JP2005343999A - Method for treating unsaturated polyester resin cured product and method for separating composite material - Google Patents
Method for treating unsaturated polyester resin cured product and method for separating composite material Download PDFInfo
- Publication number
- JP2005343999A JP2005343999A JP2004164906A JP2004164906A JP2005343999A JP 2005343999 A JP2005343999 A JP 2005343999A JP 2004164906 A JP2004164906 A JP 2004164906A JP 2004164906 A JP2004164906 A JP 2004164906A JP 2005343999 A JP2005343999 A JP 2005343999A
- Authority
- JP
- Japan
- Prior art keywords
- polyester resin
- unsaturated polyester
- phosphoric acid
- composite material
- cured
- 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.)
- Pending
Links
- 229920006337 unsaturated polyester resin Polymers 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000002131 composite material Substances 0.000 title claims description 30
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 42
- 239000007788 liquid Substances 0.000 claims description 33
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 21
- 239000000945 filler Substances 0.000 claims description 16
- 238000004090 dissolution Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- -1 alkali metal salt Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000007710 freezing Methods 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 4
- 238000003672 processing method Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 24
- 239000011347 resin Substances 0.000 abstract description 24
- 150000003016 phosphoric acids Chemical class 0.000 abstract description 16
- 235000011007 phosphoric acid Nutrition 0.000 abstract description 14
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 239000002202 Polyethylene glycol Substances 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 6
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 4
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 3
- 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
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- HEZQRPHEDDAJTF-UHFFFAOYSA-N chloro(phenyl)methanol Chemical compound OC(Cl)C1=CC=CC=C1 HEZQRPHEDDAJTF-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-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
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-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
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 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
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 description 2
- 239000003049 inorganic solvent Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-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
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-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
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-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
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 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
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
Description
本発明は不飽和ポリエステル樹脂硬化物の処理方法に関する。更に詳しくは、不飽和ポリエステル樹脂硬化物を分解あるいは溶解することにより、再利用することを可能にする処理方法に関する。 The present invention relates to a method for treating a cured unsaturated polyester resin. More specifically, the present invention relates to a treatment method that allows reuse of a cured unsaturated polyester resin by decomposing or dissolving it.
不飽和ポリエステル樹脂硬化物は、耐熱性、機械的性質、耐候性、耐薬品性、耐水性などに優れているため、小型船舶、自動車部品、鉄道車両部品、家具、浴槽、電化製品部品、貯水タンクなどの種々の分野で利用されている。また、不飽和ポリエステル樹脂硬化物はその用途により、樹脂単独で用いられるばかりでなく、充填材などを含有する複合材料として用いられている。 Unsaturated polyester resin cured product has excellent heat resistance, mechanical properties, weather resistance, chemical resistance, water resistance, etc., so it can be used for small vessels, automobile parts, railway vehicle parts, furniture, bathtubs, electrical appliance parts, water storage. It is used in various fields such as tanks. In addition, the unsaturated polyester resin cured product is used not only as a resin alone, but also as a composite material containing a filler or the like depending on its use.
かかる不飽和ポリエステル樹脂は熱硬化性樹脂であり、かつ三次元網目構造を有していることから、成形後は溶融せず、しかも汎用溶媒には不溶化するため、再利用が困難であり、埋め立て処理等により廃棄されていた。また、力学的性質等を向上させるために配合する各種の充填材を溶解することが困難であり、これらの材料も再利用することができなかった。 Since such unsaturated polyester resin is a thermosetting resin and has a three-dimensional network structure, it does not melt after molding and becomes insoluble in a general-purpose solvent. It was discarded by processing. Moreover, it is difficult to dissolve various fillers to be blended in order to improve mechanical properties and the like, and these materials cannot be reused.
しかし、廃棄物問題がますます深刻となっている現在において、熱硬化性樹脂の再利用化技術の開発は急務であり、種々検討されている。例えば、不飽和ポリエステル樹脂を水酸基の供給源となる化合物と加熱して、分解生成物を得る方法が特開平８−８５７３６号公報に示されている。該方法では、樹脂の熱分解を、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して行っており、高温での処理が必要である。また、高温で処理することにより複合材料中に含有されるガラス繊維などの充填材が劣化していしまい、再利用できないといった問題を有している。 However, at the present time when the problem of waste is becoming more and more serious, the development of a technology for reusing thermosetting resins is an urgent matter, and various studies have been made. For example, JP-A-8-85736 discloses a method of heating an unsaturated polyester resin with a compound that serves as a hydroxyl group supply source to obtain a decomposition product. In this method, the resin is thermally decomposed by heating so that the resin is in a temperature range of about 340 to 900 ° C., particularly around 350 ° C. to 450 ° C., and treatment at a high temperature is required. In addition, there is a problem that the filler such as glass fiber contained in the composite material deteriorates due to the treatment at a high temperature and cannot be reused.
