WO1997041165A1 - Bulk reactive extrusion polymerization process producing aliphatic ester polymer compositions - Google Patents
Bulk reactive extrusion polymerization process producing aliphatic ester polymer compositions Download PDFInfo
- Publication number
- WO1997041165A1 WO1997041165A1 PCT/US1997/006440 US9706440W WO9741165A1 WO 1997041165 A1 WO1997041165 A1 WO 1997041165A1 US 9706440 W US9706440 W US 9706440W WO 9741165 A1 WO9741165 A1 WO 9741165A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- aliphatic ester
- aluminum
- polymer
- monomer
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 229920000642 polymer Polymers 0.000 title claims abstract description 88
- -1 aliphatic ester Chemical class 0.000 title claims abstract description 85
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 59
- 238000001125 extrusion Methods 0.000 title abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 95
- 229920002472 Starch Polymers 0.000 claims abstract description 64
- 235000019698 starch Nutrition 0.000 claims abstract description 64
- 239000008107 starch Substances 0.000 claims abstract description 52
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229920003232 aliphatic polyester Polymers 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 65
- 230000008569 process Effects 0.000 claims description 59
- 239000012985 polymerization agent Substances 0.000 claims description 32
- 229910052751 metal Inorganic materials 0.000 claims description 30
- 239000002184 metal Substances 0.000 claims description 30
- 125000002524 organometallic group Chemical group 0.000 claims description 29
- 239000000376 reactant Substances 0.000 claims description 27
- 150000004676 glycans Chemical class 0.000 claims description 23
- 229920001282 polysaccharide Polymers 0.000 claims description 23
- 239000005017 polysaccharide Substances 0.000 claims description 23
- 229910052782 aluminium Inorganic materials 0.000 claims description 21
- 150000002596 lactones Chemical group 0.000 claims description 20
- 239000004014 plasticizer Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000004703 alkoxides Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 229910052718 tin Inorganic materials 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052772 Samarium Inorganic materials 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 3
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- DYHSMQWCZLNWGO-UHFFFAOYSA-N di(propan-2-yloxy)alumane Chemical compound CC(C)O[AlH]OC(C)C DYHSMQWCZLNWGO-UHFFFAOYSA-N 0.000 claims 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 7
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
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- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000004260 weight control 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
-
- 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
- C08G63/84—Boron, aluminium, gallium, indium, thallium, rare-earth metals, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
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)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP09538960A JP3140791B2 (en) | 1996-04-26 | 1997-04-18 | Bulk reactive extrusion polymerization process for producing aliphatic ester polymer compositions |
KR1019980708567A KR100316615B1 (en) | 1996-04-26 | 1997-04-18 | Bulk Reactive Extrusion Polymerization Process to Prepare Aliphatic Ester Polymer Compositions |
EP97918709A EP0895518A1 (en) | 1996-04-26 | 1997-04-18 | Bulk reactive extrusion polymerization process producing aliphatic ester polymer compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US639,198 | 1996-04-26 | ||
US08/639,198 US5801224A (en) | 1996-04-26 | 1996-04-26 | Bulk reactive extrusion polymerization process producing aliphatic ester polymer compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997041165A1 true WO1997041165A1 (en) | 1997-11-06 |
Family
ID=24563127
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/006440 WO1997041165A1 (en) | 1996-04-26 | 1997-04-18 | Bulk reactive extrusion polymerization process producing aliphatic ester polymer compositions |
