Recyclable poly(urea-urethane) polymers and composites with dynamic hindered urea bonds (HUBs)

Abstract

The present invention relates to poly(urea-urethane) polymers, poly(urea-urethane) polymer composites, and methods for preparing the polymers and composites. Additionally, the present invention relates to methods for molding the polymers and the use of the polymers and their composites as repairable and recyclable materials.

Description

[Technical Field]

[0001] The present invention relates to poly(urea-urethane) polymers, poly(urea-urethane) polymer composites, and methods for making the polymers and composites. Additionally, the present invention relates to methods for molding the polymers and the use of the polymers and their composites as repairable and recyclable materials. [Background technology]

[0002] There is a need in materials and polymer chemistry to develop polymeric materials that have desirable in-use performance characteristics and are also malleable, healable, and shape-reprogrammable. There is also a need to develop polymers that can degrade or reversibly depolymerize. While shape-memory polymers and self-healing polymers are known, many of these polymers lack both the desired performance and dynamic properties. With regard to degradable or reversibly depolymerizable polymers, these polymers often lack the required in-use performance characteristics, degrade too easily, or, on the other hand, do not degrade as easily or quickly as desired.

[0003] Furthermore, polymer-based composites, including glass fiber reinforced plastics (GFRP), are widely used in applications such as airplanes, boats, or wind turbine blades. Over 10 million tonnes of GFRP are produced each year, but once incorporated into polymers, no viable recycling concept exists. Summary of the Invention [Problem to be solved by the invention]

[0004] Therefore, there is a need to provide new polymers. It is therefore an object of the present invention to provide novel polymers, in particular poly(urea-urethane) polymers, obtained from isocyanates, amines and polyols that can be used in composites and that are easily repairable and recyclable. [Means for solving the problem]

[0005] Surprisingly, it has been found that the polymers of the present invention enable the creation of composite materials that can be easily repaired and recycled, while also being usable in many applications. Indeed, the poly(urea-urethane) polymers of the present invention possess dynamic hindered urea bonds (HUBs), which function as dynamic covalent bonds in a covalently adaptive system / network (CAS / CAN). Therefore, it is believed that the introduction of bulky substituents on the nitrogen atom weakens the bond, resulting in a dissociation equilibrium between open and closed bonds, which is shifted toward the open side by increasing the temperature. The HUBs are split into their original constituent groups (depolymerization). The claimed materials are easily processable by thermomechanical processing methods, as shown below, facilitating chemical and mechanical recycling of the poly(urea-urethane) polymers.

[0006] Therefore, the present invention provides The following ingredients (i) at least one isocyanate; (ii) at least one polyol; and (iii) at least one secondary amine having the formula (I): 1. The method of claim 1, further comprising reacting a poly(urea-urethane) polymer obtained by the method of claim 1, wherein the poly(urea-urethane) polymer is a poly(urea-urethane) polymer obtained by the method of claim 1. [ka] (In the formula, -R a - is -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10-, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 -Z1-; -Z1- is a substituted or unsubstituted straight or branched chain C1-C 30 is alkylene; -Z2- is a substituted or unsubstituted straight or branched chain 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted straight or branched chain C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 is cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 is cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 to C 30 is arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z 11 - is C6-C substituted with -NHR or -OR 30 arylene, where R is H and substituted or unsubstituted straight or branched chain C1-C 10 selected from the group consisting of alkyl; -Z 12 - is -N(R f )-and; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z 13 At least one of the one or more heteroatoms in aDerived from; C a is a C atom or H atom, and C b is a C atom or H atom, and C a and C b at least one of which is a C atom; X a is an O atom or NH, and X b is an O atom or NH, and X a and X b At least one of X is NH, a and / or X b When is NH, each C a and / or C b is a C atom; where: (A)R c , R d , R f and R g are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl; R b and R e are independent of each other and R c , R d , R f and R g defined as; or R b and R e does not exist, and C a and C b are bonded to each other through a single bond, and C a , C b , X a , X b and R a or forming a heterocyclic ring consisting of (B)C a and R e is a substituted or unsubstituted C6-C 30 Forming an arylene, R f and R g does not exist; and C b and R b is a substituted or unsubstituted C6-C 30 Forming an arylene, R c and R d does not exist; or (C)-C a and R e is a substituted or unsubstituted C6-C 30 Forming an arylene, R f and R g does not exist; or -C b and R b is a substituted or unsubstituted C6-C 30 Forming an arylene, R c and R d None of the are present; where C a and R e Substituted or unsubstituted C6-C 30 When forming an arylene, Rb , R c and R d are independent of each other under (A) R c , R d , R f and R g is defined as any one of the following: where C b and R b Substituted or unsubstituted C6-C 30 When forming an arylene, R e , R f and R g are independent of each other under (A) R c , R d , R f and R g (defined as one of the following:

[0007] Preferably, the at least one secondary amine (iii) has the following formula (I): [ka] (In the formula, -R a - is -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 -Z1-; -Z1- is a substituted or unsubstituted straight or branched chain C1-C 30 is alkylene; -Z2- is a substituted or unsubstituted straight or branched chain 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted straight or branched chain C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 is cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 is cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 to C 30 is arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z 11 - is C6-C substituted with -NHR or -OR 30 arylene, where R is H and substituted or unsubstituted straight or branched chain C1-C 10 selected from the group consisting of alkyl; -Z 12 - is -N(R f )-and; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z 13 At least one of the one or more heteroatoms in a derived from); C a is a C atom or H atom, and C b is a C atom or H atom, and C a and C b at least one of which is a C atom; X a is an O atom or NH, and X b is an O atom or NH, and Xa and X b At least one of X is NH, a and / or X b When is NH, each C a and / or C b is a C atom; where: (A)R c , R d , R f and R g are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl; R b and R e are independent of each other and R c , R d , R f and R gdefined as; or R b and R e does not exist, and C a and C b are bonded to each other through a single bond, and C a , C b , X a , X b and R a or forming a heterocyclic ring consisting of (B)C a and R e is a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and R f and R g does not exist; and C b and R b is a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and R c and R d Neither of these exist.

[0008] Preferably, C a and C b are C atoms.

[0009] Preferably, X a is NH and X b is NH, and the secondary amine (iii) is of the following formula (II): [ka] (In the formula, C a , C b , R b , R c , R d , R e , R f , R g , and -R a - is as defined in formula (I) It has.

[0010] Preferably, -R a-, -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z9-Z1-Z9-, -Z1-Z5-Z1-, -Z1-Z9-Z1-, and -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), preferably -Z2-, -Z9-Z1-Z9-, and -Z9-Z1 (-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), more preferably -Z2- and -Z9-Z1 (-Z 11 -Z1) n -Z9-, (where n=1, 2, 3, 4, 5, or 6).

[0011] Preferably, -Z1- is -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH2-CH(CH2CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, and -(CH2) 10 - is selected from the group consisting of

[0012] Preferably, R a But -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 When selected from the group consisting of -Z1-, -Z1- is -CH2-.

[0013] Preferably, -Z9- is selected from the group consisting of phenylene, naphthylene, biphenylene, fluorenylene, and indenyl, and more preferably -Z9- is phenylene. Preferably, phenylene is selected from the group consisting of ortho-phenylene, meta-phenylene, and para-phenylene, and more preferably ortho- and para-phenylene.

[0014] Preferably, -R a - is -Z9-Z1-Z9-, -Z9- is phenylene, more preferably para-phenylene, and -Z1- is -CH2-.

[0015] Preferably, -R a - is -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), -Z9- is phenylene, -Z1- is -CH2-, and -Z 11 - is a C6-arylene substituted with -NHR.

[0016] Preferably, -Z 11 - In the formula, R is -C(R h )(R i )(R j ), where R h , R i and R j are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 More preferably, R is selected from the group consisting of alkylene, 5- to 30-membered heteroaryl. h , R i and R j are, independently of one another, hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. More preferably, R h , R i and R j are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of hydrogen, methyl, and ethyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl. More preferably, R h , R i and R j One of the following is H and R h , R i and R j and one of R other than H is CH3. More preferably, R h , R i and R jOne of the groups other than CH3 or H is an ethyl group.

[0017] Alternatively, preferably, -Z 11 - In the formula, R is -C(R h )(R i )(R j ) where C and R h is substituted or unsubstituted C6-C 30 Forming an arylene, R i and R j For example, -Z 11 - can be -NH-Ph.

[0018] In the context of the present invention, -Z2- is preferably a substituted or unsubstituted straight-chain or branched-chain 2- to 500-membered heteroalkylene, more preferably a substituted or unsubstituted straight-chain or branched-chain 2- to 35-membered heteroalkylene, more preferably a substituted or unsubstituted straight-chain or branched-chain 2- to 30-membered heteroalkylene.

[0019] More preferably, -Z2- is -CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-NH-CH2-CH2-CH2- -CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2- O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, [CH(CH3)-CH2-O] m1-CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(where R x1 is -CH2-CH3, and R y1 is [-O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ) and m1+n1+o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C(R l )(R m )(R n ) and m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O] o3 -CH2-CH(CH)3- (where n3 is in the range of 8-10, and m3 + o3 is in the range of 3-4, or n3 is in the range of 12-13 and m3+o3 is in the range of 5-7, or n3 is in the range of 38-40, and m3+o3 is in the range of 5-7). -[CH-CH2-O] m4 -CH2-CH2- (where m4 ranges from 8 to 250), and -[CH2-CH2-NH] m5 - (where m5 is in the range of 10 to 100,000).

[0020] More preferably, -Z2- is -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1-, where R x1 is -CH2-CH3, and R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ) and m1+n1+o1 is in the range of 5 to 6.

[0021] Preferably, R y1 and R y2 In one or more of the following, R l , R m and R n are, independently of one another, hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 More preferably, R is selected from the group consisting of alkylene, 5- to 30-membered heteroaryl. l , R m and R nare, independently of one another, hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. More preferably, R l , R m and R n are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl. More preferably, R l , R m and R n One of the following is H and R l , R m and R n and one of R other than H is CH3. More preferably, R l , R m and R n and one of R other than CH or H is an ethyl group. Alternatively, preferably, R y1 and R y2 In one or more of the following, C and R l is substituted or unsubstituted C6-C 30 Forming an arylene, R m and R n For example, R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-Ph, and R y2 is [-O-CH2-CH(CH3)] n2 It can be —NH—Ph.

[0022] Preferably, -Z3- is selected from the group consisting of -CH=CH- and -CH2-CH=CH-.

[0023] Preferably, -Z4- is selected from the group consisting of -CH=CH-NH-, -CH=CH-O-, and -CH=CH-CH2-O-.

[0024] Preferably, -Z5- is cyclohex-1,4-ylene, cyclohex-1,3-ylene, [ka] and 2,6-diyl-norbornane.

[0025] Preferably, -Z6- is selected from the group consisting of 1,5-dioxaoctylene and 4,8-dioxabicyclo[3.3.0]octylene.

[0026] Preferably, -Z7- is selected from the group consisting of cyclopent-1,2-en-3,5-ylene, 3-cyclohexen-1,2-ylene, 2,5-cyclohexadiene-1,4-ylene, cyclohex-1,2-en-3,5-ylene, 2,5-cyclohexadiene-1,4-ylene and cyclohept-1,2-en-3,5-ylene.

[0027] Preferably, -Z 10 - is triazinylene, more preferably one or more of vic-triazinylene, asym-triazinylene, and sym-triazinylene.

[0028] Preferably, R c , R d , R f, , and R gare, independently of one another, hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl, and —C(OH)HR k more preferably selected from the group consisting of hydrogen, methyl, and ethyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl; where R k is hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10alkylene and 5- to 30-membered heteroaryl.

[0029] Preferably, R b and R e are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl.

[0030] Preferably, R b , R c , and R d One of the following is H and R e , R f , and R g one of which is H; b , R c , and R d One of the H groups is CH3, and the other is R e , R f , and R g One of the atoms other than H is CH3.

[0031] Preferably, R b , R c , and R d is an ethyl group, and R e , R f , and R g is an ethyl group; more preferably R b , R c , and R d Of these, one is H except for the ethyl group, R e , R f , and Rg Of these, one is H except for the ethyl group, R b , R c , and R d Of these, one other than the ethyl group or H is CH3, R e , R f , and R g Of these, one other than an ethyl group or H is CH3.

[0032] Preferably, at least one secondary amine (iii) is [ka] 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA).

[0033] Alternatively, preferably, the at least one secondary amine (iii) is a sec-butyl-modified polyetheramine, CH3-CH2-CH(CH3)-NH-[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -NH-CH(CH3)-CH2-CH3 (wherein R x1 is -CH2-CH3, and R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-CH(CH3)-CH2-CH3, and m1+n1+o1 is in the range of 5 to 6).

[0034] Preferably, the at least one secondary amine (iii) is [ka] DIB-Polyetheramine T403 (m1+n1+o1=5-6).

[0035] Alternatively, it is preferred that the at least one secondary amine (iii) is DIB-butanediamine (N,N'-di-sec-butyl-1,4-butanediamine).

[0036] Alternatively, it is preferred that the at least one secondary amine (iii) is 2-(ethylamino)ethanol.

[0037] In the context of the present invention, suitable isocyanates are known per se to those skilled in the art.

[0038] Preferably, the NCO functionality of at least one isocyanate (i) is 2 or greater, more preferably 2 or 3.

[0039] Preferably, the at least one isocyanate (i) is a mixture of an isocyanate with an NCO functionality of 2 and an isocyanate with an NCO functionality of 3 or more, more preferably the at least one isocyanate (i) is a mixture of an isocyanate with an NCO functionality of 2 and an isocyanate with an NCO functionality of 3.

[0040] Preferably, the at least one isocyanate (i) is selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), mixtures of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), tolylene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, xylene 2,6-diisocyanate, naphthylene 1,5-diisocyanate (1,5-NDI), butane 1,4-diisocyanate, pentane 1,5-diisocyanate Diisocyanate (PDI), hexane 1,6-diisocyanate (HDI), octane 1,8-diisocyanate, nonane 1,9-diisocyanate, decane 1,10-diisocyanate, 2,2-dimethylpentane 1,5-diisocyanate, 2-methylpentane 1,5-diisocyanate (MPDI), 2,4,4 (or 2,2,4)-trimethylhexane 1,6-diisocyanate (TMDI), cyclohexane 1,3- and 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), methylene-bis(cyclohexyl isocyanate) (H12 mDI), 2,4- or 2,6-diisocyanato-1-methylcyclohexane (H6TDI), 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane (AMCI), 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane-4,4',4"-triisocyanate, toluene-2,4,6-triyl Triisocyanate, ethyl ester 1-lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, triisocyanatomethylcyclohexane, 1,8-diisocyanato-4-(isocyanatomethyl)octane, undecane 1,6,11-triisocyanate, 1,7-diisocyanato-4-(3-isocyanatopropyl)heptane, 1,6-diisocyanato-3-(isocyanatomethyl)hexane, 2,2-Bis[[4-(isocyanatomethyl)phenyl]methyl]butyl n-[[4-(isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)tris(hexamethylene)isocyanate, 1,3,5-triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3"-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyltris(isocyanatomethyl)phenyl]methyl] (methylene)]tris[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanato-dicyclohexylmethane, triisocyanatotriphenylthiophosphate, 2,4,4'-diphenyl ether triisocyanate, 1,3-bis(3-isocyanato-4-methylphenyl)-1,3-diazetidine-2,4-dione, and mixtures of two or more thereof; More preferably, it is selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), tolylene diisocyanate (TDI), naphthylene 1,5-diisocyanate (1,5-NDI), 1,4-diisocyanate, pentane 1,5-diisocyanate (PDI), hexane 1,6-diisocyanate (HDI), methylene-bis(cyclohexyl isocyanate) (H12 mDI), e.g., dicyclohexylmethane 4,4'- or 2,4'- or 2,2'-diisocyanate, and mixtures of two or more thereof.

[0041] Preferably, the at least one isocyanate (i) is selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI) and tolylene diisocyanate (TDI).

[0042] Preferably, the at least one isocyanate (i) is selected from the group consisting of methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI) and mixtures of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), more preferably selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI) and mixtures of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI).

[0043] More preferably, the tolylene diisocyanate (TDI) comprises, more preferably consists of, one or more of 2,4-TDI and 2,6-TDI.

[0044] More preferably, the monomeric methylene diphenylene diisocyanate (mMDI) comprises, more preferably consists of, one or more of 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI), 2,2'-meta-ylene(diphenyl diisocyanate) (2,2'-MDI) and 2,4'-meta-ylene(diphenyl diisocyanate) (2,4'-MDI), more preferably 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI). More preferably, the at least one isocyanate (i) is a monomeric methylene diphenylene diisocyanate (mMDI), which comprises, more preferably consists of, one or more of 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene(diphenyl diisocyanate) (2,2'-MDI) and 2,4'-methylene(diphenyl diisocyanate) (2,4'-MDI), more preferably 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI).

[0045] Other possible isocyanates are listed, by way of example, in "Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes]", Carl Hanser Verlag, 3rd edition 1993, Chapters 3.2 and 3.3.2.

[0046] Suitable polyols are known per se to those skilled in the art.

[0047] In principle, any polyol conventionally used in the preparation of polyurethanes can be used as the polyol. The type of polyol may vary depending on the desired purpose of the application. Suitable polyols include polyester polyols, particularly aliphatic polyester polyols and aliphatic-aromatic polyester polyols, polyester carbonate polyols, polyether ester polyols, aliphatic polycarbonate polyols, polyacrylate polyols, polyolefin polyols, aliphatic polyether ols, and mixtures thereof. Preferably, at least one polyol is selected from polyester polyols, particularly aliphatic polyester polyols and aliphatic-aromatic polyester polyols, aliphatic polycarbonate polyols, aliphatic polyether ols, and mixtures thereof. In particular, the at least one polyol comprises a polyester polyol and / or an aliphatic polyether polyol described herein. In particular, the at least one polyol is selected from polyester polyols, aliphatic polyether polyols, and combinations thereof.

[0048] Preferably, the at least one polyol (i) is selected from the group consisting of polyester polyols, polyetherester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols, and mixtures thereof.

[0049] More preferably, the at least one polyol (i) is selected from the group consisting of polyester polyols and polyether polyols.

[0050] Suitable polyester polyols as polyols are in particular aliphatic polyesterols and aliphatic / aromatic polyesterols, i.e. polyesterols based on a dicarboxylic acid component selected from aliphatic dicarboxylic acids, cycloaliphatic dicarboxylic acids, aromatic dicarboxylic acids and combinations, and a diol component selected from aliphatic diols, cycloaliphatic diols and polyether polyols.

[0051] Aliphatic diols suitable for preparing polyester polyols generally have 2 to 20 C atoms, in particular 3 to 10 C atoms. Examples of aliphatic diols include ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,2-diol, butane-1,3-diol, butane-1,4-diol, butane-2,3-diol, pentane-1,2-diol, pentane-1,3-diol, pentane-1,4-diol, pentane-1,5-diol, pentane-2,3-diol, pentane-2,4-diol, hexane-1,2-diol, hexane-1,3-diol, hexane-1,4-diol, hexane-1,5-diol, hexane-1,6-diol, hexane-2,5-diol, heptane-1,2-diol, 1,7-heptanediol, 1,8-octanediol, 1,2-octanediol, and 1,9-nonanediol. hexanediol, 1,2-decanediol, 1,10-decanediol, 1,2-dodecanediol, 1,12-dodecanediol, 1,5-hexadiene-3,4-diol, neopentyl glycol (2,2-dimethylpropane-1,3-diol), 2,2-diethylpropane-1,3-diol, 2-methyl-2-ethylpropane-1,3-diol, 2-methyl-2,4-pentanediol, 2,4-dimethyl-2,4-pentanediol, 2-ethyl-1,3-hexanediol, 2,5-dimethyl-2,5-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, pinacol, diethylene glycol, triethylene glycol, dipropylene glycol, and tripropylene glycol.

