Polyurea copolymer

Abstract

The invention relates to a polyurea copolymer, which is obtained by the reaction of an isocyanate mixture with at least one secondary amine having at least two amine functions; wherein the isocyanate mixture (A) has an average NCO functionality of ≥ 2.10.

Description

Invention Field

[0001] The present invention relates to a polyurea copolymer obtained by reacting an isocyanate mixture with at least one secondary amine having at least two amine functional groups; wherein the isocyanate mixture (A) has an average NCO functionality of ≥2.10. Background of the Invention

[0003] Materials and polymer science requires the development of polymeric materials with desired performance characteristics for use, as well as those exhibiting flexibility, repairability, and reprogrammable shape. There is also a need to develop such polymers that can degrade or reversibly depolymerize. While shape memory and self-healing polymers are known, many of these polymers lack the desired properties and dynamic characteristics. For example, many shape memory polymers that rely on covalent crosslinking cannot be processed, reprogrammed, or recycled once a permanent shape has been formed through covalent crosslinking. As for degradable or reversibly depolymerizable polymers, these polymers often lack the desired performance characteristics for use and are either too easily degraded or, on the other hand, not degrade as easily or rapidly as expected.

[0004] Unlike polymers with strong, irreversible covalent bonds and stable bulk properties, polymers prepared through reversible non-covalent interactions or covalent bonds exhibit a variety of dynamic properties. The dynamic characteristics of reversible polymers have been used to design self-healing, shape-memory, and environmentally adaptable materials. However, non-covalent interactions are relatively weak, with only a few exceptions, such as quadruple hydrogen bonds, high-valence metal chelates, and host-guest molecule interactions. Conversely, dynamic covalent bonds typically possess higher strength and more controllable reversibility.

[0005] Theoretically, introducing a large substituent creates steric hindrance, disrupting the orbital coplanarity of the amide bond. This reduces the conjugation effect, thus weakening the carbonyl-amine interaction. However, the dissociation intermediate from amide decomposition is an enone, and if formed, it is typically too reactive to provide for the dynamic reversible formation of the amide bond. For the carbonyl-amine structure to be reversible, the dissociated carbonyl structure must be stable under ambient conditions but still highly reactive with the amine. One such functional group that satisfies these requirements is the isocyanate group, which can be used to form urea linkages. Isocyanates are generally stable enough under ambient conditions and react rapidly with amines to form urea bonds, a reaction widely used in the synthesis of polyureas and poly(urethane-urea). Therefore, controlling the reversibility and kinetics of these urea bonds in polymer materials is crucial.

[0006] Polymers can be formed by the reaction of one or more isocyanates with one or more amines. These polymers can be formed by contacting the isocyanate with the amine using static mixing equipment, high-pressure impact mixing equipment, low-pressure mixing equipment, rollers with mixing attachments, and simple manual mixing techniques. These polymers can be used in grouts, adhesives, sealants, coatings, foams, and many other applications. Specific examples include, but are not limited to, truck bed liners, concrete coatings, and moldings.

[0007] US 2007 / 0208156A1 discloses polyureas, polyurethanes, and polyurea-polyurethane hybrids prepared from isocyanates, secondary polyetheramines, secondary amines, and optionally polyols. Secondary polyetheramines can be used in combination with secondary amines to modify other properties of the polymer, including its curing time and cost. Secondary polyetheramines include secondary polyoxyethylene amines.

[0008] US 2016 / 0030254A1 discloses a reversible polymer formed from polyurea by modifying nitrogen atoms with sterically hindered substituents. The reversibility of the hindered urea bond is controlled by changing the volume of the substituents. Choosing hindered urea polymers with high binding constants and short lifetimes allows for the design of reversible and self-healing polymer materials at mild temperatures without external stimuli.

[0009] US 2017 / 327627A1 discloses a stretchable, repairable, and reprogrammable shape memory polymer with hindered urea bonds.

[0010] The aforementioned prior art all results in the formation of linear polyurea polymers with dynamic bonds. However, additional reactants such as polyols are required to form cross-linked three-dimensional polymers, which does not provide structural uniformity. Therefore, the object of the present invention is to provide a polyurea polymer with a uniform three-dimensional network structure, which is prepared from polyamines and polyisocyanates without the use of any additional reactants such as polyols, but still possesses dynamic bonds.

[0011] Another object of the present invention is to provide a recyclable three-dimensional network polyurea copolymer. Invention Overview

[0013] The objective is achieved by reacting an isocyanate mixture (A) having an average NCO functionality of ≥2.10 with at least one secondary amine (B) having at least two secondary amine functionalities.

[0014] Therefore, in a first aspect, the present invention relates to a polyurea copolymer obtained by reacting a reaction mixture comprising the following components:

[0015] a. Isocyanate mixture (A); and

[0016] b. At least one secondary amine of formula (B)

[0017]

[0018] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered sub-hetero-alkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylenes, 5-30 membered heterocyclic alkylenes, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heterocyclic alkenylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkylene, substituted or unsubstituted C2-C 30 Alkenyl 5-30 membered heterocyclic alkylene, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 aryl and substituted or unsubstituted C2-C 30 Alkenyl 5-30 quinone heteroaryl,

[0019] R b R c R d R e R f and R g Independently selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30 Alkenyl groups, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic alkyl, substituted or unsubstituted 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 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 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0020] R b and R e And the carbon atoms they are bonded to, or

[0021] R c and R f And the carbon atoms they are bonded to, or

[0022] R d and R g And the carbon atoms they are bonded to, or

[0023] R c and R d And the carbon atoms they are bonded to, or

[0024] R c and R b And the carbon atoms they are bonded to, or

[0025] R b and R dAnd the carbon atoms they are bonded to, or

[0026] R f and R e And the carbon atoms they are bonded to, or

[0027] R e and R g And the carbon atoms they are bonded to, or

[0028] R f and R g and the carbon atoms they are bonded to

[0029] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and

[0030] The isocyanate mixture (A) has an average NCO functionality of ≥2.10.

[0031] In a second aspect, the present invention relates to a method for preparing a polyurea copolymer, comprising at least the following steps:

[0032] i) Provide an isocyanate mixture (A) with an average NCO functionality ≥ 2.10;

[0033] ii) Provide at least one secondary amine of formula (B):

[0034]

[0035] Where R a R b R c R d R e R f and R g The definition is as follows:

[0036] iii) Make (A) and (B) come into contact.

[0037] In a third aspect, the present invention relates to an article comprising a polyurea copolymer.

[0038] In a fourth aspect, the present invention relates to a method for reshaping a polyurea copolymer, comprising at least the following steps:

[0039] a) Applying pressure and heat to the polyurea copolymer as described herein to obtain a heated polyurea copolymer; and

[0040] b) Molding the heated polyurea copolymer from step a). Invention Details

[0042] Before describing the compositions and formulations of the present invention, it should be understood that the invention is not limited to the specific compositions and formulations described, as such compositions and formulations can certainly vary. It should also be understood that the terminology used herein is not intended to be limiting, as the scope of the invention is limited only by the appended claims.

[0043] If a group is defined below as comprising at least a certain number of embodiments, this means that it also includes a group preferably consisting only of these embodiments. Furthermore, the terms “first,” “second,” “third,” or “a,” “b,” “c,” etc., in the specification and claims are used to distinguish similar elements and are not necessarily used to describe a sequence or temporal order. It should be understood that the terms thus used are interchangeable where appropriate, and embodiments of the invention described herein can operate in orders other than those described or illustrated herein. The terms “first,” “second,” “third,” or “(A),” “(B),” and “(C),” or “(a),” “(b),” “(c),” “(d),” “i,” “ii,” etc., relate to steps of a method or use or measurement where there is no temporal or time interval coherence between the steps; that is, the steps may be performed simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between such steps, unless otherwise stated in this application as described above or below.

[0044] Furthermore, the ranges defined throughout the specification include end values; that is, the range of 1-10 means that both 1 and 10 are included in this range. For the avoidance of doubt, the applicant is entitled to any equivalent scheme in accordance with applicable law.

[0045] The various aspects of the invention are defined in more detail in the following paragraphs. Each aspect thus defined may be combined with any other one or more aspects unless expressly indicated to the contrary. In particular, any feature indicated as preferred or advantageous may be combined with any other one or more features indicated as preferred or advantageous.

[0046] Throughout this specification, references to "one embodiment" or "implementation" mean that a particular feature, structure, or characteristic described in connection with that embodiment is included in at least one embodiment of the invention. Therefore, the phrases "in one embodiment" or "in an embodiment" appearing in various places throughout this specification do not necessarily refer to the same embodiment, but may refer to the same embodiment.

[0047] Furthermore, as those skilled in the art will understand from this disclosure, specific features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. Moreover, as those skilled in the art will understand, although some embodiments described herein include certain features but not others contained in other embodiments, combinations of features from different embodiments are intended to be within the scope of the invention and form different embodiments. For example, in the appended claims, any of the described embodiments can be used in any combination.

[0048] In a first embodiment, the present invention relates to a polyurea copolymer obtained by the following reaction:

[0049] a. Isocyanate mixture (A); and

[0050] b. At least one secondary amine of formula (B):

[0051]

[0052] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered sub-hetero-alkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic cycloalkenyl groups, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylenes, 5-30 membered heterocyclic alkylenes, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heterocyclic alkenylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkylene, substituted or unsubstituted C2-C 30 Alkenyl 5-30 membered heterocyclic alkylene, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 aryl and substituted or unsubstituted C2-C 30 Alkenyl 5-30 quinone heteroaryl,

[0053] R b R c R d R e R f and R g Independently selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30 Alkenyl groups, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic alkyl, substituted or unsubstituted 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 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 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0054] R b and R eAnd the carbon atoms they are bonded to, or

[0055] R c and R f And the carbon atoms they are bonded to, or

[0056] R d and R g And the carbon atoms they are bonded to, or

[0057] R c and R d And the carbon atoms they are bonded to, or

[0058] R c and R b And the carbon atoms they are bonded to, or

[0059] R b and R d And the carbon atoms they are bonded to, or

[0060] R f and R e And the carbon atoms they are bonded to, or

[0061] R e and R g And the carbon atoms they are bonded to, or

[0062] R f and R g and the carbon atoms they are bonded to

[0063] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and

[0064] The isocyanate mixture (A) has an average NCO functionality of ≥2.10;

[0065] More preferably, the polyurea copolymer is obtained by the following reaction:

[0066] a. Isocyanate mixture (A); and

[0067] b. At least one secondary amine of formula (B):

[0068]

[0069] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl, substituted or unsubstituted C5-C 30Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 aryl and substituted or unsubstituted C2-C 30 Alkenyl 5-30 quinone heteroaryl,

[0070] R b R c R d R e R f and R g Independently selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30 Alkenyl groups, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic alkyl, substituted or unsubstituted 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0071] R b and R e And the carbon atoms they are bonded to, or

[0072] R c and R f And the carbon atoms they are bonded to, or

[0073] R d and R g And the carbon atoms they are bonded to, or

[0074] R c and R d And the carbon atoms they are bonded to, or

[0075] R c and R b And the carbon atoms they are bonded to, or

[0076] R b and R d And the carbon atoms they are bonded to, or

[0077] R f and R e And the carbon atoms they are bonded to, or

[0078] R e and R g And the carbon atoms they are bonded to, or

[0079] R f and R g and the carbon atoms they are bonded to

[0080] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and

[0081] The isocyanate mixture (A) has an average NCO functionality of ≥2.10;

[0082] Even more preferably, the polyurea copolymer is obtained by the following reaction:

[0083] a. Isocyanate mixture (A); and

[0084] b. At least one secondary amine of formula (B):

[0085]

[0086] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl and substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 Alpha-aryl

[0087] R b R c R d R e R f and R g Independently selected from 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 C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30Cycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 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 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0088] R b and R e And the carbon atoms they are bonded to, or

[0089] R c and R f And the carbon atoms they are bonded to, or

[0090] R d and R g And the carbon atoms they are bonded to, or

[0091] R c and R d And the carbon atoms they are bonded to, or

[0092] R c and R b And the carbon atoms they are bonded to, or

[0093] R b and R d And the carbon atoms they are bonded to, or

[0094] R f and R e And the carbon atoms they are bonded to, or

[0095] R e and R g And the carbon atoms they are bonded to, or

[0096] R f and R g and the carbon atoms they are bonded to

[0097] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and

[0098] The isocyanate mixture (A) has an average NCO functionality of ≥2.10.

[0099] The molar ratio of NCO in the isocyanate mixture (A) to -NH- in the at least one secondary amine (B) is ≥1.0:2.5 to ≤2.5:1.0; and

[0100] The weight-average molecular weight (Mw) of the polyurea copolymer is 3,000-80,000 g / mol, as determined according to DIN 55672, or, in the case of high molecular weight polymer materials that are no longer soluble in standard organic solvents, the molecular weight is determined according to MALDI-TOF mass spectrometry.

[0101] Most preferably, the polyurea copolymer is obtained through the following reaction:

[0102] a. Isocyanate mixture (A); and

[0103] b. At least one secondary amine of formula (B)

[0104]

[0105] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkyl 5-30-membered heteroaryl groups and substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 Alpha-aryl

[0106] R b R c R d R e Rf and R g Independently selected from 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 C5-C 30 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0107] R b and R e And the carbon atoms they are bonded to, or

[0108] R c and R f And the carbon atoms they are bonded to, or

[0109] R d and R g And the carbon atoms they are bonded to, or

[0110] R c and R d And the carbon atoms they are bonded to, or

[0111] R c and R b And the carbon atoms they are bonded to, or

[0112] R b and R d And the carbon atoms they are bonded to, or

[0113] R f and R e And the carbon atoms they are bonded to, or

[0114] R e and R g And the carbon atoms they are bonded to, or

[0115] R f and R g and the carbon atoms they are bonded to

[0116] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and

[0117] The isocyanate mixture (A) has an average NCO functionality of ≥2.10.

