Closed loop recycling concept for composites comprising covalently adaptive poly (urea-urethane) networks with dynamically hindered urea bonds

Abstract

The present invention relates to a process for recycling a composition comprising a poly (urea-urethane) polymer having hindered urea bonds, the process comprising treating the composition comprising a poly (urea-urethane) polymer under conditions suitable for at least partially cleaving the urea bonds of the polymer to obtain a mixture (M1) comprising a prepolymer. The invention also relates to prepolymers obtained or obtainable according to the method, to poly (urea-urethane) polymers obtained or obtainable according to the method according to the invention, and to the use of said prepolymers for producing poly (urea-urethane) polymers.

Description

[0001] The present invention relates to a method for recycling a composition comprising a poly(urea - urethane) polymer having blocked urea bonds, the method comprising treating the composition comprising the poly(urea - urethane) polymer under conditions suitable for at least partially cleaving the urea bonds of the polymer to obtain a mixture (M1) containing a prepolymer.

[0002] In materials and polymer science, there is a need to develop polymer materials having desired in - use performance characteristics that are also ductile, repairable, and shape - reprogrammable. There is also a need to develop such polymers that can be degraded or depolymerized reversibly. Although shape - memory and self - healing polymers are known, many of these polymers do not have both the desired performance and dynamic characteristics. With regard to degradable or reversibly depolymerizable polymers, these polymers typically lack the required in - use performance characteristics and are either too prone to degradation or, on the other hand, do not degrade as readily or rapidly as desired.

[0003] In addition, polymer - based composites containing fillers (such as fibrous materials or isotropic materials), for example glass - fiber - reinforced plastics (GFRP), are widely used in applications such as aircraft, boats, or windmill blades. More than 10 million tons of GFRP are produced annually, and once embedded in the polymer, there is no viable recycling concept.

[0004] Due to their excellent dimensional stability, chemical resistance, and thermal and mechanical properties, thermosetting plastics are used in a wide range of applications, including structural composites, adhesives, coatings, and electrical insulation. However, due to their inability to melt or flow at high temperatures, conventional thermosetting plastics cannot be reshaped, reprocessed, or recycled.

[0005] An effective chemical strategy for combining these properties is to introduce dynamic chemical bonds into the polymer network, resulting in a dynamic polymer network. Polymers containing dynamic bonds are considered covalent adaptable networks (CAN).

[0006] Several scientific publications disclose that urea bonds carrying bulky groups on the nitrogen atom give rise to blocked urea bonds (HUB) that are dynamic and can reversibly dissociate into amines and isocyanates based on an associative exchange mechanism. However, those documents do not disclose methods suitable for large - scale industrial processes that would allow the recycling of waste materials on a large scale.

[0007] Therefore, there is a need to develop processing techniques for recycling materials from plastic waste. The recycling method should reduce both material waste and the carbon footprint. In addition, it should be an economical and energy-efficient method that provides valuable materials with high-tech characteristics. In contrast, disposal (e.g., by combustion) has a negative impact on the environment and on the carbon footprint. In addition, there is a need to provide new polymers and methods for recycling said polymers.

[0008] According to the present invention, this object is solved by a method for recycling a composition comprising a poly(ureaurethane) polymer (PUU1), the method comprising step (i):

[0009] (i) treating the composition comprising the poly(ureaurethane) polymer (PUU1) under conditions suitable for at least partially cleaving the urethane bonds of the polymer to obtain a mixture (M1) containing a prepolymer,

[0010] The poly(ureaurethane) polymer (PUU1) is obtainable or obtained by a method comprising:

[0011] - reacting the following components:

[0012] (i) at least one isocyanate;

[0013] (ii) at least one polyol; and

[0014] (iii) at least one secondary amine having the following formula (I):

[0015]

[0016] where -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 - —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; where

[0017] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0018] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0019] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0020] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0021] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0022] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0023] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0024] -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene;

[0025] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0026] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene;

[0027] -Z 11 - is a C6-C 30 arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 10 alkyl;

[0028] -Z 12 - is -N(R f )-;

[0029] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where at least one of one or more heteroatoms of Z 13 is from X a ;

[0030] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0031] wherein X a is an O atom or NH and X b is an O atom or NH, wherein X a and X b at least one of which is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0032] wherein

[0033] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl,

[0034] R b and R e are each independently as defined for R c , R d , R f and R g ; or

[0035] there is no R b and Re and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a and C b , X a , X b and R a ; or

[0036] (B) C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and

[0037] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both; or

[0038] (C) -C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; or

[0039] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both;

[0040] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are independently of each other as R c , R d , R f and R g defined in any one of (A);

[0041] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are independently of each other as R c , Rd , R f and R g as defined by any one of.

[0042] According to the present invention, a composition comprising a poly(urea - urethane) polymer (PUU1) is treated under conditions suitable for at least partially cleaving the urea bonds. Preferably, under the treatment conditions, the urea bonds in the polymer are cleaved while the urethane bonds are stable. Preferably, the treatment is carried out under conditions suitable for causing cleavage of the urea bonds in the polymer until the material is processable, soluble or has a reduced viscosity for the desired application. According to the present invention, in step (i), a mixture (M1) is obtained which contains a prepolymer but may also obtain a poly(urea - urethane) polymer and additional components.

[0043] According to a further embodiment, the present invention also relates to a method as disclosed above, wherein the conditions applied in step (i) are suitable for cleaving the urea bonds of the polymer while the urethane bonds are substantially stable.

[0044] In the context of the present invention, the bond between the N of the urea group (from a secondary hindered amine) which can be reversibly formed and broken and the C of (NCO) is also designated as a reversible NCO bond.

[0045] The method of the present invention enables the reuse of poly(urea - urethane) polymers. The method of the present invention offers the advantages that a wide range of mild reaction conditions can be applied and allows the recovery and reuse of the components used. Preferably, the method of the present invention allows the complete recovery of the poly(urea - urethane) and expensive fillers, such as carbon fibers, used from the composite material. Surprisingly, it has been found that the polymers according to the present invention allow the production of composite materials that can be used in many applications while being easily repairable and recyclable. In fact, the poly(urea - urethane) polymers according to the present invention have dynamic hindered urea bonds (HUBs) which act as dynamic covalent bonds in covalent adaptable systems / networks (CAS / CANs). Therefore, it is considered that introducing bulky substituents to the nitrogen atom weakens the bond, such that there is a dissociation equilibrium between open bonds and closed bonds, and this dissociation equilibrium shifts to the open side by increasing the temperature. The HUBs split into the original constituent groups (depolymerization). The claimed materials are easily processable by thermomechanical processing methods as shown below and are conducive to the chemical and mechanical recycling of poly(urea - urethane) polymers.

[0046] According to the present invention, the treatment according to step (i) can be applied to a shaped body or also to parts of a shaped body. The composition may, for example, be cut into small pieces before treatment or also be ground using standard procedures.

[0047] The treatment may include treatment at an elevated temperature (e.g., in the range of 60 °C to 200 °C).

[0048] For example, the treatment may include applying pressure at an elevated temperature, such as a pressure in the range of 1 bar to 200 bar in a solution or melt process, or by applying mechanical energy in an extrusion process or in a hot press.

[0049] For example, the treatment may include applying reduced pressure at an elevated temperature, such as in a solution or melt process, preferably between 50 mbar and 1 bar.

[0050] Thus, according to a further embodiment, the invention also relates to a method as disclosed above, wherein step (i) is a treatment at a temperature in the range of 60 °C to 200 °C and at a pressure in the range of 1 bar to 200 bar or in the range of 50 mbar to 1 bar.

[0051] Preferably, in solution, the treatment is carried out at a pressure in the range of 1 to 180 bar, preferably in the range of 1 to 150 bar, more preferably in the range of 1 to 100 bar.

[0052] Preferably, in the melt, the treatment is carried out at a pressure in the range of 1.5 to 180 bar, preferably in the range of 2 to 150 bar, more preferably in the range of 5 to 100 bar.

[0053] Preferably, the mechanical pressing is hot pressing, more preferably at a temperature in the range of 80 °C to 200 °C, more preferably in the range of 120 °C to 160 °C, more preferably in the range of 130 °C to 150 °C.

[0054] Preferably, the mechanical pressing is carried out at a pressure in the range of 1.5 to 180 bar, preferably in the range of 2 to 100 bar, more preferably in the range of 5 to 50 bar.

[0055] Preferably, the mechanical pressing is carried out for a duration in the range of 1 to 60 min, more preferably in the range of 4 to 20 min, more preferably in the range of 5 to 10 min.

[0056] Preferably, the extrusion is carried out at a temperature in the range of 140 °C to 220 °C, more preferably in the range of 160 °C to 200 °C, more preferably in the range of 170 °C to 190 °C.

[0057] Preferably, the extrusion is carried out at a torque in the range of 2.0 to 2.4 kN, more preferably at a maximum torque of 2.2 kN.

[0058] According to the present invention, step (i) may be carried out using a suitable solvent. Suitable solvents are known in principle and include, for example, aprotic solvents, in particular organic aprotic solvents.

[0059] According to a further embodiment, the present invention also relates to a method as disclosed above, wherein an aprotic solvent is added in step (i).

[0060] In principle, any solvent that is suitable for dissolving the poly(urea - urethane) polymer or the mixture containing the obtained prepolymer but will not react with the poly(urea - urethane) polymer or the components can be used. For an economical method, an organic solvent having a boiling point below 230 °C, preferably below 150 °C, at ambient pressure is preferably selected.

[0061] In one embodiment, the organic aprotic solvent is selected from aliphatic hydrocarbons, halogenated hydrocarbons, ethers, aromatic hydrocarbons, esters, amides, sulfoxides and sulfones, ketones and mixtures thereof.

[0062] Accordingly, according to a further embodiment, the present invention also relates to a method as disclosed above, wherein the organic aprotic solvent is selected from aliphatic hydrocarbons, halogenated hydrocarbons, ethers, aromatic hydrocarbons, esters, amides, sulfoxides, sulfones, ketones and mixtures thereof.

[0063] Suitable aliphatic hydrocarbons are selected from pentane and its isomers, hexane and its isomers, heptane and its isomers, octane and its isomers, cyclopentane, methyl - cyclopentane, cyclohexane and methylcyclohexane and mixtures thereof.

[0064] Suitable halogenated hydrocarbons are selected from dichloromethane, chloroform, 1,2 - dichloroethane, 1,1,1 - trichloroethane, 1,1,2,2 - tetrachloroethane and mixtures thereof.

[0065] Suitable ethers are selected from tetrahydrofuran, 1,4 - dioxane, anisole, diethyl ether, isopropyl ether, butyl ether, methyl tert - butyl ether (MTBE) and diethylene glycol dimethyl ether and mixtures thereof.

[0066] Suitable aromatic hydrocarbons are selected from benzene, toluene, o - xylene, m - xylene, p - xylene, ethylbenzene, mesitylene and chlorobenzene, isomers of dichlorobenzene and mixtures thereof.

[0067] Suitable esters are selected from γ - butyrolactone, methyl formate, methyl acetate, ethyl acetate and butyl acetate and mixtures thereof.

[0068] Suitable amides are selected from dimethylformamide, dimethylacetamide, diethylformamide, diethylacetamide and mixtures thereof.

[0069] Suitable sulfoxides and sulfones are selected from dimethyl sulfoxide and sulfolane and mixtures thereof.

[0070] Suitable ketones are selected from acetone, methyl ethyl ketone, diethyl ketone, cyclopentanone and mixtures thereof.

[0071] 1,3-Dimethyl-2-imidazolidinone (DMI) can also be suitable in the context of the present invention.

[0072] If desired, mixtures of two or more of the aforementioned organic aprotic solvents can be used.

[0073] In a preferred embodiment, the extraction solvent is selected from THF, MTBE, toluene, xylene, DMSO, DMI and mixtures thereof.

[0074] According to step (i), the urea bonds of the poly(ureaurethane) polymer are cleaved. In principle, according to the present invention, the method is reversible and the urea bonds can reform, for example, when the temperature of the obtained mixture decreases. This allows, for example, the reshaping of shaped bodies or also the repair of shaped bodies.

[0075] According to a further embodiment, additional components can also be added which react with the free functional groups formed due to the dynamic cleavage of the urea bonds. This allows, for example, the formation of stable components which can be isolated.

[0076] Thus, according to a further embodiment, the present invention also relates to a method as disclosed above, wherein in step (i), a component (S) suitable for reacting with the free functional groups of the cleaved urea bonds is added.

[0077] In the context of the present invention, component (S) can also be designated as a scavenger.

[0078] Suitable as component (S) are compounds which form stable bonds with the components in the mixture (M1). Suitable are, for example, compounds having OH or NH groups, such as polyols, diols, monols, polyamines, oligamines, diamines and monoamines, which can react with free isocyanate groups. In addition, isocyanates such as polyisocyanates or diisocyanates can be added as component (S), which can react with the free functional groups of the hindered amines present in the mixture (M1).

[0079] Suitable amines as component (S) can be amines of the general formula (II):

[0080]

[0081] wherein the residues are defined as defined above, and the condition is that Xa is NH and there is no Xb, Cb, Rb, Rc and Rd, or Xb is NH and there is no Xa, Ca, Re, Rf and Rg.

[0082] Accordingly, according to a further embodiment, the invention also relates to the method as disclosed above, wherein the component (S) is selected from the group consisting of: polyols, diols, polyisocyanates, diisocyanates, polyamines, oligoamines, diamines and amines of the general formula (II).

[0083] Suitable polyols are known per se to the person skilled in the art.

[0084] In principle, any polyol conventionally used for the preparation of polyurethanes can be used as the polyol. The type of polyol can depend on the desired application purpose. Suitable polyols are polyester polyols, in particular including aliphatic polyester polyols and aliphatic-aromatic polyester polyols, polyester carbonate polyols, polyether ester polyols, aliphatic polycarbonate polyols, polyacrylate polyols, polyolefin polyols, aliphatic polyether alcohols and mixtures thereof. In a preferred group of embodiments, the at least one polyol is selected from polyester polyols, in particular aliphatic polyester polyols and aliphatic-aromatic polyester polyols, aliphatic polycarbonate polyols, aliphatic polyether alcohols and mixtures thereof. In particular, the at least one polyol comprises a polyester polyol and / or an aliphatic polyether polyol as described herein. In particular, the at least one polyol is selected from polyester polyols, aliphatic polyether polyols and combinations thereof.

[0085] Diols and diamines are in principle known to the person skilled in the art. Suitable are, for example, aliphatic diols such as butanediol, pentanediol, hexanediol or decanediol and the corresponding isomers, preferably pentanediol and / or hexanediol, in particular hexanediol. In addition to these alcohols, further monoalcohols, diols or polyols may also be present in the alcohol component, for example those having a molecular weight of 62 to 400 g / mol. Examples are monoethylene glycol, 1,2- or 1,3-propanediol, 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, PTHF 250, mixtures of bisphenols and polyols.Suitable active hydrogen compounds can be, for example, 1,2-, 1,3- and 1,4-butanediol, butane-2,3-diol, pentane-1,2-diol, pentane-1,3-diol, pentane-1,4-diol, pentane-1,5-diol, pentane-2,3-diol, pentane-2,4-diol, hexane-1,2-diol, hexane-1,3-diol, hexane-1,4-diol, hexane-1,5-diol, hexane-2,5-diol, 1,6-hexanediol, heptane-1,2-diol, 1,7-heptanediol, 1,8-octanediol, 1,2-octanediol, 1,9-nonanediol, 1,2-decanediol, 1,10-decanediol, 1,2-dodecanediol, 1,12-dodecanediol, 1,5-hexadiene-3,4-diol, 2,2-bis(4-hydroxycyclohexyl)propane, neopentyl glycol (2,2-dimethylpropane-1,3-diol), 2,2-diethylpropane-1,3-diol, 2-methyl-2-ethylpropane-1,3-diol, 2-methyl-2,4-pentanediol, 2,4-dimethyl-2,4-pentanediol, 2-ethyl-1,3-hexanediol, 2,5-dimethyl-2,5-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, pinacol, diethylene glycol, triethylene glycol, dipropylene glycol, and tripropylene glycol, 1,1-dimethylethane-1,2-diol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-1,3-propanediol, neopentyl glycol, neopentyl glycol hydroxypivalate, 2-ethyl-1,3-hexanediol, 2,4-diethyloctane-1,3-diol, - cyclic aliphatic diol compounds having 3 to 14 carbon atoms, such as tetramethylcyclobutanediol, 1,2-, 1,3- and 1,4-cyclohexanediol, 1,1-, 1,2-, 1,3- and 1,4-cyclohexanedimethanol, 1,2-, 1,3- or 1,4-cyclooctanediol, 4,8-bis(hydroxymethyl)tricyclo[5.2.1.02,6]decane, norbornanediol, pinanediol, decalin diol, 2,2-bis(4-hydroxycyclohexyl)propane, bis(4-hydroxycyclohexane) isopropane; aromatic diols, such as 2,5-bis(hydroxymethyl)furan, 3,4-bis(hydroxymethyl)furan, bis(2-hydroxyethyl) terephthalate, 1,4-benzenediol, hydroquinone bis(2-hydroxyethyl) ether, bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bisphenol C2, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, bisphenol Z, tetrabromobisphenol A, and - aliphatic alcohols having 2 to 20 carbon atoms and additional functional groups, such as or mixtures of two or more thereof.

[0086] According to the invention, hindered amines of the general formula (I) or (II) can also be used as component (M1) to obtain products which in turn contain urea groups which may be cleaved.

[0087] Accordingly, according to a further embodiment, the invention also relates to a method as disclosed above, wherein the component (S) is selected from diisocyanates, polyamines, oligomeric amines, diamines of general formula (I) and amines of general formula (II).

[0088] Suitable isocyanates may be selected from the group consisting of: monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and toluene diisocyanate (TDI).

[0089] Preferably, the at least one isocyanate (i) is selected from the group consisting of: methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), and a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI); more preferably selected from the group consisting of: monomeric methylene diphenylene diisocyanate (mMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and toluene diisocyanate (TDI).

[0090] More preferably, the toluene diisocyanate (TDI) comprises one or more of 2,4-TDI and 2,6-TDI; more preferably consists of the same.

[0091] More preferably, the monomeric methylene diphenylene diisocyanate (mMDI) comprises, more preferably consists of: one or more of 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene(diphenyl diisocyanate) (2,2'-MDI), and 2,4'-methylene(diphenyl diisocyanate) (2,4'-MDI); more preferably 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI). More preferably, the at least one isocyanate (i) is monomeric methylene diphenylene diisocyanate (mMDI), which comprises, more preferably consists of: one or more of 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene(diphenyl diisocyanate) (2,2'-MDI), and 2,4'-methylene(diphenyl diisocyanate) (2,4'-MDI); more preferably 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI).

[0092] Other possible isocyanates are mentioned, for example, in “Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes] Polyurethane [Polyurethane]”, Carl Hanser Verlag, 3rd edition, 1993, Chapters 3.2 and 3.3.2.

[0093] According to a further embodiment, the present invention also relates to a process as disclosed above, wherein component (S) is selected from polyamines, oligoamines, diamines or a mixture of polyamines, oligoamines and diamines of general formula (I).

[0094] According to the invention, the composition comprising the poly(urea-urethane) polymer may also comprise additional components, such as, for example, fillers, pigments or additional additives. Suitable additives are known to those skilled in the art. In particular, fillers, such as, for example, fiber fillers, may be added.

[0095] Therefore, according to a further embodiment, the present invention also relates to a method as disclosed above, wherein the composition comprises a filler selected from the group consisting of glass fibers, carbon fibers, mineral fibers, textiles, metal meshes, metal fibers, metal rods, carbonates, wood and mixtures of two or more thereof.

[0096] In the case where the composition comprises a poly(urea-urethane) polymer and a filler, the mixture (M1) also comprises the filler. In the context of the present invention, the method for recycling as disclosed above may also comprise a suitable separation step to separate the components of the mixture (M1). It is also possible to separate a component from the remaining mixture. The method may also comprise an additional purification step.

[0097] Therefore, according to a further embodiment, the present invention also relates to a method as disclosed above, wherein the method comprises step (ii)

[0098] (ii) separating the components of the mixture obtained in step (i).

[0099] Suitable separation steps are known in principle and may for example comprise a filtering step, a distillation step or an extraction step. The filtering may also be carried out at an elevated temperature, depending on the solubility of the components. Therefore, according to further embodiments, the invention further relates to a method as disclosed above, wherein step (ii) comprises a filtering step.

[0100] The filtration can be performed, for example, at a temperature in the range of 20 to 230°C, preferably in the range of 40 to 200°C, in particular in the range of 60 to 150°C.

[0101] The components of the mixture (M1) can be separated and isolated. The components can be obtained in solution or the solvent can be removed using suitable techniques known to those skilled in the art. The method can also include two or more purification steps.

[0102] This allows the components of the composite material to be obtained, for example, the filler can be separated.

[0103] The separated components can also be reused, especially as starting materials in a method for preparing poly(urea - urethane) polymers.

[0104] Thus, according to a further embodiment, the invention also relates to a method as disclosed above, wherein the method comprises step (iii)

[0105] (iii) preparing a poly(urea - urethane) polymer using one or more of these components obtained in step (ii).

[0106] The method according to the invention comprises step (i), and optionally (ii), and optionally (iii), but can also include additional steps. The method can, for example, include additional purification steps or heat treatment. According to a further embodiment, the invention also relates to a method as disclosed above, wherein the method comprises an additional purification step. Suitable purification steps include, for example, washing steps and drying steps.