[0052] Cycloaliphatic diols suitable for preparing polyester polyols generally have 4 to 20 carbon atoms, in particular 5 to 10 carbon atoms. Examples of cycloaliphatic diols are cyclopentanediol, cyclohexane-1,4-diol, cyclohexane-1,2-dimethanol, cyclohexane-1,3-dimethanol, cyclohexane-1,4-dimethanol and 2,2,4,4-tetramethylcyclobutane-1,3-diol. Also suitable diols for preparing polyester polyols are polyether diols, in particular polyethylene glycol HO(CHCHO)H, higher polypropylene glycol HO(CH[CH]CHO)H (where n is an integer and n≧4, for example, 4 to 20), and polyethylene-polypropylene glycols, more specifically those having 4 to 20 repeating units (the arrangement of the ethylene oxide and propylene oxide units can be block or random), and polytetramethylene glycols, more specifically those having 4 to 20 repeating units, and poly-1,3-propanediol, more specifically those having 4 to 20 repeating units.

[0053] Preferred dicarboxylic acids for preparing the polyester polyols are aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid, cycloaliphatic dicarboxylic acids preferably having 8 to 12 carbon atoms, such as tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexanedicarboxylic acid, and aliphatic dicarboxylic acids preferably having 3 to 40 carbon atoms, such as malonic acid, succinic acid, 2-methylsuccinic acid, glutaric acid, 2-methylglutaric acid, 3-methylglutaric acid, α-ketoglutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, brassylic acid, fumaric acid, 2,2-dimethylglutaric acid, suberic acid, diglycolic acid, oxaloacetic acid, glutamic acid, aspartic acid, itaconic acid and maleic acid, and dimeric fatty acids such as those obtained by dimerization of octadecadienoic acid or other polyunsaturated fatty acids or fatty acid mixtures [CAS 61788-89-4].

[0054] The dicarboxylic acids used for the preparation of the polyester polyols may be the free acids or their ester-forming derivatives, which are preferably understood to be the corresponding anhydrides, mono- and di-alkyl esters, preferably mono- and di-C1-C4 alkyl esters, more preferably monomethyl and dimethyl esters, and the corresponding monoethyl and diethyl esters, as well as monovinyl and divinyl esters, and mixed esters, examples of which are mixed esters with different C1-C4 alkyl moieties.

[0055] Among the polyester polyols, polyester polyols based on a diol component selected from the group consisting of butanediol, neopentyl glycol, hexanediol, ethylene glycol, diethylene glycol, and mixtures thereof, and a dicarboxylic acid component selected from the group consisting of adipic acid, phthalic acid, isophthalic acid, and combinations thereof, are preferred. Polyester polyols based on butanediol and / or neopentyl glycol and / or hexanediol and adipic acid and / or phthalic acid and / or isophthalic acid are particularly preferred.

[0056] Suitable polyester polyols as polyols also include polylactones, especially poly-C4-C12-lactones, especially polycaprolactone (PCL). Polylactone refers to aliphatic polyesters obtained by ring-opening polymerization of lactones, especially C4-C12-lactones, especially epsilon-caprolactone (ε-caprolactone). Polycaprolactones have the general formula [-O-CHR-(CH2) m-CO-] (where m is 4 to 10, and in the case of caprolactone, m=4 and R is hydrogen). In the context of the present invention, the term polycaprolactone is understood to mean both homopolymers of epsilon-caprolactone and copolymers of epsilon-caprolactone. Suitable copolymers are, for example, copolymers of epsilon-caprolactone with monomers selected from the group consisting of lactic acid, lactide, hydroxyacetic acid and glycolide. Polyester polyols are conventional components known, for example, from Ullmanns Encyklopadie der technischen Chemie [Ullmann's Encyclopedia of Industrial Chemistry], 4th edition, volume 19, pp. 62-65.

[0057] Aliphatic polyether polyols suitable as polyols are polyaddition products of C2-C4 alkylene oxides, such as ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, or 2-methylpropylene oxide. Further suitable polymer polyols include aliphatic polyether polyols obtained by condensation of polyhydric aliphatic alcohols, aliphatic polyether polyols obtained by alkoxylation of aliphatic polyhydric alcohols, amines, and amino alcohols. Suitable polyhydric alcohols include ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, trimethylolpropane, glycerol, pentaerythritol, triethanolamine (=tris(2-hydroxyethyl)amine), sorbitol, or mixtures thereof. Suitable polyether polyols generally have an OH functionality in the range of 1.5 to 3.0, particularly in the range of 1.8 to 2.5. Suitable polyetherols preferably have an OH number in the range of 20 to 300 mg KOH / g, in particular in the range of 30 to 250 mg KOH / g. In the context of the present invention, the OH number is determined in accordance with EN ISO 4629-1:2016, unless otherwise stated.

[0058] Generally, their number-average molecular weights Mn, as measured by gel permeation chromatography, are in the range of 400 to 10,000 g / mol, preferably 500 to 5,000 g / mol. Preferred polyether components are polyethylene oxide polyols, polypropylene oxide polyols, and polytetramethylene oxide polyols (polyTHF) with molecular weights Mn of 400 to 10,000 g / mol, preferably 500 to 5,000 g / mol. In this case, low-molecular-weight polyether polyols may be water-soluble, especially if they have a high corresponding OH content.

[0059] Preferably, the at least one polyol (ii) is a polyether polyol, more preferably selected from the group consisting of polytetrahydrofuran, trifunctional polyether polyols containing secondary hydroxyl groups, polypropylene glycol, polyether polyols based on sucrose, tetrafunctional polyether polyols based on ethylene diamine and propylene oxide, and mixtures of two or more thereof, more preferably selected from the group consisting of polytetrahydrofuran and trifunctional polyether polyols containing secondary hydroxyl groups.

[0060] Preferably, the at least one polyol (ii) is a polyether polyol, more preferably polytetrahydrofuran (f=2, Mn=2000 g / mol, OH=56 mg KOH / g), trifunctional polyether polyols containing secondary hydroxyl groups (f=3, Mn=3500 g / mol, OH=48, viscosity (25°C)=600 mPa·s; or f=3, Mn=3000 g / mol, OH=53 mg KOH / g, viscosity (25°C)=553 mPa·s), polypropylene glycol (f=2, Mn=500 g / mol, OH=248 mg KOH / g, viscosity (25°C)=72 mPa·s), sucrose-based polyether polyols (f=5, Mn=500 g / mol, OH=490 mg KOH / g, viscosity (25°C)=8450 mPa·s). The preferred polyether polyols are selected from the group consisting of tetrafunctional polyether polyols based on ethylenediamine and propylene oxide (f=4, Mn=300 g / mol, OH=753 mg KOH / g, viscosity at 25°C=42,000 mPa·s), and mixtures of two or more thereof, more preferably polytetrahydrofuran (f=2, Mn=2,000 g / mol, OH=56 mg KOH / g) and trifunctional polyether polyols containing secondary hydroxyl groups (f=3, Mn=3,500 g / mol, OH=48, viscosity at 25°C=600 mPa·s; or f=3, Mn=3,000 g / mol, OH=53 mg KOH / g, viscosity at 25°C=553 mPa·s). Viscosity at 25°C: DIN 53 240, OH value according to DIN EN 12092.

[0061] Alternatively, aliphatic polycarbonate polyols suitable as polyols can be obtained by reacting carbonic acid derivatives, such as diphenyl carbonate, dimethyl carbonate, or phosgene, with diols. Useful diols of this type include, for example, ethylene glycol, propane-1,2- and -1,3-diol, butane-1,3- and 1,4-diol, hexane-1,6-diol, octane-1,8-diol, neopentyl glycol, 1,4-bishydroxymethyl-cyclohexane, 2-methylpropane-1,3-diol, 2,2,4-trimethylpentane-1,3-diol, dipropylene glycol, polypropylene glycol, dibutylene glycol, polybutylene glycol, and lactone-modified diols. The diol component preferably contains 40% to 100% by weight of hexane-1,6-diol and / or hexanediol derivatives, preferably those having ether or ester groups and terminal OH groups, such as products obtained by reacting 1 mole of hexanediol with at least 1 mole, preferably 1 to 2 moles, of ε-caprolactone, or by etherifying hexanediol with itself to give di- or trihexylene glycol. Polyether polycarbonate polyols can also be used. Among aliphatic polycarbonate polyols, polycarbonate polyols based on dimethyl carbonate and hexanediol and / or butanediol and / or ε-caprolactone are preferred. Polycarbonate polyols based on dimethyl carbonate and hexanediol and / or ε-caprolactone are very particularly preferred. The molecular weight Mn of the preferred polycarbonate polyols is 400 to 10,000 g / mol, preferably 500 to 5,000 g / mol, as measured by gel permeation chromatography as described above.

[0062] Other possible polyols are listed, by way of example, in "Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes]", Carl Hanser Verlag, 3rd edition 1993, Chapters 3.1, 3.2 and 3.3.2.

[0063] Preferably, the at least one isocyanate (i), the at least one polyol (ii) and the at least one secondary amine (iii) are reacted in the absence of a solvent.

[0064] Preferably, the poly(mochevinoi) polymer is obtained or has been obtained by a process comprising reacting (i), (ii) and / or (iii), more preferably (i) and (ii), with at least one additive, wherein the at least one additive is selected from the group consisting of benzoyl chloride and diethylene glycol bischloroformate.

[0065] In the reactions (i), (ii) and / or (iii), additives known to those skilled in the art other than those mentioned above may be used.

[0066] Preferably, the poly(mochevinoi) polymer is obtained or has been obtained in the absence of a catalyst.

[0067] Preferably, the poly(mochevinoi) polymer is - reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; - reacting the resulting prepolymer with at least one secondary amine (iii); or - reacting at least one isocyanate (i) with at least one secondary amine (iii) to obtain a prepolymer; - reacting the resulting prepolymer with at least one polyol (ii); obtained or obtained by a process comprising:

[0068] Preferably, the molar ratio of —NCO of the at least one isocyanate (i) to —OH of the at least one polyol (ii) is in the range of 1:0.50 to 1:0.10, more preferably in the range of 1:0.40 to 1:0.15, more preferably in the range of 1:0.30 to 1:0.20.

[0069] Preferably, the molar ratio of —NCO of the at least one isocyanate (i) to —NH of the at least one secondary amine (iii) is in the range of 1:1.50 to 1:0.5, more preferably in the range of 1:1.20 to 1:0.60, more preferably in the range of 1:0.8 to 1:0.7.

[0070] Preferably, the reaction of components (i), (ii) and / or (iii) is carried out at a temperature in the range of from above 0 to 200°C, more preferably in the range of from 1 to 200°C, more preferably in the range of from 10 to 150°C, more preferably in the range of from 20 to 90°C.

[0071] Preferably, the poly(urea-urethane) polymer is obtained or is obtainable by a process further comprising curing the mixture of (i), (ii) and (iii), more preferably at a temperature in the range of 90 to 200°C, more preferably at a temperature in the range of 100 to 150°C.

[0072] Preferably, the poly(urea-urethane) polymer is thermoplastic or thermoset.

[0073] Preferably, the poly(urea-urethane) polymers of the present invention are covalently adaptable polymers, preferably covalently adaptable network (CAN) thermosets or covalently adaptable system (CAS) / thermoplastics.

[0074] Preferably, the poly(urea-urethane) polymers of the present invention are recyclable.

[0075] Preferably, the solubility of the poly(urea-urethane) polymer in toluene is in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer:mL of solvent) measured after heating at a temperature of 110° C. and ambient pressure for at least 12 hours, and more preferably, the solubility of the poly(urea-urethane) polymer in toluene is in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer:mL of solvent) measured after heating at a temperature of 110° C. and ambient pressure for at least 12 hours.

[0076] Preferably, the solubility of the poly(urea-urethane) polymer in 1,3-dimethyl-2-imidazolidinone is in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer:mL of solvent) measured after heating at a temperature of 130° C. and ambient pressure for at least 20 hours, and more preferably, the solubility of the poly(urea-urethane) polymer in organic solvent is in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer:mL of solvent) measured after heating at a temperature of 130° C. and ambient pressure for at least 20 hours.

[0077] Preferably, the melting point of the poly(urea-urethane) polymer is in the range of 10°C to 200°C at a pressure of 880 kPa as determined by hot pressing (preferably using a 17 cm diameter circular press and a 20 kN applied pressure), more preferably in the range of 50°C to 190°C at a pressure of 880 kPa as determined by hot pressing (preferably using a 17 cm diameter circular press and a 20 kN applied pressure), more preferably in the range of 60°C to 180°C at a pressure of 880 kPa as determined by hot pressing (preferably using a 17 cm diameter circular press and a 20 kN applied pressure).

[0078] The present invention further comprises: The following ingredients (i) at least one isocyanate; (ii) at least one polyol; and (iii) at least one secondary amine having the following formula (I): to obtain a mixture comprising a poly(urea-urethane) polymer, more preferably a poly(urea-urethane) polymer described herein; and The resulting mixture was treated with (iv): (iv) a filler selected from the group consisting of glass fiber, carbon fiber, mineral fiber, fabric, metal mesh, metal fiber, metal rod, carbonate, wood, and mixtures of two or more thereof; and a poly(urea-urethane) polymer-based composite material obtained by or obtained by contacting: [ka] (In the formula, -R a - is -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 -Z1-; -Z1- is a substituted or unsubstituted straight or branched chain C1-C 30 is alkylene; -Z2- is a substituted or unsubstituted straight or branched chain 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted straight or branched chain C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 is cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 is cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 to C 30 is arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z 11 - is C6-C substituted with -NHR or -OR 30 arylene, where R is H and substituted or unsubstituted straight or branched chain C1-C 10 selected from the group consisting of alkyl; -Z 12 - is -N(R f )-and; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z 13 At least one of the one or more heteroatoms in a Derived from; C a is a C atom or H atom, and C b is a C atom or H atom, and C a and C b at least one of which is a C atom; X a is an O atom or NH, and X b is an O atom or NH, and X a and X b At least one of X is NH, a and / or X b When is NH, each C a and / or Cb is a C atom; where: (A)R c , R d , R f and R g are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl; R b and R e are independent of each other and R c , R d , R f and R g defined as; or R b and R e does not exist, and C a and C b are bonded to each other through a single bond, and C a, C b , X a , X b and R a or forming a heterocyclic ring consisting of (B)C a and R e is a substituted or unsubstituted C6-C 30 Forming an arylene, R f and R g does not exist; and C b and R b is a substituted or unsubstituted C6-C 30 Forming an arylene, R c and R d does not exist; or (C)- C a and R e is a substituted or unsubstituted C6-C 30 Forming an arylene, R f and R g does not exist; or - C b and R b is a substituted or unsubstituted C6-C 30 Forming an arylene, R c and R d None of the are present; where C a and R e Substituted or unsubstituted C6-C 30 When forming an arylene, R b , R c and R d are independent of each other under (A) R c , R d , R f and R g is defined as any one of the following: where C b and R b Substituted or unsubstituted C6-C 30 When forming an arylene, R e , R f and R g are independent of each other under (A) R c , R d , Rf and R g (defined as one of the following:

[0079] Preferably, the at least one secondary amine (iii) has the following formula (I): [ka] (In the formula, -R a - is -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 -Z1-; -Z1- is a substituted or unsubstituted straight or branched chain C1-C 30 is alkylene; -Z2- is a substituted or unsubstituted straight or branched chain 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted straight or branched chain C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 is cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 is cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 to C 30 is arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z 11 - is C6-C substituted with -NHR or -OR 30 arylene, where R is H and substituted or unsubstituted straight or branched chain C1-C 10 selected from the group consisting of alkyl; -Z 12 - is -N(R f )-and; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z 13 At least one of the one or more heteroatoms in a derived from); C a is a C atom or H atom, and C b is a C atom or H atom, and C a and C b at least one of which is a C atom; X a is an O atom or NH, and X b is an O atom or NH, and X a and X b At least one of X is NH, a and / or X b When is NH, each C a and / or C b is a C atom; where: (A)R c , R d , R f , and R g are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl; R b and R e are independent of each other and R c , R d , R f , and R g defined as; or R b and R e does not exist, and C a and C b are bonded to each other through a single bond, and C a , C b , X a , X b、 and R a or forming a heterocyclic ring consisting of (B)C a and R e is a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and R f and Rg does not exist; and C b and R b is a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and R c and R d Neither of these exist.

[0080] Preferably, the filler (iv) is glass fiber.

[0081] Preferably, the at least one polyol, the at least one isocyanate, and the at least one secondary amine are as defined above for the poly(urea-urethane) polymer.

[0082] The present invention further provides a method for producing the poly(urea-urethane) polymers of the present invention, comprising the steps of: (a) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; (b) contacting the prepolymer obtained in (a) with at least one secondary amine, wherein the at least one secondary amine has formula (I) according to the present invention, to obtain a poly(urea-urethane) polymer; or (a') reacting at least one isocyanate (i) with at least one secondary amine, the at least one secondary amine having the formula (I) according to the present invention, to obtain a prepolymer; (b') contacting the prepolymer obtained in (a') with at least one polyol (ii), a poly(urea-urethane) polymer. The present invention relates to a method, comprising:

[0083] Preferably, (a) or (a') is carried out at a temperature in the range of 0 to 200°C, more preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0084] Preferably, one or more of (a) and (b) or one or more of (a') and (b'), more preferably (a) and (b) or (a') and (b'), is carried out in the absence of a solvent.

[0085] Preferably, (b) or (b') is carried out at a temperature in the range of 0 to 200°C, more preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0086] Preferably, the method comprises: (c) curing the mixture obtained in (b) or (b') at a temperature preferably in the range of 90 to 150°C, more preferably in the range of 100 to 120°C. Further includes:

[0087] Furthermore, the present invention relates to a method for producing a composite material according to the invention, said method comprising the steps of: (1) providing a poly(mochevinoi) polymer; (1.1) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; (1.2) contacting the prepolymer obtained in (1.1) with at least one secondary amine, wherein the at least one secondary amine (iii) has formula (I) as defined in the present invention; or (1.1') reacting at least one isocyanate (i) with at least one secondary amine (wherein the at least one secondary amine (iii) has formula (I) as defined in the present invention) to obtain a prepolymer; (1.2') contacting the prepolymer obtained in (1.1') with at least one polyol (ii); (2) contacting the polymer obtained in (1.2) or (1.2') with a filler (iv) as defined in the present invention; Includes.

[0088] Preferably, (1) is carried out at a temperature in the range of 0 to 200°C, more preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0089] Preferably, one or more of (1) and (2), more preferably (1) and (2), are carried out in the absence of a solvent.

[0090] Preferably, the step of contacting the polymer and filler in (2) is carried out by mixing or pressing.

[0091] In the context of the present invention, it is also conceivable to use other thermomechanical methods for step (2), such as injection molding, casting, etc.

[0092] Preferably, the pressing is carried out at a pressure in the range of 440 kPa to 1320 kPa (preferably measured as a pressure of 10 to 30 kN when pressed with a 17 cm diameter circular press), more preferably at a pressure in the range of 660 kPa to 1100 kPa (preferably measured as a pressure of 15 to 25 kN when pressed with a 17 cm diameter circular press), and more preferably at a pressure in the range of 792 kPa to 968 kPa (preferably measured as a pressure of 18 to 22 kN when pressed with a 17 cm diameter circular press).

[0093] Preferably, the pressing is hot pressing, and is carried out at a temperature in the range of 100 to 200°C, more preferably in the range of 120 to 160°C, more preferably in the range of 130 to 150°C.

[0094] Preferably, pressing is carried out for a duration in the range of 1 to 60 minutes, more preferably in the range of 4 to 20 minutes, more preferably in the range of 5 to 10 minutes.

[0095] Preferably, the method comprises: (1.3) curing the polymer obtained in (1.2) or (1.2') at a temperature preferably in the range of 90 to 150°C, more preferably in the range of 100 to 120°C; or (3) curing the polymer obtained in (2) at a temperature preferably in the range of 90 to 150°C, more preferably in the range of 100 to 120°C; Further includes:

[0096] The present invention further relates to the use of a poly(urea-urethane) polymer according to the invention or a poly(urea-urethane) polymer composite according to the invention as a recyclable material.

[0097] The present invention further relates to recyclable articles comprising a poly(urea-urethane) polymer according to the invention or a poly(urea-urethane) polymer composite according to the invention.

[0098] The present invention further relates to a method for molding a poly(urea-urethane) polymer or a poly(urea-urethane) polymer according to the invention, obtainable or obtained by a method according to the invention, which method comprises the steps of: forming a poly(urea-urethane) polymer, the forming of the polymer comprising: (x) subjecting a poly(urea-urethane) polymer to pressure and heat to obtain a shaped body, more preferably a foil or sheet; or (x') extruding the poly(urea-urethane) polymer to obtain a molded body, more preferably a granule or a paste. The present invention relates to a method, comprising:

[0099] Preferably, the applied pressure according to (x) is 10 3 ~10 7 Pa range, more preferably 1.5 x 10 3 ~10 6 The range is Pa.

