Repeatedly recyclable polyolefin copolymer mimics (RR-PCMS)

Abstract

A composition and methods of making the composition are described. The composition can include a repeatedly recyclable-polyolefin copolymer (RR-PCM) that is a reaction product of a difunctional linear oligomer, a functionalized branched hydrocarbon moiety, and a difunctional linker.

Description

REPEATEDLY RECYCLABLE POLYOLEFIN COPOLYMER MIMICS (RR-PCMS)

[0001] This application claims priority to and the benefit of the filing date of India Provisional Patent Application No. 202341063922, filed September 22, 2023, and European Patent Application No. 24151233.4, filed January 10, 2024, both of which are incorporated herein by reference in their entirety.BACKGROUND OF THE INVENTIONA. Field of the Invention

[0002] The invention generally relates to repeatedly recyclable-polyolefin copolymer mimics (RR-PCMs) of polyolefin copolymers. The RR-PCM can include a difimctional linear oligomer and a highly branched difimctional hydrocarbon moiety.B. Description of Related Art

[0003] Polyolefins and copolymers thereof have multiple industrial uses. Polyolefins such as polyethylene and polypropylene and copolymers thereof constitute a large volume of synthetic plastic produced worldwide. Polyolefin copolymers are used in a wide variety of articles, such as films, sheets, foams, fibers, toys, bottles, containers, furniture, electronic parts, and plumbing materials. One of the issues with the wide-spread use of polyolefin copolymers is what to do with the articles once they reach the end of their useability. One solution is to simply discard the articles (“single use articles”) and prepare new ones from new chemicals. A problem with this approach is the use of landfills and / or incinerators to discard and / or destroy the articles. Landfills are reaching capacity, and incinerators can create pollution. Still further, the use of new chemicals can be wasteful and / or increase the carbon footprint of the resulting article.

[0004] An alternative solution to discarding articles made with polyolefin copolymers is to mechanically recycle the articles. Mechanical recycling efforts physically alter an article into another form without recreating the material for new applications. The stress and energy input to physically alter the article (e.g., melt the article and reform it into a new article) can oftentimes degrade the polyolefin copolymer such as by damaging the copolymer chains (e.g., chain scission, chain branching, crosslinking, etc.). The mechanically recycled polyolefin copolymer can have reduced chemical and / or physical properties when compared with its native / virgin form. This damage oftentimes limits the amount of mechanically recycledpolyolefin copolymer that can be used to re-produce new articles. For example, virgin polyolefin copolymer is often blended with the mechanically recycled polyolefin copolymer to create new articles. The use of additional materials such as virgin polyolefin copolymer can be cost-inefficient and / or increase the carbon footprint of the resulting article.

[0005] An alternative solution to mechanically recycling articles made with polyolefin copolymers is to chemically recycle the polyolefin copolymer within the articles. Typical chemical polyolefin copolymer recycling technologies merely subject the material to energy- intensive thermal / catalytic reactions and form a mixture of materials that contain very little useful amount of recycled polyolefin copolymers. Because of this recycling inefficiency, a mixture of undesired by-products and only a small amount of polyolefins (e.g., ethylene or propylene) is obtained, undesired by-products need to be separated from the mixture, additional materials (e.g., feed stock such as virgin ethylene additive packages, catalysts, and the like) ordinarily need to be used to make a new polyolefin copolymer material. Stated another way, the recycling inefficiency of ordinary chemical recycling efforts is low, as such efforts require the use of more virgin polyolefin copolymer, additive packages, catalysts, thereby making the process costly, impractical, and energy-intensive. Examples of chemical recycling of polyethylene and polyethylene copolymers are described in International Patent Application Publication No. WO 2003 / 054061 to Maehara et al., European Patent Application Publication No. EP 3907250 to Mecking et al., U.S. Patent No. 5,643,998 to Nakano et al., International Patent Application Publication No. WO 2022 / 214639 to Chinta et. al.SUMMARY OF THE INVENTION

[0006] A discovery has been made that provides a solution to at least one or more of the problems that may be associated polyolefin copolymer recycling and methods to produce polyolefin copolymers. The discovery relates to the use of a repeatedly recyclable -polyolefin copolymer mimic (RR-PCM), which, once made into an article, can repeatedly be recreated from the article, and reused to make additional articles. The RR-PCM can be a reaction product of a first component (e.g., difimctional linear oligomers), a difimctional linker, and a second component (e.g., branched difimctional hydrocarbon moiety having 14 to 100 carbon atoms) obtained by depolymerization of an article into a liquified article that includes mixtures of the difunctional linkers, the first component (e.g., difimctional linear oligomers), and the second component (e.g., functionalized branched hydrocarbon moieties), and an article additive. The first and second components and the difimctional linker can each be obtained by, for example, melting and depolymerizing a previously manufactured and / or used article having the RR-PCMor a difunctional linear oligomer of the RR-PCM. Non-limiting examples of articles can include consumer goods, packaging products, dispensing bottles, wash bottles, tube, bags, electronic components, other molded articles, pharmaceutical containers, bottles, caps, closures, liners, trash bags, food packaging fdm and / or materials, laminations, pipes, hoses, fittings, foot apparel, etc. Advantageously, the RR-PCM of the present invention can be repeatedly and directly recreated (e.g., 2 to 500 times or more) from an article made from the RR-PCM at amounts that are substantially the same as present in the article being recycled. For example, at least 90 wt. %, 95 wt. %, 96 wt. %, 97 wt. %, 98 wt. %, 99 wt. %, or 100 wt. % of the RR- PCM from the article being recycled can be depolymerized into difunctional linear oligomers, difunctional linkers, and functionalized branched hydrocarbons, repolymerized into recreated RR-PCM, and re-used in the newly produced article. The newly produced article can include an article additive from the liquified article. This high recycling efficiency can reduce or avoid the need to use additional materials (e.g., virgin RR-PCM) to produce new articles. For example, the high recycling efficiency of the RR-PCM can reduce or avoid having to use feed stock (e.g., virgin RR-PCM feed stock) to produce additional article (s) from the recycled article(s). In some aspects, 5, 4, 3, 2, 1, 0.5, or 0 wt. % of feed stock (e.g., virgin RR-PCM feed stock) is used after 2, 3, 4, 5, 6, 7, 8, 9, 10, or more use cycles of the RR-PCM. Additionally, the recreated RR-PCM obtained from the article can have the same or substantially the same chemical and / or physical properties of the RR-PCM present in the unrecycled article. The RR- PCM(s) containing compositions, articles, and / or methods of the present invention provide for a recycling efficiency that can advantageously result in reduced costs of recycling articles, increased recycling efforts, and / or reduced amount of additional materials used to produce new articles. Still further, the recycling efficiency of the RR-PCM(s) can result in a reduced carbon footprint for the produced articles.

[0007] In one aspect, repeatedly recyclable polyolefin copolymer compositions are described. A RR-PCM composition can include a first (difiinctional linear oligomer) and a second component (functionalized branched hydrocarbon moiety) linked by a repeatedly recyclable difiinctional linker. In some aspects, the first component can be derived from a repeatedly recyclable difiinctional linear oligomer having 40 to 2000 carbon atoms (C40 to C2000), preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms, and a functionality (F) of 2.0 ± 0.3. In some aspects, the second component can be derived from a dimer of a branched functionalized hydrocarbon moiety having 14 to 100 carbon atoms, preferably 20 to 60 carbon atoms, more preferably 30 to 50 carbon atoms. The dimer can havea F of 2 ± 0.3. The repeatedly recyclable difimctional linker can have a carbon chain of two to thirteen carbon atoms (C2 to Cl 3) and a F of 2.0 ±0.3. Functionality in the difunctional linear oligomer and the difimctional linker can include an amine group (-NH-), an oxygen (-O-), a carboxyl group (-COOH), or combinations thereof. Notably, the difimctional linear oligomer and the functionalized branched hydrocarbon moiety have different carbon lengths in addition to different functionalities. Different carbon lengths provide the advantages of tunable mechanical properties, improved mechanical properties, and / or recycling processability. The repeatedly recyclable difunctional linear oligomer and the repeatedly recyclable difimctional linker can be obtained from a repeatedly recyclable-polyolefin polymer mimic that is a reaction product of a difimctional linear oligomer and a difimctional linker of a liquefied article comprising the difimctional linear oligomer and difunctional linker. The second component can be obtained from hydrogenation of a dimer of oleic acid, linoleic acid, palmitoleic acid, eleostearic acid, ricinoleic acid, vemolic acid, licanic acid, myristoleic acid, margaroleic acid, gadoleic acid, eicosadienoic acid, and / or erucic acid. In some instances, the second component is obtained from a RR-PCM that is a reaction product of a difimctional oligomer, the second component, and a difimctional linker of a liquefied article that includes the difimctional oligomer, the second component, and difimctional linker. The RR-PCM can have more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units. The RR-PCM can include repeating units according to Formulas (I) and (II).In Formulas (I) and (II), Z is an aliphatic group. X is a polyolefin backbone having 40 to 2000 carbon atoms, preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms. Y is a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, preferably 20 to 60 carbon atoms, more preferably 30 to 50 carbon atoms. A can be an amine group (-NH-), an oxygen (-O-), a carboxyl group (-COOH), or a combination thereof. The RR-PCM has more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units.

[0008] In some aspects, -Y-A- has a general structure of Formula (III):R11R12— A_S_ R14—C-CH?HR I13(III) where R11, R12, R13, R14are saturated aliphatic hydrocarbons and A is amine group (-NH-), an oxygen (-O-), a carboxyl group (-COOH) or a combination thereof. R13and R14can from a cyclic saturated ring, and the wavy line is the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (III). In some aspects, A is an oxygen atom, and -Y-A- has a general structure of Formulas (IV) or (V):In Formulas (IV) and (V), a, b, c, and d are each individually be integers from 1 to 25, and the wavy lines are the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (II).

[0009] In a preferred aspect, the RR-PCM of the present invention a portion of the RR-PCM can have a structure of Formula (VI):(VI).In Formula (VI), n is an integer ranging from 2 to 13, m is an integer ranging from 1 to 100, and a, b, c, d are each individually integers from 1 to 25. Z and Z’ are each independently an aliphatic group. X is a polyolefin backbone having 40 to 2000 carbon atoms, preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms. Y is a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, preferably 35 to 60 carbon atoms, more preferably 40 to 50 carbon atoms. The RR-PCM of Formula (VI) has more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units.

[0010] In some aspects, the composition of the present invention has a density of 0.70 g / cm3to 0.99 g / cm3. a peak melting temperature (Tm) of 70 °C to 135 °C, a crystallinity temperature (Tc) of 60 °C to 135 °C or a combination thereof. Density can be measured using standardized methods such as ASTM D792 and / or ISO 1183. Peak melting and crystallinity temperatures can be determined using differential scanning calorimetry (DSC) at heating rate of 10 °C min. In some aspects, the difunctional linear oligomer and / or the branched hydrocarbon backbone (e.g., Y) has a degree of saturation of 98% to 100%. The RR-PCM composition can include 5 to 95 mol% (e.g., 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95 mol% or any value or range there between) of the second component, 95 to 5 mol % (e.g., 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95 mol% or any value or range there between) of the first component with the balance being the linker. In some aspects, the composition can include at least 0.001 wt.% to 3 wt.%, preferably 0.015 % to 0.15 %, of an additive, preferably an article additive from a liquified article.

[0011] Methods of producing the repeatedly recyclable polyolefin copolymer mimics of the present invention are also described. A method can include reacting the difunctional linear oligomer, the difimctional linker, the functionalized branched hydrocarbon moiety, and an esterification catalyst at a temperature of 185 °C to 200 °C and a pressure of 0.1 MPa to 0.2MPa under an inert atmosphere to form an intermediate reaction mixture. The intermediate reaction mixture can be condensed at a temperature of 210 °C to 225 °C at a pressure of 0.04 MPa to 0.06 MPa to form the RR-PCM the present invention.

[0012] In some aspects of the present invention composites are described. A composite can include the RR-PCM composition of the present invention. The composite can include a plurality of fdlers. Non-limiting examples of fdlers include fibers, glass fibers, aramid fibers, polyester fibers, polyamide fibers basalt fibers, steel fibers, or combination thereof. In embodiments where the composite includes fibers, the fibers can be sized. The sizing can be a polyolefin plastomer and / or a polyolefin elastomer, or derivatives thereof.