[0107] Suitable treatment steps are in principle known to those skilled in the art. Suitable treatment and / or purification steps can be carried out between step (i) and (ii), or between step (ii) and (iii). In the context of the present invention, step (ii) can also be carried out directly after step (i). Step (iii) can also be carried out directly after step (ii).

[0108] According to the invention, a poly(urea - urethane) polymer (PUU1) is obtainable or obtained by a method comprising the following:

[0109] - reacting the following components:

[0110] (i) at least one isocyanate;

[0111] (ii) at least one polyol; and

[0112] (iii) at least one secondary amine having the following formula (I):

[0113]

[0114] wherein -R a- selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; where

[0115] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0116] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0117] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0118] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0119] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0120] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0121] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0122] -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene;

[0123] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0124] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene;

[0125] -Z 11- is C6-C substituted by -NHR or -OR 30 arylene, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 10 alkyl;

[0126] -Z 12 - is -N(R f )-;

[0127] -Z 13 - is substituted or unsubstituted 5- to 30-membered heteroalkylidene, where at least one of one or more heteroatoms of Z 13 comes from X a ;

[0128] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0129] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0130] where

[0131] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heteroalkylidene, substituted or unsubstituted 5- to 30-membered heteroalkenylidene, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylidene C5-C 30Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0132] R b and R e are each independently as R c 、R d 、R f and R g is defined; or

[0133] There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a 、C b 、X a 、X b and R a ; or

[0134] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and

[0135] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both; or

[0136] (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; or

[0137] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and Rd both;

[0138] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently defined as any one of R c , R d , R f and R g below in (A);

[0139] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently defined as any one of R c , R d , R f and R g below in (A).

[0140] Preferably, the at least one secondary amine (iii) has the following formula (I)

[0141]

[0142] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; wherein

[0143] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0144] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene group;

[0145] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene group;

[0146] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene group;

[0147] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene group;

[0148] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene group;

[0149] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene group;

[0150] -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene group;

[0151] -Z9- is a substituted or unsubstituted C6-C 30 arylene group;

[0152] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene group;

[0153] -Z 11 - is a C6-C arylene group substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl groups; 10 alkyl groups;

[0154] -Z 12 - is -N(R f )-;

[0155] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene group, where at least one of one or more heteroatoms of Z 13 is from X a ;

[0156] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0157] where X a is an O atom or NH and X bis an O atom or NH, where X a and X b at least one of which is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0158] wherein

[0159] (A) R c 、R d 、R f and R g are each independently selected from the group consisting of: hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl,

[0160] R b and R e are each independently as defined for R c 、R d 、R f and R g ; or

[0161] there is no R b and R e , and C a and C b are connected to each other via a single bond to form a Ca , C b , X a , X b and R a form a heterocycle; or

[0162] (B) C a and R e form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and without both R f and R g ; and

[0163] C b and R b form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and without both R c and R d both.

[0164] Preferably, each of C a and C b is a C atom.

[0165] Preferably, X a is NH, X b is NH, and the secondary amine (iii) has the following formula (II)

[0166]

[0167] where C a , C b , R b , R c , R d , R e , R f , R g and -R a - are as defined in formula (I).

[0168] Preferably, -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z9-Z1-Z9-, -Z1-Z5-Z1-, -Z1-Z9-Z1- and -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6, preferably selected from the group consisting of: -Z2-, -Z9-Z1-Z9- and -Z9-Z1(-Z 11 -Z1) n-Z9-, where n = 1, 2, 3, 4, 5, or 6, more preferably selected from the group consisting of: -Z2- and -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6.

[0169] Preferably, -Z1- is selected from the group consisting of: -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH2-CH(CH2CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, and -(CH2) 10 -.

[0170] Preferably, when R a is selected from the group consisting of: -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (where n = 1, 2, 3, 4, 5, or 6) and -Z1-Z 12 -Z1-, -Z1- is -CH2-.

[0171] Preferably, -Z9- is selected from the group consisting of phenylene, naphthylene, biphenylene, fluorenylene, and indenylene, where -Z9- is more preferably phenylene.

[0172] Preferably, phenylene is selected from the group consisting of ortho-phenylene, meta-phenylene, and para-phenylene, more preferably ortho-phenylene and para-phenylene.

[0173] Preferably, -R a - is -Z9-Z1-Z9-, where -Z9- is phenylene, more preferably para-phenylene, and -Z1- is -CH2-.

[0174] Preferably, -R a - is -Z9-Z1(-Z 11 -Z1) n-Z9-, where n = 1, 2, 3, 4, 5, or 6, where -Z9- is phenylene and -Z1- is -CH2-, and where -Z 11 - is a C6-arylene substituted with -NHR.

[0175] Preferably, in -Z 11 -, R is -C(R h )(R i )(R j ), where R h , R i and R j are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl. More preferably, R h , R i and R j are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. Even more preferably, R h , R i and R jare independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of hydrogen, methyl and ethyl, more preferably selected from the group consisting of hydrogen, methyl and ethyl. More preferably, R h , R i and R j Any one of them is H, and except the one that is H, R h , R i and R j More preferably, R is CH3 or H. h , R i and R j One of them is ethyl.

[0176] Alternatively, preferably, in -Z 11 -, R is -C(R h )(R i )(R j ), where C and R h Forming substituted or unsubstituted C6-C 30 Arylene, and no R i and R j Both. For example, -Z 11 - may be -NH-Ph.

[0177] In the context of the present invention, preferably, -Z2- is a substituted or unsubstituted, linear or branched, 2- to 500-membered heteroalkylene, more preferably a substituted or unsubstituted, linear or branched, 2- to 35-membered heteroalkylene, more preferably a substituted or unsubstituted, linear or branched, 2- to 30-membered heteroalkylene.

[0178] More preferably, -Z2- is selected from the group consisting of: -CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(where R x1 is -CH2-CH3, where R y1 is [-O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n )(where m1 + n1 + o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C(R l )(R m )(R n )(and where m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O] o3-CH2-CH(CH)3- (where n3 is in the range of 8 to 10 and m3 + o3 is in the range of 3 to 4, or where n3 is in the range of 12 to 13 and m3 + o3 is in the range of 5 to 7, or where n3 is in the range of 38 to 40 and m3 + o3 is in the range of 5 to 7), -[CH-CH2-O] m4 -CH2-CH2- (where m4 is in the range of 8 to 250), and -[CH2-CH2-NH] m5 -(where m5 is in the range of 10 to 100,000).

[0179] More preferably, -Z2- is more preferably -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -, where R x1 is -CH2-CH3, where R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ), where m1 + n1 + o1 is in the range of 5 to 6.

[0180] Preferably, in one or more of R y1 and R y2 , R l , R m and R n are independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl. More preferably, R l 、R m and R n are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. More preferably, R l 、R m and R n are each independently selected from the group consisting of: hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-1-yl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of: hydrogen, methyl and ethyl, more preferably selected from the group consisting of: hydrogen, methyl and ethyl. More preferably, any one of R l 、R m and R n is H, and except for the one that is H, one of R l 、R m and R n is CH3. More preferably, except for the one that is CH3 or H, one of R l 、R m and R n is ethyl. Alternatively, preferably, in one or more of R y1 and R y2 , C and R l form a substituted or unsubstituted C6-C 30 arylene, and there is no R m and R n both. For example, R y1 can be -CH2-[O-CH2-CH(CH3)] n1 -NH-Ph, and R y2 can be [-O-CH2-CH(CH3)] n2 -NH-Ph.

[0181] Preferably, -Z3- is selected from the group consisting of: -CH=CH- and -CH2-CH=CH-.

[0182] Preferably, -Z4- is selected from the group consisting of: -CH=CH-NH-, -CH=CH-O-, -CH=CH-CH2-O-.

[0183] Preferably, -Z5- is selected from the group consisting of cyclohexane-1,4-diyl, cyclohexane-1,3-diyl, and 2,6-diyl-norbornane.

[0184] Preferably, -Z6- is selected from the group consisting of 1,5-dioxaoctylene and 4,8-dioxabicyclo[3.3.0]octylene.

[0185] Preferably, -Z7- is selected from the group consisting of cyclopent-1,2-ene-3,5-diyl, 3-cyclohexene-1,2-diyl, 2,5-cyclohexadiene-1,4-diyl, cyclohex-1,2-ene-3,5-diyl, 2,5-cyclohexadiene-1,4-diyl and cyclohept-1,2-ene-3,5-diyl.

[0186] Preferably, -Z 10 - is a triazinyl group, more preferably one or more of vic-triazinylene, asym-triazinylene and sym-triazinylene.

[0187] Preferably, R c 、R d 、R f and R g are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isoamyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-1-yl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl and -C(OH)H-R k and are more preferably selected from the group consisting of hydrogen, methyl and ethyl, and are even more preferably selected from the group consisting of hydrogen, methyl and ethyl,

[0188] wherein R k is selected from the group consisting of hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl.

[0189] Preferably, R b and R e are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-2-ylmethyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, and more preferably selected from the group consisting of hydrogen, methyl, and ethyl.

[0190] Preferably, any one of R b , R c and R d is H, and any one of R e , R f and R g is H;

[0191] wherein except for the one that is H, one of R b , R c and R d is CH3, and except for the one that is H, one of R e , R f and R g is CH3.

[0192] Preferably, Rb , R c and R d Any one of them is ethyl, and R e , R f and R g Any one of them is ethyl; more preferably, wherein

[0193] Except for the one that is ethyl, R b , R c and R d One of them is H,

[0194] Except for the one that is ethyl, R e , R f and R g One of them is H,

[0195] Except for the one that is ethyl or H, R b , R c and R d One of them is CH3, and

[0196] Except for the one that is ethyl or H, R e , R f and R g One of them is CH3.

[0197] Preferably, the at least one secondary amine (iii) is

[0198] 4,4'-Methylenebis(N-sec-butylaniline) (DIB-MDA).

[0199] Alternatively, preferably, the at least one secondary amine (iii) is a sec-butyl-modified polyetheramine, CH3-CH2-CH(CH3)-NH-[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -NH-CH(CH3)-CH2-CH3, wherein R x1 is -CH2-CH3, wherein R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-CH(CH3)-CH2-CH3, where m1 + n1 + o1 is in the range of 5 to 6.

[0200] Preferably, the at least one secondary amine (iii) is

[0201] DIB-polyetheramine T403, preferably where m1 + n1 + o1 = 5 to 6.

[0202] Alternatively, preferably, the at least one secondary amine (iii) is DIB-diamine (N,N'-di-sec-butyl-1,4-diaminobutane). According to the present invention, 2-(ethylamino)ethanol can also be used.

[0203] In the context of the present invention, suitable isocyanates are known to those skilled in the art per se.

[0204] Preferably, the at least one isocyanate (i) has an NCO functionality of 2 or greater, more preferably 2 or 3.

[0205] Preferably, the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3 or greater, more preferably, the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3.

[0206] Preferably, the at least one isocyanate (i) is selected from the group consisting of monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, xylene 2,6 - diisocyanate, naphthalene 1,5 - diisocyanate (1,5 - NDI), butane 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), octane 1,8 - diisocyanate, nonane 1,9 - diisocyanate, decane 1,10 - diisocyanate, 2,2 - dimethylpentane 1,5 - diisocyanate, 2 - methylpentane 1,5 - diisocyanate (MPDI), 2,4,4(or 2,2,4) - trimethylhexane 1,6 - diisocyanate (TMDI), cyclohexane 1,3 - and 1,4 - diisocyanate, 1 - isocyanato - 3,3,5 - trimethyl - 5 - isocyanatomethylcyclohexane (IPDI), methylene - bis(isocyanatocyclohexane) (H12MDI), 2,4 - or 2,6 - diisocyanato - 1 - methylcyclohexane (H6TDI), 1 - isocyanato - 1 - methyl - 4(3) - isocyanatomethylcyclohexane (AMCI), 1,3 - bis(isocyanatomethyl)cyclohexane, 1,4 - bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane - 4,4',4" - triisocyanate, toluene - 2,4,6 - triyltriisocyanate, ethyl ester 1 - lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, triisocyanatomethylcyclohexane, 1,8 - diisocyanato - 4 - (isocyanatomethyl)octane, undecane 1,6,11 - triisocyanate, 1,7 - diisocyanato - 4 - (3 - isocyanatopropyl)heptane, 1,6 - diisocyanato - 3 - (isocyanatomethyl)hexane, 2,2 - bis[[4 - (isocyanatomethyl)phenyl]methyl]butyl n - [[4 - (isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6 - trioxotriazine - 1,3,5(2h,4h,6h) - triyl) tris(hexamethylene) isocyanate, 1,3,5 - triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3" - [(1h,3h,5h) - 2,4,6 - trioxo - 1,3,5 - triazine - 1,3,5 - triyltri(methylene)] tris[3,5,5 - trimethylcyclohexyl] triisocyanate, 1,3,5 - triazine - 2,4,6 - triisocyanate, 2,4,4' - triisocyanato - dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4' - diphenyl ether triisocyanate, 1,3 - bis(3 - isocyanato - 4 - methylphenyl) - 1,3 - diazetidine - 2,4 - dione and mixtures of two or more thereof,

[0207] More preferably selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), naphthalene 1,5 - diisocyanate (1,5 - NDI), 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), methylene - bis(cyclohexyl isocyanate) (H12MDI), such as dicyclohexylmethane 4,4'- or 2,4'- or 2,2'-diisocyanate, and mixtures of two or more thereof.

[0208] Preferably, the at least one isocyanate (i) is selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and toluene diisocyanate (TDI).

[0209] Preferably, the at least one isocyanate (i) is selected from the group consisting of: methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), and a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI); more preferably selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI) and a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI).

[0210] More preferably, the toluene diisocyanate (TDI) comprises one or more of 2,4 - TDI and 2,6 - TDI, more preferably consists of the same.

[0211] More preferably, the monomeric methylene diphenylene diisocyanate (mMDI) comprises, more preferably consists of, one or more of 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene(diphenyl diisocyanate) (2,2'-MDI) and 2,4'-methylene(diphenyl diisocyanate) (2,4'-MDI), more preferably 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI). More preferably, the at least one isocyanate (i) is monomeric methylene diphenylene diisocyanate (mMDI), which comprises, more preferably consists of, one or more of 4,4'-methylene (diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene (diphenyl diisocyanate) (2,2'-MDI) and 2,4'-methylene (diphenyl diisocyanate) (2,4'-MDI), more preferably 4,4'-methylene (diphenyl diisocyanate) (4,4'-MDI).

[0212] Other possible isocyanates are mentioned, for example, in “Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes] Polyurethane [Polyurethane]”, Carl Hanser Verlag, 3rd edition, 1993, Chapters 3.2 and 3.3.2.

[0213] Suitable polyols are known per se to the person skilled in the art.

[0214] In principle, any polyol conventionally used for preparing polyurethane can be used as polyol.The type of polyol can depend on the desired application purpose.Suitable polyol is polyester polyol, especially including aliphatic polyester polyol and aliphatic aromatic polyester polyol, polyester carbonate polyol, polyether ester polyol, aliphatic polycarbonate polyol, polyacrylate polyol, polyolefin polyol, aliphatic polyether alcohol and mixture thereof.Preferably, this at least one polyol is selected from polyester polyol, particularly aliphatic polyester polyol and aliphatic aromatic polyester polyol, aliphatic polycarbonate polyol, aliphatic polyether alcohol and mixture thereof.Especially, this at least one polyol comprises polyester polyol and / or aliphatic polyether polyol as described herein.Especially, this at least one polyol is selected from polyester polyol, aliphatic polyether polyol and combination thereof.

[0215] Preferably, the at least one polyol (i) is selected from the group consisting of polyester polyols, polyetherester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols and mixtures thereof.

[0216] More preferably, the at least one polyol (i) is selected from the group consisting of polyester polyols and polyether polyols.

[0217] Suitable polyester polyols for use as polyols are in particular aliphatic polyester alcohols and aliphatic / aromatic polyester alcohols, i.e. polyester alcohols based on a dicarboxylic acid component selected from aliphatic dicarboxylic acids, cycloaliphatic dicarboxylic acids, aromatic dicarboxylic acids and combinations thereof and a diol component selected from aliphatic diols, cycloaliphatic diols and polyether polyols.

[0218] Suitable aliphatic diols for the preparation of polyester polyols generally have 2 to 20 C atoms, in particular 3 to 10 C atoms. Examples of aliphatic diols are ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,2-diol, butane-1,3-diol, butane-1,4-diol, butane-2,3-diol, pentane-1,2-diol, pentane-1,3-diol, pentane-1,4-diol, pentane-1,5-diol, pentane-2,3-diol, pentane-2,4-diol, hexane-1,2-diol, hexane-1,3-diol, hexane-1,4-diol, hexane-1,5-diol, hexane-1,6-diol, hexane-2,5-diol, heptane-1,2-diol, 1,7-heptanediol, 1,8-octanediol, 1,2-octanediol, 1,9-nonanediol, 1,2-decanediol, 1,10-decanediol, 1,2-dodecanediol, 1,12-dodecanediol, 1,5-hexadiene-3,4-diol, neopentyl glycol, (2,2-dimethylpropane-1,3-diol), 2,2-diethylpropane-1,3-diol, 2-methyl-2-ethylpropane-1,3-diol, 2-methyl-2,4-pentanediol, 2,4-dimethyl-2,4-pentanediol, 2-ethyl-1,3-hexanediol, 2,5-dimethyl-2,5-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, pinacol, diethylene glycol, triethylene glycol, dipropylene glycol and tripropylene glycol

[0219] Suitable alicyclic diols for preparing polyester polyols generally have 4 to 20 C atoms, especially 5 to 10 C atoms. Examples of alicyclic diols are cyclopentanediol, cyclohexane-1,4-diol, cyclohexane-1,2-dimethanol, cyclohexane-1,3-dimethanol, cyclohexane-1,4-dimethanol, and 2,2,4,4-tetramethylcyclobutane-1,3-diol. Further suitable diols for preparing polyester polyols are polyether diols, especially polyethylene glycol HO(CH2CH2O)n-H, higher polypropylene glycol HO(CH[CH3]CH2O)n-H (where n is an integer and n≥4, for example, 4 to 20), and polyethylene glycol-polypropylene glycol, more particularly those having 4 to 20 repeating units, the sequence of ethyleneoxy and propyleneoxy units can be block or random, and polytetramethylene glycol, more particularly those having 4 to 20 repeating units, and poly-1,3-propanediol, more particularly those having 4 to 20 repeating units.

[0220] Preferred dicarboxylic acids for preparing polyester polyols are aromatic dicarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid, alicyclic dicarboxylic acids preferably having 8 to 12 carbon atoms such as tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexanedicarboxylic acid, and aliphatic dicarboxylic acids preferably having 3 to 40 carbon atoms such as malonic acid, succinic acid, 2-methylsuccinic acid, glutaric acid, 2-methylglutaric acid, 3-methylglutaric acid, α-ketoglutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, brassylic acid, fumaric acid, 2,2-dimethylglutaric acid, suberic acid, diglycolic acid, oxaloacetic acid, glutamic acid, aspartic acid, itaconic acid, and maleic acid and dimer fatty acids such as dimer fatty acids of octadecadienoic acid or dimer fatty acids obtained by dimerization of other polyunsaturated fatty acids or fatty acid mixtures [CAS 61788-89-4].

[0221] The dicarboxylic acids for preparing polyester polyols can be free acids or their esterified derivatives. The derivatives are preferably understood as the corresponding acid anhydrides, monoalkyl esters, and dialkyl esters, preferably mono- and di-C1-C4 alkyl esters, more preferably monomethyl esters and dimethyl esters, and also the corresponding monoethyl esters and diethyl esters, and additionally mono-vinyl esters and di-vinyl esters, and also mixed esters, examples being mixed esters having different C1-C4 alkyl components.

[0222] Among the polyester polyols, preferred are polyester polyols based on a diol component selected from the group consisting of butanediol, neopentyl glycol, hexanediol, ethylene glycol, diethylene glycol, and mixtures thereof and a dicarboxylic acid component selected from the group consisting of adipic acid, phthalic acid, isophthalic acid, and combinations thereof. Particularly preferred are polyester polyols based on butanediol and / or neopentyl glycol and / or hexanediol and adipic acid and / or phthalic acid and / or isophthalic acid.

[0223] Suitable polyester polyols for use as polyols also include polycaprolactones, in particular poly-C4-C12-caprolactones, especially polycaprolactone (PCL). Polycaprolactones refer to aliphatic polyesters obtainable by ring-opening polymerization of lactones, in particular C4-C12-lactones, especially ε-caprolactone. Polycaprolactone has a repeating monomer unit of the general formula [-O-CHR-(CH2) m -CO-], where m is from 4 to 10, m = 4 in the case of caprolactone, and R is hydrogen. In the context of the present invention, the term polycaprolactone is understood to mean both homopolymers of ε-caprolactone and copolymers of ε-caprolactone. Suitable copolymers are, for example, copolymers of ε-caprolactone with monomers selected from the group consisting of lactic acid, lactide, glycolic acid, and glycolide. Polyester polyols are conventional components, which are known, for example, from Ullmanns der technischen Chemie [Encyclopedia of Industrial Chemistry], 4th edition, volume 19, pages 62 to 65.

