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WO2025215212A1 - Procédé d'extraction de fractions polymères à partir d'une portion polymère synthétique - Google Patents

Procédé d'extraction de fractions polymères à partir d'une portion polymère synthétique

Info

Publication number
WO2025215212A1
WO2025215212A1 PCT/EP2025/060015 EP2025060015W WO2025215212A1 WO 2025215212 A1 WO2025215212 A1 WO 2025215212A1 EP 2025060015 W EP2025060015 W EP 2025060015W WO 2025215212 A1 WO2025215212 A1 WO 2025215212A1
Authority
WO
WIPO (PCT)
Prior art keywords
synthetic polymer
extraction liquid
liquid
polymer portion
group
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.)
Pending
Application number
PCT/EP2025/060015
Other languages
English (en)
Inventor
Andreas SOMMERFELDT
Simon FRØLICH
Mie Rehmeier
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.)
Danish Technological Institute
Vestas Wind Systems AS
Original Assignee
Danish Technological Institute
Vestas Wind Systems AS
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 Danish Technological Institute, Vestas Wind Systems AS filed Critical Danish Technological Institute
Publication of WO2025215212A1 publication Critical patent/WO2025215212A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
    • C08J11/26—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing carboxylic acid groups, their anhydrides or esters
    • 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
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • 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
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the invention relates to a method for extracting polymer fractions from a synthetic polymer body comprises cleavable linkages in order to facilitate recycling of the synthetic polymer material of the synthetic polymer portion.
  • thermoplastic polymers In the last few decades, the increased accumulation of polymer waste, specifically discarded/end-of-life plastics, in natural habitats and landfills across the world has severely affected both human health and the environment. In recent year there have been an increasing focus of recycling of polymers. For some thermoplastic polymers, mechanical recycling, have proved to be effective, but for many polymer types including thermoset polymers recycling is still a challenge.
  • WO 2018213317 describes a curing agent for crosslinking epoxy resin, where the curing agent comprises a cleavable linkage.
  • the examples shows that an epoxy material cured with the curing agent may be degraded be being mixed with an acetic acid and a solvent at elevated temperature.
  • US2017342301 describes a degradable and recyclable epoxy conductive adhesive, which comprises a curing agent comprising a breakable molecular structure.
  • the conductive adhesive can be degraded in normal pressure using acid and solvent. It is described that the degraded polymer may be recovered after neutralizing with an alkali solution, however there are no examples on the degradation or recovery.
  • the cured epoxy is degraded by acid and solvent, where the acid used is hydrochloric acid methanesulfonic acid or methyl sulfonic acid and the solvent used is ethylene glycol, octanol, hexanol or phenylcarbinol.
  • Aditya Birla Chemicals (Thailand) Pvt. Ltd has marketed a hardener technology for crosslinking of polymers, where the hardeners comprise cleavable linkages. These hardeners are sold under the tradename Recyclamine®. According to Aditya Birla Chemicals a polymer matrix made from a resin crosslinked by Recyclamine® may be degraded and dissolved by acetic acid and the dissolved fractions may be recovered by neutralization with a basic solution to recover the resin.
  • An objective of the present invention is to provide a relatively fast and cost effective method of decomposing a synthetic polymer portion comprising cleavable linkages, such as the polymers with cleavable linkages as described above.
  • the inventors of the present invention have found that a surprisingly effective method of cleaving the cleavable linkages of the synthetic polymer portion and thereby decomposing synthetic polymer portion to obtain polymer fractions dissolved in an extraction liquid.
  • the inventors have found a method to recover the polymer fractions from the extraction liquid
  • structural body means herein any structure comprising a synthetic polymer portion.
  • the structural body consist of the synthetic polymer portion.
  • the structural body is a composite structure comprising at least one at least partially embedded element, such as at least one embedded solid element, which is different from the synthetic polymer portion, preferably which is not of a synthetic polymer material with cleavable linkages.
  • the structural body may for example comprise several embedded solid elements e.g. arranged in layers. Examples of embedded solid elements includes reinforcement elements, such as fibers and/or metallic elements, polymer elements, filler elements, glue, fasteners, electrical and electronic components, sensors, cables etc.
  • the composite structure may further comprise non- or partly embedded solid elements or parts thereof, such as coatings e.g. paint and/or UV/weather protective coating.
  • embedded should herein be taken to mean that the embedded element partially or fully embedded in the synthetic polymer portion with cleavable linkages, preferably such that at least 50 volume % of the element is below a surface of the synthetic polymer portion.
  • the embedded element is fully embedded in the synthetic polymer portion, i.e. the embedded element is fully surrounded by the material of the synthetic polymer portion.
  • partially embedded element is herein used to designate a solid element, such as an element comprising metal, ceramic and/or a polymer different from the embedding material, such as different from the synthetic polymer portion and wherein only a portion of the partially embedded element is enclosed by the polymer. Preferably such that at least a portion of the partially embedded element remain exposed or protrudes from the embedding material, such as the synthetic polymer portion.
  • thermoset epoxy matrix and “thermoset epoxy” are used interchangeable to mean a matrix comprising a cured epoxy resin also called polyepoxides.
  • the curing is usually performed by mixing with a hardener.
  • hardener and "curing agent” are used interchangeable to mean a component responsible for reacting with the epoxy groups of an epoxy resin to result in a thermoset epoxy matrix.
  • soaking should herein be taken to mean that the at least a part of the structural body, preferably at least a part of the synthetic polymer portion is wetted thoroughly preferably such that the major area of the surfaces of the composite structure is wetted.
  • the phrase soaking of the composite structure means that the composite structure is completely wetted with the swelling fluid.
  • extraction liquid should herein be taken to mean a fluid comprising at least 10 % by weight of formic acid.
  • the remaining portion of the extraction liquid is water, such as water according to ISO 3696 (1987) Standard, grade 1, 2 or 3.
  • wt. % should herein be taken to mean per cent by weight.
