Improvement of cold flow properties of pyrolysis oil

Abstract

The invention relates to the improvement of the cold flow properties of pyrolysis oil. These pyrolysis oils are manufactured by pyrolysis from plastic waste. In the process according to the invention, the pour point of the pyrolysis oil is reduced by adding at least one polyalkyl methacrylate copolymer selected from the group comprising polyalkyl methacrylate copolymers formed from monomer units of (A) 60.0 - 96.0 wt.-% of C12-C16 alkyl methacrylate; and (B) 40.0 - 4.0 wt.-% of C18-C30 alkyl methacrylate. Thereby, the cold flow properties of the pyrolysis oil are improved. The invention further relates to a pyrolysis oil further comprising said at least one polymer; and the use of said at least one polymer to improve the cold flow properties of such pyrolysis oil.

Description

Technical Field

[0001] The present invention relates to a method for improving the cold flow characteristics of pyrolysis oil made from plastic waste, and pyrolysis oil made from plastic waste having improved cold flow characteristics. Background Technology

[0002] Pyrolysis oils produced from the pyrolysis of plastic waste typically have pour points ranging from 0°C to 15°C or higher. Such high pour points negatively impact the cold-flow properties of these oils, especially when ambient temperatures are at or below their pour point. Therefore, handling such oils can be difficult or even impossible, for example, during a typical Central European winter, without the use of heated equipment such as pipes, pipelines, and (storage) tanks. This equipment is more expensive than comparable equipment without heating capabilities, particularly because the flash point of these oils is typically around or even below 50°C. Furthermore, the heating required for such equipment consumes energy, which has a negative impact on the climate. Improved cold-flow properties, for example, enhance the transportability and / or pumpability of pyrolysis oils and blends containing them through pipes, pipelines, machinery, etc.

[0003] Established methods for lowering the pour point of refined oils and related liquids derived from fossil fuels utilize added pour point depressants. However, due to the fundamental differences in composition between oils derived from petroleum and pyrolysis oils produced through the pyrolysis of plastic waste, such pour point depressants are not expected to significantly affect the pour point of these pyrolysis oils. Compared to oils derived from fossil fuels (which have very high concentrations of alkanes), pyrolysis oils have higher contents of heteroatoms (such as N, O, and S) and higher concentrations of olefins and aromatic compounds. Therefore, these pyrolysis oils are considered "unrefined oils" relative to refined oils from fossil fuels.

[0004] It is known that "pour point depressants have little or no effect on unrefined oils; in addition, these compounds themselves have some pour point depressing effect, and they act as antagonists against synthetic pour point depressants" (Lubricants and Special Fluids (Tribology Series, 23), V. Stepina, V. Vesely, Elsevier, 1992, pp. 372-375).

[0005] WO 2022056212 A1 discloses cold flow additives for synthetic raw materials used as plastic sources, selected from vinyl carboxylate polymers, α-olefin maleic anhydride polymers, or combinations thereof.

[0006] CN 106554828 A discloses a cold flow additive for marine heavy fuel oil selected from vinyl acetate copolymers and / or polymethacrylates.

[0007] The object of this invention is to provide a method for improving the cold flow characteristics of pyrolysis oil made from plastic waste and a blend containing at least one pyrolysis oil made from plastic waste.

[0008] Another object of the present invention is to provide pyrolysis oils produced from the pyrolysis of plastic waste with improved cold flow characteristics and blends comprising at least one of such pyrolysis oils. Summary of the Invention

[0009] These problems are addressed by a method for improving the cold flow characteristics of pyrolysis oil, the method comprising the following steps:

[0010] (i) Providing pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste.

[0011] (ii) Providing at least one polymer, wherein the at least one polymer is selected from the group consisting of alkyl methacrylate copolymers, which contain monomer units formed from:

[0012] (A) 60-96 wt.% C12-C16 alkyl methacrylates; and

[0013] (B) 40-4 wt.% C18-C30 alkyl methacrylates,

[0014] (iii) The at least one polymer provided in step (ii) is added to the pyrolysis oil provided in step (i), thereby improving the cold flow characteristics of the pyrolysis oil.

[0015] The pyrolysis oil formed in step (iii) is a product of the method according to the present invention.

[0016] These problems are further addressed by a pyrolysis oil having a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (as determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (as determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (as determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (as determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (as determined by ASTM D 5134) and / or a viscosity in the range of 0.5 mPas to 10 mPas (as determined by DIN). 53019 has a flash point measured at 40°C and / or in the range of 10°C to 75°C (measured according to DIN EN ISO 2719) and / or a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134), and further comprises at least one polymer selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from:

[0017] (A) 60.0-96.0 wt.% of C12-C16 alkyl methacrylates; and

[0018] (B) 40.0-4.0 wt.% of C18-C30 alkyl methacrylates.

[0019] These problems are further addressed by using at least one polymer in pyrolysis oil to improve the cold flow characteristics of the pyrolysis oil, the at least one polymer being selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from:

[0020] (A) 60-96 wt.% C12-C16 alkyl methacrylates; and

[0021] (B) 40-4 wt.% of C18-C30 alkyl methacrylate, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste. Detailed Implementation

[0022] The present invention is further described below with reference to embodiments, but the present invention is not limited to these embodiments, and any modifications or substitutions to these embodiments or combinations thereof within the basic spirit of the present invention are still within the scope of the present invention as claimed.

[0023] definition:

[0024] In the context of this specification and the appended claims, the term "about" preferably means a deviation of ±10% from the value described therein. In the context of this invention, the term "combination thereof" includes one or more of the listed elements. In the context of this invention, the term "mixture thereof" includes one or more of the listed elements.

[0025] "ppm" is defined in this document as "parts per million" mass / volume and corresponds to mg / l.

[0026] "ppmv" is defined in this paper as "parts per million volume" and is dimensionless.

[0027] The term "pour point" is defined herein as the lowest temperature at which a liquid (such as pyrolysis oil or diesel fuel) will flow under specific test conditions. Pour point is an important "cold flow" property for liquids used in cold environments or transported over long distances, as a high pour point can cause the liquid to become viscous and difficult to pump or flow through pipes, pipelines, or machinery. The pour point of pyrolysis oil or a blend containing at least one pyrolysis oil can be determined by methods according to DIN ISO 3016:2019 and ASTM D7346-15.

[0028] The phrase "monomer units formed from..." refers to the monomer units of the polymer formed after the monomer reaction. For example, C12-C16 alkyl methacrylate monomers are polymerized to give a polymer having units derived from C12-C16 alkyl methacrylates. Similarly, C18-C30 alkyl methacrylate monomers are polymerized to give a polymer having units derived from C18-C30 alkyl methacrylates.

[0029] In the context of this invention, the term "pyrolysis" refers to the thermal decomposition or degradation of plastic waste ("raw material") under inert conditions, producing gaseous, liquid, and solid char portions. During pyrolysis, the raw material is converted in a pyrolysis unit into a variety of chemicals, including gases such as H2, C1- to C4-alkanes, C2- to C4-olefins, acetylene, propyne, 1-butyne, pyrolysis oil having a boiling temperature of 25°C to 500°C or higher, and char. The direct products from this pyrolysis are "pyrolysis gas" and solid products. The liquid product "pyrolysis oil" is then separated from the "pyrolysis gas" by condensation. The term "pyrolysis" includes slow pyrolysis, fast pyrolysis, flash pyrolysis, and catalytic pyrolysis. These types of pyrolysis differ in process temperature, heating rate, residence time, raw material particle size, etc., resulting in different product qualities. Pyrolysis units can be operated adiabatic, isothermal, non-adiabatic, non-isothermal, or combinations thereof. The pyrolysis reactions disclosed herein can be carried out in a single stage or in multiple stages. For example, a pyrolysis unit can contain two reactor vessels connected in series by fluid. Thus, "pyrolysis oil" is produced from "plastic waste" through a pyrolysis process.

