Polyurea copolymer

Abstract

The present invention relates to a polyurea-polyetheramine copolymer obtained by reacting at least one polyisocyanate (A) and at least one isocyanate reactive component (B); wherein the at least one polyisocyanate (A) has an NCO functionality of at least ≥2.0; and the at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group.

Description

Invention Field

[0001] The present invention relates to a polyurea-polyetheramine copolymer obtained by reacting at least one polyisocyanate (A) and at least one isocyanate reactive component (B); wherein the at least one polyisocyanate (A) has an NCO functionality of at least ≥2.0; and the at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group. 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] US2007 / 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] US2016 / 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] US2017 / 327627A1 discloses a stretchable, repairable, and reprogrammable shape memory polymer with hindered urea bonds.

[0010] The above-described prior art describes the formation of linear polyurea polymers.

[0011] The purpose of this invention is to provide a polyurea polymer with a three-dimensional network structure.

[0012] Another object of the present invention is to provide a recyclable three-dimensional network polyurea copolymer. Invention Overview

[0014] The objective is achieved by reacting at least one polyisocyanate (A) and at least one isocyanate reactive component (B); wherein the at least one polyisocyanate (A) has an NCO functionality of at least ≥2.0; and the at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group.

[0015] Therefore, in a first aspect, the present invention relates to polyurea copolymers obtained by reacting the following substances:

[0016] a. at least one polyisocyanate (A); and

[0017] b. At least one isocyanate reactive component (B);

[0018] The at least one polyisocyanate (A) has an NCO functionality of at least 2.0; and the at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3) and formula (B4):

[0019]

[0020] in:

[0021] R a R b R c R g R m and R e Independently selected from linear 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; in each case substituted with at least one hydroxyl functional group;

[0022] R d 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 30Cycloalkenyl, 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, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0023] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0024] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0025] n is an integer between 1 and 1000;

[0026] w is an integer between 0 and 30;

[0027] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t + x + y + z is an integer from 1 to 3000.

[0028] In a second aspect, the present invention relates to a method for preparing the polyurea copolymer described herein, comprising at least the following steps:

[0029] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0030] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0031] The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group.

[0032] In a third aspect, the present invention relates to an article comprising the polyurea copolymer described herein.

[0033] In a fourth aspect, the present invention relates to a method for reshaping polyurea copolymers, comprising at least the following steps:

[0034] a) Applying pressure and heat to the polyurea copolymer described herein to obtain a heated polyurea copolymer; and

[0035] b) Reshape the polyurea copolymer from step a). Invention Details

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] In a first embodiment, the present invention relates to a polyurea copolymer obtained by reacting the following substances:

[0044] a. at least one polyisocyanate (A); and

[0045] b. At least one isocyanate reactive component (B);

[0046] The at least one polyisocyanate (A) has an NCO functionality of at least 2.0; and the at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4).

[0047]

[0048]

[0049] in:

[0050] R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 30Alkyl, 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; in each case substituted with at least one hydroxyl functional group;

[0051] R d 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 30Aryl and substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0052] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0053] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0054] n is an integer between 1 and 1000;

[0055] w is an integer between 0 and 30;

[0056] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t + x + y + z is between 1 and 3000.

[0057] More preferably, the polyurea copolymer is obtained by the following reaction:

[0058] a. at least one polyisocyanate (A); and

[0059] b. At least one isocyanate reactive component (B);

[0060] The at least one polyisocyanate (A) has an NCO functionality of at least 2.0; and the at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3) and formula (B4):

[0061]

[0062]

[0063] in:

[0064] R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 30Alkyl, 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; in each case substituted with at least one hydroxyl functional group;

[0065] R d 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 30Aryl and substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0066] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0067] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0068] n is an integer between 1 and 1000;

[0069] w is an integer between 0 and 30;

[0070] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t + x + y + z is an integer from 1 to 3000.

[0071] In another preferred embodiment, the at least one polyisocyanate (A) has an average NCO functionality of ≥2.0 to ≤6.0; more preferably, the at least one polyisocyanate (A) has an average NCO functionality of ≥2.0 to ≤5.0; even more preferably, the at least one polyisocyanate (A) has an average NCO functionality of ≥2.0 to ≤4.0; most preferably, the at least one polyisocyanate (A) has an average NCO functionality of ≥2.0 to ≤3.5; particularly, the at least one polyisocyanate (A) has an average NCO functionality of ≥2.0 to ≤3.0.

[0072] In another preferred embodiment, the at least one polyisocyanate (A) 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, decamethylene diisocyanate, etc. Methyl-1,10-diisocyanate, 2,11-diisocyanate-dodecane, m-phenylene 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), butylene-bis(4-phenylisocyanate) 2,2'-phenyl isocyanate, 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) cyanate), 4,4'-ethylene-bis(cyclohexyl isocyanate), 4,4'-propylene-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 aragonane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-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-, Diazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, OCN(CH2)3N(CH3)(CH2)3NCO, triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-triyltriisocyanate, ethyl l-lysine 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)bis(hexamethylene)isocyanate, 1,3,5-triisocyanate benzene, bis(isocyanate hexyl) biuret, 3,3 ',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-trimethylbis(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates; more preferably, the at least one polyisocyanate (A) 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, 2,2,4-trimethylhexamethylene-1,6-diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, methylene-bis(4-phenylisocyanate) 2,2'-oxydiphenyl diisocyanate, 3,3'-oxydiphenyl diisocyanate, 4,4'-oxydiphenyl 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, 3,3'-dimethyl-4,4'-Diisocyanate-based biphenyl, 3,3'-dimethoxy-biphenyl 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-based benzothane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-propoxy)ethane, 1,4-diisocyanate-based cyclohexane, OCN(CH2)3O(CH2)2O(CH2)3NCO, OCN(CH2)3N(CH3)(CH2)3NCO, triphenylmethane-4,4',4”-triisocyanate Ester, Toluene-2,4,6-trimethyltriisocyanate, L-lysine triisocyanate ethyl ester, 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)bis(hexamethylene)isocyanate, 1,3,5-triisocyanate phenyl, bis(isocyanate hexyl) biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-trimethylbis(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates; even more preferably, the at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, octamethylene-1,8-diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'- Biphenyl diisocyanate, 3,3'-biphenyl diisocyanate, 4,4'-biphenyl diisocyanate, 3,3'-dimethyl-4,4'-biphenyl diisocyanate, methylene-bis(4-phenyl isocyanate), 2,2'-oxydiphenyl diisocyanate, 3,3'-oxydiphenyl diisocyanate, 4,4'-oxydiphenyl 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), bis(p-isocyanate-cyclohexyl) ether, 1,4-Diisocyanate-cyclohexane, OCN(CH2)3O(CH2)2O(CH2)3NCO, OCN(CH2)3N(CH3)(CH2)3NCO, triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-triyltriisocyanate, ethyl l-lysine 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)bis(hexamethylene)isocyanate, 1,3,5-triisocyanate-benzene, bis(isocyanate-hexyl) Biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-trimethylbis(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates; most preferably, the at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, octamethylene-1,8-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), bis(p-isocyanate-cyclohexyl) ether, 1,4-diisocyanate-cyclohexane, OCN(CH2)3O(CH2)2O(CH2)3NCO, OCN(CH2)3N(CH3)(CH2)3NCO, triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6- Trimethyl triisocyanate, L-lysine triisocyanate ethyl ester, 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)bis(hexamethylene)isocyanate, 1,3,5-triisocyanate phenyl, bis(isocyanate hexyl) biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-trimethylbis(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-Triisocyanate, 2,4,4'-Triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates; particularly, the at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, octamethylene-1,8-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'-methylene-bis(4-phenylisocyanate). (cyclohexyl isocyanate), 3,3'-methylene-bis(cyclohexyl isocyanate), 4,4'-methylene-bis(cyclohexyl isocyanate), 1,4-diisocyanate-cyclohexane, triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-triyltriisocyanate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)bis(hexamethylene)isocyanate, 1,3,5-triisocyanate-benzene, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates.

