Improvement of cold flow properties of pyrolysis oil

Abstract

This invention relates to improvements in the cold flow properties of pyrolysis oils and blends containing at least one pyrolysis oil. These pyrolysis oils are produced by the pyrolysis of plastic waste. In the method according to the invention, the pour point of the pyrolysis oil and the blend containing at least one pyrolysis oil is lowered by adding at least one polymer selected from the group consisting of: hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-hydrocarbon-vinyl-ether copolymers, and hydrocarbon methacrylate-hydrocarbon-vinyl-ether copolymers. This improves the cold flow properties. The invention further relates to pyrolysis oils and blends containing at least one pyrolysis oil, which further contain said at least one polymer, and the use of said at least one polymer for improving the cold flow properties of such pyrolysis oils and blends containing at least one 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. 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] CN 106554828 A discloses a cold flow additive for marine heavy fuel oil selected from vinyl acetate copolymers and / or polymethacrylates.

[0006] 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.

[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 properties of pyrolysis oil or blends containing at least one pyrolysis oil, the method comprising the following steps:

[0010] (i) Providing a pyrolysis oil or a blend comprising at least one 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: hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-vinyl-ether copolymers, and hydrocarbon methacrylate-vinyl-ether copolymers.

[0012] (iii) The at least one polymer provided in step (ii) is added to the pyrolysis oil and / or the blend containing at least one pyrolysis oil provided in step (i), thereby improving the cold flow characteristics of the pyrolysis oil or the blend containing at least one pyrolysis oil.

[0013] The pyrolysis oil formed in step (iii) or a blend containing at least one pyrolysis oil is a product of the method.

[0014] 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 0.5 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 4.3 wt.-% to 71.5 wt.-% (as determined by ASTM D 5134), and further comprising at least one polymer selected from the group consisting of hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-vinyl-ether copolymers, and hydrocarbon-methacrylate-vinyl-ether copolymers.

[0015] These problems are further addressed by using at least one polymer selected from the group consisting of alkyl acrylate-vinyl ether copolymers and alkyl methacrylate-vinyl ether copolymers in the pyrolysis oil or blends containing at least one pyrolysis oil to improve the cold flow characteristics of the pyrolysis oil or blends containing at least one pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste. Detailed Implementation

[0016] 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.

[0017] definition:

[0018] 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.

[0019] "ppm" is defined in this document as "parts per million" mass / volume and corresponds to mg / l.

[0020] "ppmv" is defined in this paper as "parts per million volume" and is dimensionless.

[0021] 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.

[0022] “C1 to C 40 "-alkyl" is defined as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, nonadecanyl, squalyl and higher homologues, as well as their corresponding positional isomers.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] Therefore, the term "plastic waste" includes industrial and household plastic waste, as well as used tires and agricultural and horticultural plastic materials.

[0027] 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.

[0028] 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.

[0029] 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).

[0030] 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). Preferably, water and / or hydrogen are not intentionally added to the feedstock in the pyrolysis reactor.

[0031] 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 devoid of oxygen or air.

[0032] 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 up to 1.3 g / ml at 15°C and 1013 mbar, as determined according to DIN EN ISO 12185, for example, a density in the range of 0.65 to 0.98 g / ml.

[0033] Optionally, prior to step (i) of the method according to the invention, the pyrolysis oil is subjected to one or more methods selected from filtration, centrifugation, adsorption, washing, and extraction. 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.

[0034] 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.

[0035] The pyrolysis oil preferably has a pour point in the range of -30°C to +60°C, more preferably -10°C to +30°C.

[0036] 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 0.5 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 4.3 wt.-% to 71.5 wt.-% (as determined by ASTM D 5134). Such pyrolysis oils are particularly suitable for the methods, pyrolysis oils, and applications according to the present invention.

[0037] More preferably, the pyrolysis oil provided in step (i) has 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 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).

[0038] The pyrolysis oil provided in step (i) can be a single pyrolysis oil manufactured in a single batch or a blend containing at least one pyrolysis oil. The blend may contain pyrolysis oil manufactured in different batches from the same type of plastic waste or pyrolysis oil manufactured in different batches from different types of plastic waste, or at least one pyrolysis oil and at least one additional liquid, wherein the at least one additional liquid is selected from petroleum-based liquids, such as naphtha.

[0039] In step (ii) of the method according to the invention, at least one polymer selected from the group consisting of hydrocarbon-vinyl-ether homopolymer, acrylate-vinyl-ether copolymer and methacrylate-vinyl-ether copolymer is provided.

[0040] In step (iii) of the method according to the invention, at least one polymer provided in step (ii) is added to the pyrolysis oil or blend containing at least one pyrolysis oil provided in step (i). This improves the cold flow properties of the pyrolysis oil or blend containing at least one pyrolysis oil by lowering its pour point.

[0041] The hydrocarbon-vinyl-ether homopolymer is preferably selected from polymers according to Formula 1.

