WO2006097354A1 - Biodegradable aliphatic-aromatic copolyester - Google Patents
Biodegradable aliphatic-aromatic copolyester Download PDFInfo
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- WO2006097354A1 WO2006097354A1 PCT/EP2006/002672 EP2006002672W WO2006097354A1 WO 2006097354 A1 WO2006097354 A1 WO 2006097354A1 EP 2006002672 W EP2006002672 W EP 2006002672W WO 2006097354 A1 WO2006097354 A1 WO 2006097354A1
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- 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
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- 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
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- 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
- C08G63/91—Polymers modified by chemical after-treatment
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- 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
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
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- 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
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/02—Starch; Degradation products thereof, e.g. dextrin
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1328—Shrinkable or shrunk [e.g., due to heat, solvent, volatile agent, restraint removal, etc.]
- Y10T428/1331—Single layer [continuous layer]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1334—Nonself-supporting tubular film or bag [e.g., pouch, envelope, packet, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Definitions
- the present invention relates to a biodegradable aliphatic-aromatic polyester (AAPE) obtained from an aliphatic acid at least 70% of which is sebacic acid, at least a polyfunctional aromatic acids and at least a dialcohol, as well as to mixtures of said polyesters with other biodegradable polymers both of natural origin and of synthetic origin.
- AAPE biodegradable aliphatic-aromatic polyester
- Biodegradable aliphatic-aromatic polyesters obtained from dicarboxylic acids and dialcohols are known in the literature and are commercially available.
- the presence of the aromatic component in the polyester chain is important to obtain polymers with sufficiently high melting points and with adequate crystallization rates .
- polyesters of this sort are currently commercially available, the amount of aromatic acid in the chain is typically lower than 49% since the above said threshold, the percentage of biodegradation of the polyesters decreases significantly above said threshold.
- an increase in the percentage of aromatic acid in the chain would, however, be desirable in so far as it would enable an increase in the melting point of the polyester, an increase in, or at least a maintenance of, important mechanical properties, such as ultimate strength and elastic modulus, and would moreover enable an increase in the crystallization rate of the polyester, thereby improving its industrial processability .
- a further drawback of biodegradable aliphatic-aromatic polyesters that are currently commercially available is represented by the fact that the monomers of which they are constituted come from nonrenewable sources, thereby maintaining a significant environmental impact associated to the production of such polyesters despite their biodegradability. They have far more energy content than LDPE and HDPE particularly in the presence of adipic acid.
- the use of monomers of vegetal origin would contributeto the reduction of emission of CO 2 in the atmosphere and to the reduction in the use of monomers derived from non-renewable resources.
- Patent 4,966,959 discloses certain copolyesters comprising from 60 to 75% mol of terephtalic acid, 25 to 40% mol of a carboxylic aliphatic or cycloaliphatic acid, and a glycol component.
- the inherent viscosity of such polyesters is from about 0.4 to about 0.6, rendering the polyesters useful as adhesives but unsuitable for many other applications.
- U.S. Patent 4,398,022 discloses copolyesters comprising terephtalic acid and 1, 12-dodecanedioic acid and a glycol component comprising 1, 4-cyclohexanedimethanol .
- the acid component may optionally include one or more acids conventionally used in the production of polyesters, but the examples show that 1, 12-dodecanedioic acid must be present for the polyesters to have the desired melt strength.
- U.S. Patent 5,559,171 discloses binary blends of cellulose esters and aliphatic-aromatic copolyesters .
- the AAPE component of such blends comprises a moiety derived from a C 2 -C 14 aliphatic diacid which can range from 30 to 95 % mol in the copolymer, a moiety derived from an aromatic acid which can range from 70 to 5 % mol in the copolymer.
- Certain AAPEs disclosed in this document do not require blending and are useful in film application. They comprise a moiety derived from a C 2 -C 10 aliphatic diacid which can range from 95 to 35 % mol in the copolymer, and a moiety derived from an aromatic acid which can range from 5 to 65 % mol in the copolymer.
- AAPE terephtalic acid, an aliphatic diacid and a diol component.
- the weight average molecular weight M w of such AAPEs is always very low (maximum 51000 g/mol) , so that their industrial applicability is limited. It is therefore the overall object of the present invention to disclose an improved AAPE and blends containing the same.
