CN117794991A - Monomer composition for synthesizing recycled plastic, method for preparing the same, recycled plastic using the same, and molded product - Google Patents
Monomer composition for synthesizing recycled plastic, method for preparing the same, recycled plastic using the same, and molded product Download PDFInfo
- Publication number
- CN117794991A CN117794991A CN202380013113.2A CN202380013113A CN117794991A CN 117794991 A CN117794991 A CN 117794991A CN 202380013113 A CN202380013113 A CN 202380013113A CN 117794991 A CN117794991 A CN 117794991A
- Authority
- CN
- China
- Prior art keywords
- synthesizing
- monomer composition
- recycled plastic
- aromatic diol
- diol compound
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 116
- 239000000178 monomer Substances 0.000 title claims abstract description 116
- 239000004033 plastic Substances 0.000 title claims abstract description 115
- 229920003023 plastic Polymers 0.000 title claims abstract description 115
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 43
- -1 aromatic diol compound Chemical class 0.000 claims abstract description 126
- 239000012535 impurity Substances 0.000 claims abstract description 22
- 239000004417 polycarbonate Substances 0.000 claims description 61
- 229920000515 polycarbonate Polymers 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000011347 resin Substances 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 26
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 20
- 150000001409 amidines Chemical class 0.000 claims description 13
- 150000002009 diols Chemical class 0.000 claims description 13
- 239000002608 ionic liquid Substances 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 4
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 21
- 239000002243 precursor Substances 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 238000002144 chemical decomposition reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000004064 recycling Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 238000012691 depolymerization reaction Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000013076 target substance Substances 0.000 description 4
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000005587 carbonate group Chemical group 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HNDVYGDZLSXOAX-UHFFFAOYSA-N 2,6-dichloro-4-propylphenol Chemical compound CCCC1=CC(Cl)=C(O)C(Cl)=C1 HNDVYGDZLSXOAX-UHFFFAOYSA-N 0.000 description 1
- HJZJMARGPNJHHG-UHFFFAOYSA-N 2,6-dimethyl-4-propylphenol Chemical compound CCCC1=CC(C)=C(O)C(C)=C1 HJZJMARGPNJHHG-UHFFFAOYSA-N 0.000 description 1
- UFUBQDNODUUQTD-UHFFFAOYSA-N 2-bromo-4-propylphenol Chemical compound CCCC1=CC=C(O)C(Br)=C1 UFUBQDNODUUQTD-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- QEMHBAGGYKJNSS-UHFFFAOYSA-N 2-icosylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O QEMHBAGGYKJNSS-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- OREKREJVUNVFJP-UHFFFAOYSA-N 2-triacontylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O OREKREJVUNVFJP-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- XHASMJXNUHCHBL-UHFFFAOYSA-N 4-(1-phenylethyl)phenol Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=CC=C1 XHASMJXNUHCHBL-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- HINMGNHBDCADKG-UHFFFAOYSA-N 5-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=CNC=N1 HINMGNHBDCADKG-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000010102 injection blow moulding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000010137 moulding (plastic) Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000009283 thermal hydrolysis Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
The present invention relates to a monomer composition for synthesizing a recycled plastic, which comprises an aromatic diol compound, wherein the ratio of aromatic diol compound derivative impurities according to equation 1 is 0.5% or less, wherein the purity of the aromatic diol compound is 99.25% or more, and a recycled plastic and a molded product using the same, and a method for preparing the same.
Description
Technical Field
Cross Reference to Related Applications
The present application claims the benefits of korean patent application No. 10-2022-0045959 filed on month 13 of 2022 and korean patent application No. 10-2023-0044307 filed on month 4 of 2023, which are incorporated herein by reference in their entireties.
The present invention relates to a monomer composition for synthesizing a recycled plastic comprising a high-purity aromatic diol compound recovered by recycling through chemical decomposition of a polycarbonate-based resin, a method for preparing the same, and a recycled plastic and a molded product using the same.
Background
Polycarbonates are thermoplastic polymers and are plastics having excellent properties such as excellent transparency, ductility and relatively low manufacturing costs.
Although polycarbonates are widely used in a variety of applications, environmental and health problems during waste disposal have been continually raised.
At present, physical recycling methods have been performed, but in this case, problems associated with degradation of quality occur, and thus, studies on chemical recycling of polycarbonates have been underway.
Chemical decomposition of polycarbonate means that an aromatic diol compound (e.g., bisphenol A; BPA) as a monomer is obtained by decomposition of polycarbonate, which is then reused in polymerization to obtain a high-purity polycarbonate.
For such chemical decomposition, thermal decomposition, hydrolysis and alcohol decomposition are generally known. Among them, the most commonly used method is alcohol decomposition using a base catalyst, but in the case of methanol decomposition, there is a problem in that methanol harmful to the human body is used, and in the case of ethanol, there is a problem in that high temperature and high pressure conditions are required and productivity is not high.
Disclosure of Invention
Technical problem
It is an object of the present invention to provide a monomer composition for synthesizing recycled plastics, which can ensure a high-purity aromatic diol compound recovered by recycling through chemical decomposition of a polycarbonate-based resin.
It is another object of the present invention to provide a method for preparing a monomer composition for synthesizing recycled plastic, recycled plastic and molded products using the same.
Technical proposal
In order to achieve the above object, provided herein is a monomer composition for synthesizing recycled plastics, comprising an aromatic diol compound, wherein the ratio of aromatic diol compound derivative impurities according to the following equation 1 is 0.5% or less, wherein the purity of the aromatic diol compound is 99.25% or more, and wherein the monomer composition for synthesizing recycled plastics is recovered from a polycarbonate-based resin.
[ equation 1]
Ratio (%) = (peak area of aromatic diol compound derivative in HPLC/total peak area in HPLC) ×100 of aromatic diol compound derivative impurities.
Also provided herein is a method of preparing a monomer composition for synthesizing recycled plastic, the method comprising the steps of: adding polycarbonate to an organic solvent to prepare a mixed solution; adding a glycol-based compound and an ionic liquid catalyst to the mixed solution and stirring them; obtaining the aromatic diol compound formed in the stirring step.
Also provided herein are recycled plastics comprising the reaction product of a monomer composition and a comonomer for synthesizing recycled plastics.
Molded products comprising the recycled plastic are also provided herein.