また、不飽和ポリエステル樹脂を化学的に分解する方法としては、（１）不飽和ポリエステル中の不飽和基に対して特定モル比のスチレンを含有してなる不飽和ポリエステル樹脂を、塩基と親水性溶媒を含む分解溶液に浸漬して分解する方法（特開平８−１１３６１９号公報）、（２）特定量のポリカプロラクトンを含有してなる不飽和ポリエステル樹脂を、塩基と一価アルコールを含む分解溶液に浸漬して分解する方法（特開平８−１３４３４０号公報）、(３)不飽和ポリエステル樹脂をグリコールを用いて分解する方法（特開平８−２２５６３５号公報）、（４）不飽和ポリエステル樹脂をジカルボン酸またはジアミンを用いて分解する方法（特開平９−２２１５６５号公報）、（５）不飽和ポリエステルをジエタノールアミンを含む分解液に浸漬して分解する方法（特開平９−３１６３１１号公報）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かったり、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、実用的ではないといった問題があった。
以上を鑑み、本発明は通常熱分解に必要とされる温度以下で効率的に不飽和ポリエステル樹脂樹脂硬化物を処理できる処理方法を提供し、これにより不飽和ポリエステル樹脂樹脂硬化物の再利用を容易にしようとするものである。 In view of the above, the present invention provides a treatment method capable of efficiently treating an unsaturated polyester resin resin cured product at a temperature below that normally required for thermal decomposition, thereby allowing reuse of the unsaturated polyester resin resin cured product. It is something that tries to be easy.
この課題を解決するために、本発明ではリン酸類及び有機溶媒を含む処理液中で不飽和ポリエステル樹脂硬化物に超音波振動を与えることにより、分解または溶解することでこれを可能とした。 In order to solve this problem, in the present invention, this is made possible by decomposing or dissolving the unsaturated polyester resin cured product by applying ultrasonic vibration in a treatment liquid containing phosphoric acids and an organic solvent.
本発明によれば、リン酸類及び有機溶媒を含む処理液中で不飽和ポリエステル樹脂硬化物に超音波振動を与えることにより、通常熱分解に必要とされる温度以下で効率的に不飽和ポリエステル樹脂樹脂硬化物を分解または溶解することが可能であり、腐食性が低減された処理液を用いるため、安全性も向上する。 According to the present invention, an unsaturated polyester resin is efficiently produced at a temperature below that normally required for thermal decomposition by applying ultrasonic vibration to the unsaturated polyester resin cured product in a treatment liquid containing phosphoric acids and an organic solvent. The cured resin can be decomposed or dissolved, and since a treatment liquid with reduced corrosiveness is used, safety is improved.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明における処理の対象となる不飽和ポリエステル樹脂硬化物は、特に制限はなく、一般に知られている不飽和ポリエステル樹脂組成物の硬化物に本発明の処理方法を適用することができる。すなわち、不飽和酸及び飽和酸、グリコール類、不飽和ビニルモノマー、重合防止剤、促進剤、充填材などの原料から構成されている。不飽和酸としては無水マレイン酸、フマル酸、メタクリル酸、アクリル酸、イタコン酸等が、飽和酸としては無水フタル酸、イソフタル酸、アジピン酸、テトラブロム無水フタル酸、テレフタル酸、コハク酸等が用いられる。グリコール類としてはプロピレングリコール、エチレングリコール、ジエチレングリコール等が用いられる。 There is no restriction | limiting in particular in the unsaturated polyester resin hardened | cured material used as the object of the process in this invention, The processing method of this invention can be applied to the hardened | cured material of the generally known unsaturated polyester resin composition. That is, it is composed of raw materials such as unsaturated acids and saturated acids, glycols, unsaturated vinyl monomers, polymerization inhibitors, accelerators and fillers. Maleic anhydride, fumaric acid, methacrylic acid, acrylic acid, itaconic acid, etc. are used as unsaturated acids, and phthalic anhydride, isophthalic acid, adipic acid, tetrabromophthalic anhydride, terephthalic acid, succinic acid, etc. are used as saturated acids. It is done. As glycols, propylene glycol, ethylene glycol, diethylene glycol or the like is used.