[0013] In other aspects of the present invention, stacked polymeric compositions (e.g., laminates) are described. The stacked polymeric composition can include a composite or composition of the present invention (first layer) and a second layer. The second layer can include a composite or composition of the present invention. In some aspects, the first and second layers can be coupled together via a coupling agent (tie layer).

[0014] Certain aspects of the invention are directed to a method for making and / or recycling the composition of the present invention. A method can include liquefying (e.g., melting) an article made from a composition of the present invention. The RR-PCM in the composition can be depolymerized into a mixture containing the difunctional linear oligomers, the difimctional linkers, the second component (e.g., branched difimctional hydrocarbon moiety having 14 to 100 carbon atoms), and an article additive. In one aspect, depolymerization can be performed by hydrolysis and / or solvolysis by contacting the liquified article composition with water and / or solvent to obtain the difimctional linear oligomer, the difunctional linker and the second component. If fibers are present, the fibers can be separated and reused. In some aspects, the difunctional linear oligomer, the difimctional linker, and the second component in the mixture can be separated prior to repolymerization. Reaction of the difimctional linear oligomer, the difunctional linker, and the second component (e.g., difimctional branched hydrocarbon moiety) can produce the composition of the present invention. The composition can be formed into an article. The article can include an article additive from the liquified article. The article can be used by consumers and then recycled to produce the composition of the present invention to continue the cycle. The cycle can be repeated at least two times, preferably 2 to 500 times.

[0015] Also disclosed in the context of the present invention is a method of closed-loop recycling that encompasses a combination of mechanical and chemical recycling events. The method can include any one or any combination or all of the following steps: (1) obtaining an article comprising the RR-PCM of the present invention; (2) liquifying the article (e.g., melting the article) to obtain a liquified article composition; and / or (iii) forming a second or new article of manufacture from the liquified polymeric composition. This recycling process can be performed without having to use virgin RR-PCM or using minimal amounts of virgin RR-PCM (e.g., 10, 5, 4, 3, 2, 1, or 0 wt.% of RR-PCM). Advantageously, at least 90, 95, 96, 97, 98, 99, or 100 wt.% of the RR-PCM from the article being liquified can be reused in the newly created article. The article can include an article additive from the liquified article (e.g., greater than 0 wt.% to 5 wt.%, preferably at least 0.01 wt. % to 0.2 wt. %, or more preferably 0.05 wt. % to 0.15 wt. %, of an article additive). The composition of the present invention can be recycled multiple times and retain its mechanical and / or functional properties. In some aspects, the recycled composition may include increasing article additive loadings for each round of recycling, which could affect the mechanical and / or functional properties due to increased article additive loadings.

[0016] In yet another aspect of the present invention, the multi-cycled RR-PCM can have similar functional properties to conventional polyolefin copolymers and / or to new RR-PCMs of the present invention. This provides a solution to the problems associated with recycling conventional polyolefin copolymer (e.g., articles made with conventional polyolefin copolymers can be made with the RR-PCMs of the present invention while having a high recycling efficiency). Still further, by maintaining its functional properties after 1, 2, 3, 4, 5, or more use cycles, the RR-PCM of the present invention can continuously be reused, which can reduce and / or avoid the need to produce additional RR-PCM or to produce conventional polyolefin copolymers.

[0017] In still another aspect of the present invention, there is disclosed a composition that includes a RR-PCM, wherein the RR-PCM includes moieties derived from any one of the difunctional linear oligomers, functionalized branched hydrocarbon moieties, and from any one of the difunctional linkers disclosed throughout the specification. The RR-PCM composition can include an additive (e.g., any one of the additives disclosed throughout the specification). The additive can be an article additive from the liquified article. The composition can also include any one of the additional components, ingredients, features, and / or amounts ofingredients disclosed throughout this specification. The composition can have structural and / or functional characteristics similar to virgin RR-PCM.

[0018] Other aspects of the invention describe a RR-PCM composition, methods of recycling the composition, composites, and laminates of the present invention. Aspect 1 describes a repeatedly-recyclable copolymer mimic (RR-PCM) composition comprising repeating units according to Formula I and Formula II.where: n is an integer ranging from 2 to 13; Z and Z’ are each independently an aliphatic group; X is a polyolefin backbone comprising 40 to 2000 carbon atoms, preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms; and Y is a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, preferably 20 to 60 carbon atoms, more preferably 30 to 50 carbon atoms; and A is an oxygen atom (O), a nitrogen atom (N), or a sulfur atom (S), preferably O atom, or combination thereof, wherein Formula (I) and / or Formula (II) have more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units. Aspect 2 describes the RR-PCM composition of aspect 1, wherein -Y-A- has a general structure of (III):are saturated aliphatic hydrocarbons and A is O, N, S atoms, R13and R14can from a cyclic saturated ring, and the wavy lines are the points of connection with the carbonyl oxygen atom in Formula (I) or Formula (III). Aspect 3 describes the RR-PCM composition of aspects 1 to 2, wherein A is an oxygen atom and -Y-A- has general structures of Formulas (IV) or (V):integers from 1 to 25 and the wavy lines are the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (II). Aspect 4 describes the RR-PCM composition of any one of aspects 1 to 3, having a structure of Formula (VI):(VI), where n is an integer ranging from 2 to 13, m is an integer ranging from 1 to 100, and a, b, c, d are each integers from 1 to 25, Z and Z’ are each independently an aliphatic group; X is a polyolefin backbone comprising 40 to 2000 carbon atoms, preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms; and Y is a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, preferably 20 to 60 carbon atoms, more preferably 30 to 50 carbon atoms, wherein the RR-PCM composition has more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units. Aspect 5 describes the RR-PCM composition of any one of aspects 1 to 4, wherein the RR-PCM composition has a peak melting temperature (Tm) of 70 °C to 135 °C, a crystallinity temperature (Tc) of 60 °C to 135 °C, as determined using DSC at a heating rate of 10 °C per minute. Aspect 6 describes the RR-PCMcomposition of any one of aspects 1 to 5, wherein X has a degree of saturation of 98 % to 100%. Aspect 7 describes the RR-PCM composition of any one of aspects 1 to 6, comprising 5 to 95 mol% ofY-A, 5 to 95 mol % of X with the balance being the linker. Aspect 8 describes the RR-PCM composition of any one of aspects 1 to 7, wherein the RR-PCM composition is comprised in a composition that also comprises at least 0.001 wt.%to 3 wt.%, preferably 0.015 % to 0.15 %, of an additive, preferably an article additive. Aspect 9 describes the RR-PCM composition of any one of aspects 1 to 8, wherein the RR-PCM composition has a molecular weight ranging from 20 kg / mol to 100 kg / mol and a polydispersity index ranging from 5 to 6. Aspect 10 describes the RR-PCM composition of any one of aspects 1 to 9, wherein the RR- PCM composition of Formula (I) and / or Formula (II) are obtained from an article, wherein the article is a consumer good, a packaging product, a pharmaceutical container, a bottle, a cap, a closure, a liner, a trash bag, a food packaging fdm, a lamination, a pipe, a hose, a fitting, a foot apparel, or a combination thereof.

[0019] Aspect 11 describes a method of recycling the RR-PCM composition of any one of the aspects 1 to 10, the method comprising: (a) liquefying an article comprising the RR-PCM composition of any one of claims 1 to 10 into a mixture containing difunctional linear oligomers, difunctional linkers, and branched difunctional hydrocarbon moieties having 14 to 100 carbon atoms; and (b) reacting the difunctional linear oligomers, the difunctional linkers, and the branched difunctional hydrocarbon moieties having 14 to 100 carbon atoms to produce the RR-PCM. Aspect 12 describes the method of aspect 11, wherein the RR-PCM composition from the liquified article is depolymerized prior to step (b) by hydrolysis and / or solvolysis by contacting the composition with water and / or a solvent to obtain the difunctional oligomers, difimctional linkers, and branched difimctional hydrocarbon having 14 to 100 carbon atoms wherein the article is liquefied by melting, and wherein forming an article from the RR-PCM composition produced in step (b). Aspect 13 describes the method of any one of aspects 11 to 12, wherein the method is repeated at least two times, preferably 2 to 500 times, and wherein the article is a consumer product.

[0020] Aspect 14 describes a composite comprising the RR-PCM composition of any one of aspects 1 to 10. Aspect 15 describes the composite of aspect 14, comprising a filler having a surface in contact with the RR-PCM composition, preferably the filler is dispersed in the RR- PCM composition, wherein the filler is a continuous fiber or discontinuous fibers, preferably the fiber is a glass fiber, an aramid fibers a polyester fiber, a polyamide fiber, a basalt fiber, or a steel fiber, or combination thereof.

[0021] Aspect 16 describes a laminate comprising a first layer comprising the RR-PCM composition of any one of aspects 1 to 10 or the composite of any one of aspects 14 to 15 and a second layer. Aspect 17 describes the laminate of aspect 16, wherein the second layer comprises the RR-PCM composition of any one of aspects 1 to 10 or the composite of any one of aspects 14 to 16.

[0022] Other embodiments of the invention are discussed throughout this application. Any embodiment discussed with respect to one aspect of the invention applies to other aspects of the invention as well and vice versa. Each embodiment described herein is understood to be embodiments of the invention that are applicable to other aspects of the invention. It is contemplated that any embodiment discussed herein can be implemented with respect to any method or composition of the invention, and vice versa. Furthermore, compositions of the invention can be used to achieve methods of the invention.

[0023] The following includes definitions of various terms and phrases used throughout this specification.

[0024] “Article Additive” means an additive from an article being recycled. For example, if an article is being recycled in the context of the present invention, an additive from the recycled article is an article additive. Therefore, a composition and / or article produced from a recycled article of the present invention can include an additive or additive package from the recycled article.

[0025] “Recycled Repeatedly-Recyclable (RR) Polyolefin Copolymer Mimic” or “RR- PCM” means a copolymer that is a mimic of a polyolefin copolymer. The RR-PCM is the reaction product of a difimctional linear oligomer(s), a difunctional linker(s), a functionalized branched hydrocarbon moiety having 40 to 100 carbon atoms. The difimctional linear oligomer(s), the difimctional linker(s), and the functionalized branched hydrocarbon moieties are obtained from a liquefied article that includes the difimctional linear oligomer(s) and the difimctional linker(s), and the functionalized branched hydrocarbon moieties. The RR-PCM composition can be made into an article that is then liquefied by being heated and depolymerized into a mixture of difimctional linear oligomers, difimctional linkers, and functionalized branched hydrocarbon moieties. The difimctional linear oligomers, difimctional linkers, and functionalized branched hydrocarbon moieties (recycled or new) can then be repolymerized into another RR-PCM and re-used to produce another article. The process of the present invention can be repeated multiple times (e.g., 2, 3, 4, 5, 6, 7, 8, 9, 10, or more) so thatat least two additional or new articles can be made from the recycled RR-PCM starting material that was obtained from the recycled article.

[0026] The term “linker” means an aliphatic group (e.g., “Z”) that can couple and decouple to first component oligomer (e.g., “X”) to a second component (e.g., Y)

[0027] The terms “Virgin Repeatedly-Recyclable Polyolefin Copolymer Mimic” and “Virgin RR-PCM” refers to copolymers newly made from difimctional linear oligomers, difunctional linkers, and the functionalized branched hydrocarbon moieties (and have not been obtained from an article). Virgin RR-PCM has not previously been depolymerized and repolymerized.

[0028] ‘Use Cycle” indicates how many times an RR-PCM can be used to make different articles. For instance, for a RR-PCM having a Use Cycle 0 rating, the RR-PCM is a “virgin RR-PCM”, and, therefore, the virgin RR-PCM is made directly from a difimctional linear oligomer(s) and a difimctional linker(s) of the present invention (the virgin RR-PCM has not been used to make an article). A RR-PCM having a Use Cycle 1 rating means that the RR- PCM has been used once to make an article. A RR-PCM having a Use Cycle 2 rating means the RR-PCM has been used twice to make, for example, two different articles. A RR-PCM at Use Cycle 3 means the RR-PCM has been used three times to make, for example, three different articles. As such, a RR-PCM having a Use Cycle “n” means that the RR-PCM can been used n times to make n different articles and impart substantially similar to identical functional properties. FIG. 2 provides a non-limiting example of a visually depiction of a Use Cycle of a RR-PCM of the present invention.

