CN1769324A - Method for dissolving saturated polyester - Google Patents
Method for dissolving saturated polyester Download PDFInfo
- Publication number
- CN1769324A CN1769324A CNA2005101170871A CN200510117087A CN1769324A CN 1769324 A CN1769324 A CN 1769324A CN A2005101170871 A CNA2005101170871 A CN A2005101170871A CN 200510117087 A CN200510117087 A CN 200510117087A CN 1769324 A CN1769324 A CN 1769324A
- Authority
- CN
- China
- Prior art keywords
- saturated polyester
- solvent
- solution
- alcohol
- meoh
- 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
- 229920000728 polyester Polymers 0.000 title claims abstract description 90
- 229920006395 saturated elastomer Polymers 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 65
- 239000002904 solvent Substances 0.000 claims description 93
- -1 poly terephthalic acid alkane diol ester Chemical class 0.000 claims description 31
- 150000001408 amides Chemical class 0.000 claims description 29
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 238000004064 recycling Methods 0.000 abstract description 6
- 239000000835 fiber Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 151
- 239000000243 solution Substances 0.000 description 63
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 44
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 37
- 150000003839 salts Chemical class 0.000 description 37
- 238000000354 decomposition reaction Methods 0.000 description 33
- 230000000052 comparative effect Effects 0.000 description 24
- 239000003513 alkali Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229920000139 polyethylene terephthalate Polymers 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
- ZEABYRLMGDTEAI-UHFFFAOYSA-M lithium;methanol;hydroxide Chemical compound [Li+].[OH-].OC ZEABYRLMGDTEAI-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 3
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002500 ions Chemical group 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 3
- 235000019798 tripotassium phosphate Nutrition 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical class CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-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
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 239000004593 Epoxy Substances 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-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
- 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 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
- 230000004927 fusion Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-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
- 239000012535 impurity Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 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
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006140 methanolysis reaction Methods 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
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- 239000004408 titanium dioxide Substances 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for dissolving a saturated polyester which can be employed for recycling a saturated polyester being used as a fiber, a film, a bottle or the like with ease and also at a low cost a solution for use in decomposing a saturated polyester and a method for decomposing a saturated polyester using the solution.
Description
Technical field
The present invention relates to saturated polyester dissolving method, decomposing saturated polyester solution and use its decomposition method.More particularly, it relates to by dissolving or decomposing saturated polyester, can carry out dissolving method, the solution of decomposing saturated polyester and the decomposition method that uses it of saturated polyester of the recycling of monomer whose or prepolymer.
Background technology
With poly terephthalic acid alkane diol ester is the saturated polyester of representative, because excellents such as intensity, the transparency, thermotolerance, resistance are used to various purposes such as fiber, film, bottle.
But, in recent years, be accompanied by the increase of usage quantity, the recovery of a large amount of saturated polyesters that use that produce, the recovery of the saturated polyester of the product off quality that perhaps produce in manufacture course of products from global environment, becomes big problem.Now, as the recovery method of saturated polyester, roughly be divided into salvage material method, recovery of heat method and chemical recycling.
As the salvage material method, behind the known fusion saturated polyester and the method utilized again of initial feed blended and only use recovery article to make the method etc. of inferior quality goods.But by the recovery article that the salvage material method obtains, because of its intensity is low, as described above, needs and initial feed are used together.In addition, if in saturated polyester mixed plastic owing to exist the intensity of recovery article significantly to reduce or paintedly take off most problem, therefore, before fusion, need only to the strict classification of saturated polyester.
In addition, recovery of heat method is that the hotwork that will generate when burning the saturated polyester that reclaims is the method that fuel utilizes again.But, owing to make the saturated polyester burning, thus realize reclaiming, and, produce carbonic acid gas during owing to burning, aspect environment, also have problems.
In addition, chemical recycling is obsolete saturated polyester goods to be turned back to its raw material, the method for resynthesis.Original purpose is to make the utilization again of resource become possibility, and, easily contaminated solution, sneak into other resins, when being shaped molecular weight reduce, because of the problem such as painted that heat causes, therefore be considered to best absorption method.As this chemical recycling, can enumerate: (1) changes saturated polyester and strong acid or alkaline aqueous solution heat treated together into hydrolysis method that dicarboxylic acid phthalic acid such as terephthalic acid or its salt reclaim; (2) with saturated polyester and methyl alcohol heat treated together, change the methanolysis method that dimethyl dicarboxylate such as dimethyl terephthalate (DMT) reclaim into; Perhaps (3) make its depolymerization with heat treated such as the glycol of saturated polyester and ethylene glycol or propylene glycol etc. together, reclaim the glycol decomposition method etc. of the prepolymer of saturated polyester.As its object lesson, can enumerate with sodium hydroxide is the method that the spy of catalyzer opens flat 11-302208 communique record, the spy that glycol decomposes the back methanolysis opens the method for flat 11-322677 communique record, the spy who reclaims polyethylene terephthalate opens 2000-53802 communique and the special method of opening the record of 2000-169623 communique, with titanium compound or tin compound is the method that the spy of catalyzer opens the record of 2000-191766 communique, the spy of the plastics of classification beyond the polyethylene terephthalate opens the method for 2000-198876 communique record, perhaps is the spy of the catalyzer method of opening the record of 2000-302707 communique etc. with the ferric oxide.
But the chemical recycling of these known saturated polyesters in order to carry out transesterification reaction, must carry out heat about 200 ℃, and therefore, the problem of existence is, and is unsatisfactory from the energy expenditure angle.In addition, when using low-molecular-weight alcohol to carry out transesterification reaction,, usually under high pressure react, have the such problem of high pressure vessel that to use high price in order to prevent its evaporation.
Summary of the invention
Use the solution under low temperature, normal pressure, also can dissolve saturated polyester even the purpose of this invention is to provide, can be easily and economically with the dissolving method of the saturated polyester of its recovery.
Even another object of the present invention provides the ester bond that also can optionally disconnect saturated polyester under low temperature, normal pressure, generate the solution of the stable compound of the raw material that constitutes saturated polyester.
Another purpose of the present invention provides the solution that uses above-mentioned decomposing saturated polyester, can be easily and economically with the decomposition method of the saturated polyester of its recovery.
