EP0925323A1 - Verfahren zum herstellen von lösungen biologisch abbaubarer kunststoffe, insbesondere aliphatischer polyesteramide - Google Patents
Verfahren zum herstellen von lösungen biologisch abbaubarer kunststoffe, insbesondere aliphatischer polyesteramideInfo
- Publication number
- EP0925323A1 EP0925323A1 EP97942881A EP97942881A EP0925323A1 EP 0925323 A1 EP0925323 A1 EP 0925323A1 EP 97942881 A EP97942881 A EP 97942881A EP 97942881 A EP97942881 A EP 97942881A EP 0925323 A1 EP0925323 A1 EP 0925323A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- plastic
- solvent mixture
- aliphatic polyester
- solvent
- added
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 150000001408 amides Chemical class 0.000 title claims abstract description 16
- 229920003232 aliphatic polyester Polymers 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000011877 solvent mixture Substances 0.000 claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims abstract description 7
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims abstract description 3
- 230000001070 adhesive effect Effects 0.000 claims abstract description 3
- 239000004033 plastic Substances 0.000 claims description 29
- 229920003023 plastic Polymers 0.000 claims description 29
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 230000008961 swelling Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229920000704 biodegradable plastic Polymers 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical group 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 239000000123 paper Substances 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000002361 compost Substances 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003415 peat Substances 0.000 claims description 2
- 238000004382 potting Methods 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229920006238 degradable plastic Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- -1 Caprolacton etc. Chemical class 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229920000229 biodegradable polyester Polymers 0.000 description 2
- 239000004622 biodegradable polyester Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000011111 cardboard Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- VWTINHYPRWEBQY-UHFFFAOYSA-N denatonium Chemical compound [O-]C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C[N+](CC)(CC)CC(=O)NC1=C(C)C=CC=C1C VWTINHYPRWEBQY-UHFFFAOYSA-N 0.000 description 1
- 229960001610 denatonium benzoate Drugs 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- C08J3/095—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/12—Polyester-amides
Definitions
- the present invention relates to a method for producing solutions of biodegradable plastics, in particular aliphatic polyester amides, and to the use of the solution obtained for the production of films and for coating substrates made of metal, paper, wood, plastic, ceramic and foodstuffs.
- Plastics are widely used in the household, trade and industry, for example as moldings, foils and coatings. However, their disposal after use is an increasing problem. Therefore, biodegradable plastics have also been developed in recent years.
- polyester amides based on natural amino acids are known. They are manufactured using an elaborate protective group technique, since they are generally natural amino acids in combination with hydroxycarboxylic acids, which is very cumbersome. In addition, these polymers do not have any mechanical properties that are necessary for the production of consumer articles.
- polyesteramides made from lactic acid, diamines and dicarboxylic acid dichlorides are disclosed in US Pat. Nos. 4,343,931 and 4,529,792.
- Biodegradable polymers made from caprolactone and caprolactam are known from Japanese patents 79 113 593 and 79 109 594. knows.
- the polyester amides mentioned above are difficult to produce.
- polyester amide is disclosed in European patent application EP 641 817.
- the polyester amide described there can be processed thermoplastically and is biodegradable. It has a melting point of at least 75 ° C. and the proportion by weight of the ester structures is between 30 and 70% and the proportion of the amide structures is between 70 and 30%.
- the polymer described has good mechanical properties. The processability is very difficult. Molded articles can only be produced from the polymers in bulk. Solutions, for example in ethanol, are not stable and lead to the decomposition of the polymer within a short time.
- the object of the present invention is to produce solutions of biodegradable polyester amides in order to be able to make them easier and easier to process.
- the present invention relates to a method for producing solutions of biodegradable plastics, in particular aliphatic polyester amides, which is characterized in that the aliphatic polyester amide contains in a solvent mixture
- biodegradable aliphatic polyesteramides work well in the solvent mixture according to the invention, which contains components A, B and / or C contains, let solve. After just a few minutes, the polymer swells in the solution and dissolves. The dissolution rate can, if necessary, be increased by mechanical influences, such as stirring.