  • polymer fractions should herein be taken to mean fractions of the synthetic polymer portion liberated by cleaving at least a portion of the cleavable linkages.
  • the polymer fractions may conveniently be dissolved in the extraction liquid.
  • epoxy resin should herein be taken to mean polyepoxides comprising reactive prepolymers and/or polymers which contain epoxide groups.
  • the epoxy resin comprises a bisphenol based epoxy resin e.g. based on bisphenol A or bisphenol F.
  • the epoxy resin comprises as bisphenol A diglycidyl ether (commonly known as BADGE or DGEBA).
  • cured epoxy matrix and “thermoset epoxy matrix” are used interchangeable and should herein be taken to comprise any cross linked reaction products of an epoxy resin.
  • maximal dimension should herein be taken to mean, the maximal geometrical dimension of the composite structure determined as the outside-to- outside distance across the composite structure, e.g. the distance from turbine blade root to turbine blade tip.
  • step means herein a procedure comprising one or more actions.
  • Each step of the method may comprise any number of sub-steps, which may also be referred to as steps.
  • an embodiment should be interpreted to include examples of the invention comprising the feature(s) of the mentioned embodiment.
  • the term “substantially” should herein be taken to mean that ordinary product variances and tolerances are comprised. All features of the invention and embodiments of the invention as described herein, including ranges and preferred ranges, may be combined in various ways within the scope of the invention, unless there are specific reasons not to combine such features.
  • any properties, ranges of properties and/or determination and/or assay condition is given, determined or performed at 1 atmosphere (1.01325 Bar) and 25 °C.
  • the method of extracting polymer fractions from a synthetic polymer portion comprises soaking at least a part of synthetic polymer portion in an extraction fluid.
  • the synthetic polymer portion should be soaked in the extraction liquid for a sufficient time to allow the extraction liquid to penetrate into the synthetic polymer portion and cleaving at least a portion of the cleavable linkages to degrade the synthetic polymer portion and liberating the polymer fractions.
  • the synthetic polymer portion is free of any acidic liquids at the time of soaking the synthetic polymer portion in the extraction liquid.
  • a higher control of the method of extraction may be obtained and simultaneously the risk of mixing the extraction liquid with undesired chemicals which may complicate reusing of the extraction fluid may be reduced or even avoided.
  • the synthetic polymer portion is dry at the time of soaking the synthetic polymer portion in the extraction liquid.
  • the synthetic polymer portion is wetted with water having a pH value of between 6 and 8 at the time of soaking the synthetic polymer portion in the extraction liquid.
  • the water may for example be remains of a washing water.
  • the sufficient time for soaking may be a low as 1 minute or even less.
  • the soaking time should advantageously be 1 hour or more, such as 5 hours or more, such as 12 hours or more, such as 24 hours or more.
  • the required soaking time for degrading the entire synthetic polymer portion depends on the size and shape of the synthetic polymer portion, the type of synthetic polymer, the temperature and the extraction liquid.
  • the extraction liquid has been found to be surprisingly effective in penetrating the synthetic polymer portion and cleaving the cleavable linkages whereby at least the main part by weight of the polymer fractions resulting from the cleaving will be dissolved.
  • the extraction liquid has a surprisingly high cleaving capacity.
  • the extraction liquid may reach to a point of saturation, meaning that a part, such as a minor part of the polymer fractions may precipitate.
  • the polymer fractions may be obtained as polymer fractions dissolved in the extraction liquid.
  • the soaking of the at least a part of synthetic polymer portion in the extraction fluid and allowing the extraction liquid to penetrate into the synthetic polymer portion and cleaving at least a portion of said cleavable linkages to degrade the synthetic polymer portion and liberating said polymer fractions is performed as a single step procedure.
  • the extraction of the polymer fractions from the synthetic polymer portion comprises obtaining the polymer fractions in the form of the extraction liquid comprising the polymer fractions dissolved therein.
  • the extraction of the polymer fractions from the synthetic polymer portion comprises obtaining the polymer fractions in the form of the extraction liquid comprising the polymer fractions precipitated therein.
  • the extraction of the polymer fractions from the synthetic polymer portion comprises obtaining the polymer fraction in isolated form.
  • the extraction liquid comprises at least 10 wt. % of formic acid. It has been found that the use of formic acid as extraction liquid is surprisingly effective as it will be demonstrated below and in particular it has been found that an extraction liquid comprising formic acid is both a very fast cleaving agent and has a very high capacity.
  • the extraction liquid comprises at least 25 wt. %, such as at least 50 wt. %, such as at least 60 wt. %, such as at least 70 wt. %, such as at least 80 % of formic acid.
  • formic acid Since formic acid is Hygroscopic it may absorb moisture or water from the air and should advantageously be kept refrigerated until use. For this reason the reference to 100% formic acid is herein used to mean at least 99 % formic acid, since minor amounts of moisture may have been absorbed from the air.
  • the extraction liquid may comprise additives, such as alcohols, dissolved salts, additional solvents and or surfactants it has been found that there is in practice no need for such additional solvents and it is therefore preferred to keep an optional amount of additional solvent below 10 wt. %, preferably below 1 wt. %.
  • the amounts of chemicals other than water and formic acids in the extracting fluid is kept relatively low.
  • the risk of damaging fully or partially embedded solids may be reduced or even avoided and simultaneously reusing the extraction fluid may be simpler while simultaneously ensuring a high control of the extraction procedure of the method of extraction.
  • the extraction liquid comprises at a maximum 10 % by volume of ethanol, such as a volume not exceeding 5 % of ethanol, such as a volume not exceeding 1 % of ethanol, preferably the extraction liquid is essentially free of ethanol.
  • the extraction liquid comprises at a maximum 5 % by volume of hydrochloric acid, such as a volume not exceeding 2 % of hydrochloric acid, such as a volume not exceeding 1 % of hydrochloric acid, preferably the extraction liquid is essentially free of hydrochloric acid.
  • the extraction liquid comprises at a maximum 10 % by volume of ethanol, such as a volume not exceeding 5 % of ethanol, such as a volume not exceeding 1 % of ethanol, preferably the extraction liquid is essentially free of ethanol.