[0042] Formula 1

[0043] Wherein R1 is preferably selected from C1 to C1. 40 -alkyl group, which may optionally be selected from CO, NR1 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR1´R1´´, OR1´, COR1´, COOR1´, CONR1´R1´´ and aryl, wherein R1´ and R1´´ are each independently of each other H or C1- to C4-alkyl.

[0044] Preferably, n is in the range of 2 to 3000, more preferably, n is in the range of 10 to 1500, and most preferably, n is in the range of 25 to 500.

[0045] The preferred polymer having Formula 1 has a number average molecular weight Mn in the range of about 1,000 to 20,000, more preferably about 2,000 to 20,000, and most preferably about 3,000 to 15,000.

[0046] Molecular weight was determined by gel permeation chromatography (GPC) using HDPE (high-density polyethylene) as a molecular weight standard.

[0047] In the definitions of R1´ and R1´´, C1- to C4-alkyl are preferably selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

[0048] In the definition of R1, the aryl group is preferably C6- to C1-. 14 -Aryl, such as phenyl, naphthyl, anthraceneyl and phenanthrene, the aryl group may optionally be substituted by one or more groups selected from C1- to C4-alkyl, OR1´, NR1´R1´´, COOR1´, CONR1´R1´´ and aryl.

[0049] R1 is preferably C1- to C1- 40 -alkyl and more preferably C8- to C10- 24 -alkyl. R1 is branched or straight-chain, more preferably straight-chain. Most preferably, R1 is selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0050] The synthesis of hydrocarbon-vinyl-ether homopolymers (preferably according to Formula 1) is disclosed in EP 1554365 B1 and WO2004 / 035715 A1 and the references cited therein.

[0051] The acrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymer is preferably selected from polymers according to Formula 2.

[0052] Formula 2

[0053] R2 is selected from C1 to C2. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR2 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR2´R2´´, OR2´, COR2´, COOR2´, CONR2´R2´´ and aryl, wherein R2´ and R2´´ are each independently H or C1- to C4-alkyl, and wherein R3 is preferably selected from C1- to C4-alkyl. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from CO, NR3 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR3´R3´´, OR3´, COR3´, COOR3´, CONR3´R3´´ and aryl, wherein R3´ and R3´´ are each independently H or C1- to C4-alkyl, wherein n represents a mole fraction in the range of 0 to 0.6, wherein m represents a mole fraction in the range of 1.0 to 0.4, and R2 and R3 are preferably independently C1- to C4-alkyl. 40 -alkyl and more preferably C8- to C10- 24 -alkyl. R2 and R3 are independently branched or straight-chain, more preferably straight-chain.

[0054] Most preferably, R2 and R3 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eggcosyl, dodecyl, tridecyl, and tetradecyl.

[0055] The methacrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymer is preferably selected from polymers according to Formula 3.

[0056] Formula 3

[0057] R4 is selected from C1 to C1. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR4 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR4´R4´´, OR4´, COR4´, COOR4´, CONR4´R4´´ and aryl, wherein R4´ and R4´´ are each independently H or C1- to C4-alkyl, and wherein R5 is selected from C1- to C4-alkyl. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR5 ´ The O group is interspersed with and / or substituted by one or more groups selected from NR5´R5´´, OR5´, COR5´, COOR5´, CONR5´R5´´ and aryl, wherein R5´ and R5´´ are each independently H or C1- to C4-alkyl, wherein n represents a mole fraction in the range of 0 to 0.6, wherein m represents a mole fraction in the range of 1.0 to 0.4, and R4 and R5 are preferably independently C1- to C4-alkyl. 40 -alkyl and more preferably C8- to C10- 24 -Alkyl group. R4 and R5 are independently branched or linear, more preferably linear.

[0058] Most preferably, R4 and R5 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0059] The synthesis of acrylate hydrocarbon ester-hydrocarbon-vinyl-ether copolymer (preferably according to formula 2) and methacrylate hydrocarbon ester-hydrocarbon-vinyl-ether copolymer (preferably according to formula 3) is described in WO 2004 / 035715 A1 and the references therein.

[0060] In another aspect of the invention, at least one hydrocarbon-vinyl-ether homopolymer (preferably according to Formula 1) (“Polymer 1”) is provided in step (ii), and at least one acrylate hydrocarbon-carbon-vinyl-ether copolymer (preferably according to Formula 2) (“Polymer 2”) and / or at least one methacrylate hydrocarbon-carbon-vinyl-ether copolymer (preferably according to Formula 3) (“Polymer 3”) is provided in step (ii).

[0061] Therefore, the cold flow characteristics of the pyrolysis oil can be improved even further. More preferably, the ratio of "polymer 1" to "polymer 2", "polymer 1" to "polymer 3", and "polymer 1" to "polymer 2" + "polymer 3" is in the range of 1:9 to 9:1, more preferably 2:8 to 8:2.

[0062] At least one polymer provided in step (ii) is added to the pyrolysis oil provided in step (iii) in step (i).