Hereinafter, a monomer composition for synthesizing recycled plastic, a method of preparing the same, recycled plastic using the same, and molded products according to specific embodiments of the present invention will be described in more detail.
Unless explicitly stated herein, the technical terms used herein are for the purpose of describing particular embodiments only and are not intended to limit the scope of the present invention.
As used herein, singular expressions may include plural expressions unless they are expressed differently in context.
It will be understood that the terms "comprises," "comprising," "includes," "including" and/or "having," when used herein, specify the presence of stated features, regions, integers, steps, actions, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, actions, elements, components, and/or groups.
Furthermore, terms including ordinal numbers such as "first," "second," and the like are used solely for the purpose of distinguishing one component from another and are not limited by the ordinal numbers. For example, a first component may be referred to as a second component, or similarly, a second component may be referred to as a first component, without departing from the scope of the invention.
As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a primary amino group; a carboxyl group; a sulfonic acid group; sulfonamide groups; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkoxysilylalkyl group; aryl phosphino; and a heterocyclic group comprising at least one of N, O and S atoms, or a substituent which is unsubstituted or linked via two or more of the substituents exemplified above. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl, or it may also be interpreted as a substituent to which two phenyl groups are linked.
As used herein, alkyl is a monovalent functional group derived from an alkane, and may be linear or branched. The number of carbon atoms of the linear alkyl group is not particularly limited, but is preferably 1 to 20. In addition, the branched alkyl group has 3 to 20 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, 2, 6-dimethylheptane-4-yl and the like. The alkyl group may be substituted or unsubstituted, and when substituted, examples of the substituent are the same as described above.
As used herein, alkylene is a divalent functional group derived from an alkane, and the above description of alkyl groups can be applied, except that these are divalent functional groups. For example, the linear or branched alkylene group may include methylene, ethylene, propylene, isobutylene, sec-butylene, tert-butylene, pentylene, hexylene, and the like. The alkylene group may be substituted or unsubstituted.
As used herein, fused ring means that in a polycyclic ring system consisting of two or more carbocyclic or heterocyclic rings, the rings adjacent to each other share only the cyclic structure of the two atoms forming each ring.
As used herein, "one or more" means, for example, "1, 2, 3, 4, or 5, specifically 1, 2, 3, or 4, more specifically 1, 2, or 3, and more specifically 1 or 2.
1. Monomer composition for synthesizing recycled plastics
According to an embodiment of the present invention, there may be provided a monomer composition for synthesizing a recycled plastic, the monomer composition for synthesizing a recycled plastic comprising an aromatic diol compound, wherein a ratio of impurities of an aromatic diol compound derivative according to the following equation 1 is 0.5% or less, wherein a purity of the aromatic diol compound is 99.25% or more, and wherein the monomer composition for synthesizing a recycled plastic is recovered from a polycarbonate-based resin.
[ equation 1]
Ratio (%) = (peak area of aromatic diol compound derivative in HPLC/total peak area in HPLC) ×100 of aromatic diol compound derivative impurities.
The present inventors found through experiments that although the monomer composition for synthesizing recycled plastic of one embodiment is recovered by recycling through chemical decomposition of a polycarbonate-based resin, the composition satisfies the characteristics of high purity of the newly synthesized aromatic diol compound level and significantly reduced impurities of the aromatic diol compound derivative, thereby being capable of achieving excellent physical properties when synthesizing a polycarbonate-based resin using the composition, and completed the present invention.
The invention can have the following technical characteristics: by conducting regeneration via chemical decomposition of the polycarbonate-based resin, a composition containing an aromatic diol compound can be obtained in high purity.
In particular, the monomer composition for synthesizing recycled plastic of one embodiment is characterized in that it is recovered from a polycarbonate-based resin. That is, this means that recovery from the polycarbonate-based resin is performed in order to obtain the monomer composition for synthesizing recycled plastic of one embodiment, and as a result, the monomer composition for synthesizing recycled plastic containing the aromatic diol compound is obtained at the same time.
Polycarbonate-based resin is meant to include both homopolymers and copolymers comprising polycarbonate repeating units, and refers collectively to the reaction product obtained by polymerization or copolymerization of monomers comprising an aromatic diol compound and a carbonate precursor. When it contains one carbonate repeating unit obtained by using only one aromatic diol compound and one carbonate precursor, a homopolymer can be synthesized. Further, when one aromatic diol compound and two or more carbonate precursors are used as monomers, or two or more aromatic diol compounds and one carbonate precursor are used, or one or more other diols are used in addition to the one aromatic diol compound and the one carbonate precursor to thereby contain two or more carbonates, a copolymer may be synthesized. The homopolymer or copolymer may include all of low molecular compounds, oligomers, and polymers depending on the molecular weight range.
In addition, the monomer composition for synthesizing recycled plastic of one embodiment may include an aromatic diol compound. Specific examples of the aromatic diol compound include bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) sulfoxide, bis (4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) ketone, 1-bis (4-hydroxyphenyl) ethane, 2-bis (4-hydroxyphenyl) propane (bisphenol A), 2-bis (4-hydroxyphenyl) butane, 1-bis (4-hydroxyphenyl) cyclohexane (bisphenol Z) 2, 2-bis (4-hydroxy-3, 5-dibromophenyl) propane, 2-bis (4-hydroxy-3, 5-dichlorophenyl) propane, 2-bis (4-hydroxy-3-bromophenyl) propane, 2-bis (4-hydroxy-3-chlorophenyl) propane 2, 2-bis (4-hydroxy-3-methylphenyl) propane, 2-bis (4-hydroxy-3, 5-dimethylphenyl) propane, 1-bis (4-hydroxyphenyl) -1-phenylethane, or a mixture of two or more thereof, and the like. Preferably, the aromatic diol compound of the monomer composition for synthesizing recycled plastic of one embodiment may be 2, 2-bis (4-hydroxyphenyl) propane (bisphenol a).
The aromatic diol compound is characterized in that it is recovered from a polycarbonate-based resin used for recovering a monomer composition for synthesizing recycled plastics. That is, this means that recovery from the polycarbonate-based resin is carried out in order to obtain the monomer composition for synthesizing recycled plastic of one embodiment, and as a result, an aromatic diol compound is also obtained at the same time. Therefore, the case of externally adding a new aromatic diol compound is not included in the scope of the aromatic diol compound of the present invention, except for the monomer composition for synthesizing recycled plastic, which is recovered from the polycarbonate-based resin to prepare one embodiment.
