JPWO2021072020A5 - - Google Patents
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- Publication number
- JPWO2021072020A5 JPWO2021072020A5 JP2022520988A JP2022520988A JPWO2021072020A5 JP WO2021072020 A5 JPWO2021072020 A5 JP WO2021072020A5 JP 2022520988 A JP2022520988 A JP 2022520988A JP 2022520988 A JP2022520988 A JP 2022520988A JP WO2021072020 A5 JPWO2021072020 A5 JP WO2021072020A5
- Authority
- JP
- Japan
- Prior art keywords
- recycled
- polyester
- reaction zone
- glycol
- tpa
- 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
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 463
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 238
- 229920000728 polyester Polymers 0.000 claims description 140
- 238000005886 esterification reaction Methods 0.000 claims description 131
- 230000032050 esterification Effects 0.000 claims description 128
- 238000006243 chemical reaction Methods 0.000 claims description 126
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 77
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 64
- 239000003054 catalyst Substances 0.000 claims description 57
- 150000001463 antimony compounds Chemical class 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 51
- 239000003381 stabilizer Substances 0.000 claims description 49
- FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 claims description 48
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 claims description 48
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 46
- 229910052698 phosphorus Inorganic materials 0.000 claims description 44
- 150000003609 titanium compounds Chemical class 0.000 claims description 44
- 239000011574 phosphorus Substances 0.000 claims description 43
- -1 phosphorus compound Chemical class 0.000 claims description 41
- 239000002002 slurry Substances 0.000 claims description 35
- 239000000155 melt Substances 0.000 claims description 34
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 32
- 238000006068 polycondensation reaction Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 239000010936 titanium Substances 0.000 claims description 16
- 229910052719 titanium Inorganic materials 0.000 claims description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 150000002334 glycols Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 claims description 2
- WJJGAKCAAJOICV-UHFFFAOYSA-N N-dimethyltyrosine Natural products CN(C)C(C(O)=O)CC1=CC=C(O)C=C1 WJJGAKCAAJOICV-UHFFFAOYSA-N 0.000 claims description 2
- ZVOOGERIHVAODX-UHFFFAOYSA-N O-demycinosyltylosin Natural products O=CCC1CC(C)C(=O)C=CC(C)=CC(CO)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(O)C(C)(O)C2)C(C)O1 ZVOOGERIHVAODX-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- BMYPOELGNTXHPU-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxastibolan-2-yl) oxalate Chemical compound [Sb+3].[Sb+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O BMYPOELGNTXHPU-UHFFFAOYSA-H 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 description 56
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 11
- 150000003018 phosphorus compounds Chemical class 0.000 description 11
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962912234P | 2019-10-08 | 2019-10-08 | |
| US62/912,234 | 2019-10-08 | ||
| US201962925877P | 2019-10-25 | 2019-10-25 | |
| US62/925,877 | 2019-10-25 | ||
| PCT/US2020/054699 WO2021072020A1 (en) | 2019-10-08 | 2020-10-08 | Catalyst systems for crystallizable reactor grade resins with recycled content |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2022552207A JP2022552207A (ja) | 2022-12-15 |
| JPWO2021072020A5 true JPWO2021072020A5 (enrdf_load_stackoverflow) | 2025-03-18 |
Family
ID=73038416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022520988A Pending JP2022552207A (ja) | 2019-10-08 | 2020-10-08 | 再資源化含量を有する結晶化可能な反応器級樹脂のための触媒システム |
Country Status (6)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3154880A1 (en) * | 2019-10-25 | 2021-04-29 | Mark Allen Peters | Copolyesters produced from recycled copolyesters |
| JP7697369B2 (ja) * | 2020-04-15 | 2025-06-24 | 東洋紡株式会社 | 共重合ポリエステル樹脂、成形品、熱収縮性フィルム、及び繊維 |
| EP4335903A4 (en) * | 2021-05-06 | 2025-03-26 | Toyobo Co., Ltd. | METHOD FOR PRODUCING POLYESTER RESIN COMPOSITION AND METHOD FOR REGENERATION OF COLLECTED POLYESTER RESIN |
| US20240376258A1 (en) | 2021-08-31 | 2024-11-14 | Eastman Chemical Company | Articles comprising copolyesters produced with germanium catalyst |
| KR20240167667A (ko) * | 2022-03-18 | 2024-11-27 | 이스트만 케미칼 컴파니 | 다층 결정화가능 및 수축가능 필름 및 시트 |
| EP4504516A1 (en) * | 2022-04-06 | 2025-02-12 | Eastman Chemical Company | Multilayer shrinkable polyester films with improved toughness |
| CN117753338A (zh) * | 2022-08-24 | 2024-03-26 | 浙江佳人新材料有限公司 | 一种再生dmt及其共聚酯的缩聚釜装置 |
| WO2024246768A1 (en) * | 2023-06-01 | 2024-12-05 | Enel Green Power Italia S.r.l. | New polyester material for a high-performance polymer applications |
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| US4138459A (en) | 1975-09-08 | 1979-02-06 | Celanese Corporation | Process for preparing a microporous polymer film |
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| CN109563249A (zh) * | 2016-08-18 | 2019-04-02 | 伊士曼化工公司 | 用于压延的包含四甲基环丁二醇和乙二醇的聚酯组合物 |
| EP3878888A1 (en) * | 2016-08-18 | 2021-09-15 | Eastman Chemical Company | Polyester compositions which comprise tetramethyl cyclobutanediol and ethylene glycol, with improved catalyst system |
| JP2018135427A (ja) * | 2017-02-21 | 2018-08-30 | 東レ株式会社 | 共重合ポリエステルの連続製造方法 |
-
2020
- 2020-10-08 EP EP20799903.8A patent/EP4041797A1/en active Pending
- 2020-10-08 JP JP2022520988A patent/JP2022552207A/ja active Pending
- 2020-10-08 CN CN202080084946.4A patent/CN114787233B/zh active Active
- 2020-10-08 KR KR1020227015231A patent/KR20220079916A/ko active Pending
- 2020-10-08 US US17/754,630 patent/US20220372217A1/en active Pending
- 2020-10-08 WO PCT/US2020/054699 patent/WO2021072020A1/en unknown
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