[0029] The term “branching” refers the regular or random attachment of side chains to a polymer’s backbone chain.

[0030] The term “degree of branching (DB)” of a group / oligomer / polymer refers to % of branched carbons in the backbone of the group / oligomer / polymer. For example, the following group having the formula of Formula (II), has a degree of branching of 20 % to 30 %. The branched carbons in the backbone of the group of Formula II is marked with a * . R' in Formula II is a branching group, can be an alkyl group, and y is an integer and denotes number of repeat units. Degree of branching can be determined using known polymer analysis methods, for example proton and carbon nuclear magnetic resonance spectroscopy.

[0031] The term “linear hydrocarbon” refers to a hydrocarbon having a continuous carbon chain without side chain branching. The continuous carbon chain may be optionally substituted. The optional substitution can include replacement of at least one hydrogen atom with a functional group, such as hydroxyl, acid, amine, or halogen group; and / or replacement of at least one carbon atom with a heteroatom.

[0032] The term “branched hydrocarbon” refers to a hydrocarbon having a linear carbon chain containing branches, such as substituted and / or unsubstituted hydrocarbyl branches, bonded to the linear carbon chain. Optionally, the linear carbon chain can contain additional substitution. Optional additional substitutions can include replacement of at least one carbon atom in the linear carbon chain with a heteroatom and / or replacement of at least one hydrogen atom directly bonded to a carbon atom of the linear chain with a functional group, such hydroxyl, acid, amine, or halogen group.

[0033] The terms “fiber” or “filament” refers to any of a class of materials that include continuous filaments or discrete elongated materials. “Fiber” can be used interchangeably with the term “filament.” Thus, modifications made in the manufacture of fibers as disclosed herein, apply equally to other filamentous materials as well. Fibers of the present invention can be of any scale including micron and nanometer scale fibers. Fibers can include natural fibers, as well as synthetic fibers made from inorganic or organic materials. Fibers can be high temperature fibers or low temperature fibers.

[0034] The terms “about” or “approximately” are defined as being close to as understood by one of ordinary skill in the art. In one non-limiting embodiment, the terms are defined to be within 10%, preferably within 5%, more preferably within 1%, and most preferably within 0.5%.

[0035] The terms “wt.%,” “vol.%,” or “mol.%” refers to a weight percentage of a component, a volume percentage of a component, or molar percentage of a component, respectively, based on the total weight, the total volume of material, or total moles, which includes the component. In a non-limiting example, 10 grams of component in 100 grams of the material is 10 wt.% of component.

[0036] The term “substantially” and its variations are defined to include ranges within 10 %, within 5 %, within 1 %, or within 0.5 %.

[0037] The terms “inhibiting” or “reducing” or “preventing” or “avoiding” or any variation of these terms, when used in the claims and / or the specification includes any measurable decrease or complete inhibition to achieve a desired result.

[0038] The term “effective,” as that term is used in the specification and / or claims, means adequate to accomplish a desired, expected, or intended result.

[0039] The use of the words “a” or “an” when used in conjunction with any of the terms “comprising,” “including,” “containing,” or “having” in the claims, or the specification, may mean “one,” but it is also consistent with the meaning of “one or more,” “at least one,” and “one or more than one.”

[0040] The phrase “and / or” means and or “or”. To illustrate, A, B, and / or C includes: A alone, B alone, C alone, a combination of A and B, a combination of A and C, a combination of B and C, or a combination of A, B, and C.

[0041] The words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.

[0042] The compositions of the present invention can “comprise,” “consist(s) essentially of,” or “consist of’ particular groups, compositions, etc. disclosed throughout the specification. In one aspect of the present invention, and with reference to the transitional phrase “consist(s) essentially of’ or “consisting essentially of,” a basic and novel characteristic of the present invention can include a RR-PCM obtained from a liquified article that can be depolymerized into a first component (e.g., difunctional linear oligomers), a difunctional linker, and a second component (e.g., branched difiinctional hydrocarbon moiety having 14 to 100 carbon atoms) and then repolymerized into the RR-PCM and / or used to produce a new article. The newly produced article can be substantially produced from the repolymerized RR-PCM (e.g., at least 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or 100 wt. % of the newly produced article can be from the RR-PCM obtained from the liquified article). Alternatively, the difunctional linear oligomer, the difiinctional linkers, and the second component of the liquefied article can havea weight percentage that is at least 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or 100 wt.% of the RR-PCM. The RR-PCM can include an article additive from the liquified article.

[0043] Other objects, features and advantages of the present invention will become apparent from the following detailed description and examples. It should be understood, however, that the detailed description and examples, while indicating specific embodiments of the invention, are given by way of illustration only and are not meant to be limiting. Additionally, it is contemplated that changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description. In further embodiments, features from specific embodiments may be combined with features from other embodiments. For example, features from one embodiment may be combined with features from any of the other embodiments. In further embodiments, additional features may be added to the specific embodiments described herein.BRIEF DESCRIPTION OF THE DRAWINGS

[0044] Advantages of the present invention may become apparent to those skilled in the art with the benefit of the following detailed description and upon reference to the accompanying drawings.

[0045] FIG. 1 is an illustration of the system and method to make the composition of the present invention that includes a RR-PCM of the present invention.

[0046] FIG. 2 is an illustration of a closed loop Use Cycle of a RR-PCM of the present invention.

[0047] FIG. 3 is an illustration of a stacked polymeric composition of the present invention that includes four fiber-reinforced composites of the present invention.

[0048] FIG. 4 is an illustration of a stacked polymeric composition of the present invention that includes 2 fiber-reinforced composites of the present invention and a coupling layer.

[0049] FIG. 5 is an illustration of the closed-loop recycling process of the present invention that include the RR-PCM.

[0050] FIG. 6 shows a1H-NMR of virgin RR-PCM of the present invention.

[0051] FIG. 7 is a graphical representation of the differential scanning calorimetry (DSC) data of virgin RR-PCM of the present invention.

[0052] FIG. 8 is a graphical representation of the molecular weight determination of virgin RR-PCM of the present invention.

[0053] FIG. 9 is a graphical representation of the viscoelastic properties of virgin RR-PCM of the present invention.

[0054] While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof are shown by way of example in the drawings. The drawings may not be to scale.DETAILED DESCRIPTION OF THE INVENTION

[0055] A discovery has been made that provides a solution to at least one or more of the problems associated with chemical recycling of polyolefin copolymers. In one aspect, the RR- PCM of the present invention can be repeatedly and directly recreated (e.g., 2 to 500 times or more) from an article made from the RR-PCM at an amount that is substantially the same as in the article. For example, at least 90 wt. %, 95 wt. %, 96 wt. %, 97 wt. %, 98 wt. %, 99 wt. %, or 100 wt. % of the RR-PCM from the article being recycled can be depolymerized and then repolymerized into a new RR-PCM. The repolymerized RR-PCM can then be re-used in the newly produced article. This recycling efficiency of the RR-PCM containing compositions and articles made therefrom can advantageously result in reduced costs of recycling articles, increased recycling efforts, and / or reduced amount of additional materials used to produce new articles. Additionally, the recycling efficiency can result in a reduced carbon footprint for the produced articles. Notably, the RR-PCM can have similar functional properties to conventional polyolefin copolymers and / or to virgin RR-PCM. Also, the RR-PCM can be used in such a manner that additional feed stock (e.g., RR-PCM) is not used or used in limited amounts (e.g., 5, 4, 3, 2, 1, or less wt. %) after multiple use cycles (e.g., 2, 3, 4, 5, 6, 7, 8, 9, 10, or more use cycles). Notably, the difiinctional linear oligomer and the functionalized branched hydrocarbon moiety have different carbon lengths in addition to different functionality. Different carbon lengths provide the advantages of tunable mechanical properties, improved mechanical properties, and / or recycling processability. Non-limiting examples of mechanical properties include tensile strength, elasticity, thermal stability, hardness and the like.

[0056] These and other non-limiting aspects of the present invention are discussed in further detail in the following sections with reference to the Figures.A. Composition

[0057] The composition can include a RR-PCM of the present invention. In some aspects, the composition can include at least 95 wt.% to 100 wt.% (e.g., 95 wt.%, 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, 100 wt.% or any value or range there between) of the RR-PCM(s). The composition can include one or more additives and / or one or more article additives. The total amount of additives can vary by application and can be from greater than 0 wt.% to 5 wt. %, or 0.00001 wt. %, 0.0001 wt. %, 0.001 wt. %, 0.01 wt. 0.05 wt. %, 0.06 wt. %, 0.07 wt. %, 0.08 wt. %, 0.09 wt. %, 0.1 wt. %, 0.2 wt. %, 0.3 wt. %, 0.4 wt. %, 0.5 wt.%, 0.6 wt. %, 0.7 wt. %, 0.8 wt. %, 0.9 wt. 1, 1 wt. %, 2 wt. %, 3 wt. % 4 wt. %, or 5 wt. %, or any number or range there between. In some aspects the composition does not include any other polyolefin copolymers, high-density polyethylene (HDPE), low-density polyethylene (LDPE), linear low- density polyethylene (LLDPE), polyolefin elastomer (POE), plastomer polyolefin (POP), and / or polypropylene (PP), and / or combinations thereof. i. RR-PCM

[0058] The RR-PCM can include repeating units of a difunctional linker (Z), a difunctional linear oligomer (X), and a second component (e.g., a functionalized branched hydrocarbon (Y - A)). The RR-PCM can be a random block copolymer mimic, or alternatively block copolymer mimic. Block copolymers include di -blocks, tri -blocks, multi -blocks, and star-shaped block copolymers. In some aspects, the difunctional linker, difunctional linear oligomer and / or second component are obtained from a liquified article. In some aspects, the number average molecular weight (An) of the composition of the present invention can be 20,000 g / mol to 1,000,000 g / mol, 20,000 to 3,000,000 g / mol, 40,000 to 1,000,000 g / mol or 20,000 g / mol, 40,000 g / mol, 30,000 g / mol, 40,000 g / mol, 50,000 g / mol, 100,000 g / mol, 200,000 g / mol, 300,000 g / mol, 400,000 g / mol, 500,000 g / mol, 600,000 g / mol, 700,000 g / mol, 800,000 g / mol, 900,000 g / mol, 1,000,000 g / mol, or any range or value there between. The Macan be determined as the polyethylene equivalent molecular weight by high temperature size exclusion chromatography performed at 150 °C to 160 °C in trichlorobenzene using polyethylene standards. Non-limiting examples of methods to determine Mninclude ISO 16014-4 and / or ASTM D6474. The composition of the present invention can have a melt temperature (Tm) of 115 °C to 130 °C, 120 °C to 125 °C, or 115 °C, 116 °C, 117 °C, 118 °C, 119 °C, 120 °C, 122 °C, 123 °C, 124 °C, 125 °C, 126 °C, 127 °C, 128 °C, 129 °C, 130 °C, or any value or range there between as measured by DSC at a heating rate of 10 °C per min. In one aspect, the Tmof the composition of the present invention is 122.8 °C. A density of the composition of the presentinvention can be 0.70 g / cm3to 0.99 g / cm3or 0.70 g / cm3, 0.75 g / cm3, 0.80 g / cm3, 0.85 g / cm3, 0.90 g / cm3, 0.95 g / cm3, or 0.99 g / cm3or any range or value there between. In some aspects, the composition of the present invention can have a polydispersity index (PDI), of 1 to 6, or equal to any one of, at least any one of, or between any two of 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.8, 2, 2.2, 2.4, 2.6, 2.8, 3, 3.2, 3.4, 3.6, 3.8, 4.0, 4.2, 4.4, 4.6, 4.8, 4.9, 5, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, and 6. The crystallinity temperature (Tc) of the composition of the present invention can be from 90 °C to 115 °C, 95 °C to 113 °C, or 90 °C, 91 °C, 92 °C, 93 °C, 94 °C, 95 °C, 96 °C, 97 °C, 98 °C, 99 °C, 100 °C, 101 °C, 102 °C, 103 °C, 104 °C, 105 °C, 106 °C, 107 °C, 108 °C, 109 °C, 110 °C, 111 °C, 112 °C, 113 °C, 114 °C, 115 °C, or any range or value there between In one aspect, the Tcof the composition of the present invention is 111.6 °C. The glass transition peak temperature (Tg) of the composition of the present invention can be from -115 °C to -110 °C, -114 °C to -112 °C, or -115 °C, -114 °C, -113 °C, -112 °C, -111 °C, -110 °C, or any range or value there between. In one aspect, the Tgis -113 °C. Density, specific gravity, Tm, Tc, Tg, PDI and other properties can be determined using known chemical testing methods. For example, Tmand / or Tccan be measured according to ISO-11357-1 using DSC at a heating rate of 10 °C per minute. PDI can be measured according to ISO 16014-4 and / or ASTM D6474 using HT-SEC at 150 °C to 160 °C.