[0073] In another preferred embodiment, the at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, etc. Biphenyl diisocyanate, 3,3'-dimethyl-4,4'-biphenyl diisocyanate, methylene-bis(4-phenyl isocyanate), 2,2'-methylene-bis(cyclohexyl isocyanate), 3,3'-methylene-bis(cyclohexyl isocyanate), 4,4'-methylene-bis(cyclohexyl isocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanate-phenylene, and diisocyanates and triisocyanates in polymeric forms.

[0074] In another preferred embodiment, the polymeric forms of diisocyanates and triisocyanates represent isocyanates existing in dimer, trimer, and oligomer structures.

[0075] In another preferred embodiment, the at least one polyisocyanate (A) 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 and oligomers of diazine dione.

[0076] In another preferred embodiment, the at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4):

[0077]

[0078]

[0079] in:

[0080] R a R b R c R g R m and R e Independently selected from linear 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; in each case substituted with at least one hydroxyl functional group;

[0081] R d Selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C30 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, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0082] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0083] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0084] n is an integer between 1 and 1000;

[0085] w is an integer between 0 and 30;

[0086] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t + x + y + z is between 1 and 3000.

[0087] More preferably,

[0088] Ra R b R c R g R m and R e Independently selected from linear 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; in each case substituted with at least one hydroxyl functional group;

[0089] R d 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 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-C30 aryl, substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0090] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0091] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, methyl, ethyl, and propyl.

[0092] n is an integer from 1 to 500;

[0093] w is an integer between 0 and 10;

[0094] t, x, y, and z are independent integers from 0 to 500, provided that the sum of t + x + y + z is between 1 and 1500.

[0095] Even more preferably,

[0096] R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 20 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 20 Alkenyl, substituted or unsubstituted straight-chain or branched 2-20 heteroalkyl groups, substituted or unsubstituted C5-C 20 cycloalkyl, substituted or unsubstituted C6-C 20 aryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-10 membered heterocyclic alkyl, substituted or unsubstituted C1-C 10 alkylene 5-20 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 20 Aryl and substituted or unsubstituted C1-C 10Alkylene 5-20-membered heteroaryl; in each case substituted with at least one hydroxyl functional group;

[0097] R d 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 C1-C 10 Alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0098] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, methyl, ethyl, and propyl.

[0099] n is an integer between 1 and 300;

[0100] w is an integer between 0 and 5;

[0101] t, x, y, and z are independent integers from 0 to 300, provided that the sum of t + x + y + z is between 1 and 900.

[0102] Most preferably,

[0103] R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 15 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 15 Alkenyl, substituted or unsubstituted C5-C 15 cycloalkyl, substituted or unsubstituted C6-C 10 aryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 15 Cycloalkyl and substituted or unsubstituted C1-C 10 Alkylene C6-C 15 aryl group; in each case, it is substituted with at least one hydroxyl functional group;

[0104] R d 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 and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0105] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0106] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, methyl, ethyl, and propyl.

[0107] n is an integer between 1 and 100;

[0108] w is an integer between 1 and 3;

[0109] t, x, y, and z are independent integers from 0 to 100, provided that the sum of t + x + y + z is between 1 and 300.

[0110] In particular,

[0111] R a R b R c R g R m and R e 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 group; in each case, it is substituted with at least one hydroxyl functional group;

[0112] R d 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-C30 Aryl and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0113] R h and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0114] R j and R f -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0115] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen and methyl;

[0116] n is an integer between 1 and 100;

[0117] w is an integer between 1 and 3;

[0118] t, x, y, and z are independent integers from 0 to 50, provided that the sum of t + x + y + z is between 1 and 150.

[0119] In another preferred embodiment, R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 20 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C5-C 10 Cycloalkyl, substituted or unsubstituted C5-C 10 Cycloalkenyl, substituted or unsubstituted aryl and substituted or unsubstituted aralkyl; in each case substituted with at least one hydroxyl functional group;

[0120] R d 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 20 Cycloalkyl, substituted or unsubstituted C5-C 20Cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0121] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0122] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0123] n is an integer between 1 and 300;

[0124] w is an integer between 0 and 30;

[0125] t, x, y, and z are independent integers from 0 to 300, provided that the sum of t + x + y + z is between 1 and 900.

[0126] In another preferred embodiment, at least one isocyanate reactive component (B) is present as a mixture of primary, secondary, and tertiary amines, wherein the majority portion comprises a secondary amine. It should also be understood that identical molecule may have one or more primary amine functional groups and at least one secondary amine functional group. Similarly, identical molecule may have one or more tertiary amine functional groups and at least one secondary amine functional group. Likewise, identical molecule may have one or more primary amine functional groups and / or one tertiary amine functional group and at least one secondary amine functional group.

[0127] In another preferred embodiment, the primary amine is present in the at least one isocyanate reactive component (B) in an amount of 0-10% by weight based on the total weight of the isocyanate reactive component (B); more preferably, the primary amine is present in the at least one isocyanate reactive component (B) in an amount of 0-8% by weight based on the total weight of the isocyanate reactive component (B); even more preferably, the primary amine is present in the at least one isocyanate reactive component (B) in an amount of 0.5-5% by weight based on the total weight of the isocyanate reactive component (B); most preferably, the primary amine is present in the at least one isocyanate reactive component (B) in an amount of 1-4% by weight based on the total weight of the isocyanate reactive component (B); in particular, the primary amine is present in the at least one isocyanate reactive component (B) in an amount of 1-3% by weight based on the total weight of the isocyanate reactive component (B).

[0128] 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. 30 In 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 The alkyl group can be straight-chain or branched in each case, and the aforementioned phenyl group can preferably be 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 can be independently selected from F, Cl, Br, I, -NO2, -CN, -OH, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0129] In another preferred embodiment, unsubstituted linear C1-C30 The 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 from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0130] In another preferred embodiment, unsubstituted branched C1-C 30The 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)-OH, -(CH2)-(CH2)-NH2, -(CH2)-(CH2)-CN, -(CF2)-(CF3), -(CH2)-(CH2)-(CF3), and -(CH2)-(CH2)-(CH2)-OH.

