WO2005092963A1 - Recycled method for a wasted polymer which is mixed polyester polyamide and reclaimed materials thereof - Google Patents
Recycled method for a wasted polymer which is mixed polyester polyamide and reclaimed materials thereof Download PDFInfo
- Publication number
- WO2005092963A1 WO2005092963A1 PCT/KR2005/000851 KR2005000851W WO2005092963A1 WO 2005092963 A1 WO2005092963 A1 WO 2005092963A1 KR 2005000851 W KR2005000851 W KR 2005000851W WO 2005092963 A1 WO2005092963 A1 WO 2005092963A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyester
- acid
- resin
- block polymer
- amide
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 92
- 239000004952 Polyamide Substances 0.000 title claims abstract description 44
- 229920002647 polyamide Polymers 0.000 title claims abstract description 44
- 229920000728 polyester Polymers 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 title claims abstract description 24
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims abstract description 177
- 229920005989 resin Polymers 0.000 claims abstract description 97
- 239000011347 resin Substances 0.000 claims abstract description 97
- 239000010812 mixed waste Substances 0.000 claims abstract description 86
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 64
- 239000007787 solid Substances 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 43
- 238000004064 recycling Methods 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 150000007514 bases Chemical class 0.000 claims abstract description 18
- 239000011230 binding agent Substances 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 15
- 239000003822 epoxy resin Substances 0.000 claims abstract description 14
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 14
- 239000003607 modifier Substances 0.000 claims abstract description 10
- 239000003973 paint Substances 0.000 claims abstract description 10
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 10
- 238000004513 sizing Methods 0.000 claims abstract description 10
- 239000000853 adhesive Substances 0.000 claims abstract description 9
- 230000001070 adhesive effect Effects 0.000 claims abstract description 9
- 239000000835 fiber Substances 0.000 claims abstract description 8
- 239000003094 microcapsule Substances 0.000 claims abstract description 8
- 239000000843 powder Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000010419 fine particle Substances 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 239000013054 paper strength agent Substances 0.000 claims abstract description 7
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 7
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 7
- 239000000057 synthetic resin Substances 0.000 claims abstract description 7
- 238000000227 grinding Methods 0.000 claims abstract description 6
- 238000012545 processing Methods 0.000 claims abstract description 6
- 238000004065 wastewater treatment Methods 0.000 claims abstract description 6
- 239000004831 Hot glue Substances 0.000 claims abstract description 5
- 239000003463 adsorbent Substances 0.000 claims abstract description 5
- 239000004568 cement Substances 0.000 claims abstract description 5
- 239000011248 coating agent Substances 0.000 claims abstract description 5
- 238000000576 coating method Methods 0.000 claims abstract description 5
- 239000002270 dispersing agent Substances 0.000 claims abstract description 3
- 238000004078 waterproofing Methods 0.000 claims abstract 3
- 239000000243 solution Substances 0.000 claims description 50
- 239000000047 product Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 150000005846 sugar alcohols Polymers 0.000 claims description 40
- 150000007519 polyprotic acids Polymers 0.000 claims description 33
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 31
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 29
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 17
- 239000000194 fatty acid Substances 0.000 claims description 17
- 229930195729 fatty acid Natural products 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 16
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 16
- 229920000180 alkyd Polymers 0.000 claims description 15
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 15
- 238000006068 polycondensation reaction Methods 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 12
- 239000012046 mixed solvent Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- 239000000976 ink Substances 0.000 claims description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 9
- 239000011976 maleic acid Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000001361 adipic acid Substances 0.000 claims description 8
- 235000011037 adipic acid Nutrition 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 8
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- KYXHKHDZJSDWEF-LHLOQNFPSA-N CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 Chemical compound CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 KYXHKHDZJSDWEF-LHLOQNFPSA-N 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 5
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 claims description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 239000002023 wood Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 4