また、不飽和ビニルモノマーとしては、共重合性の面からスチレンを用いるのが一般的である。さらに、重合防止剤には、キノン類、ヒドロキノン類が良く用いられる。 As the unsaturated vinyl monomer, styrene is generally used from the viewpoint of copolymerization. Furthermore, quinones and hydroquinones are often used as the polymerization inhibitor.
上記原料より不飽和ポリエステル樹脂樹脂硬化物を製造する一般的な方法は、脱水を伴う不飽和ポリエステルの重縮合反応工程と、これを不飽和ビニルモノマーに溶解した後、種々の添加剤を加えその特性を調整する工程からなる。合成中の諸条件として、温度は室温から２５０℃の範囲で硬化させることが多く、反応系内は任意の圧力下で窒素ガスなどの不活性ガスが導入される。 A general method for producing a cured product of an unsaturated polyester resin from the above raw materials is a polycondensation reaction step of unsaturated polyester accompanied by dehydration, and after dissolving this in an unsaturated vinyl monomer, various additives are added thereto. It consists of a step of adjusting the characteristics. As various conditions during the synthesis, the temperature is often cured in the range of room temperature to 250 ° C., and an inert gas such as nitrogen gas is introduced into the reaction system under an arbitrary pressure.
樹脂硬化物は必ずしも完全に硬化している必要性はなく、常温では流動しない程度に半硬化させたものでもよい。この例としては、不飽和ポリエステル樹脂を用いた成形材料がある。 The cured resin is not necessarily completely cured, and may be semi-cured to such an extent that it does not flow at room temperature. An example of this is a molding material using an unsaturated polyester resin.
本発明の方法は、不飽和ポリエステル樹脂硬化物及び充填材を含有してなる複合材料にも適用できる。充填材としては、炭酸カルシウム、炭酸マグネシウムなどの炭酸塩；硫酸カルシウム、硫酸バリウム、亜硫酸カルシウムなどの（亜）硫酸塩；クレー、マイカ、ガラスバルーン、モンモリロナイト、ケイ酸、カオリン、タルクなどのケイ酸塩類；シリカ、珪藻土、酸化鉄、軽石バルーン、酸化チタン、アルミナのような酸化物；水酸化アルミニウム、水酸化マグネシウムのような水酸化物；グラファィト、ガラス繊維、炭素繊維、アスベスト繊維などの無機充填材；木粉、もみがら、木綿、紙細片、ナイロン繊維、ポリエチレン繊維、木材、パルプ、セルロースなどの有機充填材などが用いられる。上記充填材の含有量は、用途に応じて適宜選択され、通常は不飽和ポリエステル樹脂硬化物１００重量部当たり、０〜４００重量部である。 The method of the present invention can also be applied to a composite material containing a cured unsaturated polyester resin and a filler. As fillers, carbonates such as calcium carbonate and magnesium carbonate; (sulfur) sulfates such as calcium sulfate, barium sulfate and calcium sulfite; silicic acids such as clay, mica, glass balloon, montmorillonite, silicic acid, kaolin and talc Salts: Silica, diatomaceous earth, iron oxide, pumice balloon, oxides such as titanium oxide, alumina; hydroxides such as aluminum hydroxide and magnesium hydroxide; inorganic fillers such as graphite, glass fiber, carbon fiber, asbestos fiber Materials: Organic fillers such as wood powder, rice husk, cotton, paper strip, nylon fiber, polyethylene fiber, wood, pulp, cellulose, etc. are used. Content of the said filler is suitably selected according to a use, and is 0-400 weight part normally per 100 weight part of unsaturated polyester resin hardened | cured material.
本発明では、不飽和ポリエステル樹脂を処理液を用いて分解または溶解する。この処理液は、リン酸類及び有機溶媒が含まれていることが必要である。 In the present invention, the unsaturated polyester resin is decomposed or dissolved using a treatment liquid. This treatment liquid needs to contain phosphoric acids and an organic solvent.
