WO2017152678A1 - 一种可生物降解聚酯组合物 - Google Patents
一种可生物降解聚酯组合物 Download PDFInfo
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- WO2017152678A1 WO2017152678A1 PCT/CN2016/110000 CN2016110000W WO2017152678A1 WO 2017152678 A1 WO2017152678 A1 WO 2017152678A1 CN 2016110000 W CN2016110000 W CN 2016110000W WO 2017152678 A1 WO2017152678 A1 WO 2017152678A1
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- polyester composition
- biodegradable polyester
- cyclopentanone
- ppm
- biodegradable
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
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- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
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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
- 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
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/04—Starch derivatives, e.g. crosslinked derivatives
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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
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2467/04—Polyesters derived from hydroxy carboxylic 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
- C08L2201/00—Properties
- C08L2201/06—Biodegradable
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
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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
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Definitions
- the invention belongs to the field of polymer material modification, and in particular relates to a biodegradable polyester composition having excellent bubble stability.
- Biodegradable polyester is a kind of polymer material which is made from biological resources. Compared with petroleum-based polymers based on petrochemical resources, biodegradable polyesters can be degraded in biological or biochemical processes or in biological environments. It is currently the most active and market-based degradation in biodegradable plastics research. One of the materials.
- Biodegradable polyester film is one of the important application fields of biodegradable polyester, including food bags, garbage bags, shopping bags and plastic film.
- the biodegradable polyester In the process of preparing a film by blow molding, the biodegradable polyester often has a phenomenon that the film is not sufficiently lubricated and adhered to the roller or is too lubricious to be wound up, resulting in poor bubble stability during film blowing, and the film thickness is extremely poor. The phenomenon has seriously affected the continuity of the blown film.
- Patent CN 101622311A by adding 0.05-5 wt% biodiesel to the biodegradable polyester mixture, by reducing the viscosity of the polyester mixture, to some extent, the film sticks to the roller, thereby ensuring continuous film blowing. Sex.
- the decrease in the viscosity of the polyester mixture indicates that the addition of biodiesel impairs the properties of the polyester to some extent, resulting in an increase in the melting index of the polyester mixture and a decrease in viscosity.
- biodegradable polyesters have significantly improved blown film properties by the addition of trace amounts of cyclopentanone, and films are blown at higher speeds.
- the foam stability is good, and the thickness of the film is extremely small, which ensures the continuity of the blown film production.
- a biodegradable polyester composition comprising, by weight, components:
- the cyclopentanone is contained in an amount of from 0.5 ppm to 85 ppm, preferably from 5 ppm to 50 ppm, more preferably from 10 ppm to 35 ppm, based on the total mass of the biodegradable polyester composition.
- the biodegradable polyester composition comprises, by weight, components:
- the weight content of the cyclopentanone of the present invention is tested by accurately weighing 1.2000 g of the biodegradable polyester composition into a static headspace test bottle and testing the ring of the biodegradable polyester composition by a static headspace method.
- the peak area of pentanone can be calculated from the peak area of cyclopentanone in the biodegradable polyester composition and the cyclopentanone standard curve to calculate the content of cyclopentanone in the biodegradable polyester composition; the standard curve is from cyclopentanone / Calibration of methanol solution.
- the biodegradable aliphatic-aromatic polyester is polybutylene terephthalate PBAT, polysuccinate terephthalate PBST or polysebacate terephthalate.
- cyclopentanone to the biodegradable polyester can act like a lubricant, but if the content of cyclopentanone in the biodegradable polyester composition is too high, the film is too lubricated during high-speed film blowing, resulting in The film does not wind up well on the roll, which also causes the bubble to become unstable.
- the present inventors have found that controlling the content of cyclopentanone in the biodegradable polyester composition at 0.5 ppm to 85 ppm can improve the degree of lubrication of the biodegradable polyester during the blow molding process, at the film blowing speed.
- the film thickness is extremely poor ⁇ 0.2 ⁇ m, and the film thickness relative deviation is ⁇ 1%, which ensures the stability of the bubble and the continuity of the blown film.
- the weight content of cyclopentanone is preferably from 5 ppm to 50 ppm, more preferably from 10 ppm to 35 ppm, based on the total weight of the biodegradable polyester composition.
- the organic filler is selected from one of natural starch, plasticized starch, modified starch, natural fiber or wood flour or a mixture thereof;
- the inorganic filler is selected from the group consisting of talc, montmorillonite, kaolin, chalk, calcium carbonate, graphite, gypsum, conductive carbon black, calcium chloride, iron oxide, dolomite, silica, wollastonite, titanium dioxide, silicic acid.
- talc montmorillonite
- kaolin chalk
- calcium carbonate graphite
- gypsum conductive carbon black
- calcium chloride iron oxide
- dolomite silica
- wollastonite titanium dioxide
- silicic acid silicic acid.
- salt mica, fiberglass or mineral fiber or a mixture thereof.
- the route of obtaining the cyclopentanone of the present invention can be directly added to the cyclopentanone during the blending and extrusion process of the biodegradable polyester composition.