[0100] Preferably, the heating in (x) is carried out in the range of 60 to 250°C, more preferably in the range of 65 to 150°C, more preferably in the range of 70 to 130°C.

[0101] Preferably, the extrusion according to (x') is carried out at a temperature in the range of 140 to 220°C, more preferably in the range of 160 to 200°C, more preferably in the range of 170 to 190°C.

[0102] Preferably, the poly(urea-urethane) polymer is extruded at a torque in the range of 2.0 to 2.4 kNm, more preferably at a maximum torque of 2.2 kNm.

[0103] The present invention is further described by the following set of embodiments, as well as combinations of embodiments resulting from the indicated dependencies and backward references. It should be noted that whenever a range of embodiments is mentioned, particularly in connection with a term such as "the poly(urea-urethane) polymer of any one of embodiments 1 to 4," it means that all embodiments within this range are expressly disclosed to those skilled in the art; that is, the wording of this term should be understood by those skilled in the art to be synonymous with "the poly(urea-urethane) polymer of any one of embodiments 1, 2, 3, and 4." Furthermore, it should be explicitly noted that the following set of embodiments represents a well-structured portion of the general description directed to preferred aspects of the present invention, and therefore properly supports, but does not represent, the scope of the claims of the present invention.

[0104] 1. A poly(urea-urethane) polymer comprising: The following ingredients (i) at least one isocyanate; (ii) at least one polyol; and (iii) at least one secondary amine having the following formula (I): 1. A poly(urea-urethane) polymer obtained or obtained by a process comprising the step of reacting: [ka] (In the formula, -R a - is -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 -Z1-; -Z1- is a substituted or unsubstituted straight or branched chain C1-C 30 is alkylene; -Z2- is a substituted or unsubstituted straight or branched chain 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted straight or branched chain C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 is cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 is cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 to C 30 is arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z11 - is C6-C substituted with -NHR or -OR 30 arylene, where R is H and substituted or unsubstituted straight or branched chain C1-C 10 selected from the group consisting of alkyl; -Z 12 - is -N(R f )-and; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z 13 At least one of the one or more heteroatoms in a Derived from; C a is a C atom or H atom, and C b is a C atom or H atom, and C a and C b at least one of which is a C atom; X a is an O atom or NH, and X b is an O atom or NH, and X a and X b At least one of X is NH, a and / or X b When is NH, each C a and / or C b is a C atom; where: (A)R c , R d , R f and R g are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl; R b and R e are independent of each other and R c , R d , R f and R g defined as; or R b and R e does not exist, and C a and C b are bonded to each other through a single bond, and C a , C b , X a , X b and R a or forming a heterocyclic ring consisting of (B)C a and R e is a substituted or unsubstituted C6-C 30 forming an arylene, preferably phenyl, R f and R g does not exist; and C b and R b is a substituted or unsubstituted C6-C 30 forming an arylene, preferably phenyl, R c and Rd does not exist; or (C)- C a and R e is a substituted or unsubstituted C6-C 30 Forming an arylene, R f and R g does not exist; or - C b and R b is a substituted or unsubstituted C6-C 30 Forming an arylene, R c and R d None of the are present; where C a and R e Substituted or unsubstituted C6-C 30 When forming an arylene, R b , R c and R d are independent of each other under (A) R c , R d , R f and R g is defined as any one of the following: where C b and R b Substituted or unsubstituted C6-C 30 When forming an arylene, R e , R f and R g are independent of each other under (A) R c , R d , R f and R g (defined as one of the following:

[0105] 2.X a is NH and X b is NH, and the secondary amine (iii) is represented by the following formula (II): [ka] (In the formula, C a , C b , R b , R c , R d , R e, R f , R g , and -R a - is as defined in formula (I) 2. The poly(urea-urethane) polymer of embodiment 1, having

[0106] 3.-R a -, -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z9-Z1-Z9-, -Z1-Z5-Z1-, -Z1-Z9-Z1-, and -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), preferably -Z2-, -Z9-Z1-Z9-, and -Z9-Z1 (-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), more preferably -Z2- and -Z9-Z1 (-Z 11 -Z1) n 3. The poly(urea-urethane) polymer of embodiment 1 or 2, selected from the group consisting of -Z9-, where n=1, 2, 3, 4, 5, or 6.

[0107] 4. -Z1- is -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH2-CH(CH2CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, - CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, and -(CH2) 10 4. The poly(urea-urethane) polymer of any one of embodiments 1 to 3, selected from the group consisting of:

[0108] 5. The poly(urea-urethane) polymer of any one of embodiments 1 to 4, wherein -Z9- is selected from the group consisting of phenylene, naphthylene, biphenylene, fluorenylene, and indenyl, and -Z9- is preferably phenylene.

[0109] 6.-R a The poly(urea-urethane) polymer of embodiment 5, wherein - is -Z9-Z1-Z9-, -Z9- is phenylene, preferably para-phenylene, and -Z1- is -CH2-.

[0110] 7.-R a -, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), -Z9- is phenylene, -Z1- is -CH2-, and -Z 11 The poly(urea-urethane) polymer of embodiment 5, wherein - is a C-arylene substituted with -NHR.

[0111] 8. The poly(urea-urethane) polymer of any one of embodiments 1 to 5, wherein -Z2- is a substituted or unsubstituted linear or branched chain 2- to 500-membered heteroalkylene, preferably a substituted or unsubstituted linear or branched chain 2- to 35-membered heteroalkylene, more preferably a substituted or unsubstituted linear or branched chain 2- to 30-membered heteroalkylene.

[0112] 9. -Z2- is -CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-CH2-N(CH3)-CH 2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH 2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O- CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, [CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(where R x1 is -CH2-CH3, and R y1 is [-O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ) and m1+n1+o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C(R l )(R m )(R n ) and m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3-[CH2-CH(CH3)-O] o3 -CH2-CH(CH)3- (where n3 is in the range of 8-10, and m3 + o3 is in the range of 3-4, or n3 is in the range of 12-13 and m3+o3 is in the range of 5-7, or n3 is in the range of 38-40, and m3+o3 is in the range of 5-7). -[CH-CH2-O] m4 -CH2-CH2- (where m4 ranges from 8 to 250), and -[CH2-CH2-NH] m5 - (wherein m5 is in the range of 10 to 100,000), -Z2- is preferably -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -, where R x1 is -CH2-CH3, and R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n 9. The poly(urea-urethane) polymer of embodiment 8, wherein m1+n1+o1 ranges from 5 to 6.

[0113] 10.R c , R d , R f and R g are, independently of one another, hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl, and —C(OH)HR kis selected from the group consisting of, preferably selected from the group consisting of hydrogen, methyl, and ethyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl; where R k is hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 10. The poly(urea-urethane) polymer of any one of embodiments 1 to 9, wherein the urea-urethane polymer is selected from the group consisting of alkylene 5- to 30-membered heteroaryl.

[0114] 11.R b and R eare each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of hydrogen, methyl, and ethyl.

[0115] 12.R b , R c , and R d is H, and R e , R f , and R g is H; R b , R c , and R d One of the groups other than H is CH3, and R e , R f , and R g 12. The poly(urea-urethane) polymer of any one of the preceding embodiments, wherein one other than H is CH.

[0116] 13.R b , R c , and R d is an ethyl group, and R e , R f , and R g is an ethyl group; Preferably, R b , R c , and R d Of these, one is H except for the ethyl group, R e , R f , and R gOf these, one is H except for the ethyl group, R b , R c , and R d Of these, one other than the ethyl group or H is CH3, R e , R f , and R g 13. The poly(urea-urethane) polymer of any one of embodiments 1 to 12, wherein one other than an ethyl group or H is CH3.

[0117] 14. At least one secondary amine (iii) is 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA); or at least one secondary amine (iii) is DIB-butanediamine (N,N'-di-sec-butyl-1,4-butanediamine); Or the poly(urea-urethane) polymer of any one of embodiments 1 to 13, wherein at least one secondary amine (iii) is 2-(ethylamino)ethanol.

[0118] 15. At least one secondary amine (iii) is a sec-butyl-modified polyetheramine, CH3-CH2-CH(CH3)-NH-[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -NH-CH(CH3)-CH2-CH3 (wherein R x1 is -CH2-CH3, and R y1 is -CH2-[O-CH2-CH(CH3)] n1 14. The poly(urea-urethane) polymer of any one of embodiments 1 to 13, wherein m1+n1+o1 is in the range of 5 to 6.

[0119] 16. The poly(urea-urethane) polymer according to any one of the preceding embodiments, wherein at least one isocyanate (i) has an NCO functionality of 2 or greater, preferably 2 or 3; preferably, at least one isocyanate (i) is a mixture of an isocyanate with an NCO functionality of 2 and an isocyanate with an NCO functionality of 3 or greater, and preferably, at least one isocyanate (i) is a mixture of an isocyanate with an NCO functionality of 2 and an isocyanate with an NCO functionality of 3.

[0120] 17. At least one isocyanate (i) is selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), tolylene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanate benzene, xylene 2,6-diisocyanate, naphthylene 1,5-diisocyanate (1,5-NDI), butane 1,4-diisocyanate, and pentane 1,5-diisocyanate. (PDI), hexane 1,6-diisocyanate (HDI), octane 1,8-diisocyanate, nonane 1,9-diisocyanate, decane 1,10-diisocyanate, 2,2-dimethylpentane 1,5-diisocyanate, 2-methylpentane 1,5-diisocyanate (MPDI), 2,4,4 (or 2,2,4)-trimethylhexane 1,6-diisocyanate (TMDI), cyclohexane 1,3- and 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), methylene-bis(cyclohexyl isocyanate) (H12 mDI), 2,4- or 2,6-diisocyanato-1-methylcyclohexane (H6TDI), 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane (AMCI), 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane-4,4',4"-triisocyanate, toluene-2,4,6-triyl Triisocyanate, ethyl ester 1-lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, triisocyanatomethylcyclohexane, 1,8-diisocyanato-4-(isocyanatomethyl)octane, undecane 1,6,11-triisocyanate, 1,7-diisocyanato-4-(3-isocyanatopropyl)heptane, 1,6-diisocyanato-3-(isocyanatomethyl)hexane, 2,2-Bis[[4-(isocyanatomethyl)phenyl]methyl]butyl n-[[4-(isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)tris(hexamethylene)isocyanate, 1,3,5-triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3"-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyltris(isocyanatomethyl)phenyl]methyl] (methylene)]tris[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanato-dicyclohexylmethane, triisocyanatotriphenylthiophosphate, 2,4,4'-diphenyl ether triisocyanate, 1,3-bis(3-isocyanato-4-methylphenyl)-1,3-diazetidine-2,4-dione, and mixtures of two or more thereof; 17. The poly(urea-urethane) polymer of any one of embodiments 1 to 16, preferably selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), tolylene diisocyanate (TDI), naphthylene 1,5-diisocyanate (1,5-NDI), 1,4-diisocyanate, pentane 1,5-diisocyanate (PDI), hexane 1,6-diisocyanate (HDI), methylene-bis(cyclohexyl isocyanate) (H12 mDI), and a mixture of two or more thereof.

[0121] 18. The poly(urea-urethane) polymer according to embodiment 17, wherein the at least one isocyanate (i) is selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and tolylene diisocyanate (TDI).

[0122] 19. The poly(urea-urethane) polymer of any one of embodiments 1 to 18, wherein the at least one polyol (i) is selected from the group consisting of polyester polyols, polyetherester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols, and mixtures thereof.

[0123] 20. The poly(urea-urethane) polymer according to embodiment 19, wherein the at least one polyol (i) is selected from the group consisting of polyester polyols and polyether polyols.

[0124] 21. The poly(urea-urethane) polymer according to embodiment 20, wherein the at least one polyol (ii) is a polyether polyol, which is preferably selected from the group consisting of polytetrahydrofuran, trifunctional polyether polyols containing secondary hydroxyl groups, polypropylene glycol, polyether polyols based on sucrose, tetrafunctional polyether polyols based on ethylene diamine and propylene oxide, and mixtures of two or more thereof, more preferably selected from the group consisting of polytetrahydrofuran and trifunctional polyether polyols containing secondary hydroxyl groups.

[0125] 22. The poly(urea-urethane) polymer of any one of embodiments 1 to 21, wherein the at least one isocyanate (i), the at least one polyol (ii), and the at least one secondary amine (iii) are reacted in the absence of a solvent.

[0126] 23. The poly(urea-urethane) polymer of any one of embodiments 1 to 22, wherein the polymer is obtained or has been obtained by a process comprising reacting (i), (ii), and / or (iii), preferably (i) and (ii), with at least one additive, wherein the at least one additive is selected from the group consisting of benzoyl chloride and diethylene glycol bischloroformate.

[0127] 24. The poly(urea-urethane) polymer of any one of embodiments 1 to 23, wherein the polymer is obtained or was obtained by a process in the absence of a catalyst.

[0128] 25. The poly(urea-urethane) polymer of any one of embodiments 1 to 24, - reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; and - reacting the resulting prepolymer with at least one secondary amine (iii). or obtained by a process comprising: - reacting at least one isocyanate (i) with at least one secondary amine (iii) to obtain a prepolymer; and - reacting the resulting prepolymer with at least one polyol (ii). 25. The poly(urea-urethane) polymer of any one of embodiments 1 to 24, obtained or obtained by a process comprising:

[0129] 26. The poly(urea-urethane) polymer of any one of embodiments 1 to 25, wherein the molar ratio of —NCO of the at least one isocyanate (i) to —OH of the at least one polyol (ii) is in the range of 1:0.50 to 1:0.10, preferably in the range of 1:0.40 to 1:0.15, and more preferably in the range of 1:0.30 to 1:0.20.

[0130] 27. The poly(urea-urethane) polymer of any one of embodiments 1 to 26, wherein the molar ratio of —NCO of the at least one isocyanate (i) to —NH of the at least one secondary amine (iii) is in the range of 1:1.50 to 1:0.5, preferably in the range of 1:1.20 to 1:0.60, and more preferably in the range of 1:0.8 to 1:0.7.

[0131] 28. The poly(urea-urethane) polymer of any one of embodiments 1 to 27, wherein the reaction of components (i), (ii) and / or (iii) is conducted at a temperature in the range of greater than 0 to 200°C, preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0132] 29. The poly(urea-urethane) polymer of any one of embodiments 1-27, obtained or obtainable by a process further comprising curing the mixture of (i), (ii), and (iii) preferably at a temperature in the range of 90-200°C, more preferably at a temperature in the range of 100-150°C.

[0133] 30. The poly(urea-urethane) polymer of any one of embodiments 1-29, which is thermoplastic or thermoset.

[0134] 31. The poly(urea-urethane) polymer of any one of embodiments 1 to 30, having a solubility in toluene ranging from 0.05:1 to 1:1 g / mL (grams of dissolved polymer:mL of solvent) measured after heating at a temperature of 110° C. and ambient pressure for at least 12 hours, preferably having a solubility in toluene ranging from 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer:mL of solvent) measured after heating at a temperature of 110° C. and ambient pressure for at least 12 hours.

[0135] 32. The poly(urea-urethane) polymer of any one of embodiments 1 to 31, having a solubility in 1,3-dimethyl-2-imidazolidinone in the range of 0.05:1 to 1:1 g / mL (grams of polymer dissolved:mL of solvent) measured after heating at a temperature of 130° C. and ambient pressure for at least 20 hours, and preferably in organic solvents in the range of 0.075:1 to 0.5:1 g / mL (grams of polymer dissolved:mL of solvent) measured after heating at a temperature of 130° C. and ambient pressure for at least 20 hours.

[0136] 33. The poly(urea-urethane) polymer of any one of embodiments 1 to 32, having a melting point in the range of 10°C to 200°C at a pressure of 880 kPa, as determined by hot pressing (preferably using a 17 cm diameter circular press and 20 kN applied pressure), more preferably in the range of 50°C to 190°C at a pressure of 880 kPa, as determined by hot pressing (preferably using a 17 cm diameter circular press and 20 kN applied pressure), and more preferably in the range of 60°C to 180°C at a pressure of 880 kPa, as determined by hot pressing (preferably using a 17 cm diameter circular press and 20 kN applied pressure).

[0137] 34. A poly(urea-urethane) polymer-based composite material, comprising: The following ingredients (i) at least one isocyanate; (ii) at least one polyol; and (iii) at least one secondary amine having the following formula (I): to obtain a mixture comprising a poly(urea-urethane) polymer, more preferably the poly(urea-urethane) polymer of any one of embodiments 1 to 33; - reacting the resulting mixture with component (iv): (iv) contacting the material with a filler selected from the group consisting of glass fiber, carbon fiber, mineral fiber, fabric, metal mesh, metal fiber, metal rod, carbonate, wood, and mixtures of two or more thereof; 1. A poly(urea-urethane) polymer-based composite material obtained or obtained by a process comprising: [ka] (In the formula, -R a - is -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (n=1, 2, 3, 4, 5, or 6), and -Z1-Z 12 -Z1-; -Z1- is a substituted or unsubstituted straight or branched chain C1-C 30 is alkylene; -Z2- is a substituted or unsubstituted straight or branched chain 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted straight or branched chain C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 is cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 is cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 to C 30 is arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z 11 - is C6-C substituted with -NHR or -OR 30 arylene, where R is H and substituted or unsubstituted straight or branched chain C1-C 10 selected from the group consisting of alkyl; -Z 12 - is -N(R f )-and; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z 13 At least one of the one or more heteroatoms in a Derived from; C a is a C atom or H atom, and C b is a C atom or H atom, and C a and C b at least one of which is a C atom; X a is an O atom or NH, and X b is an O atom or NH, and X a and X b At least one of X is NH, a and / or X b When is NH, each C a and / or Cb is a C atom; where: (A)R c , R d , R f and R g are each independently hydrogen, straight or branched chain substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl; R b and R e are independent of each other and R c , R d , R f and R g defined as; or R b and R e does not exist, and C a and C b are bonded to each other through a single bond, and C a, C b , X a , X b and R a or forming a heterocyclic ring consisting of (B)C a and R e is a substituted or unsubstituted C6-C 30 forming an arylene, preferably phenyl, R f and R g does not exist; and C b and R b is a substituted or unsubstituted C6-C 30 forming an arylene, preferably phenyl, R c and R d does not exist; or (C)-C a and R e is a substituted or unsubstituted C6-C 30 Forming an arylene, R f and R g does not exist; or -C b and R b is a substituted or unsubstituted C6-C 30 Forming an arylene, R c and R d None of the are present; where C a and R e Substituted or unsubstituted C6-C 30 When forming an arylene, R b , R c and R d are independent of each other under (A) R c , R d , R f and R g is defined as any one of the following: where C b and R b Substituted or unsubstituted C6-C 30 When forming an arylene, R e , R f and R g are independent of each other under (A) R c , Rd , R f and R g (defined as one of the following:

[0138] 35. The composite material of embodiment 34, wherein the filler (iv) is a glass fiber.

[0139] 36. A method for preparing a poly(urea-urethane) polymer according to any one of embodiments 1 to 33, comprising: (a) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; (b) contacting the prepolymer obtained in (a) with at least one secondary amine, wherein the at least one secondary amine has formula (I) as described in any one of embodiments 1 to 15, to obtain a poly(urea-urethane) polymer; or (a') reacting at least one isocyanate (i) with at least one secondary amine, wherein the at least one secondary amine has formula (I) as described in any one of embodiments 1 to 15, to obtain a prepolymer; (b') contacting the prepolymer obtained in (a') with at least one polyol (ii) to obtain said poly(urea-urethane) polymer. A method comprising:

[0140] 37. The method of embodiment 36, wherein (a) or (a') is carried out at a temperature in the range of 0 to 200°C, preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0141] 38. The method of embodiment 36 or 37, wherein one or more of (a) and (b) or one or more of (a') and (b'), preferably (a) and (b) or (a') and (b'), is carried out in the absence of a solvent.