[0224] Suitable aliphatic polyether polyols for use as polyols are, for example, addition products of C2-C4-alkylene oxides such as ethylene oxide, propylene oxide, 1,2-epoxybutane, 2,3-epoxybutane, or 2-methyloxirane. Further suitable polymeric polyols are aliphatic polyether polyols obtainable by condensation of polyhydric aliphatic alcohols, aliphatic polyether polyols obtained by alkoxylation of aliphatic polyols, amines, and amino alcohols. Suitable polyols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, trimethylolpropane, glycerol, pentaerythritol, triethanolamine (= tris(2-hydroxyethyl)amine), sorbitol, or mixtures thereof. Suitable polyether alcohols generally have an OH functionality in the range from 1.5 to 3.0, especially in the range from 1.8 to 2.5. Suitable polyether alcohols preferably have an OH value in the range from 20 to 300 mg KOH / g, and especially in the range from 30 to 250 mg KOH / g. In the context of the present invention, unless otherwise stated, the OH value is measured according to EN ISO 4629-1:2016.

[0225] Typically, they have a number-average molecular weight Mn determined by gel permeation chromatography as described above in the range from 400 to 10,000 g / mol, preferably in the range from 500 to 5,000 g / mol. Preferred polyether components are polyethylene oxide polyols, polypropylene oxide polyols, and polytetramethylene oxide polyols (poly-THF) having a molecular weight Mn of 400 to 10,000 g / mol, preferably 500 to 5,000 g / mol. In this case, polyether polyols with a particularly low molecular weight can be water-soluble in the case of a correspondingly high OH content.

[0226] Preferably, the at least one polyol (ii) is a polyether polyol, and the polyether polyol is more preferably selected from the group consisting of: polytetrahydrofuran, trifunctional polyether polyols containing secondary hydroxyl groups, polypropylene glycol, sucrose-based polyether polyols, tetrafunctional polyether polyols based on ethylenediamine and propylene oxide, and mixtures of two or more thereof, and more preferably selected from the group consisting of: polytetrahydrofuran and trifunctional polyether polyols containing secondary hydroxyl groups.

[0227] Preferably, the at least one polyol (ii) is a polyether polyol, and the polyether polyol is more preferably selected from the group consisting of: polytetrahydrofuran (f = 2, Mn = 2000 g / mol, OH = 56 mg KOH / g), trifunctional polyether polyols containing secondary hydroxyl groups (f = 3, Mn = 3500 g / mol, OH = 48, viscosity (25 °C) = 600 mPa·s; or f = 3, Mn = 3000 g / mol, OH = 53 mg KOH / g, viscosity (25 °C) = 553 mPa·s), polypropylene glycol (f = 2, Mn = 500 g / mol, OH = 248 mg KOH / g, viscosity (25 °C) = 72 mPa·s), sucrose-based polyether polyols (f = 5, Mn = 500 g / mol, OH = 490 mg KOH / g, viscosity (25 °C) = 8450 mPa·s), tetrafunctional polyether polyols based on ethylenediamine and propylene oxide (f = 4, Mn = 300 g / mol, OH = 753 mg KOH / g, viscosity (25 °C) = 42000 mPa·s), and mixtures of two or more thereof, and more preferably selected from the group consisting of: polytetrahydrofuran (f = 2, Mn = 2000 g / mol, OH = 56 mg KOH / g) and trifunctional polyether polyols containing secondary hydroxyl groups (f = 3, Mn = 3500 g / mol, OH = 48, viscosity (25 °C) = 600 mPa·s; or f = 3, Mn = 3000 g / mol, OH = 53 mg KOH / g, viscosity (25 °C) = 553 mPa·s). For the viscosity at 25 °C: DIN 53 240, and for the OH value, DIN EN 12092.

[0228] Alternatively, aliphatic polycarbonate polyols suitable as polyols are obtainable by reaction of carbonic acid derivatives (e.g. diphenyl carbonate, dimethyl carbonate or phosgene) with diols. Such usable diols include, for example, ethylene glycol, propane-1,2- and -1,3-diol, butane-1,3- and 1,4-diol, hexane-1,6-diol, octane-1,8-diol, neopentyl glycol, 1,4-bishydroxymethyl-cyclohexane, 2-methylpropane-1,3-diol, 2,2,4-trimethylpentane-1,3-diol, dipropylene glycol, polypropylene glycol, dibutylene glycol, polybutylene glycol and also lactone-modified diols. The diol component preferably contains 40% to 100% by weight of hexane-1,6-diol and / or hexanediol derivatives, preferably those with ether or ester groups and terminal OH groups, such as the products obtained by the reaction of 1 mol of hexanediol with at least 1 mol, preferably 1 to 2 mol, of ε-caprolactone or by etherification of hexanediol itself to obtain di- or trihexanediol. Polyether polycarbonate polyols can also be used. Among the aliphatic polycarbonate polyols, preferred are polycarbonate polyols based on dimethyl carbonate and hexanediol and / or butanediol and / or ε-caprolactone. Very particularly preferred are polycarbonate polyols based on dimethyl carbonate and hexanediol and / or ε-caprolactone. Preferred polycarbonate polyols have a molecular weight Mn of 400 to 10.000 g / mol, preferably 500 to 5.000 g / mol, as determined by gel permeation chromatography as described above.

[0229] Other possible polyols are mentioned, for example, in “Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes] Polyurethane [Polyurethane]”, Carl Hanser Verlag, 3rd edition, 1993, Chapters 3.1, 3.2 and 3.3.2.

[0230] Preferably, the at least one isocyanate (i), the at least one polyol (ii) and the at least one secondary amine (iii) are reacted in the absence of a solvent.

[0231] Preferably, the poly(urea-urethane) polymer (PUU1) is obtainable or obtained by a process comprising

[0232] (i), (ii) and / or (iii), more preferably (i) and (ii), are reacted with at least one additive, wherein the at least one additive is selected from the group consisting of benzoyl chloride and diethylene glycol bischloroformate.

[0233] Any other additives other than those known to the skilled person as listed above may be used in the reactions of (i), (ii) and / or (iii).

[0234] Preferably, the poly(ureaurethane) polymer (PUU1) is obtainable or obtained in the absence of a catalyst.

[0235] Preferably, the poly(ureaurethane) polymer (PUU1) is obtainable or obtained by a process comprising

[0236] - reacting the at least one isocyanate (i) with the at least one polyol (ii) to obtain a prepolymer, and

[0237] - reacting the obtained prepolymer with the at least one secondary amine (iii);

[0238] or

[0239] - reacting the at least one isocyanate (i) with the at least one secondary amine (iii) to obtain a prepolymer, and

[0240] - reacting the obtained prepolymer with the at least one polyol (ii).

[0241] Preferably, the molar ratio of -NCO of the at least one isocyanate (i) to -OH of the at least one polyol (ii) is in the range of 1:0.50 to 1:0.10, more preferably in the range of 1:0.40 to 1:0.15, more preferably in the range of 1:0.30 to 1:0.20.

[0242] Preferably, the molar ratio of -NCO of the at least one isocyanate (i) to -NH- of the at least one secondary amine (iii) is in the range of 1:1.50 to 1:0.5, more preferably in the range of 1:1.20 to 1:0.60, more preferably in the range of 1:0.8 to 1:0.7.

[0243] Preferably, the reactions of components (i), (ii) and / or (iii) are carried out at a temperature in the range of greater than 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0244] Preferably, the poly(ureaurethane) polymer (PUU1) is obtainable or obtained by a process further comprising curing the mixture of (i), (ii) and (iii), more preferably at a temperature in the range of 90 °C to 200 °C, more preferably in the range of 100 °C to 150 °C.

[0245] Preferably, the poly(ureaurethane) polymer (PUU1) is thermoplastic or thermosetting.

[0246] Preferably, the poly(ureaurethane) polymer (PUU1) of the present invention is a covalently adaptable polymer, preferably a covalently adaptable network (CAN) thermoset or a covalently adaptable system (CAS) / thermoplastic.

[0247] Preferably, the poly(ureaurethane) polymer (PUU1) of the present invention is recyclable.

[0248] Preferably, the poly(ureaurethane) polymer has a solubility in toluene in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure, more preferably the poly(ureaurethane) polymer has a solubility in toluene in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure.

[0249] Preferably, the poly(ureaurethane) polymer has a solubility in 1,3-dimethyl-2-imidazolidinone in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure, more preferably the poly(ureaurethane) polymer has a solubility in an organic solvent in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure.

[0250] Preferably, the poly(ureaurethane) polymer has a melting point determined by a hot press in the range of 10 °C to 200 °C, more preferably in the range of 50 °C to 190 °C, more preferably in the range of 60 °C to 180 °C under a pressure of 20 kN. According to the present invention, to determine the melting point, a circular press with a diameter of 17 cm (pressure of about 880 kPa, press brand: Fa. Weber model number: PW20H (2006)) is used.

[0251] The present invention further discloses a composite material based on a poly(ureaurethane) polymer, which can be obtained or has been obtained by

[0252] - reacting the following components:

[0253] (i) at least one isocyanate;

[0254] (ii) at least one polyol; and

[0255] (iii) at least one secondary amine having the following formula (I):

[0256]

[0257] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 - —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; wherein

[0258] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0259] -Z2- is a substituted or unsubstituted, straight-chain or branched 2-membered to 300,000-membered heteroalkylene;

[0260] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0261] -Z4- is a substituted or unsubstituted, straight-chain or branched 3-membered to 30-membered heteroalkenylene;

[0262] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0263] -Z6- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkylene;

[0264] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0265] -Z8- is a substituted or unsubstituted 5- to 30-membered heteroalkenyl;

[0266] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0267] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroaryl;

[0268] -Z 11 - is an arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10

[0269] -Z 12 - is -N(R f )-;

[0270] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heteroalkyl, where at least one of one or more heteroatoms of Z 13 is from X a ;

[0271] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0272] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b being NH, the corresponding C a and / or C b is a C atom;

[0273] where

[0274] (A) R c 、R d 、R f and R g are each independently selected from the group consisting of hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 ​Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0275] R b and R e are each independently as defined for R c , R d , R f and R g ; or

[0276] There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or

[0277] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and

[0278] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both; or

[0279] (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and no R f and R g both; or

[0280] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and no R c and R d both;

[0281] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in any one of (A);

[0282] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A),

[0283] obtain a mixture, preferably a polymer;

[0284] and

[0285] - contacting the obtained mixture, preferably the obtained polymer, with (iv):

[0286] (iv) a filler selected from the group consisting of: glass fiber, carbon fiber, mineral fiber, textile, metal mesh, metal fiber, metal rod, carbonate, wood, and mixtures of two or more thereof.

[0287] Preferably, the at least one secondary amine (iii) has the following formula (I)

[0288]

[0289] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 - where n = 1, 2, 3, 4, 5, or 6 - and -Z1-Z 12 -Z1-; wherein

[0290] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0291] -Z2- is a substituted or unsubstituted, straight-chain or branched 2-membered to 300,000-membered heteroalkylene;

[0292] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0293] -Z4- is a substituted or unsubstituted, straight-chain or branched 3-membered to 30-membered heteroalkenylene;

[0294] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0295] -Z6- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkylene;

[0296] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0297] -Z8- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkenylene;

[0298] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0299] -Z 10 - is a substituted or unsubstituted 5-membered to 30-membered heteroarylene;

[0300] -Z11 - is a C6-C arylene group substituted by -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl groups; 10 -Z

[0301] -Z 12 - is -N(R f )-;

[0302] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heteroalkylidene group, where at least one of the one or more heteroatoms in Z 13 comes from X a ;

[0303] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0304] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0305] where

[0306] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl groups, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl groups, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl groups, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 cycloalkyl groups, substituted or unsubstituted C5-C 30 cycloalkenyl groups, substituted or unsubstituted 5- to 30-membered heteroalkylidene groups, substituted or unsubstituted 5- to 30-membered heteroalkenylidene groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted 5- to 30-membered heteroaryl groups, substituted or unsubstituted C1-C 10 alkylidene C5-C30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0307] R b and R e are each independently as defined for R c , R d , R f and R g as defined; or

[0308] There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or

[0309] (B) C a and R e form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and there is no R f and R g both; and

[0310] C b and R b form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and there is no R c and R d both.

[0311] Preferably, the filler (iv) is glass fiber.

[0312] Preferably, the at least one polyol, the at least one isocyanate and the at least one secondary amine are as defined above for the poly(urea - urethane) polymer.

[0313] In addition, the present invention discloses a method for preparing the poly(urea - urethane) polymer of the present invention, which includes:

[0314] (a) React at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0315] (b) Contact the prepolymer obtained in (a) with at least one secondary amine to obtain a poly(urea - urethane) polymer, where the at least one secondary amine has the formula (I) as defined in the present invention; or

[0316] (a’) React at least one isocyanate (i) with at least one secondary amine to obtain a prepolymer, where the at least one secondary amine has the formula (I) as defined in the present invention;

[0317] (b’) Contact the prepolymer obtained in (a’) with at least one polyol (ii) to obtain a poly(urea - urethane) polymer.

[0318] Preferably, (a) or (a’) is carried out at a temperature in the range of 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0319] Preferably, one or more of (a) and (b) or one or more of (a’) and (b’), more preferably (a) and (b) or (a’) and (b’) are carried out in the absence of a solvent.

[0320] Preferably, (b) or (b’) is carried out at a temperature in the range of 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0321] Preferably, the method further comprises

[0322] (c) Cure the mixture obtained in (b) or (b’), more preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C.

[0323] In addition, the present invention discloses a method for preparing a composite material according to the present invention, the method comprising:

[0324] (1) Provide a poly(urea urethane) polymer, which comprises

[0325] (1.1) React at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0326] (1.2) Contact the prepolymer obtained in (1.1) with at least one secondary amine, where the at least one secondary amine (iii) has the formula (I) as defined in the present invention;

[0327] or

[0328] (1.1’) React at least one isocyanate (i) with at least one secondary amine, where the at least one secondary amine (iii) has the formula (I) as defined in the present invention, to obtain a prepolymer;

[0329] (1.2’) Contact the prepolymer obtained in (1.1’) with at least one polyol (ii);

[0330] (2) Contact the polymer obtained in (1.2) or (1.2’) with a filler (iv) as defined in the present invention.

[0331] Preferably, (1) is carried out at a temperature in the range of 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0332] Preferably, one or more of (1) and (2), more preferably (1) and (2), are carried out in the absence of a solvent.

[0333] Preferably, in (2), the contact of the polymer with the filler is carried out by mixing or pressing.

[0334] In the context of the present invention, it is also conceivable that in step (2), other thermomechanical methods are used, such as injection molding, casting.

[0335] Preferably, the pressing is carried out at a pressure in the range of 10 to 30 kN, more preferably in the range of 15 to 25 kN, more preferably in the range of 18 to 22 kN.

[0336] Preferably, the pressing is a hot pressing, more preferably at a temperature in the range of 100 °C to 200 °C, more preferably in the range of 120 °C to 160 °C, more preferably in the range of 130 °C to 150 °C.

[0337] Preferably, the pressing is carried out for a duration in the range of 1 to 60 min, more preferably in the range of 4 to 20 min, more preferably in the range of 5 to 10 min.

[0338] Preferably, the method further comprises

[0339] (1.3) Cure the polymer obtained in (1.2) or (1.2’), more preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C;

[0340] or

[0341] (3) The polymer obtained in (2) is more preferably cured at a temperature in the range of 90°C to 150°C, more preferably in the range of 100°C to 120°C.

[0342] The present invention further relates to the use of the poly(urea - urethane) polymer according to the present invention or the poly(urea - urethane) polymer composite material according to the present invention as a recyclable material.

[0343] The present invention further discloses a recyclable article comprising the poly(urea - urethane) polymer according to the present invention or the poly(urea - urethane) polymer composite material according to the present invention.

[0344] The present invention further discloses a method for shaping the poly(urea - urethane) polymer according to the present invention or the poly(urea - urethane) polymer obtainable or obtained by the method according to the present invention, which comprises:

[0345] Shaping the poly(urea - urethane) polymer, wherein shaping the polymer comprises

[0346] (x) Applying pressure and heat to the poly(urea - urethane) polymer to obtain a shaped body, more preferably a foil or sheet; or

[0347] (x’) Extruding the poly(urea - urethane) polymer to obtain a shaped body, more preferably granules or a paste.

[0348] Preferably, the pressure applied according to (x) is in the range of 10 3 to 10 7 Pa, more preferably in the range of 1.5 x 10 3 to 10 6 Pa.

[0349] Preferably, the heating according to (x) is carried out at a temperature in the range of 60°C to 250°C, more preferably in the range of 65°C to 150°C, more preferably in the range of 70°C to 130°C.

[0350] Preferably, the extrusion according to (x’) is carried out at a temperature in the range of 140°C to 220°C, more preferably in the range of 160°C to 200°C, more preferably in the range of 170°C to 190°C.

[0351] Preferably, the poly(urea - urethane) polymer is extruded with a torque in the range of 2.0 to 2.4 Nm, more preferably with a maximum torque of 2.2 Nm. This value is determined using an Xplore Microcompounder MC15 as an extruder.

[0352] According to the present invention, the mixture (M1) contains a prepolymer. According to a further aspect, the present invention also relates to a prepolymer obtainable or obtained according to the method as disclosed above.

[0353] Preferably, the obtained prepolymer contains a blocked urea bond. It is also possible according to the present invention to recycle the obtained prepolymer, for example for the preparation of a poly(urea - urethane) polymer.

[0354] It is also possible that the product of the method according to the present invention is a poly(urea - urethane) polymer. According to a further embodiment, the present invention thus also relates to a poly(urea - urethane) polymer obtainable or obtained according to the method as disclosed above.

[0355] According to a further aspect, the present invention also relates to the use of the prepolymer according to the present invention for the preparation of a poly(urea - urethane) polymer.

[0356] The results show that the poly(urea - urethane) polymer can be reprocessed and recycled under mild conditions while still maintaining its chemical and mechanical properties due to the dynamic reversibility of the HUB.

[0357] Therefore, due to the reversible nature of the formed bonds, the catalyst - free poly(urea - urethane) polymer exhibits excellent reprocessability and recyclability without chemical changes or loss of mechanical properties.

[0358] The present invention is further illustrated by the following groups of examples and by the combination of examples obtained from the dependencies and cross - references as shown. In particular, it should be noted that in each case where a series of examples is mentioned, for example in the context of a term such as "a method as described in any one of Examples 1 to 4", each example in this series is intended to be clearly disclosed to the person skilled in the art, i.e., the wording of this term should be understood by the person skilled in the art as being synonymous with "a method as described in any one of Examples 1, 2, 3, and 4". Furthermore, it should be clearly stated that the following groups of examples represent a suitable structural part of the general description of the preferred aspects of the present invention and thus appropriately support but do not represent the claims of the present invention.

[0359] 1. A method for recycling a composition comprising a poly(urea - urethane) polymer (PUU1), the method comprising step (i):

[0360] (i) Treating the composition comprising the poly(urea - urethane) polymer (PUU1) under conditions suitable for at least partially cleaving the urea bonds of the polymer to obtain a mixture (M1) containing a prepolymer,

[0361] The poly(urea - urethane) polymer (PUU1) is obtainable or obtained by a method comprising the following:

[0362] - React the following components:

[0363] (i) At least one isocyanate;

[0364] (ii) At least one polyol; and

[0365] (iii) At least one secondary amine having the following formula (I):

[0366]

[0367] where -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; where

[0368] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0369] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0370] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0371] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0372] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0373] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0374] -Z7- is a substituted or unsubstituted C5-C 30 subcycloalkenyl;

[0375] -Z8- is a substituted or unsubstituted 5- to 30-membered hetero-subcycloalkenyl;

[0376] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0377] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene;

[0378] -Z 11 - is a C6-C arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10

[0379] -Z 12 - is -N(R f );

[0380] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkyl, where at least one of the one or more heteroatoms of Z 13 is from X a ;

[0381] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0382] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b being NH, the corresponding C a and / or C b is a C atom;

[0383] where

[0384] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C​30 Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0385] R b and R e are each independently as defined for R c , R d , R f and R g ; or

[0386] There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or

[0387] (B) C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and

[0388] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R dboth; or

[0389] (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and without R f and R g both; or

[0390] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and without R c and R d both;

[0391] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in any one of (A);

[0392] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A).

[0393] 2. The method according to embodiment 1, wherein the conditions applied in step (i) are suitable for cleaving the urea bonds of the polymer while the carbamate bonds are substantially stable.

[0394] 3. The method according to embodiment 1 or 2, wherein step (i) is a treatment at a temperature in the range of 60 °C to 200 °C and at a pressure in the range of 1 bar to 200 bar or in the range of 50 mbar to 1 bar.

[0395] 4. The method according to any one of embodiments 1 to 3, wherein an aprotic solvent is added in step (i).

[0396] 5. The method according to any one of embodiments 1 to 4, wherein the aprotic solvent is selected from the group consisting of aliphatic hydrocarbons, halogenated hydrocarbons, ethers, aromatic hydrocarbons, esters, amides, sulfoxides and sulfones, ketones, and mixtures thereof.

[0397] 6. The method according to any one of embodiments 1 to 5, wherein in step (i), a component (S) suitable for reacting with the free functional groups of the cleaved urea bonds is added.

[0398] 7. The method according to embodiment 6, wherein the component (S) is selected from the group consisting of polyols, diols, polyisocyanates, diisocyanates, polyamines, oligomeric amines, diamines, and amines of general formula (II).

[0399] 8. The method according to embodiment 7, wherein the component (S) is selected from diisocyanates, polyamines, oligomeric amines, diamines of general formula (I), and amines of general formula (II).