[0030] In the context of this invention, the term "pyrolysis oil" should be understood to mean any oil derived from the pyrolysis of plastic waste. The term "plastic waste" includes rubber waste (such as end-of-life tires), raw materials containing plastic waste (such as mixed plastic waste (MPW)), and raw materials derived from automotive shredder residue (ASR). Pyrolysis oil is obtained and / or is available from the pyrolysis of such plastic waste.

[0031] In the context of this invention, the term "plastic waste" preferably refers to any plastic material discarded after use, i.e., the plastic material has reached the end of its service life and is considered post-consumer waste. Plastic waste can be pure polymeric plastic waste, mixed plastic waste, or membrane waste, including sludge, adhesive materials, fillers, residues, etc. Plastic waste may have oxygen, nitrogen, sulfur, halogen, and optionally heavy metal content. Plastic waste can originate from any source containing plastic materials.

[0032] Therefore, the term "plastic waste" includes industrial and household plastic waste, as well as used tires and agricultural and horticultural plastic materials.

[0033] Typically, plastic waste is a mixture of different plastic materials, including hydrocarbon plastics such as polyolefins such as polyethylene (HDPE, LDPE) and polypropylene, polystyrene and their copolymers, and polymers composed of carbon, hydrogen and other elements such as chlorine, fluorine, oxygen, nitrogen, sulfur, silicon, etc., such as chlorinated plastics such as polyvinyl chloride (PVC), polyvinylidene chloride (PVDC), nitrogen-containing plastics such as polyamide (PA), polyurethane (PU), acrylonitrile butadiene styrene (ABS), oxygen-containing plastics such as polyesters such as polyethylene terephthalate (PET), polycarbonate (PC), silicone and / or sulfur-bridged crosslinked rubber.

[0034] Typically, plastic materials contain additives such as processing aids, plasticizers, flame retardants, pigments, light stabilizers, lubricants, impact modifiers, antistatic agents, antioxidants, etc. These additives may contain elements other than carbon and hydrogen. For example, the presence of bromine is primarily associated with flame retardants. Heavy metal compounds can be used as light-resistant pigments and / or stabilizers in plastics. Cadmium, zinc, and lead may be present in heat stabilizers and slip agents used in plastic manufacturing. Plastic waste may also contain residues. In the context of this invention, residues are contaminants that adhere to plastic waste. Additives and residues are generally present in amounts of less than 50 wt.-%, preferably less than 30 wt.-%, more preferably less than 20 wt.-%, and even more preferably less than 10 wt.-%, based on the total dry weight of the plastic.

[0035] Examples of rubber waste (also considered "plastic waste" in the context of this invention) include end-of-life tires, rubber waste generated during the manufacturing process, and discarded rubber-containing products such as latex inspection gloves and gaskets. End-of-life tires contain additional components, such as textiles, as well as organic and inorganic additives, which can be separated from the rubber portion of the end-of-life tire before pyrolysis. The pyrolysis oil obtained by (primarily) the pyrolysis of end-of-life tires is also known as tire pyrolysis oil (TPO).

[0036] To obtain the pyrolysis oil according to the invention, the feedstock is inserted into the pyrolysis reactor using a metering unit such as a screw, extruder, rotary valve, pneumatic conveyor, or liquid injector. The feedstock may optionally be preheated in, for example, a heat exchanger and / or subjected to pre-pyrolysis at a temperature, for example, in the range of about 200°C to about 360°C, before being inserted into the pyrolysis reactor. The feedstock is then heated in the pyrolysis reactor to a temperature in the range of about 350°C to about 900°C, more preferably in the range of 400°C to about 550°C, and a pressure in the range of about 0.5 bar to about 2 bar (absolute value), more preferably in the range of 0.9 bar to about 1.5 bar (absolute value).

[0037] The pyrolysis reactor is preferably selected from the group consisting of fluidized bed reactors, moving bed reactors, entrained flow reactors, screw reactors, extruders, stirred tank reactors, and rotary kiln reactors. Preferably, pyrolysis is carried out in the pyrolysis reactor under an inert atmosphere free of oxygen or air. Preferably, no water and / or hydrogen are intentionally added for pyrolysis.

[0038] Pyrolysis methods are known in themselves. They are described, for example, in EP 0713906 A1 and WO 95 / 03375 A1. Suitable pyrolysis oils are also commercially available. Pyrolysis oils are typically liquid at 15°C or waxy at said temperature. In the terminology of this invention, "liquid at 15°C" means that the pyrolysis oil has a density of at most 1.3 g / ml at 15°C and 1013 mbar, as determined according to DIN EN ISO 12185, preferably in the range of 0.65 to 0.98 g / ml.

[0039] Optionally, prior to step (i), the pyrolysis oil is subjected to one or more methods selected from: filtration, centrifugation, adsorption, washing, extraction, distillation, and hydrotreating. Such optional pretreatment methods are described, for example, in WO 2021 / 224287 A1, WO 2023 / 061834 A1, EP 0713906 A1, and WO 95 / 03375 A1, which are incorporated herein by reference. Those skilled in the art will understand how and in what circumstances to use the pretreatment methods disclosed in the aforementioned documents and comparable pretreatment methods disclosed elsewhere.

[0040] In step (i) of the method according to the invention, a pyrolysis oil or a blend containing at least one pyrolysis oil is provided. The at least one pyrolysis oil in the pyrolysis oil or blend is produced by pyrolysis of plastic waste as described above. Preferably, the at least one pyrolysis oil in the pyrolysis oil or blend is produced by pyrolysis of mixed plastic waste. More preferably, the mixed plastic waste comprises at least one member of the group consisting of: polyethylene, polypropylene, polystyrene, ethylene-propylene copolymer, polybutene, polybutadiene, or ethylene-propylene-diene rubber and copolymers thereof.

[0041] The pyrolysis oil preferably has a pour point in the range of -30°C to +60°C, more preferably -10°C to +30°C.

[0042] The pyrolysis oil provided in step (i) preferably has a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (as determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (as determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (as determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (as determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (as determined by ASTM D 5134) and / or a viscosity in the range of 0.5 mPas to 10 mPas (as determined by DIN). 53019 has a flash point measured at 40°C and / or in the range of 10°C to 75°C (measured according to DIN EN ISO 2719) and / or a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134). Such pyrolysis oils are particularly suitable for the methods, pyrolysis oils, and applications according to the present invention.

[0043] The pyrolysis oil provided in step (i) may be a single pyrolysis oil manufactured in a single batch or in more than one batch.

[0044] In step (ii) of the method according to the invention, at least one polymer is provided, the at least one polymer being selected from the group consisting of polyalkyl methacrylate copolymers, which contain monomer units formed from:

[0045] (A) 60-96 wt.% C12-C16 alkyl methacrylates; and

[0046] (B) 40-4 wt.% of C18-C30 alkyl methacrylates.

[0047] Preferably, component (A) accounts for 65 to 95 wt.-% of the formed polyalkyl methacrylate copolymer, and component (B) accounts for 35 to 5 wt.-% of the formed polyalkyl methacrylate copolymer.

[0048] The weight percentage (wt.-%) of components (A) and (B) of the formed alkyl methacrylate is calculated by dividing the total weight of component (A) or (B) by multiplying the total weight of the formed polyalkyl methacrylate copolymer by 100. The basis weight of the formed copolymer is the copolymer itself and does not include diluents.

