JP7240567B2 - 再生補強繊維の製造方法 - Google Patents
再生補強繊維の製造方法 Download PDFInfo
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- JP7240567B2 JP7240567B2 JP2022567565A JP2022567565A JP7240567B2 JP 7240567 B2 JP7240567 B2 JP 7240567B2 JP 2022567565 A JP2022567565 A JP 2022567565A JP 2022567565 A JP2022567565 A JP 2022567565A JP 7240567 B2 JP7240567 B2 JP 7240567B2
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- resin
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- 239000012783 reinforcing fiber Substances 0.000 title claims description 54
- 238000004519 manufacturing process Methods 0.000 title claims description 26
- 229920005989 resin Polymers 0.000 claims description 207
- 239000011347 resin Substances 0.000 claims description 207
- 239000000463 material Substances 0.000 claims description 94
- 239000007788 liquid Substances 0.000 claims description 53
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 45
- 239000003929 acidic solution Substances 0.000 claims description 32
- 239000007800 oxidant agent Substances 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 22
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- 239000000835 fiber Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 15
- 229910017604 nitric acid Inorganic materials 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 6
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001749 primary amide group Chemical group 0.000 claims description 3
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- 239000004917 carbon fiber Substances 0.000 description 47
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- 239000002904 solvent Substances 0.000 description 34
- 238000000034 method Methods 0.000 description 32
- 238000010306 acid treatment Methods 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 20
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- 238000005406 washing Methods 0.000 description 13
- -1 hydrogen ions Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 239000003960 organic solvent Substances 0.000 description 9
- 235000011007 phosphoric acid Nutrition 0.000 description 9
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000005456 alcohol based solvent Substances 0.000 description 6
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
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- 239000005453 ketone based solvent Substances 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
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- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-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
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- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 229910052791 calcium Inorganic materials 0.000 description 2
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- 239000002131 composite material Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
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- OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 2
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- 238000004090 dissolution Methods 0.000 description 2
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- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
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- 239000003365 glass fiber Substances 0.000 description 2
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 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