[0063] The at least one polymer can be added to the pyrolysis oil by pouring it into the oil. Preferably, the pyrolysis oil is stirred to ensure that the at least one polymer is evenly distributed within it.

[0064] In the case of a blend containing at least one pyrolysis oil, the at least one polymer provided in step (ii) may be added to the subsequently blended pyrolysis oil or to the final blend containing at least one pyrolysis oil. The at least one polymer may also be added in batches, for example, adding a first portion to a first pyrolysis oil, adding a second portion to a second component of the blend or the final blend, and so on. Therefore, several options for adding the at least one polymer to obtain a blend containing at least one pyrolysis oil and the at least one polymer are available to those skilled in the art.

[0065] Preferably, at least two polymers are provided in step (ii) and added to the pyrolysis oil in step (iii). More preferably, at least one of the at least two polymers is selected from the group consisting of alkyl acrylate-alkyl vinyl ether copolymers and alkyl methacrylate-alkyl vinyl ether copolymers, and at least one of the at least two polymers is selected from alkyl vinyl ether homopolymers. Most preferably, at least one of the at least two polymers is selected from the group consisting of alkyl acrylate-alkyl vinyl ether copolymers according to Formula 2 (wherein R2 and R3 are independently selected from the group consisting of octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl) and the group consisting of alkyl methacrylate-alkyl vinyl ether copolymers according to Formula 3 (wherein R4 and R5 are independently selected from the group consisting of octyl, nonyl, decyl, undecyl, and dodecyl). The polymer is selected from the group consisting of octyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, dodecyl, dodecyl, dodecyl, dodecyl, dodecyl, hexadecyl, heptadecanyl, octadecyl, dodecyl, nonadecanyl, eicosyl, dodec ...

[0066] The concentration of at least one polymer in the pyrolysis oil or blend containing at least one 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 2500 ppmv, more preferably 20 to 2000 ppmv, and most preferably 50 to 1500 ppmv.

[0067] When at least one polymer is added in the form of a solution or dispersion to pyrolysis oil or a blend containing at least one pyrolysis oil, the uniform distribution of at least one polymer in the pyrolysis oil or the blend containing at least one pyrolysis oil can be improved.

[0068] 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.

[0069] 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.

[0070] At least one polymer selected from the group consisting of hydrocarbon-vinyl ether homopolymers, hydrocarbon acrylate-hydrocarbon-vinyl ether copolymers, and hydrocarbon methacrylate-hydrocarbon-vinyl ether copolymers can be used in pyrolysis oils or blends containing at least one pyrolysis oil to improve the cold flow properties of the pyrolysis oil, 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 at least one polymer. This improves the cold flow properties of the pyrolysis oil or blends containing at least one pyrolysis oil.

[0071] Optionally, at least one paraffinic dispersant may be added to the pyrolysis oil or blend containing at least one pyrolysis oil provided in step (i) of the method according to the invention. Preferably, in step (iii), at least one optional paraffinic dispersant may be added to the pyrolysis oil or blend containing at least one pyrolysis oil.

[0072] Optionally, the pyrolysis oil or blend containing at least one pyrolysis oil according to the present invention further comprises at least one paraffinic dispersant.

[0073] Such paraffinic dispersants can be added to prevent wax sedimentation in pyrolysis oil or blends containing at least one pyrolysis oil. Paraffinic dispersants are believed to work by disrupting the formation of wax crystals, reducing their size, and thereby preventing the accumulation of solid wax and further improving the cold flow properties of pyrolysis oil or blends containing at least one pyrolysis oil.

[0074] 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.

[0075] Particularly suitable paraffin dispersants are disclosed in WO 2021 / 126342 A1.

[0076] 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 1000 ppmv, more preferably 20 to 800 ppmv, and most preferably 50 to 600 ppmv.

[0077] 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 as described in any one of embodiments 1 to 3," each embodiment in this series is intended to clearly disclose to a person skilled in the art that the wording of the term should be understood by a person 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.

[0078] 1. A method for improving the cold flow characteristics of pyrolysis oil or a blend containing at least one pyrolysis oil, the method comprising the following steps:

[0079] (i) Providing a pyrolysis oil or a blend comprising at least one pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste.

[0080] (ii) Provides at least one polymer, wherein the at least one polymer is selected from the group consisting of: hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-hydrocarbon-vinyl-ether copolymers, and hydrocarbon methacrylate-hydrocarbon-vinyl-ether copolymers.

[0081] (iii) The at least one polymer provided in step (ii) is added to the pyrolysis oil and / or the blend containing at least one pyrolysis oil provided in step (i), thereby improving the cold flow characteristics of the pyrolysis oil or the blend containing at least one pyrolysis oil.

[0082] 2. The method according to Example 1, wherein at least two polymers are provided in step (ii) and the at least two polymers are added to the pyrolysis oil and / or the blend in step (iii), wherein at least one of the at least two polymers is selected from hydrocarbon acrylate-hydrocarbon-vinyl ether copolymer and hydrocarbon methacrylate-hydrocarbon-vinyl ether copolymer, and wherein at least one of the at least two polymers is selected from hydrocarbon-vinyl ether homopolymer.