That is, the present invention relates to the dissolving method of saturated polyester, it is characterized in that using acid amides series solvent dissolving saturated polyester.
For dissolving method of the present invention, effective especially when saturated polyester is poly terephthalic acid alkane diol ester.In addition, the acid amides series solvent, preferably at room temperature be liquid and its boiling point more than or equal to 180 ℃, preferred especially N-Methyl pyrrolidone.In addition, preferably under normal pressure, dissolve, as the temperature of the acid amides series solvent in when dissolving, be preferably greater than and equal zero pour, particularly preferably in 130 ℃～190 ℃ smaller or equal to boiling point.
In addition, the present invention relates to solution, it is the solution of decomposing saturated polyester, it is characterized in that containing alkali and as the monohydroxy-alcohol of solvent, perhaps contains phosphoric salt and as the monohydroxy-alcohol of solvent.
With regard to regard to solution decomposing saturated polyester of the present invention, effective especially for poly terephthalic acid alkane diol ester.In addition, monohydroxy-alcohol, preferred lower alcohol, special particular methanol.
Solution of the present invention is being to contain alkali and during as the solution of the monohydroxy-alcohol of solvent for feature, does not preferably contain the solvent beyond the monohydroxy-alcohol.
Solution of the present invention, be to contain phosphoric salt and during for feature as the solution of the monohydroxy-alcohol of solvent, preferred also containing is selected from least a by in the group of acid amides series solvent, ketone series solvent, ether series solvent, ester series solvent, hydrocarbon system solvent composition, as the solvent beyond the monohydroxy-alcohol.And, preferred its hydrate of phosphoric salt, more preferably basic metal phosphoric salt, preferably phosphoric acid potassium especially.
In addition, the present invention relates to the decomposition method of saturated polyester, it is characterized in that, use above-mentioned alkali and the monohydroxy-alcohol of containing, perhaps the solution of phosphoric salt and monohydroxy-alcohol decomposes saturated polyester.
For decomposition method of the present invention, effective especially when saturated polyester is poly terephthalic acid alkane diol ester.In addition, the present invention preferably decomposes under normal pressure, the solution temperature when decomposing, preferably more than or equal to its zero pour smaller or equal to boiling point, especially preferably smaller or equal to 150 ℃.
In addition, the degradation production of the saturated polyester that obtains by decomposition method of the present invention is at least a to be dicarboxylic acid dialkyl esters or glycol, and this degradation production can be obtained by a step chemical reaction.
The application is that the basis requires preference with following application: come from the previous Japanese patent application of same applicant, promptly, 2001-351068 number (the November 16 calendar year 2001 applying date), 2001-351073 number (the November 16 calendar year 2001 applying date), 2001-351076 (the November 16 calendar year 2001 applying date), 2001-351081 (the November 16 calendar year 2001 applying date), and 2001-351082 (the November 16 calendar year 2001 applying date).In order to introduce these applications herein with reference to these specification sheetss.
Embodiment
The saturated polyester that uses in dissolving method of the present invention, solution and decomposition method is the polymkeric substance that dicarboxylic acid or dicarboxylic ester and glycol polymerization are obtained.
As dicarboxylic acid, for example can enumerate terephthalic acid, Tetra hydro Phthalic anhydride, m-phthalic acid, hexanodioic acid, naphthalene dicarboxylic acids, chlorendic acid, tetrabromophthalic anhydride, tetrahydronaphthalic anhydride, tetrachlorophthalic tetrachlorophthalic anhydrid, succsinic acid, normal pyrotartaric acid, trihemellitic acid acid anhydride, cyclopentadiene-maleic anhydride adduct etc.
As dicarboxylic ester, for example can enumerate dialkyls such as the dimethyl esters of above-mentioned dicarboxylic acid, diethyl ester, dipropyl, dibutyl ester.
As glycol, for example can enumerate, ethylene glycol, 1, the 4-butyleneglycol, 1, the 4-cyclohexanediol, propylene glycol, glycol ether, neopentyl glycol, dipropylene glycol, dibromoneopentyl glycol, 3 third glycol, triglycol, poly-alkyl diol, cyclohexanediol, the tri-methyl-amyl glycol, the dihydroxyl Dicyclopentadiene (DCPD), dihydroxyphenyl propane, tetrabromo-bisphenol, the dialkoxy dihydroxyphenyl propane, the dialkoxy tetrabromo-bisphenol, quinhydrones, Resorcinol, catechol, the dihydroxyphenyl propane that belongs to many ring two functional group's phenol, Bisphenol F, bis-phenol, the dihydroxyl diphenyl, dihydroxyl biphenol, and their halogenide, the alkyl substituent, isomers etc.
Saturated polyester of the present invention can make up multiple above-mentioned dicarboxylic acid, dicarboxylic ester and glycol respectively and obtains, and also can use catalyzer to obtain as required.In addition, saturated polyester of the present invention can contain the mineral-type filler of glass fibre, glass powder, lime carbonate, aluminium hydroxide, magnesium hydroxide, Calucium Silicate powder, mica, clay, titanium dioxide, aluminum oxide, ferric oxide, aluminium etc.
In the saturated polyester that constitutes by above composition, be poly terephthalic acid alkane diol esters such as polyethylene terephthalate, polybutylene terephthalate as the saturated polyester that can dissolve especially effectively or decompose by dissolving of the present invention or decomposition reaction.
Below, the dissolving method as above-mentioned saturated polyester is described.
Dissolving method of the present invention is to use the acid amides series solvent to make the saturated polyester dissolving.Acid amides series solvent as can use herein is not particularly limited.For example can enumerate, methane amide, N-methylformamide, N, dinethylformamide, N, N-diethylformamide, ethanamide, N-methylacetamide, N, N-N,N-DIMETHYLACETAMIDE, N, N, N ', N '-4-methyl urea, 2-Pyrrolidone, N-N-methyl-2-2-pyrrolidone N-, hexanolactam, carbamate etc.These solvents can use separately, also can any mixing use.But in these acid amides series solvents, in order to implement solubilizing reaction of the present invention especially effectively, preferably at room temperature be liquid and boiling point more than or equal to 180 ℃ solvent, preferred especially N-Methyl pyrrolidone.In addition, the usage quantity of acid amides series solvent with respect to saturated polyester 1 weight part, is preferably 0.5～100 weight part, more preferably 1～10 weight part in the present invention.