本発明で使用するリン酸類としては、例えば、リン酸、次リン酸、亜リン酸、次亜リン酸、ピロリン酸、トリメタリン酸、テトラメタリン酸、ピロ亜リン酸などのリン酸系化合物があげられる。これら、リン酸類は、リン酸類の塩であってもよく、例えば、前記リン酸系化合物とリチウム、ナトリウム、カリウム、ルビジウム、セシウム、ベリリウム、マグネシウム、カルシウム、ストロンチウム、バリウム、チタン、ジルコニウム、バナジウム、クロム、マンガン、鉄、コバルト、ニッケル、銅、銀、パラジウム、亜鉛、アルミニウム、ガリウム、錫、アンモニウムなどの金属または陽イオンとの塩が挙げられる。これらリン酸類の塩は、１個の金属と２個の水素を有する第一塩、２個の金属と１個の水素を有する第二塩、３個の金属を有する第三塩のいずれでもよく、酸性塩、アルカリ性塩、中性塩のいずれでもよい。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、これらの化合物以外に、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。 Examples of phosphoric acids used in the present invention include phosphoric acid compounds such as phosphoric acid, hypophosphoric acid, phosphorous acid, hypophosphorous acid, pyrophosphoric acid, trimetaphosphoric acid, tetrametaphosphoric acid, and pyrophosphorous acid. It is done. These phosphoric acids may be salts of phosphoric acids. For example, the phosphoric acid compounds and lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, titanium, zirconium, vanadium, Examples thereof include salts with metals or cations such as chromium, manganese, iron, cobalt, nickel, copper, silver, palladium, zinc, aluminum, gallium, tin, and ammonium. These phosphoric acid salts may be any one of a first salt having one metal and two hydrogens, a second salt having two metals and one hydrogen, and a third salt having three metals. , Any of acidic salt, alkaline salt and neutral salt may be used. These compounds may be used alone or in combination of several kinds. In addition to these compounds, any compounds may be used in combination, and impurities may be contained.
上記リン酸類の中で、処理液への溶解性を考慮すれば、リン酸類のアルカリ金属塩が好ましく、リン酸類のカリウム塩が特に好ましい。また、水溶性の溶媒を使用する場合には、それらの水和物がさらに好ましく、リン酸カリウム水和物が特に好適である。 Among the phosphoric acids, in view of solubility in the treatment liquid, alkali metal salts of phosphoric acids are preferable, and potassium salts of phosphoric acids are particularly preferable. Moreover, when using a water-soluble solvent, those hydrates are more preferable, and potassium phosphate hydrate is especially suitable.
本発明で使用す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、エステル系などの有機溶媒があげられ、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、これらの有機溶媒は無機系溶媒と併用してもよく、また、不純物が含まれていてもかまわない。 Examples of the organic solvent used in the present invention include amide-based, alcohol-based, ketone-based, ether-based and ester-based organic solvents. These may be used alone or in combination. May be. These organic solvents may be used in combination with an inorganic solvent or may contain impurities.
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あげられる。 Examples of amide solvents 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.
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、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、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、ベンジルアルコール、ｔｅｒｔ−ブチルベンジルアルコール、メチルベンジルアルコール、クロロベンジルアルコール及びこれらの異性体など、さらには、ポリエチレングリコール＃２００、ポリエチレングリコール＃３００、ポリエチレングリコール＃４００（いずれも関東化学株式会社製商品名）等に例示されるポリエチレングリコールなどがあげられる。ポリエチレングリコールを用いる場合は、ポリエチレングリコールの平均分子量が５００以下であることが溶解率の観点から好ましい。 Examples of alcohol solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, iso-butanol, tert-butanol, 1-pentanol, 2-pentanol, and 3-pentanol. 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, 1,2- Propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, glycerin, dipropylene glycol , Ethylene glycol, ethylene glycol monomethyl ether, ethylene 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, tetra Tylene glycol, benzyl alcohol, tert-butylbenzyl alcohol, methylbenzyl alcohol, chlorobenzyl alcohol and isomers thereof, polyethylene glycol # 200, polyethylene glycol # 300, polyethylene glycol # 400 (all of which are Kanto Chemical Co., Inc.) And polyethylene glycol exemplified in the trade name). When polyethylene glycol is used, the average molecular weight of polyethylene glycol is preferably 500 or less from the viewpoint of solubility.
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、イソホロン等などがあげられる。 Examples of ketone solvents include acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, methyl isobutyl ketone, 2-heptanone, 4-heptanone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, phorone, and isophorone. can give.
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などがあげられる。 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, and the like. .
