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WO2022254435A1 - Feuilles biodégradables - Google Patents

Feuilles biodégradables Download PDF

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Publication number
WO2022254435A1
WO2022254435A1 PCT/IL2022/050580 IL2022050580W WO2022254435A1 WO 2022254435 A1 WO2022254435 A1 WO 2022254435A1 IL 2022050580 W IL2022050580 W IL 2022050580W WO 2022254435 A1 WO2022254435 A1 WO 2022254435A1
Authority
WO
WIPO (PCT)
Prior art keywords
pla
pcl
polymer layer
layer comprises
sheet
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
Application number
PCT/IL2022/050580
Other languages
English (en)
Inventor
Eli Lancry
Amit HAVIV
Neta ATIAS MEKAHEL
Ran LEVIM
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tipa Corp Ltd
Original Assignee
Tipa Corp Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tipa Corp Ltd filed Critical Tipa Corp Ltd
Publication of WO2022254435A1 publication Critical patent/WO2022254435A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08—Lactones or lactides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2250/00—Layers arrangement
    • B32B2250/03—3 layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2250/00—Layers arrangement
    • B32B2250/24—All layers being polymeric
    • B32B2250/244—All polymers belonging to those covered by group B32B27/36
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2270/00—Resin or rubber layer containing a blend of at least two different polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/30—Properties of the layers or laminate having particular thermal properties
    • B32B2307/31—Heat sealable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/414—Translucent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/54—Yield strength; Tensile strength
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/558—Impact strength, toughness
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/716—Degradable
    • B32B2307/7163—Biodegradable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/724—Permeability to gases, adsorption
    • B32B2307/7242—Non-permeable
    • B32B2307/7244—Oxygen barrier
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/724—Permeability to gases, adsorption
    • B32B2307/7242—Non-permeable
    • B32B2307/7246—Water vapor barrier
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2439/00—Containers; Receptacles
    • B32B2439/40—Closed containers
    • B32B2439/46—Bags
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2439/00—Containers; Receptacles
    • B32B2439/70—Food packaging
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2439/00—Containers; Receptacles
    • B32B2439/80—Medical packaging
    • 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
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
    • Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics

Definitions

  • the present invention in at least some embodiments, is directed to biodegradable sheets, and in particular to multilayered biodegradable sheets having at least three layers, wherein a first outer polymer layer comprises a polymer selected from the group consisting of PBSA, PLA, PCL and combinations thereof; a second outer polymer layer comprises PB AT ; and a first inner polymer layer comprises PLA and PCL.
  • a first outer polymer layer comprises a polymer selected from the group consisting of PBSA, PLA, PCL and combinations thereof
  • a second outer polymer layer comprises PB AT ;
  • a first inner polymer layer comprises PLA and PCL.
  • biodegradable materials had increased over the past years due to the environmentally beneficial properties of such materials. Such materials are now commonly used in the manufacture of a wide range of products, including various types of plastic bags and other forms of packaging. In response to the demand for more environmentally friendly packaging materials, a number of new biopolymers have been developed that have been shown to biodegrade when discarded into the environment.
  • polymers examples include biopolymers based on polylactic acid (PLA), polyhydroxyalkanoates (PHA), which include polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV) and polyhydroxybutyrate-hydroxyvalerate copolymer (PHBV), and poly (epsilon- caprolactone) (PCL).
  • PLA polylactic acid
  • PHA polyhydroxyalkanoates
  • PVB polyhydroxybutyrate
  • PV polyhydroxyvalerate
  • PHBV polyhydroxybutyrate-hydroxyvalerate copolymer
  • PCL poly (epsilon- caprolactone)
  • PHB and PLA tend to be strong but are also quite rigid or even brittle. This makes them poor candidates when flexible sheets are desired, such as for use in making wraps, bags and other packaging materials requiring good bend and folding capability.
  • biopolymers such as polybutylene adipate terphtalate (PBAT)
  • PBAT polybutylene adipate terphtalate
  • biodegradable polymers are not as widely used in the area of food packaging materials, particularly in the field of liquid receptacles, as desired for ecological reasons.
  • biodegradable sheets known today are mostly opaque, having low light transmittance and high haze.
  • the known biodegradable sheets either do not include barrier layers or include amounts and types of barrier layers that cause the sheets to be generally highly permeable to gases, having both a high oxygen transmission rate and a high water vapor transmission rate, and thus they cannot serve as long term food or drink receptacles.
  • the physical strength of known biodegradable sheets measured by parameters, such as stress at maximum load, strain at break, and Young’s Modulus, is lacking and, therefore, is deficient when used as packaging, particularly when it is desirable to package liquids.
  • a multi-layered biodegradable sheet having PBAT as an outer layer provides the sheet with higher heat stability (up to at least 115°C). This enables the sheet to be extruded at higher temperatures than can be used for many other biodegradable polymers (such as, for example PBSA), making the extrusion process quicker and easier, with less requirement for cleaning and maintenance of the extrusion system.
  • PBAT biodegradable polymers
  • a biodegradable sheet comprising a first outer polymer layer, a second outer polymer layer and at least a first inner polymer layer located between said first and said second outer polymer layers, wherein said first outer layer comprises a polymer selected from the group consisting of PBSA, PLA, PCL and combinations thereof; wherein said second outer polymer layer comprises PBAT ; and wherein said first inner polymer layer comprises PLA and PCL.
  • said first inner polymer layer comprises from about 10wt% to about 50wt% PCL (such as about 10wt%, about 15wt%, about 20wt%, about 25wt%, about 30wt%, about 35wt%, about 40wt%, about 45wt% or about 50wt%) and from about 50wt% to about 90wt% PLA (such as about 50wt%, about 55wt%, about 60wt%, about 65wt%, about 70wt%, about 75wt%, about 80wt%, about 85wt% or about 90wt%).
  • said first inner polymer layer comprises about 20wt% PCL and about 80wt% PLA.
  • said first inner polymer layer comprises about 30wt% PCL and about 70wt% PLA.
  • said first inner polymer layer comprises about 40wt% PCL and about 60wt% PLA.
  • said first outer polymer layer comprises 100wt% PBSA.
  • said first outer polymer layer comprises from about 10wt% to about 50wt% PCL (such as about 10wt%, about 15wt%, about 20wt%, about 25wt%, about 30wt%, about 35wt%, about 40wt%, about 45wt% or about 50wt%) and from about 50wt% to about 90wt% PLA (such as about 50wt%, about 55wt%, about 60wt%, about 65wt%, about 70wt%, about 75wt%, about 80wt%, about 85wt% or about 90wt%).
  • said first outer polymer layer comprises about 20wt% PCL and about 80wt% PLA.
  • said first outer polymer layer comprises about 30wt% PCL and about 70wt% PLA.
  • said first outer polymer layer comprises about 40wt% PCL and about 60wt% PLA.
  • said second outer polymer layer comprises 100wt% PBAT.
  • Fig. 1 is a schematic representation of a three-layered sheet in accordance with the principles of the present invention. DETAILED DESCRIPTION OF THE INVENTION
  • biodegradable as used herein is to be understood to include a polymer, polymer mixture, or polymer-containing sheet that degrades through the action of living organisms in air, water or any combinations thereof within 1 year.
  • Biodegradable polyester degradation is initially by hydrolysis, to eventually break the polymer into short oligomers, and later by microbial degradation, or microbial digestion.
  • Biodegradable material may break down under a variety of conditions, for example under aerobic or anaerobic conditions, in compost, in soil or in water (such as sea, rivers or other waterways).
  • compostable Material which may be degraded in compost is referred to as compostable.
  • compostable refers to a polymer, polymer mixture, or polymer-containing sheet which is degraded by biological processes under aerobic conditions to yield carbon dioxide, water, inorganic compounds and biomass and leaves no visible, distinguishable or toxic residues. Composting of such materials may require a commercial composting facility or the material may be home compostable.
  • home compostable refers to a polymer, polymer mixture, or polymer-containing sheet which is compostable in a home composting container, i.e. at significantly lower temperatures and in the absence of set conditions as compared to those provided in a commercial composting facility.
  • Home composting is usually carried out in significantly smaller volumes than those used for commercial composting, and do not include an industrial shredding process.
  • sheet as used herein is to be understood as having its customary meanings as used in the thermoplastic and packaging arts and includes the term “film”. Such sheets may have any suitable thickness, may be of a single polymer layer or of multiple polymer layers. Such sheets may be manufactured using any suitable method including blown film extrusion and cast film extrusion.
  • the term “core layer” of a biodegradable sheet having an odd number of layers refers to the innermost layer of the sheet, such that an equal number of layers (an outer layer and at least one inner layer) is positioned on each said of the core layer.
  • reference to a specified percentage (w/w) of a polymer layer is intended to refer to the percentage of the specified polymer in a polymer mixture from which the polymer layer is formed.
  • the layer may further comprise a minor amount (no greater than about 5% (w/w) of the total composition of the layer) additives such as slip, anti-block, anti-oxidant and the like.
  • the biodegradable sheet as disclosed herein is used to prepare a biodegradable package, such as a bag or pouch, for example for containing therein an ingestible substance such as a food, drink or medicine, which may be a solid, semi-solid or liquid substance; or for containing therein a non-ingestible substance such as an item of clothing, a toiletry or cosmetic material or the like.
  • a biodegradable package such as a bag or pouch, for example for containing therein an ingestible substance such as a food, drink or medicine, which may be a solid, semi-solid or liquid substance; or for containing therein a non-ingestible substance such as an item of clothing, a toiletry or cosmetic material or the like.
  • the biodegradable package is prepared by heat sealing of two or more parts of the same sheet or two or more separate sheets.
  • poly(caprolactone) and polycaprolactone are synonymous and the terms are used interchangeably.
  • polylactic acid and poly(lactic acid) are synonymous.
  • Fig. 1 there is shown a schematic representation of three-layered sheet 10, comprising a first outer layer 12, a second outer layer 14 and an inner (core layer) 16, wherein core layer 16 is positioned between first outer layer 12 and second outer layer 14.
  • polymer sheets according to the teachings herein are made using commercially- available raw materials and devices, using one or more standard methods including: polymer resin drying, resin mixing, cast film extrusion, cast film co-extrusion, blown film extrusion and coextrusion and adhesive lamination.
  • PBAT poly(butylene adipate terephthalate) The resins may be used as supplied, without further drying. Optionally, before use, resins are further dried, such as by drying overnight in an air flow Shini SCD- 160U- 120H desiccant dryer heated to about 80 °C.
  • the polymer sheets according to the teachings herein include layers comprising a polymer mixture. Such layers are made by coextrusion of a polymer mixture resin.
  • the appropriate amounts of the dried constituent resins are dry-blended and then introduced into the feed zone of the extruders and co-extruded as a film.
  • sheets according to the teachings herein are made by coextrusion of three or more layers to make a desired sheet by multilayer cast film co extrusion.
  • sheets according to the teachings herein are made by lamination of single and multilayer cast film extruded films.
  • Films and sheets are made using a cast film coextruder Dr. Collin (Collin Lab and Pilot Solutions) using standard settings, typically the mixture is fed into the extruder with the temperature zone settings 195 °C; Adaptor at about 200°C; feedblock at about 200°C; Die at 210°C.
  • the screw speed is set to provide an extruded layer having the desired thickness in the usual way.
  • a die having three ports, each fed by a dedicated extruder is used.
  • WVTR Water vapor transmission rate
  • OTR Oxygen transmission rate
  • Exemplary sheets #1-3 representing specific embodiments according to the teachings disclosed herein are prepared, according to Table 1. The total thickness of each sheet is 40 pm.
  • each layer is extruded from a dedicated extruder, such that, for example, three extruders are used for preparing a three-layered sheet.
  • Sheet #1 made by cast film coextrusion of 100 % PBS A 20% PCL: 80% PLA 100% PBAT
  • Sheet #2 made by cast film coextrusion of 100% PBS A
  • Sheet #4 made by cast film coextrusion of 20% PCL: 80% PLA 20% PCL: 80% PLA 100% PBAT
  • Sheet #6 made by cast film coextrusion of 20% PCL: 80% PLA 40% PCL: 60% PLA 100% PBAT
  • Sheet # 8 made by cast film coextrusion of 30% PCL: 70% PLA 30% PCL: 70% PLA 100% PBAT
  • Sheet #9 made by cast film coextrusion of 30% PCL: 70% PLA 40% PCL: 60% PLA 100% PBAT Sheet #10 made by cast film coextrusion of 40% PCL: 60% PLA 20% PCL: 80% PLA 100% PBAT
  • Sheet #11 made by cast film coextrusion of 40% PCL: 60% PLA 30% PCL: 70% PLA 100% PBAT
  • Sheet #12 made by cast film coextrusion of 40% PCL: 60% PLA 40% PCL: 60% PLA 100% PBAT