  • the extraction liquid comprises at a maximum 5 % by mol of peroxide, such as hydrogen peroxide, preferably the extraction liquid is essentially free of peroxide(s).
  • a minor amount of such additional solvents may be suitable where the synthetic polymer portion is covered in dirt, wax or similar.
  • the remaining part of the extraction liquid may be water, such as distilled water e.g. water according to ISO 3696 (1987) Standard, grade 1, 2 or 3.
  • the synthetic polymer portion comprises cleavable linkage. As described in the background art section above some synthetic polymers having cleavable linkages are known in the art.
  • the soaking may be performed by submerging the structural body or at least the synthetic polymer portion partly or preferably fully in a portion of the extraction liquid.
  • the soaking may be performed by sprinkling the structural body or at least the synthetic polymer portion thereof to thoroughly wet the major area of the surfaces of the structural body and/or the synthetic polymer portion.
  • the sprinkling may be continuous or discontinuous with periods of sprinkling and periods of non-sprinkling, advantageously such that periods of non-sprinkling is sufficiently short for the wetted surfaces of the composite structure to dry.
  • periods of non-sprinkling are less than 10 minutes, such as less than 5 minutes, such as less than 1 minute.
  • Advantageously periods of sprinkling are longer than periods of nonsprinkling.
  • the cleavable linkages may comprise identical functional groups or may comprise different functional groups.
  • the cleavable linkages comprise a functional group comprising a carbon atom bonded to two or three oxygen atoms.
  • Each of the cleavable linkages may advantageously and independently from each other comprise an acetal functional group.
  • the acetal functional group may conveniently comprise a carbon atom bonded to two
  • each R group preferably represents a spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion and the the R' group may represent a hydrogen atom, a C1-C8 alkyl group, or a C6-C10 aryl group.
  • acetal is herein used to include ketals according to IUPAC. "htps://doi.orq/10.1351/qoldbook.A00062"
  • the R' group may represent a C1-C8 alkyl group, or a C6-C10 aryl group.
  • the acetal functional group has the formula R'2C(OR)2, wherein each R' independently of each other represents an -OH group, a hydrogen atom, a C1-C8 alkyl group, or a C6-C10 aryl group and wherein each R group represents a spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion.
  • the cleavable linkages comprise an orthoester functional group having the formula R'C(OR)3.
  • R' represents an -OH group, a hydrogen atom, a C1-C8 alkyl group, or a C6-C10 aryl group and each R group represents a spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion.
  • the synthetic polymer portion may advantageously comprises cleavable linkage which cleavable linkages independently from each other comprises an acetal, a hemiacetal, a ketal, a hemiketal, an orthoester an orthocarbonate, a organocarbonate, an organosilicon, a silanol, a siloxide, an aminal or a hemiaminal, preferably each of the cleavable linkages comprises independently from each other an acetal, a hemiacetal, a ketal, a hemiketal, an orthoester an orthocarbonate or any combinations thereof.
  • the cleavable linkages comprise independently from each other an aminal functional group which may have the formula R' 2 C(NR) 2 or a hemiaminal functional group, which may have the formula R'2C(NR)(OH).
  • Each R' group may independently of each other represents an -OH group, a hydrogen atom, a C1-C8 alkyl group, or a C6-C10 aryl group.
  • Each R group represents a spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion.
  • Each spacer R, linking the cleavable linkages to a polymer chain may independently of each other represent a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • the cleavable linkages comprise independently from each other an organosilicon comprising a silicon atom bonded to two -OR groups and optionally one OR' group, wherein each R group preferably represents a spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion and thethe R' group may represent an -OH group, a hydrogen atom, a C1-C8 alkyl group, or a C6- C10 aryl group.
  • the cleavable linkages comprises moieties selected from acetals, hemiacetals, ketals, hemiketals, orthoesters, orthocarbonates, organosilicons, silanols, siloxides aminals, hemiaminals, orga nocarbonates or any combinations thereof.
  • the cleavable linkages comprise or consists of acetal linkages, such as ketal linkages.
  • the cleavable linkages may be located at any location of the synthetic polymer portion, to ensure a desired degradation of the synthetic polymer portion and to obtain the polymer fractions to be suitable for reuse.
  • the synthetic polymer portion may advantageously be produced to provide that the cleavable linkages are located in backbone polymer chains or crosslink chains and/or both in backbone polymer chains and in crosslink chains of the polymer, such that when cleaved the obtained polymer fractions may readily be reused for producing a fresh polymer.
  • the synthetic polymer portion may for example comprises a backbone structure and/or a crosslinking structure comprising the cleavable linkages.
  • the synthetic polymer portion comprises a thermoplastic polymer and/or a thermoset polymer, wherein the synthetic polymer portion comprises a backbone structure comprising the cleavable linkages.
  • the synthetic polymer portion may for example be a TPE block copolymer and the cleavable linkages may be located between blocks of the copolymer.
  • the synthetic polymer portion is a TPE blend comprising rubber domains dispersed in a thermoplastic polymer, wherein the cleavable linkages are located in the thermoplastic polymer. Thereby, by cleaving the cleavable linkages the rubber domains may be liberated from the thermoplastic polymer fractions.
  • the synthetic polymer portion is a crosslinked polymer and at least a portion of the cleavable linkages are located in the crosslink, moieties, such as in cross link chains of the crosslinked polymer, preferably all of the cleavable linkages are located in the crosslink moieties.
  • the synthetic polymer portion is of a thermoset polymer, wherein the synthetic polymer portion comprises a crosslinking structure comprising the cleavable linkages.
  • the synthetic polymer portion may advantageously comprise a cured epoxy.
  • epoxy materials offer a combination of desirable properties that make them indispensable in a wide range of industries, including aerospace, automotive, construction, wind turbine blades, electronics, marine, and healthcare. Therefore the amount of used cured epoxy, such as from decommissioned turbines increases and often the used cured epoxy is in the form of relatively large synthetic polymer portions.