[0118] The molar ratio of NCO in the isocyanate mixture (A) to -NH- in the at least one secondary amine (B) is ≥1.0:2.0 to ≤2.0:1.0; and

[0119] The weight-average molecular weight (Mw) of the polyurea copolymer is 5,000-80,000 g / mol, as determined according to DIN 55672, or, in the case of high molecular weight polymer materials that are no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

[0120] Specifically, the polyurea copolymer is obtained through the following reaction:

[0121] a. Isocyanate mixture (A); and

[0122] b. At least one secondary amine of formula (B)

[0123]

[0124] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl and substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 Alpha-aryl

[0125] R b R c R d R e R f and R g Independently selected from 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 C5-C 30 Cycloalkyl and substituted or unsubstituted C6-C 30 Aryl,

[0126] R b and R e And the carbon atoms they are bonded to, or

[0127] R c and R f And the carbon atoms they are bonded to, or

[0128] R d and R g And the carbon atoms they are bonded to, or

[0129] R c and R d And the carbon atoms they are bonded to, or

[0130] R c and R b And the carbon atoms they are bonded to, or

[0131] R b and R d And the carbon atoms they are bonded to, or

[0132] R f and R e And the carbon atoms they are bonded to, or

[0133] R e and R g And the carbon atoms they are bonded to, or

[0134] R f and R g and the carbon atoms they are bonded to

[0135] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and

[0136] The isocyanate mixture (A) has an average NCO functionality of ≥2.10.

[0137] The molar ratio of NCO in the isocyanate mixture (A) to -NH- in the at least one secondary amine (B) is ≥1.0:0.5 to ≤0.5:1.0; and

[0138] The weight-average molecular weight (Mw) of the polyurea copolymer is 5,000-50,000 g / mol, as determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, as determined by MALDI-TOF mass spectrometry.

[0139] For the purposes of this invention, the term "alkylene" encompasses acyclic saturated hydrocarbon residues, which may be acyclic saturated hydrocarbon chains incorporating different structural moieties, such as those at C1-C2. 30 In the case of alkylene groups, they have 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) carbon atoms, or, as in the case of C1-C5 alkylene groups, 1 to 5 (i.e., 1, 2, 3, 4, or 5) carbon atoms. Representative examples of alkylene groups include, but are not limited to, -CH2-CH2-, -CH2-CH(CH3)-, -CH2-CH(CH2CH3)-, -CH2-CH(n-C3H7)-, -CH2-CH(n-C4H9)-, and -CH2-CH(n-C5H7). 11 -CH2-CH(positive-C6H) 13 -CH2-CH(positive-C7H) 15 -CH2-CH(positive-C8H) 17 )-, -CH(CH3)-CH(CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, and -CH2-[C(CH3)2]2-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 -.

[0140] For the purposes of the present invention, the term "heteroalkylene" refers to an alkylene chain as described above in which one or more carbon atoms are replaced by heteroatoms independently selected from oxygen, sulfur and nitrogen (NH). The heteroalkylene may preferably have 1, 2 or 3, particularly preferably 1 heteroatom selected from oxygen, sulfur and nitrogen (NH) as a chain link. The heteroalkylene may preferably be 2 - 30 membered, particularly preferably 2 - 12 membered, very particularly preferably 2 or 6 membered. More preferably, "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 , -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-OCH 2- , -(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- and -(CH2) 30 -O-CH2, -CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH- and -CH2-CH2-NH-CH2-CH2-.

[0141] The term "subchain alkenyl" within the meaning of this invention includes a noncyclic unsaturated hydrocarbon chain having at least one double bond, preferably one, two, or three double bonds, and may be branched or straight-chain and unsubstituted or at least monosubstituted, such as in C2-C 30 In the case of subalkenyl groups, it has 2-30 (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, more preferably C2-C. 20 Sub-alkenyl groups, preferably C2-C 10 Sub-alkenyl groups, particularly C2-C6 sub-alkenyl groups. Representative examples include -CH=CH- and -CH2-CH=CH-.

[0142] The term "hypoheteroalkenyl" refers to a subchain alkenyl chain as described above, wherein one or more carbon atoms are replaced by heteroatoms, each independently selected from oxygen, sulfur, and nitrogen (NH). The hypoheteroalkenyl group preferably has 1, 2, or 3 members, and particularly preferably 1 heteroatom selected from oxygen, sulfur, and nitrogen (NH) as the chain linker. The hypoheteroalkenyl group is preferably 3-30 quintiles, particularly preferably 3-12 quintiles, and very particularly preferably 3 or 6 quintiles. Examples of hypoheteroalkenyl groups are -CH=CH-NH-, -CH=CH-O-, -CH=CH-CH2-O-, and -CH=CH-S-.

[0143] In another preferred embodiment, if one or more substituents represent alkylene, alkenylene, heteroalkylene, and heteroalkylene or contain such groups (the groups are mono- or poly-substituted), then the group is preferably selected from 1, 2, 3, 4, or 5, particularly preferably 1, 2, or 3, independently selected from 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 group (CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 Alkane, -C(=O)-phenyl, -C(=S)-C 1-5 Alkane, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-OC 1-5 Alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 Alkyl group, -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 substituents, wherein the above-mentioned -C 1-5 In each case, the alkyl group is straight-chain or branched, and the aforementioned phenyl group is unsubstituted or substituted with 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, independently selected from F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 Alkyl, -(CH2)-OC 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5 Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5Substituents of 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, the alkylene, alkenylene, heteroalkylene, and heteroalkylene groups are either unsubstituted or substituted with 1, 2, or 3 substituents independently selected from 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 group is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from F, Cl, Br, I, -OH, -SH, -NO2, -CN, -O-CH3, -O-CF3, and -O-C2H5.

[0144] In another preferred embodiment, the term "cycloalkylene" encompasses saturated cyclic hydrocarbon residues. C5-C 30 Representative examples of cycloalkylene groups include, but are not limited to, cyclopentylenes (e.g., cyclopentyl-1,3-ylidene, cyclopentyl-1,2-ylidene), cyclohexylenes (e.g., cyclohexyl-1,4-ylidene, cyclohexyl-1,3-ylidene, and cyclohexyl-1,2-ylidene), cycloheptylenes, and cyclooctylenes (e.g., 1,5-cyclooctylene). The term "cycloalkylene" also encompasses bridging cyclic hydrocarbon groups, such as cyclic hydrocarbon groups having 2-4 rings containing 5-30 carbon atoms, including but not limited to norbornylenes (e.g., 1,4-norbornylene and 2,5-norbornylene) and adamantylenes (e.g., 1,5-adamantylene and 2,6-adamantylene).

[0145] In another preferred embodiment, for the purposes of this application, the term "heterocyclic alkyl" refers to a cyclic or polycyclic saturated divalent group having 5-30 ring members, wherein a carbon atom is replaced by 1, 2, or 3 heteroatoms selected from N, O, and S. Further examples of this term include 1,5-dioxaoctyl, 4,8-dioxabicyclo[3.3.0]octyl, etc.

[0146] In another preferred embodiment, the term "cycloene-olefin" encompasses a divalent cycloene ring structure, i.e., a cycloene group as defined herein having two single bonds as connection points to other groups. For example, "cycloene-olefin" includes, but is not limited to, cyclopent-1,2-en-3,5-ene, 3-cyclohexene-1,2-ene, 2,5-cyclohexadiene-1,4-ene, cyclohexene-1,2-en-3,5-ene, 2,5-cyclohexadiene-1,4-ene, and cycloheptene-1,2-en-3,5-ene.

[0147] In another preferred embodiment, for the purposes of this application, the term "heterocyclic alkenyl" refers to a cyclic or polycyclic non-aromatic unsaturated divalent group having 5-30 carbon atoms, wherein the carbon atoms are replaced by 1, 2 or 3 heteroatoms selected from N, O and S and have 1, 2 or 3 double bonds.

[0148] In another preferred embodiment, if one or more substituents represent mono- or poly-substituted cycloalkylene, cycloalkylene, heteroalkylene, and heteroalkylene groups, then the group is preferably selected from 1, 2, 3, 4, or 5, particularly preferably from 1, 2, or 3 groups independently selected from 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 group (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)-OC 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 substituents, wherein the above-mentioned -C 1-5 In each case, the alkyl group is straight-chain or branched, and the aforementioned phenyl groups are unsubstituted or substituted, having 1, 2, 3, 4, or 5, preferably having 1, 2, 3, or 4 groups independently selected from F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5 Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5Substituents of 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. The most preferred alkylene, alkenylene, heteroalkylene, and heteroalkylene groups are either unsubstituted or substituted with 1, 2, or 3 substituents independently selected from 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 group is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from F, Cl, Br, I, -SH, -NO2, -CN, -O-CH3, -O-CF3, and -O-C2H5.

[0149] In another preferred embodiment, the term "arylene" refers to a closed aromatic divalent ring or ring system, such as phenylene, naphthylene, biphenylene, fluorene, and indene.

[0150] In another preferred embodiment, the term "heteroaryl" refers to a closed aromatic divalent ring or ring system having at least one heteroatom selected from nitrogen, oxygen, and sulfur. Suitable heteroaryl groups include furanyl, thiopheneyl, pyridinyl, quinolinyl, isoquinolinyl, indoleyl, isoyindoleyl, triazolyl, pyrroleyl, tetrazolyl, imidazolyl, pyrazolyl, and others. azole group, imidazolyl group, benzofuranyl group, benzothiophene group, carbazolyl group, benzo[] Azolyl, pyrimidinyl, benzimidazolyl, quinoxalinyl, benzothiazolyl, naphthinyl, iso- Azolyl, isothiazolyl, purineyl, quinazolinyl, pyrazinyl, 1-pyridyloxy, pyridazinyl, triazinyl, tetrazinyl, etc. Diazole group and thiamethoxamyl group.

[0151] In another preferred embodiment, if one or more substituents represent mono- or poly-substituted arylene and heteroarylene groups, they are preferably 1, 2, 3, or 4, particularly preferably 1, 2, or 3, independently selected from 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 group (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)-OC 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 substituents, wherein the above-mentioned -C 1-5 In each case, the alkyl group is straight-chain or branched, and the aforementioned phenyl group is unsubstituted or is represented by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, independently selected from F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5 Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5 Substituents of 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. The most preferred alkylene, alkenylene, heteroalkylene, and heteroalkylene groups are either unsubstituted or substituted with 1, 2, or 3 substituents independently selected from 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 group is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from F, Cl, Br, I, -SH, -NO2, -CN, -O-CH3, -O-CF3, and -O-C2H5.

[0152] For the purposes of this invention, the term "alkyl" encompasses acyclic saturated hydrocarbon groups, which may be branched or straight-chain and unsubstituted or at least monosubstituted, such as in C1-C2. 30In the case of alkyl groups, they have 1-30 (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) carbon atoms, or, as in the case of C1-C5 alkyl groups, they have 1-5 (i.e., 1, 2, 3, 4, or 5) carbon atoms. If one or more substituents represent alkyl groups or comprise mono- or poly-substituted alkyl groups, they are preferably 1, 2, 3, 4, or 5, particularly preferably 1, 2, or 3, independently selected from F, Cl, Br, I, -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 group (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)-OC 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 substituents, wherein the above C 1-5 In each case, the alkyl group is either straight-chain or branched, and the aforementioned phenyl group is either unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from 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 F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2, and -N(CH3)(C2H5).

[0153] In the preferred embodiment, unsubstituted linear C1-C 30The alkyl group is preferably selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl; more preferably, it is selected from alkyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, and nonadecanyl. The group is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; most preferably from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; particularly preferably from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0154] In the preferred embodiment, unsubstituted branched C1-C 30 The alkyl group is preferably selected from isopropyl, isobutyl, neopentyl, 2-ethylhexyl, 2-propylheptyl, 2-butyloctyl, 2-pentylnonyl, 2-hexyldecyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, and isoeicosyl, more preferably selected from 2-ethylhexyl, 2-propylheptyl, 2-butyloctyl, 2-pentylnonyl, 2-hexyldecyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, isoeicosyl, 2-methyltricaryl, 2-ethyldocoalkyl, 3-ethyldocoalkyl, 3-ethyleicosyl, 4-propyldocoalkyl, propylnonadecyl, 6-butyldodecyl, and 5-ethylundecyl. Polysubstituted alkyl groups should be understood as alkyl groups that are polysubstituted, preferably disubstituted or trisubstituted, at different or the same C atom, for example, in the case of -CF3, trisubstituted at the same C atom, or polysubstituted at different positions, such as in the case of -(CHCl)-(CH2F). Polysubstituted groups can be the same or different substituents. Examples of suitable substituted alkyl groups that may be mentioned are -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.

