、減圧下、加圧下のいずれでもよい。 The temperature at which the treatment liquid of the present invention is prepared may be any temperature, but when the treatment is performed under normal pressure, it is preferably not less than the melting point and not more than the boiling point of the solvent used. In addition, the atmosphere for adjusting the treatment liquid may be air or an inert gas, and may be under normal pressure, reduced pressure, or increased pressure.
このようにして得られた本発明の処理液には、さらに界面活性剤等の添加剤を添加してもよい。 Additives such as surfactants may be further added to the treatment liquid of the present invention thus obtained.
本発明の分離方法は、上記した本発明の処理液を用いて炭素材料／酸無水物硬化エポキシ樹脂複合材料の樹脂硬化物のみを分解および／または溶解処理し、ついで処理液中に含まれる炭素材料と樹脂硬化物の溶液および／または分解生成物とを分離することをその特徴としている。 In the separation method of the present invention, only the resin cured product of the carbon material / acid anhydride-cured epoxy resin composite material is decomposed and / or dissolved using the treatment liquid of the present invention described above, and then the carbon contained in the treatment liquid. It is characterized by separating the material from the solution and / or decomposition product of the cured resin.
炭素材料／酸無水物硬化エポキシ樹脂複合材料を本発明の処理液により処理する方法としては、特に限定されないが、例えば、複合材料を処理液中に浸漬することによって行うことができ、また、処理速度を高めるために、処理液をスプレー等によって噴霧することもでき、これを高圧で吹き付けることもできる。 The method for treating the carbon material / anhydride cured epoxy resin composite material with the treatment liquid of the present invention is not particularly limited. For example, the treatment can be performed by immersing the composite material in the treatment liquid. In order to increase the speed, the treatment liquid can be sprayed by spraying or the like, and can be sprayed at a high pressure.
処理液の使用時並びに保存時の雰囲気は、大気中でも、窒素、アルゴンまたは二酸化炭素等の不活性気体中でもよく、常圧下、減圧下または加圧下のいずれでもよい。安全性や作業性、経済性に優れる点で、常圧下に処理液を使用・保存することが好ましい。したがって、特定の気体雰囲気や特定の気圧を設定するための装置などを必ずしも必要としない。 The atmosphere during use and storage of the treatment liquid may be air or an inert gas such as nitrogen, argon or carbon dioxide, and may be under normal pressure, reduced pressure or increased pressure. In view of excellent safety, workability, and economy, it is preferable to use and store the treatment liquid under normal pressure. Therefore, a device for setting a specific gas atmosphere or a specific pressure is not necessarily required.
処理中における処理液の温度は、溶媒の融点以上、溶媒の沸点以下であればどのような温度でもよいが、好ましくは室温以上、溶媒の沸点以下の温度である。室温未満では冷却する必要があり、経済的に好ましくなく、有利な点もない。沸点を超えると加圧が不可欠となり、経済面、安全面において好ましくない。また、回収材の品質低下を防ぐためには、処理液の温度を２５０℃以下にして処理することがより好ましく、２００℃以下にして処理することが特に好ましい。処理液の加熱方法は、どのようなものでもよく、処理液を直接ヒーターで加熱することもできるし、処理液の入った容器をヒーターで間接的に加熱することもできる。また、オイル、水、蒸気のような熱媒を用いて加熱してもよい。 The temperature of the treatment liquid during the treatment may be any temperature as long as it is not lower than the melting point of the solvent and not higher than the boiling point of the solvent, but is preferably not lower than room temperature and not higher than the boiling point of the solvent. Below room temperature, cooling is necessary, which is economically undesirable and has no advantages. When the boiling point is exceeded, pressurization becomes indispensable, which is not preferable in terms of economy and safety. In order to prevent the quality of the recovered material from being deteriorated, the treatment liquid is more preferably treated at a temperature of 250 ° C. or lower, particularly preferably 200 ° C. or lower. Any method may be used for heating the treatment liquid, and the treatment liquid can be directly heated by a heater, or the container containing the treatment liquid can be indirectly heated by a heater. Further, heating may be performed using a heat medium such as oil, water, or steam.
処理液で処理する時間は任意であるが、好ましくは０．１〜１００時間である。０．１時間未満では、酸無水物硬化エポキシ樹脂がほとんど溶解及び／または分解せず、１００時間を超えると著しく経済性に劣る。より好ましくは、０．２〜２０時間である。 The time for treatment with the treatment liquid is arbitrary, but is preferably 0.1 to 100 hours. If it is less than 0.1 hour, the acid anhydride-cured epoxy resin hardly dissolves and / or decomposes, and if it exceeds 100 hours, it is extremely inferior in economy. More preferably, it is 0.2 to 20 hours.