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 4
- 240000000972 Agathis dammara Species 0.000 claims description 4
- 239000004859 Copal Substances 0.000 claims description 4
- 229920002871 Dammar gum Polymers 0.000 claims description 4
- 241000782205 Guibourtia conjugata Species 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229940113088 dimethylacetamide Drugs 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 2
- 238000012691 depolymerization reaction Methods 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229920006305 unsaturated polyester Polymers 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract description 2
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 description 19
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000003472 neutralizing effect Effects 0.000 description 7
- 229920001778 nylon Polymers 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000004677 Nylon Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- PQILDPDMXBRMHP-UHFFFAOYSA-N 2,9,11,18-tetraoxa-1,10-diazabicyclo[8.8.6]tetracosane-3,8,12,17-tetrone Chemical compound C1(CCCCC(=O)ON2CCCCCCN(O1)OC(CCCCC(=O)O2)=O)=O PQILDPDMXBRMHP-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
-
- 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
Definitions
- the present invention relates to a process for preparing a polyester-amide resin composition capable of being used as a new material, and having polyester blocks and polyamide blocks in a molecular structure of a polymer produced by recycling a mixed waste of polyester and polyamide (hereinafter, referred to as "mixed waste") such as polyester and polyamide mixed-fiber waste, waste plastic bottles and waste composite molded articles, in which polyesters including polyethylene terephthalate and polyamides are mixed and thus are inseparable from one another Background Art
- mixed waste such as polyester and polyamide mixed-fiber waste, waste plastic bottles and waste composite molded articles
- the present invention is disclosed in the following embodiments: (1) depolymerization embodiment utilizing solid resins, (2) depolymerization embodiment utilizing polyhydric alcohols, (3) depolymerization embodiment utilizing polyhydric alcohols in conjunction with solid resins, (4) depolymerization embodiment utilizing oligomers, and (5) depolymerization embodiment utilizing monoglycerides of fatty acids and mono polyhydric alcoholides of fatty acids.
- a recycling method of a mixed waste comprising:
- a recycling method of a mixed waste comprising:
- a monomer and waste polyamide producing polyamide may be additionally added and reacted to produce a polyamide block.
- the monomer and waste polyamide are added in content of 1 to 90% by weight to the prepared polymer.
- the polyester-amide resin obtained according to the recycling method of the present invention exhibits superior compatibility, dispersibility, solubility and adhesiveness.
- the polyester-amide block polymer recycled according to the present invention can be used as an industrially useful material such as synthetic resin fine particles, microcapsules, adsorbents, polymerization toner binders for electron photography, fiber processing agents, sizing agents for paper-making and paper strength agents, wastewater treatment agents, cement admixtures, inkjet ink binders, epoxy resin curing agents and modifiers, water-dispersible epoxy resin curing agents and modifiers, printer ink, paints, powder paints, adhesives, hot melt adhesives, binders for toners manufactured by grinding methods, waterproof agents, crosslinking curable unsaturated polyester-amide resins, and polyurethane resins.
- synthetic resin fine particles, microcapsules, adsorbents, polymerization toner binders for electron photography fiber processing agents, sizing agents for paper-making and paper strength agents, wastewater treatment agents, cement admixtures, inkjet ink binders, epoxy resin curing agents and modifiers, water-dispersible epoxy resin curing agents and
- the recycling method of the mixed waste in accordance with a first embodiment of the present invention comprises:
- Step (a) is a step of depolymerizing the collected mixed waste. That is, the mixed waste is physically ground, melted under an inert gas atmosphere such as nitrogen, and reacted with a solid resin dissolving agent, thereby performing first depolymerization.
- Components, abietic acid, pimaric acid or composite resin acid, having reactive functional groups such as conjugated bonds in the molecular structure of the solid resin dissolving agent react with ester bonds and amide bonds in the mixed waste to cleave the backbone chain, resulting in depolymerization of the mixed waste thus leading to lowered molecular weight.
- solid resin dissolving agent examples include, but are not limited to, gum rosin, wood rosin, tall rosin, hydrogenated rosin, maleated rosin, rosin ester, pinene resin, dipentene resin, C5 petroleum resin, C9 petroleum resin, dammar resin, copal resin, DCPD resin, hydrogenated DCPD resin, maleated styrene resin and any combination thereof.
- a mixing ratio of the solid resin dissolving agent : mixed waste is in the range of 1:10 to 10:1, on the basis of weight ratio.