In addition, so long as not with the solvent of saturated polyester and acid amides series solvent reaction, just can mix arbitrary this class other solvents in addition.As other such solvents, for example can enumerate ketone series solvent, ether series solvent, hydrocarbon system solvent or water etc.
Example as the ketone series solvent, for example can enumerate acetone, ethyl methyl ketone, 2 pentanone, propione, methyl-n-butyl ketone, methyl isopropyl ketone, 2-heptanone, dipropyl ketone, diisopropyl ketone, pimelinketone, methylcyclohexanone, methyl phenyl ketone, sym.-diisopropylideneacetone, isophorone etc.
As the ether series solvent, for example can enumerate dipropyl ether, two different basic ethers, dibutyl ether, two hexyl ethers, phenylmethylether, phenyl ethyl ether, diox, tetrahydrofuran (THF), acetal, glycol dimethyl ether, ethylene glycol diethyl ether, diglyme, diethyl carbitol etc.
As the hydrocarbon system solvent, for example can enumerate hexane, heptane, octane, nonane, decane, toluene, dimethylbenzene, ethylbenzene, diethylbenzene, and their isomers, halogenide and mixture etc.
In dissolving method of the present invention, these other solvents can use a kind of, also can mix multiple use with arbitrary proportion.
As the method by dissolving method of the present invention dissolving saturated polyester, at first, it is ground into suitable size is preferred in order easily saturated polyester to be carried out disaggregating treatment.Can use that for example impact grinder, shear-type pulverizer, compression pulverizer, stamp mill, ball mill, clavate pulverizer etc. are pulverized.Size to fragment is not particularly limited, but when considering the scale of device, preferably in 0.1 cubic centimetre to 1 cubic metre scope.During less than 0.1 cubic centimetre, the pulverizing time can be longer, and during greater than 1 cubic metre, the treatment time again can be longer, and the processing efficiency under the both of these case all can significantly reduce.
Saturated polyester dissolved method by the acid amides series solvent will have been pulverized is not particularly limited.For example can enumerate, the saturated polyester pulverized is immersed method in the acid amides series solvent, the acid amides series solvent is sprayed to method on the saturated polyester of having pulverized etc.
Be not particularly limited as temperature with acid amides series solvent dissolution process saturated polyester, as long as this solution is that liquid state is not particularly limited, based on the decomposition rate that is easy to regulate expectation and processing etc., in the temperature range of zero pour smaller or equal to boiling point more than or equal to solution, select arbitrarily, preferably 130～190 ℃ of scopes.In addition, the atmosphere during dissolution process can be in atmosphere, also can be in the rare gas element of nitrogen, argon, carbonic acid gas etc., under normal pressure, under the decompression or add depress any situation can, consider from security and simplification angle, preferably under normal pressure.When improving dissolution rate, except that heating up, pressurizeing, it also is effective stirring solvent or use ultrasonic wave to produce vibration in steeping process.
In addition, when dissolution process, can sneak into saturated polyester plastics in addition, as polyethylene, polypropylene, polyvinyl chloride, polymeric amide, acrylic resin, polystyrene, ABS resin, polyurethane(s), polyhutadiene, acetal, silicone resin, poly-methyl methacrylate base ester, urea resin, phenol resins, Resins, epoxy, polyimide etc.Even, therefore, can after processing, easily separate because the heat fusing of these polymkeric substance during because of dissolution process can not mix with the acid amides series solvent yet.
In addition, can sneak into metal and their alloy or their oxide compound etc. of aluminium, iron, zinc, tin, nickel, chromium, silicon etc.And, also can sneak into the inorganics of glass, sand, aluminum oxide, porcelain, pottery etc. etc.These metals, metal oxide, inorganics be not because of decomposing in the acid amides series solvent, so can easily separate after processing.
The solvent soln of the saturated polyester that obtains by above-mentioned dissolution process, remove desolvate after, can utilize again by the heating and melting moulding.
Below, solution that decomposes aforementioned saturated polyester and the decomposition method that uses it are described.
The solution of decomposing saturated polyester of the present invention contains alkali and monohydroxy-alcohol, and perhaps phosphoric salt and monohydroxy-alcohol are as the constituent of necessity.
Alkali as using in solution of the present invention is not particularly limited.Alkali-metal oxyhydroxide such as lithium, sodium, potassium, caesium are for example arranged, alkoxide, hydride etc.These compounds can use separately, also can mix multiple use.And, also have no relations even contain impurity.
Phosphoric salt as using in solution of the present invention is not particularly limited.For example, salt that metal such as phosphoric acid, diphosphanetetroic acid, phosphorous acid, the phosphoric acid class that connects diphosphorous acid, tetra-sodium, three metaphosphoric acids, four metaphosphoric acids, pyrophosphorous acid etc. and lithium, sodium, potassium, rubidium, caesium, beryllium, magnesium, calcium, strontium, barium, titanium, zirconium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminium, tin, ammonium or positively charged ion form etc. is arranged.The trivalent salt that these salt can be monovalent salt, the divalent salts with 2 atoms metals and 1 hydrogen atom with 1 atoms metal and 2 hydrogen atoms, have 3 atoms metals any; Can be acid-salt, basic salt, neutral salt; It also can be hydrate.These compounds can use separately, also can mix multiple use.In addition, also have no relations even contain impurity.In these phosphoric salts, for implementing decomposition reaction of the present invention especially effectively, preferred as alkali phosphoric salt, special preferably phosphoric acid potassium.In addition, the also hydrate of preferably phosphoric acid class salt.