- the solution obtained is stable for several days without any degradation of the polymer structure being observed.
- the method detects the following steps
- the softened and swollen plastic is mechanically crushed and the emulsion formed is preferably filtered.
- the soaked and swollen plastic preferably filtered, the filtered solids can be fed to a new batch of plastic / solvent mixture.
- powdery plastic is introduced into a solvent with constant stirring so that it dissolves immediately and a coating can be carried out.
- the C - C alcohols of component A are preferably methanol and / or ethanol, it being preferred for ecological reasons to use methanol and ethanol obtained from vegetable raw materials.
- the solvent mixture preferably contains the C -C alcohol in an amount of 70 to 98.9% by weight, in particular in an amount of 90 to 98.9% by weight.
- Acetone and butanone have been found to be particularly suitable as C -Cr. Ketone.
- the ketone is preferably present in the solvent mixture in an amount of 0.1 to 5% by weight, preferably 0.1 to 2% by weight.
- benzoic acid and its derivatives i.e. Compounds in which the aromatic ring is substituted.
- Benzoates are preferably used, denatoniomobenzoate being particularly preferred.
- Component C is usually contained in the solvent mixture in an amount of 0.01 to 5 ppm.
- a preferably used polyester amide is made up of aliphatic monomers, in which the proportion by weight of the ester structure is between 30 and 70% and the proportion of the id structure is between 70 and 30%. So that the polymer can be used outdoors, ie also in the sun, the polyesteramide should have a melting point of at least 75 ° C. Polyesteramides such as those described in European patent application EP 0 641 817 have proven to be particularly suitable.
- the average molecular weight (Mw determined by chromatography in n-cresol against standard polystyrene) is from 10,000 to 300,000, preferably 20,000 to 150,000.
- the polyester amides preferably used can be obtained in a manner known per se, for example by mixing the amide or ester-forming starting components and subsequent polymerization.
- the synthesis can be carried out either by the "polyamide method” by stoechiometric mixing of the starting components, if appropriate with the addition of water and subsequent removal of water from the reaction mixture, or by the "polyester method” by adding an excess of diol with branching of the acid groups and subsequent esterification or transamidation of these esters.
- excess glycol is also distilled off in the water.
- polyesteramides can also be used in which the monomers are distributed as longer segments in the polymer molecule.
- polyester amides which are preferably used, the following are used as monomers, for example
- Dialcohols such as ethylene glycol, 1, 4-butanediol, 1, 3-butanediol, 1, 6-hexanediol, diethylene glycol, etc. and / or dicarboxylic acids such as oxalic acid, succinic acid, adipic acid and their lower alkyl esters, and / or hydroxycarboxylic acids and lactones, such as Caprolacton etc., and / or amino alcohols such as ethanolamine, propa- nolamine etc., and / or cyclic lactams such as e-caprolactam and laurolactam etc., and / or v-aminocarboxylic acids such as aminocaproic acid etc. and / or mixtures (lil salts) of dicarboxylic acids such as adipic acid, succinic acid etc. and diamines such as hexamethylene diamine, diaminobutane, etc.
- dicarboxylic acids such
- hydroxyl- or acid-terminated polyesters with molecular weights between 200 and 10,000 can also be used as the ester-forming component.
- the polyester amides obtained can further contain 0.1 to 5% by weight, preferably 0.1 to 2% by weight, of so-called branching agents.
- branching agents can e.g. trifunctional alcohols such as trimethyolpropane or glycerin, tetrafunctional alcohols such as pentaerythritol, trifunctional carboxylic acids such as citric acid.
- trifunctional alcohols such as trimethyolpropane or glycerin
- tetrafunctional alcohols such as pentaerythritol
- trifunctional carboxylic acids such as citric acid.
- the solvent mixture used according to the invention can contain, in addition to the above-mentioned components A, B and C, further constituents which improve the solubility of the polymers and, if appropriate, stabilize the solution.
- the mixture can also contain water in an amount of up to 30% by weight, preferably between 0.1 and 10% by weight.