[0142] 39. The method of any one of embodiments 36 to 38, wherein (b) or (b') is carried out at a temperature in the range of 0 to 200°C, preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0143] 40. (c) Curing the mixture obtained in (b) or (b') at a temperature preferably in the range of 90 to 150°C, more preferably in the range of 100 to 120°C. 40. The method of any one of embodiments 36 to 39, further comprising:

[0144] 41. A method for preparing a composite material according to embodiment 34 or 35, comprising: (1) providing a poly(mochevinoi) polymer; (1.1) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; (1.2) contacting the prepolymer obtained in (1.1) with at least one secondary amine, wherein the at least one secondary amine (iii) has formula (I) as defined in any one of embodiments 1 to 15; or (1.1') reacting at least one isocyanate (i) with at least one secondary amine (wherein the at least one secondary amine (iii) has formula (I) as defined in any one of embodiments 1 to 15) to obtain a prepolymer; (1.2') contacting the prepolymer obtained in (1.1') with at least one polyol (ii); (2) contacting the polymer obtained in (1.2) or (1.2') with a filler as defined in embodiment 31 or 32; A method comprising:

[0145] 42. The method of embodiment 41, wherein (1) is carried out at a temperature in the range of 0 to 200°C, preferably in the range of 1 to 200°C, more preferably in the range of 10 to 150°C, more preferably in the range of 20 to 90°C.

[0146] 43. The method of embodiment 41 or 42, wherein one or more of (1) and (2), more preferably (1) and (2), is carried out in the absence of a solvent.

[0147] 44. The method of any one of embodiments 41-43, wherein the step of contacting the polymer and filler in (2) is carried out by mixing or pressing.

[0148] 45. The method of embodiment 44, wherein the pressing is performed at a pressure in the range of 440 kPa to 1320 kPa (preferably measured as a pressure of 10 to 30 kN in a 17 cm diameter circular press), more preferably at a pressure in the range of 660 kPa to 1100 kPa (preferably measured as a pressure of 15 to 25 kN in a 17 cm diameter circular press), and more preferably at a pressure in the range of 792 kPa to 968 kPa (preferably measured as a pressure of 18 to 22 kN in a 17 cm diameter circular press).

[0149] 46. ​​(1.3) Curing the polymer obtained in (1.2) or (1.2') at a temperature preferably in the range of 90 to 150°C, more preferably in the range of 100 to 120°C; or (3) Curing the polymer obtained in (2) at a temperature preferably in the range of 90 to 150°C, more preferably in the range of 100 to 120°C. 45. The method of any one of embodiments 41 to 44, further comprising:

[0150] 47. Use of the poly(urea-urethane) polymer of any one of embodiments 1 to 33 or the poly(urea-urethane) polymer composite of embodiment 34 or 35 as a recyclable material.

[0151] 48. A recyclable article comprising the poly(urea-urethane) polymer of any one of embodiments 1 to 33 or the poly(urea-urethane) polymer composite of embodiment 34 or 35.

[0152] 49. A method for shaping a poly(urea-urethane) polymer according to any one of embodiments 1 to 33, or a poly(urea-urethane) polymer obtained or obtained by the method according to any one of embodiments 36 to 40, comprising: shaping a poly(urea-urethane) polymer, the step of shaping the polymer comprising: (x) subjecting a poly(urea-urethane) polymer to pressure and heat to obtain a shaped body, more preferably a foil or sheet; or (x') extruding the poly(urea-urethane) polymer to obtain a molded body, more preferably a granule or a paste. Including steps A method comprising:

[0153] 50.(x) The applied pressure is 10 3 ~10 7 Pa range, preferably 1.5 x 10 3 ~10 6 50. The method of embodiment 49, wherein the temperature is in the range of Pa.

[0154] 51. The method of embodiment 49 or 50, wherein the heating in (x) is carried out at a temperature in the range of 60°C to 250°C, preferably in the range of 65 to 150°C, more preferably in the range of 70 to 130°C.

[0155] 52. The method of any one of embodiments 49 to 51, wherein the extrusion according to (x') is carried out at a temperature in the range of 140 to 220°C, preferably in the range of 160 to 200°C, more preferably in the range of 170 to 190°C. [Brief explanation of the drawings]

[0156] [Figure 1] 1 shows the different steps for testing the recycling properties of the plates obtained in Comparative Example 1A and Example 1A: 1. chopping / cutting; 2. adding toluene; 3. heating for 16 hours followed by cooling; 4. removing toluene. [Figure 2]1 shows the results of compression molding at different temperatures for Example 1A and Comparative Example 1A. The arrows indicate that for the Comparative Example, only small pieces were obtained at 80°C and 100°C, indicating that no melting occurred at these temperatures, while the material of Example 1A already yielded a foil at 80°C. [Figure 3] Figure 1 illustrates the different steps for testing the recycling properties of the plates obtained in Comparative Example 2 and Example 2: 1. Shredding / cutting; 2. Addition of toluene; heating for 16 hours followed by cooling. [Figure 4] 1 is a diagram showing test results after compression molding at different temperatures for Example 2 and Comparative Example 2. Comparative Example 2 does not melt at all up to a temperature of 180°C, whereas Example 2 melts at around 130°C. [Figure 5] Figure 1 shows the various steps involved in testing the recyclability of the composite material of Example 4. 1. Toluene was added to a small piece of the composite of Example 4 and heated to reflux for 16 hours. 2. Hot filtration: a: separated glass fibers, b: the filtrate was gelled and dried; 3. Pressing b at 140°C and 880 kPa for 5 minutes (20 kN force in a 17 cm diameter circular press according to the melting point analysis method described above) to obtain a thin foil; 4. Recycled composite material containing glass fibers obtained by sandwiching the glass fibers between two foils and pressing them. DETAILED DESCRIPTION OF THE INVENTION

[0157] In the context of the present invention, the term "alkylene" refers to a C1-C2 alkylene having 1 to 30 (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30) C atoms. 30It relates to acyclic saturated hydrocarbon groups which may be acyclic saturated hydrocarbon chains combining different moieties, as in alkylene, or as in C1-C5 alkylene having 1 to 5 (i.e., 1, 2, 3, 4, or 5) C atoms. Representative examples of alkylene include, but are not limited to, -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH(CH2CH3)-, -CH2-CH2-CH(CH2CH3)-, -CH2-CH(n-C3H7)-, -CH2-CH(n-C4H9)-, -CH2-CH(n-C5H 11 )-, -CH2-CH(n-CH 13 )-, -CH2-CH(n-CH 15 )-, -CH2-CH(n-CH 17 )-, -CH(CH3)-CH(CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-[C(CH3)2]2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2 -CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, -(CH2) 10 -, -(CH2)7-, -(CH2)9-, -(CH2) 11 -, -(CH2) 12 -, -(CH2) 13 -, -(CH2) 14 -, -(CH2) 15 -, -(CH2) 16 -, -(CH2) 17 -, -(CH2) 18 -, -(CH2) 19 -, -(CH2) 20 -, -(CH2) 21 -, -(CH2) 22 -, -(CH2) 23 -, -(CH2) 24 -, -(CH2) 25 -, -(CH2) 26 -, -(CH2) 27 -, -(CH2) 28 -, -(CH2) 29- and -(CH2) 30 - are some examples.

[0158] In the context of the present invention, the term "heteroalkylene" refers to the above alkylene group in which one or more carbon atoms are replaced by heteroatoms independently selected from the group consisting of oxygen, sulfur, and nitrogen (-NH-). The heteroalkylene group may have one, two, or three heteroatoms, particularly preferably one heteroatom, selected from the group consisting of oxygen, sulfur, and nitrogen (-NH-), as one or more chain bonds. The heteroalkylene group may preferably have 2 to 30 members, particularly preferably 2 to 12 members, and very particularly preferably 2 or 6 members. More preferably, oxygen (-O-) is the most preferred heteroatom in "heteroalkylene". Representative examples of heteroalkylene groups include, but are not limited to, (-CH2-O-CH2-). 1-500 , (-CH2-O-CH(CH3)-) 1-500 , -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-O-CH(CH3)-, -CH2-O-CH(CH2CH3)-, -CH2-O-CH(n-C3H7)-, -CH2-O-CH(n-C4H9)-, -CH2-O-CH(n-C5H 11 )-, -CH2-O-CH(n-CH 13 )-, -CH2-O-CH(n-CH 15 )-, -CH2-O-CH(n-CH 17 )-, -CHO-(CH3)-CHO-(CH3)-, -CO-(CH3)2-, -CH2-OC(CH3)2-CH2-, -CH2-[OC(CH3)2]2-CH2-, - (CH2)3-O-CH2-, -(CH2)4-O-CH2-, -(CH2)5-O-CH2-, -(CH2)6-O-CH2-, -(CH2)8-OCH2-, -(CH2) 10 -O-CH2-, -(CH2)7-O-CH2-, -(CH2)9-O-CH2-, -(CH2) 11 -O-CH2-, -(CH2) 12 -O-CH2-, -(CH2) 13-O-CH2-,-(CH2) 14 -O-CH2-,-(CH2) 15 -O-CH2-,-(CH2) 16 -O-CH2-,-(CH2) 17 -O-CH2-,-(CH2) 18 -O-CH2-,-(CH2) 19 -O-CH2-,-(CH2) 20 -O-CH2-,-(CH2) 21 -OCH2-,-(CH2) 22 -OCH2-,-(CH2) 23 -O-CH2-,-(CH2) 24 -OCH2-,-(CH2) 25 -OCH2-,-(CH2) 26 -OCH2-,-(CH2) 27 -O-CH2-,-(CH2) 28 -O-CH2-,-(CH2) 29 -O-CH2-,-(CH2) 30 -O-CH2-、-CH2-S-CH2-、-CH2-NH-CH2-、-CH2-NH-、-CH2-CH2-NH-CH2-CH2-CH2-、-CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-、-CH2 -CH2-CH2-NH-CH2-CH2-CH2-、-CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-、-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-、-CH2-CH2 -NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-、-CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-、-CH2-CH2-CH2-O-CH2-CH 2-CH2-CH2-O-CH2-CH2-CH2-、-CH2-CH2-O-CH2-CH2-O-CH2-CH2-、-CH(CH3)-CH2-NH-CH2-CH(CH3)-、-CH2-CH2-NH-CH2-CH2-、 -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(here, R x1is -CH2-CH3, and R y1 is [-O-CH2-CH(CH3)] n1 -NH-C d (R l )(R m )(R n ) and m1+n1+o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C d (R l )(R m )(R n ) and m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O] o3 -CH2-CH(CH)3- (where n3 is in the range of 8-10, and m3 + o3 is in the range of 3-4, or n3 is in the range of 12-13 and m3+o3 is in the range of 5-7, or n3 is in the range of 38-40, and m3+o3 is in the range of 5-7). -[CH-CH2-O] m4 -CH2-CH2- (where m4 ranges from 8 to 250), and -[CH2-CH2-NH] m5 - (where m5 is in the range of 10 to 100,000).

[0159] In the context of the present invention, the term "alkenylene" relates to an acyclic unsaturated hydrocarbon group having at least one double bond, preferably 1, 2 or 3 double bonds, which may be branched or linear, unsubstituted or may have a C2-C 30As in the case of alkenylene, it may be at least monosubstituted with 2 to 30 (i.e., 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30) C atoms, more preferably C 20 Alkenylene, most preferably C2-C 10 Alkenylene, particularly C2-C6 alkenylene. Representative examples of alkenylene include, but are not limited to, -CH=CH- and -CH2-CH=CH-.

[0160] In the context of the present invention, the term "heteroalkenylene" refers to an alkenylene group as defined above, in which one or more carbon atoms are replaced by heteroatoms independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH). Heteroalkenylene groups may have one, two, or three heteroatoms, particularly preferably one heteroatom, selected from the group consisting of oxygen, sulfur, and nitrogen (NH), as one or more tethered bonds. Heteroalkenylene groups may preferably have 3 to 30 members, particularly preferably 3 to 12 members, and very particularly preferably 3 or 6 members. Representative examples of heteroalkenylene groups include, but are not limited to, -CH=CH-NH-, -CH=CH-O-, -CH=CH-CH2-O-, and -CH=CH-S-.

[0161] In the context of the present invention, if one or more of the substituents denotes or contains an alkylene, alkenylene, heteroalkylene and heteroalkenylene group, which is mono- or polysubstituted, this group is preferably selected from the group consisting of phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C 1~5 -alkyl)2, -NH-phenyl, -N(C 1~5 -alkyl)(phenyl), -N(C 1~5 -alkyl)(CH2-phenyl), -N(C 1~5-alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1~5 -Alkyl, -C(=O)-phenyl, -C(=S)-C 1~5 -Alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-OC 1~5 -Alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1~5 -Alkyl, -C(=O)-N(C 1~5 -alkyl)2, -S(=O)-C 1~5 -Alkyl, -S(=O)-phenyl, -S(=O)2-C 1~5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, preferably 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3, substituents selected independently from one another from the group consisting of -C 1~5 The alkyl residues are in each case linear or branched, and the abovementioned phenyl residues are unsubstituted or substituted with F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1~5 Alkyl, -(CH2)-OC 1~5 -Alkyl, -C 2~5 Alkenyl, -C 2~5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1~5 -Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1~5-substituted by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, substituents independently selected from the group consisting 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. Alkylene, alkenylene, heteroalkylene and heteroalkenylene groups are understood to be, independently of one another, unsubstituted or substituted with one, two or three substituents selected independently of one another from the group consisting of phenyl, F, Cl, Br, I, -NO, -CN, -O-phenyl, -SH, -S-phenyl, -NH, -N(CH), -N(CH) and -N(CH)(CH), where the phenyl residue is unsubstituted or substituted with one, two, three, four or five substituents selected independently of one another from the group consisting of F, Cl, Br, I, -OH, -SH, -NO, -CN, -O-CH, -O-CF and -O-CH.

[0162] In the context of the present invention, the term "cycloalkylene" relates to a saturated cyclic hydrocarbon group. 30 Representative examples of cycloalkylene groups include, but are not limited to, cyclopentylene groups (e.g., cyclopent-1,3-ylene, cyclopent-1,2-ylene), cyclohexylene groups (e.g., cyclohex-1,4-ylene, cyclohex-1,3-ylene, and cyclohex-1,2-ylene), cycloheptylene groups, cyclooctylene groups (e.g., 1,5-cyclooctylene), [ka] Examples include:

[0163] In the context of the present invention, the term "cycloalkylene" also relates to bridged cyclic hydrocarbon groups, for example, cyclic hydrocarbon groups having 2 to 4 rings with 5 to 30 carbon atoms. Representative examples include, but are not limited to, norbornylene groups (e.g., 1,4-norbornylene and 2,5-norbornylene), norbornyl groups (e.g., 2,6-norbornyl), and adamantylene groups (e.g., 1,5-adamantylene and 2,6-adamantylene).

[0164] In the context of the present invention, the term "heterocycloalkylene" also relates to cyclic or polycyclic saturated divalent radicals having 5 to 30 ring members, the carbon atoms of which are replaced by 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S. Representative examples include, but are not limited to, 1,5-dioxaoctylene, 4,8-dioxabicyclo[3.3.0]octylene.

[0165] In the context of this invention, the term "cycloalkenylene" relates to a divalent cycloalkenyl ring system, i.e., a cycloalkenyl as defined herein having two single bonds as points of attachment to other groups. Representative examples of "cycloalkenylene" include, but are not limited to, cyclopent-1,2-en-3,5-ylene, 3-cyclohexen-1,2-ylene, 2,5-cyclohexadien-1,4-ylene, cyclohex-1,2-en-3,5-ylene, 2,5-cyclohexadien-1,4-ylene, and cyclohept-1,2-en-3,5-ylene.

[0166] In the context of the present invention, the term "heterocycloalkenylene" relates to a cyclic or polycyclic non-aromatic unsaturated divalent radical having 5 to 30 carbon atoms, the carbon atoms of which are substituted by 1, 2 or 3 heteroatoms selected from N, O and S heteroatoms, and having 1, 2 or 3 double bonds.

[0167] In the context of the present invention, when one or more substituents denote mono- or polysubstituted cycloalkylene, cycloalkenylene, heterocycloalkylene and heterocycloalkenylene, this group is preferably selected from the group consisting of phenyl, F, Cl, Br, I, —NO, —CN, —O-phenyl, —O—CH-phenyl, —SH, —S-phenyl, —S—CH-phenyl, —NH, —N(C 1~5 -alkyl)2, -NH-phenyl, -N(C 1~5 -alkyl)(phenyl), -N(C 1~5 -alkyl)(CH2-phenyl), -N(C 1~5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1~5 -Alkyl, -C(=O)-phenyl, -C(=S)-C 1~5 -Alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-OC 1~5 -Alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1~5 -Alkyl, -C(=O)-N(C 1~5 -alkyl)2, -S(=O)-C 1~5 -Alkyl, -S(=O)-phenyl, -S(=O)2-C 1~5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, preferably 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3, substituents selected independently from one another from the group consisting of -C 1~5 The alkyl residues are in each case linear or branched, and the abovementioned phenyl residues are unsubstituted or substituted with F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1~5 Alkyl, -(CH2)-OC 1~5 -Alkyl, -C 2~5 Alkenyl, -C 2~5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1~5 -Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1~5-substituted by 1, 2, 3, 4 or 5, particularly preferably 1, 2, 3 or 4, substituents independently selected from the group consisting 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. Alkylene, alkenylene, heteroalkylene and heteroalkenylene groups are understood to be, independently of one another, unsubstituted or substituted with one, two or three substituents selected independently of one another from the group consisting of phenyl, F, Cl, Br, I, -NO, -CN, -O-phenyl, -SH, -S-phenyl, -NH, -N(CH), -N(CH) and -N(CH)(CH), where the phenyl residue is unsubstituted or substituted with one, two, three, four or five substituents selected independently of one another from the group consisting of F, Cl, Br, I, -SH, -NO, -CN, -O-CH, -O-CF and -O-CH.

[0168] In the context of this invention the term "arylene" designates a closed aromatic divalent ring or ring system, such as phenylene, naphthylene, biphenylene, fluorenylene, and indenyl.

[0169] In the context of this invention, the term "heteroarylene" designates a closed, aromatic, bivalent ring or ring system having at least one heteroatom selected from nitrogen, oxygen, and sulfur. Representative examples of heteroarylene groups include, but are not limited to, furylene, thienylene, pyridylene, quinolinylene, isoquinolinylene, indolylene, isoindolylene, triazolylene, pyrrolylene, tetrazolylene, imidazolylene, pyrazolylene, oxazolylene, thiazolylene, benzofuranylene, benzothiophenylene, carbazolylene, benzoxazolylene, pyrimidinylene, benzimidazolylene, quinoxalinylene, benzothiazolylene, naphthyridinylene, isoxazolylene, isothiazolylene, prinylene, quinazolinylene, pyrazinylene, 1-oxidopyridylene, pyridazinylene, triazinylene (preferably one or more of vic-triazinylene, asym-triazinylene, and sym-triazinylene), tetrazinylene, oxadiazolylene, and thiadiazolylene.

[0170] In the context of the present invention, if one or more of the substituents denotes mono- or polysubstituted arylene and heteroarylene, this is meant to include phenyl, F, Cl, Br, I, —NO 2 , —CN, —O-phenyl, —O—CH 2 -phenyl, —SH, —S-phenyl, —S—CH 2 -phenyl, —NH 2 , —N(C 1~5 -alkyl)2, -NH-phenyl, -N(C 1~5 -alkyl)(phenyl), -N(C 1~5 -alkyl)(CH2-phenyl), -N(C 1~5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1~5 -Alkyl, -C(=O)-phenyl, -C(=S)-C 1~5 -Alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-OC 1~5 -Alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1~5 -Alkyl, -C(=O)-N(C 1~5 -alkyl)2, -S(=O)-C 1~5-Alkyl, -S(=O)-phenyl, -S(=O)2-C 1~5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, preferably 1, 2, 3 or 4, particularly preferably 1, 2 or 3, substituents independently selected from the group consisting of -C 1~5 The alkyl residues are in each case linear or branched, and the abovementioned phenyl residues are unsubstituted or may be substituted with F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1~5 Alkyl, -(CH2)-OC 1~5 -Alkyl, -C 2~5 Alkenyl, -C 2~5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1~5 -Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1~5 -substituted by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, substituents independently selected from the group consisting 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. Alkylene, alkenylene, heteroalkylene and heteroalkenylene groups are understood to be, independently of one another, unsubstituted or substituted with one, two or three substituents selected independently of one another from the group consisting of phenyl, F, Cl, Br, I, -NO, -CN, -O-phenyl, -SH, -S-phenyl, -NH, -N(CH), -N(CH) and -N(CH)(CH), where the phenyl residue is unsubstituted or substituted with one, two, three, four or five substituents selected independently of one another from the group consisting of F, Cl, Br, I, -SH, -NO, -CN, -O-CH, -O-CF and -O-CH.