Specifically, "recovered from a polycarbonate-based resin" means obtained by depolymerization reaction of a polycarbonate-based resin. The depolymerization reaction may be carried out under acidic, neutral or alkaline conditions, and in particular, the depolymerization reaction may be carried out under alkaline (alkali-containing) conditions. In particular, as will be described later, the depolymerization reaction may be preferably performed in the presence of a diol-based compound.
Meanwhile, the monomer composition for synthesizing the recycled plastic may further contain impurities other than the aromatic diol compound. The impurity means an aromatic diol compound derivative excluding an aromatic diol compound which is a main target substance to be recovered in the present invention.
The derivative of the aromatic diol compound may include one or more compounds selected from the group consisting of monohydroxy-bisphenol a and bishydroxy-ethyl-bisphenol a.
That is, the derivative of the aromatic diol compound may include one type of monohydroxyethyl-bisphenol a, one type of bishydroxyethyl-bisphenol a, or a mixture of both types thereof.
In the same manner as a method for preparing a monomer composition for synthesizing recycled plastic, which will be described later, an organic solvent and an ionic liquid catalyst are introduced to promote chemical decomposition of polycarbonate by a diol-based compound under mild reaction conditions, so that generation of derivative impurities of an aromatic diol compound can be significantly reduced.
Specifically, the monomer composition for synthesizing the recycled plastic may have a ratio of the aromatic diol compound derivative impurity according to equation 1, the upper limit of the ratio ranging from 0.5% or less, or 0.4% or less, or 0.3% or less, or 0.2% or less, or 0.13% or less, and the lower limit of the ratio ranging from 0.01% or more, or 0.05% or more, or 0.08% or more, or 0.09% or more, or 0.1% or more, or 0.11% or more, or 0.12% or more. Numerical ranges from a lower limit to an upper limit may also be satisfied by combining the upper and lower ranges. In one example of the numerical range of the lower limit to the upper limit, the ratio of the aromatic diol compound derivative impurity according to equation 1 may be 0.01% to 0.5%.
According to equation 1, the% as a unit of the ratio of the aromatic diol compound derivative impurity is the peak area ratio in HPLC and means area%.
In equation 1, the peak area of the aromatic diol compound derivative in HPLC is the total peak area of each of the one or more aromatic diol compound derivatives. For example, when the aromatic diol compound derivative is a mixture of two types of monohydroxy-bisphenol a and dihydroxyethyl-bisphenol a, it means the total peak area of each of monohydroxy-bisphenol a and dihydroxyethyl-bisphenol a.
More specifically, monohydroxy-bisphenol a [ MHE-BPA ] may show a peak at an HPLC retention time of 2.84 minutes, and bis-hydroxyethyl-bisphenol a [ BHE-BPA ] may show a peak at an HPLC retention time of 2.61 minutes.
Examples of the method for measuring the weight ratio of the aromatic diol compound derivative impurities of the monomer composition for synthesizing a recycled plastic of one embodiment are not particularly limited, and High Performance Liquid Chromatography (HPLC) analysis may be used, for example. As for the specific method, conditions, equipment, etc. of HPLC, various known contents can be applied without limitation. However, as an example, the regenerated bisphenol a monomer composition was dissolved in Acetonitrile (ACN) solvent at 1 wt% under normal pressure and 20 ℃ to 30 ℃ and then the weight ratio can be measured via a Waters HPLC system (e 2695 separation module, 2998PDA detector) using UG120 (4.6 mm i.dx 50 mm). More specifically, the weight ratio can be measured under the following conditions: (1) column: UG120 (4.6 mm i.dx 50 mm), (2) column temperature: 40 ℃, (3) injection volume: 10 μl, (4) flow rate: THF: ACN: water=15:15:70, volume=1.23 ml/min (total=10 min), and (5) detector: 245nm.
In this way, in the monomer composition for synthesizing recycled plastic of one embodiment, the content of the derivative impurities of the aromatic diol compound other than the aromatic diol compound as a main target substance to be recovered is significantly reduced, so that excellent physical properties can be achieved when a polycarbonate-based resin is synthesized using the same.
Meanwhile, the color coordinate b of the monomer composition for synthesizing recycled plastic of one embodiment may have a value of 0.01 to 2, 0.5 to 1.2, or 0.58 to 1.11. That is, the monomer composition for synthesizing recycled plastic of one embodiment may have such color coordinates b: the lower limit thereof ranges from 0.01 or more, or from 0.5 or more, or from 0.58 or more, or from 0.6 or more, or from 0.7 or more, or from 0.8 or more, or from 0.9 or more, or from 1.0 or more, or from 1.1 or more, and the upper limit thereof ranges from 2 or less, or from 1.2 or less, or from 1.11 or less. Numerical ranges from a lower limit to an upper limit may also be satisfied by combining the upper and lower ranges.
Further, the color coordinate L of the monomer composition for synthesizing recycled plastic of one embodiment may have a value of 94 to 99, or 95 to 98, or 95.77 to 97.49. That is, the monomer composition for synthesizing recycled plastic of one embodiment may have such color coordinates L x value: the lower limit thereof is 94 or more, or 95 or more, or 95.77 or more, or 96 or more, or 96.3 or more, or 96.6 or more, or 96.9 or more, or 97.2 or more, or 97.4 or more, and the upper limit thereof is 99 or less, or 98 or less, or 97.49 or less. Numerical ranges from a lower limit to an upper limit may also be satisfied by combining the upper and lower ranges.
In addition, the color coordinate a of the monomer composition for synthesizing recycled plastic of one embodiment may have a value of 0.01 to 1.5, or 0.1 to 1, or 0.10 to 0.23. That is, the monomer composition for synthesizing recycled plastic of one embodiment may have such color coordinates a x values: the lower limit thereof is in the range of 0.01 or more, or 0.1 or more, or 0.12 or more, or 0.14 or more, or 0.16 or more, or 0.18 or more, or 0.2 or more, or 0.22 or more, and the upper limit thereof is in the range of 1.5 or less, or 1 or less, or 0.23 or less. Numerical ranges from a lower limit to an upper limit may also be satisfied by combining the upper and lower ranges.
As used herein, "color coordinates" means coordinates in the CIE Lab color space, which are color values defined by the CIE (international commission on illumination, commossion International de L' Eclairage), and any position in the CIE color space can be represented by three coordinate values (i.e., L, a, and b).