- the biodegradable polyester composition of the present invention may further comprise 0 to 4 parts of at least one of the following materials: a plasticizer, a mold release agent, a surfactant, a wax, an antistatic agent, according to different needs of the use. Dyes, UV absorbers, UV stabilizers or other plastic additives.
- the plasticizer is one or a mixture of two or more of citrate, glycerin, epoxidized soybean oil or the like;
- the release agent is one of silicone oil, paraffin wax, white mineral oil, petrolatum or a mixture of two or more;
- the surfactant is one or a mixture of two or more of polysorbate, palmitate or laurate;
- the wax is one or a mixture of two or more of erucamide, stearic acid amide, behenic acid amide, beeswax or beeswax;
- the antistatic agent is a permanent antistatic agent, and specifically one of PELESTAT-230, PELESTAT-6500, SUNNICO ASA-2500 or a mixture of two or more;
- the dye is one of carbon black, black species, titanium white powder, zinc sulfide, indigo blue, fluorescent orange or a mixture of two or more.
- the UV absorber is one or more of UV-944, UV-234, UV531, UV326;
- the UV stabilizer is one or more of UV-123, UV-3896, UV-328;
- the other plastic additive may be a nucleating agent, an antifogging agent, or the like;
- the biodegradable polyester composition of the invention can be used for preparing shopping bags, compost bags, mulch films, protective covering films, silo films, film strips, fabrics, non-woven fabrics, textiles, fishing nets, load-bearing bags, garbage bags, etc. .
- the invention has the following beneficial effects:
- the present invention can improve the degree of lubrication of the biodegradable polyester composition during the blow molding process by adding cyclopentanone to the composition and controlling the content of the cyclopentanone in the composition to be in the range of 0.5 ppm to 85 ppm.
- the film speed is 176 Kg/h
- the film thickness is extremely poor ⁇ 0.2 ⁇ m
- the film thickness relative deviation is ⁇ 1%, which has excellent bubble stability and ensures the continuity of the blown film.
- i) selects PBAT; component iv) selects ADR4370; organic filler selects starch; inorganic filler selects talc powder, calcium carbonate; plasticizer selects citric acid ester; surfactant selects palmitate; wax selects erucic acid Amide; the above auxiliary agents, PBAT, ADR4370, PLA, and cyclopentanone are all commercially available.
- the bubble stability during the blown film process of the biodegradable polyester composition is determined by the extremely poor thickness of the film and the relative deviation of the thickness of the film.
- the film thickness was measured by a spiral micrometer: 10 measurement points were uniformly taken on a film of 1 m*1 m for measurement.
- the film thickness difference is the difference between the maximum thickness value and the minimum thickness value among the 10 measurement points.
- the relative deviation of the film thickness is calculated by the following formula:
- cyclopentanone methanol solution Preparation of cyclopentanone methanol solution at concentrations of 0.0001 g/L, 0.001 g/L, 0.01 g/L, 0.1 g/L, 5.0 g/L, 10.0 g/L, 20.0 g/L, respectively, by static headspace method
- the peak areas of cyclopentanone in the above different concentrations of cyclopentanone methanol solution were tested, and the standard curve of cyclopentanone was prepared by taking the peak area of cyclopentanone as the ordinate and the concentration of cyclopentanone as the abscissa.
- the static headspace test conditions are as follows:
- Heating box 105 ° C
- the content of cyclopentanone in the biodegradable polyester composition in the examples was 0.5 to 85 ppm, and when the film blowing speed was 176 kg/h, the film thickness was extremely poor ⁇ 0.2 ⁇ m, and the film thickness was relatively The deviation ⁇ 1% indicates that the composition has better bubble stability, while the comparative example 1 does not add cyclopentanone.
- the content of cyclopentanone in the comparative example 2 exceeds 85 ppm, the film thickness is extremely poor > 0.2 ⁇ m, and the film thickness is relatively different. >1% indicates that the composition is unstable.
- the film blowing speed of Comparative Example 3 was lower than 176 Kg/h, the film blowing speed of Comparative Example 4 was higher than 176 Kg/h, the film thickness was extremely poor > 0.2 ⁇ m, the relative deviation of the film thickness was >1%, and the bubble of the composition was also less. stable.
