CN101250258B - Method for producing bio-degradable copolyester by employing composite catalyst - Google Patents
Method for producing bio-degradable copolyester by employing composite catalyst Download PDFInfo
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- CN101250258B CN101250258B CN2008100918997A CN200810091899A CN101250258B CN 101250258 B CN101250258 B CN 101250258B CN 2008100918997 A CN2008100918997 A CN 2008100918997A CN 200810091899 A CN200810091899 A CN 200810091899A CN 101250258 B CN101250258 B CN 101250258B
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- Prior art keywords
- acid
- composite catalyst
- biodegradable copolyester
- contain
- catalyst
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- 239000003054 catalyst Substances 0.000 title claims abstract description 113
- 229920001634 Copolyester Polymers 0.000 title claims abstract description 71
- 239000002131 composite material Substances 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 26
- -1 phosphite esters compound Chemical class 0.000 claims abstract description 24
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000005886 esterification reaction Methods 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000292 calcium oxide Substances 0.000 claims abstract description 14
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000010936 titanium Substances 0.000 claims abstract description 13
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 7
- 230000000737 periodic effect Effects 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 150000007942 carboxylates Chemical class 0.000 claims description 22
- 230000032050 esterification Effects 0.000 claims description 22
- 238000000967 suction filtration Methods 0.000 claims description 22
- 238000001035 drying Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- 239000000377 silicon dioxide Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 11
- 244000144992 flock Species 0.000 claims description 11
- 238000009775 high-speed stirring Methods 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 229960001866 silicon dioxide Drugs 0.000 claims description 10
- 235000012239 silicon dioxide Nutrition 0.000 claims description 10
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 7
- 239000001384 succinic acid Substances 0.000 claims description 7
- LVFFZQQWIZURIO-UHFFFAOYSA-N 2-phenylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)C1=CC=CC=C1 LVFFZQQWIZURIO-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 6
- 150000004706 metal oxides Chemical class 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- DVQJZMHWNRXGSM-UHFFFAOYSA-N bis(2-methylpropyl) hydrogen phosphite Chemical compound CC(C)COP(O)OCC(C)C DVQJZMHWNRXGSM-UHFFFAOYSA-N 0.000 claims description 5
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 4
- REKYPYSUBKSCAT-UHFFFAOYSA-N 3-hydroxypentanoic acid Chemical compound CCC(O)CC(O)=O REKYPYSUBKSCAT-UHFFFAOYSA-N 0.000 claims description 4
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 claims description 4
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims description 3
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims description 3
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 abstract description 5
- 238000009826 distribution Methods 0.000 abstract description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229960005137 succinic acid Drugs 0.000 abstract 1
- 150000003609 titanium compounds Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 11
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 238000005453 pelletization Methods 0.000 description 9
- 238000001291 vacuum drying Methods 0.000 description 9
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- LPHBARMWKLYWRA-UHFFFAOYSA-N thallium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Tl+3].[Tl+3] LPHBARMWKLYWRA-UHFFFAOYSA-N 0.000 description 3
- 150000003608 titanium Chemical class 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 229910004339 Ti-Si Inorganic materials 0.000 description 1
- 229910010978 Ti—Si Inorganic materials 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
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CN2008100918997A CN101250258B (en) | 2008-04-03 | 2008-04-03 | Method for producing bio-degradable copolyester by employing composite catalyst |
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CN2008100918997A CN101250258B (en) | 2008-04-03 | 2008-04-03 | Method for producing bio-degradable copolyester by employing composite catalyst |
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CN101250258A CN101250258A (en) | 2008-08-27 |
CN101250258B true CN101250258B (en) | 2010-12-08 |
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CN2008100918997A Active CN101250258B (en) | 2008-04-03 | 2008-04-03 | Method for producing bio-degradable copolyester by employing composite catalyst |
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101508771B (en) * | 2009-03-18 | 2011-08-24 | 马世金 | Method of preparing biodegradable multicomponent copolyester |
CN101724140B (en) * | 2009-12-04 | 2012-09-05 | 清华大学 | Method for preparing biodegradable polyester catalyst |
CN103435794B (en) * | 2013-07-26 | 2015-08-12 | 旭阳化学技术研究院有限公司 | A kind of preparation method of polycondensation catalyst, catalyzer prepared therefrom and the method with this catalyst preparing PBS and multipolymer thereof |
CN103910860B (en) * | 2014-04-11 | 2016-01-20 | 江苏金聚合金材料有限公司 | A kind of preparation method of degradable oxyacetic acid copolyesters |
CN104479115A (en) * | 2014-12-30 | 2015-04-01 | 衡阳师范学院 | Method for preparing linear polyester resin |
JP7001330B2 (en) * | 2015-07-16 | 2022-02-03 | 大阪瓦斯株式会社 | Biodegradable copolymer and its manufacturing method and biodegradability improving method |
CN108532126B (en) * | 2017-03-02 | 2021-04-16 | 江苏华龙无纺布有限公司 | Antibacterial biodegradable polyester non-woven fabric and preparation method thereof |
CN108285529B (en) * | 2018-01-29 | 2020-05-12 | 陕西科技大学 | Preparation method of biodegradable film capable of promoting plant growth |
CN114213814B (en) * | 2021-12-09 | 2023-03-14 | 广东省科学院生物与医学工程研究所 | Formula and preparation method of UV aging resistant biodegradable mulching film master batch |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1552755A (en) * | 2003-06-04 | 2004-12-08 | 中国石化集团天津石油化工公司 | Titanium composite catalyst for polyester and copolyester synthesis |
CN1644601A (en) * | 2004-12-29 | 2005-07-27 | 中国石化集团天津石油化工公司 | Preparation of liquid titanium polyester polycondensation catalyst |
JP2005314660A (en) * | 2004-03-30 | 2005-11-10 | Toray Ind Inc | Polyester composition and polyester film |
CN1861660A (en) * | 2006-06-16 | 2006-11-15 | 清华大学 | Biologic degradable copolyester and preparation process thereof |
-
2008
- 2008-04-03 CN CN2008100918997A patent/CN101250258B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1552755A (en) * | 2003-06-04 | 2004-12-08 | 中国石化集团天津石油化工公司 | Titanium composite catalyst for polyester and copolyester synthesis |
JP2005314660A (en) * | 2004-03-30 | 2005-11-10 | Toray Ind Inc | Polyester composition and polyester film |
CN1644601A (en) * | 2004-12-29 | 2005-07-27 | 中国石化集团天津石油化工公司 | Preparation of liquid titanium polyester polycondensation catalyst |
CN1861660A (en) * | 2006-06-16 | 2006-11-15 | 清华大学 | Biologic degradable copolyester and preparation process thereof |
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CN101250258A (en) | 2008-08-27 |
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Assignee: ANQING HEXING CHEMICAL Co.,Ltd. Assignor: Ma Shijin Contract record no.: 2011340000067 Denomination of invention: Method for producing bio-degradable copolyester by employing composite catalyst Granted publication date: 20101208 License type: Exclusive License Open date: 20080827 Record date: 20110628 |
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Assignee: ANQING HEXING CHEMICAL Co.,Ltd. Assignor: Ma Shijin Contract record no.: 2011340000067 Date of cancellation: 20230518 |
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