CA2148478C - Thermoplastic biodegradable resins and a process of preparation thereof - Google Patents
Thermoplastic biodegradable resins and a process of preparation thereof Download PDFInfo
- Publication number
- CA2148478C CA2148478C CA002148478A CA2148478A CA2148478C CA 2148478 C CA2148478 C CA 2148478C CA 002148478 A CA002148478 A CA 002148478A CA 2148478 A CA2148478 A CA 2148478A CA 2148478 C CA2148478 C CA 2148478C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- reaction
- ofi
- formula
- ester
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 20
- 229920006167 biodegradable resin Polymers 0.000 title abstract description 5
- 229920001169 thermoplastic Polymers 0.000 title abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 title abstract description 5
- 230000008569 process Effects 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 150000002009 diols Chemical class 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 23
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 238000006068 polycondensation reaction Methods 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical group [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 9
- -1 dicarboxylic acid compound Chemical class 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 4
- 239000001639 calcium acetate Substances 0.000 claims description 4
- 229960005147 calcium acetate Drugs 0.000 claims description 4
- 235000011092 calcium acetate Nutrition 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical group COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- 229940011182 cobalt acetate Drugs 0.000 claims description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical group [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 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 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229920006230 thermoplastic polyester resin Polymers 0.000 claims 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims 2
- 229910001887 tin oxide Inorganic materials 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 229920001225 polyester resin Polymers 0.000 claims 1
- 239000004645 polyester resin Substances 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000001384 succinic acid Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 5
- 229920003232 aliphatic polyester Polymers 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000012770 industrial material Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920000229 biodegradable polyester Polymers 0.000 description 1
- 239000004622 biodegradable polyester Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- FQFKDCGKJRWARK-UHFFFAOYSA-N butanedioic acid;pentanedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)CCCC(O)=O FQFKDCGKJRWARK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FZWBABZIGXEXES-UHFFFAOYSA-N ethane-1,2-diol;hexanedioic acid Chemical compound OCCO.OC(=O)CCCCC(O)=O FZWBABZIGXEXES-UHFFFAOYSA-N 0.000 description 1
- UVSDPQBAKJACCV-UHFFFAOYSA-N ethene;hexanedioic acid Chemical group C=C.OC(=O)CCCCC(O)=O UVSDPQBAKJACCV-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1992/25478 | 1992-12-24 | ||
| KR920025478 | 1992-12-24 | ||
| KR1993/20638 | 1993-10-06 | ||
| KR1019930020638A KR0120326B1 (ko) | 1992-12-24 | 1993-10-06 | 열가소성 생분해성 지방족 폴리에스테르 및 그 제조방법 |
| PCT/KR1993/000116 WO1994014870A1 (en) | 1992-12-24 | 1993-12-23 | Thermoplastic biodegradable resins and a process of preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2148478A1 CA2148478A1 (en) | 1994-07-07 |