[0059] In some preferred aspects, the composition of the present invention can include repeating units of polymers having Formula (I) and / or Formula (II). In Formulas (I) and (II) n is an integer ranging from 2 to 13 carbons.Although ketones and oxygens are illustrated as side groups in Formulas (I), (II) and (III) the one or more side functional groups of Z can be one or more of hydroxyl (-OH), carboxylic acid (CO2H), amine (NH2), or a combination thereof, and the oxygens bonded to X or Y can be ketones, amines, etc. In some aspects, the functional groups can contain hydrocarbon groups linking the functional group to the backbone of Z. In certain aspects, Z can vary randomly between the repeating units of Formula (I), (II) and (III). Although ketones are illustrated as side groups in Formulas (I), (II), and (III), the one or more side functional groups of Z can be one or more of hydroxyl (-OH), carboxylic acid (CO2H), amine (NH2), or a combination thereof and the oxygens bonded to X or Y can be ketones, amines etc.

[0060] In Formulas (I) and (II), Z can be an aliphatic group and represents the carbon backbone of the difunctional linker. Z can contain up to 13 carbon atoms, or equal to any one of, at least any one of, or between any two of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 carbon atoms. In certain aspects, Z can contain 2 to 13 carbon atoms. In certain aspects, Z can be a Cl to Cl 3 aliphatic group. In some aspects, Z can be a linear or a branched hydrocarbon. In some aspects, Z can be a branched hydrocarbon. In certain aspects, the number of carbon atoms in the Z groups can vary randomly between the repeating units of Formulas (I) and (II) In some aspects, n is 2 and a portion of the RR-PCM can include structures represented by Formulas (la), (Ila),(la) (Ila)

[0061] In Formulas (I) and (la), X can be a linear aliphatic group. X can contain at least 40 carbon atoms. In certain aspects, X can vary randomly between the repeating units of Formula (I) and Formula (la), such as number of carbon atoms. In certain aspects, X does not vary between the repeating units of Formula (I). In some aspects, X can include 40 to 2,000, or equal to any one of, at least any one of, or between any two of 40, 45, 50, 55, 60, 65, 70, 80, 90, 100, 150, 200, 220, 240, 260, 280, 300, 320, 340, 360, 380, 400, 420, 440, 460, 480, 500, 520, 540, 560, 580, 600, 650, 700, 750, 800, 850, 900, 950, 1,000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000 carbon atoms. X can have a degree of saturation 97 to 100 %, or equal to any one of, at most any one of, or between any two 97, 97.5, 98, 98.5, 99, 99.5 and 100 %.

[0062] In Formulas (II), and (Ila), Y can be a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, 20 to 60 carbon atoms or 30 to 50 carbon atoms, or 14, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100 or any range or value there between of carbon atoms. In some instances, Y has 30 to 40 carbon atoms, preferably 32 to 35 carbon atoms. In preferred aspects, Y has less carbon atoms than X. For example, if Y has 100 carbon atoms, X will have 120 or more carbon atoms. In another example, if Y has 40 carbon atoms, X can have 50 or more carbon atoms. A is an amine group (-NH-), an oxygen (-O-), a carboxyl group (-COOH). In a preferred aspect -Y-A- has a general structure of Formulas (III).R11R12— A_S_ R14—C-CH?HR I13(III) where R11, R12, R13, R14are each individually saturated aliphatic hydrocarbons. R13and R14can from a cyclic saturated ring. A is amine group (-NH-), an oxygen (-O-), a carboxyl group (-COOH), or a combination thereof. The wavy line is the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (II). In some aspects, A is an oxygen atom, and Y-A- has the structures as shown in Formulas (IV) and (V):In Formulas (IV) and (V), a, b, c, and d are each individually integers from 1 to 25. The wavy lines are the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (II). In preferred aspects, a is 6, b is 5, c is 7, and d is 6 to form structures (IVa) and (Va).where the wavy line is the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (II).

[0063] In some aspects, a portion of the RR-PCM composition of the present invention has a structure as illustrated in Formulas (VI) and / or (VII).(VI), where a, b, c, d are each individually integers from 1 to 25, and / or(VII). In Formulas (VI) and (VII), n is an integer ranging from 2 to 13 and m is an integer ranging from 1 to 100. X has more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units. Although ketones are illustrated as side groups in Formulas (VI) and (VII), the one ormore side functional groups of Z can be one or more of hydroxyl (-OH), carboxylic acid (CO2H), amine (NH2), or a combination thereof, and the oxygens bonded to X can be ketones, amines, etc.R1-r— Z~ — R2

[0064] The difunctional linker can have the formula ' , R -Z-R2, where R1and R2are each OH, CO2H, NH2, or a combination thereof, and n is 2 to 13 carbon atoms. In some instances, Z can have a carbon chain of 2 to 13 carbon atoms (C2-C13), 2 to 10, or 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or any value or range there between. The two functional groups, R1and R2can be an amine (-NH2), an alcohol (-OH), a carboxylic acid (-COOH), or a combination thereof. In some instances, the difunctional linker is a cyclic acid, a cyclic amide, a diester, or a combination of a monoacid and an ester. The functionality “F” of the difunctional linker can be a statistical value of 2.0 ± 0.3, or 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3 or any value or range there between. Functionality can be measured using known chemical analysis, for example, titration methods. In some aspects, the difunctional linker can be oxalic acid, malonic acid, succinic acid, maleic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, citric acid, aconitic acid, isocitric acid, propane- 1,2, 3 -tricarboxylic acid, pentane-l,3,5-tricarboxylic acid, or any combinations thereof.

[0065] Reaction of a difunctional linker, a difunctional linear oligomer, and the Y-precursor can form the polymer having the repeating units of Formula (I) and Formula (II), and / or the RR-PCM of Formulas (III).

[0066] The difunctional linear oligomer can have a formula of,1, (“R3-X-R4”) where R3and R4are each OH, CO2H, NH2, or a combination thereof, and n can be 40 to 2000. In some aspects, X is a polyethylene or polypropylene polymer have 40 to 2000 carbon atoms, 60 to 1500 carbon atoms 80 to 1100 carbon atoms, or 40, 50, 60, 70, 80, 90, 100, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000 or any value or range therebetween of carbon atoms. X can have a degree of saturation of 98% to 100% or 98%, 98.5%, 99%, 99.5%, 99.9%, 100% or any value or range there between. Degree of saturation can be determined by NMR or other known chemistry methods. The two functional groups, R3or R4can be an amine (-NH2), an alcohol (-OH), a carboxylic acid (-COOH), or a combination thereof. The functionality “F” of the difunctional linear oligomer can be a statistical value of 2.0 ± 0.3, or1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3 or any value or range there between. Functionality can be measured using known chemical analysis, for example, titration methods.

[0067] In one aspect, the Y-A precursor is shown in Formula (VIII) where each A and A’ is an amine group (-NH-), a hydroxyl (-OH-), a carboxyl group (-COOH), or a combination thereof.

[0068] In a preferred aspect, Y-A can be derived from hydrogenation of dimeric fatty alcohols (e.g., A and A’ are both O). Non-limiting examples of dimeric fatty alcohols include oleic acid, linoleic acid, palmitoleic acid, eleostearic acid, ricinoleic acid, vemolic acid, licanic acid, myristoleic acid, margaroleic acid, gadoleic acid, eicosadienoic acid, and / or erucic acid. Dimers of a fatty alcohol are commercially available for example from Croda (trade name PRIPOL 2033) or Cognis (SOVERMOL 908). Both PRIPOL 2033 and SOVERMOL 908 are high purity, fully hydrogenated, and distilled aliphatic dimer alcohols. These products can be colorless, clear viscous liquids. The functionality “F” of the branched hydrocarbon moiety can be a statistical value of 2.0 ± 0.3, or 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3 or any value or range there between. Functionality can be measured using known chemical analysis, for example, titration methods where each A is an amine group (-NH-), a hydroxyl (-OH-), a carboxyl group (- COOH), or a combination thereof. ii. Additives

[0069] The compositions of the present invention can include at least one article additive, or optional additives. The article additive can be added when a RR-PCM of the present invention is made into an article. The article additive can be from the liquified article. Examples of such additives can include catalysts and additive that are useful for making articles. Nonlimiting examples of article additives can include, but are not limited to, an antioxidant, a metal deactivator, a processing aid, a UV stabilizer, a pigment, a phosphite, a phosphinate, a colorant, or mixtures thereof. In some embodiments, combinations of the article additives can be combined as an article package to be added to the composition. The choice of additive packages may be driven by the specific type of article being made and its intended use. For use in pipes intended for use with chlorinated water, for instance, additive packages comprising certaintypes of antioxidants can lead to synergistic results. Other articles can preferably be made with specific types of additive packages.

[0070] Non-limiting examples of article antioxidant additives can include 3, 3'3", 5,5', 5'- hexatert-butyl-alpha, alpha', alpha, "-(mesitylene-2, 4, 6-triyl )tri-p-cresol (CAS 1709-70-2) commercially known as Irganox 1330 (Ciba Specialty Chemicals) or Ethanox 330 (Albemarle Corporation); pentaerythritol tetrakis (3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) (CAS 6683-19-8) available as Irganox 1010 (Ciba Specialty Chemicals); octadecyl-3 -(3. 5-di- tert.butyl-4-hydroxyphenyl)-propionate (CAS 002082 79-3) available as Irganox 1076; 1,3,5- tris(3,5-di-tert-butyl 4-hydroxybenzyl)-l,3,5-triazine-2,4,6(lH.3H,5H)-trione (CAS 2767-62- 6) available as Irganox 3114; l,3,5-tris(4- tert-butyl-3-hydroxy-2,6-dimethyl benzyl) 1,3,5- triazine-2, 4,6-(lH,3H,5H)-trione (CAS 040601-76) available as Cyanox 1790 (CyTech Industries); ethylenebis(oxyethylene)bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)-propionate) (CAS 36443-68-2) available as Irganox 245; 1.6-hexamethylene bis (3,5-di(tert)-butyl-4- hydroxyhydrocinnamate (CAS35074-77-2) available as Irganox 259: thiodiethylene bis3-(3,5- di-tert-butyl-4-hydroxyphenyl) propionate (CAS 41484-35-9) available as Irganox 1035; tris(2,4-ditert-butylphenyl)phosphate (CAS 31570-04-4) available as Irgafos™ 168 and mixtures thereof.

[0071] Non-limiting examples of metal deactivators can include 2',3-bis(3-3,5-di-tert-butyl- 4-hydroxyphenylpropionylpropionohydrazide. (CAS 32687-78-8) available as Irganox™ MD 1024 and 2,2'-oxalyldiamidobis ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate (available as Naugard™ XL1), and mixtures thereof.

[0072] For every Use Cycle a RR-PCM is produced from a liquified article, a new additive and / or additive package can be used prior to making a new article so that the next RR-PCM that is made and used to make the new article, and the new article can have a higher amount of additive(s) when compared with the initial (prior to adding more additive) RR-PCM obtained from the liquified article. At a very high Use Cycle rating, when the amount additive(s) in a recycled RR-PCM are so much that the amount of additive(s) affects the functional properties of the copolymer(s) made, the recycled RR-PCM may not be substantially similar to the functional properties of virgin RR-PCM or conventional polyolefin copolymers. In some aspects, at some point, there may be so much additive in the recycled RR-PCM that the recycled RR-PCM may no longer function similar to the virgin RR-PCM or conventional polyolefin copolymer.