[0049] The term "C12-C16 alkyl methacrylate" refers to alkyl esters of methacrylic acid having straight-chain or branched ester alkyl groups having 12 to 16 carbon atoms, such as lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, and mixtures thereof.

[0050] A preferred source of C12-C16 alkyl methacrylates is lauryl methacrylate, which contains a mixture of methacrylates formed from a mixture of C12-C16 alkyl alcohols. For example, a polymethacrylate copolymer is formed by about 60 to about 96 wt.-% of lauryl methacrylate as component (A), more preferably about 65 to about 95 wt.-% of lauryl methacrylate as component (A).

[0051] The term "C18-C30 alkyl methacrylate" refers to alkyl esters of methacrylic acid, having straight-chain or branched alkyl groups with 18 to 30 carbon atoms per group; such as stearyl methacrylate, octadecyl methacrylate, heptadecanyl methacrylate, nonadecanyl methacrylate, eicosyl methacrylate, dodecyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, octadecyl methacrylate, nonadecanyl methacrylate, triadecyl methacrylate, behenyl methacrylate, and mixtures thereof.

[0052] A preferred source of C18-C30 alkyl methacrylates is behenate methacrylate. Behenate methacrylate contains a series of long-chain methacrylates, wherein the ester chain length is in the range of C18 to C22. Behenate methacrylate is essentially linear and mainly contains C18-C22 alkyl methacrylates. Behenate methacrylate may contain a small amount of C16 alkyl groups.

[0053] Preferably, 40 to 5 wt.% of behenate methacrylate as component (B) constitutes the polyalkyl methacrylate copolymer provided in step (ii).

[0054] At least one polymer preferably has a mass-average molecular weight M of 5,000 to 250,000 g / mol, more preferably 10,000 to 150,000 g / mol, and most preferably 25,000 to 100,000 g / mol. wThe at least one polymer is selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from: (A) 60-96 wt.-% of C12-C16 alkyl methacrylate; and (B) 40-4 wt.-% of C18-C30 alkyl methacrylate.

[0055] The molecular weight distribution is preferably in the range of about 1.5 to about 2.5. Molecular weight distribution is defined as the mass-average molecular weight M. w Number-average molecular weight M n The ratio.

[0056] Mass-average molecular weight M w Preferably, the determination is performed using polymethyl methacrylate (PMMA) standards via gel permeation chromatography (GPC). Therefore, the determined mass-average molecular weight M... w It is relative to the standard product, not an absolute value.

[0057] Component (A) is a straight-chain or branched alkyl ester of methacrylic acid selected from the group consisting of:

[0058] Lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, and mixtures thereof.

[0059] Component (B) is a straight-chain or branched alkyl ester of methacrylic acid selected from the group consisting of:

[0060] Stearyl methacrylate, octadecyl methacrylate, nonadecanyl methacrylate, eicosyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, octadecyl methacrylate, nonadecanyl methacrylate, triadecanyl methacrylate, and behenyl methacrylate, and mixtures thereof.

[0061] Most preferably, component (A) is lauryl methacrylate and component (B) is behenyl methacrylate.

[0062] In the above definition, the C12-C16 alkyl residues in monomer unit (A) are selected from dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eggcosyl, docosyl, tridecyl, tetradecyl, pentadecyl, hexadecyl and their corresponding positional isomers; and the C18-C30 alkyl residues in monomer unit (B) are selected from octadecyl, nonadecanyl, squalyl and their higher homologues and their corresponding positional isomers.

[0063] C12-C16 alkyl residues with an even number of carbons are preferred in monomer unit (A).

[0064] C18-C30 alkyl residues with an even number of carbons are preferred in monomer unit (B).

[0065] The synthesis of polyalkyl methacrylate copolymers comprising monomer units formed from the following is described in paragraphs [0058-66] of EP2081970 B1:

[0066] (A) 60-96 wt.% C12-C16 alkyl methacrylates; and

[0067] (B) 40-4 wt.% of C18-C30 alkyl methacrylates.

[0068] In another aspect of the invention, in step (ii) at least one polyalkyl methacrylate copolymer (“Polymer 1”) is provided, comprising monomer units formed of: (A) 60-96 wt.% of C12-C16 alkyl methacrylate; and (B) 40-4 wt.% of C18-C30 alkyl methacrylate, and in step (ii) at least one additional polymer (“Polymer 2”), and then in step (iii) both are added to the pyrolysis oil provided in step (i) or a blend comprising at least one pyrolysis oil.

[0069] Therefore, the cold flow characteristics of the pyrolysis oil can be improved even further. More preferably, the ratio of "polymer 1" to "polymer 2" is in the range of 1:9 to 9:1, more preferably 2:8 to 8:2.

[0070] At least one polymer provided in step (ii) is added to the pyrolysis oil provided in step (iii) in step (i). This improves the cold flow characteristics of the pyrolysis oil by lowering its pour point.

[0071] At least one polymer can be added to the pyrolysis oil by pouring the polymer into the pyrolysis oil. Preferably, the pyrolysis oil is stirred so that the at least one polymer can be uniformly distributed in the pyrolysis oil.

[0072] The concentration of at least one polymer in the pyrolysis oil, or, in the case where more than one polymer is provided in step (ii) and added in step (iii), the total concentration of all polymers provided in step (ii) and added in step (iii) is preferably in the range of 10 to 3500 ppmv, more preferably 20 to 3000 ppmv, and most preferably 50 to 2500 ppmv.

[0073] When at least one polymer is added to pyrolysis oil in the form of a solution or dispersion, the uniform distribution of at least one polymer in the pyrolysis oil can be improved.

[0074] Optionally, in step (ii), at least one polymer is provided in the diluent. Suitable diluents are, for example, fractions obtained in petroleum processing, such as kerosene, naphtha, or bright oil (“base oil”). Aromatic hydrocarbons and aliphatic hydrocarbons, as well as alkoxyalkanols, are also suitable. In the case of middle distillates, particularly preferred diluents for diesel fuels and heating oils are naphtha, kerosene, diesel fuel, aromatic hydrocarbons (such as heavy solvent naphtha, Solvesso, or Shellsol®), and mixtures of these solvents and diluents.

[0075] The polymer according to the invention is preferably present in the solution or dispersion in an amount of 0.1 to 80 wt.-%, more preferably 1 to 70 wt.-%, and most preferably 20 to 60 wt.-%, based on the total weight of the solution or dispersion.

[0076] At least one polymer may be used in pyrolysis oil or blends containing at least one pyrolysis oil to improve the cold flow properties of the pyrolysis oil, wherein the at least one polymer is selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from:

[0077] (A) 60-96 wt.% C12-C16 alkyl methacrylates; and

[0078] (B) 40-4 wt.% of C18-C30 alkyl methacrylate, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste. The pour point of the pyrolysis oil preferably decreases after the addition of the at least one polymer. This improves the cold flow characteristics of the pyrolysis oil.

[0079] Optionally, at least one paraffinic dispersant may be added to the pyrolysis oil provided in step (i) of the method according to the invention, or to a blend containing at least one pyrolysis oil. Preferably, in step (iii), at least one optional paraffinic dispersant may be added to the pyrolysis oil.

[0080] Optionally, the pyrolysis oil according to the invention further comprises at least one paraffinic dispersant.

[0081] Such paraffinic dispersants can be added to prevent wax from settling in the pyrolysis oil. Paraffinic dispersants are believed to work by disrupting the formation of wax crystals, reducing the size of the wax crystals and thereby preventing the accumulation of solid wax and further improving the cold flow characteristics of the pyrolysis oil.