- a mixing ratio of less than 1:10 may result in inferior depolymerization of the mixed waste.
- the mixing ratio is greater than 10:1, this may cause problems such as inferior heat resistance and mechanical properties.
- the depolymerization product is reacted with a polybasic acid to further progress second depolymerization and addition reaction (Diels- Alder Reaction).
- a polybasic acid that can be used in the present invention include, but are not limited to, anhydrous phthalic acid, isophthalic acid, terephthalic acid, adipic acid, azelaic acid, sebacic acid, anhydrous tetrahydrophthalic acid, anhydrous maleic acid, fumaric acid, itaconic acid, trimellitic acid, anhydrous trimellitic acid, anhydrous pyromellitic acid, succinic acid, cyclohexane dicarboxylic acid, naphthalene dicarboxylic acid, dimeric acid, C6-C25 fatty acid and any combination thereof.
- the polybasic acid is used in an amount of 1 to 70% by weight, based on the weight of the first depolymerization product. If the amount of the polybasic acid is less than 1% by weight, this may lead to production of high melting point polymer, thereby presenting poor modification problems. Whereas, if the amount of the polybasic acid exceeds 70% by weight, this may lead to consumption of a great deal of polyhydric alcohol which is thus disadvantageous from an economic point of view.
- Step (b) consists of polycondensing the depolymerized product of step (a) with the polyhydric alcohol to control an acid value and to increase molecular weight.
- polyhydric alcohol examples include, but are not limited to, ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, alkylene oxide adduct of bisphenol A, trimethylol propane, glycerin, pentaerythritol, monoglycerides of fatty acids and mono polyhydric alcoholides of fatty acids, and any combination thereof.
- the amount of the polyhydric alcohol to be used is in the range of 1 to 70% by weight, based on the weight of the product depolymerized in step (a). Where the amount of the polyhydric alcohol is less than 1% by weight, this may cause poor modification due to production of a high melting point polymer. In contrast, where the amount of the polyhydric alcohol is greater than 70% by weight, this may lead to production of a high molecular weight polymer, thus presenting problems associated with poor water-solubility or poor water-dispersibility.
- additional monomer and waste polyamide p roducing a polyamide may be added and reacted to produce polyamide blocks.
- the monomer and waste polyamide is added in the content of 1 to 90% by weight relative to the prepared polymer.
- Polyamide-producing monomer and waste polyamide that can be used in step (b) are at least one of waste materials selected from the group consisting of lactams containing more than 6 carbon atoms such as epsilon-caprolactam and lauryl lactam; aliphatic amino carboxylic acids such as amino caproic acid, 7-aminoheptanoic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid; polycondensation products of diacid and diamine such as hexamethylenediamine diadipate; and waste polyamides such as 6-nylon, 6,6-nylon, 11 -nylon, and 12-nylon.
- lactams containing more than 6 carbon atoms such as epsilon-caprolactam and lauryl lactam
- aliphatic amino carboxylic acids such as amino caproic acid, 7-aminoheptanoic acid, 11-aminoundecanoic acid,
- the acid value of the polyester-amide thus obtained is preferably adjusted to the range of 1 to 150 mgKOH/ g. If the acid value is less than 1 mgKOH/g, this may lead to problems such as poor water-solubility and water-dispersibility. Whereas, if the acid value is greater than 150 mgKOH/g, this may lead to problems associated with adhesiveness, chemical properties and electrical properties.
- steps (a) and (b) are all progressed at solid phase of melt state. It is preferred to progress the reactions in the presence of a reaction catalyst, for example 0.05 to 0.5% by weight of dibutyltin oxide (DBTO), based on the total weight of reactants, from the stand point of acceleration of reaction rate.
- steps (a) and (b) are preferably carried out in the range of 200 to 250°C. Where the reaction temperature is below 200°C, this may present problems such as delayed reaction rate and production of low molecular weight polymers. In contrast, where the reaction temperature is above 250°C, this may present problems such as oxidative reactions and production of high molecular weight polymers.
- the polyester-amide polymer obtained in step (b) has a weight average molecular weight of 3,000 to 50,000 and a softening point of 10 to 150°C, and polyamide blocks are controlled to be contained in the amount of 1 to 90% by weight in the molecular structure of the resulting polymer.