Here, the value L represents luminance, when l=0, it represents black, and when l=100, it represents white. Further, the a value represents a color having a corresponding color coordinate biased toward one of pure red and pure green, and the b value represents a color having a corresponding color coordinate biased toward one of pure yellow and pure blue.
Specifically, a is in the range of-a to +a. The maximum value of a (a max) represents pure red, and the minimum value of a (a min) represents pure green. Furthermore, the value of b is in the range-b to +b. The maximum value of b (b max) represents pure yellow and the minimum value of b (b min) represents pure blue. For example, a negative b-value indicates a color that is biased toward pure blue, and a positive b-value indicates a color that is biased toward pure yellow. When b=50 is compared to b=80, b=80 is closer to pure yellow than b=50.
When the value of the color coordinate b of the monomer composition for synthetic recycled plastic of one embodiment excessively increases to more than 2, the monomer composition for synthetic recycled plastic of one embodiment exhibits a color excessively biased toward yellow, resulting in deterioration of color characteristics. Further, when the color coordinate b of the monomer composition for synthetic recycled plastic of one embodiment is excessively reduced to less than 0.01, the monomer composition for synthetic recycled plastic of one embodiment exhibits a color excessively biased toward blue, resulting in deterioration of color characteristics.
When the color coordinate L of the monomer composition for synthetic recycled plastic of one embodiment is excessively reduced to less than 94, the color characteristics of the monomer composition for synthetic recycled plastic of one embodiment deteriorate.
Meanwhile, when the color coordinate a value of the monomer composition for synthetic recycled plastic of one embodiment excessively increases to more than 1.5, the monomer composition for synthetic recycled plastic of one embodiment exhibits a color excessively biased toward red, resulting in deterioration of color characteristics. In addition, when the color coordinate a value of the monomer composition for synthetic recycled plastic of one embodiment is excessively reduced to less than 0.01, the monomer composition for synthetic recycled plastic of one embodiment exhibits a color excessively biased toward green, resulting in deterioration of color characteristics.
Examples of the method for measuring the color coordinates L, a, b of the monomer composition for synthesizing recycled plastic of one embodiment are not particularly limited, and various color characteristic measurement methods in the plastic field may be applied without limitation.
However, as an example, the color coordinates L, a, and b values of the monomer composition for synthesizing recycled plastic of one embodiment may be measured in reflection mode using a HunterLab UltraSACN PRO spectrophotometer.
Meanwhile, the monomer composition for synthesizing recycled plastic of one embodiment may have such an aromatic diol compound purity: the lower limit thereof ranges from 99.25% or more, or from 99.3% or more, or from 99.4% or more, or from 99.5% or more, or from 99.6% or more, or from 99.7% or more, or from 99.8% or more, and the upper limit thereof ranges from 100% or less, or from 99.9% or less. Numerical ranges from a lower limit to an upper limit may also be satisfied by combining the upper and lower ranges. As an example of the numerical range of the lower limit to the upper limit, the purity of the aromatic diol compound may be 99.25% to 100%.
For measuring one embodiment ofExamples of the method of synthesizing the purity of the aromatic diol compound of the monomer composition of the recycled plastic are not particularly limited, and for example, can be used without limitation 1 H NMR, ICP-MS analysis, HPLC analysis, UPLC analysis, and the like. As for the specific methods, conditions, equipment and the like of NMR, ICP-MS, HPLC and UPLC, various known contents can be applied without limitation.
One example of a method for measuring the purity of an aromatic diol compound of a monomer composition for synthesizing recycled plastic according to one embodiment is as follows. 1% by weight of the monomer composition for synthesizing recycled plastic according to one embodiment is dissolved in Acetonitrile (ACN) solvent under normal pressure and at 20℃to 30℃and then usedThe purity of bisphenol a (BPA) was analyzed by UPLC (ultra performance liquid chromatography) on a Waters HPLC system with BEH C18.7 μm (2.1 x 50mm column).
As described above, in the monomer composition for synthesizing recycled plastic of one embodiment, the purity of the aromatic diol compound, which is a main target substance to be recovered, is greatly increased to 99.25% or more, and other impurities are minimized, thereby enabling excellent physical properties to be achieved when a polycarbonate-based resin is synthesized using the same.
The monomer composition for synthesizing recycled plastics of one embodiment may be used as a raw material for preparing various recycled plastics, such as Polycarbonate (PC), which will be described later.
The monomer composition for synthesizing recycled plastic of one embodiment may further contain a small amount of other additives and solvents. The specific type of the additive or solvent is not particularly limited, and various substances widely used in the recovery of the aromatic diol compound through depolymerization of the polycarbonate-based resin can be applied without limitation.
The monomer composition for synthesizing recycled plastic of one embodiment may be obtained by a method of preparing the monomer composition for synthesizing recycled plastic, which will be described later. That is, the monomer composition for synthesizing recycled plastic of one embodiment corresponds to a resultant obtained by various processes of filtering, purifying, washing and drying to ensure that only the aromatic diol compound, which is a main target substance to be recovered, has high purity after the depolymerization reaction of the polycarbonate-based resin.
2. Method for producing monomer compositions for the synthesis of recycled plastics
According to another embodiment of the present invention, there may be provided a method for preparing a monomer composition for synthesizing recycled plastics, the method comprising the steps of: adding polycarbonate to an organic solvent to prepare a mixed solution; adding a glycol-based compound and an ionic liquid catalyst to the mixed solution and stirring them; obtaining the aromatic diol compound formed in the stirring step.
Specifically, the present invention has the following advantages: the polycarbonate is decomposed into a diol-based compound under mild conditions, so that bisphenol A as a high-purity monomer can be stably obtained.
Polycarbonate is meant to include both homopolymers and copolymers comprising polycarbonate and refers collectively to the reaction product obtained by polymerization or copolymerization of monomers comprising an aromatic diol compound and a carbonate precursor. When it contains one carbonate repeating unit obtained by using only one aromatic diol compound and one carbonate precursor, a homopolymer can be synthesized. Further, when one aromatic diol compound and two or more carbonate precursors are used as monomers, or two or more aromatic diol compounds and one carbonate precursor are used, or one or more other diols are used in addition to the one aromatic diol compound and the one carbonate precursor to contain two or more carbonates, the copolymer may be synthesized. The homopolymer or copolymer may include all of low molecular compounds, oligomers, and polymers depending on the molecular weight range.