  • there are solutions comprising incorporating cleavable linkages into for crosslinked polymer, by using a hardener comprising such cleavable linkages with a hardener.
  • the present invention provides a very fast and effective method of extracting polymer fractions from a synthetic polymer portion of a structural body which is therefore very beneficial for degrading relatively large synthetic polymer portions, such as relatively large synthetic cured epoxy portions.
  • the obtained polymer fractions may be in the form of the uncured resin chains such as epoxy resin comprising reactive prepolymers and/or polymers which contain epoxide groups, such as epoxy resin comprising a bisphenol based epoxy resin e.g. based on bisphenol A or bisphenol F.
  • the extraction liquid comprises more than 75 wt. % of formic acid, such as at least 80 wt. %, such as at least 90 wt. %, such as at least 98 wt. %, such as at least 99 wt. % of formic acid.
  • the method may be performed at relative low temperature, which may be very beneficial since heating may not be required. Thereby the method may be performed in a relatively simple way involving relative low protection requirements of the operators performing the extraction method.
  • the soaking is performed at a temperature below 100 °C, such as below 80 °C, such as below 70 °C, such as below 50 °C, such as below 40 °C from larger than 10 °C to less than 30 °C, Preferably the soaking is performed at a temperature below 70 °C, more preferably the soaking is performed at a temperature below 50 °C.
  • the method of the invention is very fast compared to prior art methods, which thereby make the method very suitable for use where the synthetic polymer portion is relatively large.
  • the structural body is a consumable used in production of a wind turbine blade, an airplane, a ship, an automobile, a bridge decking, a boat and/or a circuit board, which consumable is contaminated with the synthetic polymer portion.
  • the consumable may for example be a vacuum bag, a tube, a hose or another distribution media, a valve, a tool (such as a spatula, a bucket or other container, a brush, a roll, a mould), a personal protection equipment and the like.
  • the structural body has a volume of at least 1 m 3 , such as a volume of at least 5 m 3 , such as a volume of at least 10 m 3 , a volume of at least 15 m 3 .
  • the synthetic polymer portion has a volume of at least 1 m 3 , such as a volume of at least 5 m 3 , such as a volume of at least 10 m 3 , a volume of at least 15 m 3 .
  • the limit for the size of the structural body with the synthetic polymer portion is the size of the container in which the soaking may be performed.
  • the time for fully degradation the synthetic polymer portion may also have an influence for the selection of the size of the synthetic polymer portion.
  • the size of the structural body and/or the synthetic polymer portion may be selected to not exceeding 20 m 3 .
  • the structural body is relatively large, it may not be required to cut a used polymer containing structure in smaller pieces or for example where the polymer containing structure is very large such as a turbine blade, the number of cuts may be reduced.
  • the structural body is a composite structural body comprising one or more fully or partially embedded elements other than the synthetic polymer portion, such as fibers, metal roots and/or cables
  • the structural body is relatively large since such fully or partially embedded elements, such as relatively large fiber elements, metal roots and cables may be liberated unharmed from the synthetic polymer portion. This facilitates reclaiming and recycling of the liberated elements.
  • the larger size may facilitate recycling by reuse of embedded elements rather than other less favourable routes for recycling, such as for example involving remelting of fibres or metal parts.
  • the structural body may conveniently have a relatively large weight, such as a weight of at least 500 kg, such as a weight of at least 1000 kg, such as a weight of at least 1500 kg.
  • the synthetic polymer portion has a weight of more than 500 kg, preferably in the range from 1000 kg to 2000 kg.
  • the synthetic polymer portion constitutes the entire structural body.
  • the structural body synthetic polymer portion form part of a structural body may be a composite structure, which in in addition to the synthetic polymer portion comprises one or more partially or fully embedded elements.
  • the synthetic polymer portion may conveniently constitute at least % by weight of the structural body, such as at least 20 % by weight of the structural body.
  • the synthetic polymer portion may be at most 50 % by weight of the structural body, such as at most 40 % by weight of the structural body.
  • the one or more partially or fully embedded elements may be any kind of element, preferably solid elements, such as fibres, foams, metals, sensors and other e.g. as explained below.
  • the at least one partially or fully embedded element comprises one or more reinforcement elements and/or one or more support elements.
  • the one or more embedded elements may comprise one or more metallic embedded elements e.g. comprising steel, aluminum, titanium, chromium, cobalt, nickel, copper, zinc, tin, lead and any alloys comprising at least one of the before mentioned.
  • the embedded element(s) comprises one or more wires and/or grids of metal.
  • the embedded element(s) comprises metal fibers and/or a metal girder.
  • the reinforcement element(s) comprises at least one reinforcement layer, such as two or more reinforcement layers optionally glued or stitched together.
  • the reinforcement layer(s) may for example comprise one or more of fibers, metal, polymer, wood, ceramic and/or silicates.
  • the one or more support element may comprise any elements that are not having reinforcing function, such as filler, shaping aid, electrical component, lightning protections, sensors, paint, glue and/or core elements such as foams and/or woods.
  • the structural body may in an embodiment comprise fibers selected from one or more of synthetic fiber, semi -synthetic fiber, regenerated fiber, plant fiber, carbon fiber, basalt fiber, glass fiber and/or metal fiber, the fiber may preferably be in the form of at least one sheet comprising fibers e.g. at least one sheet comprising fibers embedded in a polymer different from the synthetic polymer portion.
  • the structural body may in an embodiment comprise one or more partially or fully embedded elements in the form of wood, such as balsa and/or polymers without the cleavable linkages, such as foamed plastic such as foamed plastic comprising at least one of polystyrene (PS), polyurethane (PU), poly(vi nyl chloride) (PVC), polyethylene terephthalate (PET), polyolefins (polyethylene (PE) and polypropylene (PP)) and ABS foams, preferably the foamed plastic is rigid.