- the present invention regards a biodegradable aliphatic/aromatic copolyester (AAPE) comprising:
- AAPE butandiol
- said AAPE being biodegradable according to the Standard ISO 14855 Amendment 1 of more than 40%, preferably more than 60%, in 30 days, with respect to cellulose used as reference, and having: a density of less than 1.22 g/cc, preferably less than 1,21 g/cc, and more preferably less than 1.20 g/cc; a number average molecular weight M n of 40,000 - 140,000 an inherent viscosity of 0.8 - 1.5.
- polyfunctional aromatic acids for the purposes of the present invention are meant aromatic dicarboxylic compounds of the phthalic- acid type and their esters, preferably terephthalic acid.
- the content of aromatic dicarboxylic acid in the biodegradable polyester according to the claims of the present invention is 49 to 66 mol % and preferably 49,5 - 63, more preferably 50 - 61 % with respect to the total molar content of the acid component .
- the molecular weight M n of the polyester according to the present invention is between 40 000 and 140 000.
- the polydispersity index M w / M n determined by means of gel -permeation chromatography (GPC) is between 1.7 and 2.6, preferably between 1.8 and 2.5.
- the polyester according to the invention is characterized from being rapidly crystallizable and has a crystallization temperature T c higher than 30° C, preferably higher than 40° C.
- the polyester according to the invention has an inherent viscosity (measured with Ubbelhode viscosimeter for solutions in CHCl 3 of a concentration of 0.2 g/dl at 25 0 C) of between 0.8 dl/g and 1.5 dl/g, preferably between 0.83 dl/g and 1.3 dl/g and even more preferably between 0.85 dl/g and 1.2 dl/g.
- the Melt Flow Rate (MFR) of the polyester according to the invention in the case of use for applications typical of plastic materials (such as, for example, bubble filming, injection moulding, foams, etc.), is between 0.5 and 100 g/10 min, preferably between 1.5 - 70 g/10 min, more preferably between 2.0 and 50 g/10 min (measurement made at 190°C/2.16 kg according to the ASTM D1238 standard) .
- the polyester has a density measured with a Mohr-Westphal weighing machine of less than 1.22 g/crn2, preferably less than 1.21 g/cm2 and even more preferably less than 1.20 g/cm2.
- the polyester according to the present invention shows a energy at break higher than 80 MJ/m2 preferably higher than 100 MJ/m 2 and -a Elastic Modulus higher than 75 MPa.
- the polyester according to the present invention show an Elmendorf tear strength (determined according to the standard ASTM D1922-89 and measured on blown film filmed with a blowing ratio of 2 - 3 and a draw down ratio of 7 - 14) higher than 20 N/mm, preferably higher than 25 N/mm, in the longitudinal direction and higher than 60 N/mm, preferably higher than 65 N/mm, for the quantity:
- one or more polyfunctional molecules in amounts of between 0.02 - 3.0 mol% preferably between 0.1 mol% and 2.5 with respect to the amount of dicarboxylic acids (as well as to the possible hydroxy acids) , can advantageously be added in order to obtain branched products.
- Examples of these molecules are glycerol, pentaerythritol, trimethylol propane, citric acid, dipentaerythritol , monoanhydrosorbitol, monohydromannitol, epoxidized oils such as epoxidized soybean oil, epoxidized linseed oil and so on, dihydroxystearic acid, itaconic acid and so on .
- polymer according to the present invention reach high levels of performance without any need to add chain extenders such as di and/or poly isocyanates and isocyanurates, di and/or poly epoxides, bis-oxazolines or poly carbodimides or divinylethers , it is in any case possible to modify the properties thereof as the case may require .
- chain extenders such as di and/or poly isocyanates and isocyanurates, di and/or poly epoxides, bis-oxazolines or poly carbodimides or divinylethers
- additives are used in percentages comprised between 0.05 - 2.5%, preferably 0.1 - 2.0%.
- specific catalysts can be used such as for example zinc stearates (metal salts of fatty acids) for poly epoxides .
- the increase in the molecular weight of the polyester can advantageously be obtained, for example, by addition of various organic peroxides during the process of extrusion.