[0400] 9. The method according to embodiment 7, wherein the component (S) is a polyamine, an oligomeric amine, or a diamine of general formula (I).

[0401] 10. The method according to any one of embodiments 1 to 9, wherein the composition comprises a filler selected from the group consisting of glass fibers, carbon fibers, mineral fibers, textiles, metal meshes, metal fibers, metal rods, carbonates, wood, and mixtures of two or more thereof.

[0402] 11. The method according to any one of embodiments 1 to 10, wherein the method comprises step (ii)

[0403] (ii) separating the components of the mixture obtained in step (i).

[0404] 12. The method according to embodiment 11, wherein step (ii) comprises a filtration step.

[0405] 13. The method according to embodiment 12, wherein the filtration is carried out at a temperature in the range of 20 °C to 200 °C.

[0406] 14. The method according to any one of embodiments 1 to 13, wherein the method comprises step (iii)

[0407] (iii) preparing a poly(urea - urethane) polymer using one or more of the components obtained in step (ii).

[0408] 15. The method according to any one of embodiments 1 to 14, wherein the method comprises an additional purification step.

[0409] 16. According to the method of any one of embodiments 1 to 15, wherein the method comprises an additional filtration step.

[0410] 17. A prepolymer obtainable or obtained according to the method of any one of embodiments 1 to 15.

[0411] 18. According to the prepolymer of embodiment 17, wherein the prepolymer contains a HUB.

[0412] 19. A poly(urea - urethane) polymer obtainable or obtained according to the method of any one of embodiments 1 to 15.

[0413] 20. Use of the prepolymer according to embodiment 17 or 18 for the preparation of a poly(urea - urethane) polymer.

[0414] 21. A poly(urea - urethane) polymer obtainable or obtained by a method of preparing the poly(urea - urethane) polymer by using the prepolymer according to embodiment 11.

[0415] 22. As the method of any one of embodiments 1 to 15, wherein X a is NH, X b is NH, and the secondary amine (iii) has the following formula (II):

[0416]

[0417] wherein C a 、C b 、R b 、R c 、R d 、R e 、R f 、R g and -R a - are as defined in formula (I).

[0418] 23. As the method of any one of embodiments 1 to 15 or 22, wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1 - Z5-, -Z5 - Z1 - Z5-, -Z9 - Z1 - Z9-, -Z1 - Z5 - Z1-, -Z1 - Z9 - Z1- and -Z9 - Z1(-Z 11 - Z1) n - Z9-, where n = 1, 2, 3, 4, 5, or 6, preferably selected from the group consisting of: -Z2-, -Z9 - Z1 - Z9- and -Z9 - Z1(-Z 11 - Z1) n-Z9-, where n = 1, 2, 3, 4, 5, or 6, more preferably selected from the group consisting of: -Z2- and -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6.

[0419] 24. The method according to any one of Examples 1 to 15 or 22 to 23, wherein -Z1- is selected from the group consisting of: -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH2-CH(CH2CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, and -(CH2) 10 -.

[0420] 25. The method according to any one of Examples 1 to 15 or 22 to 24, wherein -Z9- is selected from the group consisting of phenylene, naphthylene, biphenylene, fluorene, and indenyl, and -Z9- is preferably phenylene.

[0421] 26. The method according to Example 25, wherein -R a - is -Z9-Z1-Z9-, where -Z9- is phenylene, preferably p-phenylene, and -Z1- is -CH2-.

[0422] 27. The method according to Example 25, wherein -R a - is -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6, where -Z9- is phenylene and -Z1- is -CH2-, and where -Z 11 - is a C6-arylene group substituted with -NHR.

[0423] 28. The method according to any one of Examples 1 to 15 or 22 to 25, wherein -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 500-membered heteroalkylene group, preferably a substituted or unsubstituted, straight-chain or branched 2- to 35-membered heteroalkylene group, more preferably a substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkylene group.

[0424] 29. The method according to embodiment 28, wherein -Z2- is selected from the group consisting of: -CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(wherein R x1 is -CH2-CH3, wherein R y1 is [-O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ), where m1 + n1 + o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(wherein R y2 is [-O-CH2-CH(CH3)] n2 -NH-C(R l )(R m )(R n ), and where m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O]o3 -CH2-CH(CH)3- (where n3 is in the range of 8 to 10 and m3 + o3 is in the range of 3 to 4, or where n3 is in the range of 12 to 13 and m3 + o3 is in the range of 5 to 7, or where n3 is in the range of 38 to 40 and m3 + o3 is in the range of 5 to 7), -[CH-CH2-O] m4 -CH2-CH2- (where m4 is in the range of 8 to 250), and -[CH2-CH2-NH] m5 -(where m5 is in the range of 10 to 100,000);

[0425] where -Z2- is preferably -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -, where R x1 is -CH2-CH3, where R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ), where m1 + n1 + o1 is in the range of 5 to 6.

[0426] 30. The method according to any one of embodiments 1 to 15 or 22 to 29, wherein R c , R d , R f and R g are independently selected from the group consisting of: hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-alkyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl and -C(OH)H-R k , preferably selected from the group consisting of: hydrogen, methyl and ethyl, more preferably selected from the group consisting of: hydrogen, methyl and ethyl,

[0427] where R k is selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl.

[0428] 31. The method according to any one of Examples 1 to 15 or 22 to 30, wherein R b and R e are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-1-ylmethyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of hydrogen, methyl, and ethyl.

[0429] 32. The method according to any one of Examples 1 to 15 or 22 to 31, wherein any one of R b , R c and R d is H, and any one of R e , R f and R g is H;

[0430] wherein except for the one that is H, one of R b , R c and R d is CH3, and except for the one that is H, one of R e , R f and Rg One of them is CH3.

[0431] 33. The method according to any one of Examples 1 to 15 or 22 to 32, wherein R b , R c and R d Any one of them is ethyl, and R e , R f and R g Any one of them is ethyl;

[0432] Preferably, wherein

[0433] Except for the one that is ethyl, R b , R c and R d One of them is H,

[0434] Except for the one that is ethyl, R e , R f and R g One of them is H,

[0435] Except for the one that is ethyl or H, R b , R c and R d One of them is CH3, and

[0436] Except for the one that is ethyl or H, R e , R f and R g One of them is CH3.

[0437] 34. The method according to Example 33, wherein the at least one secondary amine (iii) is 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA), or wherein the at least one secondary amine (iii) is DIB-diamine (N,N'-di-sec-butyl-1,4-diamine).

[0438] 35. The method according to Example 33, wherein the at least one secondary amine (iii) is a sec-butyl-modified polyetheramine, CH3-CH2-CH(CH3)-NH-[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -NH-CH(CH3)-CH2-CH3, wherein R x1 is -CH2-CH3, wherein R y1 is -CH2-[O-CH2-CH(CH3)] n1-NH-CH(CH3)-CH2-CH3, where m1 + n1 + o1 is in the range of 5 to 6.

[0439] 36. The method according to any one of Examples 1 to 15 or 22 to 35, wherein the at least one isocyanate (i) has an NCO functionality of 2 or greater, preferably 2 or 3, and preferably the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3 or greater, and preferably the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3.

[0440] 37. The method according to any one of Examples 1 to 15 or 22 to 36, wherein the at least one isocyanate (i) is selected from the group consisting of: monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, 2,6 - diisocyanatoxylene, naphthalene 1,5 - diisocyanate (1,5 - NDI), butane 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), octane 1,8 - diisocyanate, nonane 1,9 - diisocyanate, decane 1,10 - diisocyanate, 2,2 - dimethylpentane 1,5 - diisocyanate, 2 - methylpentane 1,5 - diisocyanate (MPDI), 2,4,4(or 2,2,4) - trimethylhexane 1,6 - diisocyanate (TMDI), cyclohexane 1,3 - and 1,4 - diisocyanates, 1 - isocyanato - 3,3,5 - trimethyl - 5 - isocyanatomethylcyclohexane (IPDI), methylene - bis(isocyanatocyclohexane) (H12MDI), 2,4 - or 2,6 - diisocyanato - 1 - methylcyclohexane (H6TDI), 1 - isocyanato - 1 - methyl - 4(3) - isocyanatomethylcyclohexane (AMCI), 1,3 - bis(isocyanatomethyl)cyclohexane, 1,4 - bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane - 4,4',4" - triisocyanate, toluene - 2,4,6 - triyltriisocyanate, ethyl ester 1 - lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, tris(isocyanatomethyl)cyclohexane, 1,8 - diisocyanato - 4 - (isocyanatomethyl)octane, undecane 1,6,11 - triisocyanate, 1,7 - diisocyanato - 4 - (3 - isocyanatopropyl)heptane, 1,6 - diisocyanato - 3 - (isocyanatomethyl)hexane, 2,2 - bis[[4 - (isocyanatomethyl)phenyl]methyl]butyl n - [[4 - (isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6 - trioxotriazine - 1,3,5(2h,4h,6h) - triyl)tri(hexamethylene) isocyanate, 1,3,5 - triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3" - [(1h,3h,5h) - 2,4,6 - trioxo - 1,3,5 - triazine - 1,3,5 - triyltri(methylene)]tris[3,5,5 - trimethylcyclohexyl]triisocyanate, 1,3,5 - triazine - 2,4,6 - triisocyanate, 2,4,4' - triisocyanato - dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4' - diphenyl ether triisocyanate, 1,3 - bis(3 - isocyanato - 4 - methylphenyl)-1,3 - diazetidine - 2,4 - dione and mixtures of two or more thereof,

[0441] preferably selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), mixtures of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), naphthalene 1,5 - diisocyanate (1,5 - NDI), 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), methylene - bis(isocyanatocyclohexane) (H12MDI), and mixtures of two or more thereof.

[0442] 38. The method according to embodiment 37, wherein the at least one isocyanate (i) is selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), mixtures of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and toluene diisocyanate (TDI).

[0443] 39. The method according to any one of embodiments 1 to 15 or 22 to 38, wherein the at least one polyol (i) is selected from the group consisting of: polyester polyols, polyether ester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols, and mixtures thereof.

[0444] 40. The method according to embodiment 39, wherein the at least one polyol (i) is selected from the group consisting of polyester polyols and polyether polyols.

[0445] 41. The method according to embodiment 40, wherein the at least one polyol (ii) is a polyether polyol, and the polyether polyol is preferably selected from the group consisting of: polytetrahydrofuran, trifunctional polyether polyols containing secondary hydroxyl groups, polypropylene glycol, sucrose - based polyether polyols, tetrafunctional polyether polyols based on ethylenediamine and propylene oxide, and mixtures of two or more thereof, more preferably from the group consisting of polytetrahydrofuran and trifunctional polyether polyols containing secondary hydroxyl groups.

[0446] 42. The method according to any one of embodiments 1 to 15 or 22 to 41, wherein the at least one isocyanate (i), the at least one polyol (ii), and the at least one secondary amine (iii) are reacted in the absence of a solvent.

[0447] 43. The method according to any one of Examples 1 to 15 or 22 to 42, wherein the polymer (PUU1) can be obtained or is obtained by a method comprising the following:

[0448] Reacting (i), (ii) and / or (iii), preferably (i) and (ii), with at least one additive selected from the group consisting of benzoyl chloride and diethylene glycol bischloroformate.

[0449] 44. The method according to any one of Examples 1 to 15 or 22 to 43, wherein the polymer (PUU1) can be obtained or is obtained by a method in the absence of a catalyst.

[0450] 45. The method according to any one of Examples 1 to 15 or 22 to 44, wherein the poly(ureaurethane) polymer (PUU1) is obtained or can be obtained by a method comprising the following:

[0451] - Reacting the at least one isocyanate (i) with the at least one polyol (ii) to obtain a prepolymer, and

[0452] - Reacting the obtained prepolymer with the at least one secondary amine (iii);

[0453] or

[0454] Obtained or can be obtained by a method comprising the following:

[0455] - Reacting the at least one isocyanate (i) with the at least one secondary amine (iii) to obtain a prepolymer, and

[0456] - Reacting the obtained prepolymer with the at least one polyol (ii).

[0457] 46. The method according to any one of Examples 1 to 15 or 22 to 45, wherein the molar ratio of -NCO of the at least one isocyanate (i) to -OH of the at least one polyol (ii) is in the range of 1:0.50 to 1:0.10, preferably in the range of 1:0.40 to 1:0.15, more preferably in the range of 1:0.30 to 1:0.20.

[0458] 47. The method according to any one of Examples 1 to 15 or 22 to 46, wherein the molar ratio of -NCO of the at least one isocyanate (i) to -NH- of the at least one secondary amine (iii) is in the range of 1:1.50 to 1:0.5, preferably in the range of 1:1.20 to 1:0.60, more preferably in the range of 1:0.8 to 1:0.7.

[0459] 48. The method according to any one of Examples 1 to 15 or 22 to 47, wherein the reaction of these components (i), (ii) and / or (iii) is carried out at a temperature in the range of greater than 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, even more preferably in the range of 20 °C to 90 °C.

[0460] 49. The method according to any one of Examples 1 to 15 or 22 to 47, wherein the poly(urea - urethane) polymer (PUU1) is obtained or obtainable by a method further comprising curing a mixture of (i), (ii) and (iii) preferably at a temperature in the range of 90 °C to 200 °C, more preferably in the range of 100 °C to 150 °C.

[0461] 50. The method according to any one of Examples 1 to 15 or 22 to 49, wherein the poly(urea - urethane) polymer (PUU1) is thermoplastic or thermosetting.

[0462] 51. The method according to any one of Examples 1 to 15 or 22 to 50, wherein the poly(urea - urethane) polymer (PUU1) has a solubility in toluene in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) as measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure, preferably a solubility in toluene in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) as measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure.

[0463] 52. The method according to any one of Examples 1 to 15 or 22 to 51, wherein the poly(urea - urethane) polymer (PUU1) has a solubility in 1,3 - dimethyl - 2 - imidazolidinone in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) as measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure, preferably a solubility in an organic solvent in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) as measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure.

[0464] 53. The method according to any one of Examples 1 to 15 or 22 to 52, wherein the poly(ureaurethane) polymer (PUU1) has a melting point determined by a hot press in the range of 10 °C to 200 °C, preferably in the range of 50 °C to 190 °C, more preferably in the range of 60 °C to 180 °C, under a pressure of 20 kN.

[0465] 54. The method according to any one of Examples 1 to 15 or 22 to 53, wherein the composite material based on the poly(ureaurethane) polymer can be obtained or is obtained by:

[0466] - reacting the following components:

[0467] (i) at least one isocyanate;

[0468] (ii) at least one polyol; and

[0469] (iii) at least one secondary amine having the following formula (I):

[0470]

[0471] where -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; where

[0472] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0473] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0474] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0475] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0476] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0477] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0478] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0479] -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene;

[0480] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0481] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene;

[0482] -Z 11 - is an arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10

[0483] -Z 12 - is -N(R f )-;

[0484] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where at least one of the one or more heteroatoms of Z 13 is from X a ;

[0485] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0486] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b ​is NH, corresponding C a and / or C b is a C atom;

[0487] wherein

[0488] (A) R c 、R d 、R f and R g are each independently selected from the group consisting of: hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl,

[0489] R b and R e are each independently as defined for R c 、R d 、R f and R g ; or

[0490] there is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a 、C b 、X a 、X b and R a ; or

[0491] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, and without R f and R g both; and

[0492] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and without R c and R d both; or

[0493] (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and without R f and R g both; or

[0494] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and without R c and R d both;

[0495] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in any one of (A);

[0496] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A),

[0497] obtain a mixture comprising a poly(urea - urethane) polymer, preferably a polymer;

[0498] and

[0499] - contacting the obtained mixture, preferably the polymer, with component (iv):

[0500] (iv) a filler selected from the group consisting of: glass fibers, carbon fibers, mineral fibers, textiles, metal meshes, metal fibers, metal rods, carbonates, wood, and mixtures of two or more thereof.

[0501] 55. The method according to embodiment 54, wherein the filler (iv) is glass fibers.

[0502] 56. The method according to any one of embodiments 1 to 15 or 22 to 55, wherein the method for preparing the poly(urea - urethane) polymer comprises:

[0503] (a) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0504] (b) contacting the prepolymer obtained in (a) with at least one secondary amine having the formula (I) as defined in any one of embodiments 1 to 15 to obtain the poly(urea - urethane) polymer; or

[0505] (a’) reacting at least one isocyanate (i) with at least one secondary amine having the formula (I) as defined in any one of embodiments 1 to 15 to obtain a prepolymer;

[0506] (b’) contacting the prepolymer obtained in (a’) with at least one polyol (ii) to obtain the poly(urea - urethane) polymer.

[0507] 57. The method according to embodiment 56, wherein (a) or (a’) is carried out at a temperature in the range of 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, and even more preferably in the range of 20 °C to 90 °C.

[0508] 58. The method according to embodiment 56 or 57, wherein one or more of (a) and (b) or one or more of (a’) and (b’), preferably (a) and (b) or (a’) and (b’), are carried out in the absence of a solvent.

[0509] 59. The method according to any one of embodiments 56 to 58, wherein (b) or (b’) is carried out at a temperature in the range of 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, and even more preferably in the range of 20 °C to 90 °C.

[0510] 60. The method according to any one of Examples 56 to 59, further comprising

[0511] (c) curing the mixture obtained in (b) or (b’) at a temperature preferably in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C.

[0512] 61. The method according to any one of Examples 1 to 15 or 22 to 60, wherein the method for preparing the composite material comprises:

[0513] (1) providing a poly(ureaurethane) polymer, which comprises

[0514] (1.1) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0515] (1.2) contacting the prepolymer obtained in (1.1) with at least one secondary amine, the at least one secondary amine (iii) having the formula (I) as defined in any one of Examples 1 to 15;

[0516] or

[0517] (1.1’) reacting at least one isocyanate (i) with at least one secondary amine - the at least one secondary amine (iii) having the formula (I) as defined in any one of Examples 1 to 15 - to obtain a prepolymer;

[0518] (1.2’) contacting the prepolymer obtained in (1.1’) with at least one polyol (ii);

[0519] (2) contacting the polymer obtained in (1.2) or (1.2’) with a filler as defined in Example 54 or 55.

[0520] 62. The method according to Example 61, wherein (1) is carried out at a temperature in the range of 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, even more preferably in the range of 20 °C to 90 °C.

[0521] 63. The method according to Example 61 or 62, wherein one or more of (1) and (2), preferably (1) and (2), are carried out in the absence of a solvent.

[0522] 64. The method according to any one of Examples 61 to 63, wherein in (2), the contacting of the polymer with the filler is carried out by mixing or pressing.

[0523] 65. The method according to embodiment 64, wherein the pressing is carried out under a pressure in the range of 10 to 30 kN, preferably in the range of 15 to 25 kN, more preferably in the range of 18 to 22 kN.

[0524] 66. The method according to any one of embodiments 61 to 65, further comprising

[0525] (1.3) curing the polymer obtained in (1.2) or (1.2’) preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C;

[0526] or

[0527] (3) curing the polymer obtained in (2) preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C.

[0528] 67. A prepolymer obtainable or obtained by the method according to any one of embodiments 21 to 66.

[0529] 68. The prepolymer according to embodiment 67, wherein the prepolymer contains HUB.

[0530] 69. A poly(urea - urethane) polymer obtainable or obtained by the method according to any one of embodiments 21 to 66.

[0531] 70. Use of the prepolymer according to embodiment 67 or 68 for the preparation of a poly(urea - urethane) polymer.

[0532] 71. A poly(urea - urethane) polymer obtainable or obtained by a method of preparing the poly(urea - urethane) polymer by using the prepolymer according to embodiment 67.

[0533] In the context of the present invention, the term "alkylene" relates to an acyclic saturated hydrocarbon group, which may be an acyclic saturated hydrocarbon chain that combines different moieties, such as in C1 - C 30In the case of an alkylene group, it has 1 to 30 (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30) C atoms, or in the case of a C1-C5 alkylene group, it has 1 to 5 (i.e., 1, 2, 3, 4, or 5) C atoms. Representative examples of alkylene groups include, but are not limited to, -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH(CH2CH3)-, -CH2-CH2-CH(CH2CH3)-, -CH2-CH(n-C3H7)-, -CH2-CH(n-C4H9)-, -CH2-CH(n-C5H 11 )-, -CH2-CH(n-C6H 13 )-, -CH2-CH(n-C7H 15 )-, -CH2-CH(n-C8H 17 )-, -CH(CH3)-CH(CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-[C(CH3)2]2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, -(CH2) 10 -, -(CH2)7-, -(CH2)9-, -(CH2) 11 -, -(CH2) 12 -, -(CH2) 13 -, -(CH2) 14 -, -(CH2) 15 -, -(CH2) 16 -, -(CH2) 17 -, -(CH2) 18 -, -(CH2) 19 -, -(CH2) 20 -, -(CH2) 21 -, -(CH2) 22 -, -(CH2) 23 -, -(CH2) 24 -, -(CH2) 25 -, -(CH2) 26 -, -(CH2) 27 -, -(CH2) 28-, -(CH2) 29 - and -(CH2) 30 -.