  • foamed plastic such as foamed plastic comprising at least one of polystyrene (PS), polyurethane (PU), poly(vi nyl chloride) (PVC), polyethylene terephthalate (PET), polyolefins (polyethylene (PE) and polypropylene (PP)) and ABS foams, preferably the foamed plastic is rigid.
  • foamed plastic such as foamed plastic comprising at least one of polys
  • the structural body may in an embodiment comprise one or more partially or fully embedded elements comprising a thermoset matrix without the cleavable linkages, such as cross-linked polyester, polyurethane, vulcanized rubber, cross-linked polyvinylester, cross-linked polyimides, cross-linked phenol-formaldehyde, crosslinked polybenzoxazine, cured amino resin, cured furan resin, cured maleimide resin, or cured silicone or any combinations comprising at least one of the before mentioned.
  • a thermoset matrix without the cleavable linkages
  • the extraction liquid has a beneficially high dissolution rate which for example may comprise dissolving the synthetic polymer portion and liberating the polymer fractions with a velocity of at least 1 cm 3 per 10 minutes from a surface of 100 cm 2 of the synthetic polymer portion in 1000 cm 3 extraction fluid at 25 °C.
  • the synthetic polymer portion may in an embodiment be at least partly of cured epoxy. Thereby the method provides a large contribution towards a sustainable circular economy within many industries where the use of epoxy is required.
  • the structural body may for example be or comprise a portion of a wind turbine blade, an aircraft (e.g. an airplane), a ship, an automobile, a bridge decking, a boat and/or a circuit board.
  • the structural body is or comprises a consumable or a part of a consumable used in production of a wind turbine blade, an airplane, a ship, an automobile, a bridge decking, a boat and/or a circuit board, which consumable is contaminated with the synthetic polymer portion.
  • the method further comprises separating the extracted polymer fractions from the extraction liquid, wherein the method comprises precipitating the extracted polymer.
  • the separation of the extracted polymer fractions from the extraction liquid may advantageously be performed using a precipitating liquid and separating the precipitated polymer fractions from the extraction liquid, wherein the precipitating liquid is an aqueous liquid.
  • the separation of the extracted polymer fractions from the extraction liquid comprises cooling the extraction liquid, such as to a temperature of 15 °C or less, such to a temperature of 10 °C or less, such as to a temperature of 5 °C or less.
  • the separation of the extracted polymer fractions from the extraction liquid comprises a combination of using a precipitating liquid and cooling the extraction liquid, such as to a temperature of 15 °C or less, such to a temperature of 10 °C or less, such as to a temperature of 5 °C or less.
  • the separation of the extracted polymer fractions comprises inducing the extracted polymer fractions to precipitate e.g. as described herein followed by centrifugation and/or sedimentation of the polymer fractions.
  • the method comprising adding the precipitating liquid to the extraction liquid comprising the extracted polymer fractions.
  • the volume of the precipitating liquid relative to the volume of the extraction liquid is conveniently from 5 % to 200 %, such as from 10 % to 150 %, such as from 20 % to 100 %.
  • the precipitating liquid is a base, preferably having an acid neutralizing capacity insufficient to neutralize the acid of the extraction liquid.
  • the neutralizing capacity is determined based on the volume of the precipitating liquid added relative to the volume of the extraction liquid, wherein the volume of the precipitating liquid added relative to the volume of the extraction liquid preferably is less than 200 % of the volume of the extraction fluid, such as preferably less than 100 %, such as less than 50 % of the volume of the extraction fluid.
  • the precipitating liquid prior to adding to the extraction liquid has a pH value of 8 or less.
  • the precipitating liquid prior to adding to the extraction liquid has a pH value of 7 or less, such as from 4 to 7.
  • the precipitating liquid is aqueous liquid having a pH value between 6 and 8, such as demineralized water.
  • the precipitating liquid is water according to ISO 3696 (1987) Standard, grade 1, 2 or 3.
  • the polymer fractions may fast and effectively be precipitated by the precipitating liquid even where the precipitating liquid is water.
  • the precipitation of the extracted polymer may conveniently comprise mixing the extraction liquid comprising the dissolved polymer fractions with the precipitating optionally during agitation.
  • the precipitation of the extracted polymer from the extraction liquid comprises adding the precipitating liquid to the extraction liquid with the dissolved polymer fractions.
  • the precipitation of the extracted polymer fractions from the extraction liquid with the dissolved polymer fractions comprises adding the extraction liquid with the dissolved polymer fractions to the precipitating liquid. It has been found that the polymer fractions precipitate as solid polymer fractions. After completed precipitation, the polymer fractions may be separated from the mixture of extraction liquid and precipitating liquid.
  • the separation of the polymer fractions may be separated from the mixture of extraction liquid and precipitating liquid may be performed by for example settling, drying and/or filtering, such as filtering followed by drying.
  • Settling may involve allowing the solid polymer fractions to settle under the influence of gravity in a settling tank or vessel.
  • the mixture of extraction liquid and precipitating liquid mays then be decanted or siphoned off, leaving behind the settled solid polymer fraction.
  • Drying comprising remove mixture of extraction liquid and precipitating liquid from the mixture of polymer fractions, extraction liquid and precipitating liquid.
  • the drying may conveniently be performed by air drying, or oven drying.
  • formic acid has a boiling point very close to the boiling point of water (about 100.2 °C at one atm, pressure) it may be difficult to separate formic acid from water using distillation and other distillation methods, such as freeze distillation may be applied or is may be accepted that the a mixture of formic acid and water may be obtained in the distillation process, such as a mixture comprising e.g. up to 78% formic acid.
  • Filtration may comprise passing the mixture of polymer fractions, extraction liquid and precipitating liquid through a filter medium, such as a porous membrane or filter paper.
  • the separation of the precipitated polymer fractions from the mixture of precipitating liquid and extraction liquid is performed by filtration.
  • the polymer fractions may be reused e.g. for producing fresh polymer.
  • the polymer fractions may be separated further into monomers or oligomer useable for synthesis for new resin.