[0082] At least one optional paraffinic dispersant is preferably selected from the group consisting of: polyacrylates, formaldehyde coupling phenols, and condensation products of aliphatic fatty amines, alkyl succinimides, phthalimides and glutarimides with carbonyl compounds.

[0083] Particularly suitable paraffin dispersants are disclosed in WO 2021 / 126342 A1.

[0084] The concentration of at least one optional paraffinic dispersant, or the sum of all paraffinic dispersants when more than one paraffinic dispersant is added to the pyrolysis oil, is preferably in the range of 10 to 1500 ppmv, more preferably 20 to 1200 ppmv, and most preferably 50 to 1000 ppmv.

[0085] The invention is further illustrated by the following set of embodiments and combinations of embodiments derived from the indicated dependencies and reverse references. In particular, it should be noted that in each instance in which a series of embodiments is mentioned, for example in the context of the term "method / process as described in any one of embodiments 1 to 3," each embodiment in this series is intended to clearly disclose to those skilled in the art that the wording of the term should be understood by those skilled in the art to be synonymous with "method as described in any one of embodiments 1, 2, and 3." Furthermore, it should be clearly noted that the following set of embodiments represents a suitable structural portion of the general description of preferred aspects of the invention and, therefore, appropriately supports the claims of the invention.

[0086] 1. A method for improving the cold flow characteristics of pyrolysis oil, the method comprising the following steps:

[0087] (i) Providing pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste.

[0088] (ii) Providing at least one polymer, wherein the at least one polymer is selected from the group consisting of alkyl methacrylate copolymers, which contain monomer units formed by:

[0089] (A) 60-96 wt.% C12-C16 alkyl methacrylates; and

[0090] (B) 40-4 wt.% C18-C30 alkyl methacrylates,

[0091] (iii) The at least one polymer provided in step (ii) is added to the pyrolysis oil provided in step (i), thereby improving the cold flow characteristics of the pyrolysis oil.

[0092] 2. The method according to Example 1, wherein the pyrolysis oil preferably has a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (determined by ASTM D 5134) and / or a viscosity in the range of 0.5 mPas to 10 mPas (according to DIN 1159). 53019 is measured at 40°C and / or at a flash point in the range of 10°C to 75°C (measured according to DIN EN ISO 2719) and / or at a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

[0093] 3. The method according to any one of Examples 1 or 2, wherein the pyrolysis oil is produced by pyrolysis of mixed plastic waste.

[0094] 4. The method according to any one of Examples 1 to 3, wherein (A) is a straight-chain or branched alkyl ester of methacrylic acid selected from the group consisting of: lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, and mixtures thereof.

[0095] 5. The method according to any one of Examples 1 to 4, wherein (B) comprises about 40 to about 50 wt.-% of C18 alkyl methacrylate, about 5 to about 15 wt.-% of C20 alkyl methacrylate and about 40 to about 50 wt.-% of C22 alkyl methacrylate based on the total weight of (B) of the at least one polyalkyl methacrylate copolymer provided in step (ii).

[0096] 6. The method according to any one of Examples 1 to 5, wherein (A) is lauryl methacrylate and (B) is behenyl methacrylate.

[0097] 7. The method according to any one of Examples 1 to 6, wherein the polymer has a mass-average molecular weight M of 5,000 to 250,000 g / mol, more preferably 10,000 to 150,000 g / mol, and most preferably 25,000 to 100,000 g / mol. w .

[0098] 8. The method according to any one of Examples 1 to 7, wherein the concentration of the at least one polymer in the pyrolysis oil is preferably in the range of 10 to 3500 ppmv, more preferably 20 to 3000 ppmv, and most preferably 50 to 2500 ppmv.

[0099] 9. The method according to any one of Examples 1 to 8, wherein the pyrolysis oil further comprises at least one paraffinic dispersant, wherein the paraffinic dispersant is selected from the group consisting of: polyacrylates, formaldehyde coupling phenols, and condensation products of aliphatic fatty amines, alkyl succinimides, phthalimides and glutarimides with carbonyl compounds.

[0100] 10. The method according to Example 9, wherein the concentration of the at least one paraffinic dispersant in the pyrolysis oil is in the range of 10 to 1500 ppmv, more preferably 20 to 1200 ppmv, and most preferably 50 to 1000 ppmv.

[0101] 11. The method according to any one of Examples 1 to 10, comprising the following steps:

[0102] - The product obtained by the method according to any one of Examples 1 to 10 or by converting a chemical material that is obtainable or acquireable by the method according to any one of Examples 1 to 10 is used to obtain product PRF1.

[0103] 12. The method according to Example 11, wherein the product PRF1 is selected from:

[0104] i) Building blocks or single units; or

[0105] ii) a polymer, preferably polymer A, a polymer composition, preferably polymer composition A, or a polymer product, preferably polymer product A; or

[0106] iii) Cleaning polymers, cleaning surfactants, descaling compounds, cleaning biocides, or combinations thereof; or

[0107] iv) Agricultural chemical compositions, agricultural chemical formulations, adjuvants, or agricultural chemical active ingredients; or

[0108] v) Active pharmaceutical ingredients or intermediates thereof, pharmaceutical excipients, animal feed additives, human food additives, dietary supplements, aromatic chemicals or aromatic compositions; or

[0109] vi) Aqueous polymer dispersions, preferably polyurethane or polyurethane-poly(meth)acrylate hybrid polymer dispersions; emulsions, base materials for paper and fiber coatings, UV-curable acrylic polymers for hot melts and coatings, polyisocyanates, hyperbranched polyester polyols, polymer dispersants for inorganic binder compositions, unsaturated polyester polyols, or 100% curable compositions; or

[0110] vii) Cosmetic surfactants, emollients, waxes, cosmetic polymers, UV filters, other cosmetic ingredients, or combinations thereof or formulations thereof; or

[0111] viii) Polymer B, polymer composition B, coating composition, other functional composition, foil, molded body, coating or coated substrate.

[0112] 13. A pyrolysis oil having a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (as determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (as determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (as determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (as determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (as determined by ASTM D 5134) in the range of 0.5 mPas to 10 mPas (measured at 40°C according to DIN 53019) and / or a flash point in the range of 10°C to 75°C (as determined by DIN EN 1159). (Measured according to ISO 2719) and / or a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134), and further comprising at least one polymer selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from:

[0113] (A) 60.0-96.0 wt.% of C12-C16 alkyl methacrylates; and

[0114] (B) 40.0-4.0 wt.% of C18-C30 alkyl methacrylates.

[0115] 14. The pyrolysis oil according to Example 13, wherein the pyrolysis oil is produced by pyrolysis of mixed plastic waste.

[0116] 15. The pyrolysis oil according to Example 13 or 14, wherein (A) is a straight-chain or branched alkyl methacrylate selected from the group consisting of: lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, and mixtures thereof; and / or wherein (B) comprises about 40 to about 50 wt.-% of C18 alkyl methacrylate, about 5 to about 15 wt.-% of C20 alkyl methacrylate, and about 40 to about 50 wt.-% of C22 alkyl methacrylate based on the total weight of (B) in the at least one polyalkyl methacrylate copolymer provided in step (ii).

[0117] 16. The pyrolysis oil according to Example 15, wherein the C12-C16 alkyl residues in monomer unit (A) are selected from the group consisting of: dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, and their positional isomers.

[0118] 17. The pyrolysis oil according to Example 14 or 15, wherein the C18-C30 alkyl residues in monomer unit (B) are selected from the group consisting of: octadecyl, nonadecanyl, eggcosyl, dodecyl, triadecanyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, triacontyl, and their positional isomers.