[0155] In another preferred embodiment, the linear or branched C1-C is replaced 30 Alkyl groups refer to compounds selected from F, Cl, Br, I, -NO2, -CN, -SH, -NH2, and -N(C). 1-5 Alkyl)2, -N(C 1-5 Alkyl)(phenyl), -N(C) 1-5 Alkyl)(CH2-phenyl), -N(C 1-5 Alkyl group (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)-OC 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 C1-C functional groups substituted with alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H 30 Branched or straight-chain saturated hydrocarbon groups of carbon atoms, wherein the above C 1-5 The alkyl group is linear or branched in each case, and the aforementioned phenyl group is preferably unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from 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 F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0156] In another preferred embodiment, substituted, linear, or branched C1-C 30 Alkyl refers to a C1-C alkyl group having a functional group substituted by a functional group selected from the group consisting of: 30Branched or straight-chain saturated hydrocarbon groups of carbon atoms: alkoxy, CN, and SR, preferably selected from 1-methoxymethyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methoxybutyl, 1-methoxypentyl, 1-methoxyhexyl, 1-methoxyheptyl, 1-methoxyoctyl, 1-methoxynonyl, decyl, 1-methoxyundecyl, 1-methoxydodecyl, 1-methoxytridecyl, 1-methoxytetradecyl, 1-methoxypentadecanyl, 1-methoxyhexadecyl, 1-methoxyheptadecyl, 1-methoxyoctadecyl, 1-methoxynonadecanyl, 1-methoxyeicosyl, 1-methoxytetradecyl, 1-methoxytetradecyl, 1-methoxytridecyl, 1-methoxy 2-Methoxypropyl, 2-Methoxybutyl, 2-Methoxypentyl, 2-Methoxyhexyl, 2-Methoxyheptyl, 2-Methoxyoctyl, 2-Methoxynonyl, Decyl, 2-Methoxyundecyl, 2-Methoxydodecyl, 2-Methoxytridecyl, 2-Methoxytetradecyl, 2-Methoxypentadecanyl, 2-Methoxyhexadecyl, 2-Methoxyheptadecyl, 2-Methoxyoctadecyl, 2-Methoxynonadecanyl, 2-Methoxyeicosyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytioecanyl, 2-Methoxytetradecyl, 2-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-acetoxypentadecanyl, 1-acetoxyhexadecyl, 1-acetoxyheptadecyl, 1-acetoxyoctadecyl, 1-acetoxynonadecanyl, 1-acetoxyeicosyl, 1-acetoxytetradecyl, 1-acetoxytidecyl, 1-cyanomethyl, 1-cyanoethyl, 1-cyanopropyl, 1-cyanobutyl, 1-cyanopentyl, 1-cyanohexyl, 1- Cyanoheptyl, 1-Cyanoctyl, 1-Cyanonyl, Decyl, 1-Cyanoundecyl, 1-Cyanododecyl, 1-Cyanotridecyl, 1-Cyanotetradecyl, 1-Cyanopentadecanyl, 1-Cyanohexadecyl, 1-Cyanoheptadecyl, 1-Cyanooctadecyl, 1-Cyanononadecanyl, 1-Cyanoicosyl, 1-Cyanododecyl, 1-Cyanotridecyl, 1-Cyanotetradecyl, 2-Cyanopropyl, 2-Cyanobutyl, 2-Cyanopentyl, 2-Cyanohexyl, 2-Cyanoheptyl, 2-Cyanooctyl, 2-Cyanononyl, Decyl, 2-Cyanoundecyl, 2-Cyanododecyl, 2-Cyanotridecyl, 2-Cyanotetradecyl, 2-Cyanopentadecanyl2-Cyanohexadecanyl, 2-Cyanohepadecanyl, 2-Cyanoctadecyl, 2-Cyanonadecanyl, 2-Cyanoecradecyl, 2-Cyanoecradodecyl, 2-Cyanoecradotane, 2-Cyanoecradotane, 2-Cyanoecradotane, 1-Thioylmethyl, 1-Thioylethyl, 1-Thioylpropyl, 1-Thioylbutyl, 1-Thioylpentyl, 1-Thioylhexyl, 1-Thioylheptyl, 1-Thioyloctyl, 1-Thioylnonyl, decyl, 1-Thioylundecyl, 1-Thioyldodecyl, 1-Thioyltridecyl, 1-Thioyltetradecyl, 1-Thioylpentadecanyl, 1-Thioylhexadecyl, 1-Thioylheptadecyl, 1-Thioyloctadecyl, 1-Thioylnonadecanyl, 1-Thioylecradecyl, 1-Thioyltecradecyl, 1-Thioyldotane, 1-Thioyltetradecyl and 1-Thioyltetradecyl.

[0157] In a preferred embodiment, the term alkenyl refers to an unsubstituted straight-chain C2-C 30 Alkenyl groups, preferably selected from 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-tetraceneenyl, 2-tetraceneenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecanenyl, 2-pentadecanenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecanenyl, 2-nonadecanenyl, 1-eicosenecanenyl, and 2-eicosenecanenyl, 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-tetanelenyl, 2-tetanelenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-eicosenelenyl and 2-eicosenelenyl, 20-eicosenelenyl, 2-docenyl, 6-tridecenyl and 2-tetradecenyl.

[0158] In the preferred embodiment, unsubstituted branched C2-C 30The alkenyl group is selected from isopropenyl, isobutylenyl, neopentenyl, 2-ethylhexenyl, 2-propylheptenyl, 2-butyloctenyl, 2-pentylnonenyl, 2-hexyldecenyl, isohexenyl, isoheptenyl, isooctenyl, isononenyl, isodecanenyl, isodecadecenyl, isodecadecenyl, isohexadecanenyl, 2-methyltetradecenyl, 2-ethyltetradecenyl, 3-ethyltetradecenyl, 3-ethyleicoseneyl, 4-propyltetradecenyl, 4-propylnonadecanenyl, 6-butyldodecenyl, 5-ethylundecenyl, 1,4-hexadienyl, 1 3-Hexadienyl, 2,5-Hexadienyl, 3,5-Hexadienyl, 2,4-Hexadienyl, 1,3,5-Hextrienyl, 1,3,6-Hepttrienyl, 1,4,7-Octatrienyl or 2-methyl-1,3,5-Hextrienyl, 1,3,5,7-Octatrienyl, 1,3,5,8-Nonatetraenyl, 1,4,7,10-Undecanetraenyl, 2-Ethyl-1,3,6,8-Nonatetraenyl, 2-Vinyl-1,3,5,8-Nonatetraenyl, 1,3,5,7,9-Decapentanyl, 1,4,6,8,10-Undecanetraenyl and 1,4,6,9,11-Dodecanetraenyl.

[0159] In a preferred embodiment, the linear or branched C2-C is replaced. 30 Alkenyl groups refer to C2-C atoms that are substituted with functional groups selected from alkoxy, (=O)R, CN, and SR. 30 A branched or straight-chain unsaturated hydrocarbon group of carbon atom; wherein R is hydrogen, substituted or unsubstituted straight-chain or branched C1-C 30 Alkyl, substituted or unsubstituted straight or branched C2-C 30 Alkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Aryl alkyl group.

[0160] In a preferred embodiment, the term alkenyl refers to a C2-C group having a functional group substituted by a functional group selected from alkoxy, C(=O)R, CN, and SR. 30Branched or straight-chain unsaturated hydrocarbon groups of carbon atoms; preferably selected from 1-methoxyvinyl, 2-methoxypropenyl, 4-methoxybutenyl, 3-methoxypentenyl, 5-methoxyhexenyl, 2-methoxyheptenyl, 5-methoxyoctenyl, 3-methoxynonenyl, 6-methoxyundecenyl, 1-methoxydodec-2-enyl, 1-methoxydecadec-5-enyl, 3-methoxytetradec-5-enyl, 3-methoxypentadecadec-12-enyl, 10-methoxyhexadec-15-enyl, 12-methoxyheptadec-16-enyl, 1-methoxyoctadec-3-enyl, 1-methoxynondecadec-2-enyl, 1-methoxyeicosuccica-20-enyl, 1-methoxytetradec-2-enyl 1-Methoxydoc2-4-enyl, 1-Methoxydoc2-22-enyl, 1-Methoxydoc2-23-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-Methoxytetracene-12-enyl, 2-Methoxytetradec-10-enyl, 2-Methoxypentadecan-14-enyl, 2-Methoxyhexadec-1-enyl, 2-Methoxyheptadec-1-enyl, 2-Methoxyoctadec-12-enyl, 2 -Methoxy-19-carbon-10-enyl, 2-methoxy-10-carbon-18-enyl, 2-methoxy-21-carbon-2-enyl, 2-methoxy-32-carbon-3-enyl, 20-methoxy-33-carbon-2-enyl, 21-methoxy-44-carbon-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-acetoxydecadec-12- Alkenyl, 10-acetoxytetradec-2-enyl, 15-acetoxypentadecan-2-enyl, 10-acetoxyhexadec-2-enyl, 11-acetoxyheptadec-1-enyl, 13-acetoxyoctadec-2-enyl, 1-acetoxyneoctadec-14-enyl, 20-acetoxyeicos ...1-Cyanoct-2-enyl, 1-Cyanonon-3-enyl, 11-Cyanoundec-2-enyl, 10-Cyanododec-2-enyl, 10-Cyanotridec-12-enyl, 1-Cyanotetradec-3-enyl, 1-Cyanopentadecande ... 2-C2-20-enyl, 1-Cyano-2-C2-enyl, 2-Cyano-prop-2-enyl, 2-Cyano-but-1-enyl, 2-Cyano-pent-1-enyl, 2-Cyano-hex-3-enyl, 2-Cyano-hept-6-enyl, 2-Cyano-oct-1-enyl, 2-Cyano-non-8-enyl, 2-Cyano-undec-10-enyl, 2-Cyano-dodec-1-enyl, 2-Cyano-tweldedec-12-enyl, 2-Cyano-tetradec-10-enyl, 2-Cyano-pentadedec-3-enyl, 2-Cyano-hexadec-2-enyl, 2-Cyano-heptadec-1 -alkenyl, 2-cyanooctadec-12-alkenyl, 2-cyanononadecan-15-alkenyl, 2-cyanoeicosico-1-alkenyl, 2-cyanotetradec-5-alkenyl, 2-cyanotetradec-20-alkenyl, 2-cyanotetradec-22-alkenyl, 2-cyanotetradec-20-alkenyl, 1-thioylethen-1-alkenyl, 1-thioylpropen-2-alkenyl, 1-thioylbuten-2-alkenyl, 1-thioylpenten-4-alkenyl, 1-thioylhexen-2-alkenyl, 1-thioylhepten-5-alkenyl, 1-thioylocten-3-alkenyl, 1-thioylnonen-5-alkenyl, 1 -Thioyl undec-10-enyl, 1-thioyl dodec-11-enyl, 1-thioyl tridec-2-enyl, 1-thioyl tetradec-4-enyl, 1-thioyl pentadec-5-enyl, 1-thioyl hexadec-3-enyl, 1-thioyl heptadecan-2-enyl, 1-thioyl octadec-3-enyl, 1-thioyl nonadecan-15-enyl, 1-thioyl eicosatecan-18-enyl, 1-thioyl tiicosatecan-20-enyl, 1-thioyl tiicosatecan-21-enyl, 1-thioyl tiicosatecan-20-enyl, and 1-thioyl tiicosatecan-22-enyl.

[0161] In a preferred embodiment, the term "heteroalkyl" refers to an alkyl group in which one or more carbon atoms are replaced by heteroatoms independently selected from oxygen, sulfur, and nitrogen (NH) in each case. The heteroalkyl group preferably comprises one, two, or three heteroatoms independently selected from oxygen, sulfur, and nitrogen (NH) as chain links. The heteroalkyl group is preferably 2-12 quinary, and particularly preferably 2-6 quinary.

[0162] In a preferred embodiment, the term "heteroalkenyl" refers to an alkenyl group in which one or more carbon atoms are replaced by heteroatoms independently selected from oxygen, sulfur, and nitrogen (NH) in each case. The heteroalkenyl group preferably comprises one, two, or three heteroatoms independently selected from oxygen, sulfur, and nitrogen (NH) as chain links. The heteroalkenyl group is preferably 3-12 quinary, and particularly preferably 3-6 quinary.

[0163] In a preferred embodiment, the term "cycloalkyl" refers to a monocyclic or bicyclic saturated alicyclic group having 5-30 carbon atoms. Unsubstituted or branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclic [2.2.1]heptyl, and bicyclic [3.1.1]heptyl.

[0164] In another preferred embodiment, C5-C 30 Monocyclic and bicyclic cycloalkyl groups 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. Branching C3-C 10 Representative examples of monocyclic and bicyclic cycloalkyl groups include, but are not limited to, methylcyclohexyl and dimethylcyclohexyl.

[0165] In a preferred embodiment, the term "cycloalkenyl" refers to a monocyclic or bicyclic unsaturated alicyclic group having 5-30 carbon atoms, comprising one or more double bonds. (C5-C) 30 Representative examples of cycloalkenyl groups include, but are not limited to, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, or cyclodecenyl. These groups may be branched with one or more of the same or different alkyl groups, preferably methyl, ethyl, n-propyl, or isopropyl. Branching C5-C 30 Representative examples of monocyclic and bicyclic cycloalkenyl groups include, but are not limited to, methylcyclohexenyl and dimethylcyclohexenyl.

[0166] In a preferred embodiment, the term "heterocyclic alkyl" refers to a non-aromatic monocyclic or polycyclic ring comprising 5-30 ring members, wherein at least one carbon atom that is a ring member is replaced by at least one heteroatom selected from O, S, and N. Examples of heterocyclic alkyl groups include aziridinyl, pyrrolyl, pyrrolidine, piperidinyl, piperidinyl, piperazinyl, piperazinyl, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl, and pyranyl.

[0167] In a preferred embodiment, the term "heterocyclic alkenyl" refers to a non-aromatic unsaturated monocyclic or polycyclic ring comprising 5-30 ring members, wherein at least one carbon atom serving as a ring member is replaced by at least one heteroatom selected from O, S, and N and has at least one double bond. Examples include, but are not limited to, (2,3)-dihydrofuranyl, (2,3)-dihydrothiophenyl, (2,3)-dihydropyrroleyl, (2,5)-dihydropyrroleyl, (2,5)-dihydropyrroleyl, and (2,3)-dihydroisocyanuryl. Azoxyl, (1,4)-dihydropyridin-1-yl, dihydropyranyl, 2,3-dihydropyrazole-1-yl, 2,3-dihydropyrazole-2-yl, 2,3-dihydropyrazole-3-yl, 2,3-dihydropyrazole-4-yl, 2,3-dihydropyrazole-5-yl, 3,4-dihydropyrazole-1-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-4-yl, 3,4-dihydropyrazole-5-yl, 4,5-dihydropyrazole-1-yl, 4,5-dihydropyrazole-3-yl, 4,5-dihydropyrazole-4-yl, 4,5-dihydropyrazole-5-yl, 2,3-dihydropyrazole-1-yl, 4,5-dihydropyrazole-3-yl, 4,5-dihydropyrazole-4-yl, 4,5-dihydropyrazole-5-yl, 2,3-dihydropyrazole-1-yl, 3,4 ...1-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-4-yl, 3,4-dihydropyrazole-5-yl, 3,4-dihydropyrazole-1-yl, 3,4-dihydropyrazole-1-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-4-yl, 3,4-dihydropyrazole-5-yl, 3,4 2-Azazole, 2,3-dihydro Azol-3-yl, 2,3-dihydro Azol-4-yl, 2,3-dihydro Azol-5-yl, 3,4-dihydro 2-Azazole, 3,4-dihydro Azol-3-yl, 3,4-dihydro Azol-4-yl, 4,5-dihydropyrazole-2-yl, 4,5-dihydropyrazole-3-yl, 4,5-dihydropyrazole-4-yl, 4,5-dihydropyrazole-5-yl, 2,5-dihydrothiopheneyl and (1,2,3,4)-tetrahydropyridine-1-yl.