- the increase in molecular weight of the biodegradable polyester can be easily detected by observing the increase in the values of viscosity following upon treatment of the polyesters with peroxides.
- the addition of the above mentioned chain extenders according to the teaching of EP 1 497 370 results in a production of a gel fraction lower than 4.5% w/w with respect to the polyester.
- the content of EP 1 497 370 has to be intended as incorporated by reference in the present description.
- polyester according to the invention present properties and values of viscosity that render them suitable for use, by appropriately modulating the relative molecular weight, in numerous practical applications, such as films, injection-moulded products, extrusion-coating products, fibres, foams, thermoformed products, extruded profiles and sheets, extrusion blow molding, injection blow molding, rotomolding, stretch blow molding etc.
- films production technologies like film blowing, casting, coextrusion can be used. Moreover such films can be subject to biorientation in line or after film production.
- the films can be also oriented through stretching in one direction with a stretching ratio from 1:2 up to 1:15, more preferably from 1:2,2 up to 1:8. It is also possible that the stretching is obtained in presence of an highly filled material with inorganic fillers. In such a case, the stretching can generate microholes and the so obtained film can be particularly suitable for hygiene applications.
- polyester according to the invention is suitable for the production of :
- - films for use in the agricultural sector as mulching films; -cling films (extensible films) for foodstuffs, for bales in the agricultural sector and for wrapping of refuse;
- - shrink film such as for example for pallets, mineral water, six pack rings, and so on;
- thermoformed single-layer and multilayer packaging for foodstuffs such as for example containers for milk, yoghurt, meat, beverages, etc . ;
- the polyester according to the invention can also be used in blends with polymers of natural origin, such as for example starch, cellulose, chitosan, alginates, natural rubbers or natural fibers (such as for example jute, kenaf, hemp)
- the starches and celluloses can be modified, and amongst these starch or cellulose esters with a degree of substitution of between 0.2 and 2.5, hydroxypropylated starches, and modified starches with fatty chains may, for example, be mentioned.
- Preferred esters are acetates, propionates, butyrrates and their combinations.
- Starch can moreover be used both in its destructurized form and in its gelatinized form or as filler. Mixtures of the AAPE according to the invention with starch are particularly preferred.
- compositions which comprise thermoplastic starch and a thermoplastic polymer incompatible with starch, starch constitutes the dispersed phase and the AAPE thermoplastic polymer constitutes the continuous phase.
- thermoplastic starch constitutes the dispersed phase and the AAPE thermoplastic polymer constitutes the continuous phase.
- starch/polyester copolymers through transesterification catalysts .
- Such polymers can be generated trough reactive blending during compounding or can be produced in a separate process and then added during extrusion.
- block copolymers of an hydrophilic and an hydrophobic units are particularly suitable.
- Additives such as di and polyepoxides , di and poly isocyanates, isocyanurates, polycarbodiimmides and peroxides can also be added. They can work as stabilizers as well as chain extenders. All the products above can help to create the needed microstructure . It is also possible to promote in situ reactions to create bonds between starch and the polymeric matrix.
- Particularly resistant and easily processable compounds contain destructurized starch in combination with the polyesters of the invention and polylactic acid polymers and copolymers with and without additives such as polyepoxydes , carbodiimmides and/or peroxides .
- starch-polyester compositions block copolymers with hydrophobic and hydrophilic units.
- Possible examples are polyvynilacetate/polyvinylalcohol and polyester/polyether copolymers in which the block length, the balance between the hydrophilicity and hydrophobicity of the blocks and the quality of compatibilizer used can be suitably changed in order to finely adjust the microstructure of the starch-polyester compositions .
- -MFR was measured in the conditions envisaged by the ASTM D1238-89 standard at 150 0 C and 5 kg or at 190 0 C and 2.16 kg;
- W a weight of the sample in air
- W f1 weight of the sample in alcohol
- Example 1 The process of Example 1 was repeated with: 2480 g of terephthalic acid (14.9 mol), 3400 g of sebacic acid (16.8 mol), 3430 g butandiol (38.1 mol), 6.1 g of butylstannoic acid.
- Example 5 (comparison) The process of Example 1 was repeated with:
- the molar percentage of aromatic content with respect to the sum of the acids was 54 mol%.