  • the method of separation of the precipitated polymer fractions from the mixture of precipitating liquid and extraction liquid comprised obtaining the separated polymer fractions and the mixture of extraction liquid and precipitating liquid.
  • the extraction liquid may be reused, e.g. by evaporating at least a part of the precipitating liquid. This is especially beneficial where the precipitating liquid is water.
  • the invention also comprises a solution of polymer fractions comprising at least 35 % w/v of dissolved polymer fractions in an extraction liquid, wherein the solution preferably comprises a concentration of at least 50 % w/v, such as 70 % w/v, such as 80 % w/v, such as 90 % w/v of dissolved polymer fractions in an extraction liquid.
  • a percent w/v solution is calculated with the following formula using the gram as the base measure of weight (w):
  • % w/v g of sol ute/ 100 mL of solution *100.
  • the dissolved polymer fractions are preferably a reaction product comprising a synthetic polymer comprising cleavable linkages where at least a portion of said cleavable linkages have been cleaved.
  • the cleavable linkages have been cleaved by reaction between the synthetic polymer and the extraction liquid.
  • the solution of polymer fractions may be obtained as an intermediate of the method of extracting polymer fractions from a synthetic polymer portion of a structural body.
  • the solution of polymer fractions extraction liquid may advantageously be as described above.
  • the invention also comprises a method of extracting solid polymer fractions from the solution of polymer fractions as described above.
  • the method of extracting solid polymer fractions from the solution of polymer fractions comprises separating the extracted polymer fractions from the extraction liquid, wherein the method comprises precipitating the extracted polymer using a precipitating liquid and separating the precipitated polymer fractions from the extraction liquid, wherein the precipitating liquid is an aqueous liquid.
  • the method may be as described above.
  • the precipitating liquid is water or a base as described above.
  • the invention also comprises a recycling system.
  • the recycling system comprises a structural body comprising a synthetic polymer portion and an extraction liquid, wherein the synthetic polymer portion comprises cleavable linkages and wherein the extraction liquid comprises at least 10 wt. %, such as at least 25 wt.%, such as at least 50 wt. %, such as at least 60 wt. %, such as at least 70 wt. %, such as at least 80 %, such as at least 90 wt.%, such as at least 98%, such as at least 99% of formic acid.
  • the synthetic polymer portion may be as described above and accordingly also the cleavable linkages may be as described above.
  • the recycling system further comprises a precipitating liquid.
  • the precipitating liquid may be as described above and preferably comprises an aqueous liquid, such as water or a base, more preferably water as described above.
  • Figure 1 illustrates a flow diagram of an embodiment of the method of the invention.
  • Figure 2 illustrates a flow diagram of another embodiment of the method of the invention.
  • Figure 3 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid.
  • Figure 4 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the synthetic polymer portion is a crosslinked epoxy resin.
  • Figure 5 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkage comprises an acetal.
  • Each R may independently of each other represents a chemical spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, and could include other heteroatoms such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group or a H.
  • Figure 6 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkage comprises a ketal.
  • Figures 7a and 7b are schematic and conceptual illustrations of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkage comprises an orthoester.
  • Figure 8 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkages comprise an orthocarbonate.
  • Figure 9 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkages comprise an organosilicon.
  • Figure 10 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkages comprise an aminal.
  • Figure 11 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkages comprise a hemiaminal.
  • Figure 12 is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkages comprise an organocarbonate.
  • Figures 13-18 are figures associated to the examples.
  • the embodiment of the method of the invention illustrated in figure 1 starts in step la, by providing a structural body comprising a synthetic polymer portion with cleavable linkages.
  • the structural body consists of the synthetic polymer portion.
  • the synthetic polymer portion may for example be a left over portion of synthetic polymer portion.
  • step lb the structural body is soaked in the extraction liquid by being submerged in the extraction liquid without heating, so the temperature may be approximately 20 °C.
  • the soaking may be performed by sprinkling, preferably in a close chamber.
  • step lc the extraction liquid is allowed to penetrate into the synthetic polymer portion and cleaving at least a portion of said cleavable linkages to degrade the synthetic polymer portion and liberating said polymer fractions.
  • This step may be referred to as the soaking time.
  • the optimal soaking time may vary mainly in dependence on the type of synthetic polymer portion, the concentration of formic acid in the extraction liquid. Also the temperature of the extraction liquid may have an influence.
  • step Id the extraction liquid with dissolved polymer fractions may be collected. Thereafter in step le the polymer fractions are precipitated by mixing the extraction liquid with dissolved polymer fractions with a precipitating liquid.
  • the precipitated polymer fractions may be separated from the mixture of the extraction liquid and the precipitating liquid, which is conveniently done by filtering and drying.
  • step 2a by providing a structural body comprising a synthetic polymer portion with cleavable linkages.
  • the structural body may for example be a cut of portion of a larger composite structure such as a portion of a turbine blade.
  • the structural body may conveniently be a portion or the entire of an aerospace construction, a marine construction or an airplane.
  • the method may be performed even where the structural body is rather large, such as with a maximal dimension of 1 meter or more, such as 5 meter or more.
  • step 2b the structural body is soaked in the extraction liquid by being submerged in the extraction liquid, where the extraction liquid has a temperature of about 50 °C.
  • the temperature may increase the degrading rate.
  • the extraction liquid is allowed to penetrate into the synthetic polymer portion and cleaving at least a portion of said cleavable linkages to degrade the synthetic polymer portion and liberating the polymer fractions.
  • the optimal soaking time may for example be 10 or more hours for relatively large synthetic polymer portions, e.g. 24 hours or more.
  • step 2d the previously embedded elements, such as described above e.g. fibers, have been liberated and may be collected optionally washed, dried and reused. It has been found that such previously embedded elements may be practically unharmed and ready for reuse.
  • step 2e the extraction liquid with dissolved polymer fractions may be collected. Thereafter in step 2f, the polymer fractions are precipitated by mixing the extraction liquid with dissolved polymer fractions with a precipitating liquid.