[0131] 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, -OH, -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)-C1-5 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 can be straight-chain or branched in each case, and the aforementioned phenyl group can preferably be substituted with 1, 2, 3, 4 or 5 substituents independently selected from F, Cl, Br, I, -CN, -CF3, -OH, -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 can be independently selected from F, Cl, Br, I, -NO2, -CN, -OH, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0132] In another preferred embodiment, the linear or branched C1-C is replaced 30 Alkyl refers to a C1-C alkyl group having a functional group substituted by a group selected from hydroxyl, alkoxy, C(=O)R, CN, and SR. 30The branched or straight-chain saturated hydrocarbon group of the carbon atom is preferably selected from 1-hydroxymethyl, 1-methoxymethyl, 1-hydroxyethyl, 1-hydroxypropyl, 1-hydroxybutyl, 1-hydroxypentyl, 1-hydroxyhexyl, 1-hydroxyheptyl, 1-hydroxyoctyl, 1-hydroxynonyl, decyl, 1-hydroxyundecyl, 1-hydroxydodecyl, 1-hydroxytridecyl, 1-hydroxytetradecyl, 1-hydroxypentadecanyl, 1-hydroxyhexadecyl, 1-hydroxyheptadecyl, 1-hydroxyheptadecyl, 1-hydroxyoctadecyl, 1-hydroxynonadecanyl, 1-hydroxyeicosyl, 1-hydroxytidecyl, 1-hydroxytetradecyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methyl 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-Methoxydodecyl, 1-Methoxytetradecyl, 1-Methoxytetradecyl, 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-Methoxytimonodecyl, 2-Methoxytimonodecyl, 2-Methoxytetradecyl, 1-Acetoxymethyl, 1-Acetoxyethyl, 1-Acetoxypropyl, 1-Acetoxybutyl, 1-Acetoxypentyl, 1-Acetoxyhexyl, 1-Acetoxyheptyl, 1-Acetoxyoctyl, 1-Acetoxynonyl, Decyl, 1-Acetoxyundecyl, 1-Acetoxydodecyl Alkyl, 1-acetoxytridecyl, 1-acetoxytetradecyl, 1-acetoxypentadecanyl, 1-acetoxyhexadecyl, 1-acetoxyheptadecyl, 1-acetoxyoctadecyl, 1-acetoxynonadecanyl, 1-acetoxyeicosyl, 1-acetoxydodecyl, 1-acetoxydodecyl, 1-acetoxytetradecyl, 1-acetoxytetradecyl, 1-cyanomethyl, 1-cyanoethyl, 1-cyanopropyl, 1-cyanobutyl, 1-cyanopentyl, 1-cyanohexyl, 1-cyanoheptyl, 1-cyanooctyl, 1-cyanononyl, decyl, 1-cyanoundecyl, 1-cyanododecyl, 1-cyanotridecyl, 1-cyanotetradecyl, 1-cyanopentadecanyl1-Cyanohexadecanyl, 1-Cyanohepadecanyl, 1-Cyanoctadecyl, 1-Cyanonedecyl, 1-Cyanoeicosyl, 1-Cyanonedecyl, 1-Cyanonedecyl, 1-Cyanonetridecyl, 1-Cyanonetetradecyl, 2-Cyanopropyl, 2-Cyanobutyl, 2-Cyanopentyl, 2-Cyanohexyl, 2-Cyanohepyl, 2-Cyanoctadecyl, 2-Cyanonedecyl, 2-Cyanonedecyl, 2-Cyanonedecyl, 2-Cyanonetetradecyl, 2-Cyanonedecyl, 2-Cyanonedecyl, 2-Cyanonedecyl, 2-Cyanoneeicos ... Dodecyl, 2-cyanobocyclodecyl, 2-cyanobocyclotane, 2-cyanobocyclotane, 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-thioyleicosyl, 1-thioyleicosyl, 1-thioyltetradecyl, 1-thioyltridecyl, and 1-thioyltetradecyl.

[0133] In another preferred embodiment, the term alkenyl means an unsubstituted straight-chain C2-C 30Alkenyl 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.

[0134] In another preferred embodiment, unsubstituted branched C2-C 30 The 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.

[0135] In another 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 hydroxyl, 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 group.

[0136] In another preferred embodiment, the term "alkenyl" refers to a C2-C group having a functional group substituted by a group selected from hydroxyl, alkoxy, C(=O)R, CN, and SR. 30Branched or straight-chain unsaturated hydrocarbon groups of carbon atoms; preferably selected from 2-hydroxypropenyl, 3-hydroxybutenyl, 3-hydroxypentenyl, 5-hydroxyhexenyl, 7-hydroxyheptenyl, 3-hydroxyoctenyl, 5-hydroxynonenyl, decyl, 11-hydroxyundecenyl, 9-hydroxydodecenyl, 6-hydroxytetadedecenyl, 4-hydroxytetradecenyl, 6-hydroxypentadedecenyl, 3-hydroxyhexadecenyl, 2-hydroxyheptadecenyl, 7-hydroxyoctadecenyl, 6-hydroxynonadedecenyl, 4-hydroxyeicosenoenyl, 2-hydroxythodecenyl, 3-hydroxythodecenyl, 2-hydroxythodecenyl, 23-hydroxythodecenyl, 1-methoxyvinyl, 2-methoxypropenyl, 4-methoxy Butenyl, 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-methoxyeicosaeca-20-enyl, 1-methoxytetradec-2-enyl, 1-methoxytetradec-4-enyl, 1-methoxytetradec-22-enyl, 1-methoxytetradec-24-enyl -23-alkenyl, 2-methoxypropyl-1-alkenyl, 2-methoxybut-1-alkenyl, 2-methoxypent-4-alkenyl, 2-methoxyhex-2-alkenyl, 2-methoxyhept-3-alkenyl, 2-methoxyoct-7-alkenyl, 2-methoxynon-5-alkenyl, 2-methoxyundec-10-alkenyl, 2-methoxydodec-4-alkenyl, 2-methoxytetracene-12-alkenyl, 2-methoxytetradec-10-alkenyl, 2-methoxypentadecan-14-alkenyl, 2-methoxyhexadec-1-alkenyl, 2-methoxyheptadec-1-alkenyl, 2-methoxyoctadec-12-alkenyl, 2-methoxynondecan-10-alkenyl, 2-methoxyeicosuccine-18-alkenyl, 2-methoxytetradecane-18-alkenyl C2-alkenyl, 2-methoxydoco-3-alkenyl, 20-methoxydoco-2-alkenyl, 21-methoxydoco-4-alkenyl, 1-acetoxyvinyl, 1-acetoxyprop-1-alkenyl, 1-acetoxybut-2-alkenyl, 1-acetoxypent-4-alkenyl, 1-acetoxyhex-2-alkenyl, 1-acetoxyhept-1-alkenyl, 1-acetoxyoct-7-alkenyl, 1-acetoxynon-2-alkenyl, 5-acetoxydec-3-alkenyl, 1-acetoxyundec-10-alkenyl, 1-acetoxydodec-2-alkenyl, 1-acetoxytetride-12-alkenyl, 10-acetoxytetradec-2-alkenyl, 15-acetoxypentadecan-2-alkenyl10-Acetoxyhexadec-2-enyl, 11-Acetoxyheptadec-1-enyl, 13-Acetoxyhexadecadec-2-enyl, 1-Acetoxyhexadecadec-14-enyl, 20-Acetoxyheicodec-19-enyl, 1-Acetoxyhexadec-2-enyl, 1-Acetoxyhexadec-10-enyl, 1-Acetoxyhexadec-22-enyl, 1-Acetoxyhexadec-23-enyl, 1-Cyanoethyl-1-enyl, 1-Cyanoprop-2-enyl, 1-Cyanobut-2-enyl, 1-Cyanopent-3-enyl, 1-Cyanohex-5-enyl, 1-Cyanohept-6-enyl, 1-Cyanooct-2-enyl, 1-Cyanonon-3-enyl, 11-Cyanoundec-2 -Alkenyl, 10-cyanododec-2-enyl, 10-cyanotridec-12-enyl, 1-cyanotetradec-3-enyl, 1-cyanopentadecadec-14-enyl, 1-cyanohexadec-15-enyl, 1-cyanoheptadec-2-enyl, 1-cyanooctadec-3-enyl, 1-cyanononadecadec-18-enyl, 1-cyanoeicosico-10-enyl, 1-cyanoticosico-20-enyl, 15-cyanoticosico-3-enyl, 1-cyanoticosico-20-enyl, 1-cyanoticosico-24-enyl, 2-cyanoprop-2-enyl, 2-cyanobut-1-enyl, 2-cyanopent-1-enyl, 2-cyanohex-3-enyl, 2-cyanohept-6-enyl, 2-cyanooctyl -1-Alkenyl, 2-Cyanonon-8-Alkenyl, 2-Cyanoundec-10-Alkenyl, 2-Cyanododec-1-Alkenyl, 2-Cyanotridec-12-Alkenyl, 2-Cyanotetradec-10-Alkenyl, 2-Cyanopentadecan-3-Alkenyl, 2-Cyanohexadec-2-Alkenyl, 2-Cyanoheptadec-1-Alkenyl, 2-Cyanooctadec-12-Alkenyl, 2-Cyanononadecan-15-Alkenyl, 2-Cyanoeicosode-1-Alkenyl, 2-Cyanotetradec-5-Alkenyl, 2-Cyanotetradec-20-Alkenyl, 2-Cyanotetradec-22-Alkenyl, 2-Cyanotetradec-20-Alkenyl, 1-Thioyleth-1-Alkenyl, 1-Thioylprop-2-Alkenyl, 1-Thioylbut-2-Alkenyl, 1- Thionylpentan-4-enyl, 1-thioylhexan-2-enyl, 1-thioylheptan-5-enyl, 1-thioyloctan-3-enyl, 1-thioylnonan-5-enyl, 1-thioylundec-10-enyl, 1-thioyldodec-11-enyl, 1-thioyltridec-2-enyl, 1-thioyltetradec-4-enyl, 1-thioylpentadedec-5-enyl, 1-thioylhexadec-3-enyl, 1-thioylheptadec-2-enyl, 1-thioyloctadec-3-enyl, 1-thioylnondedec-15-enyl, 1-thioyleicosaedec-18-enyl, 1-thioylteicosaedec-20-enyl, 1-thioylteicosaedec-21-enyl, 1-thioylteicosaedec-20-enyl, and 1-thioylteicosaedec-22-enyl.