| CA2148478C true CA2148478C (en) | 2000-07-04 |
Family
ID=26629444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002148478A Expired - Fee Related CA2148478C (en) | 1992-12-24 | 1993-12-23 | Thermoplastic biodegradable resins and a process of preparation thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5470941A (en, 2012) |
| EP (1) | EP0675913B1 (en, 2012) |
| JP (1) | JP2564463B2 (en, 2012) |
| KR (1) | KR0120326B1 (en, 2012) |
| CN (1) | CN1037850C (en, 2012) |
| AU (1) | AU682017B2 (en, 2012) |
| CA (1) | CA2148478C (en, 2012) |
| DE (1) | DE69323632T2 (en, 2012) |
| TW (1) | TW257770B (en, 2012) |
| WO (1) | WO1994014870A1 (en, 2012) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2136311A1 (en) * | 1993-03-22 | 1994-09-29 | Yoshiaki Iwaya | Aliphatic polyesters and method of preparing the same |
| US5480962A (en) * | 1993-07-22 | 1996-01-02 | Eastman Chemical Company | Copolyesters having repeat units derived from succinic acid |
| US5616681A (en) * | 1994-11-01 | 1997-04-01 | Nippon Shokubai Co., Ltd. | Process for producing aliphatic polyester |
| KR100330379B1 (ko) * | 1994-12-21 | 2002-08-28 | 에스케이케미칼주식회사 | 투명성이우수한열가소성지방족폴리에스테르수지및그제조방법 |
| KR100330380B1 (ko) * | 1994-12-21 | 2002-10-25 | 에스케이케미칼주식회사 | 열가소성지방족폴리에스테르수지및그제조방법 |
| JPH08196175A (ja) * | 1995-01-30 | 1996-08-06 | Daiwa Seiko Inc | 釣り糸 |
| DE19518943C2 (de) * | 1995-05-23 | 1999-12-09 | Inventa Fischer Gmbh | Verfahren zur Herstellung von Polyestern unter Verwendung von titanhaltigen Katalysator-Inhibitor-Kombinationen |
| US5912076A (en) | 1996-12-31 | 1999-06-15 | Kimberly-Clark Worldwide, Inc. | Blends of polyethylene and peo having inverse phase morphology and method of making the blends |
| US5976694A (en) * | 1997-10-03 | 1999-11-02 | Kimberly-Clark Worldwide, Inc. | Water-sensitive compositions for improved processability |
| ES2190655T3 (es) * | 1998-08-28 | 2003-08-01 | Mini Ricerca Scient Tecnolog | Uso de resinas de poliesteres para la produccion de articulos que tienen buenas propiedades de barrera respecto al vapor de agua. |
| US6713414B1 (en) | 2000-05-04 | 2004-03-30 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US7276459B1 (en) | 2000-05-04 | 2007-10-02 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6579570B1 (en) | 2000-05-04 | 2003-06-17 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6423804B1 (en) | 1998-12-31 | 2002-07-23 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive hard water dispersible polymers and applications therefor |
| IT1307022B1 (it) | 1999-03-15 | 2001-10-23 | Novamont Spa | Processo semplificato per l'ottenimento di poliesteri alifaticibiodegradabili. |
| US20030220466A1 (en) | 2001-12-04 | 2003-11-27 | Ministero Dell'universita' E Della Ricerca Scientifica E Tecnologica | Simplified method of producing biodegradable aliphatic polyesters |
| US6444761B1 (en) | 1999-12-28 | 2002-09-03 | Kimberly-Clark Worldwide, Inc. | Water-soluble adhesive compositions |
| US6815502B1 (en) | 2000-05-04 | 2004-11-09 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersable polymers, a method of making same and items using same |