[0171] In the context of the present invention, the term "alkyl" encompasses acyclic saturated hydrocarbon residues, which may be branched or straight-chain, unsubstituted, and which have a C1-C 30 It may be at least monosubstituted by 1 to 30 (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30) C atoms, as in the case of alkyl, or by 1 to 5 (i.e., 1, 2, 3, 4, or 5) C atoms, as in the case of C1-C5 alkyl. In the context of the present invention, if one or more of the substituents denotes alkyl or contains mono- or polysubstituted alkyl, this may include F, Cl, Br, I, -OH, -NO2, -CN, -SH, -NH2, -N(C 1~5 -alkyl)2, -N(C 1~5 -alkyl)(phenyl), -N(C 1~5 -alkyl)(CH2-phenyl), -N(C 1~5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-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, preferably 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3, substituents independently selected from the group consisting of -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein the above C 1~5The alkyl residues are in each case linear or branched, and the phenyl residues are unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from the group consisting of F, Cl, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2H5, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, and tert-butyl. Particularly preferred substituents are independently selected from the group consisting of F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2, and -N(CH3)(C2H5).

[0172] In the context of the present invention, unsubstituted linear C1-C 30 Alkyl is preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl and tetracosyl; more preferably hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl and tetracosyl. It refers to an alkyl selected from the group consisting of benzoyl, benzophenone, benzoyl, benzoyl methyl ...

[0173] In the context of the present invention, unsubstituted branched chains C1-C30 Alkyl is preferably isopropyl, isobutyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, neo-pentyl, 2-methyl-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, 2,6-dimethyl-4-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso-hexadecyl, iso-octadecyl, iso-eicosyl, and 3-pinanyl-methyl. It refers to alkyl selected from the group consisting of: 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso-hexadecyl, iso-octadecyl, iso-eicosyl, 2-methyltricosyl, 2-ethyldocosyl, 3-ethylhexyl, 3-ethylhexyl, 4-propylhexyl, propylnonadecyl, 6-butyldodecyl and 5-ethylundecyl. In the context of the present invention, polysubstituted alkyl is understood to be polysubstituted, preferably di- or tri-substituted alkyl on different or the same C-atom, for example, tri-substituted on the same C-atom, as in -CF3, or tri-substituted at different positions, as in -(CHCl)-(CH2F). Polysubstitution can occur with the same or different substituents. Representative examples of substituents include, but are not limited to, -CH, -CF, -CFH, -CFH, -(CH)-OH, -(CH)-NH, -(CH)-CN, -(CH)-(CF), -(CH)-(CHF), -(CH)-(CHF), -(CH)-(CH)-O-CH, -(CH)-(CH)-NH, -(CH)-(CH)-CN, -(CF)-(CF), -(CH)-(CH)-(CF), and -(CH)-(CH)-(CH)-O-CH.

[0174] In the context of the present invention, substituted linear or branched C1-C 30 Alkyl also includes F, Cl, Br, I, -OH, 2-furanyl, -NO2, -CN, -SH, -NH2, -N(C 1~5 -alkyl)2, -N(C 1~5 -alkyl)(phenyl), -N(C 1~5 -alkyl)(CH2-phenyl), -N(C 1~5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1~5 -Alkyl, -C(=O)-phenyl, -C(=S)-C 1~5 -Alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-OC 1~5 -Alkyl, -C(=O)-)-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1~5 -Alkyl, -C(=O)-N(C 1~5 -alkyl)2, -S(=O)-C 1~5 -Alkyl, -S(=O)-phenyl, -S(=O)2-C 1~5 C1-C substituted with a functional group selected from the group consisting of -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H 30 It also refers to a branched or straight-chain saturated hydrocarbon group having carbon atoms, wherein the C1-5-alkyl residue is in each case straight-chain or branched, and the phenyl residue is preferably unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from the group consisting of F, Cl, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2H5, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, and tert-butyl. Particularly preferred substituents independently selected from the group consisting of F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2, and -N(CH3)(C2H5).

[0175] In the context of the present invention, substituted linear or branched C1-C30Alkyl can also be a functional group selected from the group consisting of hydroxy, alkoxy, C(=O)R, CN and SR, preferably 1-methoxymethyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methoxybutyl, 2-hydroxybutyl, 1-methoxypentyl, 1-methoxyhexyl, 1-methoxyheptyl, 1-methoxyoctyl, 1-methoxynonyl, decyl, 1-methoxyundecyl, 1-methoxydodecyl, 1-methoxytridecyl, 1-methoxytetradecyl, 1-methoxypentadecyl, 1-methoxyhexadecyl. , 1-methoxyheptadecyl, 1-methoxyoctadecyl, 1-methoxynonadecyl, 1-methoxyeicosyl, 1-methoxyheneicosyl, 1-methoxydocosyl, 1-methoxytricosyl, 1-methoxytetracosyl, 2-methoxypropyl, 2-methoxybutyl, 2-methoxypentyl, 2-methoxyhexyl, 2-methoxyheptyl, 2-methoxyoctyl, 2-methoxynonyl, decyl, 2-methoxyundecyl, 2-methoxydodecyl, 2-methoxytridecyl, 2-methoxytetradecyl, 2-methoxypentadecyl, 2-methoxyhexyl Decyl, 2-methoxyheptadecyl, 2-methoxyoctadecyl, 2-methoxynonadecyl, 2-methoxyeicosyl, 2-methoxyheneicosyl, 2-methoxydocosyl, 2-methoxytricosyl, 2-methoxytetracosyl, 1-acetoxymethyl, 1-acetoxyethyl, 1-acetoxypropyl, 1-acetoxybutyl, 1-acetoxypentyl, 1-acetoxyhexyl, 1-acetoxyheptyl, 1-acetoxyoctyl, 1-acetoxynonyl, decyl, 1-acetoxyundecyl, 1-acetoxydodecyl, 1-acetoxytridecyl, 1-acetoxytetradecyl, 1-acetoxypentadecyl, 1-acetoxyhexadecyl, 1-acetoxyheptadecyl, 1-acetoxyoctadecyl, 1-acetoxynonadecyl, 1-acetoxyeicosyl, 1-acetoxyheneicosyl, 1-acetoxydocosyl, 1-acetoxytricosyl, 1-acetoxytetracosyl, 1-cyanomethyl, 1-cyanoethyl, 1-cyanopropyl, 1-cyanobutyl, 1-cyanopentyl, 1-cyanohexyl, 1-cyanoheptyl, 1-cyanooctyl, 1-cyanononyl, decyl, 1-cyanoundecyl,1-cyanododecyl, 1-cyanotridecyl, 1-cyanotetradecyl, 1-cyanopentadecyl, 1-cyanohexadecyl, 1-cyanoheptadecyl, 1-cyanooctadecyl, 1-cyanononadecyl, 1-cyanoeicosyl, 1-cyanoheneicosyl, 1-cyanodocosyl, 1-cyanotricosyl, 1-cyanotetracosyl, 2-cyanopropyl, 2-cyanobutyl, 2- Cyanopentyl, 2-cyanohexyl, 2-cyanoheptyl, 2-cyanooctyl, 2-cyanononyl, decyl, 2-cyanoundecyl, 2-cyanododecyl, 2-cyanotridecyl, 2-cyanotetradecyl, 2-cyanopentadecyl, 2-cyanohexadecyl, 2-cyanoheptadecyl, 2-cyanooctadecyl, 2-cyanononadecyl, 2-cyanoeicosyl, 2-cyano C1 to C4 substituted with a functional group selected from the group consisting of heneicosyl, 2-cyanodocosyl, 2-cyanotricosyl, 2-cyanotetracosyl, 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-thioylpentadecyl, 1-thioylhexadecyl, 1-thioylheptadecyl, 1-thioyloctadecyl, 1-thioylnonadecyl, 1-thioyleicosyl, 1-thioylheneicosyl, 1-thioyldocosyl, 1-thioyltricosyl, and 1-thioyltetracosyl; 30 It also refers to a branched or straight chain saturated hydrocarbon group having carbon atoms.

[0176] In the context of the present invention, the term "alkenyl" refers to an unsubstituted straight-chain C-C 30Representative examples of alkenyl include, but are not limited to, 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, Examples include 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-eicosenyl, and 2-eicosenyl. More preferably, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-penta ... Examples include decenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-eicosenyl, and 2-eicosenyl, 20-heneicosenyl, 2-docosenyl, 6-tricosenyl, and 2-tetracosenyl.

[0177] Unsubstituted branched chain C2-C 30Representative examples of alkenyl include, but are not limited to, isopropenyl, isobutenyl, neopentenyl, 2-ethylhexenyl, 2-propylheptenyl, 2-butyloctenyl, 2-pentylnonenyl, 2-hexyldecenyl, isohexenyl, isoheptenyl, isooctenyl, isononenyl, isodecenyl, isododecenyl, isotetradecenyl, isohexadecenyl, isooctadecenyl, isoeicosenyl, 2-methyltricosenyl, 2-ethyldocosenyl, 3-ethylhenicosenyl, 3-ethylicosenyl, 4-propylhenicosenyl, 4-propylnonadecenyl, 6-butyldodecenyl, 5-ethylundecenyl, 1,4- Examples include hexadienyl, 1,3-hexadienyl, 2,5-hexadienyl, 3,5-hexadienyl, 2,4-hexadienyl, 1,3,5-hexatrienyl, 1,3,6-heptatrienyl, 1,4,7-octatrienyl, or 2-methyl-1,3,5 hexatrienyl, 1,3,5,7-octatetraenyl, 1,3,5,8-nonatetraenyl, 1,4,7,10-undecatetraenyl, 2-ethyl-1,3,6,8-nonatetraenyl, 2-ethenyl-1,3,5,8-nonatetraenyl, 1,3,5,7,9-decapentaenyl, 1,4,6,8,10-undecapentaenyl, and 1,4,6,9,11-dodecapentaenyl.

[0178] In the context of the present invention, substituted, linear or branched C2-C 30 Alkenyl refers to a C2-C alkyl group substituted with a functional group selected from alkoxy, C(=O)R, CN, and SR. 30 refers to a branched or straight-chain unsaturated hydrocarbon group having carbon atoms, where R is hydrogen, a substituted or unsubstituted straight or branched C-C 30 Alkyl, substituted or unsubstituted, straight or branched chain, 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 It is arylalkyl.

[0179] In the context of the present invention, the term "alkenyl" refers to any C-C alkyl group substituted with a functional group selected from alkoxy, C(=O)R, CN and SR. 30It further refers to branched or straight chain unsaturated hydrocarbon groups having carbon atoms; preferably 1-methoxyethenyl, 2-methoxypropenyl, 4-methoxybutenyl, 3-methoxypentenyl, 5-methoxyhexenyl, 2-methoxyheptenyl, 5-methoxyoctenyl, 3-methoxynonenyl, 6-methoxyundecenyl, 1-methoxydodec-2-enyl, 1-methoxytridec-5-enyl, 3-methoxytetradec-5-enyl, 3-methoxypentadeca- pentade)-12-encyl, 10-methoxyhexadec-15-enyl, 12-methoxyheptadec-16-enyl, 1-methoxyoctadec-3-enyl, 1-methoxynonadec-2-enyl, 1-methoxyeicos-20-enyl, 1-methoxyheneicos-2-enyl, 1-methoxydocos-4-enyl, 1-methoxytricos-22-enyl, 1-methoxytetracos-23-enyl, 2-meth 2-Methoxyprop-1-enyl, 2-methoxybut-1-enyl, 2-methoxypent-4-enyl, 2-methoxyhex-2-enyl, 2-methoxyhept-3-enyl, 2-methoxyoct-7-enyl, 2-methoxynon-5-enyl, 2-methoxyundec-10-enyl, 2-methoxydodec-4-enyl, 2-methoxytridec-12-enyl, 2-methoxytetradec-10-enyl, 2-methoxypentadec-14-enyl 2-Methoxyhexadec-1-enyl, 2-Methoxyheptadec-1-enyl, 2-Methoxyoctadec-12-enyl, 2-Methoxynonadec-10-enyl, 2-Methoxyeicos-18-enyl, 2-Methoxyheneicos-2-enyl, 2-Methoxydocos-3-enyl, 20-Methoxytricos-2-enyl, 21-Methoxytetracos-4-enyl, 1-Acetoxyethenyl, 1-Acetoxyprop-1-enyl acetoxybut-2-enyl, 1-acetoxypent-4-enyl, 1-acetoxyhex-2-enyl, 1-acetoxyhept-1-enyl, 1-acetoxyoct-7-enyl, 1-acetoxynon-2-enyl, 5-acetoxydec-3-enyl, 1-acetoxyundec-10-enyl, 1-acetoxydodec-2-enyl, 1-acetoxytridec-12-enyl, 10-acetoxytetradec-2-enyl,15-acetoxypentadec-2-enyl, 10-acetoxyhexadec-2-enyl, 11-acetoxyheptadeca-1-enyl, 13-acetoxyoctadec-2-enyl, 1-acetoxynonadec-14-enyl, 20-acetoxyeicos-19-enyl, 1-acetoxyhenicos-2-enyl, 1-acetoxydocos-10-enyl, 1-acetoxytricos-22-enyl, 1-acetoxytetracos-23-enyl, 1-cyanoeth-1-enyl, 1-cyanoprop-2-enyl, 1-cyanobut-2-enyl, 1-cyanopentadec-1-enyl -3-enyl, 1-cyanohex-5-enyl, 1-cyanohept-6-enyl, 1-cyanooct-2-enyl, 1-cyanonon-3-enyl, 11-cyanounde-2-enyl, 10-cyanododec-2-enyl, 10-cyanotridec-12-enyl, 1-cyanotetradec-3-enyl, 1-cyanopentadec-14-enyl, 1-cyanohexadec-15-enyl, 1-cyanoheptadec-2-enyl, 1-cyanooctadec-3-enyl, 1-cyanononadeca-18-enyl, 1-cyanoeicos-10-enyl, 1-cyanohenicosyl 2-cyanooct-20-enyl, 15-cyanodocos-3-enyl, 1-cyanotricos-20-enyl, 1-cyanotetracos-2-enyl, 2-cyanoprop-2-enyl, 2-cyanobut-1-enyl, 2-cyanopent-1-enyl, 2-cyanohex-3-enyl, 2-cyanohept-6-enyl, 2-cyanooct-1-enyl, 2-cyanonon-8-enyl, 2-cyanounde-10-enyl, 2-cyanododec-1-enyl, 2-cyanotridec-12-enyl, 2-cyanotetradec-10-enyl, 2-cyanopentadec-3-enyl, 2 -cyanohexadec-2-enyl, 2-cyanoheptadec-1-enyl, 2-cyanooctadec-12-enyl, 2-cyanononadeca-15-enyl, 2-cyanoeicos-1-enyl, 2-cyanoheneicos-5-enyl, 2-cyanodocos-20-enyl, 2-cyanotriicos-22-enyl, 2-cyanotetracos-20-enyl, 1-thionyleth-1-enyl, 1-thionylprop-2-enyl, 1-thionylbut-2-enyl, 1-thionylpent-4-enyl, 1-thionylhex-2-enyl, 1-thionylhept-5-enyl,Selected from the group consisting of 1-thionyloct-3-enyl, 1-thionylnon-5-enyl, 1-thionylundec-10-enyl, 1-thionyldodec-11-enyl, 1-thionyltridec-2-enyl, 1-thionyltetradec-4-enyl, 1-thionylpentadec-5-enyl, 1-thionylhexadec-3-enyl, 1-thionylheptadec-2-enyl, 1-thionyloctadec-3-enyl, 1-thionylnonadeca-15-enyl, 1-thionyleicos-18-enyl, 1-thionylheneicos-20-enyl, 1-thionyldocos-21-enyl, 1-thionyltricos-20-enyl and 1-thionyltetracos-22-enyl.

[0180] In the context of the present invention, the term "heteroalkyl" refers to an alkyl group in which one or more carbon atoms are replaced by heteroatoms, in each case independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH). Heteroalkyl preferably contains one, two, or three heteroatoms, independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH), as one or more chain bonds. Furthermore, heteroalkyl may have 2 to 12 members, preferably 2 to 6 members.

[0181] In the context of the present invention, the term "heteroalkenyl" refers to an alkenyl group in which one or more carbon atoms are replaced by heteroatoms, in each case independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH). Heteroalkenyl preferably contains one, two, or three heteroatoms, independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH), as one or more chain bonds. Furthermore, heteroalkenyl may be 3 to 12-membered, preferably 3 to 6-membered.

[0182] In the context of this invention, the term "cycloalkyl" refers to monocyclic and bicyclic saturated alicyclic radicals having 5 to 30 carbon atoms. Unsubstituted or branched C5-C 30Representative examples of monocyclic and bicyclic cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, and bicyclo[3.1.1]heptyl.

[0183] In the context of the present invention, C5 to C 30 Monocyclic and bicyclic cycloalkyls may be further branched with one or more of the same or different alkyl groups, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, n-pentyl, iso-pentyl, neo-pentyl, etc. Branched C3-C 10 Representative examples of monocyclic and bicyclic cycloalkyl include, but are not limited to, methylcyclohexyl and dimethylcyclohexyl.

[0184] In the context of this invention, the term "cycloalkenyl" refers to monocyclic and bicyclic unsaturated alicyclic radicals having 5 to 30 carbon atoms, containing one or more double bonds. 30 Representative examples of cycloalkenyl include, but are not limited to, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, or cyclodecenyl. These radicals may be branched with one or more of the same or different alkyl radicals, preferably methyl, ethyl, n-propyl, or isopropyl. Branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkenyls include, but are not limited to, methylcyclohexenyl and dimethylcyclohexenyl.

[0185] In the context of this invention, the term "heterocycloalkyl" means a non-aromatic monocyclic or polycyclic ring containing 5 to 30 ring members in which at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S, and N. Representative examples of heterocycloalkyl include, but are not limited to, aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl, and pyranyl.

[0186] In the context of this invention, the term "heterocycloalkenyl" refers to a non-aromatic unsaturated monocyclic or polycyclic ring containing 5 to 30 ring members in which at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S, and N, and having at least one double bond. Representative examples include, but are not limited to, (2,3)-dihydrofuranyl, (2,3)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1,4)-dihydropyridin-1-yl, dihydropyranyl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydro-pyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazolyl ... and (1,2,3,4)-tetrahydropyridin-1-yl.

[0187] In the context of the present invention, if one or more of the substituents denotes a mono- or polysubstituted heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, hetero-cycloalkyl and heterocycloalkenyl, this group is preferably selected from the group consisting of F, Cl, Br, I, -CN, -NO2, -OH, -SH, -NH2, oxo(=O), thioxo(=S), -C(=O)-OH, -C(=O)-OH, -C(=O)-C1-5 Alkyl, -C 2-5 Alkenyl, -C 2-5 Alkynyl, -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 1-5 -alkyl), -C(=O)-OC 1-5 -Alkyl, -C(=O)-H, -C(=O)-C 1-5 -Alkyl, -CH2-OC(=O)-phenyl, -OC(=O)-phenyl, -NH-S(=O)2-C 1-5 -Alkyl, -NH-C(=O)-C 1-5 -Alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -Alkyl, -C(=O)-N(C 1-5 -alkyl), pyrazolyl, phenyl, furyl (furanyl), thiadiazolyl, thiophenyl (thienyl) and benzyl, 1-5 The alkyl residues are in each case linear or branched, and the cyclic substituents or the cyclic residues of these substituents themselves are in each case unsubstituted or substituted with 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, -C1-5 Alkyl, -C 2-5 Alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -C(=O)-OC 1-5 It is believed that the aryl group is substituted with 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, substituents independently selected from the group consisting of -alkyl and -C(=O)-CF3.