[0534] In the context of the present invention, the term "heteroalkylene" relates to an alkylene as described above, in which one or more carbon atoms have been replaced by a heteroatom independently selected from the group consisting of oxygen, sulfur and nitrogen (-NH-). The heteroalkylene may preferably have 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen (-NH-), particularly preferably 1 heteroatom as one or more chain linkages. The heteroalkylene may preferably be 2 to 30 membered, particularly preferably 2 to 12 membered, very particularly preferably 2 or 6 membered. More preferably, oxygen (-O-) is the most preferred heteroatom in the "heteroalkylene". Representative examples of heteroalkylene include, but are not limited to, (-CH2-O-CH2-) 1-500 , (-CH2-O-CH(CH3)-) 1-500 , -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-O-CH(CH3)-, -CH2-O-CH(CH2CH3)-, -CH2-O-CH(n-C3H7)-, -CH2-O-CH(n-C4H9)-, -CH2-O-CH(n-C5H 11 ), -CH2-O-CH(n-C6H 13 ), -CH2-O-CH(n-C7H 15 ), -CH2-O-CH(n-C8H 17 ), -CHO-(CH3)-CHO-(CH3)-, -CO-(CH3)2-, -CH2-O-C(CH3)2-CH2-, -CH2-[O-C(CH3)2]2-CH2-, -(CH2)3-O-CH2-, -(CH2)4-O-CH2-, -(CH2)5-O-CH2-, -(CH2)6-O-CH2-, -(CH2)8-OCH2-, -(CH2) 10 -O-CH2-, -(CH2)7-O-CH2-, -(CH2)9-O-CH2-, -(CH2) 11 -O-CH2-, -(CH2) 12 -O-CH2-, -(CH2) 13 -O-CH2-, -(CH2) 14 -O-CH2-, -(CH2) 15 -O-CH2-, -(CH2) 16 -O-CH2-, -(CH2) 17-O-CH2-, -(CH2) 18 -O-CH2-, -(CH2) 19 -O-CH2-, -(CH2) 20 -O-CH2-, -(CH2) 21 -OCH2-, -(CH2) 22 -OCH2-, -(CH2) 23 -O-CH2-, -(CH2) 24 -OCH2-, -(CH2) 25 -OCH2-, -(CH2) 26 -OCH2-, -(CH2) 27 -O-CH2-, -(CH2) 28 -O-CH2-, -(CH2) 29 -O-CH2-, -(CH2) 30 -O-CH2-, -CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-NH-CH2-CH2-, -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -, where R x1 is -CH2-CH3 (where R y1 is [-O-CH2-CH(CH3)] n1 -NH-C d (R l )(R m )(R n), and wherein m1 + n1 + o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(wherein R y2 is [-O-CH2-CH(CH3)] n2 -NH-C d (R l )(R m )(R n ), and wherein m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O] o3 -CH2-CH(CH)3-(wherein n3 is in the range of 8 to 10 and m3 + o3 is in the range of 3 to 4, or wherein n3 is in the range of 12 to 13 and m3 + o3 is in the range of 5 to 7, or wherein n3 is in the range of 38 to 40 and m3 + o3 is in the range of 5 to 7), -[CH-CH2-O] m4 -CH2-CH2-(wherein m4 is in the range of 8 to 250), and -[CH2-CH2-NH] m5 -(wherein m5 is in the range of 10 to 100,000).

[0535] In the context of the present invention, the term "alkenylene" relates to acyclic unsaturated hydrocarbon groups having at least one double bond, preferably 1, 2 or 3 double bonds, and which may be branched or straight-chain and unsubstituted or at least monosubstituted, such as having 2 to 30 (i.e., 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30) C-atoms in the case of C2-C 30 alkenylene, more preferably C2-C 20 alkenylene, most preferably C2-C 10 alkenylene, and especially C2-C6 alkenylene. Representative examples of alkenylene include, but are not limited to, -CH=CH- and -CH2-CH=CH-.

[0536] In the context of the present invention, the term "heteroalkenylene" relates to an alkenylene as described above, wherein one or more carbon atoms have been replaced by heteroatoms each independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH). The heteroalkenylene may preferably have 1, 2, or 3 heteroatoms, particularly preferably 1 heteroatom, selected from the group consisting of oxygen, sulfur, and nitrogen (NH) as one or more chain linkages. The heteroalkenylene may preferably be 3- to 30-membered, particularly preferably 3- to 12-membered, very particularly preferably 3- or 6-membered. Representative examples of heteroalkenylene include, but are not limited to, -CH=CH-NH-, -CH=CH-O-, -CH=CH-CH2-O-, and -CH=CH-S-.

[0537] In the context of the present invention, it is conceivable that if one or more of the substituents represent an alkylene, alkenylene, heteroalkylene, or heteroalkenylene group or contain such a group that is mono- or polysubstituted, then the group is preferably substituted by 1, 2, 3, 4, or 5, particularly preferably by 1, 2, or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C 1-5 -alkyl)2, -NH-phenyl, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2, and -SO3H, wherein the above-mentioned -C 1-5 alkyl residue is in each case straight-chain or branched and the above-mentioned phenyl residue is unsubstituted or substituted by 1, 2, 3, 4, or 5, preferably by 1, 2, 3, or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F. It is contemplated that the alkylene, alkenylene, heteroalkylene and heteroalkenylene are each independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from the group consisting of phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -SH, -S-phenyl, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5), wherein the phenyl residue is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of F, Cl, Br, I, -OH, -SH, -NO2, -CN, -O-CH3, -O-CF3 and -O-C2H5.

[0538] In the context of the present invention, the term "cycloalkylene" relates to saturated cyclic hydrocarbon groups. C5-C 30 Representative examples of cycloalkylene include, but are not limited to, cyclopentylene (e.g., cyclopent-1,3-ylidene, cyclopent-1,2-ylidene), cyclohexylene (e.g., cyclohex-1,4-ylidene, cyclohex-1,3-ylidene and cyclohex-1,2-ylidene), cycloheptylene, cyclooctylene (e.g., 1,5-cyclooctylene),

[0539]

[0540] In the context of the present invention, the term "cycloalkylene" also relates to bridged cyclic hydrocarbon groups, such as cyclic hydrocarbon groups having 2 to 4 rings with 5 to 30 carbon atoms. Representative examples include, but are not limited to, norbornylene (e.g., 1,4-norbornylene and 2,5-norbornylene), norbornyl (e.g., 2,6-norbornyl) and adamantylene (e.g., 1,5-adamantylene and 2,6-adamantylene).

[0541] In the context of the present invention, the term "subheterocycloalkyl" also relates to a cyclic or polycyclic saturated divalent group having 5 to 30 ring members, wherein carbon atoms are replaced by 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S. Representative examples include, but are not limited to, 1,5-dioxaoctylene, 4,8-dioxabicyclo[3.3.0]octylene.

[0542] In the context of the present invention, the term "subcycloalkenyl" relates to a divalent cycloalkenyl ring structure, i.e., a cycloalkenyl having two single bonds as attachment points to other groups as defined herein. Representative examples of "subcycloalkenyl" include, but are not limited to, cyclopent-1,2-ene-3,5-ylidene, 3-cyclohexene-1,2-ylidene, 2,5-cyclohexadiene-1,4-ylidene, cyclohex-1,2-ene-3,5-ylidene, 2,5-cyclohexadiene-1,4-ylidene and cyclohept-1,2-ene-3,5-ylidene.

[0543] In the context of the present invention, the term "subheterocycloalkenyl" relates to a cyclic or polycyclic non-aromatic unsaturated divalent group having 5 to 30 carbon atoms (wherein carbon atoms are replaced by 1, 2 or 3 heteroatoms selected from N, O and S heteroatoms) and having 1, 2 or 3 double bonds.

[0544] In the context of the present invention, it is conceivable that if one or more of the substituents represent a monosubstituted or polysubstituted subcycloalkyl, subcycloalkenyl, subheterocycloalkyl and subheterocycloalkenyl, then the group is preferably substituted by 1, 2, 3, 4 or 5, particularly preferably by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C 1-5 -alkyl)2, -NH-phenyl, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein said -C 1-5 alkyl residue is straight-chain or branched in each case and said phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably by 1, 2, 3 or 4, substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F. It is conceivable that the alkylene, alkenylene, heteroalkylene and heteroalkenylene are independently of one another unsubstituted or substituted by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -SH, -S-phenyl, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5), wherein the phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -SH, -NO2, -CN, -O-CH3, -O-CF3 and -O-C2H5.

[0545] In the context of the present invention, the term "arylene" refers to a closed aromatic divalent ring or ring system, such as phenylene, naphthylene, biphenylene, fluorenylene and indenylene.

[0546] In the context of the present invention, the term "heteroarylene" refers to a closed aromatic divalent ring or ring system having at least one heteroatom selected from nitrogen, oxygen and sulfur. Representative examples of heteroarylene include, but are not limited to, furanylene, thienylene, pyridinylene, quinolinylene, isoquinolinylene, indolylene, isoindolylene, triazolylene, pyrrolylene, tetrazolylene, imidazolylene, pyrazolylene, oxazolylene, thiazolylene, benzofuranylene, benzothienylene, carbazolylene, benzoxazolylene, pyrimidinylene, benzimidazolylene, quinoxalinylene, benzothiazolylene, naphthyridinylene, isoxazolylene, isothiazolylene, purinylene, quinazolinylene, pyrazinylene, 1-oxo-pyridinylene, pyridazinylene, triazinylene (preferably one or more of linked-triazinylene, asymmetrical-triazinylene and symmetrical-triazinylene), tetrazinylene, oxadiazolylene and thiadiazolylene.

[0547] In the context of the present invention, it is conceivable that if one or more of the substituents represent a mono- or polysubstituted arylene and heteroarylene, this is preferably substituted by 1, 2, 3 or 4, particularly preferably by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C 1-5 -alkyl)2, -NH-phenyl, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein the above -C 1-5The alkyl residue is straight-chain or branched in each case and the above phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 -alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 -alkenyl, -C 2-5 -alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F. It is conceivable that the alkylene, alkenylene, heteroalkylene and heteroalkenylene are independently of one another unsubstituted or substituted by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -SH, -S-phenyl, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5), where the phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -SH, -NO2, -CN, -O-CH3, -O-CF3 and -O-C2H5.

[0548] In the context of the present invention, the term "alkyl" refers to an acyclic saturated hydrocarbon residue which can be branched or straight-chain and unsubstituted or at least monosubstituted, such as having 1 to 30 (i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30) C atoms in the case of C1-C 30 alkyl or having 1 to 5 (i.e. 1, 2, 3, 4 or 5) C atoms in the case of C1-C5 alkyl. In the context of the present invention, it is conceivable that if one or more of the substituents represent a monosubstituted or polysubstituted alkyl or contain a monosubstituted or polysubstituted alkyl, this is preferably substituted by 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3 substituents independently selected from the group consisting of: F, Cl, Br, I, -OH, -NO2, -CN, -SH, -NH2, -N(C 1-5 -alkyl)2, -N(C1-5 -(alkyl)(phenyl), -N(C 1-5 -(alkyl)(CH2-phenyl), -N(C 1-5 -(alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-)-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein said C 1-5 -alkyl residue is in each case straight-chain or branched and said phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2H5, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl. Particularly preferred substituents may be independently selected from the group consisting of: F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0549] In the context of the present invention, unsubstituted straight-chain C1-C 30Alkyl preferably refers to an alkyl selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl, and tetracosyl; more preferably selected from the group consisting of hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl, and tetracosyl; even more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; even more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; and even more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0550] In the context of the present invention, unsubstituted branched C1-C 30An alkyl group preferably refers to an alkyl group selected from the group consisting of isopropyl, isobutyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, neopentyl, 2-methyl-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, isohexyl, isoheptyl, 2,6-dimethyl-4-heptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, isoeicosyl, and 3-pinanyl-methyl, more preferably selected from the group consisting of 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, isoeicosyl, 2-methyltricosyl, 2-ethyldocosyl, 3-ethylheneicosyl, 3-ethyleicosyl, 4-propylheneicosyl, propylnonadecyl, 6-butyldodecyl, and 5-ethylundecyl. In the context of the present invention, a polysubstituted alkyl group should be understood as an alkyl group that is polysubstituted, preferably disubstituted or trisubstituted, on different or the same C atoms, for example, trisubstituted on the same C atom as in the case of -CF3, or at different positions as in the case of -(CHCl)-(CH2F). The polysubstitution can be carried out with the same or different substituents. Representative examples of substituents include, but are not limited to, -CH3, -CF3, -CF2H, -CFH2, -(CH2)-OH, -(CH2)-NH2, -(CH2)-CN, -(CH2)-(CF3), -(CH2)-(CHF2), -(CH2)-(CH2F), -(CH2)-(CH2)-O-CH3, -(CH2)-(CH2)-NH2, -(CH2)-(CH2)-CN, -(CF2)-(CF3), -(CH2)-(CH2)-(CF3), and -(CH2)-(CH2)-(CH2)-O-CH3.

[0551] In the context of the present invention, a substituted, straight-chain or branched C1-C 30 alkyl group also refers to a straight-chain or branched saturated hydrocarbon group having C1-C 30 carbon atoms substituted with a functional group selected from the group consisting of: F, Cl, Br, I, -OH, 2-furyl, -NO2, -CN, -SH, -NH2, -N(C 1-5 -alkyl)2, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-)-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein said C 1-5 -alkyl residue is in each case straight-chain or branched and said phenyl residue is preferably unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2H5, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl. Particularly preferred substituents may be independently selected from the group consisting of: F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0552] In the context of the present invention, the substituted, straight-chain or branched C1-C 30 alkyl also refers to having C1-C 30A branched or straight-chain saturated hydrocarbon group in which one carbon atom is substituted by a functional group selected from the group consisting of a hydroxyl group, an alkoxy group, C(=O)R, CN, and SR, and is preferably selected from the group consisting of: 1-methoxymethyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methoxybutyl, 2-hydroxy-butyl, 1-methoxypentyl, 1-methoxyhexyl, 1-methoxyheptyl, 1-methoxyoctyl, 1-methoxynonyl, decyl, 1-methoxyundecyl, 1-methoxydodecyl, 1-methoxytridecyl, 1-methoxytetradecyl, 1-methoxypentadecyl, 1-methoxyhexadecyl, 1-methoxyheptadecyl, 1-methoxyoctadecyl, 1-methoxynonadecyl, 1-methoxyicosyl, 1-methoxydocosyl, 1-methoxytetracosyl, 2-methoxypropyl, 2-methoxybutyl, 2-methoxypentyl, 2-methoxyhexyl, 2-methoxyheptyl, 2-methoxyoctyl, 2-methoxynonyl, decyl, 2-methoxyundecyl, 2-methoxydodecyl, 2-methoxytridecyl, 2-methoxytetradecyl, 2-methoxypentadecyl, 2-methoxyhexadecyl, 2-methoxyheptadecyl, 2-methoxyoctadecyl, 2-methoxynonadecyl, 2-methoxyicosyl, 2-methoxydocosyl, 2-methoxytetracosyl, 1-acetoxymethyl, 1-acetoxyethyl, 1-acetoxypropyl, 1-acetoxybutyl, 1-acetoxypentyl, 1-acetoxyhexyl, 1-acetoxyheptyl, 1-acetoxyoctyl, 1-acetoxynonyl, decyl, 1-acetoxyundecyl, 1-acetoxydodecyl, 1-acetoxytridecyl, 1-acetoxytetradecyl, 1-acetoxypentadecyl, 1-acetoxyhexadecyl, 1-acetoxyheptadecyl, 1-acetoxyoctadecyl, 1-acetoxynonadecyl, 1-acetoxyicosyl, 1-acetoxydocosyl, 1-acetoxytetracosyl, 1-cyanomethyl, 1-cyanoethyl, 1-cyanopropyl, 1-cyanobutyl, 1-cyanopentyl, 1-cyanohexyl, 1-cyanoheptyl, 1-cyanooctyl, 1-cyanononyl, decyl, 1-cyanoundecyl, 1-cyanododecyl, 1-cyanotridecyl, 1-cyanotetradecyl, 1-cyanopentadecyl, 1-cyanohexadecyl, 1-cyanoheptadecyl, 1-cyanooctadecyl, 1-cyanononadecyl, 1-cyanoicosyl, 1-cyanodocosyl, 1-cyanotetracosyl, 2-cyanopropyl, 2-cyanobutyl, 2-cyanopentyl, 2-cyanohexyl, 2-cyanoheptyl, 2-cyanooctyl, 2-cyanononyl, decyl, 2-cyanoundecyl,2-cyanododecyl, 2-cyanotridecyl, 2-cyanotetradecyl, 2-cyanopentadecyl, 2-cyanohexadecyl, 2-cyanoheptadecyl, 2-cyanooctadecyl, 2-cyanononadecyl, 2-cyanoeicosyl, 2-cyanounicosyl, 2-cyanodocosyl, 2-cyanotricosyl, 2-cyanotetracosyl, 1-sulfonylmethyl, 1-sulfonylethyl, 1-sulfonylpropyl, 1-sulfonylbutyl, 1-sulfonylpentyl, 1-sulfonylhexyl, 1-sulfonylheptyl, 1-sulfonyloctyl, 1-sulfonylnonyl, decyl, 1-sulfonylundecyl, 1-sulfonyldodecyl, 1-sulfonyltridecyl, 1-sulfonyltetradecyl, 1-sulfonylpentadecyl, 1-sulfonylhexadecyl, 1-sulfonylheptadecyl, 1-sulfonyloctadecyl, 1-sulfonylnonadecyl, 1-sulfonyleicosyl, 1-sulfonylunicosyl, 1-sulfonyldocosyl, 1-sulfonyltricosyl and 1-sulfonyltetracosyl.

[0553] In the context of the present invention, the term "alkenyl" refers to an unsubstituted, straight-chain C2-C 30 alkenyl. Representative examples of alkenyl include, but are not limited to, 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-eicosenyl and 2-eicosenyl, more preferably selected from 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-eicosenyl and 2-eicosenyl, 20-henicosenyl, 2-docosenyl, 6-tricosenyl and 2-tetracosenyl.

[0554] unsubstituted branched C2-C 30Representative examples of alkenyl groups include, but are not limited to, isopropenyl, isobutenyl, neopentenyl, 2-ethylhexenyl, 2-propylheptenyl, 2-butyl octenyl, 2-pentylnonenyl, 2-hexyldecenyl, isohexenyl, isoheptenyl, isooctenyl, isononenyl,isodecenyl, isododecenyl, isotetradecenyl, isohexadecenyl, isooctadecenyl, isoeicosanyl, 2-methyltricosanyl, 2-ethyldocosanyl, 3-ethylhenicosanyl, 3-ethyl eicosanyl, 4-propylhenicosanyl, 4-propylnonadecanyl, 6-butyldodecenyl, 5-ethylundecenyl, 1,4-hexadienyl, 1,3-hexadienyl, 2,5-hexadienyl, 3,5-hexadienyl, 2,4-hexadienyl, 1,3,5-hexatriene, 1,3,6-heptatriene, 1,4,7-octatriene or 2-methyl-1,3,5-hexatriene, 1,3,5,7-octatetraene, 1,3,5,8-nonatetraene, 1,4,7,10-undecatetraene, 2-ethyl-1,3,6,8-nonatetraene, 2-ethenyl-1,3,5,8-nonatetraene, 1,3,5,7,9-decapentaene, 1,4,6,8,10-undecapentaene and 1,4,6,9,11-dodecapentaene.

[0555] In the context of the present invention, a substituted, straight-chain or branched C2-C 30 alkenyl group means a straight-chain or branched unsaturated hydrocarbon group having C2-C 30 carbon atoms substituted with a functional group selected from: alkoxy, C(=O)R, CN and SR; where R is hydrogen, a substituted or unsubstituted straight-chain or branched C1-C 30 alkyl group, a substituted or unsubstituted straight-chain or branched C2-C 30 alkenyl group, a substituted or unsubstituted C5-C 30 cycloalkyl group, a substituted or unsubstituted C5-C 30 cycloalkenyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C7-C 30 arylalkyl group.