[0168] In another preferred embodiment, if one or more substituents represent mono- or poly-substituted heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, and heterocycloalkenyl groups, then the group is preferably selected from 1, 2, 3, 4, or 5, and particularly preferably from 1, 2, or 3 groups independently selected from F, Cl, Br, I, -CN, -NO2, -OH, -SH, -NH2, oxo (=O), thio (=S), -C (=O)-OH, C 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkyne group, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -(CH2)-OC 1-5 Alkyl, -SC 1-5 Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5Alkyl, -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)-OC 1-5 Alkyl, -C(=O)-H, -C(=O)-C 1-5 Alkyl, -CH2-OC(=O)-phenyl, -OC(=O)-phenyl, -NH-S(=O)2-C 1-5 Alkyl group, -NH-C(=O)-C 1-5 Alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 Alkyl, -C(=O)-N(C) 1-5 Substitution of alkyl groups, pyrazolyl, phenyl, furanyl, thiadiazolyl, thiophene, and benzyl groups, wherein the above C 1-5 In each case, the alkyl group is either straight-chain or branched, and the cyclic substituents, or the cyclic groups themselves, are either unsubstituted or substituted by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, independently selected from F, Cl, Br, I, -CN, -CF3, -OH, -NH2, -O-CF3, -SH, -OC. 1-5 Alkyl, -O-phenyl, -O-CH2-phenyl, -(CH2)-OC 1-5 Alkyl, -SC 1-5 Alkyl, -S-phenyl, -S-CH2-phenyl, -C 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkyne group, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -C(=O)-OC 1-5 Alkyl groups and -C(=O)-CF3 substituents are used for substitution.

[0169] In a preferred embodiment, the term "aryl" refers to an aromatic compound that may have more than one aromatic ring. Substituted and unsubstituted C6-C 30 Representative examples of aryl groups include phenyl, naphthyl, anthracene, tetraphenyl, naphthylphenyl, and phenanthrene.

[0170] In a preferred embodiment, the term "heteroaryl" refers to a monocyclic or polycyclic aromatic hydrocarbon group, preferably a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon group, preferably having 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, and very particularly preferably having 5 or 6 ring members, wherein one or more carbon atoms as ring members are replaced by heteroatoms each independently selected from oxygen, sulfur, and nitrogen (NH). The heteroaryl group may preferably contain 1, 2, 3, 4, or 5, particularly preferably 1, 2, or 3 heteroatoms independently selected from oxygen, sulfur, and nitrogen (NH) as ring members. The heteroaryl group is unsubstituted, monosubstituted, or polysubstituted in the same or different ways. Suitable examples of heteroaryl groups that may be mentioned include thienyl, furanyl, pyrroleyl, pyrazolyl, pyrazinyl, pyranyl, triazolyl, pyridyl, imidazolyl, indoleyl, isoyindoleyl, benzo[b]furanyl, benzo[b]thienyl, benzo[d]thiazolyl, benzodiazolyl, benzotriazolyl, and benzo[b]furanyl. azole group, benzo[a] azole group, thiazolyl group, thiadiazole group, azole group, diazole group, iso Azolyl, pyridinyl, pyrimidinyl, indazole, quinoxalinyl, quinazolinyl, quinolinyl, naphridinyl, and isoquinolinyl.

[0171] For the purposes of this invention, aryl or heteroaryl groups can be fused with monocyclic or bicyclic systems. Examples of aryl groups that can be mentioned for fusion with monocyclic or bicyclic systems include (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, (2,3)-dihydro-1H-isoindolyl, (1,2,3,4)-tetrahydronaphthyl, and (2,3)-dihydrobenzo[1.4]di Alkenyl, benzo[1.3]dioxolane, and (3,4)-dihydro-2H-benzo[1.4] Azine group.

[0172] In another preferred embodiment, "aralkyl" refers to an aromatic ring attached to an alkyl chain. Representative examples of aralkyl groups 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.

[0173] In another preferred embodiment, if one or more substituents represent aryl, heteroaryl, or aralkyl groups, or contain mono- or poly-substituted aryl or heteroaryl groups, they may preferably be 1, 2, 3, 4, or 5, and particularly preferably 1, 2, or 3, independently selected from F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5 Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 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)-OC 1-5 Alkyl, -C(=O)-H, -C(=O)-C 1-5 Alkyl, -CH2-OC(=O)-phenyl, -OC(=O)-phenyl, -NH-S(=O)2-C 1-5 Alkyl group, -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, furanyl, thiazolyl, thiadiazolyl, thiophene, benzyl and phenethyl substituents, wherein the above C 1-5 In each case, the alkyl group is either straight-chain or branched, and the cyclic substituents or the cyclic groups of these substituents are either unsubstituted or replaced by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, independently selected from F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 Alkyl, -C 2-5 alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5Substituents of 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, the substituents are independently selected from F, Cl, Br, I, -CN, -NO2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, neopentyl, vinyl, allyl, ethynyl, propynyl, -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, in each case. -O-C3H7, -OC(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-OC(=O)-phenyl, -NH-S(=O)2-CH3, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-OC(CH3)3, -C(=O)-H, -C(=O)-CH3, -C(=O) -C2H5, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -OC(=O)-phenyl, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, phenyl, furanyl, thiadiazolyl, thiophene, and benzyl, wherein in each case, the cyclic substituent or the cyclic group itself of these substituents is unsubstituted or is replaced by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, independently selected from 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 Substituents of vinyl, allyl, ethynyl, propynyl, -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, -OC(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, and -S-CH2F.

[0174] In another preferred embodiment, the substituted aryl group may be selected from 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-methylsulfinylphenyl, 3-methylsulfinylphenyl, 4-methylsulfinylphenyl, 2-methoxy Phenyl, 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-Acetaminophenyl, 3-Acetaminophenyl, 4-Acetaminophenyl, 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-Carboxymethyl ester phenyl, 3-Carboxymethyl ester phenyl, 4-Carboxymethyl ester phenyl, 2-Carboxyethyl ester phenyl, 3-Carboxyethyl ester phenyl, 4-Carboxyethyl ester phenyl, 2-Carboxyter-butyl ester phenyl, 3-Carboxyter-butyl ester phenyl, 4-Carboxyter-butyl ester phenyl, 2-Methylmercaptophenyl, 3-Methylmercaptophenyl, 4-Methylmercaptophenyl, 2-Ethylmercaptophenyl, 3-Ethylmercaptophenyl, 4-Ethylmercaptophenyl, 2-Biphenyl, 3-Biphenyl, 4-Biphenyl2-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-chloro Phenyl, 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-trifluoromethylphenyl5-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.

[0175] In another preferred embodiment, the substituted heteroaryl group may be selected from 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-Methylthiazole-2-yl, 5-Methylthiazole-2-yl, 4-Trifluoromethylthiazole-2-yl, 5-Trifluoromethylthiazole-2-yl, 4-Chlorothiazole-2-yl, 5-Chlorothiazole-2-yl, 4-Bromothiazole-2-yl, 5-Bromothiazole-2-yl, 4-Fluorothiazole-2-yl, 5-Fluorothiazole-2-yl, 4-Cyanothiazole-2-yl, 5-Cyanothiazole-2-yl, 4-Methoxythiazole-2-yl, 5-Methoxythiazole-2-yl, 4-Methyl 2-Azolium-5-methyl 2-Azazole, 4-trifluoromethyl 2-Azazole, 5-trifluoromethyl 2-Azolium, 4-chloro 2-Azolium, 5-chloro Azol-2-yl, 4-bromo Azol-2-yl, 5-bromo 2-Azazole, 4-Fluoride 2-Azolium-5-fluoro 2-Azol-4-cyano 2-Azolium, 5-Cyano 2-Azolium, 4-methoxy 2-Azolium, 5-methoxy 2-Azolium-2-yl, 2-methyl-(1,2,4)-thiadiazole-5-yl, 2-trifluoromethyl-(1,2,4)-thiadiazole-5-yl, 2-chloro-(1,2,4)-thiadiazole-5-yl, 2-fluoro-(1,2,4)-thiadiazole-5-yl, 2-methoxy-(1,2,4)-thiadiazole-5-yl, 2-cyano-(1,2,4)-thiadiazole-5-yl, 2-methyl-(1,2,4)- Diazol-5-yl, 2-trifluoromethyl-(1,2,4)- Diazol-5-yl, 2-chloro-(1,2,4)- Diazol-5-yl, 2-fluoro-(1,2,4)- Diazol-5-yl, 2-methoxy-(1,2,4)- Diazol-5-yl and 2-cyano-(1,2,4)- Diazol-5-yl.

[0176] In another preferred embodiment, the average NCO functionality of the isocyanate mixture (A) is ≥2.10 to ≤6.0; more preferably, the average NCO functionality of the isocyanate mixture (A) is ≥2.10 to ≤5.0; even more preferably, the average NCO functionality of the isocyanate mixture (A) is ≥2.10 to ≤4.5; most preferably, the average NCO functionality of the isocyanate mixture (A) is ≥2.10 to ≤4.0; particularly, the average NCO functionality of the isocyanate mixture (A) is ≥2.10 to ≤3.0.

[0177] In another preferred embodiment, R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene and substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 Aromatic; more preferably, R a Selected from substituted or unsubstituted linear or branched C1-C 20Alkylene, substituted or unsubstituted C5-C 20 Cycloalkylene, substituted or unsubstituted C1-C 20 Alkylene C5-C 20 Cycloalkylene and substituted or unsubstituted C6-C 20 Alpha-aryl C1-C 20 Alkylene C6-C 20 Alpha-aryl; or even more preferably, R a Selected from substituted or unsubstituted linear or branched C1-C 10 Alkylene, substituted or unsubstituted C5-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Alkylene C5-C 10 Cycloalkylene and substituted or unsubstituted C6-C 10 Alpha-aryl C1-C 10 Alkylene C6-C 10 Aromatic; most preferably, R a Selected from substituted or unsubstituted linear or branched C1-C 10 Alkylene, substituted or unsubstituted C5-C8 cycloalkylene, substituted or unsubstituted C1-C8 alkylene, and substituted or unsubstituted C6-C8 arylene; particularly, R a Selected from substituted or unsubstituted linear or branched C1-C 10 Alkylene, substituted or unsubstituted C5-C7 cycloalkylene, substituted or unsubstituted C1-C8 alkylene, C5-C7 cycloalkylene, and substituted or unsubstituted C6-C7 arylene, C1-C8 alkylene, and C6-C7 arylene.

[0178] In another preferred embodiment, R b R c R d R e R f and R g Independently selected from straight-chain or branched substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C5-C groups. 30 cycloalkyl, substituted or unsubstituted C6-C 30 Aryl and substituted or unsubstituted 5-30 membered heteroaryl groups,

[0179] R b and R e And the carbon atoms they are bonded to, or

[0180] R c and R f And the carbon atoms they are bonded to, or

[0181] Rd and R g And the carbon atoms they are bonded to, or

[0182] R c and R d And the carbon atoms they are bonded to, or

[0183] R c and R b And the carbon atoms they are bonded to, or

[0184] R b and R d And the carbon atoms they are bonded to, or

[0185] R f and R e And the carbon atoms they are bonded to, or

[0186] R e and R g And the carbon atoms they are bonded to, or

[0187] R f and R g and the carbon atoms they are bonded to

[0188] Together they form saturated or unsaturated unsubstituted or substituted 5-30 member carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members;

[0189] More preferably, R b R c R d R e R f and R g Independently selected from linear or branched substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C5-C 20 cycloalkyl, substituted or unsubstituted C6-C 20 Aryl and substituted or unsubstituted 5-20 membered heteroaryl groups,

[0190] R b and R e And the carbon atoms they are bonded to, or

[0191] R c and R f And the carbon atoms they are bonded to, or

[0192] R d and R g And the carbon atoms they are bonded to, or

[0193] R cand R d And the carbon atoms they are bonded to, or

[0194] R c and R b And the carbon atoms they are bonded to, or

[0195] R b and R d And the carbon atoms they are bonded to, or

[0196] R f and R e And the carbon atoms they are bonded to, or

[0197] R e and R g And the carbon atoms they are bonded to, or

[0198] R f and R g and the carbon atoms they are bonded to

[0199] Together they form saturated or unsaturated unsubstituted or substituted 5-20 member carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members;

[0200] Even more preferably, R b R c R d R e R f and R g Independently selected from linear or branched substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C5-C 10 cycloalkyl, substituted or unsubstituted C6-C 10 Aryl and substituted or unsubstituted 5-10 membered heteroaryl groups,

[0201] R b and R e And the carbon atoms they are bonded to, or

[0202] R c and R f And the carbon atoms they are bonded to, or

[0203] R d and R g And the carbon atoms they are bonded to, or

[0204] R c and R d And the carbon atoms they are bonded to, or

[0205] R c and Rb And the carbon atoms they are bonded to, or

[0206] R b and R d And the carbon atoms they are bonded to, or

[0207] R f and R e And the carbon atoms they are bonded to, or

[0208] R e and R g And the carbon atoms they are bonded to, or

[0209] R f and R g Together with the carbon atoms they bond to, they form saturated or unsaturated unsubstituted or substituted 5-10 membered carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members.

[0210] Most preferably, R b R c R d R e R f and R g Independently selected from linear or branched substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C5-C7 cycloalkyl groups, substituted or unsubstituted C6-C7 aryl groups, and substituted or unsubstituted 5-7 heteroaryl groups.

[0211] R b and R e And the carbon atoms they are bonded to, or

[0212] R c and R f And the carbon atoms they are bonded to, or

[0213] R d and R g And the carbon atoms they are bonded to, or

[0214] R c and R d And the carbon atoms they are bonded to, or

[0215] R c and R b And the carbon atoms they are bonded to, or

[0216] R b and R d And the carbon atoms they are bonded to, or

[0217] R fand R e And the carbon atoms they are bonded to, or

[0218] R e and R g And the carbon atoms they are bonded to, or

[0219] R f and R g and the carbon atoms they are bonded to

[0220] Together they form saturated or unsaturated unsubstituted or substituted 5-10 membered carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members;

[0221] In particular, R b R c R d R e R f and R g Independently selected from linear or branched substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C5-C7 cycloalkyl groups, substituted or unsubstituted C6-C7 aryl groups, and substituted or unsubstituted 5-7 heteroaryl groups.

[0222] R b and R e And the carbon atoms they are bonded to, or

[0223] R c and R f And the carbon atoms they are bonded to, or

[0224] R d and R g And the carbon atoms they are bonded to, or

[0225] R c and R d And the carbon atoms they are bonded to, or

[0226] R c and R b And the carbon atoms they are bonded to, or

[0227] R b and R d And the carbon atoms they are bonded to, or

[0228] R f and R e And the carbon atoms they are bonded to, or

[0229] R e and R g And the carbon atoms they are bonded to, or

[0230] R f and R g and the carbon atoms they are bonded to

[0231] Together they form saturated or unsaturated unsubstituted or substituted 5-10 member carbon rings, which contain 0, 1 or 2 heteroatoms selected from O or N as ring members.