エステル系溶媒としては、例えば、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、メトキシブチルアセテート、メチルペンチルアセテート、エチルブチルアセテート、エチルヘキシルアセテート、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、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、エチレングリコールモノアセテート、ジエチレングリコールモノアセテート、エチレングリコールジアセテート、ジエチレングリコールジアセテートなどが挙げられる。 Examples of ester solvents include 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, methoxybutyl acetate Methylpentyl acetate, ethyl butyl acetate, ethyl hexyl acetate, cyclohexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, butyl propionate, isopentyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, Examples include γ-butyrolactone, ethylene glycol monoacetate, diethylene glycol monoacetate, ethylene glycol diacetate, and diethylene glycol diacetate. It is.
上記有機溶媒のなかでも、リン酸類との親和性の点でアルコール系溶媒が好ましい。中でも、１−ヘキサノール、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、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、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、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、ベンジルアルコール、ｔｅｒｔ−ブチルベンジルアルコール、メチルベンジルアルコール、クロロベンジルアルコール及びこれらの異性体など、ポリエチレングリコール＃２００、ポリエチレングリコール＃３００、ポリエチレングリコール＃４００がより好ましく、１−ヘプタノール、４−メチルシクロヘキサノール、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、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、エチレングリコール、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、ベンジルアルコール、ｔｅｒｔ−ブチルベンジルアルコール、メチルベンジルアルコール、クロロベンジルアルコール及びこれらの異性体など、ポリエチレングリコール＃２００、ポリエチレングリコール＃３００、ポリエチレングリコール＃４００が特に好ましい。 Among the above organic solvents, alcohol solvents are preferable from the viewpoint of affinity with phosphoric acids. Among them, 1-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, cyclohexanol, 1-methylcyclohexanol, 2-methylcyclohexanol, 3-methylcyclohexanol, 4-methylcyclohexanol, 1,2-propane Diol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, glycerin, dipropylene glycol, ethylene glycol, ethylene glycol monomethyl ether , Ethylene glycol monobutyl ether, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, trie Renglycol monomethyl ether, triethylene glycol monoethyl ether, tetraethylene glycol, benzyl alcohol, tert-butylbenzyl alcohol, methylbenzyl alcohol, chlorobenzyl alcohol and isomers thereof, polyethylene glycol # 200, polyethylene glycol # 300, polyethylene Glycol # 400 is more preferred, 1-heptanol, 4-methylcyclohexanol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butane Diol, 1,5-pentanediol, glycerin, dipropylene glycol, ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol, diethylene glycol Monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, tetraethylene glycol, benzyl alcohol, tert-butylbenzyl alcohol, methylbenzyl alcohol, chlorobenzyl alcohol Among these isomers, polyethylene glycol # 200, polyethylene glycol # 300, and polyethylene glycol # 400 are particularly preferable.
また、常圧または減圧の状態で分解または溶解処理を行う場合には、沸点が１５０℃以上の有機溶媒を用いることが好ましく、沸点が１７０℃以上の有機溶媒を用いることがより好ましい。 Further, when the decomposition or dissolution treatment is performed under normal pressure or reduced pressure, an organic solvent having a boiling point of 150 ° C. or higher is preferably used, and an organic solvent having a boiling point of 170 ° C. or higher is more preferably used.
さらに上記有機溶媒と併用してもよい無機溶媒としては、水、液体アンモニア、液体二酸化炭素などが例示される。 Furthermore, examples of the inorganic solvent that may be used in combination with the organic solvent include water, liquid ammonia, and liquid carbon dioxide.
本発明で使用する処理液は、有機溶媒に対し、リン酸類が０．００１〜８０重量％の範囲の任意の濃度になるよう調整することが好ましい。０．００１重量％未満では樹脂硬化物の分解または溶解速度が遅くなり処理効率に劣る傾向があり、８０重量％を越えると処理液を調整することが困難である。前記濃度範囲の中で、特に好ましいのは、０．１〜２０重量％である。 The treatment liquid used in the present invention is preferably adjusted so that phosphoric acids have an arbitrary concentration in the range of 0.001 to 80% by weight with respect to the organic solvent. If it is less than 0.001% by weight, the decomposition or dissolution rate of the cured resin tends to be slow and the processing efficiency tends to be inferior. If it exceeds 80% by weight, it is difficult to adjust the treatment liquid. In the concentration range, 0.1 to 20% by weight is particularly preferable.