- the films produced according to the invention offer a significantly more widespread application range for biodegradable polyester amides than the pure substances.
- films can be cast from the solutions. Clear, elastic films are obtained which can be produced in any thickness and can be used, for example, as compostable garbage bags or milk films.
- the films can contain any fillers, care should be taken to ensure that the compostability of the polymers is not impaired by these additives.
- fillers are talc, CaSO, for example gypsum, which is obtained during flue gas desulfurization, compost, peat, potting soil etc.
- the last-mentioned fillers enable the use of biodegradable polymers in agriculture and horticulture.
- Another possible use of the solution obtained according to the invention is the use for coating substrates of metal, paper, wood, plastic, ceramic and food. It can be used as a protective coating for metal substrates and glass as a protective coating during transport. Furthermore, paper or cardboard can be coated, for example, so that the mechanical properties of cardboard and paper and the resistance to moisture and water are increased, but the paper can be returned to the ecological cycle after use.
- the coating can take place, for example, in the immersion process, by application with a brush or in the spray process.
- the foils that are formed can be removed in their entirety in a very short time without leaving any residue.
- solutions obtained according to the invention is as an adhesive.
- the solutions in concentrated form are applied to the surfaces or points to be connected, after a short flash-off time, which serves to evaporate the solvent mixture, the surfaces are pressed together.
- BAK 1095 (commercial product from Bayer AG, Leverkusen) was used as the polymer. BAK 2195 can also be used.
- Example 2t
- 300 g of the polymer are placed in a beaker.
- the solvent mixture is added and the mixture is left in a closed vessel in which a vacuum is drawn for 24 hours without heating until an increase in volume and color change in the plastic are found.
- the plastic is again covered with solvent and then left to stand for about 24 hours with the beaker closed.
- BAK 1095 was used as the plastic.
- BAK 2195 can also be used.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Biological Depolymerization Polymers (AREA)
Abstract
Description
Claims
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19636984 | 1996-09-11 | ||
| DE19636984 | 1996-09-12 | ||
| DE19640032 | 1996-09-27 | ||
| DE19640032A DE19640032A1 (de) | 1996-09-11 | 1996-09-27 | Verfahren zum Herstellen von Lösungen biologisch abbaubarer Kunststoffe, insbesondere aliphatischer Polyesteramide |
| PCT/EP1997/004662 WO1998011153A1 (de) | 1996-09-11 | 1997-08-27 | Verfahren zum herstellen von lösungen biologisch abbaubarer kunststoffe, insbesondere aliphatischer polyesteramide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0925323A1 true EP0925323A1 (de) | 1999-06-30 |
Family
ID=26029270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP97942881A Ceased EP0925323A1 (de) | 1996-09-11 | 1997-08-27 | Verfahren zum herstellen von lösungen biologisch abbaubarer kunststoffe, insbesondere aliphatischer polyesteramide |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0925323A1 (de) |
| AU (1) | AU4455997A (de) |
| WO (1) | WO1998011153A1 (de) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL180951B1 (pl) * | 1992-12-04 | 2001-05-31 | Khashoggi E Ind | Sposób co najmniej jednostronnego, ewentualnie od strony wewnętrznej, nieprzemakalnego powlekania kształtek na bazie skrobi |
| DE4327024A1 (de) * | 1993-08-12 | 1995-02-16 | Bayer Ag | Thermoplastisch verarbeitbare und biologisch abbaubare aliphatische Polyesteramide |
| EP0731127A3 (de) * | 1995-03-09 | 1998-03-04 | Sekisui Kaseihin Kogyo Kabushiki Kaisha | Aliphatische Ester-Amid Copolymerharze |
-
1997
- 1997-08-27 WO PCT/EP1997/004662 patent/WO1998011153A1/de not_active Ceased
- 1997-08-27 EP EP97942881A patent/EP0925323A1/de not_active Ceased
- 1997-08-27 AU AU44559/97A patent/AU4455997A/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9811153A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4455997A (en) | 1998-04-02 |
| WO1998011153A1 (de) | 1998-03-19 |
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