[0232] In another implementation, R b R c R d R e R f and R g Independently selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C5-C 30 Cycloalkyl and substituted or unsubstituted C6-C 30 Aryl;

[0233] R b and R e And the carbon atoms they are bonded to, or

[0234] R c and R d And the carbon atoms they are bonded to, or

[0235] R f and R e and the carbon atoms they are bonded to

[0236] Together they form saturated, unsaturated or aromatic, unsubstituted or substituted 5-30 member carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members.

[0237] In another preferred embodiment, R a Selected from substituted or unsubstituted linear or branched C1-C 10 Alkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl, substituted or unsubstituted C5-C 10 Cycloalkylene, substituted or unsubstituted C5-C8 cycloalkylene, substituted or unsubstituted C6-C 10 aryl, substituted or unsubstituted C1-C 10 Alkylene C5-C8 cycloalkylene, substituted or unsubstituted C1-C 10 Alkylene 5-10-membered heterocyclic alkylene, substituted or unsubstituted C1-C 10 Alkylene C6-C 10 Aspartic, C5-C 10 Cycloalkylene and substituted or unsubstituted C2-C10 Sub-alkenyl 5-10-membered sub-heterocyclic alkyl groups.

[0238] In another preferred embodiment, the secondary amine of formula (B) is selected from N1,N3-diisopropyl-4-methylcyclohexane-1,3-diamine, 4-methyl-N1,N3-di-sec-butylcyclohexane-1,3-diamine, 2-methyl-N1,N3-di-sec-butylcyclohexane-1,3-diamine, N1,N3-dibenzyl-2-methylcyclohexane-1,3-diamine, N1,N3-dibenzyl-4-methylcyclohexane-1,3-diamine, N1,N3-bis(2-ethylhexyl)-4-methylcyclohexane-1,3-diamine, N-isopropyl-3-[(isopropylamino)methyl]-3,5,5-trimethylcyclohexylamine, N-sec-butyl-4-[[4-(sec-butylamino)methyl]-3,5,5-trimethylcyclohexylamine, and N-sec-butyl-4-[[4-(sec-butylamino)methyl]-3,5,5-trimethylcyclohexylamine. [Phenyl]methyl]aniline, N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)hexane-1,6-diamine, N,N'-diethyl-2-butene-1,4-diamine, N,N'-diisopropyl-1,3-propanediamine, N,N'-diisopropylethylenediamine, N,N'-dimethyl-1,3-propanediamine, 1,4,8,11-tetraazacyclotetradecane-5,7-dione, 1,4-diazacycloheptane, 1,2-dimethylethylenediamine, 1,2-diisopropylethylenediamine, N-(pyrrolidine-2-ylmethyl)cyclohexylamine, N-(pyrrolidine-2-ylmethyl)cycloheptylamine, and 2-methyl-N-(pyrrolidine-2-ylmethyl)prop-2-amine.

[0239] In another preferred embodiment, the secondary amine of formula (B) includes a primary amine.

[0240] In another preferred embodiment, the primary amine is present in the secondary amine of formula (B) in an amount of 0-10% by weight based on the total weight of the secondary amine of formula (B); more preferably, the primary amine is present in the secondary amine of formula (B) in an amount of 0-8% by weight based on the total weight of the secondary amine of formula (B); even more preferably, the primary amine is present in the secondary amine of formula (B) in an amount of 0.5-5% by weight based on the total weight of the secondary amine of formula (B); most preferably, the primary amine is present in the secondary amine of formula (B) in an amount of 1-4% by weight based on the total weight of the secondary amine of formula (B); particularly, the primary amine is present in the secondary amine of formula (B) in an amount of 1-3% by weight based on the total weight of the secondary amine of formula (B).

[0241] In another preferred embodiment, the isocyanate mixture (A) comprises at least one isocyanate with an NCO functionality ≥ 3.0.

[0242] In another preferred embodiment, the at least one isocyanate with an NCO functionality ≥ 3.0 is selected from triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-triisocyanate, L-lysine ethyl triisocyanate, 1,6,11-triisocyanate undecane, 2,2-bis[[4-(isocyanate-methyl)phenyl]methyl]butyl-n-[[4-(isocyanate-methyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)tris(hexamethylene) Isocyanates, 1,3,5-triisocyanate-based benzene, tris(isocyanate-based hexyl) biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyltri(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-based dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and triisocyanates in polymeric form.

[0243] The term "polymeric" refers to the polymerization grade of aliphatic and / or aromatic polyisocyanates, which independently contain different oligomers and homologues.

[0244] In another preferred embodiment, the diisocyanate is polymerized in the form of methylene diphenyl diisocyanate.

[0245] In another preferred embodiment, the polymeric forms of diisocyanate and triisocyanate include polymeric methylene diphenyl diisocyanate and toluene diisocyanate.

[0246] In another preferred embodiment, the polymerized methylene diphenyl diisocyanate comprises oligomers and methylene diphenyl diisocyanate isomers. Thus, the polymerized methylene diphenyl diisocyanate may comprise a single methylene diphenyl diisocyanate isomer or a mixture of isomers of two or three methylene diphenyl diisocyanate isomers, with the balance being oligomers. The polymerized methylene diphenyl diisocyanate tends to have an isocyanate functionality of ≥2.10, preferably ≥3.0. In these products, the isomer ratio and the amount of oligomers can vary over a wide range. For example, the polymerized methylene diphenyl diisocyanate typically comprises about 30-80% by weight of a methylene diphenyl diisocyanate isomer, with the balance being said oligomers. The methylene diphenyl diisocyanate isomers are typically a mixture of 4,4'-methylene diphenyl diisocyanate, 2,4'-methylene diphenyl diisocyanate, and very low levels of 2,2'-methylene diphenyl diisocyanate.

[0247] In another preferred embodiment, the isocyanate mixture (A) comprises at least one isocyanate with an NCO functionality of 2.0.

[0248] In another preferred embodiment, the at least one isocyanate with an NCO functionality of 2.0 is selected from isophorone diisocyanate, propylene-1,2-diisocyanate, propylene-1,3-diisocyanate, butylene-1,2-diisocyanate, butylene-1,3-diisocyanate, hexamethylene-1,6-diisocyanate, 2-methylpentamethylene-1,5-diisocyanate, 2-ethylbutylene-1,4-diisocyanate, 1,5-pentamethylene diisocyanate, methyl-2,6-diisocyanate hexanoate, octamethylene-1,8-diisocyanate, 2,4,4-trimethylhexamethylene-1,6-diisocyanate, nonamethylene diisocyanate, 2,2,4-trimethylhexamethylene-1,6- Diisocyanate, decamethyl-1,10-diisocyanate, 2,11-diisocyanate-dodecane, metaphenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, methylpropylphenyl diisocyanate, methylethylphenyl diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, methylene bis(4-phenylisocyanate), ethylene bis(4-phenylisocyanate), isopropylene bis(4-phenylisocyanate) Butylenebis(4-phenylisocyanate), 2,2'-oxydiphenyl diisocyanate, 3,3'-oxydiphenyl diisocyanate, 4,4'-oxydiphenyl diisocyanate, 2,2'-ketodiphenyl diisocyanate, 3,3'-ketodiphenyl diisocyanate, 4,4'-ketodiphenyl diisocyanate, 2,2'-mercaptodiphenyl diisocyanate, 3,3'-mercaptodiphenyl diisocyanate, 4,4'-thiodiphenyl diisocyanate, 2,2'-diphenyl sulfone diisocyanate, 3,3'-diphenyl sulfone diisocyanate, 4,4'-diphenyl sulfone diisocyanate, 2,2-methylenebis(cyclohexyl isocyanate), 3,3'-methylenebis(cyclohexyl isocyanate), 4,4'-methylenebis(cyclohexyl isocyanate) Bis(cyclohexyl isocyanate), 4,4'-ethylidene bis(cyclohexyl isocyanate), 4,4'-propylidene bis-(cyclohexyl isocyanate), bis(p-isocyanate-cyclohexyl) sulfone, bis(p-isocyanate-cyclohexyl) ether, bis(p-isocyanate-cyclohexyl) diethylsilane, bis(p-isocyanate-cyclohexyl) diphenylsilane, bis(p-isocyanate-cyclohexyl) ethylphosphine oxide, bis(p-isocyanate-cyclohexyl) phenylphosphine oxide, bis(p-isocyanate-cyclohexyl) N-phenylamine, bis(p-isocyanate-cyclohexyl) N-methylamine, 3,3'-dimethyl-4,4'-diisocyanate-biphenyl, 3,3'-dimethoxy-biphenyl diisocyanate, 2,4-Bis(β-isocyanate-tert-butyl)toluene, bis(p-β-isocyanate-tert-butyl-phenyl) ether, p-bis(2-methyl-4-isocyanate-phenyl)benzene, 3,3-diisocyanate-based aragonane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-based propoxy)ethane, 2,2-dimethylpropylene diisocyanate, 3-methoxyhexamethylene-1,6-diisocyanate, 2,5-dimethylheptamethylene diisocyanate, 5-methylnonamethylene-1,9-diisocyanate, 1,4-diisocyanate-based cyclohexane, 1,2-diisocyanate-based octadecane, 2,5-di- Isocyanate-1,3,4-oxadiazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, and OCN(CH2)3N(CH3)(CH2)3NCO; more preferably, the at least one isocyanate with an NCO functionality of 2.0 is selected from isophorone diisocyanate, propylene-1,3-diisocyanate, hexamethylene-1,6-diisocyanate, 2-methylpentamethylene-1,5-diisocyanate, 2-ethylbutylene-1,4-diisocyanate, 1,5-pentamethylene diisocyanate, methyl-2,6-diisocyanate hexanoate, octamethylene-1,8-diisocyanate, 2,4,4-trimethylhexamethylene-1,6-diisocyanate. Isocyanates, phenylene diisocyanates, p-phenylene diisocyanates, toluene-2,4-diisocyanates, toluene-2,6-diisocyanates, xylene-2,4-diisocyanates, xylene-2,6-diisocyanates, 2,2'-biphenylene diisocyanates, 3,3'-biphenylene diisocyanates, 4,4'-biphenylene diisocyanates, methylene bis(4-phenylisocyanate), 2,2'-diphenyl sulfone diisocyanate, 3,3'-diphenyl sulfone diisocyanate, 4,4'-diphenyl sulfone diisocyanate, 2,2'-methylene bis(cyclohexyl isocyanate), 3,3'-methylene bis(cyclohexyl isocyanate), 4,4'-methylene bis(cyclohexyl isocyanate) ), 4,4'-ethylidene bis(cyclohexyl isocyanate), 4,4'-propylidene bis-(cyclohexyl isocyanate), bis(p-isocyanate-cyclohexyl) sulfide, bis(p-isocyanate-cyclohexyl) sulfone, bis(p-isocyanate-cyclohexyl) ether, bis(p-isocyanate-cyclohexyl) diethylsilane, bis(p-isocyanate-cyclohexyl) diphenylsilane, bis(p-isocyanate-cyclohexyl) ethylphosphine oxide, bis(p-isocyanate-cyclohexyl) phenylphosphine oxide, bis(p-isocyanate-cyclohexyl) N-phenylamine, bis(p-isocyanate-cyclohexyl) N-methylamine, 3,3'-dimethyl-4,4'-diisocyanate-biphenyl, 3,3'-dimethoxy-biphenyl diisocyanate, 2,4-Bis(β-isocyanate-tert-butyl)toluene, bis(p-β-isocyanate-tert-butyl-phenyl) ether, p-bis(2-methyl-4-isocyanate-phenyl)benzene, 3,3-diisocyanate-based adamantane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-based propoxy)ethane, 2,2-dimethylpropylene diisocyanate, 3-methoxyhexamethylene-1,6-diisocyanate, 2,5-dimethylheptamethylene diisocyanate, 5-methylnonamethylene-1,9-diisocyanate, 1,4-diisocyanate-based cyclohexane, 1,2-diisocyanate-based octadecane, 2,5-diisocyanate-based 1,3,4 -oxadiazole, OCN(CH2)3O(CH2)2O(CH2)3NCO and OCN(CH2)3N(CH3)(CH2)3NCO; even more preferably, the at least one isocyanate with a functionality of 2.0 NCO is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 2-methylpentamethylene-1,5-diisocyanate, 2-ethylbutylene-1,4-diisocyanate, 1,5-pentamethylene diisocyanate, methyl-2,6-diisocyanate hexanoate, octamethylene-1,8-diisocyanate, 2,4,4-trimethylhexamethylene-1,6-diisocyanate, metaphenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate. Cyanide esters, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, methylene bis(4-phenylisocyanate), 2,2'-diphenyl sulfone diisocyanate, 3,3'-diphenyl sulfone diisocyanate, 4,4'-diphenyl sulfone diisocyanate, 2,2'-methylene bis(cyclohexyl isocyanate), 3,3'-methylene bis(cyclohexyl isocyanate), 4,4'-methylene bis(cyclohexyl isocyanate), 3,3'-dimethyl-4,4'-diisocyanate-based biphenyl, 3,3'-dimethoxy-biphenylene diisocyanate, 2,4-bis(b-isocyanate-tert-butyl)toluene, bis(p-b-isocyanate-tert-butyl-phenyl) ether, p-bis(2-methyl-4-isocyanate-phenyl)benzene, 3,3-diisocyanate-tert-adamantane, 3,3-diisocyanate-diadamantane, 3,3-diisocyanate-ethyl-1'-diadamantane, 1,2-bis(3-isocyanate-propoxy)ethane, 2,2-dimethylpropylene diisocyanate, 3-methoxyhexamethylene-1,6-diisocyanate, 2,5-dimethylheptamethyl diisocyanate, 5-methylnonamethylene-1,9-diisocyanate, 1,4-diisocyanate-cyclohexane, 1,2-diisocyanate-octadecane, 2,5-diisocyanate-1,3,4-oxadiazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, and OCN(CH2)3N(CH3)(CH2)3NCO; most preferably, the at least one isocyanate with an NCO functionality of 2.0 is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, octamethylene-1,8-diisocyanate, metaphenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2, 6-Diisocyanate, 2,2'-Biphenylene diisocyanate, 3,3'-Biphenylene diisocyanate, 4,4'-Biphenylene diisocyanate, methylene bis(4-phenylisocyanate), 2,2'-Diphenyl sulfone diisocyanate, 3,3'-Diphenyl sulfone diisocyanate, 4,4'-Diphenyl sulfone diisocyanate, 2,2'-Methylene bis(cyclohexyl isocyanate), 3,3'-Methylene bis(cyclohexyl isocyanate), 4,4'-Methylene bis(cyclohexyl isocyanate), 1,4-Diisocyanate-cyclohexane 1,2-Diisocyanate-octadecane, 2,5-diisocyanate-1,3,4-oxadiazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, and OCN(CH2)3N(CH3)(CH2)3NCO; particularly, the at least one isocyanate with an NCO functionality of 2.0 is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, octamethylene-1,8-diisocyanate, and metaphenylene diisocyanate. Phenylidene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, 2,2'-biphenyl diisocyanate, 3,3'-biphenyl diisocyanate, 4,4'-biphenyl diisocyanate, methylene bis(4-phenylisocyanate), 2,2'-methylene bis(cyclohexyl isocyanate), 3,3'-methylene bis(cyclohexyl isocyanate), 4,4'-methylene bis(cyclohexyl isocyanate), and 1,4-diisocyanate-based cyclohexane and polymeric forms of diisocyanates.