[0119] 18. The pyrolysis oil according to any one of Examples 14 to 17, wherein the concentration of the at least one polymer in the pyrolysis oil is in the range of 10 to 3500 ppmv, more preferably 20 to 3000 ppmv, and most preferably 50 to 2500 ppmv.

[0120] 19. The pyrolysis oil according to any one of Examples 14 to 18, wherein the pyrolysis oil further comprises at least one paraffinic dispersant, wherein the paraffinic dispersant is selected from the group consisting of: polyacrylates, formaldehyde coupling phenols, and condensation products of aliphatic fatty amines, alkyl succinimides, phthalimides and glutarimides with carbonyl compounds.

[0121] 20. The pyrolysis oil according to Example 19, wherein the concentration of the at least one paraffinic dispersant in the pyrolysis oil is in the range of 10 to 1000 ppmv, more preferably 20 to 800 ppmv, and most preferably 50 to 600 ppmv.

[0122] 21. Use of at least one polymer in pyrolysis oil for improving the cold flow properties of said pyrolysis oil, said at least one polymer being selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from:

[0123] (A) 60.0-96.0 wt.% of C12-C16 alkyl methacrylates; and

[0124] (B) 40.0-4.0 wt.% of C18-C30 alkyl methacrylates, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste.

[0125] 22. The use according to Example 21, wherein the polyalkyl methacrylate copolymers comprise monomer units formed from: (A) 60.0-96.0 wt.-% of C12-C16 alkyl methacrylates; and (B) 40.0-4.0 wt.-% of C18-C30 alkyl methacrylates.

[0126] 23. The use according to Example 21 or 22, wherein the C12-C16 alkyl residues in monomer unit (A) are selected from the group consisting of: dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, and their positional isomers.

[0127] 24. The use according to any one of Examples 21 to 23, wherein the C18-C30 alkyl residues in the monomer unit (B) are selected from the group consisting of: octadecyl, nonadecanyl, eggcosyl, dodecyl, triadecanyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, triacontyl, and their positional isomers.

[0128] 25. The use according to any one of Examples 21 to 24, wherein the concentration of the at least one polymer in the pyrolysis oil is preferably in the range of 10 to 3500 ppmv, more preferably 20 to 3000 ppmv, and most preferably 50 to 2500 ppmv.

[0129] 26. The use according to any one of Examples 21 to 25, wherein the pyrolysis oil preferably has a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (determined by ASTM D 5134) and / or a viscosity in the range of 0.5 mPas to 10 mPas (according to DIN 1159). 53019 is measured at 40°C and / or at a flash point in the range of 10°C to 75°C (measured according to DINEN ISO 2719) and / or at a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

[0130] 27. The use according to any one of Examples 21 to 26, wherein the pyrolysis oil is produced by pyrolysis of mixed plastic waste.

[0131] 28. The use according to any one of Examples 21 to 27, wherein the pyrolysis oil further comprises at least one paraffinic dispersant, wherein the paraffinic dispersant is selected from the group consisting of: polyacrylates, formaldehyde coupling phenols, and condensation products of aliphatic fatty amines, alkyl succinimides, phthalimides and glutarimides with carbonyl compounds.

[0132] 29. The use according to Example 28, wherein the concentration of the at least one paraffinic dispersant in the pyrolysis oil is in the range of 10 to 1500 ppmv, more preferably 20 to 1200 ppmv, and most preferably 50 to 1000 ppmv.

[0133] The present invention further relates to a method according to any one of Examples 1 to 10, wherein the content of the pyrolysis oil having improved cold flow characteristics or a blend containing at least one pyrolysis oil in the product PRF1 is 1 wt.-% or more, preferably 2 wt.-% or more, more preferably 5 wt.-% or more, more preferably 15 wt.-% or more, more preferably 30 wt.-% or more, more preferably 40 wt.-% or more, more preferably 60 wt.-% or more, more preferably 80 wt.-% or more, more preferably 90 wt.-% or more, more preferably 95 wt.-% or more; and / or wherein the content of the pyrolysis oil having improved cold flow characteristics or a blend containing at least one pyrolysis oil in the product PRF1 is 100 wt.-% or less, preferably 95 wt.-% or less, more preferably 90 wt.-% or less, more preferably 50 wt.-% or less, more preferably 25 wt.-% or less, more preferably 10 wt.-% or less. wt.-% or less; and preferably wherein the content is determined based on a source retention and / or separation and / or quality balance and / or certificate statement chain of custody model, preferably based on quality balance, preferably the International Sustainable Development and Carbon Certification (ISCC) standard.

[0134] Publication Prior Art Disclosure; No. 684; paragraphs

[1000] to

[8005] ; ISSN: 2198-4786 (published: February 12, 2024) shall be regarded as reference RF1 and is incorporated herein by reference in its entirety. Preferably, product PRF1 is the product as described in paragraphs

[1000] to

[8005] of reference RF1. Preferably, the method described herein is further a method for producing product, preferably product PRF1.

[0135] The conversion steps for obtaining product PRF1 preferably include one or more steps as described below, and can be carried out by conventional methods well known to those skilled in the art. The conversion steps preferably include one or more steps selected from: recycling, preferably depolymerization, gasification, pyrolysis and / or steam cracking; and / or purification, preferably crystallization, (solvent) extraction, distillation, evaporation, hydrogenation, absorption, adsorption and / or ion exchange; and / or assembling, preferably foaming, synthesis, chemical conversion, chemical transformation, polymerization and / or blending; and / or shaping, preferably foaming, extrusion and / or molding; and / or finishing, preferably coating and / or smoothing. Additionally, one or more steps are described in detail in paragraphs

[1000] to

[8005] of reference RF1.

[0136] As used herein, the term "building unit" includes compounds that are in a gaseous or liquid state under standard conditions of 0°C and 0.1 MPa. Building units are typically used in the chemical industry to form secondary products that offer greater structural complexity and / or higher molecular weight than the building unit on which the secondary products are based. Building units are preferably selected from the group consisting of free hydrogen, carbon monoxide, carbon dioxide, ethylene oxide, ethylene glycol, syngas containing mixtures of hydrogen and carbon monoxide, alkanes, alkenes, alkynes, and aromatic compounds. Alkanes, alkenes, alkynes, and aromatic compounds particularly contain 1 to 12 carbon atoms, respectively.

[0137] As used herein, the term "monomer" includes molecules that can react with each other to form polymer chains through polymerization. Monomers are preferably selected from the group consisting of: (meth)acrylic acid, salts of (meth)acrylic acid; particularly sodium, potassium, and zinc salts; (meth)acrylaldehyde and (meth)acrylates. (Meth)acrylates containing 1 to 22 carbon atoms, particularly 1 to 8 carbon atoms, are preferred. The terms (meth)acrylic acid, (meth)acrylaldehyde, or (meth)acrylate refer to acrylic acid, acrolein, or acrylates, and where applicable, also refer to methacrylic acid, methacrolein, or methacrylates. Furthermore, monomers may be selected from hexamethylenediamine (HMD) and adipic acid. The building blocks may further be intermediate compounds. As used herein, the term "intermediate compound" includes organic reagents that are used to form compounds with higher molecular complexity. Intermediate compounds may, for example, be selected from the group consisting of phosgene, polyisocyanates, and propylene oxide. Polyisocyanates are particularly aromatic diisocyanates and polyisocyanates, preferably toluene diisocyanate (TDI) and / or diphenylmethane diisocyanate (MDI). The building blocks and monomers, as well as one or more typical conversion steps for obtaining the building blocks or monomers, are described in more detail in paragraphs

[1000] through

[1012] of reference RF1.