[0073] The amount of additives used to make an article can vary by application and can be from greater than 0 wt.% to 5 wt. %, or 0.00001 wt. %, 0.0001 wt. %, 0.001 wt. %, 0.01 wt.0.05 wt. %, 0.06 wt. %, 0.07 wt. %, 0.08 wt. %, 0.09 wt. %, 0.1 wt. %, 0.2 wt. %, 0.3 wt. %,0.4 wt. %, 0.5 wt.%, 0.6 wt. %, 0.7 wt. %, 0.8 wt. %, 0.9 wt. 1, 1 wt. %, 2 wt. %, 3 wt. % 4 wt. %, or 5 wt. %, or any number or range there between.

[0074] The composition can include one or more optional additives. Non-limiting examples of an optional additive can include a scratch-resistance agent, an antioxidant, a flame retardant, an UV absorber, a photochemical stabilizer, a filler such as glass and / or mineral filler, an optical brightener, a surfactant, a processing aid, a mold release agent, a pigment, flow modifiers, foaming agents, or any combinations thereof. In some aspects, the composition can include at least 95 wt.% to 100 wt.% (e.g., 95 wt.%, 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, 100 wt.% or any value or range there between) of the RR-PCM(s) and an optional additive. An amount of optional additive can be from greater than 0 to 5 wt. %, or 0.00001 wt. %, 0.0001 wt. %, 0.001 wt. %, 0.01 wt. 0.05 wt. %, 0.06 wt. %, 0.07 wt. %, 0.08 wt. %, 0.09 wt. %, 0.1 wt. %, 0.2 wt. %, 0.3 wt. %, 0.4 wt. %, 0.5 wt.%, 0.6 wt. %, 0.7 wt. %, 0.8 wt. %, 0.9 wt. 1, 1 wt. %, 2 wt. %, 3 wt. % 4 wt. %, or 5 wt. %, or any number or range there between. In some preferred aspects, the amount of the optional additive in the composition can be 0.0 wt.% to 0.2 wt.% or 0.01 wt.%, 0.05 wt.%, 0.1 wt.%, 0.15 wt.%, 0.2 wt.% or any value or range there between. In some embodiments, the composition include at least 0.01 % to 0.2 %, preferably 0.05 % to 0.15 %, of an optional additive and 95 wt.%, 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, 100 wt.% of the RR-PCM composition.B. Method of Making RR-PCM(s)

[0075] Certain aspects are directed to a method for making the RR-PCMs of the present invention. The method can include reacting a difunctional linear oligomer (e.g., oligomer R3- X-R4, where R3, R4are each OH, CO2H, NH2, or a combination thereof, with the linker compound) and a functionalized branched hydrocarbon moiety (e.g., Y-A precursor shown above in Formula VIII) with the difunctional linker (e.g., R -Z-R2. where R2and R2are each OH, CO2H, NH2, or a combination thereof, and / or the ester thereof, where Z is as defined above) compound under conditions sufficient to produce the RR-PCM of the present invention. Reaction conditions can include temperature and an inert atmosphere or vacuum (e.g., 5 Pa to 0.101 MPa) A reaction temperature can be 90 °C to 250 °C, or equal to any one of, at least any one of, or between any two of 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, and 250 °C. In some aspects, the reaction can include esterification at 90 °C to250 °C, under inert atmosphere, followed by polycondensation at 90 to 250 °C, under vacuum, e.g., at pressure of 0.0005 MPa, below 0.0001 MPa, below 0.00005 MPa.

[0076] In certain aspects, the reaction, (e.g., esterification and / or polycondensation) can be performed in presence of a catalyst. In some aspects, catalysts used can include, but are not limited to a mineral acid, organic acid, organic base, and / or metallic compound. In some aspects, the metallic compound can be a hydrocarbyl, oxide, chloride, carboxylate, alkoxide, aryloxide, amide, salen complex, P-ketiminato complex, or guanidinato complex, of a metal. In some aspects, the metal can be Li, Na, K, Mg, Ca, Sc, Y, lanthanides, Ti, Zr, Zn, Mo, Mn, Al, Ga, Bi, Sb, or Sn. In some aspects, the catalyst can be Ti(OiPr)4, Ti(OBu)4, Al(OiPr)3, Sn(2- ethyl-hexanoate)2, MoOs, or any combinations thereof. In certain aspects, a combination of catalysts can be used. In one aspect, a titanium tetraisopropoxide catalyst is used for the esterification reaction.C. Method of Making / Recycling the RR-PCM(s)

[0077] Certain aspects are directed to a method for making / recycling the composition of the present invention that includes the RR-PCM(s) of the present invention. Referring to FIG. 1, a system and method of making the composition of the present invention is illustrated. In a preferred aspect, FIG. 1 illustrates a closed loop system and method of recycling a RR-PCM(s) of the present invention. System 100 can include liquification unit 102, depolymerization unit 104, and polymerization unit 106. Plastic article 108 can enter liquification unit 102. Plastic article 108 can include or be a consumer product that includes polyolefin copolymer(s) and / or a composition of the present invention that includes a RR-PCM(s). In some preferred aspects, the article 108 is a plastic article. Non-limiting examples of consumer goods can include a packaging product, a pharmaceutical container, a bottle, a cap, a closure, a liner, a trash bag, a food packaging film, a lamination, a pipe, a hose, a fitting, or a combination thereof. In some aspects, the composition can contain a blend of the RR-PCM(s) of varying molecular weight. Plastic article 108 can be optionally cleaned of contaminants (e.g., inert materials) and shredded into smaller pieces prior to being fed to liquification unit 102. In liquification unit 102, plastic article 108 can be heated to melt the article (e.g., heated to a temperature of 120 °C to 250 °C) and produce a liquified article composition 110. Liquification unit 102 can be an extruder, stirred tank and / or a combination thereof. Liquified article composition 110 can include the RR-PCM(s) and an article additive.

[0078] Liquified article composition 110 can exit liquification unit 102 and enter depolymerization unit 104. In some instances, liquification unit 102 and depolymerization unit 104 can be the same unit. In depolymerization unit 104, liquified article composition 110 can be subjected to conditions to depolymerize the RR-PCM(s) in the liquified article composition to produce a liquified article comprising a mixture of difunctional linear oligomers, difimctional linkers, and functionalized branched hydrocarbon moieties. Depolymerization conditions can include temperature and pressure. Depolymerization temperature can be from 190 °C to 350 °C or 190 °C, 195 °C, 200 °C, 225 °C, 250 °C, 275 °C, 300 °C, 325 °C, 350 °C, or any range or value there between. A depolymerization pressure can range from 3 MPa to 4.5 MPa, or 3 MPa, 3.1 MPa, 3.2 MPa, 3.3 MPa, 3.4 MPa, 3.5 MPa, 3.6 MPa, 3.7 MPa, 3.8 MPa, 3.9 MPa, 4.0 MPa, 4.1 MPa, 4.2 MPa, 4.3 MPa, 4.4 MPa, 4.5 MPa, or any range or value there between. In some aspects, the depolymerization can be performed at an inert atmosphere. In some instances, the depolymerization conditions can be 195 °C to 205 °C at 3.8 to 4.0 MPa. At these reaction conditions, the RR-PCM(s)) depolymerizes and forms the difimctional linear oligomers, difimctional linkers, and functionalized branched hydrocarbon moieties. The difunctional linear oligomer can be a solid, liquid, or a combination thereof. The difimctional linkers can be a solid, liquid, or combination thereof. The functionalized branched hydrocarbon moiety can be a solid, liquid, or a combination thereof. Depolymerization can include hydrolysis and / or solvolysis (e.g., alcoholysis) of the RR-PCM(s) to obtain the difimctional linear oligomer R3-X-R4, where R3and R4are each OH, CO2H, NH2, or a combination thereof, the difimctional linker R -Z-R2. where R2and R2are each OH, CO2H, NH2, or a combination thereof, and the functionalized branched hydrocarbon moiety R7-Y -R8, where R7and R8are each OH, CO2H, NH2. In certain aspects, the depolymerization method can include methanolysis of the composition under conditions suitable to obtain the difimctional linear oligomer (e.g., R3-X-R4, where R3and R4are each OH,), a methyl ester of the difunctional linker (e.g., R -Z-R2. where R1and R2are masked acid (e.g., CH3O2C-Z-CO2CH3)), and functionalized branched hydrocarbon moiety (e.g., R7-Y-R8, where R7and R8are each OH, CO2H, NH2). Non-limiting examples of a catalyst used for methanolysis depolymerization can include a mineral acid, an organic acid, an organic base, and / or metallic compound. Nonlimiting examples of metallic compounds can include a metal complexed or bonded to a hydrocarbyl, an oxide, a chloride, a carboxylate, an alkoxide, an aryloxide, an amide, a salen ligan, a P-ketiminato ligand, or a guanidinato ligan. In some aspects, the metal can be Li, Na, K, Mg, Ca, Sc, Y, lanthanides, Ti, Zr, Zn, Mo, Mn, Al, Ga, Bi, Sb, or Sn. In some aspects, thecatalyst can be Ti(OiPr)4, Ti(OBu)4, Al(OiPr)3, Sn(2 -ethyl -hexanoate)2, MoOs, or any combinations thereof.

[0079] In some instances, depolymerization unit 104 can include one or more separation / purification units. The separation / purification units can be a part of depolymerization unit 104 or a separate unit (not shown). The separation units can separate the difunctional linear oligomers and / or the functionalized branched hydrocarbon moiety from the difunctional linkers from the depolymerization composition. For example, the difunctional linear oligomer(s) and / or the functionalized branched hydrocarbon moieties can be solids, and the difunctional linker(s) can be a liquid or vice versa. In such instances, the solid can be separated from the depolymerization composition using fdtration, centrifugation, precipitation, or other known separation techniques. In some instances, the liquid component can be separated from the depolymerization composition using distillation methods. In other instances, all compounds are liquids or solids and solid / solid or liquid / liquid separation / purification methods can be used to isolate the solids or liquids. Separation units can help to remove impurities and / or other unwanted items prior to repolymerization. In some aspects, oligomers, and linkers from other RR-PCM processes that are desired can be separated from the desired oligomers, linkers, and functionalized branched hydrocarbon moieties. For example, any homopolymers of PP, LDPE, HDPE or LLDPE, or a combination thereof can be separated from the RR-PCM difunctional linear oligomers. In some instances, functionalized branched hydrocarbon moiety 116 is not recycled.

[0080] In some aspects, difunctional linear oligomer stream 112 and / or difunctional linker stream 114 and / or functionalized branched hydrocarbon moiety 116 can exit depolymerization unit 104 and enter polymerization unit 106. In some instances, the streams exit depolymerization unit 104 as a single stream. In some aspects, the article additive is included in oligomer stream 112 and / or linker stream 114. In some instances, functionalized branched hydrocarbon moiety 116 does not enter polymerization unit 106. For example, functionalized branched hydrocarbon moiety 116 may not be recyclable. In some instances, depolymerization unit 104 and polymerization unit 106 are the same unit. In another instance, liquification unit 102, depolymerization unit 104, and polymerization unit 106 can be the same unit. In polymerization unit 106, difunctional linear oligomer 112, difunctional linker 114, and functionalized branched hydrocarbon moiety 116 (or a new functionalized branched hydrocarbon moiety) can be subjected to conditions to produce recycled RR-PCM(s). Said another way, the difunctional linear oligomers, difunctional linkers, and functionalizedbranched hydrocarbon moieties in streams 112, 114, and 116 can be repolymerized to form a recycled RR-PCM(s). In polymerization unit 106, the difunctional linear oligomers, functionalized hydrocarbon moieties, and difunctional linkers can be reacted at conditions described throughout this specification.