Polycarbonate-based resins can be used regardless of various forms and types (e.g., new polycarbonate produced by synthesis, recycled polycarbonate produced by recycling processes, or polycarbonate waste).
In the present invention, the diol-based compound may include both a diol compound and a derivative compound thereof, and in particular, the diol-based compound may include an alkylene diol. Specific examples of the alkylene glycol are not particularly limited, and conventionally known various alkylene glycols may be used without limitation. One example is ethylene glycol or propylene glycol.
Meanwhile, the organic solvent may include one or more solvents selected from the group consisting of: tetrahydrofuran, toluene, methylene chloride, chloroform, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate and dipropyl carbonate. That is, the organic solvent may include tetrahydrofuran, toluene, methylene chloride, chloroform, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, dipropyl carbonate, or a mixture of two or more thereof.
In particular, when methylene chloride is used as an organic solvent, there is an advantage in that the dissolution characteristics of polycarbonate can be improved and the reactivity can be improved.
The weight ratio of the diol-based compound, the organic solvent, and the polycarbonate is not particularly limited, but as one example, the weight ratio between the diol-based compound and the polycarbonate may be 10:1 to 1:10, or 1:1 to 1:5, or 1:1 to 1:2, or 1:1.2 to 1:2.
Furthermore, the weight ratio between the organic solvent and the polycarbonate may be 10:1 to 1:10, or 10:1 to 1:1, or 10:1 to 2:1, or 2:1 to 5:1, or 2:1 to 3:1, or 2.5:1 to 3:1.
Furthermore, the weight ratio between the organic solvent and the glycol-based compound may be 10:1 to 1:10, or 1:1 to 10:1, or 2:1 to 5:1, or 3:1 to 4:1.
Specifically, by mixing the polycarbonate compound and the organic solvent in the above-described range, there is an advantage in that the depolymerization reaction of the polymer can be performed at a desired level.
The ionic liquid catalyst may be added in an amount of 0.1 to 10 parts by weight, or 0.1 to 5 parts by weight, or 0.1 to 4 parts by weight, or 0.1 to 3 parts by weight, or 0.1 to 2 parts by weight, or 0.1 to 1 part by weight, based on 100 parts by weight of the polycarbonate. In particular, by including the ionic liquid catalyst in the above-described content range, there is an advantage in that an economical catalytic reaction can be performed.
The ionic liquid catalyst may be present in the form of a salt comprising an organic cation and an organic anion, and may specifically comprise an amidine-based salt compound. The amidine-based salt compound may comprise an amidine-based cation and an imidazole-based anion. The amidine-based cations may include all amidine cations or derived cations thereof. The imidazole-based cation may include all imidazole anions or anions derived therefrom.
In particular, the amidine-based salt compound may comprise an amidine-based cation having a fused ring. The fused ring may include a fused ring of 7-membered ring and 6-membered ring. The 7-membered ring means a case where the number of elements constituting the ring is 7, and the 6-membered ring means a case where the number of elements constituting the ring is 6, respectively.
The 6-membered ring may comprise the c=n double bond of the amidine. The 7-membered ring may comprise the C-C single bond of the amidine. In addition, the C-N single bond of the amidine may be contained in the portion where the 7-membered ring overlaps the 6-membered ring.
More specifically, specific examples of the ionic liquid catalyst may include a salt compound represented by the following chemical formula a:
[ chemical formula A ]
Wherein in formula A, R 1 、R 2 And R is 3 Are identical or different from one another and can each independently be hydrogen or alkyl.
Detailed examples of the ionic liquid catalyst represented by formula a may include one wherein R in formula a 1 ＝R 2 ＝R 3 Compound a of formula (a) =hydrogen (H), wherein R in formula a 1 ＝R 3 =hydrogen (H) and R 2 =methyl (CH) 3 ) Wherein R in formula A 1 ＝R 2 =hydrogen (H) and R 3 =methyl (CH) 3 ) Wherein R in formula A 1 ＝R 3 =hydrogen (H) and R 2 Compound d=isopropyl, wherein R in formula a 1 ＝R 2 =hydrogen (H) and R 3 Compound e=isopropyl, etc., but is not limited thereto.
Meanwhile, the diol-based compound and the ionic liquid catalyst may be added to the mixed solution and stirred at 20 to 100 ℃, or 50 to 100 ℃, or 60 to 100 ℃, or 70 to 90 ℃ for 1 to 24 hours, or 1 to 12 hours, or 1 to 8 hours.
Specifically, the conditions are mild process conditions relative to conventional pressure/high temperature processes, and by stirring under the above conditions, the process can be performed in a mild process compared to the pressure/high temperature process. In particular, when stirred at 70 ℃ to 90 ℃ for 1 hour to 12 hours, there is an advantage in that the most efficient results are obtained in terms of reproducibility and acceptability.
Meanwhile, the step of obtaining the aromatic diol compound formed in the stirring step may include injecting the product obtained in the stirring step into a crystallization solvent to form an aromatic diol compound crystal; filtering the aromatic diol compound crystals. The specific equipment and conditions for adding the crystallization solvent and forming the aromatic diol compound crystal are not limited, and can be applied without limitation to various recrystallization processes that have been widely used in the technical field of recovering conventional aromatic diol compounds (bisphenol a). As an example of the crystallization solvent, water may be used.
Further, in the step of filtering the aromatic diol compound crystals, specific filtering equipment and conditions are not limited, and conventionally, various filtering processes which have been widely used in the technical field of recovering aromatic diol compounds (bisphenol a) can be applied without limitation. As an example of the filtration, filtration under reduced pressure may be used.
3. Regenerated plastic
According to another embodiment of the present invention, a recycled plastic comprising the reaction product of the monomer composition for synthesizing a recycled plastic of one embodiment and a comonomer may be provided.
Details of the monomer composition for synthesizing recycled plastic of one embodiment include all of those described above in the one embodiment and the other embodiment.
Examples corresponding to the recycled plastic are not particularly limited, and various plastics synthesized from an aromatic diol compound (e.g., bisphenol a) and a carbonate precursor (e.g., dimethyl carbonate, diethyl carbonate, or ethyl methyl carbonate) as monomers may be applied without limitation, and more specific examples may be polycarbonate-based resins.