[0188] In the context of the present invention, the term "aryl" refers to an aromatic compound that may have two or more aromatic rings. 30 Representative examples of aryl include, but are not limited to, phenyl, benzyl, cyclohexyl(phenyl)methyl, naphthyl, anthracenyl, tetraphenyl, phenalenyl, and phenanthrenyl.

[0189] In the context of the present invention, the term "heteroaryl" refers to a monocyclic or polycyclic, preferably monocyclic, bicyclic, or tricyclic aromatic hydrocarbon residue, preferably 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 ring members, particularly preferably 5, 6, 9, 10, 13, or 14 ring atoms, very particularly preferably 5 or 6 ring members, wherein one or more carbon atoms as ring members are replaced with heteroatoms independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH).Heteroaryl can contain, as ring members, preferably 1, 2, 3, 4, or 5 heteroatoms, preferably 1, 2, or 3 heteroatoms, independently selected from the group consisting of oxygen, sulfur, and nitrogen (NH). Heteroaryl can be unsubstituted, monosubstituted, or polysubstituted with the same or different groups. Representative examples of heteroaryl include, but are not limited to, thienyl, furyl, pyrrolyl, pyrazolyl, pyrazinyl, pyranyl, triazolyl, pyridinyl, imidazolyl, indolyl, isoindolyl, benzo[b]furanyl, benzo[b]thiophenyl, benzo[d]thiazolyl, benzodiazolyl, benzotriazolyl, benzoxazolyl, benzisoxazolyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridazinyl, pyrimidinyl, indazolyl, quinoxalinyl, quinazolinyl, quinolinyl, naphthridinyl, and isoquinolinyl.

[0190] In the context of this invention, an aryl or heteroaryl may be fused (annelated) to a monocyclic or bicyclic ring system. Representative examples of aryl fused to a monocyclic or bicyclic ring system include, but are not limited to, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, (2,3)-dihydro-1H-isoindolyl, (1,2,3,4)-tetrahydronaphthyl, (2,3)-dihydrobenzo[1.4]dioxinyl, benzo[1.3]dioxolyl, and (3,4)-dihydro-2H-benzo[1.4]oxazinyl.

[0191] In the context of this invention, the term "arylalkyl" refers to an aryl ring attached to an alkyl chain. Representative examples of arylalkyl 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.

[0192] In the context of the present invention, if one or more of the substituents denotes aryl, heteroaryl or arylalkyl or contains mono- or polysubstituted aryl or heteroaryl, this is preferably F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 -Alkyl, -C 2-5 Alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5 -Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5 -Alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-C 1-5-Alkyl, -S(=O)-C 1-5 -Alkyl, -NH-C 1-5 -Alkyl, N(C 1-5 alkyl)2, -C(=O)-OC 1-5 -Alkyl, -C(=O)-H; -C(=O)-C 1-5 -Alkyl, -CH2-OC(=O)-phenyl, -OC(=O)-phenyl, -NH-S(=O)2-C 1-5 -Alkyl, -NH-C(=O)-C 1-5 -Alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -Alkyl, -C(=O)-N(C 1-5 -alkyl), pyrazolyl, phenyl, furyl (furanyl), thiazolyl, thiadiazolyl, thio-phenyl (thienyl), benzyl and phenethyl, with the above C 1-5 The alkyl residues are in each case straight-chain or branched, and the cyclic substituents or the cyclic residues of these substituents themselves are unsubstituted or contain F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 Alkyl, -(CH2)-OC 1-5 -Alkyl, -C 2-5 Alkenyl, -C 2-5 Alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -SC 1-5 -Alkyl, -S-phenyl, -S-CH2-phenyl, -OC 1-5-substituted with 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, substituents independently selected from the group consisting 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 in each case F, Cl, Br, I, -CN, -NO2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-Butyl, n-pentyl, neopentyl, ethenyl, 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, furyl (furanyl), thiadiazolyl, thio-phenyl (thienyl) and benzyl, where the cyclic substituents or the cyclic residues of these substituents themselves are in each case unsubstituted or are selected independently from the group consisting of F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert.-Butyl, n-pentyl, neopentyl, ethenyl, 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, It is substituted independently by 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, substituents selected from the group consisting of -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.

[0193] In the context of the present invention, substituted aryl is selected from the group consisting of 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-aminophenyl, 3-aminophenyl, 4-aminophenyl, 2-dimethylaminophenyl, 3-dimethylaminophenyl, 4-dimethylaminophenyl, 2-methylaminophenyl, 3-methylaminophenyl, 4-methylaminophenyl, 2-acetylphenyl, 3-acetylphenyl, 4-acetylphenyl, 2-methylsulfinylphenyl, 3-methylsulfinylphenyl, 4-methylsulfinylphenyl, 2-methylsulfonylphenyl, 3-methylsulfonylphenyl, 4-methylsulfonylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-di ... 2-tert.-butylphenyl, 3-tert.-butylphenyl, 4-tert.-butylphenyl, 4-tert.-butylphenyl, 4-tert.-butylphenyl, 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 ... rt.-butylphenyl, 2-carboxyphenyl, 3-carboxyphenyl, 4-carboxyphenyl, 2-ethenylphenyl, 3-ethenylphenyl, 4-ethenylphenyl, 2-ethynylphenyl, 3-ethynylphenyl, 4-ethynylphenyl, 2-allylphenyl, 3-allylphenyl, 4-allylphenyl, 2-trimethylsilanylethynylphenyl, 3-trimethylsilanylethynylphenyl, 4-trimethylsilanylethynylphenyl, 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-carboxy-tert.-butyl ester phenyl, 3-carboxy-tert.-butyl ester phenyl, 4-carboxy-tert.-butyl ester phenyl, 2-methylmercaptophenyl, 3-methylmercaptophenyl, 4-methylmer captophenyl, 2-ethylmercaptophenyl, 3-ethylmercaptophenyl, 4-ethylmercaptophenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoro-methoxyphenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-4-methylphenyl, (2,3)-difluorophenyl, (2, 3)-dimethylphenyl, (2,3)-dichlorophenyl, 3-fluoro-2-trifluoro-methylphenyl, (2,4)-dichlorophenyl, (2,4)-difluorophenyl, 4-fluoro-2-trifluoromethylphenyl, (2,4)-dimethoxyphenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-nitrophenyl, 2-chloro-4-methylphenyl, 2-chloro-5-trifluoromethylphenyl, 2-chloro-5-methoxyphenyl, 2-bromo-5-trifluoromethylphenyl, 2-bromo-5-methoxyphenyl,(2,4)-dibromophenyl, (2,4)-dimethylphenyl, 2-fluoro-4-trifluoromethylphenyl, (2,5)-difluorophenyl, 2-fluoro-5-trifluoro-methylphenyl, 5-fluoro-2-trifluoromethylphenyl, 5-chloro-2-trifluoromethylphenyl, 5-bromo-2-trifluoromethylphenyl, (2,5)-dimethoxyphenyl, (2,5)-bis-trifluoromethylphenyl, (2,5)-dichlorophenyl, (2,5)-dibromophenyl, 2-methoxy-5-nitrophenyl, 2-Fluoro-6-trifluoro-methylphenyl, (2,6)-dimethoxyphenyl, (2,6)-dimethylphenyl, (2,6)-dichlorophenyl, 2-chloro-6-fluorophenyl, 2-bromo-6-chlorophenyl, 2-bromo-6-fluorophenyl, (2,6)-difluorophenyl, (2,6)-difluoro-3-methylphenyl, (2,6)-dibromophenyl, (2,6)-dichlorophenyl, 3-chloro-2-fluorophenyl, 3-chloro-5-methylphenyl, (3,4)-dichlorophenyl, (3,4)-dimethylphenyl phenyl, 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-trifluoromethylphenyl thyl, 4-bromo-3-methylphenyl, 4-bromo-5-methylphenyl, 3-chloro-4-fluorophenyl, 4-fluoro-3-nitrophenyl, 4-bromo-3-nitrophenyl, (3,4)-dibromophenyl, 4-chloro-3-methylphenyl, 4-bromo-3-methylphenyl, 4-fluoro-3-methylphenyl, 3-fluoro-4-methylphenyl, 3-fluoro-5-methylphenyl, 2-fluoro-3-methylphenyl, 4-methyl-3-nitrophenyl, (3,5)-dimethoxyphenyl, (3,5)-dimethylphenyl,(3,5)-bis-trifluoromethylphenyl, (3,5)-difluorophenyl, (3,5)-dinitrophenyl, (3,5)-dichlorophenyl, 3-fluoro-5-trifluoromethylphenyl, 5-fluoro-3-trifluoro-methylphenyl, (3,5)-dibromophenyl, 5-chloro-4-fluorophenyl, 5-chloro-4-fluorophenyl, 5-bromo-4-methylphenyl, (2,3,4)-trifluorophenyl, (2,3,4)-trichlorophenyl, (2,3,6)-trifluorophenyl, 5-chloro-2-methoxyphenyl, (2,3)-difluoro-4-methyl, (2,4,5)-trifluorophenyl, (2,4,5)-trichlorophenyl The fluorophenyl group may be selected from the group consisting of 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-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.

[0194] In the context of the present invention, examples of substituted heteroaryl are 3-methylpyrid-2-yl, 4-methylpyrid-2-yl, 5-methylpyrid-2-yl, 6-methylpyrid-2-yl, 2-methylpyrid-3-yl, 4-methylpyrid-3-yl, 5-methylpyrid-3-yl, 6-methylpyrid-3-yl, 2-methylpyrid-4-yl, 3-methylpyrid-4-yl, 3-fluoropyrid-2-yl, 4-fluoropyrid-2-yl, 5-fluoropyrid-2-yl, 6-fluoropyrid-2-yl, 3-chloropyrid-2-yl, 4-chloropyrid -2-yl, 5-chloropyrid-2-yl, 6-chloropyrid-2-yl, 3-trifluoromethylpyrid-2-yl, 4-trifluoromethylpyrid-2-yl, 5-trifluoromethylpyrid-2-yl, 6-trifluoromethylpyrid-2-yl, 3-methoxypyrid-2-yl, 4-methoxypyrid-2-yl, 5-methoxypyrid-2-yl, 6-methoxypyrid-2-yl, 4-methylthiazol-2-yl, 5-methylthiazol-2-yl, 4-trifluoromethylthiazol-2-yl, 5-trifluoromethylthiazol-2-yl -yl, 4-chlorothiazol-2-yl, 5-chlorothiazol-2-yl, 4-bromothiazol-2-yl, 5-bromothiazol-2-yl, 4-fluorothiazol-2-yl, 5-fluorothiazol-2-yl, 4-cyanothiazol-2-yl, 5-cyanothiazol-2-yl, 4-methoxythiazol-2-yl, 5-methoxythiazol-2-yl, 4-methyloxazol-2-yl, 5-methyloxazol-2-yl, 4-trifluoromethyloxazol-2-yl, 5-trifluoromethyloxazol-2-yl oxazol-2-yl, 4-chlorooxazol-2-yl, 5-chlorooxazol-2-yl, 4-bromooxazol-2-yl, 5-bromooxazol-2-yl, 4-fluorooxazol-2-yl, 5-fluorooxazol-2-yl, 4-cyanooxazol-2-yl, 5-cyanooxazol-2-yl, 4-methoxyoxazol-2-yl, 5-methoxyoxazol-2-yl, 2-methyl-(1,2,4)-thiadiazol-5-yl, 2-trifluoromethyl-(1,2,4)-thiadiazolyl-5-yl, 2-chloro-(1,2,4)-thiadiazol-5-yl, 2-fluoro-(1,2,4)-thiadiazol-5-yl, 2-methoxy-(1,2,4)-thiadiazol-5-yl, 2-cyano-(1,2,4)-thiadiazol-5-yl, 2-methyl-(1,2,4)-oxadiazol-5-yl, 2-trifluoromethyl-(1,2,4)-oxadiazol-5-yl, 2-chloro-(1,2,4)-oxadiazol-5-yl, 2-fluoro-(1,2,4)-oxadiazol-5-yl, 2-methoxy-(1,2,4)-oxadiazol-5-yl, and 2-cyano-(1,2,4)-oxadiazol-5-yl.

[0195] In the context of the present invention, the term "substituted" with respect to any one of alkylene, heteroalkylene, alkenylene, heteroalkenylene, cycloalkylene, heterocyclo-alkylene, cycloalkenylene, heterocycloalkenylene, arylene, and heteroarylene disclosed herein refers to mono- or polysubstituted alkylene, heteroalkylene, alkenylene, heteroalkenylene, cycloalkylene, heterocycloalkylene, cycloalkenylene, heterocycloalkenylene, arylene, and heteroarylene, respectively, which may be substituted with preferably 1, 2, 3, 4, or 5, more preferably 1, 2, or 3, substituents. Examples of substituents include -NHR 1 (In the formula, R 1 -C(R u )(R v )(R w )-is) and R u , R v and R w are, independently of one another, hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 Alkyl, straight or branched, substituted or unsubstituted, C2-C 30 Alkenyl, substituted or unsubstituted straight or branched chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight or branched chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5~C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5-30 membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6~C 30 Aryl and substituted or unsubstituted C1-C 10 More preferably, R is selected from the group consisting of alkylene, 5- to 30-membered heteroaryl. u , R v and R w are, independently of one another, hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. More preferably, R u , R v and R w are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of hydrogen, methyl, and ethyl, more preferably selected from the group consisting of hydrogen, methyl, and ethyl. Alternatively, and preferably, -NHR 1 In R 1 is -C(R u )(R v )(Rw ) where C and R u is substituted or unsubstituted C6-C 30 Forming an arylene, R v and R w Neither of these exists. For example, -NHR 1 can be -NH-Ph.

[0196] In the context of the present invention, -Z 12 -About -N(R f )- means that the N atom is C of formula (I) a R bonded to f and thus forming a heterocycle.

[0197] In the context of the present invention, a reversible NCO bond refers to a bond between the N (from the secondary hindered amine) of the urea group and the C (of the NCO) that can be reversibly formed and broken.

[0198] In the context of the present invention, "thermosetting polymer" refers to a network polymer comprising a covalent structure with at least three covalent bond attachment points between polymer chains, preferably at least three covalent bond attachment points between polymer chains that form part of a polymer network.

[0199] In the context of the present invention, "thermoplastic polymer" refers to a linear polymer comprising a covalent structure with two covalent bond attachment points between polymer chains, preferably the two covalent bond attachment points between polymer chains form part of a linear polymer system.

[0200] In the context of the present invention, isocyanate is a general term for molecules that contain at least one isocyanate functional group. Therefore, the interpretation of the term "at least one isocyanate" includes monoisocyanates, diisocyanates, triisocyanates, tetraisocyanates, and isocyanates with a larger number of isocyanate functional groups, such as polymers with one or more isocyanate functional groups. An example of an isocyanate in the context of the present invention is polymethylene polyphenylisocyanate, also commonly known as pMDI.

[0201] In the context of the present invention, the abbreviation "SHA" represents a secondary hindered amine. Secondary hindered amine is a general term well known in the art. In particular, in the term, a secondary amine is given the usual definition of an amine bonded to two separate carbon atoms of any hybridization, and said carbon atoms cannot be carbon atoms of a carbonyl group. A hindered substituent is defined as at least one carbon bonded to an amino group, and said carbon atom is further directly bonded to at least two other carbon groups. A non-limiting example of a secondary hindered amine in the context of the present invention is represented by the following formula: CH3-CH2-CH(CH3)-NH-[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -NH-CH(CH3)-CH2-CH3 (wherein R x1 is -CH2-CH3, and R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-CH(CH3)-CH2-CH3, where m1+n1+o1 is in the range of 5 to 6), 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA), DIB-butanediamine (N,N'-di-sec-butyl-1,4-butanediamine) or sec-butyl-modified polyetheramine.

[0202] The present invention is further illustrated by the following examples. [Example]

[0203] <Material abbreviation> PolyTHF (commercial product of BASF): polytetrahydrofuran (polytetramethylene ether glycol) (functionality = 2; average molecular weight Mn = 2000 g / mol, OH = 56 mg KOH / g). MDI: 4,4'-methylenebis(phenyl isocyanate) (purchased from BASF Polyurethanes GmbH) BDO: 1,4-butanediol (purchased from Alfa Aesar) DIBIS: diethylene glycol bischloroformate (purchased from BASF Polyurethanes GmbH) Benzoyl chloride (purchased from Sigma Aldrich) TDI, a mixture of 80% 2,4-toluene diisocyanate and 20% 2,6-toluene diisocyanate (purchased from BASF) pMDI: Polymeric diphenylmethane diisocyanate (BASF product) DIB-MDA: 4,4'-methylenebis(N-sec-butylaniline) (purchased from abcr) DIB-butanediamine: N,N'-di-sec-butyl-1,4-butanediamine DIB-polyetheramine T403 (prepared from polyetheramine T403 purchased from BASF) Polyol 1 = trifunctional polyether polyol, containing mainly secondary hydroxyl groups - functionality = 3, Mn = 3500 g / mol, OH = 48 mgKOH / g, viscosity (25 °C) = 600 mPa·s. Polyol 2 = Glycerin-based trifunctional polyether polyol - functionality = 3, Mn = 420 g / mol, OH = 400 mg KOH / g, viscosity (25 °C) = 373 mPa·s Polymer type TP: Thermoplastic resin Polymer type TS: Thermosetting resin

[0204] <Analysis method> TGA (Thermogravimetric Analysis): Spectra were obtained according to ISO 11358 under N2 atmosphere in gold crucibles.

[0205] NCO content: The NCO content was determined in accordance with DIN EN ISO 14896 using a Metrohm Modell 916 TI-Touch.

[0206] Melting point: A sample of polyurethaneurea was placed on a 0.2 x 0.2 x 0.2 cm 3 The samples were cut into cubes with dimensions of 0.01 mm and transferred to a hot press (P / O / Weber model number: PW20H, 2006). Using a circular press with a diameter of 17 cm, the samples were pressed with a force of 20 kN, equivalent to a pressure of approximately 880 kPa, for at least 5 minutes while the temperature was increased. The melting point was determined when the solid polymer underwent a visible phase transition.

[0207] DSC (Differential Scanning Calorimetry) Measurement: DSC analysis was performed according to ASTM D 3418 using a TA Instruments brand DSC model Q20 on approximately 5-10 mg of sample.

[0208] Swelling ratio, insoluble and soluble fractions: Polyurethane urea samples were placed on a 0.5 x 0.5 x 0.5 cm 3 The samples were swollen in THF for 24 hours at room temperature. Afterwards, excess THF was removed. The swollen samples were weighed (m(swollen)). The samples were first dried at ambient conditions and then dried under vacuum at 65°C to remove the trapped THF. Finally, the mass of the dried samples was evaluated (m(dried)). The swelling ratio and insoluble fraction were determined by the following formulas: Swelling rate=[m(swollen)-m(dried)] / m(dried) Insoluble fraction = m(dried) / m(dry) Soluble fraction = 1 - insoluble fraction

[0209] [Table 1]

[0210] <Reference Example 1A: Preparation of prepolymer> 100 g of 4,4'-methylenebis(phenylisocyanate) (mMDI) (0.400 mol) was placed in a flask and placed under N2. The mixture was heated. Once the MDI was melted, 0.02 g (141 μmol) of benzoyl chloride was added. 233 g of polytetrahydrofuran (polyTHF) (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the mMDI-containing mixture at 80 °C. The reaction was terminated by cooling when the NCO value reached <8% (molar ratio NCO:OH approximately 1:0.3). Prepolymer 1a was obtained as a colorless, slightly opaque liquid.

[0211] <Reference Example 1B: Preparation of prepolymer> 17.4 g of toluene diisocyanate (TDI) (0.100 mol) was placed in a flask and placed under N2. The mixture was heated to 80 °C and 0.008 g of diglycol bischloroformate (DIBIS) (35 μmol) was added. 62 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the TDI mixture at 80 °C. The reaction was terminated by cooling when the NCO value reached <8% (molar ratio NCO:OH approximately 1:0.3). Prepolymer 1b was obtained as a colorless, slightly opaque liquid.

[0212] <Reference Example 1C: Preparation of prepolymer> 34.0 g of polymeric diphenylmethane diisocyanate (pMDI) (0.100 mol) and 8 mg of DIBIS (35 μmol) were mixed. 75.0 g of polyTHF (functionality = 2, M n= 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the pMDI-containing mixture at 80 °C. The reaction was terminated by cooling when the NCO value reached <8% (molar ratio NCO:OH approximately 1:0.25). Prepolymer 1c was obtained as a brownish, slightly opaque liquid.