- the acid value of the thus-obtained polyester-amide block polymer is greater than 20 mgKOH/g, it is possible to not only recover the polyester-amide block polymer in solid form, but also to recover it in the form of a solution where the polymer is dissolved in water, a hydrophilic solvent or a mixed solvent thereof, due to water- solubility suited for desired use and application.
- the acid value of the polyester-amide polymer is less than 20 mgKOH/g, it is not possible to recover the polyester-amide block polymer in the form of an aqueous solution due to difficulty to obtain sufficient solubility, and thus it is preferred to recover the polymer in solid form for use as a solid state or after dissolving in a suitable solvent, depending upon desired use.
- the solution is preferably prepared according to the following steps.
- the polyester-amide block polymer obtained in step (b), having an acid value of more than 20 mgKOH/g is reacted with a basic compound to obtain a neutralized salt of the polyester-amide block polymer.
- a basic compound to obtain a neutralized salt of the polyester-amide block polymer.
- carboxyl groups present in the polyester-amide polymer are converted into their corresponding neutralized salt structures, thereby increasing water-solubility.
- Specific examples of the basic compound that can be used in the present invention include, but are not limited to, sodium hydroxide, potassium hydroxide, ammonium hydroxide, lithium hydroxide, organic amines and any combination thereof.
- the amount of the basic compound to be used is preferably in the range of 3 to 30% by weight, based on the weight of the polyester-amide polymer.
- the amount of the basic compound is less than 3% by weight, this may raise problems such as poor water-solubility or poor water-dispersibility. In contrast, if the amount of the basic compound is greater than 30% by weight, this may lead to problems associated with adhesiveness, chemical properties, and electrical properties.
- an aqueous polyester solution or a polyester organic solution can be obtained.
- the hydrophilic solvent that can be used in the present invention include, but are not limited to, alcohols, ethers, acetone, diacetone alcohol, dimethyl formamide and dimethyl acetamide, tetrahydrofuran, ethyl cellosolve, propyl cellosolve, butyl cellosolve, N- methyl-2-pyrollidone and any combination thereof.
- water, the hydrophilic solvent, or a mixed solvent thereof is used in 1 to 10-times the amount of the weight of the neutralized polyester-amide polymer. If the amount of the solvent to be used is less than 1 times the amount of the weight of the neutralized polyester-amide polymer, this may result in poor workability. In contrast, if the amount of the solvent is greater than 10 times the amount of the weight of the neutralized polyester-amide block polymer, the resulting solution is excessively diluted, thus presenting problems associated with adhesiveness and efficiency.
- the mixed waste is depolymerized by reacting with a polyhydric alcohol. Hydroxyl groups of the polyhydric alcohol react with ester bonds in the mixed waste to cleave the backbone chain, thereby depolymerizing the mixed waste leading to decreased molecular weight thereof.
- polyhydric alcohol examples include, but are not limited to, ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, alkylene oxide adduct of bisphenol A, trimethylol propane, glycerin, pen- taerythritol, monoglycerides of fatty acids and mono polyhydric alcoholides of fatty acids, and any combination thereof.
- the depolymerized product is reacted with a polybasic acid, and the reaction product is polycondensed with a polyhydric alcohol to obtain a polyester-amide polymer containing 2 or 3 carboxyl groups at chain ends thereof and having an acid value of 1 to 150 mgKOH/g.
- the polybasic acid is used in an amount of 1 to 50% by weight, based on the weight of the depolymerization product obtained in the previous step. If the amount of the polybasic acid to be used is less than 1% by weight, this may lead to production of a high melting point polymer, thereby presenting poor modification problems. In contrast, if the amount of the polybasic acid exceeds 50% by weight, this may lead to consumption of a great deal of polyhydric alcohol which is thus disadvantageous from an economic point of view.
- the polyester-amide polymer is reacted with a basic compound to obtain a neutralized salt of the polyester-amide polymer having increased solubility in water or hydrophilic organic solvents.