[0083] 3. The method according to Example 1 or Example 2, wherein these hydrocarbon-vinyl-ether homopolymers are selected from polymers according to Formula 1.

[0084] Formula 1

[0085] Wherein R1 is preferably selected from C1 to C1. 40 -alkyl group, wherein the alkyl group may optionally be selected from one or more of CO, NR1 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR1´R1´´, OR1´, COR1´, COOR1´, CONR1´R1´´ and aryl groups, wherein R1´ and R1´´ are each independently of each other H or C1- to C4-alkyl, and wherein n is preferably in the range of 2 to 3000, more preferably, n is in the range of 10 to 1500, and most preferably, n is in the range of 25 to 500;

[0086] These acrylate-alkyl-vinyl ether copolymers are selected from polymers according to Formula 2.

[0087] Formula 2

[0088] R2 is selected from C1 to C2. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR2 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR2´R2´´, OR2´, COR2´, COOR2´, CONR2´R2´´ and aryl, wherein R2´ and R2´´ are each independently H or C1- to C4-alkyl, and wherein R3 is preferably selected from C1- to C4-alkyl. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from CO, NR3 ´ The group interspersed with O, and / or substituted by one or more groups selected from NR3´R3´´, OR3´, COR3´, COOR3´, CONR3´R3´´ and aryl, wherein R3´ and R3´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents the mole fraction in the range of 0 to 0.6, and wherein m represents the mole fraction in the range of 1.0 to 0.4;

[0089] Furthermore, these methacrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymers are selected from polymers according to Formula 3.

[0090] Formula 3

[0091] R4 is selected from C1 to C1. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR4 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR4´R4´´, OR4´, COR4´, COOR4´, CONR4´R4´´ and aryl, wherein R4´ and R4´´ are each independently H or C1- to C4-alkyl, and wherein R5 is selected from C1- to C4-alkyl. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR5 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR5´R5´´, OR5´, COR5´, COOR5´, CONR5´R5´´ and aryl, wherein R5´ and R5´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents a mole fraction in the range of 0 to 0.6, and wherein m represents a mole fraction in the range of 1.0 to 0.4.

[0092] 4. The method according to any one of Examples 1 to 3, wherein R1 is selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0093] 5. The method according to any one of Examples 1 to 4, wherein R2, R3, R4 and R5 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0094] 6. The method according to any one of Examples 1 to 5, wherein R1, R2, R3, R4 and R6 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0095] 7. The method according to any one of Examples 1 to 6, wherein the concentration of the at least one polymer in the pyrolysis oil and / or the blend is preferably in the range of 10 to 1000 ppmv, more preferably 20 to 800 ppmv, and most preferably 50 to 600 ppmv.

[0096] 8. The method according to any one of Examples 1 to 7, 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 0.5 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 4.3 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 ENISO 2719) and / or at a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

[0097] 9. The method according to any one of Examples 1 to 8, wherein the pyrolysis oil is produced by pyrolysis of mixed plastic waste.

[0098] 10. The method according to any one of Examples 1 to 9, wherein the pyrolysis oil and / or the blend containing at least one 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.

[0099] 11. The method according to Example 10, wherein the concentration of the at least one paraffinic dispersant in the pyrolysis oil and / or the blend is in the range of 10 to 2500 ppmv, more preferably 20 to 2000 ppmv, and most preferably 50 to 1500 ppmv.

[0100] 12. The method according to any one of Examples 1 to 11, comprising the following steps:

[0101] - The pyrolysis oil having improved cold flow characteristics, or the blend containing at least one pyrolysis oil having improved cold flow characteristics, which is available or obtainable by any one of Examples 1 to 12, or the chemical material available or obtainable by any one of Examples 1 to 12, is converted to obtain product PRF1.

[0102] 13. The method according to Example 12, wherein the product PRF1 is selected from:

[0103] i) Building blocks or single units; or

[0104] ii) a polymer, preferably polymer A, a polymer composition, preferably polymer composition A, or a polymer product, preferably polymer product A; or

[0105] iii) Cleaning polymers, cleaning surfactants, descaling compounds, cleaning biocides, or combinations thereof; or

[0106] iv) Agricultural chemical compositions, agricultural chemical formulations, adjuvants, or agricultural chemical active ingredients; or

[0107] v) Active pharmaceutical ingredients or intermediates thereof, pharmaceutical excipients, animal feed additives, human food additives, dietary supplements, aromatic chemicals or aromatic compositions; or

[0108] vi) Aqueous polymer dispersions, preferably polyurethane or polyurethane-poly(meth)acrylate mixed 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

[0109] vii) Cosmetic surfactants, emollients, waxes, cosmetic polymers, UV filters, other cosmetic ingredients, or combinations thereof or formulations thereof; or

[0110] viii) Polymer B, polymer composition B, coating composition, other functional composition, foil, molded body, coating or coated substrate.