[0213] <Reference Example 1D: Preparation of prepolymer> 20.0 g of mMDI (0.060 mol) was added to 20.0 g of pMDI (0.080 mol) and 8 mg of DIBIS (35 μmol). 77.5 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the mMDI / pMDI-containing mixture at 80 °C. The reaction was terminated by cooling when the NCO value reached <8% (molar ratio NCO:OH approximately 1:0.3). The prepolymer was obtained as a brownish, slightly opaque liquid.

[0214] Reference Example 2: Preparation of prepolymer 75.0 g of MDI (0.300 mol) was placed in a flask and placed under N. This was heated to 80 °C and 188 g of Polyol 1 (trifunctional polyether polyol with secondary hydroxyl groups and propylene oxide (PO) end-capping, functionality = 3, M n A mixture of 0.008 g of DIBIS (35 μmol) with 0.008 g of dimethylformamide (DPOF, hydroxyl value = 48 mg KOH / g, viscosity (25 °C) = 600 mPa*s) and 0.008 g of DIBIS (35 μmol) was slowly added at 80 °C. The reaction was terminated by cooling when the NCO value reached <8% (molar ratio NCO:OH approximately 1:0.3). Prepolymer 2 was obtained as a colorless, slightly opaque liquid.

[0215] <Reference Example 3: Preparation of DIB-polyetheramine T403> A 300 mL steel pressure autoclave was charged with 100 g (0.21 mol, 1 eq.) of polyetheramine T403 and 26.6 g of butan-2-one (0.36 mol, 1.7 eq.) in the presence of palladium catalyst (Pd / Ag on alumina with predominantly θ, 0.3 wt. % Pd, 0.1 wt. % Ag based on alumina, EM distribution eggshell, catalyst purchased from BASF—such catalysts are described in WO 2006 / 040159) (17.75 g, 14.06 wt. %). The autoclave was sealed, purged with nitrogen, and heated to 140 °C under atmospheric pressure. The autoclave was subsequently pressurized with H (160 bar) at the same temperature for 20 h. The autoclave was cooled and vented. The crude compound was filtered and the volatiles and water removed under reduced pressure to give 98 g of a clear, colorless liquid which was used without further purification.

[0216] Comparative Example 1A: Preparation of poly(urea-urethane) polymer according to the prior art and its recyclability test 60.0 g of prepolymer 1a (7.94% NCO) obtained according to Reference Example 1A was heated to 70 °C, degassed, and placed under N2. 4.67 g of 1,4-butanediol (BDO) (51.8 mmol) was added (molar ratio NCO:OH 1.00:1.00 to 1.05:1.00), and the mixture was stirred at 2000 rpm in a speed mixer for 20 s. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 40 min. The material was obtained as a white, opaque solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0217] Recyclability test (melting): The obtained plate samples were cut into small cubes (0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed at 880 kPa for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 110-120°C and formed cookie-shaped plates after cooling. Further testing is disclosed in Examples 9 and 10 below.

[0218] Example 1A: Preparation of Covalent Adaptable System (CAS) Poly(urea-urethane) Polymer According to the Present Invention and Testing of Its Recyclability 60.0 g of prepolymer 1a (7.94% NCO) obtained according to Reference Example 1A was heated to 70 °C, degassed, and placed under N2. 16.1 g of 4,4'-methylene-bis[N-(1-methylpropyl)-phenylamine] (DIB-MDA) (51.8 mmol) was added (molar ratio NCO:NH was 1.00:1.00 to 1.05:1.00), and the mixture was stirred at 2000 rpm in a speed mixer for 20 s. The resulting mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 40 min. The material was obtained as a yellow, transparent solid plate. The properties of the resulting material are listed in Tables 1 and 2.

[0219] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed under 880 kPa pressure for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt near 70°C and formed thin foils after cooling. Further testing is disclosed in Examples 9 and 10 below.

[0220] Conclusion: The product obtained according to the invention begins to melt at a temperature of about 70° C., much lower than Comparative Example 1A, making it possible to form thin foils and which are recyclable.

[0221] Comparative Example 1B: Preparation of Poly(urea-urethane) Polymer According to the Prior Art 30.0 g of prepolymer 1b (7.47% NCO) obtained according to Reference Example 1B was heated to 70 °C, degassed, and placed under N2. 2.29 g of 1,4-butanediol (BDO) (25.4 mmol) was added (molar ratio NCO:OH 1.00:1.00 to 1.05:1.00), and the mixture was stirred at 2000 rpm in a speed mixer for 20 s. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 16 h. The material was obtained as a colorless, transparent, viscoelastic plate, which was already fluid at room temperature. The properties of the resulting material are listed in Tables 1 and 2.

[0222] Example 1B: Preparation of a Covalent Adaptable System (CAS) Poly(urea-urethane) Polymer According to the Present Invention 30.0 g of prepolymer 1b (7.47% NCO) from Reference Example 1B was heated to 70 °C, degassed, and placed under N2. 8.39 g of DIB-MDA (25.4 mmol) was added (molar ratio NCO:NH 1.00:1.00 to 1.05:1.00), and the mixture was stirred in a speed mixer at 2000 rpm for 20 s. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 40 min. The material was obtained as a yellow, transparent, viscoelastic plate that was already flowable at room temperature. The properties of the resulting material are listed in Tables 1 and 2.

[0223] Comparative Example 1C: Preparation of poly(urea-urethane) polymer according to the prior art and its recyclability test 30.0 g of prepolymer 1c (7.15% NCO) from Reference Example 1C was mixed with 2.19 g of BDO (24.2 mmol) (molar ratio NCO:OH 1.05:1.00) and stirred in a speed mixer at 2000 rpm for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a brownish, opaque solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0224] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm).3 ) and transferred to a hot press. The samples were pressed for at least 5 minutes at a pressure of 880 kPa (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples did not melt up to a temperature of 180°C.

[0225] Example 1C: Preparation of Covalently Bonded Adaptive Network (CAN) Poly(urea-urethane) Polymer According to the Present Invention and Testing of Its Recyclability 30.0 g of prepolymer 1c (7.15% NCO) from Reference Example 1C was mixed with 8.03 g of DIB-MDA (24.2 mmol) (molar ratio NCO:OH 1.05:1.00) and stirred in a speed mixer at 2000 rpm for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a brownish, opaque solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0226] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed under 880 kPa pressure for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 160 °C and formed thin foils after cooling.

[0227] Conclusion: Contrary to Comparative Example 1C, the product obtained according to the invention is meltable, can be formed into thin foils and is recyclable.

[0228] Comparative Example 1D: Preparation of poly(urea-urethane) polymer according to the prior art and its recyclability test 25.0 g of prepolymer 1d (7.85% NCO) obtained according to Reference Example 1D was mixed with 2.00 g of BDO (22.2 mmol) (molar ratio NCO:OH 1.05:1.00) and stirred in a speed mixer at 2000 rpm for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as an opaque, off-white solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0229] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed for at least 5 minutes at a pressure of 880 kPa (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples did not melt up to a temperature of 180°C.

[0230] Example 1D: Preparation of Covalently Bonded Adaptive Network (CAN) Poly(urea-urethane) Polymer According to the Present Invention and Testing of Its Recyclability 25.0 g of prepolymer 1d (7.85% NCO) obtained according to Reference Example 1D was mixed with 7.35 g of DIB-MDA (22.2 mmol) (molar ratio NCO:OH 1.05:1.00) and stirred in a speed mixer at 2000 rpm for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellow, slightly opaque solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0231] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed under 880 kPa pressure for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 140 °C and formed thin foils after cooling.

[0232] Conclusion: Contrary to Comparative Example 1D, the product obtained according to the invention is meltable, can be formed into thin foils and is recyclable.

[0233] Comparative Example 2: Preparation of poly(urea-urethane) polymer according to the prior art and test of its recyclability 30.0 g of prepolymer 2 (7.50% NCO) prepared according to Reference Example 2 and 2.30 g of BDO (25.3 mmol) were added (molar ratio NCO:OH 1.00:1.00 to 1.05:1.00), and the mixture was stirred at 2000 rpm in a speed mixer for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separating foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a white, opaque solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0234] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed for at least 5 minutes at a pressure of 880 kPa (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples did not melt up to a temperature of 180°C.

[0235] Recyclability test (extrusion). To test the extrudability, samples of the obtained plates were cut into small cubes (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to an extruder. The sample was extruded at 200°C, but did not melt and the material clogged the extruder. When the extrusion chamber was opened, the material was again obtained as a crumbly solid.

[0236] Example 2: Preparation of covalently bonded adaptive network (CAN) poly(urea-urethane) polymer according to the present invention and testing of its recyclability 30.0 g of prepolymer 2 (7.50% NCO) prepared according to Reference Example 2 and 8.43 g of DIB-MDA (25.5 mmol) were added (molar ratio NCO:NH of 1.00:1.00 to 1.05:1.00), and the mixture was stirred at 2000 rpm in a speed mixer for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separating foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellow, opaque solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0237] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed under 880 kPa pressure for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 100 °C and formed thin foils after cooling.

[0238] Conclusion: Contrary to Comparative Example 2, the product obtained according to the invention is meltable, can be formed into thin foils and is recyclable.

[0239] Recyclability test (extrusion). To test the extrudability, samples of the obtained plates were cut into small cubes (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to an extruder. The samples were extruded at 180°C. At this temperature, the samples could be extruded as a homogeneous, flowable paste with a maximum torque of 2.2 kNm.

[0240] Conclusion: Contrary to Comparative Example 2, the product obtained according to the invention can be extruded to form a homogeneous paste and is recyclable.

[0241] Comparative Example 3: Preparation of poly(urea-urethane) polymer according to the prior art 60.0 g of prepolymer 1a (7.43% NCO) obtained according to Reference Example 1A and 14.15 g of polyol 2 (functionality = 3, M n= 400 g / mol, hydroxyl value = 400 mg KOH / g) was added (molar ratio NCO:OH = 1.05:1.00), and the mixture was stirred in a speed mixer at 2000 rpm for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separating foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellowish, transparent solid plate. The properties of the resulting material are shown in Tables 1 and 2.

[0242] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed for at least 5 minutes at a pressure of 880 kPa (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples did not melt up to a temperature of 180°C.

[0243] Example 3: Preparation of covalently bonded adaptive network (CAN) poly(urea-urethane) polymers according to the present invention 60.0 g of prepolymer 1a (7.50% NCO) obtained according to Reference Example 1A and 21.1 g of DIB-polyetheramine T403 (sec-butyl-modified polyetheramine T403, functionality = 3, M n = 600 g / mol, amine value = 270 mg KOH / g) was added (molar ratio NCO:NH 1.05:1.00), and the mixture was stirred at 2000 rpm in a speed mixer for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separating foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellow, opaque solid. The properties of the resulting material are shown in Tables 1 and 2.

[0244] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3) and transferred to a hot press. The samples were pressed under 880 kPa pressure for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 100 °C and formed thin foils after cooling.

[0245] Conclusion: Contrary to Comparative Example 3, the product obtained according to the invention is meltable, can be formed into thin foils and is recyclable.

[0246] [Table 2]

[0247] Example 4: Preparation of a composite material according to the present invention containing glass fibers 30.0 g of prepolymer 2 (6.87% NCO) obtained according to Reference Example 2 was heated to 70 °C, degassed, and placed under N2. 7.26 g of DIB-MDA (51.8 mmol) (molar ratio NCO:NH 1.05:1.00) was added. The mixture was stirred in a speed mixer at 2000 rpm for 20 seconds. 300 mg of a single glass fiber was then added as a filler. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 40 minutes. The material was obtained as a yellow, opaque plate.

[0248] Example 5: Mechanical Recycling The material from Example 4 was cut and pressed at 140°C under 880 kPa pressure (20 kN force applied in a 17 cm diameter circular press according to the melting point analysis method described above) for at least 5 minutes, resulting in a thin foil, demonstrating that the composite is mechanically recyclable.

[0249] Example 6: Mechanical recycling test of composite material according to the present invention A sample of the yellow opaque solid plate obtained according to Example 2 was cut into a small cube (approximately 0.2 x 0.2 x 0.2 cm 3) and transferred to a hot press. The samples were pressed at 140°C under a pressure of 880 kPa for at least 5 minutes to obtain a thin foil (20 kN force in a 17 cm diameter circular press according to the melting point analysis method described above). A single glass fiber was placed between two pieces of foil, and the structure was pressed at 140°C under a pressure of 880 kPa for at least 5 minutes to obtain a composite in the form of a thin foil (20 kN force in a 17 cm diameter circular press according to the melting point analysis method described above).

[0250] Recycling test: The resulting composite material in the form of a thin foil was cut into pieces, and the pieces were pressed at 140°C for at least 5 minutes under a pressure of 880 kPa (a force of 20 kN was applied to a circular press with a diameter of 17 cm according to the melting point analysis method described above). As a result, a thin foil was obtained, demonstrating that the composite material was mechanically recyclable.

[0251] Example 7: Chemical recycling of composite materials according to the present invention 22.0 g of the composite from Example 4 was immersed in 150 mL of dry toluene and heated to reflux with stirring. The material began to swell, and the resin was completely dissolved after 4 hours. When the solution was cooled, the mixture underwent a sol-gel transition that was reversible when heated again. The dissolved gel was then hot filtered to remove the glass fibers.

[0252] The filtrate was collected in a flask and was dried under reduced pressure at elevated temperature, first in a rotary evaporator at 120°C and 50 mbar, and then in a vacuum oven at 80°C.

[0253] The resulting solid was pressed at 140°C with a pressure of 880 kPa for at least 5 minutes to obtain a thin foil (20 kN force applied in a 17 cm diameter circular press according to the melting point analysis method described above). A single glass fiber was placed between two pieces of foil, and the structure was pressed at 140°C with a pressure of 880 kPa for at least 5 minutes to obtain a new composite material from the recycled polymer (20 kN force applied in a 17 cm diameter circular press according to the melting point analysis method described above). Chemical recycling according to Example 7 is shown in Figure 3.

[0254] Example 8: Chemical recycling in the presence of amines Approximately 5 g of the bulk material (poly(urea urethane) polymer) obtained according to Example 2 was immersed in 50 mL of toluene. 2.6 g of DIB-MDA (1 equivalent relative to the reversible NCO bond) was added to remove the open NCO bond formed by thermal decomposition of the urea bond. After stirring under reflux for 16 hours, the material was completely dissolved. The toluene was removed under reduced pressure to obtain a mixture containing the amine-terminated prepolymer as a viscous liquid that did not solidify. The mixture was diluted with 1 mL of toluene, and the amine-terminated prepolymer was precipitated by adding it to 50 g of n-heptane to remove excess DIB-MDA. The amine-terminated prepolymer was separated from the solvent, and the DIB-MDA was dissolved therein by decantation. The amine-terminated prepolymer was then dried to obtain 4.51 g of amine (DIB-MDA)-terminated prepolymer with an amine value of 75.2 mg KOH / g.

[0255] Formation of a new poly(mochevinoi) polymer (bulk material): This amine (DIB-MDA) terminated prepolymer was reacted with the prepolymer of Example 2 to obtain a recycled covalently bonded adaptive network (CAN) poly(mochevinoi) polymer, which is the same material as the bulk material (poly(mochevinoi) polymer) obtained according to Example 2.

[0256] <Example 9: Testing of polymers obtained in Example 1A and Comparative Example 1A - Recycle properties> The plates obtained according to Example 1A and Comparative Example 1A were cut into small cubes (approximately 0.2 x 0.2 x 0.2 cm 3 ) was cut.

[0257] 19.1 A sample of approximately 5 g of the material from Example 1A was mixed with 50 mL of toluene and heated under reflux for 16 hours. The mixture was then cooled. The CAS material from Example 1A was completely dissolved in toluene to give a homogeneous yellowish liquid mixture. After removing the solvent, a transparent yellowish solid was obtained.

[0258] 19.2 An approximately 5 g sample of the material from Comparative Example 1A was mixed with 50 mL of toluene and heated under reflux for 16 hours. The mixture was then cooled. The material did not dissolve.

[0259] This example is shown in Figure 1. This example therefore demonstrates that, unlike prior art materials, the CAS material according to the present invention is reversibly soluble in toluene, allowing its chemical recycling.

[0260] Example 10: Test of polymers obtained in Example 1A and Comparative Example 1A - Melting behavior The materials obtained in Example 1A and Comparative Example 1A were cut into small cubes (approximately 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press, where they were compression molded at 20 kN for 5 min at different temperatures, i.e., 80 °C, 100 °C, and 120 °C. The resulting products are shown in Figure 2.

[0261] The material of Example 1A already formed a foil at 80° C., while the material of the comparative example remained as white pieces at both 80° C. and 100° C. At 120° C., the comparative example formed fine white opaque plates, while the inventive example formed fine transparent foils. This demonstrates that the material of the present invention melts at a much lower temperature than conventional materials.

[0262] Example 11: Preparation of covalently bonded adaptive network (CAN) poly(urea-urethane) polymers according to the present invention from aliphatic diamines 60.0 g of Reference Example 2 (7.50% NCO) and 9.44 g of DIB-butanediamine (N,N'-di-sec-butyl-1,4-butanediamine) (47.1 mmol) were added (molar ratio NCO:NH of 1.05:1.00), and the mixture was stirred in a Speedmixer at 2000 rpm for 20 seconds. The mixture immediately turned solid and was cured at 105°C for 1 hour and at room temperature for 48 hours to give an off-white, opaque material.

[0263] Recyclability test (melting): The obtained plate samples were cut into small cubes (0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed under 880 kPa pressure for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 100°C and formed circular plates after cooling.

[0264] Recyclability test (solution, toluene). 2 g of the plate obtained in the melting test was cut into small cubes (0.2 × 0.2 × 0.2 cm). 3 The sample was cut into strips and immersed in 20 mL of toluene. The mixture was heated to 110°C for 24 hours. The sample did not dissolve.

[0265] Recyclability test (solution, DMI). 2 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm3) and immersed in 20 mL of 1,3-dimethyl-2-imidazolidinone. The mixture was heated to 130 °C for 24 hours. The sample was completely dissolved to form a clear solution.

[0266] Higher temperatures are required to recycle the polymers containing aliphatic amines according to the present invention by dissolving them in organic solvents.

[0267] <Reference Example 4: Preparation of prepolymer> 20 g of 4,4'-methylene-bis-(phenylisocyanate) (MDI, functionality 2) (0.080 mol) and 20 g of Lupranat M20 FB (pMDI, functionality approximately 2.5) (0.06 mol) were placed in a flask and placed under N2. The mixture was heated and, once the MDI had melted, 0.02 g of benzoyl chloride (141 μmol) was added. 82.6 g of polytetrahydrofuran (polyTHF) (f = 2, M n= 2000 g / mol, #OH = 55 mg KOH / g) was melted and slowly added to the MDI / pMDI mixture at 80 °C. The reaction was terminated by cooling when the NCO value reached <8% (molar ratio NCO:OH approx. 1:0.3). The prepolymer was obtained as a yellow, transparent liquid.

[0268] Example 12: Preparation of a covalently bonded adaptive network (CAN) poly(urea-urethane) polymer according to the present invention from N-(2-hydroxyethyl)aniline 15.0 g (7.3% NCO) of the prepolymer described in Reference Example 4 and 1.70 g of N-(2-hydroxyethyl)aniline (12.4 mmol) were added (molar ratio NCO:XH of 1.05:1.00, X = total of O and N), and the mixture was stirred at 2000 rpm in a speed mixer for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separating foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellow, opaque solid plate.

[0269] Recyclability test (melting): The obtained plate samples were cut into small cubes (0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed at 880 kPa for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 180°C and formed cookie-shaped plates after cooling.

[0270] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N-butylamine was added to remove open NCO bonds. The mixture was heated to 110 °C. The sample dissolved completely, but gave a cloudy solution.

[0271] Recyclability test (solution, DMI). 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm). 3) and immersed in 30 mL of 1,3-dimethyl-2-imidazolidinone. 1 g of N-butylamine was added to remove open NCO bonds. The mixture was heated to 120 °C. The sample was completely dissolved after 1 h, giving a clear solution.