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- Engineering & Computer Science (AREA)
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Abstract
Description
Claims (8)
- 一种可生物降解聚酯组合物,其特征在于,按重量份计,包括组分:i)60至99份的可生物降解的脂族-芳族聚酯;ii)0至40份的聚乳酸;iii)0至30份的有机填料和/或无机填料;iv)0至1份的含有环氧基团且基于苯乙烯、丙烯酸酯和/或甲基丙烯酸酯的共聚物。
- 根据权利要求1所述的一种可生物降解聚酯组合物,其特征在于,基于可生物降解聚酯组合物的总重量计,环戊酮的重量含量为0.5ppm-85ppm,优选为5ppm-50ppm,更优选为10ppm-35ppm。
- 根据权利要求1或2所述的一种可生物降解聚酯组合物,其特征在于,按重量份计,包括组分:i)65至95份的可生物降解的脂族-芳族聚酯;ii)5至35份的聚乳酸;iii)5至25份的有机填料和/或无机填料;iv)0.02至0.5份的含有环氧基团且基于苯乙烯、丙烯酸酯和/或甲基丙烯酸酯的共聚物。
- 根据权利要求2或3所述的一种可生物降解聚酯组合物,其特征在于,所述环戊酮的重量含量采用如下方法测试:精确称量1.2000g的可生物降解聚酯组合物加入静态顶空测试瓶中,通过静态顶空方法测试可生物降解聚酯组合物中环戊酮的峰面积,根据可生物降解聚酯组合物中环戊酮的峰面积和环戊酮标准曲线即可计算得到可生物降解聚酯组合物中环戊酮的含量;标准曲线由环戊酮/甲醇溶液标定。
- 根据权利要求1-3任一项所述的一种可生物降解聚酯组合物,其特征在于,所述可生物降解的脂族-芳族聚酯为聚己二酸对苯二甲酸丁二醇酯PBAT、聚琥珀酸对苯二甲酸丁二醇酯PBST或聚癸二酸对苯二甲酸丁二醇酯PBSeT中的一种或几种。
- 根据权利要求1-3任一项所述的一种可生物降解聚酯组合物,其特征在于,所述有机填料选自天然淀粉、塑化淀粉、改性淀粉、天然纤维或木粉中的一种或其混合物;所述无机填料选自滑石粉、蒙脱土、高岭土、白垩、碳酸钙、石墨、石膏、导电炭黑、氯化钙、氧化铁、白云石、二氧化硅、硅灰石、二氧化钛、硅酸盐、云母、玻璃纤维或矿物纤维中的一种或其混合物。
- 根据权利要求1-3任一项所述的一种可生物降解聚酯组合物,其特征在于,还包括0至4份的至少一种下述物质:增塑剂、脱模剂、表面活性剂、蜡、防静电剂、染料、UV吸收剂、UV稳定剂或其他塑料添加剂。
- 根据权利要求1-7任一项所述的一种可生物降解聚酯组合物,其特征在于,所述可生物降解聚酯组合物在吹膜挤出速度为176Kg/h时,膜厚极差<0.2μm,膜厚相对偏差<1%。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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JP2018511325A JP6471264B2 (ja) | 2016-03-07 | 2016-12-15 | 生分解性ポリエステル組成物 |
EP16893321.6A EP3260494B1 (en) | 2016-03-07 | 2016-12-15 | Biodegradable polyester composition |
US15/578,249 US10364320B2 (en) | 2016-03-07 | 2016-12-15 | Biodegradable polyester composition |
AU2016396710A AU2016396710B2 (en) | 2016-03-07 | 2016-12-15 | Biodegradable polyester composition |
KR1020177034905A KR101998502B1 (ko) | 2016-03-07 | 2016-12-15 | 생분해성 폴리에스테르 조성물 |
ES16893321T ES2874151T3 (es) | 2016-03-07 | 2016-12-15 | Composición de poliéster biodegradable |
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CN201610126865.1 | 2016-03-07 | ||
CN201610126865.1A CN105713356B (zh) | 2016-03-07 | 2016-03-07 | 一种可生物降解聚酯组合物 |
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WO2017152678A1 true WO2017152678A1 (zh) | 2017-09-14 |
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US (1) | US10364320B2 (zh) |
EP (1) | EP3260494B1 (zh) |
JP (1) | JP6471264B2 (zh) |
KR (1) | KR101998502B1 (zh) |
CN (1) | CN105713356B (zh) |
AU (1) | AU2016396710B2 (zh) |
ES (1) | ES2874151T3 (zh) |
WO (1) | WO2017152678A1 (zh) |
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CN105713356B (zh) | 2016-03-07 | 2017-05-31 | 杨红梅 | 一种可生物降解聚酯组合物 |
CN105585825A (zh) | 2016-03-07 | 2016-05-18 | 杨红梅 | 一种可生物降解聚酯组合物 |
EP3494169A1 (en) * | 2016-08-02 | 2019-06-12 | Vinventions USA, LLC | Closure for a product-retaining container |
CN107698944A (zh) * | 2016-08-09 | 2018-02-16 | 营口永胜降解塑料有限公司 | 一种全生物降解覆盖地膜的生产工艺 |
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CN105713356B (zh) | 2017-05-31 |
JP2018515680A (ja) | 2018-06-14 |
AU2016396710A1 (en) | 2018-01-18 |
ES2874151T3 (es) | 2021-11-04 |
US20180142060A1 (en) | 2018-05-24 |
CN105713356A (zh) | 2016-06-29 |
AU2016396710B2 (en) | 2018-10-18 |
EP3260494B1 (en) | 2021-05-12 |
JP6471264B2 (ja) | 2019-02-13 |
KR101998502B1 (ko) | 2019-07-09 |
US10364320B2 (en) | 2019-07-30 |
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KR20180002781A (ko) | 2018-01-08 |
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