[0081] In some aspects, the difunctional linear oligomer (e.g., HO-X-OH) obtained from a liquefied article can be repolymerized with a difunctional linker (e.g., HO2C-Z-CO2H, an ester, and / or cyclic anhydride thereof (e.g., of the acid of HO2C-Z-CO2H)) and a functionalized branched hydrocarbon moiety (e.g., dimer of a fatty alcohol).

[0082] Recycled RR-PCM(s) 118 can exit polymerization unit 106 and be sold, transported, or formed into a consumer product. In some aspects, the article additive is included in the RR- PCM(s) 118. In some aspects, recycled RR-PCM(s) 118 is formed into a pellet to be sold, transported, or converted into a consumer product. As shown in FIG. 1, recycled RR-PCM(s) 118 exits polymerization unit 106 and enters converting unit 120. Converting unit 120 can be onsite or offsite. Converting unit 120 can be a commercial manufacture of consumer goods and / or articles of manufacture. In converting unit 120, recycled RR-PCM(s) 118 can be formed into recycled RR-PCM article 122 that includes the recycled RR-PCM(s) of the present invention. For example, recycled RR-PCM(s) 118 can be molded (e.g., extruded, injection molded, blow molded, compression molded, rotational molded, thermoformed and / or 3-D printed) to form recycled RR-PCM article 122. In some aspects, recycled RR-PCM article 122 can be comprised in or in the form of a foam, a film, a layer, a sheet, a molded article, a welded article, a filament, a fiber, a wire, a cable, or a powder. In one example, the composition is incorporated into a film. In some instances, the film may include at least one film layer that includes the composition. In some aspects, an article additive can be combined with the recycled RR-PCM(s) 118 prior to being sent to the converting unit 120. The additive can be an article additive package that is typically used with the article to be produced. In some aspects, an article additive is not combined with the recycled RR-PCM(s) 118 prior to being sent to the converting unit 120, which may be advantageous if the article being recycled, and the article being made are the same type or class of articles. In such an aspect, the additive present in the article being liquified in liquification unit 102 can be preserved throughout the liquification, depolymerization, and re -polymerization steps, such that no or reduced amounts of additive is added prior converting unit 120.

[0083] In some aspects, recycled RR-PCM article 122 can contain a blend of the RR- PCM(s) of varying molecular weight. In some aspects, recycled RR-PCM(s) article 122 canfurther include one or more additives. The additives can be added in polymerization unit 106 and / or converting unit 120. Non-limiting examples of additives can include, a scratchresistance agent, an antioxidant, a flame retardant, an UV absorber, a photochemical stabilizer, a fdler such as glass and / or mineral filler, an optical brightener, a surfactant, a processing aid, a mold release agent, a pigment, flow modifiers, foaming agents, or any combinations thereof.

[0084] Recycled RR-PCM(s) article 122 can exit converting unit 120 and be sold, transported, used, and / or stored. Recycled RR-PCM(s) article 122 can be used and collected by consumers 124. After use, used recycled RR-PCM(s) article 126 containing recycled RR- PCM(s) can be provided to liquification unit 102, and a new cycle can be started. The cycle of the present method can be continuously repeated (e.g., 2 to 500 times (e.g., 2, 5, 10, 15, 20, 25, 50, 75, 100, 125, 150, 175, 200, 225, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, or 500 times, or any value or range there between)). In one aspect, a closed-loop recycling of the RR- PCM(s) can now be realized.C. Articles

[0085] Compositions of the present invention that include the RR-PCM(s), recycled RR- PCMs, and / or additives can be shaped into useful articles by a variety of methods (e.g., injection molding, extrusion molding, rotation molding, foam molding, calendar molding, blow molding, thermoforming, compaction, melt spinning, and the like). Non-limiting examples of articles include consumer goods, packaging products, pharmaceutical containers, bottles, caps, closures, liners, trash bags, food packaging film and / or materials, laminations, pipes, hoses, or fittings.

[0086] Some additional non-limiting examples of articles include: external and / or internal components (e.g., panels, quarter panels, rocker panels, trim, fenders, doors, decklids, trunk lids, hoods, bonnets, roofs, bumpers, fascia, grilles, mirror housings, pillar appliques, cladding, body side moldings, wheel covers, hubcaps, door handles, spoilers, window frames, headlamp bezels, headlamps, tail lamps, tail lamp housings, tail lamp bezels, license plate enclosures, roof racks, and running boards) for transportation vehicles (e.g., aircraft, automotive, truck, military vehicle (including automotive, aircraft, and water-borne vehicles), scooter, and motorcycle); enclosures, housings, panels, and parts for outdoor vehicles and devices; enclosures for electrical and telecommunication devices; outdoor furniture; aircraft components; boats and marine equipment, including trim, enclosures, and housings; outboard motor housings; depth finder housings, personal water-craft; jet-skis; pools; spas; hot-tubs;steps; step coverings; building and construction applications such as glazing, roofs, windows, floors, decorative window furnishings or treatments; treated glass covers for pictures, paintings, posters, and like display items; wall panels, and doors; counter tops; protected graphics; outdoor and indoor signs; enclosures, housings, panels, and parts for automatic teller machines (ATM); computer; desk-top computer; portable computer; lap-top computer; palm- held computer housings; monitor; printer; keyboards; FAX machine; copier; telephone; phone bezels; mobile phone; radio sender; radio receiver; enclosures, housings, panels, and parts for lawn and garden tractors, lawn mowers, and tools, including lawn and garden tools; window and door trim; sports equipment and toys; enclosures, housings, panels, and parts for snowmobiles; recreational vehicle panels and components; playground equipment; shoe laces; lids for containers; articles made from plastic-wood combinations; golf course markers; utility pit covers; light fixtures; lighting appliances; network interface device housings; transformer housings; air conditioner housings; cladding or seating for public transportation; cladding or seating for trains, subways, or buses; meter housings; antenna housings; cladding for satellite dishes; coated helmets and personal protective equipment; coated synthetic or natural textiles; coated painted articles; coated dyed articles; coated fluorescent articles; coated foam articles; textiles, foot apparel, and like applications.

[0087] Additionally, the RR-PCM(s) or recycled RR-PCM(s) (with or without additives) can also be formed into films or sheets as well as components of laminate systems. The sheet can be a foam sheet, paper sheet, or fabric sheet. Articles include, for example, fibers, sheets, films, multilayer sheets, multilayer films, molded parts, extruded profiles, coated parts and foams, windows, luggage racks, wall panels, chair parts, lighting panels, diffusers, shades, partitions, lenses, skylights, lighting devices, reflectors, ductwork, cable trays, conduits, pipes, cable ties, wire coatings, electrical connectors, air handling devices, ventilators, louvers, insulation, bins, storage containers, doors, hinges, handles, sinks, mirror housing, mirrors, toilet seats, hangers, coat hooks, shelving, ladders, hand rails, steps, carts, trays, cookware, food service equipment, communications equipment and instrument panels.E. RR-PCM(s) Use Cycles

[0088] In some aspects, the RR-PCM(s) of the present invention exhibits favorable Use Cycle ratings such that recycled RR-PCM(s) can be made into different articles such that instead discarding each article can be liquefied and repolymerized into another RR-PCM(s) material. FIG. 2 is an illustration of Use Cycle 200. In Block 202, RR-PCM(s) (RR-PCM)n) is shown, where n is an integer (e.g., 0 to 10000, or more). In Block 204, an Articlen can be madefrom Block 202 RR-PCMn. When n is 1, this can represent Use Cycle 1. In Block 206, the Articlen from Block 204 made from RR-PCMn can be liquefied by heating and depolymerization as described above to produce difunctional linear oligomer(s) and difunctional(s) linkers of Articlen. In Block 208, the liquified Articlen of Block 206 (e.g., the difunctional linear oligomer(s) and difunctional linker(s) of the present invention) can be polymerized to produce RR-PCMn+i. In Block 210, the Articlen+i can be produced from the RR-PCMn+i of Block 208. When n is 2, this represents a Use Cycle of 2. Generally, the RR- PCM has a Use Cycle rating of at least 2. In Block 212, the process can be continued, where Articlen+i of Block 210 can be liquefied by heating and depolymerization as described above to produce difunctional linear oligomer(s) and difunctional(s) linkers. In Block 214, the liquified Articlen+i of Block 212 (e.g., the difunctional linear oligomer(s) and difunctional linker(s) of the present invention) can be polymerized to produce a new RR-PCM material to continue the cycle. In one embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 1000. In another embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 500. In another embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 400. In another embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 300. In another embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 300. In another embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 200. In another embodiment, the RR-PCM has a Use Cycle rating ranging from 2 to 100. In some aspects, theUse Cycle rating can be greater than 1000 (e.g., 1500, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, or more). In some aspects, the US Cycle rating can be 2, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, ormore, or any range ornumber therein.

[0089] Advantageously, the Use Cycle ratings can be achieved without having to use additional feed stock (e.g., virgin RR-PCM feed stock) or by using a limited amount of additional feed stock (5, 4, 3, 2, 1, 0.5, or 0 wt. % of virgin RR-PCM feed stock).

[0090] Remarkably, it is now possible to make a RR-PCM(s) that are functionally similar to conventionally made polyolefin copolymers, or a virgin RR-PCM, and that can be repeatedly reused. This can reduce or eliminate the use of single-use plastics and / or increase the efficiency of traditional chemical recycling processes. Instead of using the traditional process of making a copolymer(s) from monomers, the compositions, RR-PCM, and articles of the present invention can be made from difunctional linear oligomers and difunctional linkers obtainedfrom a recycled article that would have typically been discarded into a landfill or incinerated. Advantageously, the compositions, RR-PCM, articles, and / or processes of the present invention are highly efficient at being recycled and made into new articles (e.g., at least 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or 100 %, of RR-PCM obtained from an article can be recycled to produce a new article.F. RR-PCM(s) Composites

[0091] The RR-PCM(s) compositions of the present invention can be included in composites. Composites can be made into stacked polymeric compositions (e.g., laminates) used to form structures having advantageous structural characteristics, such as high strength, high stiffness and / or relatively low weight when compared to similar structures formed from conventional materials.

[0092] RR-PCM(s) composites or compositions of the present invention can be formed into any structure. Non-limiting examples of structures include sandwich-type structures, multilayered (stacked) composites and the like. The composite or compositions of the present invention can be dimensioned and shaped according to respective applications. Non-limiting examples of shapes include rectangular, triangular, square, polygonal (whether having sharp and / or rounded comers), circular, elliptical, or otherwise rounded, or can have an irregular shape or otherwise. The overall thickness of the composite or compositions can be up to and even exceeding several millimeters. Some embodiments of the present composites or compositions can include one or more openings, notches, and / or the like, which can facilitate incorporation of the composite into a structure. Composites or compositions of the present invention can have any thickness.

[0093] In some embodiments, the composite, compositions and / or stacked polymeric composition of the present invention can be decorated. In use, a surface of the composite or stacked polymeric compositions can be subjected to printing with ink. In an embodiment, an exposed surface of the composite or a stacked polymeric composition surface opposite the surface adjacent to the core can be subsequently decorated, in particular printed with markings such as alphanumerics, graphics, symbols, indicia, logos, aesthetic designs, multicolored regions, and a combination that includes at least one of the foregoing. In some embodiments, each composite can be decorated. In some embodiments, one of the exposed (or outer) surfaces of the composite can be subjected to common curing and / or surface modification processes.Non-limiting examples of such processes can include heat-setting, texturing, calendaring, embossing, corona treatment, flame treatment, plasma treatment, and vacuum deposition.

[0094] In some embodiments, the composite can include a cap layer material. The cap layer can be a fdm material made from a different polymer and process than the composite stacks (e.g., laminates). By way of example, it can be an extruded film material, which is for example chemical resistant to cleaning agents. Film materials used can include polyvinylidene fluoride (PVDF), polyvinyl fluoride (PVF), poly(methylmethacrylate) (PMMA), multilayered combinations and blends thereof. These film materials can be applied by roller lamination or double belt press lamination equipment. Also, aesthetic film materials can be used to produce, for example, a wood grain or metallic surface. The cap layer can be created by co-extrusion (single or multi -manifold). In some embodiments, an anti-microbial surface can be created by co-extrusion of film materials with silver or other germicides. In some embodiments, the cap layer can be made by screen-printing an aesthetic or functional ink layer. In most instances, these cap layers will be thermoformable.