[0556] In the context of the present invention, the term "alkenyl" further means having C2-C 30A branched or straight-chain unsaturated hydrocarbon group in which one carbon atom is substituted with a functional group selected from the following: alkoxy, C(=O)R, CN, and SR; preferably selected from the group consisting of: 1-methoxyvinyl, 2-methoxypropenyl, 4-methoxybutenyl, 3-methoxypentenyl, 5-methoxyhexenyl, 2-methoxyheptenyl, 5-methoxyoctenyl, 3-methoxynonenyl, 6-methoxyundecenyl, 1-methoxydodec-2-enyl, 1-methoxytridec-5-enyl, 3-methoxytetradec-5-enyl, 3-methoxypentadec-12-enyl, 10-methoxyhexadec-15-enyl, 12-methoxyoctadec-16-enyl, 1-methoxyoctadec-3-enyl, 1-methoxynonadec-2-enyl, 1-methoxyeicos-20-enyl, 1-methoxydocos-2-enyl, 1-methoxydocos-4-enyl, 1-methoxytricos-22-enyl, 1-methoxytetracos-23-enyl, 2-methoxyprop-1-enyl, 2-methoxybut-1-enyl, 2-methoxypent-4-enyl, 2-methoxyhex-2-enyl, 2-methoxyhept-3-enyl, 2-methoxyoct-7-enyl, 2-methoxynon-5-enyl, 2-methoxyundec-10-enyl, 2-methoxydodec-4-enyl, 2-methoxytridec-12-enyl, 2-methoxytetradec-10-enyl, 2-methoxypentadec-14-enyl, 2-methoxyhexadec-1-enyl, 2-methoxyoctadec-12-enyl, 2-methoxynonadec-10-enyl, 2-methoxyeicos-18-enyl, 2-methoxydocos-2-enyl, 2-methoxydocos-3-enyl, 20-methoxytricos-2-enyl, 21-methoxytetracos-4-enyl, 1-acetoxyvinyl, 1-acetoxyprop-1-enyl, 1-acetoxybut-2-enyl, 1-acetoxypent-4-enyl, 1-acetoxyhex-2-enyl, 1-acetoxyhept-1-enyl, 1-acetoxyoct-7-enyl, 1-acetoxynon-2-enyl, 5-acetoxydec-3-enyl, 1-acetoxyundec-10-enyl, 1-acetoxydodec-2-enyl, 1-acetoxytridec-12-enyl, 10-acetoxytetradec-2-enyl, 15-acetoxypentadec-2-enyl, 10-acetoxyhexadec-2-enyl, 11-acetoxyoctadec-1-enyl, 13-acetoxyoctadec-2-enyl, 1-acetoxynonadec-14-enyl, 20-acetoxyeicos-19-enyl, 1-acetoxydocos-2-enyl, 1-acetoxydocos-10-enyl, 1-acetoxytricos-22-enyl, 1-acetoxytetracos-23-enyl, 1-cyanoeth-1-enyl, 1-cyanoprop-2-enyl,1-cyanobut-2-enyl, 1-cyanopent-3-enyl, 1-cyanohex-5-enyl, 1-cyanohept-6-enyl, 1-cyanooct-2-enyl, 1-cyanonon-3-enyl, 11-cyanoundec-2-enyl, 10-cyanododec-2-enyl, 10-cyanotridec-12-enyl, 1-cyanotetradec-3-enyl, 1-cyanopentadec-14-enyl, 1-cyanohexadec-15-enyl, 1-cyanoheptadec-2-enyl, 1-cyanooctadec-3-enyl, 1-cyanononadec-18-enyl, 1-cyanoeicos-10-enyl, 1-cyanodocos-20-enyl, 15-cyanodocos-3-enyl, 1-cyanotricos-20-enyl, 1-cyanotetracos-2-enyl, 2-cyanoprop-2-enyl, 2-cyanobut-1-enyl, 2-cyanopent-1-enyl, 2-cyanohex-3-enyl, 2-cyanohept-6-enyl, 2-cyanooct-1-enyl, 2-cyanonon-8-enyl, 2-cyanoundec-10-enyl, 2-cyanododec-1-enyl, 2-cyanotridec-12-enyl, 2-cyanotetradec-10-enyl, 2-cyanopentadec-3-enyl, 2-cyanohexadec-2-enyl, 2-cyanoheptadec-1-enyl, 2-cyanooctadec-12-enyl, 2-cyanononadec-15-enyl, 2-cyanoeicos-1-enyl, 2-cyanodocos-5-enyl, 2-cyanotricos-22-enyl, 2-cyanotetracos-20-enyl, 1-sulfinyleth-1-enyl, 1-sulfinylprop-2-enyl, 1-sulfinylbut-2-enyl, 1-sulfinylpent-4-enyl, 1-sulfinylhex-2-enyl, 1-sulfinylhept-5-enyl, 1-sulfinyloct-3-enyl, 1-sulfinylnon-5-enyl, 1-sulfinylundec-10-enyl, 1-sulfinyldodec-11-enyl, 1-sulfinyltridec-2-enyl, 1-sulfinyltetradec-4-enyl, 1-sulfinylpentadec-5-enyl, 1-sulfinylhexadec-3-enyl, 1-sulfinylheptadec-2-enyl, 1-sulfinyloctadec-3-enyl, 1-sulfinylnonadec-15-enyl, 1-sulfinyleicos-18-enyl, 1-sulfinylheneicos-20-enyl, 1-sulfinyldodecos-21-enyl, 1-sulfinyltricos-20-enyl and 1-sulfinyltetracos-22-enyl.

[0557] In the context of the present invention, the term "heteroalkyl" refers to an alkyl group in which one or more carbon atoms have each been independently replaced by a heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen (NH). The heteroalkyl preferably contains 1, 2, or 3 heteroatoms independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH) as one or more chain linkages. Additionally, the heteroalkyl can be 2- to 12-membered, preferably 2- to 6-membered.

[0558] In the context of the present invention, the term "heteroalkenyl" refers to an alkenyl group in which one or more carbon atoms have each been independently replaced by a heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen (NH). The heteroalkenyl preferably contains 1, 2, or 3 heteroatoms independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH) as one or more chain linkages. Additionally, the heteroalkenyl can be 3- to 12-membered, preferably 3- to 6-membered.

[0559] In the context of the present invention, the term "cycloalkyl" refers to monocyclic and bicyclic saturated alicyclic groups having 5 to 30 carbon atoms. Unsubstituted or branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkyls include, but are not limited to, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, and bicyclo[3.1.1]heptyl.

[0560] In the context of the present invention, C5-C 30 The monocyclic and bicyclic cycloalkyls can be further branched with one or more identical or different alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, neopentyl, etc. Branched C3-C 10 Representative examples of monocyclic and bicyclic cycloalkyls include, but are not limited to, methylcyclohexyl and dimethylcyclohexyl.

[0561] In the context of the present invention, the term "cycloalkenyl" refers to monocyclic and bicyclic unsaturated alicyclic groups having 5 to 30 carbon atoms, which contain one or more double bonds. C5-C 30 Representative examples of cycloalkenyls include, but are not limited to, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, or cyclodecenyl. These groups can be branched with one or more identical or different alkyl groups, preferably branched with methyl, ethyl, n-propyl, or isopropyl. Branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkenyls include, but are not limited to, methylcyclohexenyl and dimethylcyclohexenyl.

[0562] In the context of the present invention, the term "heterocycloalkyl" means a non-aromatic monocyclic or polycyclic ring containing 5 to 30 ring members, wherein at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S, and N. Representative examples of heterocycloalkyl include, but are not limited to, aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuryl, tetrahydrothienyl, tetrahydropyranyl, and pyranyl.

[0563] In the context of the present invention, the term "heterocycloalkenyl" refers to a non-aromatic unsaturated monocyclic or polycyclic ring containing 5 to 30 ring members (wherein at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S, and N) and having at least one double bond. Representative examples include, but are not limited to, (2,3)-dihydrofuryl, (2,3)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1,4)-dihydropyridin-1-yl, dihydropyranyl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 4,5-dihydropyrazol-2-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydrothienyl, and (1,2,3,4)-tetrahydropyridin-1-yl.

[0564] In the context of the present invention, it is conceivable that if one or more of the substituents represent a mono- or polysubstituted heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl, then the group is preferably substituted by 1, 2, 3, 4 or 5, particularly preferably by 1, 2 or 3 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -OH, -SH, -NH2, oxo(=O), thioxo(=S), -C(=O)-OH, C 1-5 alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -(CH2)-O-C 1-5 -alkyl, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)-C 1-5 -alkyl, -NH-C 1-5 -alkyl, N(C 1-5 alkyl)(C 1-5 -alkyl), -C(=O)-O-C 1-5 -alkyl, -C(=O)-H, -C(=O)-C 1-5 -alkyl, -CH2-O-C(=O)-phenyl, -O-C(=O)-phenyl, -NH-S(=O)2-C 1-5 -alkyl, -NH-C(=O)-C 1-5 -alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, pyrazolyl, phenyl, furyl / furanyl, thiadiazolyl, thiophenyl / thienyl and benzyl, where the above C 1-5 alkyl residues are in each case straight-chain or branched and the cyclic substituents or the cyclic residues of these substituents themselves are in each case unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably by 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -CF3, -OH, -NH2, -O-CF3, -SH, -O-C 1-5-alkyl, -O-phenyl, -O-CH2-phenyl, -(CH2)-O-C 1-5 -alkyl, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -C 1-5 alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -C(=O)-O-C 1-5 -alkyl and -C(=O)-CF3.

[0565] In the context of the present invention, the term "aryl" refers to an aromatic compound which may have more than one aromatic ring. Substituted and unsubstituted C6-C 30 Representative examples of aryl include, but are not limited to, phenyl, benzyl, cyclohexyl(phenyl)methyl, naphthyl, anthracenyl, tetraphenyl, phenalenyl, and phenanthryl.

[0566] In the context of the present invention, the term "heteroaryl" refers to a monocyclic or polycyclic, preferably monocyclic, bicyclic or tricyclic aromatic hydrocarbon residue having preferably 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 ring members, particularly preferably having 5, 6, 9, 10, 13 or 14 ring atoms, very particularly preferably having 5 or 6 ring members, wherein one or more carbon atoms as ring members have been replaced by heteroatoms each independently selected from the group consisting of oxygen, sulfur and nitrogen (NH). The heteroaryl may contain 1, 2, 3, 4 or 5, preferably 1, 2 or 3 heteroatoms each independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as one or more ring members. The heteroaryl may be unsubstituted or mono-substituted or identically or differently multi-substituted. Representative examples of heteroaryl include, but are not limited to, thienyl, furyl, pyrrolyl, pyrazolyl, pyrazinyl, pyranyl, triazolyl, pyridyl, imidazolyl, indolyl, isoindolyl, benzo[b]furyl, benzo[b]thienyl, benzo[d]thiazolyl, benzodiazolyl, benzotriazolyl, benzoxazolyl, benzoisoxazolyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridazinyl, pyrimidinyl, indazolyl, quinoxalinyl, quinazolinyl, quinolinyl, naphthyridinyl, and isoquinolinyl.

[0567] In the context of the present invention, an aryl or heteroaryl can be fused (anellated) to a monocyclic or bicyclic ring system. Representative examples of aryls fused to a monocyclic or bicyclic ring system include, but are not limited to, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, (2,3)-dihydro-1H-isoindolyl, (1,2,3,4)-tetrahydronaphthyl, (2,3)-dihydrobenzo[1.4]dioxinyl, benzo[1.3]dioxolyl, and (3,4)-dihydro-2H-benzo[1.4]oxazinyl.

[0568] In the context of the present invention, the term "arylalkyl" refers to an aryl ring attached to an alkyl chain. Representative examples of arylalkyls include, but are not limited to, 1-phenylmethyl, 1-phenylethyl, 1-phenylpropyl, 1-phenylbutyl, 1-methyl-1-phenylpropyl, 3-phenylpropyl, 4-phenylbutyl, 3-phenylbutyl, and 2-methyl-3-phenylpropyl.

[0569] In the context of the present invention, it is conceivable that if one or more of the substituents represent a mono- or polysubstituted aryl, heteroaryl, arylalkyl, or contain an aryl or heteroaryl, this can preferably be substituted by 1, 2, 3, 4, or 5, particularly preferably by 1, 2, or 3 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)-C 1-5 -alkyl, -NH-C 1-5 -alkyl, N(C 1-5 alkyl)2, -C(=O)-O-C 1-5 -alkyl, -C(=O)-H; -C(=O)-C 1-5 -alkyl, -CH2-O-C(=O)-phenyl, -O-C(=O)-phenyl, -NH-S(=O)2-C 1-5-alkyl, -NH-C(=O)-C 1-5 -alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, pyrazolyl, phenyl, furyl / furanyl, thiazolyl, thiadiazolyl, thiophenyl / thienyl, benzyl and phenethyl, wherein said C 1-5 alkyl residue is in each case straight-chain or branched and the cyclic substituents or the cyclic residues of these substituents themselves are unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably by 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5-alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F; most preferably, these substituents are each independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, neopentyl, vinyl, allyl, ethynyl, propargyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -CH2-O-CH3, -CH2-O-C2H5, -SH, -NH2, -C(=O)-OH, -S-CH3, -S-C2H5, -S(=O)-CH3, -S(=O)2-CH3, -S(=O)-C2H5, -S(=O)2-C2H5, -O-CH3, -O-C2H5, -O-C3H7, -O-C(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, pyrazolyl, phenyl, -N(CH3)2, -N(C2H5)2, -NH-CH3, -NH-C2H5, -CH2-O-C(=O)-phenyl, -NH-S(=O)2-CH3, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-C(CH3)3, -C(=O)-H, -C(=O)-CH3, -C(=O)-C2H5, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -O-C(=O)-phenyl, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, phenyl, furyl / furanyl, thiadiazolyl, thiophenyl / thienyl and benzyl,wherein the cyclic substituent or the cyclic residue of these substituents themselves is in each case unsubstituted or substituted by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, neopentyl, vinyl, allyl, ethynyl, propargyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -CH2-O-CH3, -CH2-O-C2H5, -S-CH3, -S-C2H5, -S(=O)-CH3, -S(=O)2-CH3, -S(=O)-C2H5, -S(=O)2-C2H5, -O-CH3, -O-C2H5, -O-C3H7, -O-C(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, and -S-CH2F.,

[0570] In the context of the present invention, the substituted aryl may be selected from the group consisting of: 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-aminophenyl, 3-aminophenyl, 4-aminophenyl, 2-dimethylaminophenyl, 3-dimethylaminophenyl, 4-dimethylaminophenyl, 2-methylaminophenyl, 3-methylaminophenyl, 4-methylaminophenyl, 2-acetylphenyl, 3-acetylphenyl, 4-acetylphenyl, 2-methylsulfinylphenyl, 3-methylsulfinylphenyl, 4-methylsulfinylphenyl, 2-methylsulfonylphenyl, 3-methylsulfonylphenyl, 4-methylsulfonylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 2-fluoromethylphenyl, 3-fluoromethylphenyl, 4-fluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-tert-butylphenyl, 3-tert-butylphenyl, 4-tert-butylphenyl, 2-carboxyphenyl, 3-carboxyphenyl, 4-carboxyphenyl, 2-vinylphenyl, 3-vinylphenyl, 4-vinylphenyl, 2-ethynylphenyl, 3-ethynylphenyl, 4-ethynylphenyl, 2-allylphenyl, 3-allylphenyl, 4-allylphenyl,2-trimethylsilylethynylphenyl, 3-trimethylsilylethynylphenyl, 4-trimethylsilylethynylphenyl, 2-formylphenyl, 3-formylphenyl, 4-formylphenyl, 2-acetamidophenyl, 3-acetamidophenyl, 4-acetamidophenyl, 2-dimethylaminocarbonylphenyl, 3-dimethylaminocarbonylphenyl, 4-dimethylaminocarbonylphenyl, 2-methoxymethylphenyl, 3-methoxymethylphenyl, 4-methoxymethylphenyl, 2-ethoxymethylphenyl, 3-ethoxymethylphenyl, 4-ethoxymethylphenyl, 2-aminocarbonylphenyl, 3-aminocarbonylphenyl, 4-aminocarbonylphenyl, 2-methylaminocarbonylphenyl, 3-methylaminocarbonylphenyl, 4-methylaminocarbonylphenyl, 2-carboxymethylesterphenyl, 3-carboxymethylesterphenyl, 4-carboxymethylesterphenyl, 2-carboxyethylesterphenyl, 3-carboxyethylesterphenyl, 4-carboxyethylesterphenyl, 2-carboxy-tert-butylesterphenyl, 3-carboxy-tert-butylesterphenyl, 4-carboxy-tert-butylesterphenyl, 2-methylsulfanylphenyl, 3-methylsulfanylphenyl, 4-methylsulfanylphenyl, 2-ethylsulfanylphenyl, 3-ethylsulfanylphenyl, 4-ethylsulfanylphenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoro-methoxyphenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-4-methylphenyl, (2,3)-difluorophenyl, (2,3)-dimethylphenyl, (2,3)-dichlorophenyl, 3-fluoro-2-trifluoro-methylphenyl, (2,4)-dichlorophenyl, (2,4)-difluorophenyl, 4-fluoro-2-trifluoromethylphenyl, (2,4)-dimethoxyphenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-nitrophenyl, 2-chloro-4-methylphenyl, 2-chloro-5-trifluoromethylphenyl, 2-chloro-5-methoxyphenyl, 2-bromo-5-trifluoromethylphenyl, 2-bromo-5-methoxyphenyl, (2,4)-dibromophenyl, (2,4)-dimethylphenyl, 2-fluoro-4-trifluoromethylphenyl, (2,5)-difluorophenyl, 2-fluoro-5-trifluoro-methylphenyl, 5-fluoro-2-trifluoromethylphenyl, 5-chloro-2-trifluoromethylphenyl, 5-bromo-2-trifluoromethylphenyl, (2,5)-dimethoxyphenyl, (2,5)-bis-trifluoromethylphenyl, (2,5)-dichlorophenyl, (2,5)-dibromophenyl, 2-methoxy-5-nitrophenyl, 2-fluoro-6-trifluoro-methylphenyl, (2,6)-dimethoxyphenyl, (2,6)-dimethylphenyl, (2,6)-dichlorophenyl, 2-chloro-6-fluorophenyl, 2-bromo-6-chlorophenyl, 2-bromo-6-fluorophenyl, (2,6)-difluorophenyl, (2,6)-difluoro-3-methylphenyl, (2,6)-dibromophenyl, (2,6)-dichlorophenyl, 3-chloro-2-fluorophenyl,3-chloro-5-methylphenyl, (3,4)-dichlorophenyl, (3,4)-dimethylphenyl, 3-methyl-4-methoxyphenyl, 4-chloro-3-nitrophenyl, (3,4)-dimethoxyphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-fluoro-4-trifluoromethylphenyl, (3,4)-difluorophenyl, 3-cyano-4-fluorophenyl, 3-cyano-4-methylphenyl, 3-cyano-4-methoxyphenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-methylphenyl, 3-bromo-4-methoxyphenyl, 4-chloro-2-fluorophenyl, 4-chloro-3-trifluoromethyl, 4-bromo-3-methylphenyl, 4-bromo-5-methylphenyl, 3-chloro-4-fluorophenyl, 4-fluoro-3-nitrophenyl, 4-bromo-3-nitrophenyl, (3,4)-dibromophenyl, 4-chloro-3-methylphenyl, 4-bromo-3-methylphenyl, 4-fluoro-3-methylphenyl, 3-fluoro-4-methylphenyl, 3-fluoro-5-methylphenyl, 2-fluoro-3-methylphenyl, 4-methyl-3-nitrophenyl, (3,5)-dimethoxyphenyl, (3,5)-dimethylphenyl, (3,5)-bis-trifluoromethylphenyl, (3,5)-difluorophenyl, (3,5)-dinitrophenyl, (3,5)-dichlorophenyl, 3-fluoro-5-trifluoromethylphenyl, 5-fluoro-3-trifluoro-methylphenyl, (3,5)-dibromophenyl, 5-chloro-4-fluorophenyl, 5-chloro-4-fluorophenyl, 5-bromo-4-methylphenyl, (2,3,4)-trifluorophenyl, (2,3,4)-trichlorophenyl, (2,3,6)-trifluorophenyl, 5-chloro-2-methoxyphenyl, (2,3)-difluoro-4-methyl, (2,4,5)-trifluorophenyl, (2,4,5)-trichlorophenyl, (2,4)-dichloro-5-fluorophenyl, (2,4,6)-trichlorophenyl, (2,4,6)-trimethylphenyl, (2,4,6)-trifluorophenyl, (2,4,6)-trimethoxyphenyl, (3,4,5)-trimethoxyphenyl, (2,3,4,5)-tetrafluorophenyl, 4-methoxy-(2,3,6)-trimethylphenyl, 4-methoxy-(2,3,6)-trimethylphenyl, 4-chloro-2,5-dimethylphenyl, 2-chloro-6-fluoro-3-methylphenyl, 6-chloro-2-fluoro-3-methyl, (2,4,6)-trimethylphenyl and (2,3,4,5,6)-pentafluorophenyl.,

[0571] In the context of the present invention, examples of substituted heteroaryl groups are 3-methylpyridin-2-yl, 4-methylpyridin-2-yl, 5-methylpyridin-2-yl, 6-methylpyridin-2-yl, 2-methylpyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, 6-methylpyridin-3-yl, 2-methylpyridin-4-yl, 3-methylpyridin-4-yl, 3-fluoropyridin-2-yl, 4-fluoropyridin-2-yl, 5-fluoropyridin-2-yl, 6-fluoropyridin-2-yl, 3-chloropyridin-2-yl, 4-chloropyridin-2-yl, 5-chloropyridin-2-yl, 6-chloropyridin-2-yl, 3-trifluoromethylpyridin-2-yl, 4-trifluoromethylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 6-trifluoromethylpyridin-2-yl, 3-methoxypyridin-2-yl, 4-methoxypyridin-2-yl, 5-methoxypyridin-2-yl, 6-methoxypyridin-2-yl, 4-methylthiazol-2-yl, 5-methylthiazol-2-yl, 4-trifluoromethylthiazol-2-yl, 5-trifluoromethylthiazol-2-yl, 4-chlorothiazol-2-yl, 5-chlorothiazol-2-yl, 4-bromothiazol-2-yl, 5-bromothiazol-2-yl, 4-fluorothiazol-2-yl, 5-fluorothiazol-2-yl, 4-cyanothiazol-2-yl, 5-cyanothiazol-2-yl, 4-methoxythiazol-2-yl, 5-methoxythiazol-2-yl, 4-methyloxazol-2-yl, 5-methyloxazol-2-yl, 4-trifluoromethyloxazol-2-yl, 5-trifluoromethyloxazol-2-yl, 4-chlorooxazol-2-yl, 5-chlorooxazol-2-yl, 4-bromooxazol-2-yl, 5-bromooxazol-2-yl, 4-fluorooxazol-2-yl, 5-fluorooxazol-2-yl, 4-cyanooxazol-2-yl, 5-cyanooxazol-2-yl, 4-methoxyoxazol-2-yl, 5-methoxyoxazol-2-yl, 2-methyl-(1,2,4)-thiadiazol-5-yl, 2-trifluoromethyl-(1,2,4)-thiadiazol-5-yl, 2-chloro-(1,2,4)-thiadiazol-5-yl, 2-fluoro-(1,2,4)-thiadiazol-5-yl, 2-methoxy-(1,2,4)-thiadiazol-5-yl, 2-cyano-(1,2,4)-thiadiazol-5-yl, 2-methyl-(1,2,4)-oxadiazol-5-yl, 2-trifluoromethyl-(1,2,4)-oxadiazol-5-yl, 2-chloro-(1,2,4)-oxadiazol-5-yl, 2-fluoro-(1,2,4)-oxadiazol-5-yl, 2-methoxy-(1,2,4)-oxadiazol-5-yl and 2-cyano-(1,2,4)-oxadiazol-5-yl.