- Specific examples of the basic compound that can be used in the recycling method in accordance with the second embodiment of the present invention include, but are not limited to, sodium hydroxide, potassium hydroxide, ammonium hydroxide, lithium hydroxide, organic amines and any combination thereof.
- the amount of the basic compound to be used is preferably in the range of 1 to 30% by weight, based on the weight of the polyester-amide polymer. If the amount of the basic compound is less than 1% by weight, this may raise problems such as insufficient solubility in water or mixed solvents of the hydrophilic organic solvent and water. In contrast, if the amount of the basic compound is greater than 30% by weight, this may lead to problems associated with poor adhesiveness, poor chemical properties, and poor electrical properties.
- the neutralized salt of the polyester-amide polymer is dispersed in water, the hydrophilic solvent, or the mixed solvent thereof, to obtain the mixed waste in the form of water-soluble and water-dispersible polyester-amide solutions as final products.
- the hydrophilic solvent that can be used in the recycling method in accordance with the second embodiment of the present invention include, but are not limited to, alcohols, acetone, diacetone alcohol, dimethyl formamide, dimethyl acetamide, ethyl cellosolve, propyl cellosolve, butyl cellosolve, tetrahydrofuran, N- methyl-2-pyrollidone and any combination thereof.
- the hydrophilic solvent is used in an amount of 1 to 100% by weight, based on the weight of the neutralized salt of the polyester-amide polymer.
- Use of less than 1% by weight of the hydrophilic solvent results in poor solubility.
- the amount of the hydrophilic solvent exceeds 100% by weight, it is disadvantageous from environmental and economic points of view.
- the product, obtained by depolymerizing the mixed waste using the second embodiment of the present invention is reacted with the polybasic acid and polyhydric alcohol to prepare a polyesteramide polyol having an acid value of 1 to 10 mgKOH/g and hydroxyl value of 5-200 mgKoH/g which is then reacted with diisocyanate to obtain a polyurethane resin.
- an ethylenic vinyl monomer containing a polymerization inhibitor may be dissolved in the polyester-amide block polymer to obtain a crosslinking curable unsaturated polyester amide resin.
- the mixed waste is reacted with a polyhydric alcohol to obtain a polyester-amide depolymerization product.
- the polyester-amide depolymerization product is reacted with a depoly- merization-stabilizing solid resin to obtain a polyester-amide depolymerization product stabilized via the transesterification reaction.
- the depolymerization-stabilizing solid resin has properties to control the degree of polymerization and thus can stabilize the polyester-amide depolymerization product against reversible reaction.
- depolymerization-stabilizing solid resin examples include, but are not limited to, gum rosin, wood rosin, tall rosin, hydrogenated rosin, maleated rosin, rosin ester, pinene resin, dipentene resin, C5 petroleum resin, C9 petroleum resin, dammar resin, copal resin, DCPD resin, hydrogenated DCPD resin, maleated styrene resin and any combination thereof.
- the depolymerization-stabilizing solid resin is preferably used in an amount of 1 to 100% by weight based on the weight of the depolymerization product.
- the amount of the stabilizing solid resin is less than 1% by weight, this may cause problems associated with control of intrinsic viscosity and the degree of polymerization. In contrast, where the amount of the stabilizing solid resin exceeds 100% by weight, this may incur problems associated with heat resistance and mechanical properties.
- the depolymerization product is polycondensed with a polybasic acid, dimethyl 5-sodium sulfoisophthalate (DMSSIP), or a mixture thereof.
- DMSSIP dimethyl 5-sodium sulfoisophthalate
- specific examples and amounts of the utilizable polybasic acid are the same as in the second embodiment.
- DMSSIP is used to facilitate water-solubility or water-dispersibility.
- the DMSSIP is preferably mixed in an amount of 1 to 30% by weight, based on the weight of the polybasic acid. If the amount of DMSSIP is less than 1% by weight, no addition effects thereof are substantially obtained. If the amount of DMSSIP is greater than 30% by weight, this may lead to problems associated with water resistance, chemical properties, and electrical properties.
- the polyhydric alcohol for adjusting the acid value is added to the resulting material to further progress polycondensation, thereby obtaining a polyester- amide polymer.