Have as the example that in solution of the present invention, is used as the monohydroxy-alcohol of solvent, methyl alcohol, ethanol, the 1-propyl alcohol, the 2-propyl alcohol, the 1-butanols, the 2-butanols, isopropylcarbinol, the trimethyl carbinol, the 1-amylalcohol, the 2-amylalcohol, the 3-amylalcohol, 2-methyl-1-butene alcohol, primary isoamyl alcohol, tertiary amyl alcohol, 3-methyl-2-butanols, neopentyl alcohol, the 1-hexanol, 2-methyl-1-pentene alcohol, 4-methyl-2-amylalcohol, 2-ethyl-1-butanols, the 1-enanthol, the 2-enanthol, the 3-enanthol, hexalin, 1 methyl cyclohexanol, 2 methyl cyclohexanol, 3 methyl cyclohexanol, 4 methyl cyclohexanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, the diglycol monotertiary propyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triglycol list ether, phenylcarbinol, tert.-butylbenzene methyl alcohol, methylbenzyl alcohol, chlorinated benzene methyl alcohol, and their isomers.These monohydroxy-alcohols can use a kind of, also can mix multiple use with arbitrary proportion, also can contain water.In addition, in these monohydroxy-alcohols, in order to implement decomposition reaction of the present invention especially effectively, preferred lower alcohol, more preferably methyl alcohol.
In addition, for the solvent of solution of the present invention, when solution is alkali and monohydroxy-alcohol, preferably do not contain monohydroxy-alcohol solvent in addition.When solution is phosphoric salt and monohydroxy-alcohol, preferably also contain monohydroxy-alcohol solvent in addition, for example, acid amides series solvent, ketone series solvent, ether series solvent, ester series solvent, hydrocarbon system solvent etc.
As the acid amides series solvent, for example can enumerate, methane amide, N-methylformamide, N, dinethylformamide, N, N-diethylformamide, ethanamide, N-methylacetamide, N,N-dimethylacetamide, N, N, N ', N '-4-methyl urea, 2-Pyrrolidone, N-N-methyl-2-2-pyrrolidone N-, hexanolactam, carbamate etc.
Example as the ketone series solvent, for example can enumerate acetone, ethyl methyl ketone, 2 pentanone, propione, methyl-n-butyl ketone, methyl isopropyl ketone, 2-heptanone, dipropyl ketone, diisopropyl ketone, pimelinketone, methylcyclohexanone, methyl phenyl ketone, sym.-diisopropylideneacetone, isophorone etc.
As the ether series solvent, for example can enumerate dipropyl ether, diisopropyl ether, dibutyl ether, two hexyl ethers, phenylmethylether, phenyl ethyl ether, diox, tetrahydrofuran (THF), acetal, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diglyme, diethyl carbitol etc.
As the ester series solvent, for example can enumerate ethyl formate, propyl formate, butyl formate, tetryl formate, pentyl formate, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butylacetate, isobutyl acetate, pentyl acetate, Isoamyl Acetate FCC, methoxy butyl acetate, methyl amyl acetate, acetate ethyl butyl ester, the acetate ethylhexyl, hexalin acetate, phenylmethyl acetate, methyl propionate, ethyl propionate, butyl propionate, isoamyl propionate, the M-nitro benzoic acid methyl esters, ethyl benzoate, the M-nitro benzoic acid propyl ester, the M-nitro benzoic acid butyl ester, gamma-butyrolactone, ethylene glycol acetate, the diglycol monotertiary acetic ester, glycol diacetate, diethylene glycol diacetate etc.
As the hydrocarbon system solvent, for example can enumerate hexane, heptane, octane, nonane, decane, toluene, dimethylbenzene, ethylbenzene, diethylbenzene, and their isomers, halogenide and mixture etc.
Solvent beyond these monohydroxy-alcohols can use a kind of, also can mix multiple use with arbitrary proportion.
As the proportioning that contains the solution of alkali and monohydroxy-alcohol of the present invention, with respect to the solvent monohydroxy-alcohol, can be at preferred 0.1～90wt%, more preferably allotment alkali is any concentration in 1～80wt% scope.In addition, as the proportioning that contains the solution of phosphoric salt and monohydroxy-alcohol of the present invention, with respect to the solvent monohydroxy-alcohol, can be at preferred 0.1～90wt%, more preferably the allotment phosphoric salt is any concentration in 1～80wt% scope.Under the situation that except phosphoric salt and monohydroxy-alcohol, also contains monohydroxy-alcohol solvent in addition, can be with respect to the total amount of the solvent beyond monohydroxy-alcohol and the monohydroxy-alcohol, the concentration of allotment phosphoric salt is any concentration in identical concentration range.Under the situation of any solution, if less than 0.1wt%, the decomposition rate of saturated polyester is slow, when surpassing 90wt%, allocates this solution becomes and gets difficult.Alkali or phosphoric salt be all dissolvings not necessarily, and not in the saturated solution of CL, solute reaches equilibrium state at these, can replenish this solute when alkali or phosphoric salt inactivation, are effective.In addition, in solution of the present invention, can add additives such as interfacial agent.
Temperature when allocating solution of the present invention is not particularly limited, and is preferably greater than the fusing point of the solvent that equals to use, smaller or equal to boiling point.In addition, atmosphere can be in atmosphere, also can be in rare gas element, and can be under normal pressure, under the decompression or add and depress.
As method with solution decomposing saturated polyester of the present invention, at first, will be ground into as the saturated polyester of object can disaggregating treatment size be preferred.Can use that for example impact grinder, shear-type pulverizer, compression pulverizer, stamp mill, ball mill, clavate pulverizer etc. are pulverized.Size to fragment is not particularly limited, but when considering the scale of device, preferably in 0.1 cubic centimetre to 1 cubic metre scope.During less than 0.1 cubic centimetre, the pulverizing time can be longer, and during greater than 1 cubic metre, the treatment time again can be longer, and the processing efficiency under the both of these case all significantly reduces.
The method of decomposing for the saturated polyester that will pulverize with solution of the present invention is not particularly limited.For example, the saturated polyester of having pulverized is immersed method in the solution of the present invention, with solution spray of the present invention method to the saturated polyester of having pulverized etc.