またリン酸類は、必ずしもすべてが処理液中に溶解している必要はなく、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、リン酸類が失活した場合にはそれを補うので有効である。 In addition, phosphates do not necessarily have to be completely dissolved in the processing solution, and even in saturated solutions in which not all are dissolved, the solute is in an equilibrium state, and if phosphates are deactivated, they are compensated So it is effective.
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、常圧で調整する場合には、作業効率や、操作性、液の取り扱い性などの観点から、使用する溶媒の凝固点以上、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、窒素、アルゴン、二酸化炭素等の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 is adjusted may be any temperature. However, when adjusting at normal pressure, the boiling point is higher than the freezing point of the solvent used from the viewpoint of work efficiency, operability, and liquid handling. The following is preferable. The atmosphere for adjusting the treatment liquid may be air or an inert gas such as nitrogen, argon, carbon dioxide, etc., and may be under normal pressure, reduced pressure, or increased pressure.
また、処理液には、界面活性剤等を添加して使用してもかまわない。 In addition, a surfactant or the like may be added to the treatment liquid.
不飽和ポリエステル樹脂硬化物または、充填材と不飽和ポリエステル樹脂硬化物を含有する複合材料を処理液で処理する際には、該樹脂硬化物または複合材料をそのままの大きさで処理してもよいが、処理しやすい適当な大きさに破砕してもよい。破砕は、衝撃式破砕機、せん断式破砕機、圧縮式破砕機（ロール式、コンベア式、スクリュー式）、スタンプミル、ボールミル、ロッドミルなどを用いて行われる。破砕片の大きさには制限はなく、どのような大きさでもよい。すなわち、特に微小に破砕する必要はなく、処理装置の規模に合わせて処理可能な大きさに調整されていればよい。特に充填材を分離・回収する場合は、充填材を分離・回収する際の効率や、回収した充填材を再利用する際の取り扱い性などに合わせて、破砕片の大きさを適宜調整することが好ましい。例えば、ガラス繊維など、細かく粉砕することによって再利用が難しくなる充填材を回収する場合には、破砕片を１０ミリメートル以上とすることが好ましい。装置の規模や処理工程、処理時間を考慮すると、処理に供する不飽和ポリエステル樹脂硬化物または複合材料、その破砕片の最大径は、１０ミリメートル以上１．５メートル以下の範囲であることが好ましい。これよりも小さいと破砕の工程が長くなる傾向があり、これよりも大きいと処理時間が長くなる傾向がある。 When the unsaturated polyester resin cured product or the composite material containing the filler and the unsaturated polyester resin cured product is treated with the treatment liquid, the resin cured product or the composite material may be treated as it is. However, it may be crushed to an appropriate size for easy processing. The crushing is performed using an impact crusher, a shear crusher, a compression crusher (roll type, conveyor type, screw type), stamp mill, ball mill, rod mill or the like. There is no restriction | limiting in the magnitude | size of a fragment, Any size may be sufficient. In other words, it is not necessary to crush in particular, and it is only necessary to adjust the size so that it can be processed according to the scale of the processing apparatus. Especially when separating and recovering fillers, the size of the fragments should be adjusted appropriately according to the efficiency of separating and recovering the fillers and the handling characteristics when the recovered fillers are reused. Is preferred. For example, when recovering fillers that are difficult to reuse when finely pulverized, such as glass fibers, it is preferable that the crushed pieces be 10 mm or more. Considering the scale of the apparatus, processing steps, and processing time, it is preferable that the maximum diameter of the unsaturated polyester resin cured product or composite material to be subjected to the processing and the crushed pieces thereof is in the range of 10 millimeters to 1.5 meters. If it is smaller than this, the crushing process tends to be long, and if it is larger than this, the processing time tends to be long.
処理液を用いて樹脂硬化物または複合材料を分解または溶解処理する条件としては、処理液が液状であればよく、特に制限はない。好ましくは、処理速度を調整するために、処理液の凝固点以上、沸点以下の任意の温度が好ましい。また、樹脂の熱分解や充填材の強度低下などによる回収材の品質低下を防ぐためには、２５０℃以下の温度で溶解または分解処理することが好ましく、同様の理由から２１０℃以下の温度が特に好ましい。 Conditions for decomposing or dissolving the cured resin or composite material using the treatment liquid are not particularly limited as long as the treatment liquid is liquid. Preferably, any temperature between the freezing point and the boiling point of the treatment liquid is preferable in order to adjust the treatment speed. In addition, in order to prevent degradation of the quality of the recovered material due to thermal decomposition of the resin or decrease in strength of the filler, it is preferable to dissolve or decompose at a temperature of 250 ° C. or lower, and for the same reason, a temperature of 210 ° C. or lower is particularly preferable. preferable.