| US6653406B1 (en) | 2000-05-04 | 2003-11-25 | Kimberly Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6444214B1 (en) | 2000-05-04 | 2002-09-03 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6599848B1 (en) | 2000-05-04 | 2003-07-29 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6429261B1 (en) | 2000-05-04 | 2002-08-06 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6835678B2 (en) | 2000-05-04 | 2004-12-28 | Kimberly-Clark Worldwide, Inc. | Ion sensitive, water-dispersible fabrics, a method of making same and items using same |
| US7101612B2 (en) | 2000-05-04 | 2006-09-05 | Kimberly Clark Worldwide, Inc. | Pre-moistened wipe product |
| US6683143B1 (en) | 2000-05-04 | 2004-01-27 | Kimberly Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6548592B1 (en) | 2000-05-04 | 2003-04-15 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US6586529B2 (en) | 2001-02-01 | 2003-07-01 | Kimberly-Clark Worldwide, Inc. | Water-dispersible polymers, a method of making same and items using same |
| US6828014B2 (en) | 2001-03-22 | 2004-12-07 | Kimberly-Clark Worldwide, Inc. | Water-dispersible, cationic polymers, a method of making same and items using same |
| US6897168B2 (en) | 2001-03-22 | 2005-05-24 | Kimberly-Clark Worldwide, Inc. | Water-dispersible, cationic polymers, a method of making same and items using same |
| US7070854B2 (en) | 2001-03-22 | 2006-07-04 | Kimberly-Clark Worldwide, Inc. | Water-dispersible, cationic polymers, a method of making same and items using same |
| US6908966B2 (en) | 2001-03-22 | 2005-06-21 | Kimberly-Clark Worldwide, Inc. | Water-dispersible, cationic polymers, a method of making same and items using same |
| KR20040005194A (ko) * | 2002-07-08 | 2004-01-16 | 주식회사 이래화학 | 성형성이 우수한 생분해성 지방족 폴리에스테르 복합수지제조방법 |
| KR100537211B1 (ko) * | 2003-03-04 | 2005-12-16 | 학교법인 한양학원 | 생분해성이 우수한 새로운 지방족 폴리에스테르 이오노머수지와 그의 제조방법 |
| DE102007003649A1 (de) | 2007-01-18 | 2008-07-24 | Rebac Gmbh | Kupfer(II)enthaltende Formmasse aus Polyester, ihre Herstellung und Verwendung |
| DE102007003648A1 (de) | 2007-01-18 | 2008-07-24 | Rebac Gmbh | Kupferenthaltende Formmasse aus Polyester, ihre Herstellung und Verwendung |
| DE102007003662A1 (de) | 2007-01-18 | 2008-07-24 | Rebac Gmbh | Kupfer(I)enthaltende Formmasse aus Polyester, ihre Herstellung und Verwendung |
| CN101977963B (zh) * | 2008-03-28 | 2013-03-27 | 三菱化学株式会社 | 脂肪族聚酯的制造方法 |
| JP5624730B2 (ja) * | 2009-04-24 | 2014-11-12 | 株式会社日立製作所 | ポリエステルの合成方法および装置 |
| ES2659350T3 (es) | 2009-09-14 | 2018-03-14 | Basf Se | Dispensador que comprende una membrana de poliéster para el control de ácaros en colmenas de abejas |
| EA201200862A1 (ru) | 2009-12-11 | 2013-01-30 | Басф Се | Приманка для грызунов, упакованная в биоразлагаемую пленку |
| CN101935391B (zh) * | 2010-09-02 | 2013-03-06 | 上海华谊（集团）公司 | 一种高分子量脂肪族聚酯的制备方法 |
| CN103468195A (zh) * | 2013-09-26 | 2013-12-25 | 上海天洋热熔胶有限公司 | 一种生物可降解聚酯热熔胶的制备方法 |
| WO2016087270A1 (en) | 2014-12-04 | 2016-06-09 | Basf Se | Solid agrochemical composition for extended release of carbon dioxide |
| PT3322287T (pt) | 2015-07-13 | 2025-07-01 | Basf Corp | Sistema de controlo e/ou de deteção de pragas com matriz de isco condutora |
| CN114456561A (zh) * | 2016-10-27 | 2022-05-10 | 丹尼米尔生物塑料有限公司 | 含有pbsa增塑剂的聚合物组合物 |
| BR112020000157B1 (pt) | 2017-07-07 | 2023-12-12 | Basf Corporation | Sistema de monitoramento de pragas |
| KR101941123B1 (ko) | 2018-06-07 | 2019-01-23 | 문봉주 | 생분해성 수지 및 이로부터 제조된 생분해성 필름 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3157618A (en) * | 1959-03-31 | 1964-11-17 | Pittsburgh Plate Glass Co | Oxides of tin as catalysts in the preparation of polyesters |
| US3501554A (en) * | 1966-09-12 | 1970-03-17 | Emery Industries Inc | Polyester plasticizer for polyvinyl chloride fabrics |