[0249] In another preferred embodiment, the polymeric form of the diisocyanate includes polymeric methylene diphenyl diisocyanate and toluene diisocyanate.

[0250] In another preferred embodiment, the at least one isocyanate contains a carbamate group, an isocyanurate group, a biuret group, a urea diketone group, a ureocarbamate group, and / or an imino group. It exists in the form of dimers, trimers or oligomers of diazine dione groups.

[0251] In another preferred embodiment, the weight-average molecular weight (Mw) of the polyurea copolymer is 500-500,000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight where the polymer material is no longer soluble in standard organic solvents, determined by MALDI-TOF mass spectrometry; more preferably, the weight-average molecular weight (Mw) of the polyurea copolymer is 1000-200,000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight where the polymer material is no longer soluble in standard organic solvents, determined by MALDI-TOF mass spectrometry; even more preferably, the weight-average molecular weight (Mw) of the polyurea copolymer is 2000-100,000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight where the polymer material is no longer soluble in standard organic solvents, determined by MALDI-TOF mass spectrometry; most preferably, the weight-average molecular weight (Mw) of the polyurea copolymer is 3000-80,000 g / mol, determined according to DIN 55672. The molecular weight is determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, by MALDI-TOF mass spectrometry; particularly preferably, the weight-average molecular weight Mw of the polyurea copolymer is 5000-80,000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, by MALDI-TOF mass spectrometry; still even more preferably, the weight-average molecular weight Mw of the polyurea copolymer is 5000-50,000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, by MALDI-TOF mass spectrometry.

[0252] In another preferred embodiment, the molar ratio of NCO in the isocyanate mixture (A) of the polyurea copolymer to -NH- in the secondary amine of at least one formula (B) is ≥1.0:3.0 to ≤3.0:1.0; more preferably, the molar ratio of NCO in the isocyanate mixture (A) of the polyurea copolymer to -NH- in the secondary amine of at least one formula (B) is ≥1.0:2.5 to ≤2.5:1.0; even more preferably, the molar ratio of NCO in the isocyanate mixture (A) of the polyurea copolymer to -NH- in the secondary amine of at least one formula (B) is ≥1.0:2.0 to ≤2.0:1.0; most preferably, the molar ratio of NCO in the isocyanate mixture (A) of the polyurea copolymer to -NH- in the secondary amine of at least one formula (B) is ≥1.0:0.5 to ≤0.5:1.0.

[0253] In another preferred embodiment, the glass transition temperature of the polyurea copolymer is ≥-20°C to ≤250°C, determined according to ASTM D 3418 using a heating rate of 5 K / min; more preferably, the glass transition temperature of the polyurea copolymer is ≥0°C to ≤200°C, determined according to ASTM D 3418 using a heating rate of 5 K / min; even more preferably, the glass transition temperature of the polyurea copolymer is ≥0°C to ≤180°C, determined according to ASTM D 3418 using a heating rate of 5 K / min; most preferably, the glass transition temperature of the polyurea copolymer is ≥20°C to ≤160°C, determined according to ASTM D 3418 using a heating rate of 5 K / min; particularly, the glass transition temperature of the polyurea copolymer is ≥40°C to ≤150°C, determined according to ASTM D 3418 using a heating rate of 5 K / min.

[0254] In another preferred embodiment, the present invention relates to a method for preparing a polyurea copolymer, comprising at least the following steps:

[0255] i) Provide an isocyanate mixture (A) with an average NCO functionality ≥ 2.10;

[0256] ii) Provide at least one secondary amine of formula (B):

[0257]

[0258] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered sub-hetero-alkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylenes, 5-30 membered heterocyclic alkylenes, substituted or unsubstituted C1-C 30 Alkylene C5-C 30Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heterocyclic alkenylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkylene, substituted or unsubstituted C2-C 30 Alkenyl 5-30 membered heterocyclic alkylene, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 aryl and substituted or unsubstituted C2-C 30 Alkenyl 5-30 quinone heteroaryl,

[0259] R b R c R d R e R f and R g Independently selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30 Alkenyl groups, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic alkyl, substituted or unsubstituted 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 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 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0260] R b and R e And the carbon atoms they are bonded to, or

[0261] R c and R f And the carbon atoms they are bonded to, or

[0262] R d and R g And the carbon atoms they are bonded to, or

[0263] R c and R d And the carbon atoms they are bonded to, or

[0264] R c and R b And the carbon atoms they are bonded to, or

[0265] R b and R d And the carbon atoms they are bonded to, or

[0266] R f and R e And the carbon atoms they are bonded to, or

[0267] R e and R g And the carbon atoms they are bonded to, or

[0268] R f and R g and the carbon atoms they are bonded to

[0269] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 member carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, or S as ring members, and

[0270] iii) Make (A) and (B) come into contact;

[0271] More preferably, the method for preparing polyurea copolymers includes at least the following steps:

[0272] i) Provide an isocyanate mixture (A) with an average NCO functionality ≥ 2.10;

[0273] ii) Provide at least one secondary amine of formula (B),

[0274]

[0275] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl and substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 Alpha-aryl

[0276] R b R c R d R e R f and R g Independently selected from 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 C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C30 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0277] R b and R e And the carbon atoms they are bonded to, or

[0278] R c and R f And the carbon atoms they are bonded to, or

[0279] R d and R g And the carbon atoms they are bonded to, or

[0280] R c and R d And the carbon atoms they are bonded to, or

[0281] R c and R b And the carbon atoms they are bonded to, or

[0282] R b and R d And the carbon atoms they are bonded to, or

[0283] R f and R e And the carbon atoms they are bonded to, or

[0284] R e and R g And the carbon atoms they are bonded to, or

[0285] R f and R g and the carbon atoms they are bonded to

[0286] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, or S as ring members; and

[0287] iii) Make (A) and (B) come into contact;

[0288] Most preferably, the method for preparing the polyurea copolymer includes at least the following steps:

[0289] i) Provide an isocyanate mixture (A) with an average NCO functionality ≥ 2.10;

[0290] ii) Provide at least one secondary amine of formula (B):

[0291]

[0292] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkyl 5-30-membered heteroaryl groups and substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 Alpha-aryl

[0293] R b R c R d R e R f and R g Independently selected from 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 C5-C 30 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C6-C30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0294] R b and R e And the carbon atoms they are bonded to, or

[0295] R c and R f And the carbon atoms they are bonded to, or

[0296] R d and R g And the carbon atoms they are bonded to, or

[0297] R c and R d And the carbon atoms they are bonded to, or

[0298] R c and R b And the carbon atoms they are bonded to, or

[0299] R b and R d And the carbon atoms they are bonded to, or

[0300] R f and R e And the carbon atoms they are bonded to, or

[0301] R e and R g And the carbon atoms they are bonded to, or

[0302] R f and R g and the carbon atoms they are bonded to

[0303] Together they form saturated, unsaturated or aromatic, unsubstituted or substituted 5-30 member carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members;

[0304] iii) Make (A) and (B) come into contact;

[0305] Specifically, the method for preparing polyurea copolymers includes at least the following steps:

[0306] i) Provide an isocyanate mixture (A) with an average NCO functionality ≥ 2.10;

[0307] ii) Provide at least one secondary amine of formula (B):

[0308]

[0309] Where Ra Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl and substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 Alpha-aryl

[0310] R b R c R d R e R f and R g Independently selected from 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 C5-C 30 Cycloalkyl and substituted or unsubstituted C6-C 30 Aryl,

[0311] R b and R e And the carbon atoms they are bonded to, or

[0312] R c and R f And the carbon atoms they are bonded to, or

[0313] R d and R g And the carbon atoms they are bonded to, or

[0314] R c and R d And the carbon atoms they are bonded to, or

[0315] R c and R b And the carbon atoms they are bonded to, or

[0316] R b and R dAnd the carbon atoms they are bonded to, or

[0317] R f and R e And the carbon atoms they are bonded to, or

[0318] R e and R g And the carbon atoms they are bonded to, or

[0319] R f and R g and the carbon atoms they are bonded to

[0320] Together they form saturated, unsaturated or aromatic, unsubstituted or substituted 5-30 member carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members;

[0321] iii) Make (A) and (B) come into contact.

[0322] In another preferred embodiment, the molar ratio of NCO in the isocyanate mixture (A) to -NH- in the secondary amine of at least one formula (B) is ≥1.0:3 to ≤3:1.0; more preferably, the molar ratio of NCO in the isocyanate mixture (A) of the polyurea copolymer to -NH- in the secondary amine of at least one formula (B) is ≥1.0:2.5 to ≤2.5:1.0; even more preferably, the molar ratio of NCO in the isocyanate mixture (A) to -NH- in the secondary amine of at least one formula (B) is ≥1.0:2.0 to ≤2.0:1.0; most preferably, the molar ratio of NCO in the isocyanate mixture (A) to -NH- in the secondary amine of at least one formula (B) is ≥1.0:0.5 to ≤0.5:1.0.

[0323] In another preferred embodiment, the molar ratio of NCO in the isocyanate mixture (A) to -NH- in the secondary amine of at least one formula (B) is ≥1.0:0.5 to ≤0.5:1.0.

[0324] In another preferred embodiment, in the method for preparing the polyurea copolymer, step iii) is carried out at a temperature of ≥-50°C to ≤250°C; more preferably, step iii) is carried out at a temperature of ≥0°C to ≤200°C; even more preferably, step iii) is carried out at a temperature of ≥20°C to ≤180°C; most preferably, step iii) is carried out at a temperature of ≥40°C to ≤160°C; particularly, step iii) is carried out at a temperature of ≥60°C to ≤140°C.

[0325] In another preferred embodiment, the method for preparing the polyurea copolymer is carried out in the presence of at least one solvent.

[0326] In another preferred embodiment, the at least one solvent is selected from ketones, esters, aromatic solvents, aliphatic solvents, ethers, lactones, carbonates, sulfones, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, N-methylpyrrolidone, and N-ethylpyrrolidone.

[0327] In another preferred embodiment, the present invention relates to an article comprising a polyurea copolymer.

[0328] In another preferred embodiment, the articles include coatings, repairable coatings, recyclable rigid foam, recyclable flexible foam, automotive parts, recyclable rigid foam, rigid foam insulation, durable resilient wheels and tires, adhesives, surface coatings and surface sealants, synthetic fibers, carpet padding, and hard plastic parts.

[0329] In another preferred embodiment, the present invention relates to a method for reshaping a polyurea copolymer, comprising at least the following steps:

[0330] a) Applying pressure and heat to a polyurea copolymer to obtain a heated polyurea copolymer; and

[0331] b) Molding the heated polyurea copolymer from step a).

[0332] In another preferred embodiment, the method for reshaping polyurea copolymers is ≥5×10 3 Pa to ≤10 7 The test was conducted under a pressure of Pa.

[0333] In another preferred embodiment, the method for reshaping the polyurea copolymer is carried out at a temperature of ≥60°C to ≤300°C.

[0334] This invention is associated with at least one of the following advantages:

[0335] (i) A novel polyurea copolymer with dynamic bonds was developed.

[0336] (ii) A novel polyurea copolymer with recyclability was developed.

[0337] (iii) A novel polyurea copolymer was developed, which has a reaction based solely on polyisocyanates and polyamines.

[0338] A three-dimensional network structure without the use of additional cross-linking agents.

[0339] Implementation plan:

[0340] 1. A polyurea copolymer obtained by reacting a reaction mixture comprising the following components:

[0341] a. Isocyanate mixture (A); and

[0342] b. At least one secondary amine of formula (B):

[0343]

[0344] Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered sub-hetero-alkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylenes, 5-30 membered heterocyclic alkylenes, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heterocyclic alkenylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkylene, substituted or unsubstituted C2-C 30 Alkenyl 5-30 membered heterocyclic alkylene, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 aryl and substituted or unsubstituted C2-C30 Alkenyl 5-30 quinone heteroaryl,

[0345] R b R c R d R e R f and R g Independently selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30 Alkenyl groups, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic alkyl, substituted or unsubstituted 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 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 Alkylenes, 5-30 membered heterocyclic alkyl groups, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups,

[0346] R b and R e And the carbon atoms they are bonded to, or

[0347] R c and R f And the carbon atoms they are bonded to, or

[0348] R d and R g And the carbon atoms they are bonded to, or

[0349] R c and R d And the carbon atoms they are bonded to, or

[0350] R c and R b And the carbon atoms they are bonded to, or

[0351] R b and R d And the carbon atoms they are bonded to, or

[0352] R f and R e And the carbon atoms they are bonded to, or

[0353] R e and R g And the carbon atoms they are bonded to, or

[0354] R f and R g and the carbon atoms they are bonded to

[0355] Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 member carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, or S as ring members; and

[0356] The isocyanate mixture (A) has an average NCO functionality of ≥2.10.

[0357] 2. The polyurea copolymer according to embodiment 1, wherein the isocyanate mixture (A) has an average NCO functionality of ≥2.10 to ≤6.0.

[0358] 3. The polyurea copolymer according to embodiment 1 or 2, wherein R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene and substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 Alpha-aryl.