- specific examples of the polyhydric alcohol that can be used are the same as those used in the second embodiment.
- the polyester-amide polymer is dissolved in water, a hydrophilic organic solvent or a mixed solvent thereof to recover it in the form of an aqueous solution where the polymer is dissolved in water, in the form of an organic solution where the polymer is dissolved in a hydrophilic organic solvent, or in solid form.
- a hydrophilic organic solvent or a mixed solvent thereof to recover it in the form of an aqueous solution where the polymer is dissolved in water, in the form of an organic solution where the polymer is dissolved in a hydrophilic organic solvent, or in solid form.
- specific examples and amounts of the hydrophilic organic solvent that can be used are the same as those used in the recycling method in accordance with the second embodiment.
- a polyester oligomer containing an alkali metal sulfonate residue of aromatic dicarboxylic acid including DMSSIP is prepared.
- This polyester oligomer may be prepared via conventional processes for preparing polyester, such as transester- ification or direct esterification.
- the alkali metal sulfonate of aromatic dicarboxylic acid including DMSSIP is mixed and used.
- the alkali metal sulfonate of aromatic dicarboxylic acid is preferably used in an amount of 1 to 30% by weight, based on the weight of the polybasic acid.
- the amount of the alkali metal sulfonate of aromatic dicarboxylic acid is less than 1% by weight, no additional effects thereof are substantially obtained.
- the amount of the alkali metal sulfonate of aromatic dicarboxylic acid is greater than 30% by weight, thermal and mechanical properties of the resulting polyester- amide polymer are disadvantageously insufficient for practical use.
- the polyester oligomer containing alkali metal sulfonate residue of aromatic dicarboxylic acid is reacted with the mixed waste to depolymerize the mixed waste.
- reaction is continued to further progress, it is possible to obtain a polyester- amide polymer exhibiting increased solubility in water or a mixed solvent of water and hydrophilic solvent via polycondensation following transesterification.
- polyester-amide block polymer is recovered in the form of an aqueous solution or hydrophilic organic solution where the polymer is dissolved in water, a hydrophilic solvent or a mixed solvent thereof.
- specific examples and amounts of the utilizable hydrophilic solvent are the same as those used in the recycling method in accordance with the second embodiment.
- polyester-amide polymer may be directly recovered in solid form.
- oil and fat is transesterified with a polyhydric alcohol including glycerin to prepare monoglycerides of fatty acids and mono polyhydric alcoholides of fatty acids.
- the mixed waste is added to and reacted with the resulting material to obtain a depolymerized product.
- a polybasic acid is added to the depolymerization product, thereby leading to polycondensation thereof, followed by addition of the polyhydric alcohol to control an acid value. Further progress of polycondensation is carried out to obtain an oil-modified alkyd resin containing a polyester-amide block polymer which is then dissolved in an organic solvent such as naphtha or xylene to prepare an organic solution of the oil-modified alkyd resin.
- specific examples of the polybasic acid and polyhydric alcohol that can be used are the same as in the second embodiment.
- a monomer and waste polyamide producing polyamide may be further added and reacted to produce a polyamide block in step (b).
- the thus-obtained polyester-amide block polymer has a flow beginning temperature (Tfb) of 10 to 110°C, a flow ending temperature (Tend) of 110 to 165°C and a glass transition temperature of 10 to 85°C, as measured using a capillary extrusion rheometer under a given load.
- Tfb flow beginning temperature
- Tend flow ending temperature
- glass transition temperature 10 to 85°C, as measured using a capillary extrusion rheometer under a given load.
- the thus-obtained polyester-amide resin has two or three carboxyl groups at chain ends thereof, thus giving rise to good reactivity and dispersibility.
- the polyester- amide resin recycled in accordance with the present invention can be used as synthetic resin fine particles, microcapsules, adsorbents, polymerization toner binders for electron photography, fiber processing agents, sizing agents for paper-making and paper strength agents, wastewater treatment agents, cement admixtures, inkjet ink binders, epoxy resin curing agents and modifiers, water-dispersible epoxy resin curing agents and modifiers.