[0095] The composites can be made using known panel consolidation techniques. By way of example, the composite can be made using continuous systems that include one or more machines capable of cutting, cooling, stacking, wrapping, or the like (for example, static heated presses, double belt presses and the like). In some embodiments, the composites and / or stacked polymeric compositions of the present invention can include at least 2 or 3, 4, 5, 6, 7, 8, 9, 10 or more RR-PCM(s) composites of the present invention having a thickness of about 0. 1 to 10 mm, or 0.25 to 5 mm. In some embodiments, when a core is present, the core density can be reduced to a desired density by patterning the core thermoplastic layer. In some embodiments, a stack of RR-PCM composites can be formed by heating and pressing more than one RR-PCM composites together. By way of example the composite stack can enter a first zone of a double belt press at a pressure of 5 to 15 N / cm2, or (0.5 to 1.5 MPa, or 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5 MPa or any value or range there between) and then heated to a temperature of 140 to 150 °C, (e.g., about 145 °C). The pressed stack can enter a second zone, be pressed, and the heated to 145 to 155 °C (e.g., about 150 °C). The pressed stack can enter a third zone, be pressed, and then heated at a temperature of 150 to 160 °C (e.g., about 155 °C) to form a composite of the present invention. In some embodiments, the surface of one RR-PCM composite can be treated with a coupling agent prior to assembling the stack.

[0096] Non-limiting examples of core materials can include RR-PCM(s) compositions of the present invention, polyethylene terephthalate (PET), a fire-retardant polypropylene (PP) orcopolymer thereof, a polycarbonate (PC) or a copolymer thereof, a polyimide / polyetherimides or a copolymer thereof, a polyethersulfone (PES), a polyurethane (PU), or a polyphenyl ether (PPO)Zstyrene blend, a PPO / polyamide blend, a PPE / polystyrene blend, a PPO / polypropylene blend a PPO-Si / polyamide blend, a PPO-Si / polystyrene blend, a PPO-Si / polypropylene blend, or any combination thereof. Thermoplastic cores can be produced or are available from various commercial sources. By way of example, a PET core can be obtained from commercial sources such as Armacell Benelux S.A. (Beligum) under the tradename of ArmaFORM®, or from Diab Group (Sweden) under the tradename of Divinylcell P. Fire-retardant polypropylene honeycomb cores can be obtained from EconCore N.V. (Belgium.) under the tradename ThermHex. Polyimide cores can be obtained from commercial suppliers such as DuPont™ (U.S.A.), Hexcel Corporation (U.S.A.), and the like. In some embodiments, a fiber reinforced composite of the present invention can include the RR-PCM(s) of the present invention, additives, fibers, and a coupling agent. More than one composite or composition of the present invention can be assembled to produce a stack (e.g., a laminate). A fiber-reinforced composite includes greaterthan or substantially equal to any one of, or between any two of l5, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 49.5, 49.9, or 49.95 wt.% of RR-PCM, based on the total weight of the fiber-reinforced composite.

[0097] Non-limiting examples of fibers include glass fibers, carbon fibers, aramid fibers, thermoplastic fibers, ceramic fibers, basalt fibers, steel fibers, and / or the like. Non-limiting examples of thermoplastic fibers include polyethylene fibers, polyester fibers, polyamide fibers with or without fire retardant additives (FR thermoplastic fibers) incorporated into the fiber. The fiber-reinforced composite can include, based on the total weight of the fiber-reinforced composite, 50 to 80 wt.% fibers or greater than or substantially equal to any one of, or between any two of: 50, 55, 60, 65, 70, 75, 80 wt.% fibers. Fibers (e.g., fibers 310 in FIG. 3) of a composite (e.g., composite 302, 304, 306, 308 in FIG. 3) can be provided in bundles (e.g., bundles of carbon, ceramic, carbon precursor, ceramic precursor, glass, and / or the like fibers). Such bundles may include any number of fibers, such as, for example, 400, 750, 800, 1,375, 1,000, 1,500, 3,000, 6,000, 12,000, 24,000, 50,000, 60,000, or more fibers. Fibers in a bundle can have an average filament diameter of 5, 6, 7, 8, 9, 10, 1 1, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, or more microns (e.g., from 5 to 30 microns, 10 to 20 microns, 12 to 15 microns, or any range there between). Fibers can be provided with a sizing (e.g., acoating of an organic polymer, such as an organosilane), a pigment, and / or the like. Fibers can also be provided as a woven mat.

[0098] In some embodiments, fillers (e.g., fibers) in the composite or compositions of the present invention can be sized. The sizing can include RR-polyolefm plasticizer, a RR- polyolefm elastomer, or a combination thereof. The sizing can range from about 0.01 wt.% to about 30 wt.% of the fiber component, or from about 0.1 wt.% to about 10 wt. % of the fiber component, or from about 1 wt.% to about 5 wt.% of the fiber component.

[0099] Fiber-reinforced composites can be made by dispersing fibers (sized or unsized) in a RR-PCM(s) matrix of the present invention using know fiber-reinforced composite methodology. For example, methods to prepare fiber-reinforced composites are described in International Application Publication No. WO 2016 / 142786 to Prins et al. In such a method, a sheet or film that includes the RR-PCM(s) can be supplied between a first and a second spreaded fiber layers. Heat can be applied to the fiber layer / polymer composition / fiber layer material, followed by pressing the fiber layers into the polymer composition. In some embodiments, after pressing is completed, the first or second fiber layers can be rubbed. In some embodiments, the fibers are not spread prior to heating. In another embodiment, the composites can be made by using known impregnation techniques. For example, Miller et al. in Polymers & Polymer Composites, 1996, Vol. 4, No. 7 describes impregnation techniques for thermoplastic matrix composites. One such method can include providing suppling fibers to one or more solution baths (e.g., RR-PCM(s) in one or two baths) to form resin impregnated fibers, drying the fibers, and then pressing the fibers to produce a fiber-reinforced composite (e.g., prepreg sheets). In another embodiment, the RR-PCM(s) and fibers can be stacked together, heated, and then pressed causing the resin to flow transverse to the fibers to from prepreg sheets of reinforced thermoplastic materials. Typically, the width and the length of the non-woven fibrous region are substantially similar to the width and the length, respectively, of the fiber-reinforced composite. Such fiber-reinforced composites can include, by volume, at least 35 to 70% of the plurality of continuous fibers.

[0100] In some aspects, a fiber-reinforced composite (e.g., a ply) or compositions of the present invention can be used to make a stacked polymeric composition (e.g., a laminate). In a plurality of fiber-reinforced composites, the fiber-reinforced composites can have a length and a width that is perpendicular to and smaller than the length, where the length and the width are each a distance between outer edges of the fiber-reinforced composite measured along a straight line. The length can be, but need not be, the largest such distance. Each of the fiber-reinforced composites can have a shape and dimensions that correspond to the shape and dimensions of the final material. To further illustrate, the largest face of each of the fiber- reinforced composites can have a surface area that is substantially equal to a surface area of the largest face of the final material. To illustrate yet further, each of the fiber-reinforced composites can be rectangular. In other embodiments, one or more fiber-reinforced composites of a stacked polymeric composition (e.g., a laminate) can have a shape and / or dimensions that differ from the shape and / or dimensions of the laminate; such fiber-reinforced composites can, for example, be used to add stiffness and strength to a portion of the laminate that is smaller than the entirety of the laminate. In some aspects, a mixture of fiber-reinforced composites and unreinforced composites are used to make stacked polymeric compositions. In a preferred aspects, the stacked polymeric composition is made of only RR-PCM composites of the present invention having fibers or sized fibers dispersed therein.

[0101] Referring to FIG. 3, composite 300 can be a stacked polymeric composition (e.g., a laminate) and include at least two fiber-reinforced composites. For example, four fiber- reinforced composites (e.g., fiber-reinforced composites 302, 304, 306 and 308). At least one fiber-reinforced composite can include a RR-PCM(s) polymeric matrix having a plurality of fibers 310 dispersed therein. Some embodiments of the present methods include producing a laminate (e.g., 300) at least by stacking two or more fiber-reinforced composites (e.g., including one or more of fiber-reinforced composites or composites in a 0 / 90 orientation). By way of example, at least 2 or 3, 4, 5, 6, 7, 8, 9, 10 or more RR-PCM(s) composites (e.g., fiber-reinforced composites and / or non-fiber containing composites) having a thickness of about 0.1 to 10 mm, or 0.25 to 5 mm can be stacked. During such stacking, any number of the laminates can be formed by placing sections (e.g., fiber-reinforced composites 302 and 304) of fiber-reinforced composite material, such as, for example, sections of unidirectional fiber composites, adjacent to one another. In some methods, the two or more polymeric composites include two or more unidirectional first fiber-reinforced composite and one or more unidirectional second fiber-reinforced composite, and the stacking is performed such that: (1) fibers of the first fiber-reinforced composite are aligned in a first direction; (2) fibers of the one or more second fiber-reinforced composite are aligned in a second direction that is perpendicular to the first direction; and (3) the one or more second fiber-reinforced composites are disposed in contact with one another and between two of the first fiber-reinforced composites.

[0102] RR-PCM(s) composites (e.g., 302, 304', 306, 308, etc.) that include fibers (e.g., fibers 310) can have a pre-consolidation fiber volume fraction (Vi) that is greater than or substantially equal to any one of, or between any two of: 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90%. In some embodiments of the present laminates, one or more fiber-reinforced composites may not include fibers; such fiber-reinforced composite can, for example, include a sheet of thermoplastic polymer material.

[0103] The laminates can be prepared using known lamination methods. It should be understood that laminates (e.g., laminate 300) can be made of fiber-reinforced composites having the same or different compositions. By way of example, fiber-reinforced composites 302, 304, 306 and 308 can each have a different composition or fiber-reinforced composites 302, 304, 306, and 308 can have the same or different compositions.

[0104] One or all of the fiber-reinforced composites (e.g., 302, 304, 306, 308, etc.) can include fibers (e.g., fibers 310) dispersed within a matrix material or pressed into the polymer matrix material. By way of example, the laminates can be prepare using a double belt press with integrated contact heating and cooling supplied by, for example Meyer® (Maschinenfabrik, Herber Meyer GmbH, Germany). The different fiber-reinforced composites (e.g., fiber-reinforced composites 302 and 304) can enter the heat press unit in a defined stacking sequence at a rate of 1.5 m / min. The fiber-reinforced composites stack can be pressed together in a first zone at a pressure of 0.1 to 0.4 N / cm2, or (1 to 4 kPa, or 1, 1.5, 2, 2.5, 3, 3.5, 4 kPa or any value or range there between) and then heated to a temperature of 170 to 185 °C, (e.g., about 180 °C). The pressed stack can enter a second zone, pressed, and the heated to 190 to 200 °C (e.g., about 195 °C). The pressed stack can enter a third zone, be pressed at a lower temperature of 185 to 195 °C (e.g., about 190 °C) to form the stack (e.g., laminate 300). Heating and cooling can be maintained without release of pressure. In some embodiments, a static heated press can be used.

[0105] In stack 300, each of the fiber-reinforced composites (e.g, plies 302, 304, 306, 308 etc.) can be a unidirectional fiber-reinforced composite, or a fiber-reinforced composite having fibers (e.g., fibers 310), substantially all of which are aligned in a single direction. More particularly, in each of the fiber-reinforced composites, the fibers can be aligned with either the length of stack 300 (e.g., fiber-reinforced composites 302, 308 of FIG. 3 each of which may be characterized as a 0-degree unidirectional fiber-reinforced composites) or the width of the stack (e.g., fiber-reinforced composites 304 and 306 of FIG. 3 each of which may becharacterized as a 90-degree unidirectional ply). The phrase, "aligned with" means within 10 degrees of parallel. Other embodiments of the present polymeric stacks of the present invention can include one or more unidirectional fiber-reinforced composites, each having fibers that are aligned in any suitable direction. For example, a unidirectional fiber-reinforced composite can include fibers aligned in a direction, where the smallest angle between the direction and a length of a stack including fiber-reinforced composite can be greater than or substantially equal to any one of, or between any two of: 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 degrees.