[0138] As used herein, the term "polymer A" includes thermoplastics (e.g., polyamides or thermoplastic polyurethanes), thermosetting plastics (e.g., polyurethanes), elastomers (e.g., polybutadiene), or copolymers or mixtures thereof, and is defined in more detail in paragraphs

[2001] through

[2007] of reference RF1. As used herein, the term "polymer composition A" includes all compositions comprising the polymer as described above and one or more additives (e.g., reinforcing agents, colorants, modifiers, and / or flame retardants), and is defined in more detail in paragraph

[2008] of reference RF1. As used herein, the term "polymer product A" includes any product comprising polymer A and / or polymer composition A as described above, and is defined in more detail in paragraphs

[2009] and

[2010] of reference RF1. One or more steps for obtaining a polymer (preferably polymer A), a polymer composition (preferably polymer composition A), or a polymer product (preferably polymer product A) are described in more detail in paragraph

[2011] of reference RF1.

[0139] As used herein, the term "industrial polymer" includes rheological polymers based on polycarboxylate, alkoxylated polyalkyleneamine, alkoxylated polyalkyleneimide, polyether, dye-inhibiting and dirt-releasing cleaning polymers, as defined in more detail in paragraphs

[3035] through

[3044] of reference RF1. As used herein, the term "industrial surfactant" includes nonionic, anionic, and amphoteric industrial surfactants, as defined in more detail in paragraphs

[3008] through

[3034] of reference RF1. As used herein, the term "industrial descaling compound" includes nonphosphate-based detergent builders (NPB) and phosphonates (CoP), as described in more detail in paragraphs

[3001] through

[3005] of reference RF1. As used herein, the term "industrial biocide" refers to compounds that kill or inhibit the growth or reproduction of microorganisms, as defined in more detail in paragraphs

[3006] through

[3007] of reference RF1. As used herein, the term “industrial solvent” includes alkylamides, alkyl lactamides, alkyl esters, lactates, alkyl diesters, cyclic alkyl diesters, cyclic carbonates, aromatic aldehydes, and aromatic esters, as defined in more detail in paragraphs

[3045] through

[3055] of reference RF1. As used herein, the term “industrial dispersant” includes anionic and nonionic industrial dispersants, as defined in more detail in paragraphs

[3056] through

[3058] of reference RF1. The term “composition and / or formulation thereof” with respect to industrial polymers, industrial surfactants, scale-removing compounds, and / or industrial biocides refers to industrial compositions and / or institutional products and / or textile and household care products and / or personal care products, as defined in more detail in paragraph

[3059] of reference RF1. One or more conversion steps for obtaining industrial polymers, industrial surfactants, scale-removing compounds, and / or industrial biocides are defined in more detail in paragraph

[3060] of reference RF1. The conversion steps for obtaining industrial compositions or formulations of industrial polymers, industrial surfactants, scale-removing compounds and / or industrial biocides are defined in more detail in paragraph

[3061] of reference RF1.

[0140] As used herein, the term "agrochemical composition" typically refers to a composition comprising an agrochemical active ingredient and at least one agrochemical formulation adjuvant. Examples of agrochemical compositions, active ingredients, and adjuvants are described in more detail in paragraph

[4001] of reference RF1. Agrochemical compositions may be in any conventional formulation form. These agrochemical compositions are prepared in known ways, for example, as described in: Mollet and Grubemann, Formulationtechnology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. One or more conversion steps to obtain the agrochemical active ingredient and adjuvant may be similar to one or more generation steps of its analogues based on petrochemicals or other precursors not obtained by recycling methods. Furthermore, the conversion of compounds mentioned in the chapters “Polymers” and “Cosmetic Surfactants, Emollients, Waxes, Cosmetic Polymers, UV Filters, Other Cosmetic Ingredients or Compositions thereof” can be carried out as described in those chapters and the corresponding paragraphs in reference RF1.

[0141] As used herein, the terms active pharmaceutical ingredient and / or its intermediates include substances that provide pharmacological activity or other direct effects or influence the structure or any function of the body in the diagnosis, cure, relief, treatment, or prevention of a disease. Intermediates are isolated products generated during a multi-step synthetic route of the active pharmaceutical ingredient. As used herein, the term pharmaceutical excipient includes compounds or mixtures of compounds used in compositions for various pharmaceutical applications that are substantially non-pharmaceutical in themselves. Active pharmaceutical ingredients and / or their intermediates, as well as pharmaceutical excipients, are defined in more detail in paragraph

[5001] of reference RF1. One or more conversion steps used to obtain active pharmaceutical ingredients and / or their intermediates, as well as pharmaceutical excipients, may include one or more synthetic steps and can be carried out by conventional synthesis and techniques well known to those skilled in the art.

[0142] As used herein, the terms animal feed additives, human food additives, and dietary supplements include vitamins, provitamins, and their active metabolites, including intermediates and precursors, especially vitamins A, B, E, D, and K and their esters (such as acetates, propionates, and palmitates) or their alcohols (such as retinol) or their salts or any combination thereof; tetraterpenes, especially isoprene-like compounds, such as carotenoids and lutein, including their intermediates and precursors and mixtures and derivatives thereof, especially β-carotene, canthaxanthin, hesperidin, astaxanthin, zeaxanthin, lutein, lycopene, apocarotenoids, and any combination thereof; Organic acids, especially formic acid, propionic acid and their salts (such as sodium, calcium or ammonium salts) and any combination thereof, such as, but not limited to, formic acid and sodium formate, propionic acid and ammonium propionic acid, formic acid and propionic acid, formic acid and sodium formate, and mixtures of propionic acid, propionic acid and sodium propionic acid and formic acid and sodium formate; glycerides of carboxylic acids and short and medium-chain fatty acids, conjugated linoleic acid (such as omega-6 fatty acid (C18:2) methyl esters) and 1,2-propanediol; and beverage stabilizers such as polyvinylpyrrolidone polymers or polyvinylimazole / polyvinylpyrrolidone copolymers. Animal feed additives, human food additives and dietary supplements are defined in more detail in paragraph

[5002] of reference RF1. One or more conversion steps used to obtain animal feed additives, human food additives, and dietary supplements may include one or more synthetic steps and may be carried out by conventional synthesis and techniques well known to those skilled in the art.

[0143] As used herein, aromatic chemicals and aromatic compositions include volatile organic compounds with a molecular weight between 70 and 250 g / mol, comprising a carbon skeleton of C5-C6. 16 Functional groups of carbon atoms, the carbon skeleton including straight chains, branches, and rings (e.g., rings with a size of C5-C). 18 The aromatic chemicals are bicyclic or tricyclic aliphatic chains, but do not necessarily contain one or more unsaturated structural elements such as double bonds, triple bonds, aromatic or heteroaromatic groups, and preferably, one or more additional functional groups are selected from alcohols, ethers, esters, ketones, aldehydes, acetals, carboxylic acids, nitriles, thiols, and amines. In one aspect, the aromatic chemicals are terpenoid-based aromatic chemicals, such as those selected from monoterpenes and monoterpenoids, sesquiterpenes and sesquiterpenoids, diterpenes, triterpenes, or tetraterpenes. Aromatic chemicals can be combined with other aromatic chemicals to obtain aromatic compositions. Aromatic chemicals and aromatic compositions are defined in more detail in paragraph

[5003] of reference RF1. One or more transformation steps used to obtain aromatic chemicals and aromatic compositions may include one or more synthetic steps and can be carried out by conventional synthesis and techniques well known to those skilled in the art.