- the water-soluble polyester-amide block polymer composition of the present invention has good dispersibility, compatibility and solubility, and thus can form a shell on the surface of a core material selected from drugs, fragrance agents, metal powders and the like. Therefore, the polyester-amide block polymer composition of the present invention is mixed with the core material and the resulting mixture is suspended in water containing a suspension promoter, filtered, and washed with water to prepare synthetic resin fine particles having a particle diameter of 1 to 10 D. The thus-prepared particles can be employed as cosmetics, drug carriers or materials for electronics.
- the water-soluble polyester-amide resin composition of the present invention exhibits excellent compatibility, solubility, dispersibility and adhesiveness, and thus can be used as synthetic fiber yarns, textile sizing agents and processing agents.
- the water-soluble polyester-amide composition of the present invention exhibits excellent reactivity, adhesiveness and cohesiveness with pulp cellulose, and thus can be used as sizing agents for use in paper making and paper strength agents.
- the water-soluble polyester-amide composition of the present invention exhibits excellent reactivity and cohesiveness with sludge in wastewater, and thus can be used as wastewater treatment agents.
- the water-soluble polyester-amide composition of the present invention exhibits high reactivity with epoxy resins due to amide groups contained therein, and excellent adhesiveness, plasticity and solubility and thus may be used as curing agents and modifying agents.
- polyester-amide recycled from the mixed waste in accordance with the present invention Upon utilizing the polyester-amide recycled from the mixed waste in accordance with the present invention, it is possible to prepare a powder coating composition using an epoxy resin as the curing agent.
- the polyester-amide reproduced via the recycling method of the present invention has two or three carboxyl groups at chain ends thereof, thus giving rise to good reactivity and dispersibility.
- the polyester-amide recycled via the recycling method of the present invention has excellent storage stability. It is a low- softening point resin and thus is curable within a short period of time, for example, 10 minutes, at below 180°C.
- polyester-amide reproduced according to the method of the present invention as a heat-curable paint for metals, it is possible to lower the curing temperature of the film and thus it is possible to obtain a coated film having high glossiness, superior heat and chemical resistance.
- polyester-amide reproduced from the mixed waste according to the present invention enables preparation of oil-modified alkyd varnish paints and printer inks.
- the oil-modified alkyd varnish paints obtained by reacting the polyester-amide obtained according to the present invention with a fatty acid and dry oil, have excellent solubility in an aliphatic hydrocarbon solvent or aromatic hydrocarbon solvent, and the coated film obtained using the same exhibits excellent and firm glossiness, water resistance and weatherability.
- gravure ink prepared by adding the colorant and additives to the polyester-amide obtained according to the present invention, is highly soluble in a mixed solvent of a ketone and aromatic hydrocarbon and thus it is possible to obtain superior printed form having fast dryness, and excellent adhesiveness, abrasion resistance and fastness.
- polyester-amide recycled from the mixed waste according to the present invention enables preparation of an adhesive.
- a hot melt adhesive utilizing the polyester-amide reproduced according to the present invention as a base resin has low softening point, low melt viscosity, excellent adhesiveness, water resistance, chemical resistance, accelerability and compatibility. Thereby, it is possible to obtain superior initial adhesiveness and strong adhesive force in various substrates including paper, board, bide and leather, textiles, wood, plastics and metals such as aluminum.
- a liquid adhesive obtained by dissolving the polyester-amide reproduced according to the present invention, as a base resin, in an organic solvent, may also be usefully employed to adhere the above-mentioned substrates.
- the toner particles were charged to a printer cartridge to perform a printing process. Upon printing images, images were distinctive and excellent fastness was obtained.
- An aqueous polyester-amide resin solution was prepared in the same manner as in example 1, except that 400 g of mixed waste chips, 200 g of hydrogenated rosin, 0.3 g of dibutyltin oxide (DBTO), 150 g of anhydrous trimellitic acid and 200 g of neopentyl glycol were charged to the reactor.
- the polyester-amide of the thus-obtained aqueous polyester-amide resin solution exhibited an acid value of 30 mgKOH/g, a weight average molecular weight of 11,000, a softening point of 91°C and a pH of 8.5.