[0137] In a preferred embodiment, the term "heteroalkyl" refers to an alkyl group in which one or more carbon atoms are replaced in each case by heteroatoms independently selected from oxygen, sulfur, and nitrogen (NH). 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 quinones, particularly preferably 2-6 quinones. Examples of heteroalkyl groups include, but are not limited to, alkoxy, polyethylene glycol-, and alkyl-substituted amino groups.

[0138] In another preferred embodiment, the term "heteroalkenyl" refers to an alkenyl group in which at least one atom is a heteroatom selected from oxygen, nitrogen, or sulfur. 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. Examples of heterochain alkenes include, but are not limited to, those selected from -CH2-O-CH=CH2, -CH=CH-O-CH=CH-CH3, -CH2-CH2-O-CH=CH2, -CH2-S-CH=CH2, -CH=CH-S-CH=CH-CH3, -CH2-CH2-S-CH=CH2, -CH2-NH-CH=CH2, -CH=CH-NH-CH=CH-CH3 and -CH2-CH2-NH-CH=CH2; more preferably, heterochain alkenes are selected from -CH2-O-CH=CH-(CH2)-OH, -CH2-S-CH=CH-(CH2)-NH2 and -CH2-NH-CH=CH-CN.

[0139] In a preferred embodiment, the term "cycloalkyl" refers to a 5-30 member saturated alicyclic group, whether monocyclic or bicyclic. Unsubstituted or branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclic [2.2.1]heptyl, (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, (3,4)-dihydro-2H-benzo[1.4] Azine group and octahydro-pyrrolo[3,4-c]pyrrole group and bicyclic[3.1.1]heptyl group.

[0140] 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 10Representative examples of monocyclic and bicyclic cycloalkyl groups include, but are not limited to, methylcyclohexyl and dimethylcyclohexyl.

[0141] In another preferred embodiment, the term "cycloalkenyl" refers to a 5-30 membered monocyclic and bicyclic unsaturated alicyclic group containing 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.

[0142] In another preferred embodiment, the term "heterocyclic alkyl" refers to a non-aromatic monocyclic or polycyclic ring comprising 5-30 carbon atoms and at least one heteroatom selected from O, S, and N. Preferred examples include, but are not limited to, aziridinyl, pyrrolyl, pyrrolidine, piperidinyl, piperidinyl, piperazinyl, piperazinyl, morpholinyl, morpholino, thiomorpholino, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl, pyranyl, imidazoalkyl, tetrahydrofuranyl, tetrahydrothiopheneyl, pyrrolyl, piperidinyl, morpholino, piperazinyl, thiomorpholino, tetrahydropyranyl, oxacyclobutyl, azepanyl, azocanyl, diazapyridine, azepanyl, azecanyl, and diazapyridine. diazepanyl, dithiopentane, (1,3)-dioxolane-2-yl, iso Alzolyl, isothiazolyl, pyrazolyl azolealkyl, (1,2,4)- Diazolidinyl, (1,2,4)-thiadiazolidinyl, (1,2,4)-triazolidine-3-yl, (1,3,4)-thiadiazolidine-2-yl, (1,3,4)-triazolidine-1-yl, (1,3,4)-triazolidine-2-yl, tetrahydropyridazinyl, tetrahydropyrazinyl, (1,3,5)-tetrahydrotriazinyl, (1,2,4)-tetrahydrotriazin-1-yl, (1,3)-dithiadin-2-yl and (1,3)-thiazolyl.

[0143] In another preferred embodiment, the term "heterocyclic alkenyl" refers to a non-aromatic monocyclic or polycyclic ring comprising 5-30 carbon atoms, having at least one heteroatom selected from O, S, and N, and having 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 Azol-2-yl, 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.

[0144] In another preferred embodiment, the terms "heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl" also refer to monosubstituted or polysubstituted compounds having 1, 2, 3, 4 or 5, more preferably 1, 2 or 3 substituents, wherein the substituents may be 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 1-5 Alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-C 1-5 Alkyl, -S(=O)-C 1-5 Alkyl, -NH-C 1-5 Alkyl, N(C) 1-5 Alkyl)(C 1-5Alkyl), -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 The alkyl group can be straight-chain or branched in each case, and the cyclic substituents, or the cyclic groups of these substituents themselves, can be 1, 2, 3, 4, or 5 in each case, 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.

[0145] 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.

[0146] 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.

[0147] In another 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 carbon atoms, particularly preferably having 5, 6, 9, 10, 13, or 14 carbon atoms, and very particularly preferably having 5 or 6 carbon atoms, wherein one or more carbon atoms are replaced by heteroatoms, each independently selected from oxygen, sulfur, and nitrogen (NH). The heteroaryl group may preferably comprise 1, 2, 3, 4, or 5, particularly preferably 1, 2, or 3 heteroatoms, each independently selected from oxygen, sulfur, and nitrogen (NH), as ring members. The heteroaryl group may be 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.

[0148] 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.

[0149] 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 1-5Alkyl, -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 Substituents of alkyl groups, pyrazolyl, phenyl, furanyl, thiazolyl, thiadiazolyl, thiophene, benzyl, and phenethyl, wherein the above C 1-5 The alkyl group can be straight-chain or branched in each case, and the cyclic substituents or the cyclic groups of these substituents can be 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 1-5Substituents 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 -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 may be 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.

[0150] 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.

[0151] 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 Azol-2-yl, 4-chloro Azol-2-yl, 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.

[0152] For the purposes of this invention, the term "alkylene" encompasses acyclic saturated hydrocarbon groups, which can be acyclic saturated hydrocarbon chains incorporating different structural moieties, such as those in C1-C2. 30 In the case of alkylene 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 alkylene groups, 1-5 (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 -

[0153] In another preferred embodiment, the compound of formula (B1) is selected from the compounds of formulas (B1a) and (B1b):

[0154]

[0155] Where n is 1-1000, more preferably 1-500, even more preferably 1-100, most preferably 1-70, and especially an integer from 1 to 50;

[0156]

[0157] Where n is 1-1000, more preferably 1-500, even more preferably 1-100, most preferably 1-70, and especially an integer from 1 to 50.

[0158] In another preferred embodiment, the compound of formula (B2) is selected from compounds of formulas (B2a), (B2b), (B2c), (B2d), (B2e), and (B2f):

[0159]

[0160] Where x+y+z is a number between 1 and 3000, preferably between 1 and 1000, more preferably between 1 and 500, and most preferably between 1 and 100, especially integers between 1 and 50.