[0359] 4. The polyurea according to any one of embodiments 1-3, wherein R b R c R d R e R f and R g Independently selected from linear or branched substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C6-C 30 Aryl and substituted or unsubstituted 5-30 membered heteroaryl groups,

[0360] Rb and R e And the carbon atoms they are bonded to, or

[0361] R c and R f And the carbon atoms they are bonded to, or

[0362] R d and R g And the carbon atoms they are bonded to, or

[0363] R c and R d And the carbon atoms they are bonded to, or

[0364] R c and R b And the carbon atoms they are bonded to, or

[0365] R b and R d And the carbon atoms they are bonded to, or

[0366] R f and R e And the carbon atoms they are bonded to, or

[0367] R e and R g And the carbon atoms they are bonded to, or

[0368] R f and R g and the carbon atoms they are bonded to

[0369] Together they form saturated or unsaturated unsubstituted or substituted 5-30 member carbon rings, which contain 0, 1, 2 or 3 heteroatoms selected from O, N or S as ring members.

[0370] 5. The polyurea according to any one of embodiments 1-4, wherein R a R b R c R d R e R f and R g None of them were replaced by -OH.

[0371] 6. The polyurea according to any one of embodiments 1-5, wherein the secondary amine of formula (B) is selected from N1,N3-diisopropyl-4-methylcyclohexane-1,3-diamine, 4-methyl-N1,N3-di-sec-butylcyclohexane-1,3-diamine, 2-methyl-N1,N3-di-sec-butylcyclohexane-1,3-diamine, N1,N3-dibenzyl-2-methylcyclohexane-1,3-diamine, N1,N3-dibenzyl-4-methylcyclohexane-1,3-diamine, N1,N3-bis(2-ethylhexyl)-4-methylcyclohexane-1,3-diamine, N-isopropyl-3-[(isopropylamino)methyl]-3,5,5-trimethylcyclohexylamine, N-sec-butyl-4-[[4- [(sec-butylamino)phenyl]methyl]aniline, N,N'-bis(2,2,6,6-tetramethyl)-4-piperidinyl)hexane-1,6-diamine, N,N'-diethyl-2-butene-1,4-diamine, N,N'-diisopropyl-1,3-propanediamine, N,N'-diisopropylethylenediamine, N,N'-dimethyl-1,3-propanediamine, 1,4,8,11-tetraazacyclotetradecane-5,7-dione, 1,4-diazacycloheptane, 1,2-dimethylethylenediamine, 1,2-diisopropylethylenediamine, N-(pyrrolidine-2-ylmethyl)cyclohexylamine, N-(pyrrolidine-2-ylmethyl)cycloheptylamine, and 2-methyl-N-(pyrrolidine-2-ylmethyl)propane-2-amine.

[0372] 7. The polyurea copolymer according to any one of embodiments 1-6, wherein the isocyanate mixture (A) comprises at least one isocyanate with an NCO functionality ≥ 3.0.

[0373] 8. The polyurea copolymer according to embodiment 7, wherein the at least one isocyanate with an NCO functionality ≥ 3.0 is selected from triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, L-lysine ethyl triisocyanate, 1,6,11-triisocyanate undecane, 2,2-bis[[4-(isocyanate-methyl)phenyl]methyl]butyl-n-[[4-(isocyanate-methyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-trimethyl)tri(hexamethylene) Triisocyanates, 1,3,5-triisocyanate-based benzene, tri(isocyanate-based hexyl) biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyltri(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-based dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4'-diphenyl ether triisocyanate, and diisocyanates and triisocyanates in polymeric forms.

[0374] 9. The polyurea copolymer according to any one of embodiments 1-8, wherein the isocyanate mixture (A) comprises at least one isocyanate with an NCO functionality of 2.0.

[0375] 10. The polyurea copolymer according to embodiment 9, wherein the at least one isocyanate with an NCO functionality of 2.0 is selected from isophorone diisocyanate, propylene-1,2-diisocyanate, propylene-1,3-diisocyanate, butylene-1,2-diisocyanate, butylene-1,3-diisocyanate, hexamethylene-1,6-diisocyanate, 2-methylpentamethylene-1,5-diisocyanate, 2-ethylbutylene-1,4-diisocyanate, 1,5-pentamethylene diisocyanate, methyl-2,6-diisocyanate hexanoate, octamethylene-1,8-diisocyanate, 2,4,4-trimethylhexamethylene-1,6-diisocyanate, nonamethylene diisocyanate, 2,2,4-trimethylhexamethylene Methyl-1,6-diisocyanate, decamethyl-1,10-diisocyanate, 2,11-diisocyanate-dodecane, metaphenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, methylpropylphenyl diisocyanate, methylethylphenyl diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, methylene bis(4-phenylisocyanate), ethyl bis(4-phenylisocyanate), isopropyl bis(4-phenylene) Isocyanates), butylene bis(4-phenylisocyanate), 2,2'-oxydiphenyl diisocyanate, 3,3'-oxydiphenyl diisocyanate, 4,4'-oxydiphenyl diisocyanate, 2,2'-ketodiphenyl diisocyanate, 3,3'-ketodiphenyl diisocyanate, 4,4'-ketodiphenyl diisocyanate, 2,2'-mercaptodiphenyl diisocyanate, 3,3'-mercaptodiphenyl diisocyanate, 4,4'-thiodiphenyl diisocyanate, 2,2'-diphenyl sulfone diisocyanate, 3,3'-diphenyl sulfone diisocyanate, 4,4'-diphenyl sulfone diisocyanate, 2,2'-methylene bis(cyclohexyl isocyanate), 3,3'-methylene bis(cyclohexyl isocyanate), 4,4' -Methylene bis(cyclohexyl isocyanate), 4,4'-ethylene bis(cyclohexyl isocyanate), 4,4'-propylene bis-(cyclohexyl isocyanate), bis(p-isocyanate-cyclohexyl) sulfone, bis(p-isocyanate-cyclohexyl) ether, bis(p-isocyanate-cyclohexyl) diethylsilane, bis(p-isocyanate-cyclohexyl) diphenylsilane, bis(p-isocyanate-cyclohexyl) ethylphosphine oxide, bis(p-isocyanate-cyclohexyl) phenylphosphine oxide, bis(p-isocyanate-cyclohexyl) N-phenylamine, bis(p-isocyanate-cyclohexyl) N-methylamine, 3,3'-dimethyl-4,4'-diisocyanate-biphenyl, 3,3'-dimethoxy-biphenyl diisocyanate, 2,4-Bis(β-isocyanate-tert-butyl)toluene, bis(p-β-isocyanate-tert-butyl-phenyl) ether, p-bis(2-methyl-4-isocyanate-phenyl)benzene, 3,3-diisocyanate-based adamantane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-based propoxy)ethane, 2,2-dimethylpropylene diisocyanate, 3-methoxyhexamethylene-1 6-Diisocyanate, 2,5-dimethylheptamethylene diisocyanate, 5-methylnonamethylene-1,9-diisocyanate, 1,4-diisocyanate-cyclohexane, 1,2-diisocyanate-octadecane, 2,5-diisocyanate-1,3,4-oxadiazole, OCN(CH2)3O(CH2)2O(CH2)3NCO and OCN(CH2)3N(CH3)(CH2)3NCO, as well as diisocyanates in polymeric forms.

[0376] 11. The polyurea copolymer according to any one of embodiments 1-10, wherein the at least one isocyanate contains a urethane group, an isocyanurate group, a biuret group, a urea diketone group, a ureocarbamate group, and / or an imino group. It exists in the form of dimers, trimers or oligomers of diazine dione groups.

[0377] 12. The product according to embodiments 1-11, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:10 to ≤10:1.0.

[0378] 13. The product according to embodiment 12, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:2.5 to ≤2.5:1.0.

[0379] 14. The product according to embodiment 13, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:2.0 to ≤2.0:1.0.

[0380] 15. The product according to embodiments 1-14, wherein the weight-average molecular weight Mw of the polyurea copolymer is 3000-80.000 g / mol, as determined according to DIN 55672.

[0381] 16. The product according to embodiment 15, wherein the weight-average molecular weight Mw of the polyurea copolymer is 3000-50,000 g / mol, as determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

[0382] 17. The product according to embodiment 16, wherein the weight-average molecular weight Mw of the polyurea copolymer is 5000-20.000 g / mol, as determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

[0383] 18. A method for preparing a polyurea copolymer according to any one of embodiments 1-17, comprising at least the following steps:

[0384] i) Provide an isocyanate mixture (A) with an average NCO functionality ≥ 2.10;

[0385] ii) Provide at least one secondary amine of formula (B):

[0386]

[0387] Where R a R b R c R d R e R f and R g As defined in any of the implementation schemes 1-10, and iii) make contact between (A) and (B).

[0388] 19. The method according to embodiment 18, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:10 to ≤10:1.0.

[0389] 20. The method according to embodiment 19, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:2.5 to ≤2.5:1.0.

[0390] 21. The method according to embodiment 20, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:0.5 to ≤0.5:1.0.

[0391] 22. The method according to any one of embodiments 18-21, wherein step iii) is carried out at a temperature of ≥-50°C to ≤250°C.

[0392] 23. The method according to any one of 18-22, wherein step iii) is carried out in the presence of at least one solvent.

[0393] 24. The method according to embodiment 23, wherein the at least one solvent is selected from ketones, esters, aromatic solvents, aliphatic solvents, ethers, lactones, carbonates, sulfones, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, N-methylpyrrolidone, and N-ethylpyrrolidone.

[0394] 25. An article comprising a polyurea copolymer according to any one of 1-17 or a polyurea copolymer obtained according to any one of 18-21.

[0395] 26. A method for remolding a polyurea copolymer according to any one of embodiments 1-17, or a polyurea copolymer obtained according to any one of embodiments 18-21, or an article according to embodiment 25, comprising at least the following steps:

[0396] a) Applying pressure and heating to a polyurea copolymer to obtain a heated polyurea copolymer; and

[0397] b) Molding the heated polyurea copolymer from step a).

[0398] 27. The method according to implementation scheme 26, wherein the pressure is ≥5×10 3 Pa to ≤10 7 Pa.

[0399] 28. The method according to implementation plan 27, wherein the temperature is ≥60°C to ≤300°C.

[0400] Although the invention has been described with reference to its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the invention. Example

[0401] Material

[0402] PMDI (Lupranat M20 FB) was obtained from BASF; 4,4'-methylenebis(N-sec-butylaniline) (“DIB-MDA”) was purchased from ABCR. MCDA and T5 amine were obtained from BASF. Unless otherwise stated, all other chemicals were obtained from Sigma-Aldrich (Germany) and used as is. The modified MCDA-amine and DIP-IPDA were synthesized in our laboratory by reductive amination (procedure below). THF was dried using molecular sieve (4A).

[0403] PMDI: Polydiphenylmethane diisocyanate.

[0404] MCDA: A mixture of 4-methylcyclohexane-1,3-diamine and 2-methylcyclohexane-1,3-diamine, and all possible stereoisomers.

[0405] DIP-MCDA: A mixture of N1,N3-diisopropyl-4-methylcyclohexane-1,3-diamine and N1,N3-diisopropyl-2-methylcyclohexane-1,3-diamine, and all possible stereoisomers.

[0406] Bbz-MCDA: A mixture of N1,N3-dibenzyl-4-methylcyclohexane-1,3-diamine and N1,N3-dibenzyl-2-methylcyclohexane-1,3-diamine, and all possible stereoisomers.

[0407] EtHex-MCDA: A mixture of N1,N3-bis(2-ethylhexyl)-4-methylcyclohexane-1,3-diamine and N1,N3-bis(2-ethylhexyl)-2-methylcyclohexane-1,3-diamine, and all possible stereoisomers.

[0408] DIP-IPDA: N-isopropyl-3-[(isopropylamino)methyl]-3,5,5-trimethylcyclohexylamine.

[0409] DIB-MCDA: A mixture of N1,N3-di-sec-butyl-4-methylcyclohexane-1,3-diamine and N1,N3-di-sec-butyl-2-methylcyclohexane-1,3-diamine, and all possible stereoisomers.

[0410] DIB-MDA: N-sec-butyl-4-[[4-(sec-butylamino)phenyl]methyl]aniline.

[0411] T5-amine: N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)hexane-1,6-diamine.

[0412] method

[0413] The DSC is used to determine the reaction enthalpy and glass transition temperature according to ASTM D 3418 using a heating rate of 5 K / min.

[0414] The residual NCO content was determined by IR spectroscopy.

[0415] The TGA spectra were obtained in a gold crucible under N2 atmosphere according to ASTM E1131 and ISO 11358.

[0416] Thermoforming method

[0417] Test method:

[0418] The polymer powder / particles obtained according to the examples are transferred to a hot press. The polymer powder is then reformed into a solid biscuit-shaped plate when a pressure of 20 kN and a temperature of 160-180°C are applied for at least 5 minutes.

[0419] The polymer powder obtained according to the present invention was reshaped into biscuits / boards. Conversely, when the polymer powder obtained according to the comparative example was used, no solid biscuits / boards were obtained. Instead, due to the lack of ductility of the comparative material, it remained a white, opaque solid and easily crumbled.

[0420] Synthesis of MCDA-based secondary amines:

[0421] N 1 N 3 -Diisopropyl-4-methylcyclohexane-1,3-diamine (DiP-MCDA)

[0422]

[0423] Under a nitrogen atmosphere, TiO2 (75 g, 10 wt%) was loaded into a 3.5 L steel autoclave and suspended in MCDA (730 g, 5.70 mol, 1.0 equivalent). Acetone (1322 g, 1674 mL, 22.8 mol, 4.0 equivalent) was then added dropwise at 100 °C and stirred for 8 hours, followed by filtration. The remaining yellow crude diimide was transferred to a 3.5 L steel autoclave and suspended in a [Pd] catalyst (75 g, 10 wt%) supported on Al2O3. The system was then introduced into a 100 bar H2 atmosphere and stirred for 8 hours. After complete conversion as monitored by GC, the system was cooled to room temperature and purged with nitrogen. The volatiles were then removed under reduced pressure, and the crude compound was purified by vacuum distillation (boiling point 126 °C; 20 mbar) to obtain a colorless oily product of the desired target compound (1170 g, 84% yield, >99.5% purity).

[0424] analyze:

[0425] GC(DB1 column, 30m; 100℃ (12 minutes), 10℃ / minute, 250℃ (8 minutes): t R = 19.79 minutes.