| DE2045914B2 (de) * | 1970-09-17 | 1975-11-27 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von linearen, hochmolekularen Polyestern |
| JPS5134860B2 (en, 2012) * | 1972-05-18 | 1976-09-29 | ||
| US3959200A (en) * | 1973-10-25 | 1976-05-25 | E. I. Du Pont De Nemours And Company | Copolyester composition |
| JPS5530010B2 (en, 2012) * | 1973-11-19 | 1980-08-07 | ||
| US3962189A (en) * | 1974-11-01 | 1976-06-08 | Eastman Kodak Company | Process and catalyst-inhibitor systems for preparing synthetic linear polyesters |
| NL7614132A (nl) * | 1975-12-22 | 1977-06-24 | Monsanto Co | Werkwijze voor de bereiding van een hoog mole- culaire polyester weekmaker en voorwerpen, ver- vaardigd onder toepassing van de aldus bereide weekmaker. |
| DD285504A7 (de) * | 1985-04-19 | 1990-12-19 | Kuehnel,Horst,Dd | Verfahren zur lichtstabilisierung von polyester |
| US4959445A (en) * | 1986-02-25 | 1990-09-25 | Celanese Corporation | Preparation of gray to blue aromatic polyesters by incorporation of cobalt into the catalyst system |
| US4780527A (en) * | 1987-05-06 | 1988-10-25 | Industrial Technology Research Institute | Preparation of polyesters from terephthalic acid |
| WO1989002903A1 (en) * | 1987-09-30 | 1989-04-06 | Ecoplastics Limited | Production of photodegradable polyester plastics |
| GB2242197A (en) * | 1990-03-23 | 1991-09-25 | Bostik Ltd | High-molecular weight polyhexamethylene adipate |
| US5306787A (en) * | 1990-11-26 | 1994-04-26 | Showa Highpolymer Co., Ltd. | Method for producing saturated polyester |
| DE69125170T2 (de) * | 1990-11-30 | 1997-06-19 | Eastman Chemical Co., Kingsport, Tenn. | Mischungen von aliphatisch-aromatischen Copolyestern mit Celluloseester-Polymeren |
| GB9102950D0 (en) * | 1991-02-12 | 1991-03-27 | Bostik Ltd | High molecular weight polymethylene adipates |
| JPH05310898A (ja) * | 1992-05-14 | 1993-11-22 | Showa Highpolymer Co Ltd | 高分子量脂肪族ポリエステル |
| JPH06145313A (ja) * | 1992-11-09 | 1994-05-24 | Unitika Ltd | 脂肪族ポリエステル及びその製造方法 |
-
1993
- 1993-10-06 KR KR1019930020638A patent/KR0120326B1/ko not_active Expired - Lifetime
- 1993-12-17 TW TW082110720A patent/TW257770B/zh active
- 1993-12-23 CA CA002148478A patent/CA2148478C/en not_active Expired - Fee Related
- 1993-12-23 EP EP94903109A patent/EP0675913B1/en not_active Expired - Lifetime
- 1993-12-23 WO PCT/KR1993/000116 patent/WO1994014870A1/en active IP Right Grant
- 1993-12-23 US US08/172,281 patent/US5470941A/en not_active Expired - Lifetime
- 1993-12-23 DE DE69323632T patent/DE69323632T2/de not_active Expired - Fee Related
- 1993-12-23 AU AU57179/94A patent/AU682017B2/en not_active Ceased
- 1993-12-24 JP JP5347299A patent/JP2564463B2/ja not_active Expired - Fee Related
- 1993-12-24 CN CN93121098A patent/CN1037850C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU5717994A (en) | 1994-07-19 |
| EP0675913B1 (en) | 1999-02-24 |
| WO1994014870A1 (en) | 1994-07-07 |
| TW257770B (en, 2012) | 1995-09-21 |
| KR0120326B1 (ko) | 1997-10-22 |
| US5470941A (en) | 1995-11-28 |
| AU682017B2 (en) | 1997-09-18 |
| CN1037850C (zh) | 1998-03-25 |
| DE69323632T2 (de) | 1999-09-30 |
| JPH06293826A (ja) | 1994-10-21 |
| CN1088945A (zh) | 1994-07-06 |
| CA2148478A1 (en) | 1994-07-07 |
| DE69323632D1 (de) | 1999-04-01 |
| JP2564463B2 (ja) | 1996-12-18 |
| EP0675913A1 (en) | 1995-10-11 |
| KR940014497A (ko) | 1994-07-18 |
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