[0161]

[0162] Where x+y+z is 1-3000, preferably 1-1000, more preferably 1-500, most preferably 1-100, and especially an integer from 1 to 50;

[0163]

[0164] Where t+x+y+z is 1-3000, preferably 1-1000, more preferably 1-500, most preferably 1-100, and particularly an integer of 4-50; and the compound of formula (B2d) is:

[0165]

[0166] Where t+x+y+z is 1-3000, preferably 1-1000, more preferably 1-500, most preferably 1-100, and especially an integer of 4-50;

[0167]

[0168] Where x+y+z is a number between 1 and 3000, preferably between 1 and 1000, more preferably between 1 and 500, and most preferably between 1 and 100, especially integers between 1 and 50.

[0169]

[0170] Where x+y+z is 1-3000, preferably 1-1000, more preferably 1-500, most preferably 1-100, and especially an integer from 1 to 50.

[0171] In another preferred embodiment, the compound of formula (B3) is selected from the compounds of formulas (B3a) and (B3b):

[0172]

[0173] In another preferred embodiment, the polyurea copolymer is obtained by the following reaction: a. at least one polyisocyanate (A) selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethylbenzene diisocyanate, and 3,3'-dimethylbenzene diisocyanate. The following are considered as follows: 1. Methylene-4,4'-biphenyl diisocyanate, methylene-bis(4-phenylisocyanate), 2,2'-methylene-bis(cyclohexylisocyanate), 3,3'-methylene-bis(cyclohexylisocyanate), 4,4'-methylene-bis(cyclohexylisocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanate-phenylene, and diisocyanates and triisocyanates in polymeric form; and b. at least one isocyanate reactive component (B) selected from formulas (B1a), (B1b), (B2a), and (B2b).

[0174] Compounds of (B2c) and (B2d), wherein (B1a), (B1b), (B2a), (B2b), (B2c), and (B2d)

[0175] (B2e), (B2f), (B3a) and (B3b) are as defined above;

[0176] More preferably, the polyurea copolymer is obtained by the following reaction:

[0177] a. At least one polyisocyanate (A), selected from isophorone diisocyanate, hexamethylene...

[0178] -1,6-diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, methylene-bis(4-phenylisocyanate), 2,2'-methylene-bis(cyclohexylisocyanate), 3,3'-methylene-bis(cyclohexylisocyanate), 4,4'-methylene-bis(cyclohexylisocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanate-phenylene, and diisocyanates and triisocyanates in polymeric forms; and

[0179] b. At least one isocyanate reactive component (B), selected from formulas (B1a), (B1b), (B2a), and (B2b).

[0180] Compounds of (B2c), (B2d), (B2e), (B2f), (B3a), and (B3b), of which (B1a), (B1b),

[0181] (B2a), (B2b), (B2c), (B2d), (B2e), (B2f), (B3a), and (B3b) are as defined above;

[0182] Most preferably, the polyurea copolymer is obtained through the following reaction:

[0183] a. At least one polyisocyanate (A), selected from 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'-methylene-bis(cyclohexylisocyanate), 3,3'-methylene-bis(cyclohexylisocyanate), 4,4'-methylene-bis(cyclohexylisocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanatobenzene, and diisocyanates and triisocyanates in polymeric form; and

[0184] b. At least one isocyanate reactive component (B), selected from formulas (B1a), (B1b), (B2a), and (B2b).

[0185] Compounds of (B2c), (B2d), (B2e), (B2f), (B3a), and (B3b), of which B1a), (B1b),

[0186] (B2a), (B2b), (B2c), (B2d), (B2e), (B2f), (B3a), and (B3b) are as defined above. In another preferred embodiment, the polyurea copolymer is obtained by the following reaction: a. a polymeric diphenylmethane diisocyanate (A) with an NCO functionality of at least ≥2.0; and b. at least one isocyanate reactive component (B) selected from compounds of formula (B1), (B2), (B3), and (B4):

[0187]

[0188] Where R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C30 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; in each case substituted with at least one hydroxyl functional group;

[0189] R d 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, substituted or unsubstituted C1-C 10Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0190] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0191] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0192] n is an integer between 1 and 1000;

[0193] w is an integer between 0 and 30;

[0194] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t+x+y+z is 1-3000. In another preferred embodiment, the polyurea copolymer is obtained by the following reaction: a. a polymeric diphenylmethane diisocyanate (A) with an NCO functionality of at least ≥2.0; and b. at least one isocyanate reactive component (B) selected from compounds of formulas (B1a), (B1b), (B2a), (B2b), (B2c), and (B2d), wherein (B1a), (B1b), (B2a), (B2b), (B2c), and (B2d) are as defined above.

[0195] 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; in particular, 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.

[0196] In another preferred embodiment, the weight-average molecular weight (Mw) of the polyurea copolymer is 5000-50,000 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.

[0197] In another preferred embodiment, the polyurea copolymer has a glass transition temperature of ≥-40°C to ≤250°C, determined according to ASTM D 3418 at a heating rate of 5 K / min. Preferably, the glass transition temperature of the polyurea copolymer is ≥-20°C to ≤250°C, determined according to ASTM D 3418 at 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 at a heating rate of 5 K / min; even more preferably, the glass transition temperature of the polyurea copolymer is ≥20°C to ≤180°C, determined according to ASTM D 3418 at a heating rate of 5 K / min; most preferably, the glass transition temperature of the polyurea copolymer is ≥40°C to ≤160°C, determined according to ASTM D 3418 at 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 at a heating rate of 5 K / min.

[0198] In another preferred embodiment, the method for preparing the polyurea copolymer includes at least the following steps: i) providing at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0199] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0200] The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group;

[0201] More preferably, the method for preparing polyurea copolymers includes at least the following steps:

[0202] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0203] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0204] The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group;

[0205] Even more preferably, the method for preparing polyurea copolymers includes at least the following steps:

[0206] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0207] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0208] The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group;

[0209] Most preferably, the method for preparing the polyurea copolymer includes at least the following steps:

[0210] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0211] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0212] The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group.

[0213] In another preferred embodiment, the method for preparing the polyurea copolymer includes at least the following steps: i) providing at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0214] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0215] The at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4):

[0216]

[0217]

[0218] in:

[0219] R a R b R c R g R m and R e Independently selected from linear 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 30aryl, 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; in each case substituted with at least one hydroxyl functional group;

[0220] R d 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, substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0221] R f R h R j and R k They are independently selected from hydrogen and -(CH2).w -(OCH(R7)-CH(R8)) t -NHR e ;

[0222] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0223] n is an integer between 1 and 1000;

[0224] w is an integer between 0 and 30;

[0225] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t + x + y + z is between 1 and 3000.

[0226] More preferably, the method for preparing polyurea copolymers includes at least the following steps:

[0227] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0228] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0229] The at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4):

[0230]

[0231]

[0232] R a R b R c R g R m and R e Independently selected from linear 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 10Alkylene 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; in each case substituted with at least one hydroxyl functional group;

[0233] R d 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 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, substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0234] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0235] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, methyl, ethyl, and propyl.

[0236] n is an integer from 1 to 500;

[0237] w is an integer between 0 and 10;

[0238] t, x, y, and z are independent integers from 0 to 500, provided that the sum of t + x + y + z is between 1 and 1500.