[0144] As used herein, the term "aqueous polymer dispersion" includes one or more aqueous compositions comprising one or more dispersed polymers, and is defined in more detail in the section entitled "Aqueous Polymer Dispersions" of reference RF1

[6001] . One or more dispersed polymers may be selected from one or more acrylic emulsion polymers, one or more styrene acrylic emulsion polymers, one or more styrene butadiene dispersions, one or more aqueous dispersions comprising composite material particles, one or more acrylate-alkyd hybrid dispersions, one or more polyurethanes (including UV-curable polyurethanes), and one or more polyurethane-poly(meth)acrylate hybrid polymers. As used herein, the term "emulsion polymer" includes one or more polymers prepared by free radical emulsion polymerization. One or more aqueous polyurethane dispersions are defined in more detail in the section entitled "Polyurethane Dispersions" of reference RF1

[6002] . One or more UV-curable polyurethanes are defined in more detail in the section entitled "Polyurethane Dispersions" of reference RF1

[6017] . One or more polyurethane-poly(meth)acrylate hybrid polymers are defined in more detail in the section

[6016] of reference RF1. As used herein, the term "polymer dispersant" preferably includes one or more polymers comprising polyether side chains, particularly one or more polycarboxylate ether polymers and one or more condensation products as defined in more detail in the paragraph entitled "Polymer Dispersants"

[6020] of reference RF1. One or more conversion (polymerization) steps for obtaining one or more aqueous polymer dispersions comprising one or more emulsion polymers are defined in more detail in the section entitled "Emulsion Polymerization"

[6003] of reference RF1.

[0145] One or more conversion (polymerization) steps for obtaining one or more aqueous polyurethane dispersions are defined in more detail in the sections entitled "Methods for the Preparation of Aqueous Polyurethane Dispersions"

[6014] and "UV-Cureable Aqueous Polyurethane Dispersions, Their Preparation and Uses, and Compositions Containing Them"

[6017] of reference RF1. One or more compositions and uses of one or more aqueous polymer dispersions and one or more polymer dispersants are defined in more detail in the following sections of reference RF1: the section entitled "Uses of Aqueous Polymer Dispersions"

[6004] , the section entitled "Base Materials for Building and Construction Coatings"

[6005] , the section entitled "Base Materials for Paper Coatings"

[6006] , the section entitled "Base Materials for Fiber Bonding"

[6007] , and the section entitled "Adhesive Polymers and Adhesive Compositions". Section

[6008] , Section

[6015] entitled “Waterborne polyurethane dispersions suitable for use in coating compositions”, Section

[6016] entitled “Waterborne polyurethane-poly(meth)acrylate hybrid polymer dispersions suitable for use in coating compositions”, Section

[6017] entitled “UV-curable waterborne polyurethane dispersions, their preparation and use and compositions containing them”, Section

[6018] entitled “Inorganic binder compositions containing polymer dispersants and their use”,

[6019] 100% curable coating compositions.

[0146] One or more UV-crosslinkable poly(meth)acrylates and their uses are defined in more detail in the section entitled “UV-crosslinkable poly(meth)acrylates for use in UV-curable solvent-free hot melt adhesives and their use in the preparation of pressure-sensitive self-adhesive articles” in reference RF1

[6009] .

[0147] One or more polyisocyanates, one or more compositions comprising them, and their uses are defined in more detail in the section entitled "Polyisocyanates" of reference RF1

[6010] . One or more hyperbranched polyester polyols and their uses are defined in more detail in the section entitled "Organic solvent-based hyperbranched polyester polyols suitable for coating compositions" of reference RF1

[6011] . One or more conversion steps for obtaining hyperbranched polyester polyols are defined in more detail in the section entitled "Preparation of organic solvent-based hyperbranched polyester polyols" of reference RF1

[6012] . One or more coating compositions comprising one or more hyperbranched polyester polyols, one or more polyisocyanates, and one or more additives, and one or more substrates coated thereon are defined in more detail in the section entitled "Organic solvent-based two-component coating compositions comprising hyperbranched polyester polyols and polyisocyanates" of reference RF1

[6013] . One or more unsaturated polyester polyols, one or more solvent-based coating compositions comprising said one or more unsaturated polyester polyols, and one or more substrates for coating with said one or more coating compositions are defined in more detail in the section entitled “Coating Compositions Containing Unsaturated Polyester Polyols” in reference RF1

[6018] . One or more 100% curable coating compositions are defined in more detail in the section

[6019] of reference RF1.

[0148] One or more polymeric dispersants for use in inorganic binder compositions are defined in more detail in section

[6020] of reference RF1. One or more inorganic binder compositions comprising polymeric dispersants and their uses are defined in more detail in section

[6021] of reference RF1. One or more conversion steps for obtaining one or more polymeric dispersants are defined in more detail in section

[6020] of reference RF1. As used herein, the term "inorganic binder composition" comprising one or more polymeric dispersants preferably includes, in particular, hydraulic coagulating compositions and compositions comprising calcium sulfate, and is defined in more detail in section

[6021] of reference RF1 entitled "Inorganic Binder Compositions Containing Polymer Dispersants and Their Uses". Specific one or more building material formulations comprising one or more polymeric dispersants, or one or more building products produced from building material formulations containing polymeric dispersants, are disclosed in more detail in section

[6021] of reference RF1.

[0149] As used herein, the term “cosmetic surfactant” includes nonionic, anionic, cationic, and amphoteric surfactants, and is defined in more detail in paragraph

[7002] of reference RF1. As used herein, the term “emollient” refers to a compound used to protect, moisturize, and / or lubricate the skin, and is defined in more detail in paragraph

[7003] of reference RF1. As used herein, the term “wax” includes pearlescent agents and opacifiers, and is defined in more detail in paragraph

[7004] of reference RF1. As used herein, the term “cosmetic polymer” includes any polymer that can be used as an ingredient in cosmetic formulations, and is defined in more detail in paragraph

[7005] of reference RF1. As used herein, the term “UV filter” refers to a compound that blocks or absorbs ultraviolet light, and is defined in more detail in paragraph

[7006] of reference RF1. As used herein, the term “additional cosmetic ingredient” includes any ingredient suitable for the preparation of cosmetic formulations. Several sources disclose ingredients acceptable for cosmetic use. For example, the Cosing database on the European Commission's website discloses cosmetic ingredients, as does the International Dictionary and Handbook of Cosmetic Ingredients edited by the Personal Care Products Association (PCPC). The term "compositions and / or formulations thereof" in relation to cosmetic surfactants, emollients, waxes, cosmetic polymers, UV filters, and / or other cosmetic ingredients refers to personal care and / or cosmetic compositions or formulations as defined in more detail in paragraph

[7007] of reference RF1. One or more conversion steps used to obtain cosmetic surfactants, emollients, waxes, cosmetic polymers, UV filters, or other cosmetic ingredients are defined in more detail in paragraph

[7008] of reference RF1.

[0150] The terms “polymer B”, “polymer composition B”, “coating composition”, “other functional composition”, “foil”, “molded body”, “coating” and “coated substrate” are well known to those skilled in the art and are defined in more detail from paragraphs

[8000] to

[8005] of reference RF1.

[0151] The present invention will be further explained through the following non-limiting examples. Example

[0152] Before and after the addition of the polymer according to the invention or the polymer disclosed in the prior art, the pour point of the pyrolysis oil produced by pyrolysis of the mixed plastic waste raw material (“pyrolysis oil 1”) was measured using a pour point analyzer MPP 5GS from ISL Corporation according to the method of ASTM D7346-15.

[0153] When provided in step (i), pyrolysis oil 1 has a pour point of +6°C. In addition, pyrolysis oil 1 has the following characteristics: a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (determined by ASTM D 5134) in the range of 0.5 mPas to 10 mPas (measured at 40°C according to DIN 53019) and / or a flash point in the range of 10°C to 75°C (measured by DIN 5134). (Measured according to EN ISO 2719) and / or C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

[0154] Three different polymers were added to pyrolysis oil 1 at different concentrations, and the pour point of the pyrolysis oil containing the polymers according to the invention was measured again.