[0572] In the context of the present invention, the term "substituted" for any of the alkylene, heteroalkylene, alkenylene, heteroalkenylene, cycloalkylene, heterocycloalkylene, cycloalkenylene, heterocycloalkenylene, arylene, and heteroarylene disclosed herein refers respectively to mono- or poly-substituted alkylene, heteroalkylene, alkenylene, heteroalkenylene, cycloalkylene, heterocycloalkylene, cycloalkenylene, heterocycloalkenylene, arylene, and heteroarylene, which may preferably be substituted with 1, 2, 3, 4 or 5, more preferably with 1, 2 or 3 substituents. Examples of substituents are -NHR 1 , where R 1 is -C(R u )(R v )(R w ), where R u , R v and R w are independently of one another selected from the group consisting of hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl. More preferably, R u , R v and R w are independently of one another selected from the group consisting of hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. More preferably, R u , R v and R wEach is independently selected from the group consisting of: hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-alkyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of: hydrogen, methyl and ethyl, more preferably selected from the group consisting of: hydrogen, methyl and ethyl. Alternatively, preferably, in -NHR 1 wherein R 1 is -C(R u )(R v )(R w ), wherein C and R u form a substituted or unsubstituted C6-C 30 arylene, and no R v and R w are both. For example, -NHR 1 can be -NH-Ph.

[0573] In the context of the present invention, for -Z 12 -, -N(R f )- means that the N atom is bonded to an R of the formula f which is bonded to Ca, thereby forming a heterocycle.

[0574] In the context of the present invention, a reversible NCO bond designates a bond between N (from a secondary hindered amine) of a urea group that can be reversibly formed and broken and C of (NCO).

[0575] In the context of the present invention, a "thermosetting polymer" refers to a network polymer comprising a covalently bonded structure having at least three covalent bond attachment points between polymer chains, wherein preferably these at least three covalent bond attachment points between polymer chains form part of a polymer network.

[0576] In the context of the present invention, a "thermoplastic polymer" refers to a linear polymer comprising a covalently bonded structure having two covalent bond attachment points between polymer chains, wherein preferably these two covalent bond attachment points between polymer chains form part of a linear polymer system.

[0577] In the context of the present invention, isocyanate is a general term for molecules containing at least one isocyanate functional group. Thus, the term "at least one isocyanate" is interpreted to cover one or more monoisocyanates, one or more diisocyanates, one or more triisocyanates, one or more tetra-isocyanates and one or more isocyanates having a higher number of isocyanate functional groups, such as polymers having one or more isocyanate functional groups. In the context of the present invention, examples of isocyanates are polymethylene polyphenyl isocyanates, commonly also referred to as pMDI.

[0578] The present invention can be further explained and illustrated based on the following examples. However, it will be understood that these examples are included for illustrative purposes only and are not intended to limit the scope of the present invention in any way.

[0579] Examples

[0580] Materials

[0581] polyTHF (commercial product from BASF): polytetrahydrofuran (polytetramethylene ether glycol) (functionality = 2; average molecular weight Mn = 2000 g / mol, OH = 56 mg KOH / g).

[0582] MDI: 4,4'-methylenebis(phenyl isocyanate) purchased from BASF Polyurethanes GmbH

[0583] BDO: 1,4-butanediol purchased from Alfa Aesar

[0584] DIBIS: diethylene glycol bischloroformate purchased from BASF Polyurethanes GmbH

[0585] Benzoyl chloride purchased from Sigma Aldrich

[0586] TDI, a mixture of 80% 2,4- and 20% 2,6-toluene diisocyanate, purchased from BASF

[0587] pMDI (product of BASF): polymeric diphenylmethane diisocyanate

[0588] DIB-MDA: 4,4'-methylenebis(N-sec-butylaniline) purchased from abcr

[0589] DIB-polyetheramine T403 prepared from polyetheramine T403 purchased from BASF

[0590] Polyol 1 = trifunctional polyether polyol and mainly contains secondary hydroxyl groups - functionality = 3, Mn = 3500 g / mol, OH = 48 mg KOH / g, viscosity (25 °C) = 600 mPa.s.

[0591] Polyol 2 = glycerol-based trifunctional polyether polyol - functionality = 3, Mn = 420 g / mol, OH = 400 mg KOH / g, viscosity (25 °C) = 373 mPa.s

[0592] Polymer type TP: thermoplastic

[0593] Polymer type TS: thermosetting plastic

[0594] Analysis methods

[0595] Content of NCO

[0596] The content of NCO is determined according to ISO DIN EN ISO 14896 (Modell 916TI-Touch, Metrohm).

[0597] Melting point

[0598] A sample of the polyurethane urea is cut into cubes with dimensions of 0.2 × 0.2 × 0.2 cm 3 and transferred to a hot press. A pressure of 20 kN is applied to the sample for at least 5 minutes, and the temperature is increased at a rate of XX. When a distinct phase transition of the solid polymer occurs, the melting point is determined.

[0599] Thermogravimetric analysis (TGA)

[0600] The TGA spectrum is obtained in a gold crucible under a N2 atmosphere according to ISO 11358.

[0601] DSC measurement

[0602] According to ASTM D 3418, DSC analysis of a sample of approximately 5 - 10 mg is performed using a DSC model Q20 of TA Instruments.

[0603] Determination of the soluble fraction

[0604] A 500 - gram sample of the polyurethane urea is cut into cubes with dimensions of 0.5 × 0.5 × 0.5 cm 3

[0605] ​The sample was allowed to swell in THF at room temperature for 24 h. Subsequently, the excess THF was removed. The swollen sample was weighed (m(swollen)). The sample was first dried under ambient conditions and then under vacuum at 65 °C to remove the absorbed THF. Finally, the mass of the dried sample (m(dried)) was evaluated. The swelling ratio and the insoluble fraction were determined via the following equations:

[0606] Swelling ratio = [m(swollen) - m(dried)] / m(dried)

[0607] Insoluble fraction = m(dried) / m(dried)

[0608] Table 1 Overview

[0609]

[0610]

[0611] Unless otherwise stated, the ratios given in the examples refer to molar ratios.

[0612] Reference Example 1A: Preparation of the prepolymer

[0613] 100 g of 4,4′-methylenebis(phenyl isocyanate) (mMDI) (0.400 mol) was placed in a flask under N2. The mixture was heated. When the MDI was molten, 0.02 g of benzoyl chloride (141 μmol) was added. 233 g of polytetrahydrofuran (polyTHF) (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the mixture containing mMDI at 80 °C. When the NCO value reached <8% (ratio NCO:OH approximately 1:0.3), the reaction was terminated by cooling. The prepolymer 1a was obtained as a colorless, slightly opaque liquid.

[0614] Reference Example 1B: Preparation of the prepolymer

[0615] 17.4 g of toluene diisocyanate (TDI) (0.100 mol) was placed in a flask under N2. The mixture was heated to 80 °C and 0.008 g of diglycol dicarbonate (DIBIS) (35 μmol) was added. 62 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the TDI mixture at 80 °C. When the NCO value reached <8% (ratio NCO:OH ~ 1:0.3), the reaction was terminated by cooling. The prepolymer 1b was obtained as a colorless, slightly opaque liquid.

[0616] Reference Example 1C: Preparation of Prepolymer

[0617] 34.0 g of polymeric diphenylmethane diisocyanate (pMDI) (0.100 mol) and 8 mg of DIBIS (35 μmol) were mixed. 75.0 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the pMDI-containing mixture at 80 °C. When the NCO value reached <8% (the ratio of NCO:OH was approximately 1:0.25), the reaction was terminated by cooling. Prepolymer 1c was obtained as a slightly brownish, slightly opaque liquid.

[0618] Reference Example 1D: Preparation of Prepolymer

[0619] 20.0 g of mMDI (0.060 mol) was added to 20.0 g of pMDI (0.080 mol) and 8 mg of DIBIS (35 μmol). 77.5 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the mMDI / pMDI-containing mixture at 80 °C. When the NCO value reached <8% (the ratio of NCO:OH was approximately 1:0.3), the reaction was terminated by cooling. A prepolymer was obtained as a slightly brownish, slightly opaque liquid.

[0620] Reference Example 2: Preparation of Prepolymer

[0621] 75.0 g of MDI (0.300 mol) was placed in a flask and purged with N2. It was heated to 80 °C, and a mixture of 188 g of polyol 1 (a trifunctional polyether polyol with propylene oxide (PO) end groups and secondary hydroxyl groups, functionality = 3, M n = 3500 g / mol, hydroxyl value = 48 mg KOH / g, viscosity (25 °C) = 600 mPa*s) and 0.008 g of DIBIS (35 μmol) was slowly added at 80 °C. When the NCO value reached <8% (the ratio of NCO:OH was approximately 1:0.3), the reaction was terminated by cooling. Prepolymer 2 was obtained as a colorless, slightly opaque liquid.

[0622] Reference Example 3: Preparation of DIB-Polyetheramine T403

[0623] In the presence of a palladium catalyst (Pd / Ag on alumina, having a major θ content, based on alumina, having 0.3 wt.-% Pd, 0.1 wt.-% Ag, EM distribution is eggshell, catalyst purchased from BASF - such a catalyst is described in WO 2006 / 040159 A1) (17.75 g, 14.06 wt%), 100 g (0.21 mol, 1 equivalent) of polyetheramine T403 and 26.6 g of butan-2-one (0.36 mol, 1.7 equivalents) were charged into a 300 mL steel pressure autoclave. The autoclave was sealed, purged with nitrogen and heated to 140 °C at atmospheric pressure. Subsequently, the autoclave was pressurized with H2 (160 bar) at the same temperature for 20 h. The autoclave was cooled and vented. The crude compound was filtered, and the volatiles and water were removed under reduced pressure to obtain 98 g of a colorless, transparent liquid, which was used without any further purification.

[0624] Comparative Example 1A: Preparation of a poly(urea-carbamate) polymer according to the prior art and testing of its recyclability

[0625] 60.0 g of prepolymer 1a (7.94% NCO) obtained according to Reference Example 1A was heated to 70 °C, degassed and placed under N2. 4.67 g of 1,4-butanediol (BDO) (51.8 mmol) (ratio NCO:OH 1.00:1.00 to 1.05:1.00) was added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 40 min. A material in the form of a white opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0626] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 min. The samples started to melt at about 110 °C to 120 °C and formed cookie-shaped plates after cooling. Further tests are disclosed in Examples 9 and 10 below.

[0627] Example 1A: Preparation of a covalent adaptable system (CAS) poly(urea-carbamate) polymer according to the invention and testing of its recyclability

[0628] 60.0 g of prepolymer 1a (7.94% NCO) obtained according to Reference Example 1A was heated to 70 °C, degassed and placed under N2. 16.1 g of 4,4'-methylene-bis[N-(1-methylpropyl)-phenylamine] (DIB-MDA) (51.8 mmol) (ratio NCO:NH 1.00:1.00 to 1.05:1.00) was added and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The obtained mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 40 min. A material in the form of a yellow transparent solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0629] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 20 kN was applied to the samples and pressed for at least 5 min. The samples started to melt at about 70 °C and formed thin foils after cooling. Further tests are disclosed in Examples 9 and 10 below.

[0630] Conclusion: The product obtained according to the invention starts to melt at a temperature of about 70 °C, far below that of Comparative Example 1A, and allows the formation of thin foils - which are recyclable.

[0631] Comparative Example 1B: Preparation of a poly(ureaurethane) polymer according to the prior art

[0632] 30.0 g of prepolymer 1b (7.47% NCO) obtained according to Reference Example 1B was heated to 70 °C, degassed and placed under N2. 2.29 g of 1,4-butanediol (BDO) (25.4 mmol) (ratio NCO:OH 1.00:1.00 to 1.05:1.00) was added and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 16 h. A material in the form of a colorless transparent viscoelastic plate was obtained, which showed already flow at room temperature. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0633] Example 1B: Preparation of a covalent adaptable system (CAS) poly(ureaurethane) polymer according to the invention

[0634] 30.0 g of prepolymer 1b (7.47% NCO) according to Reference Example 1B was heated to 70 °C, degassed and placed under N2. 8.39 g of DIB-MDA (25.4 mmol) (ratio NCO:NH 1.00:1.00 to 1.05:1.00) was added and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with release foil and cured in an oven at 105 °C for 40 min. A material in the form of a yellow transparent viscoelastic plate was obtained, which was shown to be already flowable at room temperature. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0635] Comparative Example 1C: Preparation of a poly(ureaurethane) polymer according to the prior art and its recyclability test

[0636] 30.0 g of prepolymer 1c (7.15% NCO) according to Reference Example 1C was mixed with 2.19 g of BDO (24.2 mmol) (ratio NCO:OH 1.05:1.00) and stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with release foil and cured in an oven at 105 °C for 90 min. A material in the form of a slightly brown opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0637] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 min. The samples did not melt at temperatures up to 180 °C.

[0638] Example 1C: Preparation of a covalently adaptable network (CAN) poly(ureaurethane) polymer according to the invention and its recyclability test

[0639] 30.0 g of prepolymer 1c (7.15% NCO) according to Reference Example 1C was mixed with 8.03 g of DIB-MDA (24.2 mmol) (ratio NCO:OH 1.05:1.00) and stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with release foil and cured in an oven at 105 °C for 90 min. A material in the form of a slightly brown opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0640] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3), and transfer it to a hot press. Apply a pressure of 20 kN to the sample and press for at least 5 minutes. The sample starts to melt at about 160 °C and forms a thin foil after cooling.

[0641] Conclusion: Contrary to Comparative Example 1C, the product obtained according to the present invention can be melted and allows the formation of a thin foil - which is recyclable.

[0642] Comparative Example 1D: Preparation of a poly(urea - urethane) polymer according to the prior art and its recyclability test

[0643] Mix 25.0 g of prepolymer 1d (7.85% NCO) obtained according to Reference Example 1D with 2.00 g of BDO (22.2 mmol) (NCO:OH ratio 1.05:1.00) and stir in a high - speed mixer at 2000 rpm for 20 seconds. Cast the mixture into a silicone rubber mold lined with a separating foil and cure in an oven at 105 °C for 90 min. A material in the form of an off - white opaque solid plate is obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0644] Recyclability test (melting). Cut a sample of the obtained plate into small cubes (about 0.2×0.2×0.2 cm 3 ), and transfer it to a hot press. Apply a pressure of 20 kN to the sample and press for at least 5 minutes. The sample does not melt at temperatures up to 180 °C.

[0645] Example 1D: Preparation of a covalent adaptable network (CAN) poly(urea - urethane) polymer according to the present invention and its recyclability test

[0646] Mix 25.0 g of prepolymer 1d (7.85% NCO) obtained according to Reference Example 1D with 7.35 g of DIB - MDA (22.2 mmol) (NCO:OH ratio 1.05:1.00) and stir in a high - speed mixer at 2000 rpm for 20 seconds. Cast the mixture into a silicone rubber mold lined with a separating foil and cure in an oven at 105 °C for 90 min. A material in the form of a yellowish slightly opaque solid plate is obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0647] Recyclability test (melting). Cut a sample of the obtained plate into small cubes (about 0.2×0.2×0.2 cm 3 ), and transfer it to a hot press. Apply a pressure of 20 kN to the sample and press for at least 5 minutes. The sample starts to melt at about 140 °C and forms a thin foil after cooling.

[0648] Conclusion: Contrary to Comparative Example 1D, the product obtained according to the present invention can be melted and allows the formation of thin foils - which are recyclable.

[0649] Comparative Example 2: Preparation of a poly(urea - urethane) polymer according to the prior art and testing of its recyclability

[0650] 30.0 g of prepolymer 2 (7.50% NCO) obtained according to Reference Example 2 and 2.30 g of BDO (25.3 mmol) (the ratio of NCO:OH is 1.00:1.00 to 1.05:1.00) were added, and the mixture was stirred in a high - speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a white opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0651] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), and they were transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 minutes. The samples did not melt at temperatures up to 180 °C.

[0652] Recyclability test (extrusion). To test the extrusion characteristics, samples of the obtained plate were cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), and they were transferred to an extruder. The samples were extruded at 200 °C, and they did not melt, and the material clogged the extruder. When the extrusion chamber was opened, the material was regained as a brittle solid.

[0653] Example 2: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the present invention and testing of its recyclability

[0654] 30.0 g of prepolymer 2 (7.50% NCO) obtained according to Reference Example 2 and 8.43 g of DIB - MDA (25.5 mmol) (the ratio of NCO:NH 1.00:1.00 to 1.05:1.00) were added, and the mixture was stirred in a high - speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0655] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (approx. 0.2×0.2×0.2 cm 3) Transfer it to a hot press. Apply a pressure of 20 kN to the sample and press for at least 5 minutes. The sample starts to melt at about 100 °C and forms a thin foil after cooling.

[0656] Conclusion: Contrary to Comparative Example 2, the product obtained according to the present invention can be melted and allows the formation of a thin foil - which is recyclable.

[0657] Recyclability test (extrusion). To test the extrusion properties, cut a sample of the obtained plate into small cubes (about 0.2 × 0.2 × 0.2 cm 3 ) and transfer it to an extruder. Extrude the sample at 180 °C. At this temperature, the sample can be extruded into a uniform, flowable paste with a maximum torque of 2.2 kN.

[0658] Conclusion: Contrary to Comparative Example 2, the product obtained according to the present invention can be extruded and allows the formation of a uniform paste - which is recyclable.

[0659] Comparative Example 3: Preparation of a poly(urea - urethane) polymer according to the prior art

[0660] Add 60.0 g of prepolymer 1a (7.43% NCO) obtained according to Reference Example 1A and 14.15 g of polyol 2 (functionality = 3, M n = 400 g / mol, hydroxyl value = 400 mg KOH / g) (the ratio of NCO:OH is 1.05:1.00), and stir the mixture in a high - speed mixer at 2000 rpm for 20 seconds. Cast the mixture into a silicone rubber mold lined with a separating foil and cure it in an oven at 105 °C for 90 min. A material in the form of a slightly yellow transparent solid plate is obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0661] Recyclability test (melting). Cut a sample of the obtained plate into small cubes (about 0.2 × 0.2 × 0.2 cm 3 ) and transfer it to a hot press. Apply a pressure of 20 kN to the sample and press for at least 5 minutes. The sample does not melt at temperatures up to 180 °C.

[0662] Example 3: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the present invention

[0663] Add 60.0 g of prepolymer 1a (7.50% NCO) obtained according to Reference Example 1A and 21.1 g of DIB - polyetheramine T403 prepared as described in Reference Example 3 (sec - butyl - modified polyetheramine T403, functionality = 3, M n= 600 g / mol, amine value = 270 mg KOH / g) (the ratio of NCO:NH is 1.05:1.00), and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0664] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ), and they were transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 minutes. The samples started to melt at about 100 °C and formed thin foils after cooling.

[0665] Conclusion: Contrary to Comparative Example 3, the product obtained according to the present invention can be melted and allows the formation of thin foils - it is recyclable.

[0666] Table 2 Characteristics / recyclability of the prepared materials

[0667]

[0668] Example 4: Preparation of a composite material according to the present invention containing glass fibers

[0669] 30.0 g of prepolymer 2 (6.87% NCO) obtained according to Reference Example 2 was heated to 70 °C, degassed, and placed under N2. 7.26 g of DIB-MDA (51.8 mmol) (ratio NCO:NH 1.05:1.00) was added. The mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. Subsequently, 300 mg of single glass fibers were stirred in as a filler material. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 40 min. A material in the form of a yellow opaque plate was obtained.

[0670] Example 5: Mechanical recycling

[0671] The material obtained from Example 4 was cut and pressed at 140 °C under a pressure of 20 kN for at least 5 minutes. As a result, thin foils were obtained, indicating that the composite material is mechanically recyclable.

[0672] Example 6: Mechanical recycling test of a composite material according to the present invention

[0673] Samples of the yellow opaque solid plates obtained according to Example 2 were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3), and transfer it to a hot press. Press the sample at 140 °C under a pressure of 20 kN for at least 5 minutes to obtain a thin foil. Place a single glass fiber between two foils, and press the structure at 140 °C under a pressure of 20 kN for at least 5 minutes to obtain a composite material in the form of a thin foil.

[0674] Recycling test: Cut the obtained composite material in the form of a thin foil into pieces, and press these pieces at 140 °C under a pressure of 20 kN for at least 5 minutes. As a result, a thin foil is obtained, showing that the composite material is mechanically recyclable.

[0675] Example 7: Chemical recycling of the composite material according to the present invention

[0676] Immerse 22.0 g of the composite material according to Example 4 in 150 mL of dry toluene and heat it to reflux with stirring. After 4 h, before the resin is completely dissolved, the material begins to swell. When the solution cools, the mixture undergoes a sol-gel transition, which is reversible when heated again. Then, filter the dissolved gel hot and filter out the glass fiber.