Temperature for solution-treated disaggregating treatment saturated polyester of the present invention the time is not particularly limited, as long as this solution is liquid, based on decomposition rate that is easy to regulate expectation and processing etc., can select arbitrarily in smaller or equal to the temperature range of boiling point more than or equal to the zero pour of solution.Preferably under smaller or equal to 150 ℃ temperature, handle, more preferably under temperature, handle less than 100 ℃ of grades.In addition, the atmosphere during disaggregating treatment can be in atmosphere, also can be in the rare gas element of nitrogen, argon, carbonic acid gas etc., can be arbitrarily under normal pressure, under the decompression or add and depress, this is not limited.Consider from security and simplification angle, preferably under normal pressure, carry out.When improving decomposition rate, except that heating up, pressurizeing, it also is effective stirring solvent or use ultrasonic wave to produce vibration in steeping process.
In addition, when disaggregating treatment, can sneak into saturated polyester plastics in addition, as polyethylene, polypropylene, polyvinyl chloride, polymeric amide, acrylic resin, polystyrene, ABS resin, polyurethane(s), polyhutadiene, acetal, silicone resin, poly-methyl methacrylate base ester, urea resin, phenol resins, Resins, epoxy, polyimide etc.These polymkeric substance because at the solution that contains alkali and monohydroxy-alcohol, or contain in the solution of phosphoric salt and monohydroxy-alcohol and do not decompose, so can easily separate after processing.
Metal and their alloy or their oxide compound etc. that can add in addition, aluminium, iron, zinc, tin, nickel, chromium, silicon etc.And, also can add the inorganics of glass, sand, aluminum oxide, porcelain, pottery etc. etc.These metals, metal oxide, inorganics because of at the solution that contains alkali and monohydroxy-alcohol, or contain in the solution of phosphoric salt and monohydroxy-alcohol and do not decompose, so can easily separate after processing.
In the degradation production that obtains by disaggregating treatment of the present invention, contain dicarboxylic acid dialkyl esters or glycol at least, unqualified for product in addition.Dicarboxylic acid dialkyl esters becomes dicarboxylic acid by adding acid, separates out from the solution that is added with excessive water.By this dicarboxylic acid washing, drying are obtained highly purified dicarboxylic acid.Dicarboxylic acid can utilize as the synthesis material of saturated polyester again.
In addition, used once or above solution of the present invention, removed degradation production,,, therefore, no matter used how many times to use owing to saturated polyester can be decomposed by supplying phosphoric salt, alkali or monohydroxy-alcohol etc. by modes such as filtrations.
Like this, in the present invention, can obtain as above-mentioned degradation production by a step chemical reaction.
Below, describe the present invention in detail according to embodiment, but the present invention is not limited thereto.
Embodiment
(dissolution rate of saturated polyester)
As saturated polyester, the polyethylene terephthalate that commercially available 0.35mm is thick (プ ラ ス チ ッ Network Industrial Co., Ltd system trade(brand)name in サ Application ロ ィ De ペ ッ ト ェ one ス EPG100, the tube) plate cutting is made into the test film of 10mm * 30mm.Various acid amides series solvents with 10.0g drop into respectively in the glass test tube of 20ml capacity respectively, utilize oil bath that the temperature in each test tube is remained on 60 ℃.After surveying the quality of overtesting sheet, test film is immersed in each solvent, cover the aluminum lid for preventing solvent evaporation.After arriving specific time, take out test film, measure quality again after washing, the drying, according to the quality change before and after the dipping, the quality of calculating dissolved saturated polyester is as dissolution rate.
Use the embodiment 1～5 of various acid amides series solvents and use the various conditions and the dissolution rate of the comparative example 1～8 of amides all kinds of SOLVENTS in addition to be shown in table 1.
Table 1
| Solvent | Temperature (℃) | Time (h) | Dissolution rate (%) | |
| Embodiment 1 | N,N-dimethylacetamide | 160 | 4.0 | 14.4 |
| Embodiment 2 | N-Methyl pyrrolidone | 160 | 4.0 | 71.3 |
| Embodiment 3 | N, dinethylformamide | 140 | 4.0 | 5.8 |
| Embodiment 4 | N,N-dimethylacetamide | 140 | 4.0 | 3.6 |
| Embodiment 5 | N-Methyl pyrrolidone | 140 | 4.0 | 28.1 |
| Comparative example 1 | Isophorone | 160 | 4.0 | -3.2 |
| Comparative example 2 | Methyl phenyl ketone | 160 | 4.0 | -0.7 |
| Comparative example 3 | Diethylene glycol monomethyl ether | 160 | 4.0 | 0 |
| Comparative example 4 | Diethylene glycol diacetate | 160 | 4.0 | -0.7 |
| Comparative example 5 | The diethylene glycol monobutyl ether acetic ester | 160 | 4.0 | -1.3 |
| Comparative example 6 | Benzyl Benzoate | 160 | 4.0 | -3.7 |
| Comparative example 7 | Diethyl carbitol | 160 | 4.0 | -0.7 |
| Comparative example 8 | Triglyme | 160 | 4.0 | -0.8 |
From the solution of embodiment 1～embodiment 5, obtain block polyethylene terephthalate except that desolvating by distillation.
Shown in embodiment 1～5, can find out that polyethylene terephthalate dissolves easily when using the acid amides series solvent.On the contrary, shown in comparative example 1～8, in the time of can finding out the solvent that uses beyond the acid amides, polyethylene terephthalate expands and does not dissolve.
(rate of decomposition of saturated polyester when use contains the decomposing solution of alkali and monohydroxy-alcohol)
As saturated polyester, will be in embodiment 6～15 and comparative example 9～11 commercially available polyethylene terephthalate (プ ラ ス チ ッ Network Industrial Co., Ltd system trade(brand)name in サ Application ロ ィ De ペ ッ ト ェ one ス EPG100, the tube), the polybutylene terephthalate in embodiment 16, the PEN in embodiment 17 are cut into the test film of 10mm * 30mm * thick 0.35mm size.With containing of specified amount various alkali and the solution of solvent monohydroxy-alcohol put in the glass test tube of 20ml capacity, after at room temperature slowly stirring, utilize oil bath that the temperature in each test tube is remained on 60 ℃.After surveying the quality of overtesting sheet, test film is immersed in each solution, cover the aluminum lid for preventing solvent evaporation.In through 4 hours, take out test film, measure quality again after washing, the drying, according to the quality change before and after the dipping, the quality of calculating decomposed saturated polyester is as rate of decomposition.