[0239] Even more preferably, the method for preparing polyurea copolymers includes at least the following steps:

[0240] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0241] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0242] The at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4):

[0243]

[0244] Even more preferably, R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 20 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 20 Alkenyl, substituted or unsubstituted straight-chain or branched 2-20 heteroalkyl groups, substituted or unsubstituted C5-C 20 cycloalkyl, substituted or unsubstituted C6-C 20 aryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-10 membered heterocyclic alkyl, substituted or unsubstituted C1-C 10 alkylene 5-20 membered heterocyclic alkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 20 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5-20-membered heteroaryl; in each case substituted with at least one hydroxyl functional group;

[0245] R d Selected from hydrogen, straight-chain or branched substituted or unsubstituted C1-C 30Alkyl, 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 C1-C 10 Alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 aryl, substituted or unsubstituted C1-C 10 Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0246] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, methyl, ethyl, and propyl.

[0247] n is an integer between 1 and 300;

[0248] w is an integer between 0 and 5;

[0249] t, x, y, and z are independent integers from 0 to 300, provided that the sum of t + x + y + z is between 1 and 900.

[0250] Most preferably, the preparation of the polyurea copolymer includes at least the following steps:

[0251] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0252] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0253] The at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4):

[0254]

[0255]

[0256] Most preferably, R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 15 Alkyl, straight-chain or branched substituted or unsubstituted C2-C15 Alkenyl, substituted or unsubstituted C5-C 15 cycloalkyl, substituted or unsubstituted C6-C 10 aryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 15 Cycloalkyl and substituted or unsubstituted C1-C 10 Alkylene C6-C 15 aryl group; in each case, it is substituted with at least one hydroxyl functional group;

[0257] R d 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 and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0258] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0259] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, methyl, ethyl, and propyl.

[0260] n is an integer between 1 and 100;

[0261] w is an integer between 1 and 3;

[0262] t, x, y, and z are independent integers from 0 to 100, provided that the sum of t + x + y + z is between 1 and 300.

[0263] Specifically, the method for preparing polyurea copolymers includes at least the following steps:

[0264] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0265] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0266] The at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), and formula (B3):

[0267]

[0268] In particular, R a R b R c R g and R e 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 group; in each case, it is substituted with at least one hydroxyl functional group;

[0269] R d 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 and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0270] R g and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0271] R j and R f -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0272] R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen and methyl;

[0273] n is an integer between 1 and 100;

[0274] w is an integer between 1 and 3;

[0275] t, x, y, and z are independent integers from 0 to 50, provided that the sum of t + x + y + z is between 1 and 150.

[0276] In another preferred embodiment, the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:10 to ≤10:1.0; more preferably, the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:6 to ≤6:1.0; even more preferably, the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:5 to ≤5:1.0; most preferably, the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:3 to ≤3:1.0; particularly, the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:2.0 to ≤2.0:1.0.

[0277] In another preferred embodiment, the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:0.5 to ≤0.5:1.0.

[0278] 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 ≥-30°C to ≤200°C; even more preferably, step iii) is carried out at a temperature of ≥-4°C to ≤160°C; most preferably, step iii) is carried out at a temperature of ≥0°C to ≤160°C; particularly, step iii) is carried out at a temperature of ≥20°C to ≤140°C.

[0279] In another preferred embodiment, the method for preparing the polyurea copolymer is carried out in the presence of at least one solvent.

[0280] 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.

[0281] In another preferred embodiment, the present invention relates to an article comprising the polyurea copolymer described herein.

[0282] In another preferred embodiment, the present invention relates to a method for reshaping a polyurea copolymer, comprising at least the following steps:

[0283] a) Applying pressure and heat to the polyurea copolymer described herein to obtain a heated polyurea copolymer; and

[0284] b) Reshape the polyurea copolymer from step a).

[0285] In another preferred embodiment, the remolding of the polyurea copolymer is ≥5×10 3 Pa to ≤10 7 The test was conducted under a pressure of Pa.

[0286] In another preferred embodiment, the remolding of the polyurea copolymer is carried out at a temperature of ≥60°C to ≤300°C.

[0287] This invention is associated with at least one of the following advantages:

[0288] (i) A novel polyurea copolymer with dynamic bonds was developed.

[0289] (ii) A novel polyurea copolymer with recyclability was developed.

[0290] (iii) A novel polyurea copolymer was developed having a three-dimensional network structure based solely on the reaction of polyisocyanates and polyamines without the use of additional crosslinking agents.

[0291] Implementation plan:

[0292] 1. A polyurea copolymer obtained by reacting the following substances:

[0293] a. at least one polyisocyanate (A); and

[0294] b. At least one isocyanate reactive component (B);

[0295] The at least one polyisocyanate (A) has an NCO functionality of at least 2.0; and

[0296] The at least one isocyanate reactive component (B) is selected from compounds of formula (B1), formula (B2), formula (B3), and formula (B4).

[0297]

[0298]

[0299] in:

[0300] R a R b R c R g R m and R e Independently selected from linear or branched substituted or unsubstituted C1-C 30 Alkyl, straight-chain or branched substituted or unsubstituted C2-C 30Alkenyl 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; in each case substituted with at least one hydroxyl functional group;

[0301] R d 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, substituted or unsubstituted C1-C 10Alkylene, 5-30-membered heteroaryl groups, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0302] R f R h R j and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0303] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0304] n is an integer between 1 and 1000;

[0305] w is an integer between 0 and 30;

[0306] t, x, y, and z are independent integers from 0 to 1000, provided that the sum of t + x + y + z is an integer from 1 to 3000.

[0307] 2. The polyurea copolymer according to embodiment 1, wherein the at least one polyisocyanate (A) has an average NCO functionality of ≥2.0 to ≤6.0.

[0308] 3. The polyurea copolymer according to embodiment 1, wherein the at least one polyisocyanate (A) 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, m-phenylene 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-phenylene) (e.g., 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) 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-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-based adamantane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-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-, Diazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, OCH(CH2)3N(CH3)(CH2)3NCO, triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-triyltriisocyanate, ethyl l-lysine 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) Bis(hexamethylene)isocyanate, 1,3,5-triisocyanate-based benzene, bis(isocyanate-based hexyl)biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triylbis(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates.

[0309] 4. The polyurea copolymer according to any one of embodiments 1-3, wherein the at least one polyisocyanate (A) contains urethane groups, isocyanurate groups, biuret groups, urea diketone groups, ureocarbamate groups and / or imino groups. It exists in the form of dimers, trimers and oligomers of diazine dione.

[0310] 5. The polyurea copolymer according to any one of embodiments 1-4, wherein the at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate 4,4'-Bisphenylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, methylene-bis(4-phenylisocyanate), 2,2'-methylene-bis(cyclohexylisocyanate), 3,3'-methylene-bis(cyclohexylisocyanate), 4,4'-methylene-bis(cyclohexylisocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanate-phenylene, and diisocyanates and triisocyanates in polymeric forms.

[0311] 6. The polyurea copolymer according to any one of embodiments 1, wherein R a R b R c R g R m and R e Independently selected from linear 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 20 Cycloalkyl, substituted or unsubstituted C5-C 20 Cycloalkenyl, substituted or unsubstituted aryl and substituted or unsubstituted aralkyl; in each case substituted with at least one hydroxyl functional group;

[0312] R d 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 20 Cycloalkyl, substituted or unsubstituted C5-C 20 Cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, and -(CH2) w -(OCH(R7)-CH(R8)) t -NHR e ;

[0313] R f R h Rj and R k They are independently selected from hydrogen and -(CH2). w -(OCH(R7)-CH(R8)) t -NHR e ;

[0314] R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl;

[0315] n is an integer between 1 and 300;

[0316] w is an integer between 0 and 30;

[0317] t, x, y, and z are independent integers from 0 to 300, provided that the sum of t+x+y+z is from 1 to 900.

[0318] 7. A polyurea copolymer according to any one of embodiments 1-6, wherein the compound of formula (B1) is selected from the compounds of formulas (B1a) and (B1b):

[0319]

[0320] Where n is an integer from 1 to 1000;

[0321]

[0322] Where n is an integer from 1 to 1000.