[0426] Example 4:

[0427] Polymerized methylene diphenyl isocyanate (pMDI) (16.52 g, f = 2.53) and THF (250 g) were placed in a flask and cooled in an ice bath. Stericobacted secondary diamine DIP-MCDA (13 g) in 50 g of THF was slowly added to form a polyurea. After stirring for 1 hour, the reaction mixture was heated to room temperature. Stirring continued until polymerization was complete, as confirmed by the disappearance of the NCO band in IR spectroscopy. The THF was evaporated under reduced pressure. The resulting material was crushed and dried under reduced pressure to remove trace amounts of residual THF. The product was obtained in quantitative yield as a pale yellow solid.

[0428] Example 12:

[0429] Polymerized methylene diphenyl isocyanate (pMDI) (16.52 g, f = 2.53) and THF (250 g) were placed in a flask and cooled in an ice bath. A sterically hindered secondary diamine, N-sec-butyl-4-[[4-(sec-butylamino)phenyl]methyl]aniline (19.02 g), in 50 g of THF was slowly added to form a polyurea. After stirring for 1 hour, the reaction mixture was heated to room temperature. Stirring continued until polymerization was complete, as confirmed by the disappearance of the NCO band in IR spectroscopy. The THF was evaporated under reduced pressure. The resulting material was crushed and dried under reduced pressure to remove trace amounts of residual THF. The product was obtained in quantitative yield as a pale yellow solid.

[0430] result

[0431] Table 1

[0432]

[0433] Table 2

[0434]

[0435] a. PMDI isocyanate

[0436] b. PMDI: Secondary amine ratio 0.8:1.0

[0437] c. The ratio of NCO to secondary amine is 1.0:1.0

[0438] Comparative experiment:

[0439]

[0440] Thermosetting plastics are the preferred material for many applications due to their stability, mechanical properties, and chemical resistance—properties stemming from their permanently cross-linked molecular networks. However, unlike thermoplastics, thermosetting plastics cannot be thermoformed and are therefore less recyclable.

[0441] This invention provides a novel class of recyclable polyurea copolymers. As can be clearly seen from the above embodiments, the use of polymeric diisocyanate results in the formation of recyclable polyurea copolymers with a three-dimensional network structure of dynamic urea bonds. The introduction of such exchangeable chemical bonds is an attractive chemical strategy for combining the stability of thermosetting materials with the processability of thermoplastics.

[0442] In contrast to existing technologies, this material does not require additional crosslinking agents such as trifunctional alcohols / amines, etc. Instead, crosslinking is achieved by using isocyanates with a functionality >2.0 (≥2.1).

Claims

1. A thermo-reformable polyurea copolymer obtained by reacting a reaction mixture comprising the following components: a. Isocyanate mixture (A); and b. At least one secondary amine of formula (B) Formula (B); Where R a Selected from substituted or unsubstituted linear or branched C1-C 30 Alkylene, substituted or unsubstituted straight-chain or branched 2-30-membered heteroalkylene, substituted or unsubstituted straight-chain or branched C2-C 30 Sub-alkenyl groups, substituted or unsubstituted straight-chain or branched 3-30-membered sub-hetero-alkenyl groups, substituted or unsubstituted C5-C 30 Cycloalkylene, substituted or unsubstituted 5-30 membered heterocycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5-30 membered heterocyclic cycloalkenyl, substituted or unsubstituted C6-C 30 arylene, substituted or unsubstituted 5-30 quinone heteroarylene, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C5-C 30 Cycloalkyl C1-C 30 Alkylene C5-C 30 Cycloalkylene, substituted or unsubstituted C1-C 30 Alkylenes, 5-30 membered heterocyclic alkylenes, substituted or unsubstituted C1-C 30 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heterocyclic alkenylene, substituted or unsubstituted C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C6-C 30 Alpha-aryl C1-C 30 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 30 Alkylene 5-30-membered heteroaryl, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkylene, substituted or unsubstituted C2-C 30 Alkenyl 5-30 membered heterocyclic alkylene, substituted or unsubstituted C2-C 30 Sub-alkenyl C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl 5-30 membered heterocyclic alkenyl, substituted or unsubstituted C2-C 30 Sub-alkenyl C6-C 30 aryl and substituted or unsubstituted C2-C 30 Alkenyl 5-30 quinone heteroaryl, R b R c R d R e R f and R g Independently selected from 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 C5-C 30 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5-30-membered heteroaryl groups, R b and R e And the carbon atoms they are bonded to, or R c and R f And the carbon atoms they are bonded to, or R d and R g And the carbon atoms they are bonded to, or R c and R d And the carbon atoms they are bonded to, or R c and R b And the carbon atoms they are bonded to, or R b and R d And the carbon atoms they are bonded to, or R f and R e And the carbon atoms they are bonded to, or R e and R g And the carbon atoms they are bonded to, or R f and R g and the carbon atoms they are bonded to Together they form saturated, unsaturated, or aromatic, unsubstituted or substituted 5-30 membered carbon rings, containing 0, 1, 2, or 3 heteroatoms selected from O, N, and S as ring members; and The isocyanate mixture (A) has an average NCO functionality of ≥2.10 to ≤6.0; The isocyanate mixture (A) is a crosslinking agent and the reaction mixture does not contain any crosslinking agents other than the isocyanate mixture (A). The secondary amine in formula (B) is selected from N1,N3-diisopropyl-4-methylcyclohexane-1,3-diamine, 4-methyl-N1,N3-di-sec-butylcyclohexane-1,3-diamine, 2-methyl-N1,N3-di-sec-butylcyclohexane-1,3-diamine, N1,N3-dibenzyl-2-methylcyclohexane-1,3-diamine, N1,N3-dibenzyl-4-methylcyclohexane-1,3-diamine, N1,N3-bis(2-ethylhexyl)-4-methylcyclohexane-1,3-diamine, N-isopropyl-3-[(isopropylamino)methyl]-3,5,5-trimethylcyclohexylamine, N-sec-butyl-4-[[4-(sec-butylamino)phenyl]methyl [By] aniline, N,N'-bis(2,2,6,6-tetramethyl)-4-piperidinyl)hexane-1,6-diamine, N,N'-diethyl-2-butene-1,4-diamine, N,N'-diisopropyl-1,3-propanediamine, N,N'-diisopropylethylenediamine, N,N'-dimethyl-1,3-propanediamine, 1,4,8,11-tetraazacyclotetradecane-5,7-dione, 1,4-diazacycloheptane, 1,2-dimethylethylenediamine, 1,2-diisopropylethylenediamine, N-(pyrrolidine-2-ylmethyl)cyclohexylamine, N-(pyrrolidine-2-ylmethyl)cycloheptamine, and 2-methyl-N-(pyrrolidine-2-ylmethyl)propane-2-amine.

2. The polyurea copolymer according to claim 1, wherein the isocyanate mixture (A) comprises at least one isocyanate with an NCO functionality ≥ 3.

0.

3. The polyurea copolymer according to claim 2, wherein the at least one isocyanate with an NCO functionality ≥ 3.0 is selected from triphenylmethane-4,4',4''-triisocyanate, toluene-2,4,6-triyltriisocyanate, L-lysine ethyl triisocyanate, 1,6,11-triisocyanate undecane, 2,2-bis[[4-(isocyanate-methyl)phenyl]methyl]butyl-n-[[4-(isocyanate-methyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)tri(hexamethylene) Triisocyanates, 1,3,5-triisocyanate-based benzene, tri(isocyanate-based hexyl) biuret, 3,3',3''-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyltri(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-based dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4'-diphenyl ether triisocyanate, and diisocyanates and triisocyanates in polymeric forms.

4. The polyurea copolymer according to any one of claims 1-3, wherein the isocyanate mixture (A) comprises at least one isocyanate with an NCO functionality of 2.

0.

5. The polyurea copolymer according to claim 4, wherein the at least one isocyanate with an NCO functionality of 2.0 is selected from isophorone diisocyanate, propylene-1,2-diisocyanate, propylene-1,3-diisocyanate, butylene-1,2-diisocyanate, butylene-1,3-diisocyanate, hexamethylene-1,6-diisocyanate, 2-methylpentamethylene-1,5-diisocyanate, 2-ethylbutylene-1,4-diisocyanate, 1,5-pentamethylene diisocyanate, methyl-2,6-diisocyanate hexanoate, octamethylene-1,8-diisocyanate, 2,4,4-trimethylhexamethylene-1,6-diisocyanate, nonamethylene diisocyanate, 2,2,4-trimethylhexamethylene 1,6-diisocyanate, decamethyl-1,10-diisocyanate, 2,11-diisocyanate-dodecane, metaphenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, methylpropylbenzene diisocyanate, methylethylbenzene diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, methylene bis(4-phenylisocyanate), ethylene bis(4-phenylisocyanate), isopropylene bis(4-phenylisocyanate) cyanide ester), butylene bis(4-phenylisocyanate), 2,2'-oxydiphenyl diisocyanate, 3,3'-oxydiphenyl diisocyanate, 4,4'-oxydiphenyl diisocyanate, 2,2'-ketodiphenyl diisocyanate, 3,3'-ketodiphenyl diisocyanate, 4,4'-ketodiphenyl diisocyanate, 2,2'-mercaptodiphenyl diisocyanate, 3,3'-mercaptodiphenyl diisocyanate, 4,4'-thiodiphenyl diisocyanate, 2,2'-diphenyl sulfone diisocyanate, 3,3'-diphenyl sulfone diisocyanate, 4,4'-diphenyl sulfone diisocyanate, 2,2'-methylene bis(cyclohexyl isocyanate), 3,3'-methylene bis(cyclohexyl isocyanate), 4,4'- Methylene bis(cyclohexyl isocyanate), 4,4'-ethylidene bis(cyclohexyl isocyanate), 4,4'-propylidene bis-(cyclohexyl isocyanate), bis(p-isocyanate-cyclohexyl) sulfide, bis(p-isocyanate-cyclohexyl) sulfone, bis(p-isocyanate-cyclohexyl) ether, bis(p-isocyanate-cyclohexyl) diethylsilane, bis(p-isocyanate-cyclohexyl) diphenylsilane, bis(p-isocyanate-cyclohexyl) ethylphosphine oxide, bis(p-isocyanate-cyclohexyl) phenylphosphine oxide, bis(p-isocyanate-cyclohexyl) N-phenylamine, bis(p-isocyanate-cyclohexyl) N-methylamine, 3,3'-dimethyl-4,4'-diisocyanate-biphenyl, 3,3'-dimethoxy-biphenyl diisocyanate, 2,4-Bis(β-isocyanate-tert-butyl)toluene, bis(p-β-isocyanate-tert-butyl-phenyl) ether, p-bis(2-methyl-4-isocyanate-phenyl)benzene, 3,3-diisocyanate-based adamantane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-based propoxy)ethane, 2,2-dimethylpropylene diisocyanate, 3-methoxy Hexamethylene-1,6-diisocyanate, 2,5-dimethylheptamethyl diisocyanate, 5-methylnonamethylene-1,9-diisocyanate, 1,4-diisocyanate-cyclohexane, 1,2-diisocyanate-octadecane, 2,5-diisocyanate-1,3,4-oxadiazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, and OCN(CH2)3N(CH3)(CH2)3NCO.

6. The polyurea copolymer according to any one of claims 1-3, wherein the at least one isocyanate contains a urethane group, a biuret group, a ureidone group, a ureocarbamate group, and / or an imino group. It exists in the form of dimers, trimers or oligomers of diazine dione groups.

7. The polyurea copolymer according to claim 6, wherein the isocyanate mixture (A) comprises an isocyanate having a carbamate group, a biuret group, a ureidone group, a ureocarbamate group, and / or an imino group. It exists in the form of dimers, trimers or oligomers of diazine dione groups.

8. The polyurea copolymer according to any one of claims 1-3, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:10 to ≤10:1.

0.

9. The polyurea copolymer according to claim 8, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:2.5 to ≤2.5:1.

0.

10. The polyurea copolymer according to claim 9, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:2.0 to ≤2.0:1.

0.

11. The polyurea copolymer according to any one of claims 1-3, wherein the weight-average molecular weight Mw of the polyurea copolymer is 3000-80.000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

12. The polyurea copolymer according to claim 11, wherein the weight-average molecular weight Mw of the polyurea copolymer is 3000-50.000 g / mol, as determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

13. The polyurea copolymer according to claim 12, wherein the weight-average molecular weight Mw of the polyurea copolymer is 5000-20.000 g / mol, as determined according to DIN 55672, or, in the case of a high molecular weight polymer material that is no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

14. A method for preparing a polyurea copolymer according to any one of claims 1-13, comprising at least the following steps: i) Provide an isocyanate mixture (A) with an average NCO functionality of ≥2.10 to ≤6.0; ii) Provide at least one secondary amine of formula (B): Formula (B); Where R a R b R c R d R e R f and R g As defined in any one of claims 1-10, and iii) Make (A) and (B) come into contact; The isocyanate mixture (A) is a crosslinking agent and the reaction mixture does not contain any crosslinking agents other than the isocyanate mixture (A).

15. The method according to claim 14, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:10 to ≤10:1.

0.

16. The method according to claim 15, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:2.5 to ≤2.5:1.

0.

17. The method according to claim 16, wherein the molar ratio of NCO to secondary amine (B) in the isocyanate mixture (A) is ≥1.0:0.5 to ≤0.5:1.

0.

18. The method according to any one of claims 14-17, wherein step iii) is carried out at a temperature of ≥-50°C to ≤250°C.

19. The method according to any one of claims 14-17, wherein step iii) is carried out in the presence of at least one solvent.

20. The method of claim 19, wherein the at least one solvent is selected from ketones, esters, aromatic solvents, aliphatic solvents, ethers, lactones, carbonates, sulfones, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, N-methylpyrrolidone, and N-ethylpyrrolidone.

21. An article comprising a polyurea copolymer according to any one of 1-13 or a polyurea copolymer obtained according to any one of 14-20.

22. A method for remolding a polyurea copolymer according to any one of claims 1-13, or a polyurea copolymer obtained according to any one of claims 14-20, or an article according to claim 21, comprising at least the following steps: a) Applying pressure and heating to a polyurea copolymer to obtain a heated polyurea copolymer; and b) Molding the heated polyurea copolymer from step a).

23. The method according to claim 22, wherein the pressure is ≥5 × 10⁻⁶. 3 Pa to ≤10 7 Pa.

24. The method of claim 23, wherein the temperature is ≥60°C to ≤300°C.

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