Each condition and the rate of decomposition of embodiment 6～17 and comparative example 9～11 are shown in table 2.In addition, in embodiment 14, refrigerating unit is installed on test tube, one side at 64 ℃ solution is refluxed, Yi Bian in addition the dip test sheet, carries out the processing identical with embodiment 6.In addition, in embodiment 15, with magnetic stirring apparatus stirred solution on one side, on one side the dip test sheet, in addition, carry out the processing identical with embodiment 6.
Table 2
| Alkali | Solvent | Concentration Annotate) (eq/1000g) | Concentration Annotate) (wt％) | Temperature (℃) | Time (h) | Rate of decomposition (%) | |
| Embodiment 6 | LiOH | MeOH | 1.00 | 2.3 | 60 | 4.0 | 12.9 |
| Embodiment 7 | NaOH | MeOH | 1.00 | 3.8 | 60 | 4.0 | 13.3 |
| Embodiment 8 | KOH | MeOH | 1.00 | 5.3 | 60 | 4.0 | 11.1 |
| Embodiment 9 | LiOCH 3 | MeOH | 1.00 | 3.7 | 60 | 4.0 | 10.8 |
| Embodiment 10 | NaOCH 3 | MeOH | 1.00 | 5.1 | 60 | 4.0 | 9.3 |
| Embodiment 11 | KOCH 3 | MeOH | 1.00 | 6.5 | 60 | 4.0 | 9.8 |
| Embodiment 12 | KOCH 3 | DGMM | 1.00 | 5.3 | 60 | 4.0 | 6.0 |
| Embodiment 13 | LiOH | MeOH | 2.00 | 4.6 | 60 | 4.0 | 22.5 |
| Embodiment 14 | LiOH | MeOH | 1.00 | 2.3 | 64 | 4.0 | 15.1 |
| Embodiment 15 | LiOH | MeOH | 1.00 | 2.3 | 60 | 4.0 | 16.8 |
| Embodiment 16 | LiOH | MeOH | 1.00 | 2.3 | 60 | 4.0 | 13.8 |
| Embodiment 17 | LiOH | MeOH | 1.00 | 2.3 | 60 | 4.0 | 10.3 |
| Comparative example 9 | - | MeOH | - | - | 60 | 4.0 | 0.2 |
| Comparative example 10 | - | DGMM | - | - | 60 | 4.0 | 0.0 |
| Comparative example 11 | KOH | Water | 1.00 | 6.5 | 60 | 4.0 | 0.3 |
Annotate:
LiOH: lithium hydroxide, NaOH: sodium hydroxide, KOH: potassium hydroxide, MeOH: methyl alcohol, LiOCH
3: lithium methoxide, NaOCH
3: potassium methylate, DGMM: diethylene glycol monomethyl ether.
Annotate) concentration (eq/1000g): positively charged ion gram equivalent/1000g solvent
Annotate) concentration (wt%): with respect to the phosphoric salt concentration of monohydroxy-alcohol
Among the embodiment 6～11,16 and 17,, also reach the rate of decomposition about 10% although various alkali concn is lower.In addition,, water cooler is installed on reaction unit solution is refluxed,, rate of decomposition is improved while stir to handle as embodiment 15 as embodiment 14.On the contrary, in comparative example 9～11, can not obtain rate of decomposition more than or equal to 1%.
In addition, in the solution that in embodiment 6～17, obtains, add water, add concentrated hydrochloric acid when solution is acidity, can separate out white crystal with amount.With its filtering separation, wash, drying.Use the infrared spectrophotometer 270-30 of Hitachi type to measure the infrared spectra of this material, by the NMR (Nuclear Magnetic Resonance) spectrum of nuclear magnetic resonance device Brooker AC300P mensuration 1H and 13C, measurement result can confirm that this material is a terephthalic acid.
(rate of decomposition of the saturated polyester when use contains the decomposing solution of phosphoric salt and monohydroxy-alcohol)
As saturated polyester, the polyethylene terephthalate that commercially available 0.35mm is thick (プ ラ ス チ ッ Network Industrial Co., Ltd system trade(brand)name in サ Application ロ ィ De ペ ッ ト ェ one ス EPG100, the tube) plate cutting is made into the test film of 10mm * 30mm.The solution that contains various phosphoric salts and monohydroxy-alcohol of weighing specified amount drops into 20ml in glass test tube, at room temperature slowly stirs and obtains decomposing solution.Utilize oil bath the solution of each test tube to be remained on the temperature of regulation.After surveying the quality of overtesting sheet, test film is immersed in each solution, for preventing that solvent evaporation from covering the aluminum lid and handling.Through specific time the time, take out test film, weighing again after washing, the drying, according to the quality change before and after the dipping, the ratio of calculating decomposed saturated polyester is as rate of decomposition.
Each condition and the rate of decomposition of embodiment 18～65 and comparative example 12～16 are shown in table 3.