[0323] 8. A polyurea copolymer according to any one of embodiments 1-6, wherein the compound of formula (B2) is selected from compounds of formulas (B2a), (B2b), (B2c), (B2d), (B2e) and (B2f):

[0324]

[0325] Where x + y + z are integers from 1 to 3000.

[0326]

[0327] Where x+y+z are integers from 1 to 3000;

[0328]

[0329] Where t+x+y+z are integers from 1 to 3000;

[0330]

[0331] Where t+x+y+z are integers from 1 to 3000;

[0332]

[0333] Where x+y+z are integers from 1 to 3000;

[0334]

[0335] Where x+y+z are integers from 1 to 3000.

[0336] 9. The polyurea copolymer according to any one of embodiments 1-6, wherein the compound of formula (B3) is selected from the compounds of formulas (B3a) and (B3b):

[0337]

[0338]

[0339] 10. The polyurea copolymer according to any one of embodiments 1-9, wherein: a. at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, di ... Methyl-4,4'-biphenylene diisocyanate, methylene-bis(4-phenylisocyanate), 2,2'-methylene-bis(cyclohexylisocyanate), 3,3'-methylene-bis(cyclohexylisocyanate), 4,4'-methylene-bis(cyclohexylisocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanate-phenylene, and diisocyanates and triisocyanates in polymeric form; and b. at least one isocyanate reactive component (B) is selected from formulas (B1a), (B1b), (B2a), and (B2b).

[0340] Compounds of formulas (B2c), (B2d), (B2e), (B2f), (B3a), and (B3b), wherein (B1a), (B1b),

[0341] The compounds (B2a), (B2b), (B2c), (B2d), (B2e), (B2f), (B3a) and (B3b) are as defined in embodiments 7-9.

[0342] 11. The polyurea copolymer according to any one of embodiments 1-10, wherein the polyurea copolymer has a weight-average molecular weight Mw of 500-500,000 g / mo, determined according to DIN 55672, or, in the case of a high molecular weight in which the polymer material is no longer soluble in standard organic solvents, the molecular weight is determined by MALDI-TOF mass spectrometry.

[0343] 12. The polyurea copolymer according to embodiment 12, wherein the polyurea copolymer has a weight-average molecular weight Mw of 5,000-50,000 g / mol, determined according to the method described in the specification, or, in the case of a high molecular weight in which the polymer material is no longer soluble in a standard organic solvent, the molecular weight is determined by MALDI-TOF mass spectrometry.

[0344] 13. The polyurea copolymer according to any one of embodiments 1-12, wherein the polyurea copolymer has a glass transition temperature of ≥-40°C to ≤250°C, determined according to ASTM D 3418 at a heating rate of 5 K / min.

[0345] 14. A method for preparing a polyurea copolymer according to any one of embodiments 1-13, comprising at least the following steps:

[0346] i) Provide at least one polyisocyanate (A) with an average NCO functionality ≥ 2.0;

[0347] ii) providing at least one isocyanate reactive component (B); and iii) contacting (A) and (B);

[0348] The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group.

[0349] 15. The method according to embodiment 14, wherein the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:10 to ≤10:1.0.

[0350] 16. The method according to embodiment 15, wherein the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:2.0 to ≤2.0:1.0.

[0351] 17. The method according to embodiment 16, wherein the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:0.5 to ≤0.5:1.0.

[0352] 18. The method according to any one of embodiments 14-17, wherein step iii) is carried out at a temperature of ≥-50°C to ≤250°C.

[0353] 19. The method according to any one of embodiments 14-18, wherein the reaction is carried out in the presence of at least one solvent.

[0354] 20. The method according to embodiment 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.

[0355] 21. An article comprising a polyurea copolymer according to any one of embodiments 1-13 or a polyurea copolymer obtained according to any one of 14-20.

[0356] 22. A method for remolding a polyurea copolymer according to any one of embodiments 1-13, or a polyurea copolymer obtained according to any one of embodiments 14-20, or an article according to embodiment 21, comprising at least the following steps:

[0357] a) Applying pressure and heating to a polyurea copolymer to obtain a heated polyurea copolymer; and

[0358] b) Reshape the polyurea copolymer from step a).

[0359] 23. The method according to implementation scheme 22, wherein the pressure is ≥5×10 3 Pa to ≤10 7 Pa.

[0360] 24. The method according to implementation scheme 23, wherein the temperature is ≥60°C to ≤300°C.

[0361] Although the invention has been described with respect to specific embodiments thereof, 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

[0362] Material

[0363] PMDI (Lupranate M20 FB) is sourced from BASF. TDI T80 (80% 2,4-TDI, 20% 2,6-TDI) is sourced from BASF SE. TDI T100 (100% 2,4-TDI) is sourced from Sigma-Aldrich. D400 ( EC302), T403 ( EC310), D2000 Both EC303 and T5000 were obtained from BASF SE. These polyetheramines were alkoxylated according to the procedure given below. THF was dried using molecular sieve (4A).

[0364]

[0365]

[0366] method

[0367] 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.

[0368] The residual NCO content was determined by IR spectroscopy.

[0369] TGA spectra were obtained in a gold crucible under N2 atmosphere according to ISO 11358.

[0370] Thermoforming method

[0371] Test method:

[0372] The polymer powder / particles obtained according to the examples are transferred to a hot press. When a pressure of 20 kN and a temperature of 160-180°C are applied for at least 5 minutes, the polymer powder is reformed into a solid biscuit-like plate.

[0373] The polymer powder obtained according to the present invention is reshaped into biscuits / plates; however, the biscuits / plates formed from the polymer obtained according to the comparative examples are not solid and are easily scattered.

[0374] synthesis

[0375] Synthesis of secondary polyetheramines:

[0376] a) Polyetheramine D400 (=Baxxodur EC 302) + 0.5BuO / NH:

[0377] Polyetheramine D400 (2600 g) was mixed with water (260 g) and filled into a 5 L steel reactor. After inerting the reactor with nitrogen, a nitrogen pre-pressurization of 2 bar was applied. The mixture was heated to 120 °C, and butene oxide (50 g) was added to the reactor. Another batch of butene oxide (887 g) was added to the reactor over 12 hours. The product (3501 g) was separated after the reaction was complete.

[0378] analyze:

[0379] OH value (phthalic anhydride method, ISO 6796): 312 mg KOH / g

[0380] Amino value: 183 mg KOH / g

[0381] b) Polyetheramine D2000 (=Baxxodur EC 303) + 0.5BuO / NH:

[0382] Polyetheramine D2000 (3000 g) was mixed with water (300 g) and filled into a 5 L steel reactor. After inerting the reactor with nitrogen, a nitrogen pre-pressurization of 2 bar was applied. The mixture was heated to 100 °C, and butene oxide (50 g) was added to the reactor. Another batch of butene oxide (169 g) was added to the reactor over 12 hours. The product (3210 g) was separated after the reaction was complete.

[0383] analyze:

[0384] OH value (acetic anhydride method, ASTM E222): 86 mg KOH / g

[0385] Amino value: 53 mg KOH / g

[0386] c) Polyetheramine T5000 (=Baxxodur EC 311) + 0.5BuO / NH:

[0387] Polyetheramine T5000 (2068 g) was mixed with water (207 g) and filled into a 5 L steel reactor. After inerting the reactor with nitrogen, a nitrogen pre-pressurization of 2 bar was applied. The mixture was heated to 100 °C, and butene oxide (50 g) was added to the reactor. Another batch of butene oxide (40 g) was added to the reactor over 12 hours. The product (2138 g) was separated after the reaction was complete.