[0106] Some embodiments of the present polymeric stacks can include one or more fiber- reinforced composites, each having fiber-reinforced composites that define a woven structure (e.g., as in a fiber-reinforced composite having a plane, twill, satin, basket, leno, mock leno, or the like weave). For example, a fiber-reinforced composite can include a first set of fibers aligned in a first direction and a second set of fibers aligned in a second direction that is angularly disposed relative to the first direction, where the first set of fibers is woven with the second set of fibers. A smallest angle between first direction and second direction can be greater than or substantially equal to any one of, or between any two of: 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 degrees. The smallest angle between first direction and a length of a stack including such a fiber-reinforced composite can be greater than or substantially equal to any one of, or between any two of: 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 degrees.

[0107] Some embodiments of the present stacks can include one or more polymeric composite, each formed from sections of fiber-reinforced composites material. For example, a unidirectional fiber-reinforced composite can be formed from sections of unidirectional fiber material that has been placed adjacent to one another. To form such a fiber-reinforced composites, sections of fiber-reinforced composites material can be placed adjacent to one another manually and / or by an automated material laying machines

[0108] Some embodiments of the present stacked polymeric compositions (e.g., laminates) can include 0-degree unidirectional fiber-reinforced composites (e.g., plies) and 90-degree unidirectional fiber-reinforced composites stacked such that the 0-degree unidirectional plies are in contact with one another (meaning each is in contact with at least one other) and are disposed between two of the 90-degree unidirectional plies. In some embodiments, composites of the present invention (e.g., laminates) can include first and second sub-stacks of 90-degreeunidirectional fiber-reinforced composites and a third sub-stack of 0-degree unidirectional fiber-reinforced composites, where the third sub-stack is disposed between the first and second sub-stacks. In some embodiments, each of the sub-stacks can include three fiber-reinforced composites. However, in other embodiments, such sub-stacks can each be replaced with a single fiber-reinforced composite or can include 2, 3, 4, 5, 6, 7, 8, 9, or more fiber-reinforced composites . Other embodiments of the present stacked polymeric compositions can include any suitable fiber-reinforced composites (e.g., including one or more of any fiber-reinforced composite described above) stacked in any suitable configuration (e.g., balanced, symmetric, asymmetric, and / or the like).

[0109] Stacked polymeric compositions of the present invention can include coupling agents (e.g., tie layers) to adhere the composites together. FIG. 4 illustrates stacked polymeric composition 400. Stacked polymeric composition 400 can include fiber-reinforced composite layers 402 and 404 with tie layer 406. Composite layers 402 and 404 can include fibers 408 dispersed in a RR-PCM(s) matrix. Non-limiting examples of coupling agents (tie layer) can include polyolefin plastomers or derivatives thereof, polyolefin elastomers or derivatives thereof, maleic anhydride grafted polyethylene, maleic anhydride grafted ethylene copolymer, citric acid, styrene ethylene / butylene block copolymer with high styrene content, or a combination that includes at least one of the foregoing. The stacked polymeric composition can include, based on the total weight of the stack, 0. 1 to 2 wt.% coupling agent or greater than or substantially equal to any one of, or between any two of: 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, or 2 wt.% of coupling agent. In a preferred instance, no coupling agent is necessary.

[0110] The stacked polymeric compositions and / or composites can be recycled as described throughout this specification. When the composites or stacked polymeric compositions include fibers, the fibers can be removed after liquification of the RR-PCM(s) composite / stacked composition. For example, referring to FIG. 1, fibers and / or other fillers can be removed in liquefication unit 102 and / or in depolymerization unit 104.EXAMPLES[oni] The present invention will be described in greater detail by way of specific examples. The following examples are offered for illustrative purposes only and are not intended to limit the invention in any manner. Those of skill in the art will readily recognize a variety of noncritical parameters, which can be changed or modified to yield essentially the same results.Instrumentation

[0112] Thermal analysis was conducted on a DSC QI 00 from TA Instruments at a heating rate of 10 °C per minute. First and second runs were recorded after cooling down to about - 40 °C. The melting temperatures reported correspond to second runs.

[0113] HT-SEC Procedure . The molecular weight and dispersity were determined by means of high temperature size exclusion chromatography (HT-SEC) performed at 150 °C in a HT- SEC-IR instrument equipped with a IR4 detector (PolymerChar, Valencia, Spain). Three Polymer Laboratories 13 pm PLgel Olexis columns constitute the set. 1,2-dichlorobenzene (o- DCB) was purchased from VWR and used as an eluent at flow rate of 1 mL*min-l . Molecular weights and corresponding dispersities were calculated from HT-SEC analysis with respect to narrow polystyrene standards (PSS, Mainz, Germany).

[0114] Materials. Table 1 lists the materials used to make the RR-PCM(s) of the present invention.Table 1Example 1(Method of making Virgin RR-PCM)

[0115] Synthetic Scheme I illustrates the method of making of the RR-PCMs of the present invention using a fully saturated long chain linear diol, succinic acid, and a branched hydrocarbon diol.

[0116] A branched hydrocarbon diol (PRIPOL 2033 0.67 g, 2.5 mmol), a, co-dihydroxy hydrogenated polybutadiene (15.5 g, 10.0 mmol, made using the method described in WO 2022 / 214639 to Chinta et. al.), succinic acid (1.47 g, 12.5 mmol) and titanium tetra- isopropoxide (0.15 g) were introduced into a reactor and the reactor was then heated to 190 °C under stirring and in the presence of nitrogen atmosphere. The first stage, esterification was conducted for 2.5 hrs at atmospheric pressure. After that, the second stage, polycondensation was started by turning off the nitrogen, and by gradually reducing the pressure down to -0.05 mbar and the temperature was raised to 220 °C. After reacting for 3.0 hrs, the vacuum was released by bleeding in the nitrogen and the RR-PCM of the present invention was collected.FIG. 6 shows the 'H-NMR of the RR-PCM. Table 2 lists the thermal properties of the RR- PCM. FIG. 7 is the DSC of the RR-PCM. Table 3 lists molecular weight data and FIG. 8 a graphical illustration of the molecular weight. Table 4 lists the viscoelastic properties and FIG. 9 is a graphical illustration of the viscoelastic properties. Example 1 revealed a glass transition temperature of -113.0 °C, which is a typical region for polyethylenes. This sample revealed creep resistance after melting point and vitrimer-like behavior. Determination of extensional rheology was not possible due to shrinkage of samples upon thermal stimuli.Table 2*Based on DSC, where AHm° =288 J / g for pure PE crystalTable 3Table 4

[0117] Although embodiments of the present application and their advantages have been described in detail, it should be understood that various changes, substitutions, and alterations can be made herein without departing from the spirit and scope of the embodiments as defined by the appended claims. Moreover, the scope of the present application is not intended to be limited to the particular embodiments of the process, machine, manufacture, composition of matter, means, methods and steps described in the specification. As one of ordinary skill in the art will readily appreciate from the above disclosure, processes, machines, manufacture, compositions of matter, means, methods, or steps, presently existing or later to be developed that perform substantially the same function or achieve substantially the same result as the corresponding embodiments described herein can be utilized. Accordingly, the appended claims are intended to include within their scope such processes, machines, manufacture, compositions of matter, means, methods, or steps.

Claims

CLAIMS1. A repeatedly-recyclable copolymer mimic (RR-PCM) composition comprising repeating units according to Formula I and Formula II.where: n is an integer ranging from 2 to 13;Z and Z’ are each independently an aliphatic group;X is a polyolefin backbone comprising 40 to 2000 carbon atoms, preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms; andY is a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, preferably 20 to 60 carbon atoms, more preferably 30 to 50 carbon atoms; andA is an oxygen atom (O), a nitrogen atom (N), or a sulfur atom (S), preferably O atom, or combination thereof, wherein Formula (I) and / or Formula (II) have more than 0 and less than 40 ester groups per 1000 backbone (CTL) carbon units.

2. The RR-PCM composition of claim 1, wherein -Y-A- has a general structure of (III):are saturated aliphatic hydrocarbons and A is O, N, S atoms, R13and R14can from a cyclic saturated ring, and the wavy lines are the points of connection with the carbonyl oxygen atom in Formula (I) or Formula (III).

3. The RR-PCM composition of claims 1 or 2, wherein A is an oxygen atom and -Y-A- has general structures of Formulas (IV) or (V):where a, b, c, and d are each individually integers from 1 to 25 and the wavy lines are the point of connection with the carbonyl oxygen atom in Formula (I) or Formula (II).

4. The RR-PCM composition of any one of claims 1 or 2, having a structure of Formula(VI), where n is an integer ranging from 2 to 13, m is an integer ranging from 1 to 100, and a, b, c, d are each integers from 1 to 25,Z and Z’ are each independently an aliphatic group;X is a polyolefin backbone comprising 40 to 2000 carbon atoms, preferably 60 to 1500 carbon atoms, or more preferably 80 to 1100 carbon atoms; andY is a branched saturated hydrocarbon backbone having 14 to 100 carbon atoms, preferably 20 to 60 carbon atoms, more preferably 30 to 50 carbon atoms, wherein the RR-PCM composition has more than 0 and less than 40 ester groups per 1000 backbone (CH2) carbon units.

5. The RR-PCM composition of any one of claims 1 or 2, wherein the RR-PCM composition has a peak melting temperature (Tm) of 70 °C to 135 °C, a crystallinity temperature (Tc) of 60 °C to 135 °C, and / or wherein X has a degree of saturation of 98 % to 100%.

6. The RR-PCM composition of any one of claims 1 or 2, comprising 5 to 95 mol% of Y- A, 5 to 95 mol % of X with the balance being the linker.

7. The RR-PCM composition of any one of claims 1 or 2, wherein the RR-PCM composition is comprised in a composition that also comprises at least 0.001 wt.% to 3 wt.%, preferably 0.015 % to 0.15 %, of an additive, preferably an article additive.

8. The RR-PCM composition of any one of claims 1 or 2, wherein the RR-PCM composition has a molecular weight ranging from 20 kg / mol to 100 kg / mol and a polydispersity index ranging from 5 to 6.

9. The RR-PCM composition of any one of claims 1 or 2, wherein the RR-PCM composition of Formula (I) and / or Formula (II) are obtained from an article, wherein the article is a consumer good, a packaging product, a pharmaceutical container, a bottle, a cap, a closure, a liner, a trash bag, a food packaging fdm, a lamination, a pipe, a hose, a fitting, a foot apparel, or a combination thereof.

10. A method of making the RR-PCM composition of any one of the claims 1 or 2, the method comprising:(a) liquefying an article comprising the RR-PCM composition of any one of claims 1 or 2 into a mixture containing difunctional linear oligomers, difunctional linkers, and branched difunctional hydrocarbon moieties having 14 to 100 carbon atoms; and(b) reacting the difunctional linear oligomers, the difunctional linkers, and the branched difunctional hydrocarbon moieties having 14 to 100 carbon atoms to produce the RR-PCM.

11. The method of claim 10, wherein the RR-PCM composition from the liquified article is depolymerized prior to step (b) by hydrolysis and / or solvolysis by contacting the composition with water and / or a solvent to obtain the difunctional oligomers, difunctional linkers, and branched difunctional hydrocarbon having 14 to 100 carbon atoms wherein the article is liquefied by melting, and wherein forming an article from the RR-PCM composition produced in step (b) and / or wherein the method is repeated at least two times, preferably 2 to 500 times, and / or wherein the article is a consumer product.

12. A composite comprising the RR-PCM composition of any one of claims 1 or 2.

13. The composite of claim 12, comprising a filler having a surface in contact with the RR- PCM composition, preferably the filler is dispersed in the RR-PCM composition, wherein the filler is a continuous fiber or discontinuous fibers, preferably the fiber is a glass fiber, an aramid fibers a polyester fiber, a polyamide fiber, a basalt fiber, or a steel fiber, or combination thereof.

14. A laminate comprising a first layer comprising the RR-PCM composition of any one of claims 1 or 2 or the composite of any one of claims 12 or 13 and a second layer.

15. The laminate of claim 14, wherein the second layer comprises the RR-PCM composition of any one of claims 1 to 10 or the composite of any one of claims 12 to

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