[0111] 14. 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 0.5 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 4.3 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 C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

[0112] It further comprises at least one polymer selected from the group consisting of hydrocarbon-vinyl-ether homopolymers, acrylate-carbonyl-vinyl-ether copolymers, and methacrylate-carbonyl-vinyl-ether copolymers.

[0113] 15. The pyrolysis oil according to Example 14, wherein these hydrocarbon-vinyl-ether homopolymers are selected from polymers according to Formula 1.

[0114] Formula 1

[0115] Wherein R1 is preferably selected from C1 to C1. 40 -alkyl group, wherein the alkyl group may optionally be selected from one or more of CO, NR1 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR1´R1´´, OR1´, COR1´, COOR1´, CONR1´R1´´ and aryl groups, wherein R1´ and R1´´ are each independently of each other H or C1- to C4-alkyl, and wherein n is preferably in the range of 2 to 3000, more preferably, n is in the range of 10 to 1500, and most preferably, n is in the range of 25 to 500;

[0116] These acrylate-alkyl-vinyl ether copolymers are selected from polymers according to Formula 2.

[0117] Formula 2

[0118] R2 is selected from C1 to C2. 40 -alkyl, more preferably selected from C8- to C124 -alkyl group, which may optionally be selected from one or more of CO, NR2 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR2´R2´´, OR2´, COR2´, COOR2´, CONR2´R2´´ and aryl, wherein R2´ and R2´´ are each independently H or C1- to C4-alkyl, and wherein R3 is preferably selected from C1- to C4-alkyl. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR3 ´ The group interspersed with O, and / or substituted by one or more groups selected from NR3´R3´´, OR3´, COR3´, COOR3´, CONR3´R3´´ and aryl, wherein R3´ and R3´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents the mole fraction in the range of 0 to 0.6, and wherein m represents the mole fraction in the range of 1.0 to 0.4;

[0119] Furthermore, these methacrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymers are selected from polymers according to Formula 3.

[0120] Formula 3

[0121] R4 is selected from C1 to C1. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR4 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR4´R4´´, OR4´, COR4´, COOR4´, CONR4´R4´´ and aryl, wherein R4´ and R4´´ are each independently H or C1- to C4-alkyl, and wherein R5 is selected from C1- to C4-alkyl. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR5 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR5´R5´´, OR5´, COR5´, COOR5´, CONR5´R5´´ and aryl, wherein R5´ and R5´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents a mole fraction in the range of 0 to 0.6, and wherein m represents a mole fraction in the range of 1.0 to 0.4.

[0122] 16. The pyrolysis oil according to Example 15, wherein R1, R2, R3, R4 and R5 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0123] 17. The pyrolysis oil according to Example 15, wherein the acrylate hydrocarbon ester-hydrocarbon-vinyl-ether copolymers and / or methacrylate hydrocarbon ester-hydrocarbon-vinyl-ether copolymers are selected from polymers according to Formula 2 and / or 3, wherein R2, R3, R4 and R5 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0124] 18. The pyrolysis oil according to Example 15, wherein the hydrocarbon-vinyl-ether homopolymers are selected from polymers according to Formula 1, and wherein R1 is selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0125] 19. The pyrolysis oil according to any one of Examples 15 to 18, wherein at least two polymers are provided in step (ii) and the at least two polymers are added to the pyrolysis oil in step (iii), wherein at least one of the at least two polymers is selected from hydrocarbon acrylate-hydrocarbon-vinyl ether copolymers and hydrocarbon methacrylate-hydrocarbon-vinyl ether copolymers, and wherein at least one of the at least two polymers is selected from hydrocarbon-vinyl ether homopolymers.

[0126] 20. The pyrolysis oil according to any one of Examples 15 to 19, wherein the concentration of at least one polymer selected from the group consisting of hydrocarbon-vinyl-ether homopolymer, hydrocarbon acrylate-hydrocarbon-vinyl-ether copolymer and hydrocarbon methacrylate-hydrocarbon-vinyl-ether copolymer is in the range of 10 to 2500 ppmv, more preferably 20 to 2000 ppmv and most preferably 50 to 1500 ppmv.

[0127] 21. The pyrolysis oil according to any one of Examples 15 to 20, 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.

[0128] 22. The pyrolysis oil according to Example 21, 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.

[0129] 23. Use of at least one polymer selected from the group consisting of hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-hydrocarbon-vinyl-ether copolymers, and hydrocarbon methacrylate-hydrocarbon-vinyl-ether copolymers in pyrolysis oil or blends containing at least one pyrolysis oil for improving the cold flow properties of pyrolysis oil and / or blends containing at least one pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste.

[0130] 24. The use according to Example 23, wherein at least two polymers are added to the pyrolysis oil and / or a blend containing at least one pyrolysis oil, and wherein at least one of the at least two polymers is selected from hydrocarbon acrylate-hydrocarbon-vinyl ether copolymer and hydrocarbon methacrylate-hydrocarbon-vinyl ether copolymer, and wherein at least one of the at least two polymers is selected from hydrocarbon-vinyl ether homopolymer.