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une feuille biodégradable comprenant une première couche de polymère externe, une seconde couche de polymère externe, et au moins une première couche de polymère interne située entre la première et la seconde couche de polymère externe. La première couche de polymère externe comprend un polymère choisi dans le groupe constitué par : le PBSA, le PLA, la PCL et des combinaisons de ceux-ci. La seconde couche de polymère externe comprend du PBAT. La première couche de polymère interne comprend du PLA et de la PCL.
PCT/IL2022/050580 2021-06-04 2022-06-01 Feuilles biodégradables Ceased WO2022254435A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163196889P 2021-06-04 2021-06-04
US63/196,889 2021-06-04

Publications (1)

Publication Number Publication Date
WO2022254435A1 true WO2022254435A1 (fr) 2022-12-08

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025003276A1 (fr) * 2023-06-26 2025-01-02 Ingevity Uk Ltd. Polymères et compositions bioplastiques, articles et leurs procédés de fabrication

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015059709A1 (fr) * 2013-10-27 2015-04-30 Tipa Corp. Ltd Feuille biodégradable
WO2016067285A1 (fr) * 2014-10-27 2016-05-06 Tipa Corp. Ltd Feuilles biodégradables
WO2016174665A1 (fr) * 2015-04-29 2016-11-03 Tipa Corp. Ltd Feuilles biodégradables
WO2016207888A1 (fr) * 2015-06-23 2016-12-29 Tipa Corp. Ltd. Feuilles biodégradables

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015059709A1 (fr) * 2013-10-27 2015-04-30 Tipa Corp. Ltd Feuille biodégradable
WO2016067285A1 (fr) * 2014-10-27 2016-05-06 Tipa Corp. Ltd Feuilles biodégradables
WO2016174665A1 (fr) * 2015-04-29 2016-11-03 Tipa Corp. Ltd Feuilles biodégradables
WO2016207888A1 (fr) * 2015-06-23 2016-12-29 Tipa Corp. Ltd. Feuilles biodégradables

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025003276A1 (fr) * 2023-06-26 2025-01-02 Ingevity Uk Ltd. Polymères et compositions bioplastiques, articles et leurs procédés de fabrication

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