処理方法としては、処理液中に不飽和ポリエステル樹脂硬化物または複合材料を浸漬することによって行うことができる。 As a processing method, it can carry out by immersing unsaturated polyester resin hardened material or a composite material in a processing liquid.
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。安全性や作業の簡便性に優れる点で、常圧下に処理液を使用・保存することが好ましい。 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. It is preferable to use and store the treatment solution under normal pressure in terms of excellent safety and workability.
本発明では、不飽和ポリエステル樹脂硬化物または複合材料の分解または溶解処理を大気中、または、窒素、アルゴン、二酸化炭素などの不活性気体中で行うことができる。また、前記処理は、加圧下、減圧下、大気圧下のいずれでも行うことができる。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要としない点で、大気中で大気圧下に行うのが好ましい。 In the present invention, the unsaturated polyester resin cured product or composite material can be decomposed or dissolved in the atmosphere or in an inert gas such as nitrogen, argon, carbon dioxide, or the like. The treatment can be performed under pressure, under reduced pressure, or atmospheric pressure. It is preferable to carry out under atmospheric pressure in the atmosphere in that a specific gas atmosphere and a device for setting a specific atmospheric pressure are not required.
本発明においては、不飽和ポリエステル樹脂硬化物または複合材料を処理液で処理する際には、不飽和ポリエステル樹脂硬化物または複合材料に超音波振動を与える。超音波は人間の聴覚器官では捉えられない周波数の高い音波のことで、一般的に周波数は２０ｋＨｚ以上であり、診断装置や洗浄器等に用いられている。本発明で使用する超音波の周波数は、２０ｋＨｚ以上であればよく、好ましくは２０ｋＨｚ〜１ＭＨｚである。超音波振動を与える方法としては、超音波発振器を利用することが望まく、例えば、超音波振動を伝播するホーンの部分を、不飽和ポリエステル樹脂硬化物または複合材料が浸漬した処理液中に浸すことにより超音波振動を与えることができる。超音波振動を与える時間は、超音波の周波数や処理条件等により異なるため、処理対象物に応じて分解または溶解されるまでの時間が適宜選択される。 In the present invention, when the unsaturated polyester resin cured product or composite material is treated with the treatment liquid, ultrasonic vibration is applied to the unsaturated polyester resin cured product or composite material. Ultrasound is a high-frequency sound wave that cannot be captured by the human auditory organ, and generally has a frequency of 20 kHz or higher, and is used in diagnostic devices, washing machines, and the like. The frequency of the ultrasonic wave used in the present invention may be 20 kHz or more, and preferably 20 kHz to 1 MHz. As a method for applying ultrasonic vibration, it is desirable to use an ultrasonic oscillator. For example, a portion of a horn that propagates ultrasonic vibration is immersed in a treatment liquid in which an unsaturated polyester resin cured material or a composite material is immersed. Therefore, ultrasonic vibration can be applied. Since the time for applying ultrasonic vibration varies depending on the frequency of ultrasonic waves, processing conditions, and the like, the time until decomposition or dissolution is appropriately selected according to the object to be processed.
本発明によって不飽和ポリエステル樹脂硬化物を分解また溶解した樹脂成分は、一般的な方法で分離し、再利用することができる。例えば、不純物を沈殿法などで分離し、溶媒を蒸留などで分離して得られた樹脂成分を樹脂原料として再利用することができる。また、金属やガラスなどの固形の充填材を分離・回収する場合は、樹脂成分を処理液で分解または溶解したのち、濾過やデカンテーション等により回収することができる。 The resin component obtained by decomposing or dissolving the unsaturated polyester resin cured product according to the present invention can be separated and reused by a general method. For example, a resin component obtained by separating impurities by a precipitation method or the like and separating a solvent by distillation or the like can be reused as a resin raw material. In the case where a solid filler such as metal or glass is separated and recovered, the resin component can be recovered by filtration or decantation after being decomposed or dissolved in the treatment liquid.
以下に、本発明を実施例に基づいて説明する。 Hereinafter, the present invention will be described based on examples.