[0131] 25. The use according to Example 23 or 24, wherein these hydrocarbon-vinyl-ether homopolymers are selected from polymers according to Formula 1.

[0132] Formula 1

[0133] Wherein R1 is preferably selected from C1 to C1. 40 -alkyl group, which may optionally be selected from CO, NR1 ´ The O group is interspersed with and / or substituted by one or more groups selected from NR1´R1´´, OR1´, COR1´, COOR1´, CONR1´R1´´ and aryl groups, wherein R1´ and R1´´ are each independently H or C1- to C4-alkyl, and

[0134] Wherein n is preferably in the range of 2 to 3000, more preferably in the range of 10 to 1500, and most preferably in the range of 25 to 500;

[0135] These acrylate-alkyl-vinyl ether copolymers are selected from polymers according to Formula 2.

[0136] Formula 2

[0137] R2 is selected from C1 to C2. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR2 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR2´R2´´, OR2´, COR2´, COOR2´, CONR2´R2´´ and aryl, wherein R2´ and R2´´ are each independently H or C1- to C4-alkyl, and wherein R3 is preferably selected from C1- to C4-alkyl. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR3 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR3´R3´´, OR3´, COR3´, COOR3´, CONR3´R3´´ and aryl, wherein R3´ and R3´´ are each independently H or C1- to C4-alkyl.

[0138] Where n represents the mole fraction in the range of 0 to 0.6,

[0139] Where m represents the mole fraction in the range of 1.0 to 0.4;

[0140] Furthermore, these methacrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymers are selected from polymers according to Formula 3.

[0141] Formula 3

[0142] R4 is selected from C1 to C1. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR4 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR4´R4´´, OR4´, COR4´, COOR4´, CONR4´R4´´ and aryl, wherein R4´ and R4´´ are each independently H or C1- to C4-alkyl, and wherein R5 is selected from C1- to C4-alkyl. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR5 ´The O group is interspersed with other groups and / or substituted by one or more groups selected from NR5´R5´´, OR5´, COR5´, COOR5´, CONR5´R5´´ and aryl groups, wherein R5´ and R5´´ are each independently H or C1- to C4-alkyl.

[0143] Where n represents the mole fraction in the range of 0 to 0.6,

[0144] Where m represents the mole fraction in the range of 1.0 to 0.4.

[0145] 26. The use according to any one of Examples 25, wherein R1 is selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eggcosyl, dodecyl, tridecyl, and tetradecyl.

[0146] 27. The use according to any one of Examples 25, wherein R2, R3, R4 and R5 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0147] 28. The use according to any one of Examples 25, wherein R1, R2, R3, R4 and R6 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

[0148] 29. The use according to any one of Examples 23 to 28, wherein the concentration of the at least one polymer in the pyrolysis oil and / or blend containing at least one pyrolysis oil is preferably in the range of 10 to 2500 ppmv, more preferably 20 to 2000 ppmv and most preferably 50 to 1500 ppmv.

[0149] 30. The use according to any one of Examples 23 to 29, 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 0.5 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 4.3 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 ENISO 2719) and / or at a C11 to C21 content in the range of 5 wt.-% to 70 wt.-% (measured according to ASTM D 5134).

[0150] 31. The use according to any one of Examples 23 to 30, wherein the pyrolysis oil is produced by pyrolysis of mixed plastic waste.

[0151] 32. The use according to any one of Examples 23 to 31, wherein the pyrolysis oil is a blend comprising at least one pyrolysis oil.

[0152] 33. The use according to any one of Examples 23 to 32, wherein the pyrolysis oil and / or the blend comprising at least one 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.

[0153] 34. The use according to Example 33, wherein the concentration of the at least one paraffinic dispersant in the pyrolysis oil and / or blend is in the range of 10 to 1000 ppmv, more preferably 20 to 800 ppmv, and most preferably 50 to 600 ppmv.

[0154] The present invention further relates to a method according to any one of Examples 1 to 13, wherein the content of the pyrolysis oil having improved cold flow characteristics or the blend containing at least one pyrolysis oil having improved cold flow characteristics 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 the blend containing at least one pyrolysis oil having improved cold flow characteristics 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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 mixed dispersions, one or more polyurethanes (including UV-curable polyurethanes), and one or more polyurethane-poly(meth)acrylate mixed 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 mixed polymers are defined in more detail in the section of reference RF1

[6016] . 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.

[0166] 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.

[0167] 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] .

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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.

[0172] The present invention will be further explained through the following non-limiting examples. Example

[0173] Before and after the addition of the polymer according to the invention or the polymer disclosed in the prior art, the pour points of pyrolysis oil (“pyrolysis oil 1”) and a blend (“pyrolysis oil blend 1”) containing two pyrolysis oils (“pyrolysis oil 2” and “pyrolysis oil 3”) were measured using a pour point analyzer MPP 5GS from ISL Corporation according to the method of ASTM D7346-15.