- a toner was prepared via a polymerization method as follows. As a result, it was possible to prepare a toner having good physical properties and fastness.
- An aqueous polyester-amide resin solution was prepared in the same manner as in example 3, except that 400 g of mixed waste chips, 100 g of ethylene glycol, 0.3 g of DBTO and 150 g of anhydrous trimellitic acid were employed.
- aqueous polyester-amide resin exhibited an acid value of 45 mgKOH/g, a weight average molecular weight of 12,500, a softening point of 105°C and a pH of 7.7.
- An aqueous polyester-amide resin solution was prepared in the same manner as in example 3, except that 400 g of mixed waste chips, 100 g of propylene glycol, 0.3 g of DBTO, 50 g of adipic acid and 100 g of anhydrous maleic acid were employed.
- a polyester-amide block polymer was prepared in the same manner as in example 3, except that 350 g of mixed waste chips, 100 g of neopentyl glycol, 250 g of maleated gum rosin, 0.3 g of DBTO and 100 g of adipic acid were employed. Then, 150 g of triethylenetetramine was added to render the mixture water-soluble, thereby preparing an aqueous solution of the polyester-amide.
- the polyester-amide of the thus-obtained aqueous polyester-amide block polymer solution exhibited an acid value of 45 mgKOH/g, a weight average molecular weight of 11,200, a softening point of 79°C and a pH of 8.5.
- An aqueous solution of a polyester-amide resin was prepared in the same manner as in example 3, except that 350 g of mixed waste chips, 100 g of neopentyl glycol, 250 g of dicyclopentadiene resin, 0.3 g of DBTO and 150 g of anhydrous maleic acid were employed.
- the thus-obtained water-soluble polyester-amide resin exhibited an acid value of 70 mgKOH/g, a weight average molecular weight of 11,000 and a pH of 7.1.
- a polyester-amide block polymer was prepared in the same manner as in example 3, except that 400 g of mixed waste chips, 70 g of neopentyl glycol, 200 g of dicyclopentadiene resin, 0.3 g of DBTO, 100 g of isophthalic acid and 120 g of ethylene oxide adduct of bisphenol A were employed.
- the solid polyester-amide resin exhibited an acid value of 7 mgKOH/g, a weight average molecular weight of 19,000 and a softening point of 120°C.
- a polyester-amide block polymer was prepared in the same manner as in example 3, except that 500 g of mixed waste chips, 100 g of diethylene glycol, 0.3 g of DBTO, 100 g of anhydrous maleic acid, 100 g of waste nylon molded article and 100 g of pen- taerythritol were employed.
- polyester-amide block polymer exhibited an acid value of 5 mgKOH/g, a weight average molecular weight of 27,000 and a softening point of 140°C.
- a polyester-amide block polymer prepared according to a recycling method of a mixed waste of the present invention exhibits excellent compatibility and dispersibility with additives including a colorant and excellent adhesiveness to various substrates, and is also possible to be rendered water- soluble.
- an aqueous polyester-amide block polymer solution prepared from the mixed waste in accordance with the present invention can be utilized as industrially useful material such as synthetic resin fine particles, microcapsules, adsorbents, polymerization toner binders for electron photography, fiber processing agents, sizing agents for use in paper-making and paper strength agents, wastewater treatment agents, dispersants, cement admixtures, inkjet ink binders, epoxy resin curing agents and modifiers, water-dispersible epoxy resin curing agents and modifiers.
- polyester- amide block polymer in solid form or in the form of an organic solution can be employed as industrially useful material such as binders for toner manufactured by grinding methods, printer inks, coating materials, powder paints, adhesives, hot melt adhesives, waterproof agents, crosslinking curable unsaturated polyester-amide resins, and polyurethane resins.
Abstract
Description
Claims
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KR20040020944A KR101160352B1 (en) | 2004-03-26 | 2004-03-26 | Highly functional resin recycled polyester and polyamide hybrid waste and its manufacturing method |
KR1020040023579A KR20050098385A (en) | 2004-04-06 | 2004-04-06 | Highly functional polymer composition recycled waste polymer and its manufacturing method |
KR10-2004-0023579 | 2004-04-06 |
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