  • step 2g the precipitated polymer fractions may be separated from the mixture of the extraction liquid and the precipitating liquid, which is conveniently done by filtering and drying.
  • the illustration in figure 3 shows schematically a concept of an embodiment of the invention where the synthetic polymer portion is of a crosslinked polymer and where the cleavable linkages 1 are located in the crosslinking structure, i.e. in the moieties 3 forming the crosslinks.
  • the cleavable linkages 1 are here illustrated as locks with key holes.
  • the crosslinked polymer comprises a plurality of polymer chains 2 that are linked to each other via the crosslinking moieties 3 formed by a hardener upon curing the polymer.
  • the formic acid (CH 2 O 2 ) is cleaving the cleavable linkages 1 and splitting the crosslinking moieties 3 into cleaved subportions 4, which remains linked to the respective polymer chains 2 as illustrated at the right side of the arrow A.
  • the illustration in figure 4 shows an embodiment of the invention where the synthetic polymer portion is of a crosslinked epoxy and where the cleavable linkages 11 are located in the crosslinking structure, i.e. in the moieties 13 forming the crosslinks.
  • the cleavable linkages 1 are here illustrated as a C.
  • the crosslinked polymer comprises a plurality of polymer chainsl 2 that are linked to each other via the crosslinking moieties 13 formed by a hardener upon curing the polymer.
  • the epoxy resin has been cured using amine-functional curing agents, which comprises that epoxy groups of the epoxy resin reacts with the curing, resulting in that the epoxy group is opened and hydroxyl groups 15 are generated.
  • the formic acid (CH 2 O 2 ) is cleaving the cleavable linkages 11 and splitting the crosslinking moieties 13 into cleaved subportions 14, which remains linked to the respective polymer chains 2 as illustrated at the right side of the arrow A, where the cleaved polymer chains are shown.
  • Figure 5 illustrates a reaction corresponding to the reaction shown in figure 4, where the cleavable linkage comprises an acetal as marked with the square.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group but not H.
  • Each R may independently of each other represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, and could include other heteroatoms such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group or a H.
  • Figure 6 illustrates a reaction corresponding to the reaction shown in figure 4, where the cleavable linkage comprises a ketal as marked with the square.
  • Figure 7a and 7b illustrate reactions corresponding to the reaction shown in figure 4, where the cleavable linkages comprises each an orthoester as marked with the square.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, and could optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group but not H.
  • R" may for example be a C1-C8 alkyl group, or a C6-C10 aryl group but not H, and may be equal or different from R'.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, but not a H.
  • R" may for example be a C1-C8 alkyl group, or a C6-C10 aryl group or a H.
  • Figure 8 illustrates a reaction corresponding to the reaction shown in figure 4, where the cleavable linkage comprises an orthocarbonate as marked with the square.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, but not a H.
  • R' may be a third group of R representing a chemical spacer linking the cleavable linkage to a polymer chain of the synthetic polymer portion, via an amino group of the polymer chain (of R-N-polymeric chain).
  • R" may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, but not a H. In an embodiment R" may be a third or fourth group of R-N-polymeric chain.
  • Figure 9 illustrates is a schematic and conceptual illustration of cleaving the cleavable linkage by the extraction liquid, where the cleavable linkages comprises an organosilicon.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, but not a H, and may be connected via an oxygen such as O-(C1-C8 alkyl) or O-(C6-C10 aryl), or an OH.
  • R' may be a third group of O-R-N-polymeric chain.
  • R" may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, but not a H, and may be connected via an oxygen such as O-(C1-C8 alkyl) or O-(C6-C10 aryl), or an OH.
  • R" may be a third or fourth group of O-R-N-polymeric chain.
  • Figure 10 illustrates a reaction corresponding to the reaction shown in figure 4, where the cleavable linkage comprises an aminal as marked with the square.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, or a H.
  • R" may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, or a H, and may be identical or different from R'. The two R" may not be identical.
  • Figure 11 illustrates a reaction corresponding to the reaction shown in figure 4, where the cleavable linkage comprises a hemiaminal as marked with the square.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • R' may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, or a H.
  • R" may for example be a C1-C8 alkyl group, or a C6-C10 aryl group, or a H, and may be equal or different from R'.
  • the two R" may not identical.
  • Figure 12 illustrates a reaction corresponding to the reaction shown in figure 4, where the cleavable linkage comprises an organocarbonate as marked with the square.
  • Each R represents a chemical spacer linking the cleavable linkage to polymer chains of the synthetic polymer portion, here via respective amino groups of the polymer chain.
  • R may for example be a C1-C20 alkyl group, and/or a C6-C10 aryl group, optionally comprising one or more heteroatoms, such as oxygen, nitrogen, boron, sulfur, silicon, and/or halides.
  • Recydamine® epoxy The sample of Recydamine® epoxy was cut into 4 equivalent rectangular pieces (approximately 11 gram each).
  • Each piece of Recydamine® epoxy was set in a 150 mL PET bottle.
  • an extraction liquid consisting of respectively 1) 78% acetic acid in water, 2) 100% glacial acetic acid, 3) 78% formic acid in water, 4) 100% formic acid was poured over the respective pieces of Recydamine® epoxy to thereby submerge the pieces of Recydamine® epoxy.
  • a timelapse video camera was set to record the dissolution progress. During the dissolution the solid piece of Recydamine® epoxy disappears gradually, while a brown solution is emitted. Time for complete dissolution is measured by visual inspection of the timelapse video.
  • Solubility of Recyclamine samples in acid at room temperature synthetic polymer sample in the form of a cured epoxy from an epoxy resin grade Epotec® cured using a Recyclamine® hardener comprising cleavable linkages was provided.
  • the synthetic polymer sample is in the following also referred to as the Recyclamine® epoxy.
  • the sample of Recyclamine® epoxy was cut into pieces of respectively approximately 100 g and approximately 150 g.