処理する際には、処理液を撹拌してもよい。撹拌方法はどのようなものでもよいが、撹拌羽根による方法、噴流を起こす方法、容器を揺動する方法、不活性気体の気泡を用いる方法、超音波による方法などがある。 When processing, you may stir a processing liquid. Any stirring method may be used, such as a method using a stirring blade, a method of generating a jet, a method of swinging a container, a method using bubbles of an inert gas, and a method using ultrasonic waves.
処理する際の炭素材料／酸無水物硬化エポキシ樹脂複合材料の大きさは、特に限定されず、処理装置の規模に合わせて処理可能な大きさであればよい。また、硬化物を切断したのちに処理してもよいが、特に微小にする必要はない。また、破砕してから処理することもできるが、破砕時に発生する粉塵が安全衛生上好ましくなく、塵肺、爆発の危険性があり、さらには経済的にも好ましくない。輸送時の利便性、取り扱い安さ、処理効率などを考慮すると、できれば切断のみにするか、破砕する場合でも最小限に止めるべきであり、好ましくは１．０ｃｍ３以上１．５ｍ３以下程度の大きさとする。 The size of the carbon material / acid anhydride-cured epoxy resin composite material at the time of processing is not particularly limited as long as it can be processed in accordance with the scale of the processing apparatus. Moreover, although it may process after cut | disconnecting hardened | cured material, it is not necessary to make it minute especially. Moreover, although it can process after crushing, the dust generated at the time of crushing is unpreferable on safety and health, there is a danger of a pneumoconiosis and an explosion, and also economically unpreferable. Considering convenience during transportation, ease of handling, processing efficiency, etc., if possible, it should be cut only or minimized even when crushing, preferably about 1.0 cm 3 to 1.5 m 3 Say it.
本発明の処理液にて炭素材料／酸無水物硬化エポキシ樹脂複合材料を処理した後は、処理液中に含まれる炭素材料と樹脂硬化物の溶液及び／または分解生成物とを分離する。分離する方法は、どのような方法でもよいが、例えば、ろ過、沈殿分離、遠心分離あるいはそれらの操作の併用によって分離される。分離された炭素材料は、水、有機溶媒等の溶剤によって洗浄し、乾燥してもよい。 After the carbon material / acid anhydride cured epoxy resin composite material is treated with the treatment liquid of the present invention, the carbon material contained in the treatment liquid and the solution and / or decomposition product of the resin cured product are separated. The separation method may be any method, for example, separation by filtration, precipitation separation, centrifugation, or a combination of these operations. The separated carbon material may be washed with a solvent such as water or an organic solvent and dried.
本発明の分離方法により分離された炭素材料、および樹脂硬化物の溶液及び／または分解生成物は、種々の原材料として再利用することが可能である。 The carbon material separated by the separation method of the present invention and the solution and / or decomposition product of the resin cured product can be reused as various raw materials.
また、一度以上使用された本発明の処理液は、必要とあれば必須成分であるアルカリ金属化合物を補充添加することで、新たな不飽和ポリエステル樹脂硬化物を処理するために繰り返し使用することが可能である。 In addition, the treatment liquid of the present invention that has been used once or more can be used repeatedly to treat new unsaturated polyester resin cured products by supplementing and adding an alkali metal compound as an essential component if necessary. Is possible.
以下、本発明の実施例について説明するが、本発明はこれに限定されるものではない。 Examples of the present invention will be described below, but the present invention is not limited thereto.
（実施例１）
ビスフェノールＡ型エポキシ樹脂（ＤＧＢＰＡ、エポキシ当量１８０）１００ｇ、酸無水物としてメチルテトラヒドロ無水フタル酸（ＭｅＴＨＰＡ）１００ｇ、２−メチルイミダゾール１ｇを混合した後、１０ｍｍに切断した炭素繊維（繊維径１０μｍ）１００ｇを加え、さらに混合した。これを、たて１００ｍｍ×よこ１００ｍｍ×深さ３ｍｍのテフロン（登録商標）製の型に入れ、室温で１時間放置した後、１００℃／１時間＋１２５℃／１時間＋１５０℃／１時間＋１７５℃／１時間＋２００℃／１時間の条件で加熱して、炭素材料／酸無水物硬化エポキシ樹脂複合材料（ＣＦＲＰ）を得た。ここから３０ｍｍ×１０ｍｍ×深さ３ｍｍの試験片を切り出した。
Example 1
100 g of bisphenol A type epoxy resin (DGBPA, epoxy equivalent 180), 100 g of methyltetrahydrophthalic anhydride (MeTHPA) as an acid anhydride and 1 g of 2-methylimidazole, and then cut into 10 mm carbon fiber (fiber diameter 10 μm) 100 g Were added and further mixed. This was put into a Teflon (registered trademark) mold of 100 mm × width 100 mm × depth 3 mm and left at room temperature for 1 hour, then 100 ° C./1 hour + 125 ° C./1 hour + 150 ° C./1 hour + 175 ° C. For 1 hour + 200 ° C./1 hour to obtain a carbon material / anhydride-cured epoxy resin composite material (CFRP). A test piece of 30 mm × 10 mm × depth 3 mm was cut out from here.