Polycarbonate-based resin means to include both homopolymers and copolymers comprising polycarbonate repeating units, and is collectively referred to as a reaction product obtained by polymerization or copolymerization of monomers comprising an aromatic diol compound and a carbonate precursor. When it contains one carbonate repeating unit obtained by using only one aromatic diol compound and one carbonate precursor, a homopolymer can be synthesized. Further, when one aromatic diol compound and two or more carbonate precursors are used as monomers, or two or more aromatic diol compounds and one carbonate precursor are used, or one or more other diols are used in addition to the one aromatic diol compound and the one carbonate precursor to thereby contain two or more carbonates, a copolymer may be synthesized. The homopolymer or copolymer may include all of low molecular compounds, oligomers, and polymers depending on the molecular weight range.
More specifically, in a recycled plastic comprising the reaction product of the monomer composition for synthesizing a recycled plastic and a comonomer of one embodiment, a carbonate precursor may be used as the comonomer. Specific examples of carbonate precursors include phosgene, triphosgene, diphosgene, bromophosgene, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, diphenyl carbonate, xylene carbonate, bis (chlorophenyl) carbonate, m-toluene carbonate, dinaphthyl carbonate, bis (diphenyl) carbonate, or dihaloformate.
Examples of the reaction process for synthesizing the monomer composition of the recycled plastic and the comonomer of the polycarbonate-based resin are not particularly limited, and various known methods for preparing polycarbonate may be applied without limitation.
However, in one example of the polycarbonate production method, a polycarbonate production method including the steps of: a composition comprising a monomer composition for synthesizing recycled plastic and a comonomer is polymerized. At this time, the polymerization may be performed by interfacial polymerization, and during the interfacial polymerization, the polymerization reaction may be performed at normal pressure and low temperature, and the molecular weight may be easily controlled.
The polymerization temperature may be 0 ℃ to 40 ℃ and the reaction time may be 10 minutes to 5 hours. In addition, the pH during the reaction may be maintained at 9 or more or 11 or more.
The solvent that can be used for polymerization is not particularly limited as long as it is a solvent used in the art for polymerization of polycarbonate, and as one example, halogenated hydrocarbons such as methylene chloride and chlorobenzene can be used.
In addition, the polymerization may be carried out in the presence of an acid-binding agent. As the acid-binding agent, an alkali metal hydroxide (e.g., sodium hydroxide or potassium hydroxide) or an amine compound (e.g., pyridine) can be used.
In addition, in order to adjust the molecular weight of the polycarbonate during the polymerization, the polymerization may be carried out in the presence of a molecular weight regulator. Alkylphenols having 1 to 20 carbon atoms may be used as the molecular weight regulator, and specific examples thereof include p-tert-butylphenol, p-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, hexadecylphenol, octadecylphenol, eicosylphenol, docosylphenol or triacontylphenol. The molecular weight regulator may be added before, during or after the initiation of the polymerization. The molecular weight modifier may be used in an amount of 0.01 to 10 parts by weight or 0.1 to 6 parts by weight based on 100 parts by weight of the aromatic diol compound, and a desired molecular weight may be obtained within this range.
In addition, in order to promote the polymerization reaction, a reaction accelerator such as a tertiary amine compound, a quaternary ammonium compound, or a quaternary ammonium compound may be usedCompounds, including triethylamine, tetra-n-butylammonium bromide, or tetra-n-butylammonium bromide +.>
4. Molded product
According to still another embodiment of the present invention, there may be provided a molded article comprising the recycled plastic of the other embodiment. Details of recycled plastic include all those described above in other embodiments.
The molded article can be obtained by applying the reclaimed plastic to various known plastic molding methods without limitation. As an example of the molding method, injection molding, foam injection molding, blow molding, or extrusion molding may be mentioned.
Examples of the molded article are not particularly limited, and may be applied to various molded articles using plastics without limitation. Examples of molded articles include automobiles, electric and electronic products, communication products, commodities, construction materials, optical parts, exterior materials, and the like.
If necessary, the molded article may contain one or more additives selected from the following in addition to the recycled plastic of other embodiments: antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact enhancers, optical brighteners, ultraviolet absorbers, pigments, and dyes.
An example of a method of manufacturing a molded article may include the steps of: the recycled plastic and the additive of the other embodiment are thoroughly mixed using a mixer, the mixture is extrusion molded with an extruder to produce pellets, the pellets are dried, and then they are injected with an injection molding machine.
Advantageous effects
According to the present invention, there can be provided a monomer composition for synthesizing a recycled plastic comprising a high-purity aromatic diol compound recovered by recycling through chemical decomposition of a polycarbonate-based resin, a method for producing the same, and a recycled plastic and a molded product using the same.
Detailed Description
The present invention will be described in more detail with reference to the following examples. However, these examples are for illustrative purposes only, and the scope of the present invention is not limited thereto.
< examples: preparation of regenerated bisphenol A monomer composition
Examples 1 to 7
80g of methylene chloride and 30g of polycarbonate were added to a 250ml three-necked flask and then stirred.
Then, 22g of ethylene glycol and the catalyst listed in the following table 1 were added thereto, and stirred at the reaction temperature shown in the following table 1 for 24 hours.
When the reaction is completed, the reaction product is added to water, and the crystallized bisphenol a is filtered under reduced pressure to obtain bisphenol a, thereby preparing a regenerated bisphenol a monomer composition.
TABLE 1
| Category(s) | Catalyst | Catalyst addition (g) | Reaction temperature (. Degree. C.) |
| Example 1 | Compound a | 0.3 | 70 |
| Example 2 | Compound b | 0.3 | 70 |
| Example 3 | Compound c | 0.3 | 70 |
| Example 4 | Compound d | 0.3 | 70 |
| Example 5 | Compound e | 0.3 | 70 |
| Example 6 | Compound a | 0.3 | 80 |
| Example 7 | Compound a | 0.3 | 90 |
-compound a: in the following chemical formula A, R 1 ＝R 2 ＝R 3 =hydrogen (H), 0.6g imidazole and 1.5g 1, 8-diazabicyclo (5, 4, 0) decaThe mono-carbon-7-ene was added to a 20ml vial and stirred at room temperature for 5 hours to obtain compound a.