- Example 1 The process of Example 1 was repeated with:
- the molar percentage of aromatic content with respect to the sum of the acids was 60 mol%.
- Example 1 The process of Example 1 was repeated with: 3858,7 g of dimethyl terephthalate ( 19,89 mol), 3526,4 g of butandiol (39,18 mol), 2070,5 g of sebacic acid ( 10,25 mol) .
- the molar percentage of aromatic content with respect to the sum of the acids was 66 mol%.
- the blow up ratio was 2.5 whereas the draw down ratio was 10.
- the films thus obtained had a thickness of approximately 30 ⁇ .
- a week after filming, and after conditioning at 25°C, with 55% relative humidity, the tensile properties were measured according to the ASTM D882-88 standards.
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
- Woven Fabrics (AREA)
- Wrappers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Nonwoven Fabrics (AREA)
- Laminated Bodies (AREA)
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- Absorbent Articles And Supports Therefor (AREA)
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Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20060723662 EP1863860B1 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
DE200660003078 DE602006003078D1 (en) | 2005-03-18 | 2006-03-17 | BIODEGRADABLE ALIPHATIC AROMATIC COPOLYESTER |
JP2008501246A JP5264474B2 (en) | 2005-03-18 | 2006-03-17 | Biodegradable fat-aromatic polyester |
PL06723662T PL1863860T3 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
CN2006800087776A CN101283020B (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic polyesters |
US11/909,049 US8193300B2 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
CA 2601183 CA2601183C (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
US13/465,643 US8461273B2 (en) | 2005-03-18 | 2012-05-07 | Biodegradable aliphatic-aromatic copolyester |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI2005A000452 | 2005-03-18 | ||
ITMI20050452 ITMI20050452A1 (en) | 2005-03-18 | 2005-03-18 | ALYPATIC-AROMATIC BIODEGRADABLE POLYESTER |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/909,049 A-371-Of-International US8193300B2 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
US13/465,643 Division US8461273B2 (en) | 2005-03-18 | 2012-05-07 | Biodegradable aliphatic-aromatic copolyester |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006097354A1 true WO2006097354A1 (en) | 2006-09-21 |
Family
ID=35149279
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2006/002673 WO2006097355A1 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
PCT/EP2006/002670 WO2006097353A1 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic -aromatic polyesters |
PCT/EP2006/002674 WO2006097356A1 (en) | 2005-03-18 | 2006-03-17 | Biodegaradable aliphatic-aromatic polyester |
PCT/EP2006/002672 WO2006097354A1 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2006/002673 WO2006097355A1 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic-aromatic copolyester |
PCT/EP2006/002670 WO2006097353A1 (en) | 2005-03-18 | 2006-03-17 | Biodegradable aliphatic -aromatic polyesters |
PCT/EP2006/002674 WO2006097356A1 (en) | 2005-03-18 | 2006-03-17 | Biodegaradable aliphatic-aromatic polyester |
Country Status (21)
Country | Link |
---|---|
US (8) | US8193300B2 (en) |
EP (6) | EP2163567B1 (en) |
JP (3) | JP5264474B2 (en) |
KR (1) | KR101216846B1 (en) |
CN (5) | CN103087299B (en) |
AT (4) | ATE462744T1 (en) |
AU (1) | AU2006224682B2 (en) |
BR (1) | BRPI0611457B1 (en) |
CA (4) | CA2601183C (en) |
DE (3) | DE602006013287D1 (en) |
EG (1) | EG25733A (en) |
ES (6) | ES2661949T3 (en) |
HK (3) | HK1118845A1 (en) |
IT (1) | ITMI20050452A1 (en) |
MX (1) | MX2007011496A (en) |
NO (1) | NO344336B1 (en) |
PL (6) | PL2287224T3 (en) |
RU (1) | RU2415879C2 (en) |
TR (1) | TR201803019T4 (en) |
UA (1) | UA89401C2 (en) |
WO (4) | WO2006097355A1 (en) |
Cited By (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010012695A1 (en) | 2008-08-01 | 2010-02-04 | Basf Se | Increasing the hydrolysis resistance of biodegradable polyesters |
WO2012019868A2 (en) | 2010-07-19 | 2012-02-16 | Basf Se | Method for increasing the molecular weight of polyesters |
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