[0155] Polymer 1 (according to the invention): a polyalkyl methacrylate copolymer comprising monomer units formed of: (A) = lauryl methacrylate and (B) = behenyl methacrylate, wherein the weight ratio of (A) : (B) is about 70 : 30.

[0156] Polymer c1 (Comparative): Polymer used for comparative examples, alkyl acrylate-ethylene-vinyl ester copolymer (disclosed in WO 2022 / 056212 A1).

[0157] Polymer c2 (comparison): The polymer used for comparison example 2, a homopolymer based on lauryl acrylate.

[0158] The results of pyrolysis oil 1 are summarized in Table 1:

[0159]

[0160] Compared to polymer c1, which does not cause a change in the initial pour point, and polymer c2, which causes only a slight decrease in the initial pour point, as disclosed in WO 2022 / 056212 A1, polymer 1 causes a significant decrease in the initial pour point of pyrolysis oil 1. Therefore, compared to polymers known from the prior art, the cold flow characteristics of pyrolysis oil 1 are improved when the polymer according to the invention is added.

Claims

1. A method for improving the cold flow characteristics of pyrolysis oil, the method comprising the following steps: (i) Providing pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste. (ii) Providing at least one polymer, wherein the at least one polymer is selected from the group consisting of alkyl methacrylate copolymers, which contain monomer units formed from: (A) 60-96 wt.% C12-C16 alkyl methacrylates; and (B) 40-4 wt.% C18-C30 alkyl methacrylates, (iii) The at least one polymer provided in step (ii) is added to the pyrolysis oil provided in step (i), thereby improving the cold flow characteristics of the pyrolysis oil.

2. The method according to claim 1, wherein, The pyrolysis oil has a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (determined by ASTM D5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (determined by ASTM D 5134) and / or a viscosity in the range of 0.5 mPas to 10 mPas (measured at 40°C according to DIN 53019) and / or a flash point in the range of 10°C to 75°C (measured by DIN EN ISO). 2719 measurement) and / or C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

3. The method according to any one of claims 1 or 2, wherein, This pyrolysis oil is produced by the pyrolysis of mixed plastic waste.

4. The method according to any one of claims 1 to 3, wherein, (A) is a straight-chain or branched alkyl ester of methacrylic acid selected from the group consisting of: lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, and mixtures thereof.

5. The method according to any one of claims 1 to 4, wherein, (B) comprises 40 to 50 wt.-% of C18 alkyl methacrylate, 5 to 15 wt.-% of C20 alkyl methacrylate and 40 to 50 wt.-% of C22 alkyl methacrylate based on the total weight of (B) of the at least one polyalkyl methacrylate copolymer provided in step (ii).

6. The method according to any one of claims 1 to 5, wherein, (A) is lauryl methacrylate and (B) is behenyl methacrylate.

7. The method according to any one of claims 1 to 6, wherein, The concentration of at least one polymer in the pyrolysis oil is in the range of 10 to 3500 ppmv.

8. The method according to any one of claims 1 to 7, wherein, At least one paraffinic dispersant is added to the pyrolysis oil, wherein the at least one paraffinic dispersant is selected from the group consisting of: polyacrylates, formaldehyde coupling phenols, and condensation products of aliphatic fatty amines, alkyl succinimides, phthalimides and glutarimides with carbonyl compounds.

9. The method according to claim 8, wherein, The concentration of at least one paraffinic dispersant in the pyrolysis oil is in the range of 10 to 1500 ppmv.

10. The method according to any one of claims 1 to 9, comprising the following steps: - The product according to any one of claims 1 to 9 or a chemical material that can be obtained or acquired by the method according to any one of claims 1 to 9 is converted to obtain product PRF1.

11. The method according to any one of claims 10, wherein, The product PRF1 was selected from: i) Building blocks or single units; or ii) a polymer, preferably polymer A, a polymer composition, preferably polymer composition A, or a polymer product, preferably polymer product A; or iii) Cleaning polymers, cleaning surfactants, descaling compounds, cleaning biocides, or combinations thereof; or iv) Agricultural chemical compositions, agricultural chemical formulations, adjuvants, or agricultural chemical active ingredients; or v) Active pharmaceutical ingredients or intermediates thereof, pharmaceutical excipients, animal feed additives, human food additives, dietary supplements, aromatic chemicals or aromatic compositions; or vi) Aqueous polymer dispersions, preferably polyurethane or polyurethane-poly(meth)acrylate hybrid polymer dispersions; emulsions, base materials for paper and fiber coatings, UV-curable acrylic polymers for hot melts and coatings, polyisocyanates, hyperbranched polyester polyols, polymer dispersants for inorganic binder compositions, unsaturated polyester polyols, or 100% curable compositions; or vii) Cosmetic surfactants, emollients, waxes, cosmetic polymers, UV filters, other cosmetic ingredients, or combinations thereof or formulations thereof; or viii) Polymer B, polymer composition B, coating composition, other functional composition, foil, molded body, coating or coated substrate.

12. A pyrolysis oil having a bromine value of 2 g Br2 / 100 g to 150 g Br2 / 100 g (as determined by ASTM 1159) and / or a C5 hydrocarbon content of 0.03 wt.-% to 12.2 wt.-% (as determined by ASTM D 5134) and / or a naphthalene content of 0.02 wt.-% to 18.4 wt.-% (as determined by ASTM D 5134) and / or a styrene content of 0.02 wt.-% to 29.5 wt.-% (as determined by ASTM D 5134) and / or a toluene content of 0.25 wt.-% to 71.5 wt.-% (as determined by ASTM D 5134) in the range of 0.5 mPas to 10 mPas (measured at 40°C according to DIN 53019) and / or a flash point in the range of 10°C to 75°C (as determined by DIN 5134). (Measured according to EN ISO 2719) and / or a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134), and further comprising at least one polymer selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from: (A) 60-96 wt.% C12-C16 alkyl methacrylates; and (B) 40-4 wt.% of C18-C30 alkyl methacrylates.

13. The pyrolysis oil according to claim 12, wherein, This pyrolysis oil is produced by the pyrolysis of mixed plastic waste.

14. The pyrolysis oil according to claim 12 or 13, wherein, (A) is a straight-chain or branched alkyl methacrylate selected from the group consisting of: lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, dodecyl methacrylate, tridecyl methacrylate, tetradecyl methacrylate, pentadecyl methacrylate, hexadecyl methacrylate, and mixtures thereof; and / or wherein (B) comprises about 40 to about 50 wt.-% of C18 alkyl methacrylate, about 5 to about 15 wt.-% of C20 alkyl methacrylate, and about 40 to about 50 wt.-% of C22 alkyl methacrylate based on the total weight of (B) in the at least one polyalkyl methacrylate copolymer provided in step (ii).

15. The pyrolysis oil according to any one of claims 12 to 14, wherein, (A) is lauryl methacrylate and (B) is behenyl methacrylate.

16. The pyrolysis oil according to any one of claims 12 to 15, wherein, The concentration of at least one polymer in the pyrolysis oil is in the range of 10 to 3500 ppmv.

17. Use of at least one polymer in pyrolysis oil for improving the cold flow properties of said pyrolysis oil, said at least one polymer being selected from the group consisting of polyalkyl methacrylate copolymers comprising monomer units formed from: (A) 60-96 wt.% C12-C16 alkyl methacrylates; and (B) 40-4 wt.% of C18-C30 alkyl methacrylate, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste.

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