[0388] analyze:

[0389] OH value (acetic anhydride method, ASTM E222): 76 mg KOH / g

[0390] Amino value: 28 mg KOH / g

[0391] d) Polyetheramine T403 (=Baxxodur EC 310) + 0.5BuO / NH:

[0392] Polyetheramine T403 (2893 g) was mixed with water (289 g) and filled into a 5 L steel reactor. After inerting the reactor with nitrogen, a nitrogen pre-pressurization of 2 bar was applied. The mixture was heated to 120 °C, and butene oxide (50 g) was added to the reactor. Another batch of butene oxide (599 g) was added to the reactor over 12 hours. The product (3508 g) was separated after the reaction was complete.

[0393] analyze:

[0394] OH value (phthalic anhydride method, ISO 6796): 453 mg KOH / g

[0395] Amino value: 285 mg KOH / g

[0396] Example 1:

[0397] Poly(methylene diphenyl isocyanate) (pMDI) (16.52 g, f = 2.53) and anhydrous THF (250 g) were charged into a flask under N2 atmosphere and cooled in an ice bath. Compound “a)” (polyetheramine D400 + 0.5 BuO / NH) (16.65 g) was slowly added to anhydrous THF (50 g) 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 the 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.

[0398] Example 5

[0399] Toluene-2,4-diisocyanate (TDI T100) (3.00 g, 17 mmol) and anhydrous THF (150 g) were charged into a flask under a nitrogen atmosphere. Compound “d)” (polyetheramine T403 + 0.5 BuO / NH) (7.08 g) was slowly added to anhydrous THF (25 g) to form a polyurea. The reaction mixture was stirred until polymerization was complete, as confirmed by the disappearance of the NCO band in the IR spectroscopy. The THF was evaporated under reduced pressure (70 °C). 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 clear solid.

[0400] Table 1: The isocyanate used is PMDI

[0401]

[0402] Table 2: The isocyanate used is TDI

[0403]

[0404] 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.

[0405] 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.

Claims

1. A polyurea copolymer obtained by reacting the following substances: a. at least one polyisocyanate (A); and b. At least one isocyanate reactive component (B); The at least one polyisocyanate (A) wherein has an NCO functionality of ≥2.0 to ≤6.0; Component (B) is selected from compounds of formulas (B1a), (B1b), (B2a), (B2b), (B2c), (B2d), (B2e), (B2f), (B3a), and (B3b). Where n is an integer from 1 to 1000, Where n is an integer from 1 to 1000, Where x, y, and z are independent integers from 0 to 1000, and x + y + z are integers from 1 to 3000. Where x, y, and z are independent integers from 0 to 1000, and x + y + z are integers from 1 to 3000. Where t, x, y, and z are independent integers from 0 to 1000, and t+x+y+z are integers from 1 to 3000. Where t, x, y, and z are independent integers from 0 to 1000, and t+x+y+z are integers from 1 to 3000. Where x, y, and z are independent integers from 0 to 1000, and x + y + z are integers from 1 to 3000. Where x, y, and z are independent integers from 0 to 1000, and x + y + z are integers from 1 to 3000. Where x, y, and z are independent integers from 0 to 1000, and x + y + z are integers from 1 to 3000. Where x, y, and z are independent integers from 0 to 1000, and x + y + z are integers from 1 to 3000; The molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:10 to ≤10:1.

0.

2. The polyurea copolymer according to claim 1, wherein the at least one polyisocyanate (A) 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, m-phenylene 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-phenylene) (e.g., 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) 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-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-based adamantane, 3,3-diisocyanate-based bisadamantane, 3,3-diisocyanate-based ethyl-1'-bisadamantane, 1,2-bis(3-isocyanate-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-, Diazole, OCN(CH2)3O(CH2)2O(CH2)3NCO, OCH(CH2)3N(CH3)(CH2)3NCO, triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-triyltriisocyanate, ethyl l-lysine 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) Bis(hexamethylene)isocyanate, 1,3,5-triisocyanate-based benzene, bis(isocyanate-based hexyl)biuret, 3,3',3”-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triylbis(methylene)]tri[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanate-dicyclohexylmethane, triphenyl thiophosphate triisocyanate, 2,4,4'-diphenyl ether triisocyanate, and polymeric forms of diisocyanates and triisocyanates.

3. The polyurea copolymer according to claim 1, wherein the at least one polyisocyanate (A) contains urethane groups, isocyanurate groups, biuret groups, urea diketone groups, ureocarbamate groups, and / or imino groups. It exists in the form of dimers, trimers and oligomers of diazine dione.

4. The polyurea copolymer according to claim 1, wherein the at least one polyisocyanate (A) is selected from isophorone diisocyanate, hexamethylene-1,6-diisocyanate, 1,5-pentamethylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-2,4-diisocyanate, xylene-2,6-diisocyanate, 2,2'-biphenylene diisocyanate, 3,3'-biphenylene diisocyanate, 4, 4'-Bisphenylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, methylene-bis(4-phenylisocyanate), 2,2'-methylene-bis(cyclohexylisocyanate), 3,3'-methylene-bis(cyclohexylisocyanate), 4,4'-methylene-bis(cyclohexylisocyanate), triphenylmethane-4,4',4”-triisocyanate, toluene-2,4,6-trimethyltriisocyanate, 1,3,5-triisocyanate-phenylene, and diisocyanates and triisocyanates in polymeric forms.

5. The polyurea copolymer according to claim 1, wherein: n is an integer between 1 and 300; t, x, y, and z are independent integers from 0 to 300, provided that the sum of t+x+y+z is from 1 to 900.

6. The polyurea copolymer according to any one of claims 1-5, wherein the polyurea copolymer has a weight-average molecular weight Mw of 500-500,000 g / mol, determined according to DIN 55672, or, in the case of a high molecular weight in which the polymer material is no longer soluble in standard organic solvents, the molecular weight is determined according to MALDI-TOF mass spectrometry.

7. The polyurea copolymer according to claim 6, wherein the polyurea copolymer has a weight-average molecular weight Mw of 5000-50,000 g / mol.

8. The polyurea copolymer according to any one of claims 1-5, wherein the polyurea copolymer has a glass transition temperature of ≥-40°C to ≤250°C, determined according to ASTM D 3418 at a heating rate of 5 K / min.

9. The polyurea copolymer of claim 7, wherein the polyurea copolymer has a glass transition temperature of ≥-40°C to ≤250°C, determined according to ASTM D 3418 at a heating rate of 5 K / min.

10. A method for preparing a polyurea copolymer according to any one of claims 1-9, comprising at least the following steps: i) Provide at least one polyisocyanate (A) with an average NCO functionality of ≥2.0 to ≤6.0; ii) Provide at least one isocyanate reactive component (B); and iii) Make (A) and (B) come into contact; The at least one isocyanate reactive component (B) is a polyetheramine having at least two secondary amine functional groups and at least one hydroxyl functional group.

11. The method according to claim 10, wherein the molar ratio of NCO in the at least one polyisocyanate (A) to -NH- in the isocyanate reactive component (B) is ≥1.0:2.0 to ≤2.0:1.

0.

12. The method according to claim 10 or 11, wherein step iii) is performed at a temperature of ≥-50°C to ≤250°C.

13. The method according to claim 10 or 11, wherein the reaction is carried out in the presence of at least one solvent.

14. An article comprising a polyurea copolymer according to any one of claims 1-9 or a polyurea copolymer obtained according to any one of claims 10-13.

15. A method for remolding a polyurea copolymer according to any one of claims 1-9, or a polyurea copolymer obtained according to any one of claims 10-13, or an article according to claim 14, comprising at least the following steps: a) Applying pressure and heat to the polyurea copolymer to obtain a heated polyurea copolymer; and b) reshaping the polyurea copolymer of step a).

16. The method of claim 15, wherein the pressure is ≥5 × 10⁻⁶. 3 Pa to ≤10 7 Pa.

17. The method of claim 15, wherein the temperature is ≥60°C to ≤300°C.

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