[0174] When provided in step (i), pyrolysis oil 1 has a pour point of 3°C. Two different single polymers and a mixture of two different polymers are added to pyrolysis oil 1 at different concentrations, and the pour point of the pyrolysis oil containing the polymers according to the invention is measured again.

[0175] Polymer 1: A hydrocarbon-vinyl-ether homopolymer according to Formula 1, wherein R1 = C18 alkyl

[0176] Polymer 2: An acrylate-alkyl-vinyl ether copolymer according to Formula 2, wherein R2 = C18 alkyl and R3 = C12 alkyl.

[0177] Polymer 12: A mixture of polymer 1 (30 wt.-%) and polymer 2 (70 wt.-%)

[0178] Polymer c: Polymer used for comparative examples, alkyl acrylate-ethylene-vinyl ester copolymer (disclosed in WO 2022 / 056212 A1).

[0179] The results of pyrolysis oil 1 are summarized in Table 1:

[0180]

[0181] Compared to polymer c disclosed in WO 2022 / 056212 A1, polymers 1, 2, and 12 cause a greater decrease in the initial pour point of pyrolysis oil 1. Therefore, the cold flow characteristics of pyrolysis oil 1 are further improved when the polymers or mixtures of polymers according to the invention are added, compared to polymers known from the prior art.

[0182] When provided in step (i), the pyrolysis oil blend 1 has a pour point of 9°C and consists of about 50 wt.-% pyrolysis oil 2 and about 50 wt.-% pyrolysis oil 3. The same type of polymer added to pyrolysis oil 1 is also added to pyrolysis oil blend 1.

[0183] The results for pyrolysis oil blend 1 are summarized in Table 2:

[0184]

[0185] Compared to polymer c disclosed in WO 2022 / 056212 A1, polymers 1, 2, and 12 cause a greater decrease in the initial pour point of pyrolysis oil blend 1. Therefore, compared to polymers known from the prior art, the cold flow properties of pyrolysis oil blend 1 are further improved when the polymers or mixtures of polymers according to the invention are added.

Claims

1. A method for improving the cold flow characteristics of pyrolysis oil or a blend containing at least one pyrolysis oil, the method comprising the following steps: (i) Providing a pyrolysis oil or a blend comprising at least one pyrolysis oil, wherein the pyrolysis oil is produced by the pyrolysis of plastic waste. (ii) Provides at least one polymer, wherein the at least one polymer is selected from the group consisting of: hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-hydrocarbon-vinyl-ether copolymers, and hydrocarbon methacrylate-hydrocarbon-vinyl-ether copolymers. (iii) The at least one polymer provided in step (ii) is added to the pyrolysis oil and / or the blend containing at least one pyrolysis oil provided in step (i), thereby improving the cold flow characteristics of the pyrolysis oil or the blend containing at least one pyrolysis oil.

2. The method according to claim 1, wherein, In step (ii), at least two polymers are provided and in step (iii), the at least two polymers are added to the pyrolysis oil and / or the blend, wherein at least one of the at least two polymers is selected from alkyl acrylate-alkyl vinyl ether copolymer and alkyl methacrylate-alkyl vinyl ether copolymer, and wherein at least one of the at least two polymers is selected from alkyl vinyl ether homopolymer.

3. The method according to claim 1 or claim 2, wherein, These hydrocarbon-vinyl-ether homopolymers are selected from polymers according to Formula 1. Formula 1 Wherein R1 is preferably selected from C1 to C1. 40 -alkyl group, which may optionally be selected from CO, NR1 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR1´R1´´, OR1´, COR1´, COOR1´, CONR1´R1´´ and aryl, wherein R1´ and R1´´ are each independently of each other H or C1- to C4-alkyl, and wherein n is preferably in the range of 2 to 3000; These acrylate-alkyl-vinyl ether copolymers are selected from polymers according to Formula 2. Formula 2 R2 is selected from C1 to C2. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR2 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR2´R2´´, OR2´, COR2´, COOR2´, CONR2´R2´´ and aryl, wherein R2´ and R2´´ are each independently H or C1- to C4-alkyl, and wherein R3 is preferably selected from C1- to C4-alkyl. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR3 ´ The group interspersed with O, and / or substituted by one or more groups selected from NR3´R3´´, OR3´, COR3´, COOR3´, CONR3´R3´´ and aryl, wherein R3´ and R3´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents the mole fraction in the range of 0 to 0.6, and wherein m represents the mole fraction in the range of 1.0 to 0.4; Furthermore, these methacrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymers are selected from polymers according to Formula 3. Formula 3 R4 is selected from C1 to C1. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR4 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR4´R4´´, OR4´, COR4´, COOR4´, CONR4´R4´´ and aryl, wherein R4´ and R4´´ are each independently H or C1- to C4-alkyl, and wherein R5 is selected from C1- to C4-alkyl. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR5 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR5´R5´´, OR5´, COR5´, COOR5´, CONR5´R5´´ and aryl, wherein R5´ and R5´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents a mole fraction in the range of 0 to 0.6, and wherein m represents a mole fraction in the range of 1.0 to 0.