  • Three polypropylene containers were loaded with 1) 100 gram of the Recyclamine® epoxy and 200 mL acetic acid 100%, 2) 100 gram of the Recyclamine® epoxy and 200 mL formic acid 100%, 3) 150 gram of the Recyclamine® epoxy and 150 mL formic acid 100%. These containers were sealed and left at room temperature for 31 days.
  • Sample 1 was taken from the 200 mL acetic acid 100% with 330 gram of Recyclamine® epoxy per litre.
  • Sample 2 was taken from the 150 mL formic acid 100% containing 1000 gram Recyclamine® epoxy per litre
  • Sample 3 was prepared from the 150 mL formic acid 100% by dilution with additional formic acid to provide that the sample 3 contained 330 gram of Recyclamine® epoxy per litre.
  • a 250 mL beaker was filled with 200 mL demineralized water and equipped with a magnetic stir bar.
  • the beaker was set on a magnetic stirrer at 500 rpm.
  • To this demineralized water was added drops of the sample using a 2 mL plastic pipette.
  • Figure 16 shows the beaker 31 with 200 mL demineralized water after dropwise precipitation of sample 1 and the beaker 32 with 200 mL demineralized water after dropwise precipitation of sample 2. It can be seen that the liquid in the beaker with sample 1 is completely clear and show no sign of precipitation whereas in the beaker with sample 2 the precipitated polymer fractions are clearly visible.
  • a synthetic polymer sample in the form of a cured epoxy from an epoxy resin grade Epotec® cured using a Recyciamine® hardener comprising cleavable linkages was provided as a laminate composite sample comprising embedded 4 layers standard glassfiber material.
  • the synthetic polymer sample is in the following also referred to as the Recyciamine® epoxy.
  • Two identical laminate samples were cut into shape of 2 x 10 cm squares.
  • Two 500 mL beakers were equipped with a magnetic stirbar and either a) 25%vol acetic acid in demineralized water or b) 25%vol formic acid in demineralized water. The beakers were set on a magnetic stirrer and heated to 80 °C.
  • both samples were partially submerged in respective beakers 41, 42, and set to be recorded by continuous picturing the development.
  • both laminate samples have visibly changed. The most pronounced change is observed with 25% formic acid, where a layer of glass fiber had completely delaminated itself from the remaining of the sample. This effect is not yet observed with acetic acid, since the less effective extraction liquid has yet to dissolve enough Recyciamine® epoxy.
  • Figure 17 shows the two beakers 41, 42 and a clock.
  • the left beaker 41 consists of a heated aqueous extraction liquid of 25% acetic acid at 80 °C
  • the right beaker 42 consists of a heated aqueous extraction liquid consisting of 25% formic acid at 80 °C.
  • Figure 18 shows the two beakers 41, 42 and the clock.
  • the left beaker 41 consists of the heated aqueous extraction liquid of 25% acetic acid at 80 °C
  • the right beaker consists of the heated aqueous extraction liquid consisting of 25% formic acid at 80 °C.
  • a square piece of glass fiber laminate sample cured with Recyclamine® epoxy is partially submerged.

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Abstract

L'invention concerne un procédé d'extraction de fractions polymères à partir d'une portion polymère synthétique d'un corps structural. La portion polymère synthétique comprend des liaisons clivables. Le procédé consiste à tremper au moins une partie de la portion polymère synthétique dans un fluide d'extraction et à permettre au liquide d'extraction de pénétrer dans la portion polymère synthétique et à cliver au moins une portion des liaisons clivables pour dégrader la portion polymère synthétique et libérer des fractions polymères et obtenir les fractions polymères extraites dissoutes dans le liquide d'extraction. Le liquide d'extraction comprend au moins 10 % en poids d'acide formique. De plus, l'invention concerne une solution comprenant des fractions polymères dissoutes dans un liquide d'extraction, un procédé d'extraction de fractions polymères à partir de la solution et un système de recyclage.
PCT/EP2025/060015 2024-04-11 2025-04-11 Procédé d'extraction de fractions polymères à partir d'une portion polymère synthétique Pending WO2025215212A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160046760A1 (en) 2013-04-18 2016-02-18 Adesso Advanced Materials Wuxi Co., Ltd. Novel cyclic acetal, cyclic ketal diamines epoxy curing agents and degradable polymers and composites based thereon
US20170342301A1 (en) 2014-12-19 2017-11-30 Shengyi Technology Co., Ltd. Degradable and Recyclable Epoxy Conductive Adhesive as well as Preparing, Degrading and Recycling Methods therefor
WO2018213317A1 (fr) 2017-05-15 2018-11-22 Adesso Advanced Materials Inc. Agents de durcissement dégradables à base d'amine cyclique à température de transistion vitreuse élevée et leurs applications

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US20160046760A1 (en) 2013-04-18 2016-02-18 Adesso Advanced Materials Wuxi Co., Ltd. Novel cyclic acetal, cyclic ketal diamines epoxy curing agents and degradable polymers and composites based thereon
US20170342301A1 (en) 2014-12-19 2017-11-30 Shengyi Technology Co., Ltd. Degradable and Recyclable Epoxy Conductive Adhesive as well as Preparing, Degrading and Recycling Methods therefor
WO2018213317A1 (fr) 2017-05-15 2018-11-22 Adesso Advanced Materials Inc. Agents de durcissement dégradables à base d'amine cyclique à température de transistion vitreuse élevée et leurs applications

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Title
DATTILOSANDRO ET AL.: "Full Recycling and Re-Use of Bio-Based Epoxy Thermosets: Chemical and Thermomechanical Characterization of the Recycled Matrices", POLYMERS, vol. 14, no. 22, 2022, pages 4828
FERRARIFRANCESCA ET AL.: "Fully recyclable bio-based epoxy formulations using epoxidized precursors from waste flour: thermal and mechanical characterization", POLYMERS, vol. 13, no. 16, 2021, pages 2768
SAITTA, LORENA: "Chemical Recycling of Fully Recyclable Bio-Epoxy Matrices and Reuse Strategies: A Cradle-to-Cradle Approach.", POLYMERS, vol. 15, no. 13, 2023, pages 2809

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