処理液は、リン酸三カリウム水和物（７．２７ｇ）から水分を除去したもの５．６６ｇとジエチレングリコールモノメチルエーテル８０．０ｇを試験管に秤量し、室温で穏やかに撹拌して調製した。リン酸三カリウム水和物の水分除去は、リン酸三カリウム水和物７．２７ｇを３００℃の乾燥機中で１時間加熱して行った。その水分量をカールフィッシャー滴定法により測定した結果、１．３％であった。 The treatment liquid was prepared by weighing 5.66 g of tripotassium phosphate hydrate (7.27 g) from which water was removed and 80.0 g of diethylene glycol monomethyl ether in a test tube and gently stirring at room temperature. Water removal from tripotassium phosphate hydrate was performed by heating 7.27 g of tripotassium phosphate hydrate in a dryer at 300 ° C. for 1 hour. As a result of measuring the water content by Karl Fischer titration, it was 1.3%.
処理に際しては、処理液の入った試験管をオイルバスを使用して１５０℃に加温し、ここに試験片を浸漬した。試験片がすべて溶解して炭素材料が実質１００％の純度で回収できるまでの時間を測定した。結果を表１に示す。 In the treatment, the test tube containing the treatment liquid was heated to 150 ° C. using an oil bath, and the test piece was immersed therein. The time until all the test pieces were dissolved and the carbon material was recovered with a purity of substantially 100% was measured. The results are shown in Table 1.
（実施例２）
試験片の原料である酸無水物として、メチルテトラヒドロ無水フタル酸に替えてメチルヘキサヒドロ無水フタル酸（ＭｅＨＨＰＡ）を用いて試験片を作製した以外は、実施例１と同様にして、試験片の処理を行い、その溶解時間を測定した。結果を表１に示す。
(Example 2)
In the same manner as in Example 1, except that methylhexahydrophthalic anhydride (MeHHPA) was used instead of methyltetrahydrophthalic anhydride as the acid anhydride as the raw material of the test piece, The treatment was performed and the dissolution time was measured. The results are shown in Table 1.
（実施例３）
処理液の有機溶媒として、ジエチレングリコールモノメチルエーテルに替えてベンジルアルコールを用いて処理液を調製した以外は、実施例１と同様にして、試験片の処理を行い、その溶解時間を測定した。結果を表１に示す。
(Example 3)
The test piece was treated in the same manner as in Example 1 except that benzyl alcohol was used instead of diethylene glycol monomethyl ether as the organic solvent for the treatment solution, and the dissolution time was measured. The results are shown in Table 1.
（比較例１）
リン酸三カリウム水和物の水分除去を行わなかった以外は、実施例１と同様にして、試験片の処理を行い、その溶解時間を測定した。結果を表１に示す。
(Comparative Example 1)
The test piece was treated and the dissolution time was measured in the same manner as in Example 1 except that water removal of the tripotassium phosphate hydrate was not performed. The results are shown in Table 1.
（比較例２）
リン酸三カリウム水和物の水分除去を行わなかった以外は、実施例２と同様にして、試験片の処理を行い、その溶解時間を測定した。結果を表１に示す。
(Comparative Example 2)
The test piece was treated and the dissolution time was measured in the same manner as in Example 2 except that water removal of the tripotassium phosphate hydrate was not performed. The results are shown in Table 1.
（比較例３）
リン酸三カリウム水和物の水分除去を行わなかった以外は、実施例３と同様にして、試験片の処理を行い、その溶解時間を測定した。結果を表１に示す。
The test piece was treated and the dissolution time was measured in the same manner as in Example 3 except that water removal of tripotassium phosphate hydrate was not performed. The results are shown in Table 1.
実施例１〜実施例３に示したように、リン酸三カリウム水和物から水分を除去したものを処理液の成分として用いた場合には、５時間〜７時間以内に樹脂が溶解したが、水和物をそのまま用いた比較例１〜比較例３での樹脂の溶解に８時間〜１０時間要した。 As shown in Example 1 to Example 3, when the product obtained by removing water from tripotassium phosphate hydrate was used as a component of the treatment liquid, the resin dissolved within 5 to 7 hours. The dissolution of the resin in Comparative Examples 1 to 3 using the hydrate as it was took 8 hours to 10 hours.
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