Country Status (5)
Country | Link |
---|---|
US (3) | US5801224A (en) |
EP (1) | EP0895518A1 (en) |
JP (1) | JP3140791B2 (en) |
KR (1) | KR100316615B1 (en) |
WO (1) | WO1997041165A1 (en) |
Cited By (9)
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EP0878289A1 (en) * | 1997-05-16 | 1998-11-18 | SOLVAY (Société Anonyme) | Method of manufacturing biodegradable blown films |
US8268738B2 (en) | 2008-05-30 | 2012-09-18 | Kimberly-Clark Worldwide, Inc. | Polylactic acid fibers |
US8461262B2 (en) | 2010-12-07 | 2013-06-11 | Kimberly-Clark Worldwide, Inc. | Polylactic acid fibers |
US8518311B2 (en) | 2007-08-22 | 2013-08-27 | Kimberly-Clark Worldwide, Inc. | Multicomponent biodegradable filaments and nonwoven webs formed therefrom |
US8609808B2 (en) | 2006-07-14 | 2013-12-17 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic polyester for use in nonwoven webs |
US8710172B2 (en) | 2006-07-14 | 2014-04-29 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic-aromatic copolyester for use in nonwoven webs |
US9091004B2 (en) | 2006-07-14 | 2015-07-28 | Kimberly-Clark Worldwide, Inc. | Biodegradable polylactic acid for use in nonwoven webs |
WO2020005254A1 (en) * | 2018-06-28 | 2020-01-02 | Fedchem, Llc | Aluminum organic thickeners for thermoset resins |
US10745552B2 (en) | 2018-06-28 | 2020-08-18 | Fedchem, Llc | Aluminum organic thickeners for thermoset resins |
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EP0882751A3 (en) * | 1997-06-03 | 1999-02-10 | KABUSHIKI KAISHA KOBE SEIKO SHO also known as Kobe Steel Ltd. | Biodegradable polyester with improved moulding characteristics and its production |
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US6376643B1 (en) * | 2000-11-08 | 2002-04-23 | Invigor Biotechnology Co., Ltd. | Method of polymerization of lactide and polylactide homopolymer thereof |
US6747096B2 (en) | 2001-04-10 | 2004-06-08 | University Of Akron | Block copolymers of lactone and lactam, compatibilizing agents, and compatiblized polymer blends |
US6486257B1 (en) | 2001-04-10 | 2002-11-26 | University Of Akron | Block copolymers of lactone and lactam, compatabilizing agents, and compatibilized polymer blends |
US7173032B2 (en) * | 2001-09-21 | 2007-02-06 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7169785B2 (en) * | 2001-09-21 | 2007-01-30 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7112587B2 (en) * | 2001-09-21 | 2006-09-26 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7132423B2 (en) * | 2001-09-21 | 2006-11-07 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
WO2003050153A1 (en) * | 2001-12-12 | 2003-06-19 | North Carolina State University | Methods of co2-assisted reactive extrusion |
US7261839B2 (en) * | 2002-01-22 | 2007-08-28 | Northern Technologies International Corp. | Tarnish inhibiting composition and article containing it |
US20040173779A1 (en) * | 2002-01-22 | 2004-09-09 | Gencer Mehmet A. | Biodegradable shaped article containing a corrosion inhibitor and inert filler particles |
US20030220436A1 (en) * | 2002-01-22 | 2003-11-27 | Gencer Mehmet A. | Biodegradable polymers containing one or more inhibitors and methods for producing same |
US7270775B2 (en) * | 2002-01-22 | 2007-09-18 | Northern Technologies International Corp. | Corrosion inhibiting composition and article containing it |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5225129A (en) * | 1990-07-19 | 1993-07-06 | Dsm N.V. | Method for the manufacture of polymer products from cyclic esters |
US5310599A (en) * | 1993-05-06 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Method for making polymers of alpha-hydroxy acids |
US5468837A (en) * | 1993-05-17 | 1995-11-21 | Solvay (Societe Anonyme) | Process for the manufacture of poly-epsilon-caprolactones and poly-epsilon-caprolactones which have high molecular masses obtainable by this process |
US5500465A (en) * | 1994-03-10 | 1996-03-19 | Board Of Trustees Operating Michigan State University | Biodegradable multi-component polymeric materials based on unmodified starch-like polysaccharides |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4469613A (en) * | 1983-02-23 | 1984-09-04 | International Flavors & Fragrances Inc. | Detergent bar containing poly(epsilon caprolactone) and aromatizing agent |
US5412005A (en) * | 1991-05-03 | 1995-05-02 | Novamont S.P.A. | Biodegradable polymeric compositions based on starch and thermoplastic polymers |
EP0525245A1 (en) * | 1991-08-01 | 1993-02-03 | NOVAMONT S.p.A. | Disposable absorbent articles |
BE1009255A3 (en) * | 1995-04-07 | 1997-01-07 | Solvay | PERFECTED PROCESS FOR THE CONTINUOUS MANUFACTURING OF POLY- -CAPROLACTONES. |
-
1996
- 1996-04-26 US US08/639,198 patent/US5801224A/en not_active Expired - Fee Related
-
1997
- 1997-04-18 EP EP97918709A patent/EP0895518A1/en not_active Withdrawn
- 1997-04-18 KR KR1019980708567A patent/KR100316615B1/en not_active IP Right Cessation
- 1997-04-18 WO PCT/US1997/006440 patent/WO1997041165A1/en not_active Application Discontinuation
- 1997-04-18 JP JP09538960A patent/JP3140791B2/en not_active Expired - Fee Related
- 1997-09-08 US US08/925,529 patent/US5969089A/en not_active Expired - Lifetime
- 1997-09-08 US US08/925,528 patent/US5906783A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5225129A (en) * | 1990-07-19 | 1993-07-06 | Dsm N.V. | Method for the manufacture of polymer products from cyclic esters |
US5310599A (en) * | 1993-05-06 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Method for making polymers of alpha-hydroxy acids |
US5468837A (en) * | 1993-05-17 | 1995-11-21 | Solvay (Societe Anonyme) | Process for the manufacture of poly-epsilon-caprolactones and poly-epsilon-caprolactones which have high molecular masses obtainable by this process |
US5500465A (en) * | 1994-03-10 | 1996-03-19 | Board Of Trustees Operating Michigan State University | Biodegradable multi-component polymeric materials based on unmodified starch-like polysaccharides |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0878289A1 (en) * | 1997-05-16 | 1998-11-18 | SOLVAY (Société Anonyme) | Method of manufacturing biodegradable blown films |
BE1011157A3 (en) * | 1997-05-16 | 1999-05-04 | Solvay | Method of making film biodegradable breath. |
US6180053B1 (en) | 1997-05-16 | 2001-01-30 | Solvay S.A. (Societe Anonyme) | Process for manufacturing a biodegradable blown film |
US9260802B2 (en) | 2006-07-14 | 2016-02-16 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic polyester for use in nonwoven webs |
US8609808B2 (en) | 2006-07-14 | 2013-12-17 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic polyester for use in nonwoven webs |
US8710172B2 (en) | 2006-07-14 | 2014-04-29 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic-aromatic copolyester for use in nonwoven webs |
US9091004B2 (en) | 2006-07-14 | 2015-07-28 | Kimberly-Clark Worldwide, Inc. | Biodegradable polylactic acid for use in nonwoven webs |
US9394629B2 (en) | 2006-07-14 | 2016-07-19 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic-aromatic copolyester for use in nonwoven webs |
US8518311B2 (en) | 2007-08-22 | 2013-08-27 | Kimberly-Clark Worldwide, Inc. | Multicomponent biodegradable filaments and nonwoven webs formed therefrom |
US8268738B2 (en) | 2008-05-30 | 2012-09-18 | Kimberly-Clark Worldwide, Inc. | Polylactic acid fibers |
US8461262B2 (en) | 2010-12-07 | 2013-06-11 | Kimberly-Clark Worldwide, Inc. | Polylactic acid fibers |
WO2020005254A1 (en) * | 2018-06-28 | 2020-01-02 | Fedchem, Llc | Aluminum organic thickeners for thermoset resins |
US10745552B2 (en) | 2018-06-28 | 2020-08-18 | Fedchem, Llc | Aluminum organic thickeners for thermoset resins |
Also Published As
Publication number | Publication date |
---|---|
KR100316615B1 (en) | 2002-02-28 |
JP3140791B2 (en) | 2001-03-05 |
EP0895518A4 (en) | 1999-03-10 |
EP0895518A1 (en) | 1999-02-10 |
US5801224A (en) | 1998-09-01 |
US5969089A (en) | 1999-10-19 |
US5906783A (en) | 1999-05-25 |
KR20000065023A (en) | 2000-11-06 |
JPH11510549A (en) | 1999-09-14 |
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