〔不飽和ポリエステル樹脂樹脂硬化物を含む複合材料の作製〕
温度計、攪拌機及び精留管を備えた２リットルの四つ口フラスコにプロピレングリコール５７８ｇ、ジエチレングリコール３１８ｇ、無水フタル酸４４４ｇ、無水マレイン酸６８６ｇを仕込み、窒素ガスを通しながら２１０ｇに４時間かけて昇温し、その温度で５時間反応させ、酸価８であることを確認して１６０℃まで冷却した。さらに、無水マレイン酸７８４ｇを仕込み、４時間かけて２１５℃に昇温した。その温度に保温して反応を進め、６時間で酸価２９の不飽和ポリエステル樹脂を得た。このようにして得られた不飽和ポリエステル樹脂６０重量部を、ハイドロキノン０．０２重量部を溶解したスチレンモノマー４０重量部に溶解して不飽和ポリエステル樹脂組成物を得た。
[Production of composite material containing cured resin of unsaturated polyester resin]
A 2-liter four-necked flask equipped with a thermometer, stirrer and rectifying tube was charged with 578 g of propylene glycol, 318 g of diethylene glycol, 444 g of phthalic anhydride, and 686 g of maleic anhydride. The mixture was warmed, reacted at that temperature for 5 hours, confirmed to have an acid value of 8, and cooled to 160 ° C. Further, 784 g of maleic anhydride was charged, and the temperature was raised to 215 ° C. over 4 hours. The reaction was carried out while keeping the temperature, and an unsaturated polyester resin having an acid value of 29 was obtained in 6 hours. An unsaturated polyester resin composition was obtained by dissolving 60 parts by weight of the unsaturated polyester resin thus obtained in 40 parts by weight of styrene monomer in which 0.02 part by weight of hydroquinone was dissolved.
〔不飽和ポリエステル樹脂樹脂硬化物を含む複合材料の処理〕
この不飽和ポリエステル樹脂組成物に炭酸カルシウムを加えて十分に混合し、ガラス繊維に塗布して１７０℃で１時間加熱硬化させ、不飽和ポリエステル樹脂樹脂硬化物４０重量％、炭酸カルシウム４０重量％及びガラス繊維２０重量％から構成される複合材料を作製し、これを用いて１０ｍｍ×３０ｍｍ×３ｍｍの試験片を作製した。
[Treatment of composite materials containing unsaturated polyester resin cured products]
Calcium carbonate is added to this unsaturated polyester resin composition and mixed well, applied to glass fiber, and cured by heating at 170 ° C. for 1 hour, 40% by weight of unsaturated polyester resin resin cured product, 40% by weight of calcium carbonate and A composite material composed of 20% by weight of glass fiber was produced, and a 10 mm × 30 mm × 3 mm test piece was produced using the composite material.
処理液は、表１に示す組成となるように、四つ口フラスコもしくは試験管に各成分を秤量し、室温で穏やかに撹拌して得た。処理に際しては、この処理液の入ったフラスコに温度計、コンデンサ、窒素導入口、超音波発生装置から超音波振動を伝播するホーンを取り付けた。窒素気流中で穏やかに攪拌しながら、オイルバスを使用して１９０〜２１０℃の範囲に加温した。試験管の場合は、超音波洗浄器に試験管を浸漬した。 The treatment liquid was obtained by weighing each component in a four-necked flask or test tube so as to have the composition shown in Table 1, and gently stirring at room temperature. During the treatment, a thermometer, a condenser, a nitrogen inlet, and a horn that propagates ultrasonic vibrations from an ultrasonic generator were attached to the flask containing the treatment liquid. While gently stirring in a nitrogen stream, the mixture was heated to a range of 190 to 210 ° C. using an oil bath. In the case of a test tube, the test tube was immersed in an ultrasonic cleaner.
試験片の質量を測定した後、処理液中に試験片を浸漬し、大気圧下、表１に示す温度で超音波振動を与えた。４時間後に試験片を取り出して再び質量を測定した。処理後の質量には、樹脂硬化物の分解により処理液中に沈降したガラス繊維と充填材の質量を加算し、処理前後の質量変化量を、試験片の樹脂分の質量で除し、樹脂硬化物の溶解率を算出した。本発明例１〜３、比較例１〜７を表１に示す。
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| JP2004164906A JP2005343999A (en) | 2004-06-02 | 2004-06-02 | Method for treating unsaturated polyester resin cured product and method for separating composite material |
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| JP2004164906A JP2005343999A (en) | 2004-06-02 | 2004-06-02 | Method for treating unsaturated polyester resin cured product and method for separating composite material |
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