4.

4. The method according to claim 3, wherein, R1, R2, R3, R4 and R5 are independently selected from the group consisting of: octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl.

5. The method according to any one of claims 1 to 4, wherein, The concentration of the at least one polymer in the pyrolysis oil and / or the blend is in the range of 10 to 2500 ppmv.

6. The method according to any one of claims 1 to 5, 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 D 5134) and / or a naphthalene content of 0.5 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 4.3 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 according to 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).

7. The method according to any one of claims 1 to 6, wherein, The pyrolysis oil is produced by pyrolysis of mixed plastic waste.

8. The method according to any one of claims 1 to 7, wherein, Add at least one paraffinic dispersant to the pyrolysis oil and / or the blend containing at least one 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 the at least one paraffinic dispersant in the pyrolysis oil and / or the blend is in the range of 10 to 1000 ppmv.

10. The method according to any one of claims 1 to 19, comprising the following steps: - The pyrolysis oil having improved cold flow characteristics, which is obtainable by any one of claims 1 to 10, or the blend containing at least one pyrolysis oil having improved cold flow characteristics, is converted to obtain product PRF1.

11. The method according to claim 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 0.5 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 4.3 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 hydrocarbon-vinyl-ether homopolymers, hydrocarbon acrylate-hydrocarbon-vinyl-ether copolymers and hydrocarbon methacrylate-hydrocarbon-vinyl-ether copolymers.

13. The pyrolysis oil according to claim 12, wherein, In step (ii), at least two polymers are provided and in step (iii), the at least two polymers are added to the pyrolysis oil, wherein at least one of the at least two polymers is selected from alkyl acrylate-alkyl vinyl ether copolymer and alkyl methacrylate-alkyl vinyl ether copolymer, and wherein at least one of the at least two polymers is selected from alkyl vinyl ether homopolymer.

14. The pyrolysis oil according to claim 12 or 13, wherein, The concentration of at least one polymer selected from the group consisting of hydrocarbon-vinyl-ether homopolymer, acrylate-carbonyl-vinyl-ether copolymer, and methacrylate-carbonyl-vinyl-ether copolymer in the pyrolysis oil is in the range of 10 to 2500 ppmv.

15. The pyrolysis oil according to any one of claims 12 to 14, wherein, These hydrocarbon-vinyl-ether homopolymers are selected from polymers according to Formula 1. Formula 1 Wherein R1 is preferably selected from C1 to C1. 40 -alkyl group, which may optionally be selected from CO, NR1 ´ The O group is interspersed with and / or substituted by one or more groups selected from NR1´R1´´, OR1´, COR1´, COOR1´, CONR1´R1´´ and aryl groups, wherein R1´ and R1´´ are each independently H or C1- to C4-alkyl, and Wherein n is preferably in the range of 2 to 3000, more preferably in the range of 10 to 1500, and most preferably in the range of 25 to 500; These acrylate-alkyl-vinyl ether copolymers are selected from polymers according to Formula 2. Formula 2 R2 is selected from C1 to C2. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR2 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR2´R2´´, OR2´, COR2´, COOR2´, CONR2´R2´´ and aryl, wherein R2´ and R2´´ are each independently H or C1- to C4-alkyl, and wherein R3 is preferably selected from C1- to C4-alkyl. 40 -alkyl, more preferably selected from C8- to C1 24 -alkyl group, which may optionally be selected from one or more of CO, NR3 ´ The group interspersed with O, and / or substituted by one or more groups selected from NR3´R3´´, OR3´, COR3´, COOR3´, CONR3´R3´´ and aryl, wherein R3´ and R3´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents the mole fraction in the range of 0 to 0.6, and wherein m represents the mole fraction in the range of 1.0 to 0.4; Furthermore, these methacrylate hydrocarbon ester-hydrocarbon-vinyl ether copolymers are selected from polymers according to Formula 3. Formula 3 R4 is selected from C1 to C1. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR4 ´ The group interspersed with O is, and / or substituted by one or more groups selected from NR4´R4´´, OR4´, COR4´, COOR4´, CONR4´R4´´ and aryl, wherein R4´ and R4´´ are each independently H or C1- to C4-alkyl, and wherein R5 is selected from C1- to C4-alkyl. 40 -alkyl group, more preferably selected from C8- to C9- 24 -alkyl group, which may optionally be selected from CO, NR5 ´ The groups interspersed with O are, and / or substituted by one or more groups selected from NR5´R5´´, OR5´, COR5´, COOR5´, CONR5´R5´´ and aryl, wherein R5´ and R5´´ are each independently of each other H or C1- to C4-alkyl, wherein n represents a mole fraction in the range of 0 to 0.6, and wherein m represents a mole fraction in the range of 1.0 to 0.4.

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