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- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
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- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
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- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 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 compound 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
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 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
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
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- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
- C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
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- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/26—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing carboxylic acid groups, their anhydrides or esters
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- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
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- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/58—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides
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- D06M11/68—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
- D06M11/70—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with oxides of phosphorus; with hypophosphorous, phosphorous or phosphoric acids or their salts
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
- B29B17/02—Separating plastics from other materials
- B29B2017/0213—Specific separating techniques
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- D06M2101/40—Fibres of carbon
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- 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
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- Organic Chemistry (AREA)
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- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Description
そして、以上の知見に基づき、本発明者らはさらに検討を行い、本発明に至った。
(1) 樹脂と補強繊維とを含む繊維強化樹脂材料を酸を含む酸性溶液により処理する工程と、
前記繊維強化樹脂材料を酸化剤を含む処理液により処理し、前記繊維強化樹脂材料の前記樹脂の少なくとも一部を前記処理液に溶解させる工程と、を有し、
前記樹脂が、塩基性を有する化学構造を有する樹脂成分を含む、再生補強繊維の製造方法。
(2) 前記酸に含まれる成分のうち最もモル濃度の大きい成分のpKaが、5.0以下である、(1)に記載の再生補強繊維の製造方法。
(3) 前記酸は、硫酸、塩酸、リン酸および酢酸からなる群から選択される1種以上を含む、(1)または(2)に記載の再生補強繊維の製造方法。
(4) 前記酸性溶液中における前記酸の濃度が、0.5mol/L以上である、(1)~(3)のいずれか一項に記載の再生補強繊維の製造方法。
(5) 前記酸化剤は、酸化力を有する酸を含む、(1)~(4)のいずれか一項に記載の再生補強繊維の製造方法。
(6) 前記酸化力を有する酸は、硝酸、硫酸と硝酸との混酸、硝酸と塩酸との混酸(王水)および過酸化水素と硫酸との混合溶液からなる群から選択される1種以上を含む、(1)~(5)のいずれか一項に記載の再生補強繊維の製造方法。
(7) 前記塩基性を有する化学構造を有する樹脂成分は、主鎖構造に前記塩基性を有する化学構造を有する、(1)~(6)のいずれか一項に記載の再生補強繊維の製造方法。
(8) 前記塩基性を有する化学構造は、1、2または3級アミド結合である、(1)~(7)のいずれか一項に記載の再生補強繊維の製造方法。
まず、酸処理工程に先立ち、繊維強化樹脂材料を準備する。繊維強化樹脂材料は、補強繊維がマトリックス樹脂(単に「樹脂」ともいう)に埋設されることにより強化された樹脂材料である。このような、繊維強化樹脂材料としては、特に限定されず、例えば、炭素繊維強化プラスチック(Carbon Fiber Reinforced Plastics;CFRP)、ガラス繊維強化プラスチック(Glass Fiber Reinforced Plastics;GFRP)、ガラス長繊維マット強化熱可塑性プラスチック(Glass-Mat reinforced Thermoplastics;GMT)、アラミド繊維強化プラスチック(Aramid-Fiber-Reinforced Plastics;AFRP)、ケブラー繊維強化プラスチック(Kevlar Fiber Reinforced Plastics;KFRP)、ダイニーマ繊維強化プラスチック(Dyneema Fiber-Reinforced Plastics;DFRP)、バサルト繊維強化プラスチック、ボロン繊維強化プラスチック、およびこれらのプリプレグ等が挙げられる。上述した中でも、炭素繊維強化プラスチックは、使用量が比較的多く、また炭素繊維の製造時における消費エネルギー量が多大であるため、使用済みの炭素繊維強化プラスチックおよび/またはこのプリプレグ中の炭素繊維を回収し、再利用することが望ましい。
本工程においては、準備した繊維強化樹脂材料を酸を含む酸性溶液により処理する。このように、繊維強化樹脂材料を酸を含む酸性溶液により処理することにより、塩基性構造を有する樹脂成分に酸性溶液中の水素イオンを配位させて塩を形成させ、この結果、塩基性構造を有する樹脂成分ひいては樹脂自体が膨潤する。これにより、後述する酸化工程において酸化剤が樹脂に浸透しやすくなり、酸化工程における樹脂の分解・溶出が促進される。