-compound b: in the following chemical formula A, R 1 ＝R 3 =hydrogen (H) and R 2 =methyl (CH) 3 )。
0.8g of 2-methyl-1H-imidazole and 1.5g of 1, 8-diazabicyclo (5, 4, 0) undec-7-ene were added to a 20ml vial and stirred at room temperature for 5 hours to obtain compound b.
-compound c: in the following chemical formula A, R 1 ＝R 2 =hydrogen (H) and R 3 =methyl (CH) 3 )。
0.8g of 4-methyl-1H-imidazole and 1.5g of 1, 8-diazabicyclo (5, 4, 0) undec-7-ene were added to a 20ml vial and stirred at room temperature for 5 hours to obtain compound c.
-compound d: in the following chemical formula A, R 1 ＝R 3 =hydrogen (H) and R 2 =isopropyl.
1.1g of 2-isopropyl-1H-imidazole and 1.5g of 1, 8-diazabicyclo (5, 4, 0) undec-7-ene were added to a 20ml vial and stirred at room temperature for 5 hours to obtain compound d.
-compound e: in formula A, R 1 ＝R 2 =hydrogen (H) and R 3 =isopropyl.
1.1g of 4-isopropyl-1H-imidazole and 1.5g of 1, 8-diazabicyclo (5, 4, 0) undec-7-ene were added to a 20ml vial and stirred at room temperature for 5 hours to obtain compound e.
[ chemical formula A ]
Comparative example: preparation of regenerated bisphenol A monomer composition
Comparative example 1
20g of polycarbonate was added to a 250ml three-necked flask and stirred.
Then, 22g of ethylene glycol and 0.3g of compound a as a catalyst were added thereto, and stirred at 130℃for 24 hours.
When the reaction is completed, the reaction product is added to water, and the crystallized bisphenol a is filtered under reduced pressure to obtain bisphenol a, thereby preparing a regenerated bisphenol a monomer composition.
Comparative example 2
60ml of methylene chloride, 30ml of methanol and 1.5g of compound a as a catalyst were added to a 250ml three-necked flask and stirred.
Then, 30g of waste polycarbonate was added thereto, and stirred at 40℃for 5 hours.
When the reaction is completed, the reaction product is added to water, and the crystallized bisphenol a is filtered under reduced pressure to obtain bisphenol a, thereby preparing a regenerated bisphenol a monomer composition.
Comparative example 3
60ml of methylene chloride, 30ml of ethanol and 1.5g of compound a as a catalyst were added to a 250ml three-necked flask and stirred.
Then, 30g of waste polycarbonate was added thereto, and stirred at 50℃for 24 hours.
When the reaction is completed, the reaction product is added to water, and the crystallized bisphenol a is filtered under reduced pressure to obtain bisphenol a, thereby preparing a regenerated bisphenol a monomer composition.
< Experimental example >
Physical properties of the regenerated bisphenol a monomer compositions or byproducts obtained in examples and comparative examples were measured by the following methods, and the results are shown in table 2 below.
Purity of BPA
1% by weight of the regenerated bisphenol A monomer composition was dissolved in Acetonitrile (ACN) solvent at normal pressure and 20℃to 30℃and then analyzed for purity of bisphenol A (BPA) by a Waters HPLC system (e 2695 separation module, 2998PDA detector) using UG120 (4.6 mm I.DX 50 mm).
< HPLC Condition >
(1) Column: UG120 (4.6 mm I.DX 50 mm)
(2) Column temperature: 40 DEG C
(3) Injection volume: 10 μl of
(4) Flow rate: THF: ACN: water=15:15:70, volume=1.23 ml/min (total=10 min)
(5) A detector: 245nm
2. Color coordinates (L, a, and b)
The color coordinates of the regenerated bisphenol a monomer composition were analyzed in reflectance mode using a HunterLab UltraSACN PRO spectrophotometer.
Ratios of impurities of BPA derivatives (MHE-BPA, BHE-BPA)
1ml of the regenerated bisphenol A monomer composition was taken as a sample and High Performance Liquid Chromatography (HPLC) analysis was performed in the same manner as in the 1.BPA purity measurement method, and the peak area ratio (unit:%) of the BPA derivative (monohydroxy-bisphenol A [ MHE-BPA ] and dihydroxyethyl-bisphenol A [ BHE-BPA ]) impurities with respect to 100% of the total HPLC peak area was measured according to the following equation 1:
[ equation 1]
Ratio (%) = (peak area of aromatic diol compound derivative in HPLC/total peak area in HPLC) ×100 of aromatic diol compound derivative impurities.
In equation 1, the peak of the bisphenol a derivative in HPLC is specifically as follows, and in equation 1, the peak area of the bisphenol a derivative in HPLC is the total peak area of MHE-BPA and BHE-BPA.
Monohydroxyethyl-bisphenol a [ MHE-BPA ]: peak at retention time of 2.84 min
Bis-hydroxyethyl-bisphenol a [ BHE-BPA ]: peak at retention time of 2.61 min
TABLE 2
Measurement results of experimental examples
As shown in table 1, the regenerated bisphenol a monomer compositions obtained in examples 1 to 7 exhibited high purity of 99.3% to 99.8%. In addition, the regenerated bisphenol a monomer compositions obtained in examples 1 to 7 exhibited color coordinates L of 95.77 to 97.49, a of 0.10 to 0.23, and b of 0.58 to 1.11, showing excellent optical characteristics. Further, in the regenerated bisphenol a monomer compositions obtained in examples 1 to 7, the ratio of BPA derivative impurities was measured as low as 0.08% to 0.13%.
On the other hand, the purity of the regenerated bisphenol a monomer composition obtained in comparative example 1 was 77.9%, which was reduced relative to the purity of the regenerated bisphenol a monomer composition of the example, and the ratio of BPA derivative impurities was measured to be 19.92%, which was higher than that of the example.
In addition, the regenerated bisphenol a monomer compositions obtained in comparative examples 2 to 3 have color coordinates L of 91.73 to 92.36, a of 1.98 to 2.12, and b of 2.98 to 3.16, showing poor optical characteristics compared with examples.
Claims (20)
1. A monomer composition for synthesizing regenerated plastics,
the monomer composition for synthesizing recycled plastic comprises an aromatic diol compound,
wherein the ratio of the impurity of the aromatic diol compound derivative according to the following equation 1 is 0.5% or less,
wherein the aromatic diol compound has a purity of 99.25% or more, and
wherein the monomer composition for synthesizing recycled plastic is recovered from a polycarbonate-based resin:
[ equation 1]
Ratio (%) = (peak area of the aromatic diol compound derivative in HPLC/total peak area in HPLC) ×100 of aromatic diol compound derivative impurities.