[0677] Collect the filtrate in a flask. Gel the filtrate and dry it first in a rotary evaporator at 120 °C and 50 mbar under reduced pressure at an elevated temperature, and then dry it in a vacuum oven at 80 °C.

[0678] Press the obtained solid at 140 °C under a pressure of 20 kN for at least 5 minutes to obtain a thin foil. Place a single glass fiber between two foils, and press the structure at 140 °C under a pressure of 20 kN for at least 5 minutes to obtain a new composite material from the recycled polymer. The chemical recycling according to Example 7 is shown in Figure 3 in.

[0679] Example 8: Chemical recycling in the presence of an amine

[0680] Approximately 5 g of the bulk material (poly(ureaurethane) polymer) obtained according to Example 2 was immersed in 50 mL of toluene. 2.6 g of DIB-MDA (1 equivalent relative to the reversible NCO bonds) was added to scavenge the opened NCO-bonds formed by the thermal cleavage of the urethane bonds. After stirring for 16 h under reflux, the material was completely dissolved. The toluene was removed under reduced pressure to obtain a mixture containing the amine-terminated prepolymer as an uncured viscous liquid. The mixture was diluted with 1 mL of toluene, and the amine-terminated prepolymer was precipitated by adding it to 50 g of n-heptane to remove the excess DIB-MDA. The amine-terminated prepolymer was separated from the solvent and the dissolved DIB-MDA therein by decantation. Then the amine-terminated prepolymer was dried to obtain 4.51 g of an amine (DIB-MDA)-terminated prepolymer having an amine value of 75.2 mg KOH / g.

[0681] Formation of new poly(ureaurethane) polymer (bulk material): The amine (DIB-MDA)-terminated prepolymer was reacted with the prepolymer of Example 2 to obtain a recycled covalent adaptable network (CAN) poly(urea-urethane) polymer, which is the same material as the bulk material (poly(ureaurethane) polymer) obtained according to Example 2.

[0682] Example 9: Testing - Recycling properties of the polymers obtained in Example 1A and Comparative Example 1A

[0683] The plates obtained according to Example 1A and Comparative Example 1A were cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ).

[0684] 19.1 Approximately 5 g of a sample of the material according to Example 1A was mixed with 50 mL of toluene and heated under reflux for 16 h. Then the mixture was cooled. The CAS material according to Example 1A was completely dissolved in toluene, such that a homogeneous slightly yellow liquid mixture was obtained. After removing the solvent, a transparent slightly yellow solid was obtained.

[0685] 19.2 Approximately 5 g of a sample of the material according to Comparative Example 1A was mixed with 50 mL of toluene and heated under reflux for 16 h. Then the mixture was cooled. The material did not dissolve.

[0686] This example is shown in Figure 1 . Thus, it has been demonstrated by this example that, contrary to the materials of the prior art, the CAS materials according to the invention are reversibly soluble in toluene, allowing their chemical recycling.

[0687] Example 10: Testing - Melting behavior of the polymers obtained in Example 1A and Comparative Example 1A

[0688] The materials obtained in Example 1A and Comparative Example 1A were cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), transferred to a hot press, and then subjected to compression molding in the hot press at 20 kN for 5 minutes at different temperatures (i.e., 80 °C, 100 °C, and 120 °C). The products obtained are shown in Figure 2 .

[0689] In the case of the material of Example 1A, a foil was obtained at 80 °C, while for the material of the comparative example, it remained as a white block at 80 °C and even 100 °C. At 120 °C, a fine white opaque plate was formed for the comparative example, while a fine transparent foil was obtained for the example of the present invention. Thus, it is shown that the material according to the present invention melts at a much lower temperature compared to common materials.

[0690] Example 11: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the present invention from an aliphatic diamine

[0691] 60.0 g of Reference Example 2 (7.50% NCO) and 9.44 g of DIB - butanediamine (N,N’ - di - sec - butyl - 1,4 - butanediamine) (47.1 mmol) (NCO:NH ratio 1.05:1.00) were added, and the mixture was stirred in a high - speed mixer at 2000 rpm for 20 seconds. The mixture immediately became solid and was cured at 105 °C for 1 h and at room temperature for 48 h to obtain an off - white opaque material.

[0692] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (0.2×0.2×0.2 cm 3 ), which were transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 minutes. The samples started to melt at about 100 °C and formed circular plates after cooling.

[0693] Recyclability test (solution, toluene). 2 g of the plates obtained from the melting test were cut into small cubes (0.2×0.2×0.2 cm 3 ) and immersed in 20 mL of toluene. The mixture was heated to 110 °C for 24 h. The samples did not dissolve.

[0694] Recyclability test (solution, DMI). 2 g of the obtained plates were cut into small cubes (0.2×0.2×0.2 cm3) and immersed in 20 mL of 1,3 - dimethyl - 2 - imidazolidinone. The mixture was heated to 130 °C for 24 h. The samples completely dissolved to obtain a clear solution.

[0695] Higher temperatures are required to recycle the polymers containing aliphatic amines according to the invention by dissolving them in an organic solvent.

[0696] Reference Example 4: Preparation of the prepolymer

[0697] 20 g of 4,4′-methylene-bis-(phenyl isocyanate) (MDI) (0.080 mol) and 20 g of polymeric MDI (pMDI, average functionality of about 2.5) (0.06 mol) were placed in a flask and placed under N2. The mixture was heated and when the MDI melted, 0.02 g of benzoyl chloride (141 μmol) was added. 82.6 g of polytetrahydrofuran (polyTHF) (f = 2, M n = 2000 g / mol, #OH = 55 mg KOH / g) was melted and slowly added to the MDI / pMDI mixture at 80 °C. When the NCO value reached <8% (the ratio NCO:OH was about 1:0.3), the reaction was terminated by cooling. A prepolymer in the form of a yellow clear liquid was obtained.

[0698] Example 12: Preparation of a covalently adaptable network (CAN) poly(ureaurethane) polymer according to the invention from N-(2-hydroxyethyl)aniline

[0699] 15.0 g of the prepolymer according to Reference Example 4 (7.3% NCO) and 1.70 g of N-(2-hydroxyethyl)aniline (12.4 mmol) (ratio NCO:XH 1.05:1.00, X = sum of O and N) were added and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained.

[0700] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 minutes. The samples started to melt at about 180 °C and formed cookie-shaped plates after cooling.

[0701] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 110 °C. The samples dissolved completely, but a turbid solution was obtained.

[0702] Recyclability test (solution, DMI). 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm3 ) and immersed in 30 mL of 1,3-dimethyl-2-imidazolidinone. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 120 °C. The sample was completely dissolved after 1 h to obtain a clear solution.

[0703] Example 13: Preparation of a covalently adaptable network (CAN) poly(ureaurethane) polymer according to the invention from 2-(ethylamino)ethanol

[0704] 15.0 g of the prepolymer according to Reference Example 4 (7.3% NCO) and 1.10 g of 2-(ethylamino)ethanol (12.8 mmol) (ratio NCO:XH 1.05:1.00, X = sum of O and N) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained.

[0705] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 min. The samples started to melt at about 150 °C and formed cookie-shaped plates after cooling.

[0706] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 110 °C. The sample did not dissolve but swelled.

[0707] Recyclability test (solution, DMI). 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 30 mL of 1,3-dimethyl-2-imidazolidinone. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 120 °C. The sample was completely dissolved after 4 h to obtain a clear solution.

[0708] Comparative Example 14: Preparation of a covalently adaptable network (CAN) poly(ureaurethane) polymer from 1,4-butanediol

[0709] 15.0 g of the prepolymer according to Reference Example 4 (7.3% NCO) and 1.12 g of 1,4-butanediol (12.4 mmol) (ratio NCO:XH 1.05:1.00, X = O) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained.

[0710] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ), and transferred to a hot press. A pressure of 20 kN was applied to the samples for at least 5 minutes. The samples did not melt at temperatures up to 180 °C.

[0711] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ), and immersed in 13 mL of toluene. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 110 °C. The sample did not dissolve.

[0712] Recyclability test (solution, DMI). 1 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ), and immersed in 10 mL of 1,3-dimethyl-2-imidazolidinone. 0.33 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 120 °C. The sample did not dissolve after 7 h, and the sample swelled in the solvent.

[0713] Comparative Example 15: Prepared according to WO 2022189242

[0714] 16.5 g of pMDI was dissolved in THF and cooled to 0 °C. With stirring, DIB-MDA (20.23 g) in THF was added dropwise to the pMDI / THF solution. The reaction mixture was stirred at 0 °C for 1 h, and then slowly heated to reflux for 6 h. The solvent was removed, and the sample was cured at 140 °C for 24 h. Product 15a in the form of a yellow solid was obtained.

[0715] Recyclability test (solution, toluene). 3 g of the solid 15a was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ), and immersed in 30 mL of toluene. The mixture was heated to 110 °C for 4 h. The sample did not dissolve.

[0716] Immerse 3 g of plate 15a in 30 mL of toluene and add 0.9 g of 1,4 - butanediol (2.00 equivalents of OH butanediol / equivalent of HUB in the plate). Stir the mixture under reflux for 24 h. After this time, the material swells but does not dissolve.

[0717] Cut 3 g of 15a into pieces and immerse in a small amount of toluene (5 mL), add 0.4 g of diisopropylamine. Heat the mixture under reflux for 8 h. The cube dissolves and a yellow liquid is obtained.

[0718] Immerse 3 g of plate 15a in 30 mL of toluene and add 0.4 g of DIB - MDA (0.25 equivalents of secondary hindered amine DIB - MDA / equivalent of HUB in the plate). Stir the mixture under reflux overnight. When cooled, the mixture does not gel. When the solvent is removed, a viscous liquid that is still soluble in THF is obtained.

[0719] Recycling Example 1: Recycling via scavenger molecule / prepolymer

[0720] Preparation of prepolymer 2:

[0721] Immerse 75.0 g of MDI (0.300 mol) in a flask and place under N2. Heat the mixture to 80 °C, and slowly add a mixture of 188 g of Lupranol 2074 (a triol polyol with propylene oxide (PO) end - caps, generating secondary hydroxyl groups, f = 3, Mn = 3500 g / mol, #OH = 48 mg KOH / g, viscosity (25 °C) = 600 mPa*s) and 0.008 g of diglycol - bis - chloroformate (DIBIS) (35 μmol) to the MDI mixture at 80 °C. When the NCO value reaches <8% (ratio NCO:OH ∼ 1:0.3), terminate the reaction by cooling. A prepolymer in the form of a colorless, slightly opaque liquid is obtained.

[0722] Preparation of CAN 2

[0723] Add 30.0 g of prepolymer 2 (7.50% NCO) and 8.43 g of DIB - MDA (25.5 mmol) (ratio NCO:NH 1.00:1.00 - 1.05:1.00), and stir the mixture in a high - speed mixer at 2000 rpm for 20 s. Cast the mixture into a silicone rubber mold lined with a release foil and cure in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate is obtained.

[0724] Recycling Example 2: Without scavenger molecule

[0725] Immerse 22 g of plate CAN 2 into 100 mL of toluene. Heat the mixture to reflux for 24 h to completely dissolve the plate in toluene. Keep the solution at room temperature without stirring to gel the mixture upon cooling. When the solvent is removed from the gel, a solid is obtained.

[0726] Recycling Example 3: In the case of DIB-MDA

[0727] Immerse 5 g of plate CAN 2 into 50 mL of toluene and add 1.0 g / 0.5 g / 0.3 g of DIB-MDA (0.8 / 0.4 / 0.25 equivalents of SHA DIB-MDA / equivalent SHU in the plate). Stir the mixture overnight under reflux. When cooled, the mixture does not gel. When the solvent is removed, a viscous liquid that is still soluble in THF is obtained.

[0728] Recycling Example 4: Recycling CAN 2 by ring-closing with DIB-MDA

[0729] Immerse 26 g of plate CAN 2 into 250 mL of toluene having 13.3 g of DIB / MDA (2 equivalents of SHA DIB-MDA / equivalent SHU in the plate). Dissolve the plate under stirring at reflux overnight. Then remove the toluene and dilute the liquid prepolymer with 10 g of THF. To remove the unreacted DIB-MDA, precipitate the prepolymer into 250 mL of n-heptane.

[0730] Dry the prepolymer and determine the amine value (53.2 mg KOH / g).

[0731] Mix 10 g of the prepolymer obtained from CAN2 with the corresponding amount of freshly prepared prepolymer 2 (5.7 g, NCO = 7.0%) at 1400 Upm for 20 s and cure at 105 °C for 1 h.

[0732] Analyze the recycled polymer via IR and match it with the original polymer.

[0733] The recycled polymer shows recyclability again via mechanical recycling (compression molding at 140 °C, 20 kN, 5 min) and chemical recycling by complete dissolution in hot toluene.

[0734] Recycling Example 5: In the case of diol

[0735] Immerse 5 g of plate CAN 2 in 50 mL of toluene and add 0.6 g / 0.3 g / 0.15 g / 0.076 g / 0.048 g of 1,4 - butanediol (2.00 / 1.00 / 0.50 / 0.25 / 0.125 equivalents of OH of butanediol / equivalent of SHU in the plate). Stir the mixture under reflux overnight. When cooled, the mixture did not gel. When the solvent was removed, a viscous liquid that was still soluble in THF was obtained.

[0736] Recycling Example 6: In the case of isocyanates

[0737] Immerse 5 g of plate CAN 2 in 50 mL of toluene and add 1.61 g of MDI (2.00 equivalents of NCO of MDI / equivalent of SHU in the plate). Stir the mixture under reflux overnight. When cooled, the mixture did not gel. When the solvent was removed, a viscous liquid that was still soluble in THF was obtained.

[0738] Recycling Example 7: Recycling via volatile monoamine

[0739] Proof of concept:

[0740] In the absence of diisopropylamine:

[0741] Cut 3 g of CAN 2 into pieces and immerse in a small amount of toluene (5 mL). Heat the mixture under reflux for 8 h. Since there was little solvent diffusion, the pieces did not dissolve. Instead, they swelled in the solvent.

[0742] In the case of diisopropylamine:

[0743] Cut 3 g of CAN 2 into pieces and immerse in a small amount of toluene (5 mL). Add 0.4 g of diisopropylamine. Heat the mixture under reflux for 8 h. The cubes dissolved and a yellow liquid was obtained.

[0744] When the solvent was removed, the prepolymer remained liquid.

[0745] Prepolymer 1a:

[0746] Immerse 100 g of 4,4′ - methylene - bis - (phenyl isocyanate) (MDI) (0.400 mol) in a flask and place under N2. Heat the mixture. When MDI melted, add 0.02 g of benzoyl chloride (141 μmol). Melt 233 g of polytetrahydrofuran (polyTHF) (f = 2, M n = 2000 g / mol, #OH = 55 mg KOH / g) and slowly add it to the MDI mixture at 80 °C. When the NCO value reached <8% (ratio NCO:OH ∼ 1:0.3), terminate the reaction by cooling. A prepolymer in the form of a colorless, slightly opaque liquid was obtained.

[0747] Amine-terminated polymer 1a - DiPA:

[0748] 5.1 g of prepolymer 1a was mixed with 0.90 g of diisopropylamine (DiPA) and cured at 105 °C for 40 min to obtain a yellow waxy thermoplastic. The thermoplastic was analyzed by NMR spectroscopy and NCO titration. The reversible reaction was demonstrated by heating the polymer under vacuum (20 mbar) at different temperatures and analyzing the NMR spectra and NCO values.

[0749]

[0750] *The amine peak at an NMR ratio of 1.31 relative to the polyol peaks at 1.80 - 1.50, normalized to the original 1a - DiPA

[0751]

[0752]

[0753] Recycling Example 8: Recycling of CAN 2 by ring - closing with diisopropylamine

[0754] 7.8 g of CAN 2 was immersed in 15.6 g of diisopropylamine. The mixture was heated to 80 °C for 24 h. The network became liquid and a separate phase formed under the excess amine. A part (1.6 g) of the polymer phase was dried at 80 °C under 20 mbar to remove the excess amine. An intermediate prepolymer (0.62 g) in the form of a viscous liquid was obtained. The polymer did not have a network structure as it was soluble in a small amount of THF (1 g), indicating depolymerization to a thermoplastic system.

[0755] The intermediate prepolymer was used to produce recycled CAN 2. The reactive amine was removed by heating the prepolymer to 170 °C under 20 mbar for 1 h. The polymer was re - obtained as a solid material of 540 mg. The network structure could be confirmed by adding THF (1 g). The sample did not dissolve but swelled. Description of the Drawings

[0756] Figure 1 Shows different steps related to the recycling characteristics test of the plates obtained in Comparative Example 1A and Example 1A. 1. Shredding / cutting; 2. Addition of toluene; 3. Heating for 16 h, followed by cooling; 4. Removal of toluene.

[0757] Figure 2 Shows the test results after compression molding of Example 1A and Comparative Example 1A at different temperatures. The arrows show that in the comparative example, only small pieces were obtained at 80 °C and 100 °C, indicating no melting at these temperatures, while a foil was already obtained at 80 °C with the material of Example 1A.

[0758] Figure 3 Shows different steps related to the tests of the recycling characteristics of the plates obtained in Comparative Example 2 and Example 2. 1. Shredding / cutting; 2. Addition of toluene; heating for 16 h, followed by cooling;

[0759] Figure 4 Shows the test results after compression molding of Example 2 and Comparative Example 2 at different temperatures. Comparative Example 2 did not melt at all at temperatures up to 180 °C, while Example 2 melted at about 130 °C

[0760] Figure 5 Shows different steps related to the tests of the recycling characteristics of the composite material of Example 4. 1. Add toluene to the block of the composite material of Example 4 and heat under reflux for 16 h; 2. Hot filtration; a: Separated glass fibers, b: Gelatinize and dry the filtrate; 3. Press b at 140 °C under 20 kN for 5 min to obtain a thin foil, 4. Recycled composite material with glass fibers obtained by pressing glass fibers between two foils.

[0761] Cited literature

[0762] Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes], 3rd edition, 1993, Chapters 3.1, 3.2 and 3.3.2, Carl Hanser Verlag

[0763] Ullmann’s Encyclopedia of Industrial Chemistry, 4th edition, Volume 19, pages 62 to 65

[0764] WO 2006 / 040159 A1

Claims

1. A method for recycling a composition comprising a poly(ureaurethane) polymer (PUU1), the method comprising step (i): (i) Treating the composition comprising the poly(ureaurethane) polymer (PUU1) under conditions suitable for at least partially cleaving the urethane bonds of the polymer to obtain a mixture (M1) containing prepolymers, The poly(ureaurethane) polymer (PUU1) is obtainable or obtained by a method comprising: - Reacting the following components: (i) At least one isocyanate; (ii) At least one polyol; and (iii) At least one secondary amine having the following formula (I): where -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; where -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene; -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 subcycloalkenyl; -Z8- is a substituted or unsubstituted 5- to 30-membered hetero-subcycloalkenyl; -Z9- is a substituted or unsubstituted C6-C 30 subaryl; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroaryl; -Z 11 - is a C6-C substituted by -NHR or -OR 30 subaryl, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 10 alkyl; -Z 12 - is -N(R f )-; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkyl, where at least one of one or more heteroatoms of Z 13 comes from X a ; where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom; where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b being NH, the corresponding C a and / or C b is a C atom; where (A) R c , R d , R f and R g are each independently selected from the group consisting of hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl, R b and R e are each independently as defined for R c 、R d 、R f and R g ; or There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a 、C b 、X a 、X b and R a ; or (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both; or (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; or -C b and R bForm a substituted or unsubstituted C6-C 30 arylene, and without R c and R d both; wherein, When C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in (A) below; Wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A) below.

2. The method according to claim 1, wherein, Step (i) is a treatment at a temperature in the range of 60 °C to 200 °C and at a pressure in the range of 1 bar to 200 bar or in the range of 50 mbar to 1 bar.

3. The method according to claim 1 or 2, wherein, In step (i), an aprotic solvent is added.

4. The method according to any one of claims 1 to 3, wherein, In step (i), a component (S) suitable for reacting with the free functional groups of the cleaved urea bonds is added.

5. The method according to claim 4, wherein, Component (S) is selected from the group consisting of: polyols, diols, polyisocyanates, diisocyanates, polyamines, oligamines, diamines and amines of general formula (II).

6. The method according to claim 5, wherein, Component (S) is a polyamine, an oligamine or a diamine of general formula (I).

7. The method according to any one of claims 1 to 6, wherein, The composition comprises a filler selected from the group consisting of: glass fibres, carbon fibres, mineral fibres, textiles, wire meshes, metal fibres, metal rods, carbonates, wood and mixtures of two or more thereof.

8. The method according to any one of claims 1 to 7, wherein, The method comprises step (ii) (ii) separating the components of the mixture obtained in step (i).

9. The method according to claim 8, wherein, Step (ii) comprises a filtration step.

10. The method according to any one of claims 8 or 9, wherein, The method comprises step (iii) (iii) preparing a poly(urea - urethane) polymer using one or more of the components obtained in step (ii).

11. A prepolymer obtained or obtainable by the method according to any one of claims 1 to 10.

12. A poly(urea - urethane) polymer obtained or obtainable by the method according to any one of claims 1 to 10.

13. Use of the prepolymer according to claim 11 for the preparation of a poly(urea - urethane) polymer.

14. A poly(urea - urethane) polymer obtained or obtainable by a method of preparing a poly(urea - urethane) polymer by using the prepolymer according to claim 11.

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