脂肪族アルコール系としては、例えば、1-ブタノール、2-ブタノール、2-メチル-1-プロパノール、2-メチル-2-プロパノール、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、2-メチル-2-ブタノール、3-メチル-1-ブタノール、3-メチル-2-ブタノール、2,2-ジメチル-1-プロパノール、1-ヘキサノール、2-ヘキサノール、3-ヘキサノール、2-エチルヘキサノール、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、ドデカノール、メタノール、エタノール等の非環式脂肪族アルコールや、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等の脂環式アルコールが挙げられる。
グリコール系溶媒としては、例えば、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、ジプロピレングリコール等が挙げられる。
ハロゲン化芳香族炭化水素としては、例えば、オルトクロロフェノール、オルト時クロロベンゼン等が挙げられる。
ハロゲン化脂肪族炭化水素としては、例えば、クロロホルム、塩化メチレン等が挙げられる。
本工程においては、酸性溶液により膨潤した樹脂を含む繊維強化樹脂材料を酸化剤により処理して、繊維強化樹脂材料を酸化剤を含む処理液により処理し、繊維強化樹脂材料の樹脂の少なくとも一部を処理液に溶解させる。酸性溶液により膨潤した樹脂を含む繊維強化樹脂材料は、酸化剤が樹脂に浸透しやすくなり、この結果、本工程においては、酸化剤により樹脂が効率よく分解・溶出する。
次に、必要に応じて洗浄を行う。洗浄は、洗浄液を繊維強化樹脂材料と接触させることにより行うことができる。具体的には、上記の酸化工程において、処理液を洗浄液に置き換えることにより実施できる。ただし、洗浄時における洗浄液の温度や洗浄時間は、適宜設定できる。
以上のようにして繊維強化樹脂材料から樹脂成分を溶解、除去した状態で、繊維強化樹脂材料を乾燥してもよい。乾燥は、例えば、繊維強化樹脂材料を気体に接触させることより行うことができる。接触させる気体としては、特に限定されないが、安全面から、空気または窒素等の不活性ガスが好ましい。
(実施例1)
(i)準備工程
まず、試料としての炭素繊維強化樹脂材料を用意した。用いた炭素繊維樹脂材料は、長さ約30cm、幅5cm、厚さ約1mmのシートであった。また、炭素繊維強化樹脂材料を構成する樹脂は、アミン硬化エポキシ樹脂であった。
次に、炭素繊維強化樹脂材料を80℃に加熱しておいた40wt%(5.3mol/L)硫酸水溶液に1時間浸漬した。浸漬時において、硫酸水溶液の温度は80℃に維持した。
次に、炭素繊維強化樹脂材料を80℃に加熱しておいた40wt%(8.0mol/L)硝酸水溶液に60分間浸漬した。浸漬時において、硝酸水溶液の温度は80℃に維持した。
次に、反応生成物をN-メチル-2-ピロリドンで洗浄し、その後20質量%炭酸水素ナトリウム水溶液で中和し、その後炭素繊維強化樹脂材料中の炭素繊維を回収して、実施例1に係る再生炭素繊維を得た。
洗浄工程において反応生成物を10質量%水酸化ナトリウム水溶液(2.8mol/L)で中和および洗浄した以外は、実施例1と同様にして、実施例2に係る再生炭素繊維を得た。
酸化工程を以下のようにして行った以外は、実施例1と同様にして、実施例3に係る再生炭素繊維を得た。
酸化工程では、過酸化水素と硫酸との混合溶液による処理を行った。具体的には、酸処理工程後の炭素繊維強化樹脂材料を80℃に加熱しておいた95wt%(18.0mol/L)硫酸水溶液に15分浸漬し、その後、硫酸の体積換算で10%に当たる35wt%(11.6mol/L)過酸化水素水溶液を、炭素繊維強化樹脂材料を浸漬している硫酸水溶液に対し、5分かけて滴下した。
洗浄工程において反応生成物を10質量%水酸化ナトリウム水溶液(2.8mol/L)で中和および洗浄した以外は、実施例3と同様にして、実施例4に係る再生炭素繊維を得た。
酸処理工程において40wt%(5.3mol/L)硫酸水溶液に代えて35wt%(11.3mol/L)塩酸水溶液を用いた以外は、実施例3と同様にして、実施例5に係る再生炭素繊維を得た。
酸処理工程において40wt%(5.3mol/L)硫酸水溶液に代えて35wt%(11.3mol/L)塩酸水溶液を用いた以外は、実施例4と同様にして、実施例6に係る再生炭素繊維を得た。
酸処理工程において40wt%(5.3mol/L)硫酸水溶液に代えて40wt%(5.1mol/L)りん酸水溶液を用いた以外は、実施例3と同様にして、実施例5に係る再生炭素繊維を得た。
酸処理工程において40wt%(5.3mol/L)硫酸水溶液に代えて40wt%(5.1mol/L)りん酸水溶液を用いた以外は、実施例4と同様にして、実施例6に係る再生炭素繊維を得た。
酸処理工程を省略し、酸化工程における炭素繊維強化樹脂材料の硫酸水溶液への浸漬時間を120分間とした以外は、実施例1と同様にして、比較例1に係る再生炭素繊維を得た。
(比較例2)
酸処理工程を省略し、酸化工程における炭素繊維強化樹脂材料の硫酸水溶液への浸漬時間を120分間とした以外は、実施例2と同様にして、比較例2に係る再生炭素繊維を得た。
酸処理工程を省略した以外は、実施例3と同様にして、比較例3に係る再生炭素繊維を得た。
(比較例4)
酸処理工程を省略した以外は、実施例4と同様にして、比較例4に係る再生炭素繊維を得た。
得られた実施例1~8および比較例1~4にかかる再生炭素繊維について、熱重量分析(TGA)により残存樹脂量を算出した。具体的には、まず、300ml/minの流量で窒素を流しながら10℃/minの昇温速度で実施例1~8および比較例1~4にかかる再生炭素繊維を加熱し、200℃から800℃までの間の再生炭素繊維の重量の減少分を測定した。次に、熱重量分析における炭素繊維自体の重量減少を考慮し、同条件下での新品炭素繊維の重量減少がないことを予め測定で確認した。なお、上記の残存樹脂量の測定は、3回行い、その平均値を実施例1~8および比較例1~4にかかる再生炭素繊維の残存樹脂量とした。なお、未処理の炭素繊維補強樹脂材料中の樹脂量は、31.2重量%である。結果を実験条件とともに表1に示す。
Claims (7)
- 樹脂と補強繊維とを含む繊維強化樹脂材料を無機酸および水を含む酸性溶液により処理する第1の工程と、
前記第1の工程後に前記補強繊維を含む前記繊維強化樹脂材料を酸化剤を含む処理液により処理し、前記繊維強化樹脂材料の前記樹脂の少なくとも一部を前記処理液に溶解させる第2の工程と、を有し、
前記無機酸は、硫酸およびリン酸からなる群から選択される1種以上を含み、
前記樹脂が、塩基性を有する化学構造を有する樹脂成分を含む、再生補強繊維の製造方法。 - 前記無機酸に含まれる成分のうち最もモル濃度の大きい成分のpKaが、5.0以下である、請求項1に記載の再生補強繊維の製造方法。
- 前記酸性溶液中における前記無機酸の濃度が、0.5mol/L以上である、請求項1または2に記載の再生補強繊維の製造方法。
- 前記酸化剤は、酸化力を有する酸を含む、請求項1~3のいずれか一項に記載の再生補強繊維の製造方法。
- 前記酸化力を有する酸は、硝酸、硫酸と硝酸との混酸、硝酸と塩酸との混酸(王水)および過酸化水素と硫酸との混合溶液からなる群から選択される1種以上を含む、請求項4に記載の再生補強繊維の製造方法。
- 前記塩基性を有する化学構造を有する樹脂成分は、主鎖構造に前記塩基性を有する化学構造を有する、請求項1~5のいずれか一項に記載の再生補強繊維の製造方法。
- 前記塩基性を有する化学構造は、1、2または3級アミド結合である、請求項1~6のいずれか一項に記載の再生補強繊維の製造方法。
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