2. The monomer composition for synthesizing recycled plastic according to claim 1, wherein:
In equation 1, the peak area of the aromatic diol compound derivative in HPLC is the total peak area of each of the one or more aromatic diol compound derivatives.
3. The monomer composition for synthesizing recycled plastic according to claim 1, wherein:
the derivative of the aromatic diol compound includes one or more compounds selected from the group consisting of monohydroxy-bisphenol a and bishydroxy-ethyl-bisphenol a.
4. The monomer composition for synthesizing recycled plastic according to claim 1, wherein:
the monomer composition for synthesizing recycled plastic has a color coordinate L of 94 to 99.
5. The monomer composition for synthesizing recycled plastic according to claim 1, wherein:
the monomer composition for synthesizing recycled plastic has a color coordinate b of 0.01 to 2.
6. The monomer composition for synthesizing recycled plastic according to claim 1, wherein:
the monomer composition for synthesizing recycled plastic has a color coordinate a of 0.01 to 1.5.
7. The monomer composition for synthesizing recycled plastic according to claim 1, wherein:
the aromatic diol compound is recovered from the polycarbonate-based resin for recovering the monomer composition for synthesizing recycled plastic.
8. A process for preparing the monomer composition for synthesizing recycled plastic according to claim 1, comprising the steps of:
adding polycarbonate to an organic solvent to prepare a mixed solution;
adding a glycol-based compound and an ionic liquid catalyst to the mixed solution and stirring them; and
obtaining the aromatic diol compound formed in the stirring step.
9. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
the diol-based compound comprises an alkylene diol.
10. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
the organic solvent includes one or more solvents selected from the group consisting of: tetrahydrofuran, toluene, methylene chloride, chloroform, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate and dipropyl carbonate.
11. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
the weight ratio between the organic solvent and the glycol-based compound is 10:1 to 1:10.
12. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
The ionic liquid catalyst is added in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of polycarbonate.
13. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
the ionic liquid catalyst comprises an amidine-based salt compound.
14. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 13, wherein:
the amidine-based salt compound comprises an amidine-based cation having a fused ring.
15. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 14, wherein:
the fused rings include fused rings of 7-membered rings and 6-membered rings.
16. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 13, wherein:
the amidine-based salt compounds include salt compounds represented by the following chemical formula a:
[ chemical formula A ]
Wherein in formula A, R 1 、R 2 And R is 3 Are the same or different from each other and are each independently hydrogen or alkyl.
17. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
the diol-based compound and the ionic liquid catalyst are added to the mixed solution and stirred at 20 to 100 ℃ for 1 to 30 hours.
18. The method for preparing a monomer composition for synthesizing recycled plastic according to claim 8, wherein:
obtaining the aromatic diol compound formed in the agitating step includes,
injecting the product obtained in the stirring step into a crystallization solvent to form aromatic diol compound crystals; and
the aromatic diol compound crystals are filtered.
19. A recycled plastic comprising the reaction product of the monomer composition for synthesizing recycled plastic of claim 1 and a comonomer.
20. A molded product comprising the recycled plastic of claim 19.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2022-0045959 | 2022-04-13 | ||
| KR10-2023-0044307 | 2023-04-04 | ||
| KR1020230044307A KR20230146991A (en) | 2022-04-13 | 2023-04-04 | Monomer composition for synthesising recycled plastic, prepration method thereof, and recycled plastic, molded product using the same |
| PCT/KR2023/004929 WO2023200244A1 (en) | 2022-04-13 | 2023-04-12 | Monomer composition for synthesizing recycled plastics, method for manufacturing same, and recycled plastics and molded articles using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117794991A true CN117794991A (en) | 2024-03-29 |
Family
ID=90402140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202380013113.2A Pending CN117794991A (en) | 2022-04-13 | 2023-04-12 | Monomer composition for synthesizing recycled plastic, method for preparing the same, recycled plastic using the same, and molded product |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117794991A (en) |
-
2023
- 2023-04-12 CN CN202380013113.2A patent/CN117794991A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2024528896A (en) | Monomer composition for synthesizing recycled plastics, its manufacturing method, recycled plastics using the same, and molded articles | |
| US20240218149A1 (en) | Monomer composition for synthesizing recycled plastic, prepration method thereof, and recycled plastic, molded product using the same | |
| CN117794991A (en) | Monomer composition for synthesizing recycled plastic, method for preparing the same, recycled plastic using the same, and molded product | |
| CN117642457A (en) | Monomer composition for synthetic recycled plastic, method for preparing the same, and recycled plastic and molded product using the same | |
| CN117651733A (en) | Monomer composition for synthetic recycled plastic, method for preparing the same, and recycled plastic and molded product using the same | |
| KR20230039099A (en) | Monomer composition for synthesising recycled plastic, prepration method thereof, and recycled plastic, molded product using the same | |
| KR20230146991A (en) | Monomer composition for synthesising recycled plastic, prepration method thereof, and recycled plastic, molded product using the same | |
| EP4345126A1 (en) | Monomer composition for synthesizing recycled plastic, method for manufacturing same, and recycled plastic and molded product using same | |
| TWI832332B (en) | Monomer composition for synthesizing recycled plastic, prepration method thereof, and recycled plastic, molded product using the same | |
| EP4400531A1 (en) | Monomer composition for synthesizing recycled plastic, method for preparing same, and recycled plastic and molded articles using same | |
| EP4234608A1 (en) | Polycarbonate copolymer | |
| CN118355054A (en) | Monomer composition for synthesizing recycled plastic, method for preparing the same, and recycled plastic and molded article using the same | |
| KR20140097919A (en) | Method for preparing polycarbonate resin | |
| KR102625057B1 (en) | Diol compound, polycarbonate and method for preparing the same | |
| KR20230052755A (en) | Monomer composition for synthesising recycled plastic, prepration method thereof, and recycled plastic, molded product using the same | |
| CN117916287A (en) | Resin and method for producing same | |
| KR20230039102A (en) | Monomer composition for synthesising recycled plastic, prepration method thereof, and recycled plastic, molded product using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |