CA2489795C - Copolymerization of cyclic ester oligomers - Google Patents
Copolymerization of cyclic ester oligomers Download PDFInfo
- Publication number
- CA2489795C CA2489795C CA2489795A CA2489795A CA2489795C CA 2489795 C CA2489795 C CA 2489795C CA 2489795 A CA2489795 A CA 2489795A CA 2489795 A CA2489795 A CA 2489795A CA 2489795 C CA2489795 C CA 2489795C
- Authority
- CA
- Canada
- Prior art keywords
- cyclic ester
- copolyester
- derived
- acid
- encapsulated
- 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
- -1 cyclic ester Chemical class 0.000 title claims abstract description 27
- 238000007334 copolymerization reaction Methods 0.000 title description 11
- 229920001634 Copolyester Polymers 0.000 claims abstract description 37
- 238000000576 coating method Methods 0.000 claims abstract description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 34
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 28
- 238000002844 melting Methods 0.000 claims description 27
- 230000008018 melting Effects 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 20
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 14
- 230000004927 fusion Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 6
- 229940043375 1,5-pentanediol Drugs 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 229940106691 bisphenol a Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002531 isophthalic acids Chemical class 0.000 claims description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical class C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003504 terephthalic acids Chemical class 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 150000001279 adipic acids Chemical class 0.000 claims 1
- 235000011044 succinic acid Nutrition 0.000 claims 1
- 150000003444 succinic acids Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 13
- 238000005809 transesterification reaction Methods 0.000 abstract description 4
- 239000008393 encapsulating agent Substances 0.000 abstract description 2
- 238000012163 sequencing technique Methods 0.000 abstract 1
- 239000000539 dimer Substances 0.000 description 7
- 125000000743 hydrocarbylene group Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000013638 trimer Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YWFUVTMPYOLBDB-UHFFFAOYSA-M butyl(chloro)tin;dihydrate Chemical compound O.O.CCCC[Sn]Cl YWFUVTMPYOLBDB-UHFFFAOYSA-M 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009897 systematic effect Effects 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- SLGGJMDAZSEJNG-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;terephthalic acid Chemical compound OCCOCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 SLGGJMDAZSEJNG-UHFFFAOYSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- XXWVVIRTHDRMEY-UHFFFAOYSA-N bromo thiohypobromite Chemical compound BrSBr XXWVVIRTHDRMEY-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004943 liquid phase epitaxy Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from 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
- C08G63/02—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
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/34—Oligomeric, e.g. cyclic oligomeric
-
- 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
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
-
- 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
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39555702P | 2002-07-12 | 2002-07-12 | |
| US60/395,557 | 2002-07-12 | ||
| PCT/US2003/021742 WO2004007589A1 (en) | 2002-07-12 | 2003-07-11 | Copolymerization of cyclic ester oligomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2489795A1 CA2489795A1 (en) | 2004-01-22 |
| CA2489795C true CA2489795C (en) | 2012-02-21 |
Family
ID=30115885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2489795A Expired - Fee Related CA2489795C (en) | 2002-07-12 | 2003-07-11 | Copolymerization of cyclic ester oligomers |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6806346B2 (https=) |
| EP (1) | EP1521792B1 (https=) |
| JP (1) | JP2006511631A (https=) |
| CN (1) | CN1668666A (https=) |
| AU (1) | AU2003249057A1 (https=) |
| CA (1) | CA2489795C (https=) |
| DE (1) | DE60322062D1 (https=) |
| WO (1) | WO2004007589A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7151143B2 (en) | 2000-01-21 | 2006-12-19 | Cyclics Corporation | Blends containing macrocyclic polyester oligomer and high molecular weight polymer |
| US7256241B2 (en) | 2000-01-21 | 2007-08-14 | Cyclics Corporation | Methods for polymerizing macrocyclic polyester oligomers using catalyst promoters |
| US6960626B2 (en) | 2000-01-21 | 2005-11-01 | Cyclics Corporation | Intimate physical mixtures containing macrocyclic polyester oligomer and filler |
| US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
| EP1313789B1 (en) | 2000-09-01 | 2006-07-19 | Cyclics Corporation | Methods for converting linear polyesters to macrocyclic oligoester compositions and macrocyclic oligoesters |
| US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
| US20080129588A1 (en) | 2001-06-06 | 2008-06-05 | David Albert Lundgren | Method and apparatus for determining location information of a mobile device |
| JP3952706B2 (ja) * | 2001-06-14 | 2007-08-01 | 富士ゼロックス株式会社 | 高分子化合物及びその製造方法、成形体及びその製造方法 |
| ES2250687T3 (es) | 2001-06-27 | 2006-04-16 | Cyclics Corporation | Aislamiento, formulacion, y moldeo de oligoesteres macrociclicos. |
| US7304123B2 (en) | 2001-06-27 | 2007-12-04 | Cyclics Corporation | Processes for shaping macrocyclic oligoesters |
| US6787632B2 (en) | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
| US7403261B2 (en) | 2004-12-15 | 2008-07-22 | Asml Netherlands B.V. | Lithographic apparatus and device manufacturing method |
| US20080227925A1 (en) * | 2007-03-14 | 2008-09-18 | Pretzer Wayne R | Composition containing macrocyclic ethylene isophthalate dimer and process of making |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419507A (en) | 1982-01-25 | 1983-12-06 | Eastman Kodak Company | Copolyester adhesives |
| US5466744A (en) | 1990-11-05 | 1995-11-14 | General Electric Company | Polymerization of macrocyclic poly(alkylene dicarboxylate) oligomers |
| US5039783A (en) | 1990-11-05 | 1991-08-13 | General Electric Company | Method for preparing and polymerizing macrocyclic poly(alkylene discarboxylate) oligomers |
| US5214158A (en) | 1991-06-03 | 1993-05-25 | General Electric Company | Method for preparation of macrocyclic poly(alkylene dicarboxylate) oligomers |
| US5300590A (en) * | 1992-11-30 | 1994-04-05 | General Electric Company | Macrocyclic polyester compositions convertible to linear polyesters of improved integrity |
| EP0655476A1 (en) * | 1993-11-29 | 1995-05-31 | General Electric Company | Fibrous preforms containing cyclic polyester oligomers |
| US5527976A (en) * | 1995-01-12 | 1996-06-18 | General Electric Company | Method for polymerizing macrocyclic poly(alkylene dicarboxylate) oligomers |
| US5648454A (en) | 1996-02-14 | 1997-07-15 | General Electric Company | Process for producing high ductile polyesters |
| US5661214A (en) | 1996-08-05 | 1997-08-26 | General Electric Company | Titanate esters useful as polymerization initiators for macrocylic polyester oligomers |
| US6376026B1 (en) * | 1999-12-20 | 2002-04-23 | Rohm And Haas Company | Method of coating with powders comprising macrocyclic oligomers |
| US6420047B2 (en) | 2000-01-21 | 2002-07-16 | Cyclics Corporation | Macrocyclic polyester oligomers and processes for polymerizing the same |
| JP4119368B2 (ja) * | 2001-10-22 | 2008-07-16 | エスケー ケミカルズ カンパニー リミテッド | 溶剤型コーティング用共重合ポリエステル樹脂およびそれを含むコーティング組成物 |
| ITMI20020864A1 (it) * | 2002-04-22 | 2003-10-22 | Novamont Spa | Copolimeri a blocchi amorfo-cristallini |
| EP1484371A3 (en) * | 2003-06-05 | 2005-02-09 | Rohm And Haas Company | Degradable powder coatings, methods and apparatus for powder coating biodegradable substrates and products produced thereby |
-
2003
- 2003-07-09 US US10/616,168 patent/US6806346B2/en not_active Expired - Lifetime
- 2003-07-11 EP EP03764516A patent/EP1521792B1/en not_active Expired - Lifetime
- 2003-07-11 JP JP2004521687A patent/JP2006511631A/ja active Pending
- 2003-07-11 DE DE60322062T patent/DE60322062D1/de not_active Expired - Lifetime
- 2003-07-11 AU AU2003249057A patent/AU2003249057A1/en not_active Abandoned
- 2003-07-11 CN CN03816641.0A patent/CN1668666A/zh active Pending
- 2003-07-11 CA CA2489795A patent/CA2489795C/en not_active Expired - Fee Related
- 2003-07-11 WO PCT/US2003/021742 patent/WO2004007589A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN1668666A (zh) | 2005-09-14 |
| EP1521792A1 (en) | 2005-04-13 |
| AU2003249057A1 (en) | 2004-02-02 |
| JP2006511631A (ja) | 2006-04-06 |
| DE60322062D1 (de) | 2008-08-21 |
| US6806346B2 (en) | 2004-10-19 |
| EP1521792B1 (en) | 2008-07-09 |
| US20040054124A1 (en) | 2004-03-18 |
| CA2489795A1 (en) | 2004-01-22 |
| WO2004007589A1 (en) | 2004-01-22 |
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