Table 3
| Phosphoric salt | Monohydroxy-alcohol (solvent 1) | Solvent 2 | Solvent 1/ solvent 2 (weight ratio) | Concentration Annotate) (eq/1000g) | Concentration Annotate) (wt％) | Temperature (℃) | Time (h) | Rate of decomposition (%) | |
| Embodiment 18 | Na 3PO 4 | MeOH | - | - | 1.00 | 5.2 | 60 | 4.0 | 1.8 |
| Embodiment 19 | K 2HPO 4 | MeOH | - | - | 1.00 | 8.0 | 60 | 4.0 | 1.2 |
| Embodiment 20 | (NH 4) 3PO 4 | MeOH | - | - | 1.00 | 4.7 | 60 | 4.0 | 2.0 |
| Embodiment 21 | K 4P 2O 7 | MeOH | - | - | 1.00 | 7.6 | 60 | 4.0 | 1.4 |
| Embodiment 22 | K 3PO 4 | MeOH | - | - | 1.00 | 6.6 | 60 | 4.0 | 12.1 |
| Embodiment 23 | K 3PO 4 | EtOH | - | - | 1.00 | 6.6 | 60 | 4.0 | 2.7 |
| Embodiment 24 | K 3PO 4 | DGMM | - | - | 1.00 | 6.6 | 60 | 4.0 | 3.0 |
| Embodiment 25 | K 3PO 4 | BZA | - | - | 1.00 | 6.6 | 60 | 4.0 | 2.6 |
| Embodiment 26 | K 3PO 4 | DGMM | - | - | 1.00 | 6.6 | 160 | 4.0 | 36.4 |
| Embodiment 27 | K 3PO 4 | BZA | - | - | 1.00 | 6.6 | 160 | 4.0 | 43.3 |
| Embodiment 28 | K 3PO 4 | MeOH | - | - | 2.00 | 12.4 | 60 | 4.0 | 22.6 |
| Embodiment 29 | K 3PO 4 | MeOH | - | - | 5.00 | 26.1 | 60 | 4.0 | 42.6 |
| Embodiment 30 | K 3PO 4 | MeOH | - | - | 10.00 | 41.4 | 60 | 4.0 | 65.9 |
| Embodiment 31 | K 3PO 4 | MeOH | - | - | 20.00 | 58.6 | 60 | 4.0 | 82.9 |
| Embodiment 32 | K 3PO 4 | MeOH | - | - | 10.00 | 41.4 | 60 | 2.0 | 33.2 |
| Embodiment 33 | K 3PO 4 | MeOH | - | - | 10.00 | 41.4 | 60 | 6.0 | 56.8 |
| Embodiment 34 | K 3PO 4 | MeOH | - | - | 10.00 | 41.4 | 60 | 10.0 | 86.7 |
| Phosphoric salt | Monohydroxy-alcohol (solvent 1) | Solvent 2 | Solvent 1/ solvent 2 (weight ratio) | Concentration Annotate) (eq/1000g) | Concentration Annotate) (wt％) | Temperature (℃) | Time (h) | Rate of decomposition (%) | |
| Embodiment 35 | K 3PO 4 | MeOH | - | - | 20.00 | 58.6 | 60 | 2.0 | 47.9 |
| Embodiment 36 | K 3PO 4 | MeOH | - | - | 20.00 | 58.6 | 60 | 6.0 | 72.2 |
| Embodiment 37 | K 3PO 4 | MeOH | - | - | 20.00 | 58.6 | 60 | 10.0 | 100.0 |
| Embodiment 38 | Na 3PO 4·12H 2O | MeOH | - | - | 1.00 | 11.2 | 60 | 4.0 | 2.2 |
| Embodiment 39 | K 3PO 4·nH 2O | MeOH | - | - | 1.00 | 8.3 | 60 | 4.0 | 6.1 |
| Embodiment 40 | K 3PO 4·nH 2O | EtOH | - | - | 1.00 | 8.3 | 60 | 4.0 | 2.9 |
| Embodiment 41 | K 3PO 4·nH 2O | DGMM | - | - | 1.00 | 8.3 | 60 | 4.0 | 2.8 |
| Embodiment 42 | K 3PO 4·nH 2O | BZA | - | - | 1.00 | 8.3 | 60 | 4.0 | 3.2 |
| Embodiment 43 | K 3PO 4·nH 2O | DGMM | - | - | 1.00 | 8.3 | 160 | 4.0 | 38.5 |
| Embodiment 44 | K 3PO 4·nH 2O | BZA | - | - | 1.00 | 8.3 | 160 | 4.0 | 41.4 |
| Embodiment 45 | K 3PO 4·nH 2O | MeOH | - | - | 2.00 | 15.3 | 60 | 4.0 | 7.0 |
| Embodiment 46 | K 3PO 4·nH 2O | MeOH | - | - | 5.00 | 31.2 | 60 | 4.0 | 14.1 |
| Embodiment 47 | K 3PO 4·nH 2O | MeOH | - | - | 10.00 | 47.6 | 60 | 4.0 | 18.1 |
| Embodiment 48 | K 3PO 4·nH 2O | MeOH | - | - | 20.00 | 64.5 | 60 | 4.0 | 27.4 |
| Embodiment 49 | K 3PO 4·nH 2O | MeOH | - | - | 1.00 | 47.6 | 60 | 10.0 | 32.1 |
| Embodiment 50 | K 3PO 4·nH 2O | MeOH | - | - | 10.00 | 47.6 | 60 | 10.0 | 73.2 |
| Embodiment 51 | K 3PO 4·nH 2O | MeOH | - | - | 20.00 | 47.6 | 60 | 10.0 | 54.7 |
| Embodiment 52 | K 3PO 4·nH 2O | MeOH | - | - | 1.00 | 64.5 | 60 | 20.0 | 55.4 |
| Phosphoric salt | Monohydroxy-alcohol (solvent 1) | Solvent 2 | Solvent 1/ solvent 2 (weight ratio) | Concentration Annotate) (eq/1000g) | Concentration Annotate) (wt％) | Temperature (℃) | Time (h) | Rate of decomposition (%) | |
| Embodiment 53 | K 3PO 4·nH 2O | MeOH | - | - | 10.00 | 64.5 | 60 | 20.0 | 91.1 |
| Embodiment 54 | K 3PO 4·nH 2O | MeOH | - | - | 20.00 | 64.5 | 60 | 20.0 | 100.0 |
| Embodiment 55 | K 3PO 4 | MeOH | Water | 1.0/1.0 | 1.00 | 8.3 | 60 | 4.0 | 2.7 |
| Embodiment 56 | K 3PO 4 | MeOH | Methyl phenyl ketone | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 24.0 |
| Embodiment 57 | K 3PO 4 | MeOH | Methylethylketone | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 28.3 |
| Embodiment 58 | K 3PO 4 | MeOH | Acetone | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 23.2 |
| Embodiment 59 | K 3PO 4 | MeOH | N, dinethylformamide | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 22.7 |
| Embodiment 60 | K 3PO 4 | MeOH | N,N-dimethylacetamide | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 27.6 |
| Embodiment 61 | K 3PO 4 | MeOH | N-Methyl pyrrolidone | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 28.4 |
| Embodiment 62 | K 3PO 4 | MeOH | Glycol diacetate | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 29.4 |
| Embodiment 63 | K 3PO 4 | MeOH | Toluene | 1.0/1.0 | 1.0 | 6.6 | 60 | 4.0 | 28.7 |
| Embodiment 64 | K 3PO 4·nH 2O | MeOH | N,N-dimethylacetamide | 1.0/1.0 | 1.0 | 8.3 | 60 | 4.0 | 27.6 |
| Embodiment 65 | K 3PO 4 | MeOH | N,N-dimethylacetamide | 1.0/1.0 | 10.0 | 41.4 | 60 | 4.0 | 77.2 |
| Comparative example 12 | - | MeOH | - | - | - | - | 60 | 4.0 | 0.2 |
| Comparative example 13 | - | EtOH | - | - | - | - | 60 | 4.0 | 0.3 |
| Comparative example 14 | - | DGMM | - | - | - | - | 160 | 4.0 | 0.1 |
| Comparative example 15 | - | BZA | - | - | - | - | 160 | 4.0 | 0.2 |
| Comparative example 16 | K 3PO 4 | - | Methyl phenyl ketone | - | - | - | 160 | 4.0 | -0.7 |
Annotate:
Na
3PO
4: tertiary sodium phosphate, Na
3PO
412H
2O: tertiary sodium phosphate 12 hydrates, K
3PO
4NH
2O: Tripotassium phosphate n hydrate (Tripotassium phosphate content is 74-85% for trade(brand)name, Northeast chemistry (society) system), K
2HPO
4: dipotassium hydrogen phosphate, (NH
4)
3PO
4: triammonium phosphate, K
4P
2O
7: potassium pyrophosphate, K
3PO
4: Tripotassium phosphate, MeOH: methyl alcohol, EtOH: ethanol, DGMM: diethylene glycol monomethyl ether, BZA: phenylcarbinol.
Annotate) concentration (eq/1000g): positively charged ion gram equivalent/1000g solvent
Annotate) concentration (wt%): with respect to the phosphoric salt concentration of monohydroxy-alcohol
As shown in table 3, contain among the embodiment 18～65 of solution of various phosphoric salts and monohydroxy-alcohol in use, all show rate of decomposition more than or equal to 1%.Wherein, shown in embodiment 37, find the condition that whole polyethylene terephthalates decomposed at 60 ℃, 10 hours.In addition, shown in embodiment 56～65, when using other solvents beyond the methyl alcohol, any one is compared during with independent use methyl alcohol, all demonstrates about 2～4 times rate of decomposition together.With respect to these embodiment, in comparative example 12～15, owing to use not phosphorous acids salt that the solution-treated of monohydroxy-alcohol is only arranged, in comparative example 16, owing to do not use monohydroxy-alcohol as solvent, any one rate of decomposition is all smaller or equal to 1%.
In addition, in embodiment 18～37,46～54, after the disaggregating treatment, in the solution after in embodiment 56～65, handling,, separate out white crystal by adding the water of 10 times of amounts.Then, after removing by filter solvent, removing phosphoric salt by washing, drying obtains white powder.
Use the infrared spectrophotometer 270-30 of Hitachi type to measure the infrared spectra of this white powder, measure the NMR (Nuclear Magnetic Resonance) spectrum of 1H and 13C by nuclear magnetic resonance device Brooker AC300P, the result is consistent with the wave spectrum of dimethyl terephthalate (DMT), confirms that this material is a dimethyl terephthalate (DMT).Purity is 99%.
And, for embodiment 18～37,,, obtain transparent liquid by the filtering separation phosphoric salt desolvating smaller or equal to filtrate the removing of 100 ℃ of distillation aforesaid operations.With above-mentioned same, measure the NMR (Nuclear Magnetic Resonance) spectrum of infrared spectra, 1H and the 13C of this liquid, the result is consistent with the wave spectrum of ethylene glycol, confirms that this material is an ethylene glycol.
And, for embodiment 46～54, in filtrate, add water with amount, at room temperature, add concentrated hydrochloric acid when being acidity, separate out white crystal.With its filtering separation, wash, drying.Measure IR spectrum, MR spectrum, the result can confirm that this material is a terephthalic acid.Purity is 98%.In addition, in the filtrate of embodiment 22, carry out identical operations, but in this case, do not see the generation that terephthalic acid is arranged.
Like this, at normal pressure, be lower than under the boiling point that equals solution, polyethylene terephthalate can be resolved into dimethyl terephthalate (DMT) and ethylene glycol by single step reaction.And, using as phosphoric salt among the embodiment of its hydrate, also can access terephthalic acid.
In addition, in above-mentioned whole embodiment, if use stirrer, pressurized vessel, water cooler etc., then dispersion efficiency raising, treatment time shorten obviously.And if the applying pressure container is handled under the temperature that is higher than more than the boiling point that equals solvent, then the treatment time shortens.If the use water cooler can carry out long time treatment under the boiling point of solvent, the treatment time obviously also shortens.
Therefore, according to the present invention owing to can under normal pressure, low temperature, carry out the dissolving or the decomposition of saturated polyester, therefore, with in the past technology relatively, can be easily and utilize saturated polyester cheaply again.
Present technique field personnel should be clear, and aforementioned just the preferred embodiment of the present invention under the situation of the spirit and scope of the present invention, can be carried out multiple changes and improvements to the present invention.
Claims (7)
1. the dissolving method of a saturated polyester is characterized in that, uses acid amides series solvent dissolving saturated polyester.
2. the dissolving method of saturated polyester according to claim 1 is characterized in that, described saturated polyester is a poly terephthalic acid alkane diol ester.
3. the dissolving method of saturated polyester according to claim 1 and 2 is characterized in that, described acid amides series solvent at room temperature be liquid, and its boiling point is more than or equal to 180 ℃.
4. the dissolving method of saturated polyester according to claim 1 and 2 is characterized in that, described acid amides series solvent is a N-Methyl pyrrolidone.
5. the dissolving method of saturated polyester according to claim 1 and 2 is characterized in that, dissolves under normal pressure.
6. the dissolving method of saturated polyester according to claim 1 and 2 is characterized in that, dissolves under the temperature of zero pour smaller or equal to boiling point more than or equal to described acid amides series solvent.
7. the dissolving method of saturated polyester according to claim 1 and 2 is characterized in that, the temperature of the described acid amides series solvent during dissolving is 130～190 ℃.
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