[0272] Example 13: Preparation of a covalently bonded adaptive network (CAN) poly(urea-urethane) polymer according to the present invention from 2-(ethylamino)ethanol 15.0 g (7.3% NCO) of the prepolymer described in Reference Example 4 and 1.10 g (12.8 mmol) of 2-(ethylamino)ethanol were added (molar ratio NCO:XH of 1.05:1.00, where X = the sum of O and N) and stirred at 2000 rpm in a speed mixer for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separating foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellow, opaque solid plate.

[0273] Recyclability test (melting): The obtained plate samples were cut into small cubes (0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed at 880 kPa for at least 5 minutes (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples began to melt around 150°C and formed cookie-shaped plates after cooling.

[0274] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N-butylamine was added to remove open NCO bonds. The mixture was heated to 110 °C. The sample did not dissolve, but it swelled.

[0275] Recyclability test (solution, DMI). 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm). 3The sample was cut into strips and immersed in 30 mL of 1,3-dimethyl-2-imidazolidinone. 1 g of N-butylamine was added to remove open NCO bonds. The mixture was heated to 120 °C. The sample was completely dissolved after 4 h, giving a clear solution.

[0276] Comparative Example 14: Preparation of Covalently Adaptable Network (CAN) Poly(urea-urethane) Polymer from 1,4-Butanediol 15.0 g (7.3% NCO) of the prepolymer described in Reference Example 4 and 1.12 g (12.4 mmol) of 1,4-butanediol were added (molar ratio NCO:XH 1.05:1.00, X=O), and the mixture was stirred at 2000 rpm in a speed mixer for 20 seconds. The mixture was poured into a silicone rubber mold lined with a separator foil and cured in a drying oven at 105 °C for 90 minutes. The material was obtained as a yellow, opaque solid plate.

[0277] Recyclability test (melting): The obtained plate sample was cut into a small cube (approximately 0.2 × 0.2 × 0.2 cm). 3 ) and transferred to a hot press. The samples were pressed for at least 5 minutes at a pressure of 880 kPa (20 kN force applied to a 17 cm diameter circular press according to the melting point analysis method described above). The samples did not melt up to a temperature of 180°C.

[0278] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N-butylamine was added to remove open NCO bonds. The mixture was heated to 110 °C. The sample did not dissolve.

[0279] Recyclability test (solution, DMI). 1 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm). 3The sample was cut into strips and immersed in 10 mL of 1,3-dimethyl-2-imidazolidinone. 0.33 g of N-butylamine was added to remove open NCO bonds. The mixture was heated to 120 °C. The sample did not dissolve even after 7 hours; the sample swelled in the solvent.

[0280] <Comparative Example 15: Preparation according to WO 2022189242> 16.5 g of pMDI was dissolved in THF and cooled to 0°C. DIB-MDA (20.23 g) in THF was added dropwise to the pMDI / THF solution under stirring. The reaction mixture was stirred at 0°C for 1 hour and then heated to gentle reflux for 6 hours. The solvent was removed and the sample was cured at 140°C for 24 hours. Product 15a was obtained as a yellow solid.

[0281] Recyclability test (solution, toluene). 3 g of solid 15a was cut into a small cube (0.2 × 0.2 × 0.2 cm). 3 The sample was cut into strips and immersed in 30 mL of toluene. The mixture was heated to 110°C for 4 hours. The sample did not dissolve.

[0282] 3 g of plate 15a was immersed in 30 mL of toluene and 0.9 g of 1,4-butanediol was added (2.00 equivalents of OH butanediol / 1 equivalent of HUB in the plate). The mixture was stirred under reflux for 24 hours. After this time, the material swelled but did not dissolve.

[0283] 3 g of 15a was cut into small pieces and soaked in a small amount of toluene (5 mL), and 0.4 g of diisopropylamine was added. The mixture was heated under reflux for 8 hours. The cubes dissolved, yielding a yellow liquid.

[0284] 3 g of plate 15a was immersed in 30 mL of toluene, and 0.4 g of DIB-MDA was added (0.25 equivalents of SHA DIB-MDA / 1 equivalent of HUB in the plate). The mixture was stirred under reflux overnight. Upon cooling, the mixture did not gel. The solvent was removed to give a viscous liquid that was still soluble in THF.

[0285] <Cited Document> - “Kunststoffhandbuch [Plastics handbook], volume 7, Polyurethane [Polyurethanes]”, Carl Hanser Verlag, 3rd edition 1993, chapter 3.1, 3.2 and 3.3.2. Ullmann’s Encyclopedia of Industrial Chemistry], 4th edition, volume 19, pp.62 - 65 - International Publication No. 2006 / 040159

Claims

1. A poly(urea-urethane) polymer comprising: The following ingredients (i) at least one isocyanate; (ii) at least one polyol; and (iii) at least one secondary amine having the following formula (I):

1. A poly(urea-urethane) polymer obtained or obtained by a process comprising the step of reacting: 【Chemistry 1】 (where, -R ７ , １２ , ５ , １ , ９ , １ , ３ , １ , １ , ３ , ｎ , ９ , １ , ９ , １０ , １ , ８ , ９ , １ , １ , ３ , １１ - is -Z １ -, -Z ２ -, -Z ３ -, -Z ４ -, -Z ５ -, -Z ６ -, -Z ７ -, -Z ７ -, -Z ８ -, -Z ９ -, -Z １０ -, -Z １１ -, -Z １３ -, -Z​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​ -Z １ - is a substituted or unsubstituted, straight or branched chain C １ ~C ３０ alkylene; -Z ２ - is a substituted or unsubstituted, straight or branched chain 2- to 300,000-membered heteroalkylene; -Z ３ - is a substituted or unsubstituted, straight or branched chain C ２ ~C ３０ alkenylene; -Z ４ - is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z ５ - is a substituted or unsubstituted C ５ ~C ３０ is cycloalkylene; -Z ６ - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z ７ - is a substituted or unsubstituted C ５ ~C ３０ is cycloalkenylene; -Z ８ - is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z ９ - is a substituted or unsubstituted C ６ ~C ３０ is arylene; -Z １０ - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z １１ - is a C substituted with -NHR or -OR ６ ~C ３０ arylene, where R is H and substituted or unsubstituted, linear or branched C １ ~C １０ selected from the group consisting of alkyl; -Z １２ - is -N(R ｆ )- and; -Z １３ - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z １３ At least one of the one or more heteroatoms in ａ Derived from; C ａ is a C atom or an H atom, and C ｂ is a C atom or an H atom, and C ａ and C ｂ at least one of which is a C atom; X ａ is an O atom or NH, and X ｂ is an O atom or NH, and X ａ and X ｂ at least one of X is NH; ａ and / or X ｂ When is NH, each C ａ and / or C ｂ is a C atom; where: (A)R ｃ , R ｄ , R ｆ , and R ｇ are each independently hydrogen, a straight or branched chain, substituted or unsubstituted C １ ~C ３０ Alkyl, straight or branched chain substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted straight-chain or branched-chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight-chain or branched-chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C ５ ~C ３０ Cycloalkyl, substituted or unsubstituted C ５ ~C ３０ Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C ６ ~C ３０ Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C １ ~C １０ Alkylene C ５ ~C ３０ Cycloalkyl, substituted or unsubstituted C １ ~C １０ Alkylene C ５ ~C ３０ Cycloalkenyl, substituted or unsubstituted C １ ~C １０ Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C １ ~C １０ alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C １ ~C １０ Alkylene C ６ ~C ３０ Aryl and substituted or unsubstituted C １ ~C １０ alkylene 5- to 30-membered heteroaryl; R ｂ and R ｅ are each independently R ｃ , R ｄ , R ｆ , and R ｇ is defined as; or R ｂ and R ｅ does not exist, and C ａ and C ｂ are bonded to each other via a single bond, and C ａ , C ｂ , X ａ , X ｂ , and R ａ forming a heterocyclic ring consisting of or (B) C ａ and R ｅ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｆ and R ｇ does not exist; and C ｂ and R ｂ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｃ and R ｄ Neither of these exists; or (C)-C ａ and R ｅ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｆ and R ｇ does not exist; or - C ｂ and R ｂ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｃ and R ｄ Neither of these exists; Here, C ａ and R ｅ is substituted or unsubstituted C ６ ~C ３０ When forming an arylene, R ｂ , R ｃ , and R ｄ are each independently R under (A). ｃ , R ｄ , R ｆ , and R ｇ is defined as any one of: Here, C ｂ and R ｂ is substituted or unsubstituted C ６ ~C ３０ When forming an arylene, R ｅ , R ｆ , and R ｇ are each independently R under (A). ｃ , R ｄ , R ｆ , and R ｇ (defined as one of the following:

2. X ａ is NH, and X ｂ is NH, and the secondary amine (iii) is of the following formula (II): 【Chemistry 2】 (In the formula, C ａ , C ｂ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , and -R ａ - is as defined in formula (I).

2. The poly(urea-urethane) polymer of claim 1, having

3. -R ａ -ga, -Z １ -, -Z ２ -, -Z ５ -, -Z ９ -, -Z １０ -, -Z １ -Z ５ -, -Z ５ -Z １ -Z ５ -, -Z ９ -Z １ -Z ９ -, -Z １ -Z ５ -Z １ -, -Z １ -Z ９ -Z １ - and -Z ９ -Z １ (-Z １１ -Z １ ) ｎ -Z ９ 3. The poly(urea-urethane) polymer of claim 1, wherein n is selected from the group consisting of: - (n=1, 2, 3, 4, 5, or 6).

4. R ｃ , R ｄ , R ｆ , and R ｇ are each independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl, and —C(OH)H—R ｋ is selected from the group consisting of Here, R ｋ is hydrogen, straight or branched chain substituted or unsubstituted C １ ~C ３０ Alkyl, straight or branched chain substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted straight-chain or branched-chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight-chain or branched-chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C ５ ~C ３０ Cycloalkyl, substituted or unsubstituted C ５ ~C ３０ Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C ６ ~C ３０ Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C １ ~C １０ Alkylene C ５ ~C ３０ Cycloalkyl, substituted or unsubstituted C １ ~C １０ Alkylene C ５ ~C ３０ Cycloalkenyl, substituted or unsubstituted C １ ~C １０ Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C １ ~C １０ alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C １ ~C １０ Alkylene C ６ ~C ３０ Aryl, and substituted or unsubstituted C １ ~C １０ The poly(urea-urethane) polymer of any one of claims 1 to 3, selected from the group consisting of alkylene 5- to 30-membered heteroaryl.

5. R ｂ and R ｅ are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl.

6. R ｂ , R ｃ , and R ｄ is H, and R ｅ , R ｆ , and R ｇ is H; R ｂ , R ｃ , and R ｄ One of the groups other than H is CH ３ and R ｅ , R ｆ , and R ｇ One of the groups other than H is CH ３ 6. The poly(urea-urethane) polymer of claim 1, wherein

7. R ｂ , R ｃ , and R ｄ is an ethyl group, and R ｅ , R ｆ , and R ｇ The poly(urea-urethane) polymer of any one of claims 1 to 6, wherein any one of is an ethyl group.

8. The poly(urea-urethane) polymer of any one of claims 1 to 7, wherein the at least one secondary amine (iii) is 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA).

9. 8. The poly(urea-urethane) polymer of any one of claims 1 to 7, wherein the at least one secondary amine (iii) is DIB-butanediamine (N,N'-di-sec-butyl-1,4-butanediamine).

10. The at least one secondary amine (iii) has the following formula: CH ３ -CH ２ -CH(CH ３ )-NH-[CH(CH ３ )-CH ２ -O] ｍ１ -CH ２ -C(R ｘ１ ) (R ｙ１ )-CH ２ -[O-CH ２ -CH(CH ３ )] ｏ１ -NH-CH(CH ３ )-CH ２ -CH ３ (In the formula, R ｘ１ is -CH ２ -CH ３ and R ｙ１ is -CH ２ -[O-CH ２ -CH(CH ３ )] ｎ１ -NH-CH(CH ３ )-CH ２ -CH ３ and m1+n1+o1 is in the range of 5 to 6.

11. 11. The poly(urea-urethane) polymer according to any one of claims 1 to 10, wherein the at least one isocyanate (i) is selected from the group consisting of monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), mixtures of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), tolylene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, xylene 2,6-diisocyanate, naphthylene 1,5-diisocyanate (1,5-NDI), butane 1,4-diisocyanate, pentane 1,5-diisocyanate (PDI), hexane 1,6-diisocyanate (HDI), octane 1,8-diisocyanate, nonane 1,9-diisocyanate, decane 1,10-diisocyanate, 2,2-dimethylpentane 1,5-diisocyanate, 2-methylpentane 1,5-diisocyanate (MPDI), 2,4,4 (or 2,2,4)-trimethylhexane 1,6-diisocyanate (TMDI), cyclohexane 1,3- and 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), methylene-bis(cyclohexyl isocyanate) (H12 mDI), 2,4- or 2,6-diisocyanato-1-methylcyclohexane (H6TDI), 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane (AMCI), 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane-4,4',4"-triisocyanate, toluene-2,4,6-triyl Triisocyanate, ethyl ester 1-lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, triisocyanatomethylcyclohexane, 1,8-diisocyanato-4-(isocyanatomethyl)octane, undecane 1,6,11-triisocyanate, 1,7-diisocyanato-4-(3-isocyanatopropyl)heptane, 1,6-diisocyanato-3-(isocyanatomethyl)hexane, 2,2-bis[[4-(isocyanatomethyl)phenyl]methyl]butyl n-[[4-(isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)tris(hexamethylene)isocyanate, 1,3,5-triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3"-[(1h,3h,5h)-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyltris(methylene)] A poly(urea-urethane) polymer selected from the group consisting of thris[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanato-dicyclohexylmethane, triisocyanatotriphenylthiophosphate, 2,4,4'-diphenyl ether triisocyanate, 1,3-bis(3-isocyanato-4-methylphenyl)-1,3-diazetidine-2,4-dione, and mixtures of two or more thereof.

12. 12. The poly(urea-urethane) polymer of any one of claims 1 to 11, wherein the at least one polyol (i) is selected from the group consisting of polyester polyols, polyetherester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols, and mixtures of two or more thereof.

13. A poly(urea-urethane) polymer-based composite material, comprising: The following ingredients (i) at least one isocyanate; (ii) at least one polyol; and (iii) at least one secondary amine having formula (I): to obtain a mixture comprising a poly(urea-urethane) polymer, preferably a poly(urea-urethane) polymer according to any one of claims 1 to 11; The resulting mixture was mixed with the following (iv): (iv) a filler selected from the group consisting of glass fibers, carbon fibers, mineral fibers, fabrics, metal mesh, metal fibers, metal rods, carbonates, wood, and mixtures of two or more thereof; and contacting the Composite material based on poly(urea-urethane) polymers, obtained or obtained by a process comprising: 【Transformation 3】 (where, -R ａ - is, -Z １ -, -Z ２ -, -Z ３ -, -Z ４ -, -Z ５ -, -Z ６ -, -Z ７ -, -Z ７ -, -Z ８ -, -Z ９ -, -Z １０ -, -Z １１ -, -Z １３ -, -Z １ -Z ５ -, -Z ５ -Z １ -Z ５ -, -Z １ -Z ６ -, -Z １ -Z ７ -, -Z １ -Z ８ -, -Z １ -Z ９ -, -Z ９ -Z １ -Z ９ -, -Z １ -Z １０ -, -Z ３ -Z ５ -, -Z ３ -Z<000035​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​ -Z １ - is a substituted or unsubstituted, straight or branched chain C １ ~C ３０ alkylene; -Z ２ - is a substituted or unsubstituted, straight or branched chain 2- to 300,000-membered heteroalkylene; -Z ３ - is a substituted or unsubstituted, straight or branched chain C ２ ~C ３０ alkenylene; -Z ４ - is a substituted or unsubstituted, straight or branched chain, 3- to 30-membered heteroalkenylene; -Z ５ - is a substituted or unsubstituted C ５ ~C ３０ is cycloalkylene; -Z ６ - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z ７ - is a substituted or unsubstituted C ５ ~C ３０ is cycloalkenylene; -Z ８ - is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z ９ - is a substituted or unsubstituted C ６ ~C ３０ is arylene; -Z １０ - is a substituted or unsubstituted 5- to 30-membered heterocycloarylene; -Z １１ - is a C substituted with -NHR or -OR ６ ~C ３０ arylene, where R is H and substituted or unsubstituted straight or branched chain C １ ~C １０ selected from the group consisting of alkyl; -Z １２ - is -N(R ｆ )- and; -Z １３ - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where Z １３ At least one of the one or more heteroatoms in ａ Derived from; C ａ is a C atom or an H atom, and C ｂ is a C atom or an H atom, and C ａ and C ｂ at least one of which is a C atom; X ａ is an O atom or NH, and X ｂ is an O atom or NH, and X ａ and X ｂ at least one of X is NH; ａ and / or X ｂ When is NH, each C ａ and / or C ｂ is a C atom; where: (A)R ｃ , R ｄ , R ｆ , and R ｇ are each independently hydrogen, straight or branched chain substituted or unsubstituted C １ ~C ３０ Alkyl, straight or branched chain substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted straight-chain or branched-chain 2- to 30-membered heteroalkyl, substituted or unsubstituted straight-chain or branched-chain 3- to 30-membered heteroalkenyl, substituted or unsubstituted C ５ ~C ３０ Cycloalkyl, substituted or unsubstituted C ５ ~C ３０ Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C ６ ~C ３０ Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C １ ~C １０ Alkylene C ５ ~C ３０ Cycloalkyl, substituted or unsubstituted C １ ~C １０ Alkylene C ５ ~C ３０ Cycloalkenyl, substituted or unsubstituted C １ ~C １０ Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C １ ~C １０ alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C １ ~C １０ Alkylene C ６ ~C ３０ Aryl and substituted or unsubstituted C １ ~C １０ alkylene 5- to 30-membered heteroaryl; R ｂ and R ｅ are mutually independent R ｃ , R ｄ , R ｆ , and R ｇ is defined as; or R ｂ and R ｅ does not exist, and C ａ and C ｂ are bonded to each other via a single bond, and C ａ , C ｂ , X ａ , X ｂ and R ａ forming a heterocyclic ring consisting of or (B) C ａ and R ｅ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｆ and R ｇ does not exist; and C ｂ and R ｂ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｃ and R ｄ Neither of these exists; or (C)-C ａ and R ｅ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｆ and R ｇ does not exist; or - C ｂ and R ｂ is a substituted or unsubstituted C ６ ~C ３０ Form an arylene, R ｃ and R ｄ Neither of these exists; Here, C ａ and R ｅ is substituted or unsubstituted C ６ ~C ３０ When forming an arylene, R ｂ , R ｃ , and R ｄ are each independently (A) under R ｃ , R ｄ , R ｆ , and R ｇ is defined as any one of: Here, C ｂ and R ｂ is substituted or unsubstituted C ６ ~C ３０ When forming an arylene, R ｅ , R ｆ , and R ｇ are each independently (A) under R ｃ , R ｄ , R ｆ , and R ｇ (defined as one of the following:

14. A process for producing the poly(urea-urethane) polymer of any one of claims 1 to 12, comprising the steps of: (a) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; (b) contacting the prepolymer obtained in (a) with at least one secondary amine, wherein the at least one secondary amine has the formula (I) according to any one of claims 1 to 10, to obtain the poly(urea-urethane) polymer; or (a') reacting at least one isocyanate (i) with at least one secondary amine, said at least one secondary amine having the formula (I) according to any one of claims 1 to 10, to obtain a prepolymer; (b') contacting the prepolymer obtained in (a') with at least one polyol (ii) to obtain the poly(urea-urethane) polymer. A method comprising:

15. Use of the poly(urea-urethane) polymer according to any one of claims 1 to 12 or the poly(urea-urethane) polymer composite according to claim 13 as a recyclable material.

16. A recyclable article comprising the poly(urea-urethane) polymer of any one of claims 1 to 12 or the poly(urea-urethane) polymer composite of claim 13.

17. A process for molding a poly(urea-urethane) polymer according to any one of claims 1 to 12 or a poly(urea-urethane) polymer composite obtained or obtained by the process according to claim 13, comprising the steps of: shaping the poly(urea-urethane) polymer, the shaping of the polymer comprising: (x) applying pressure and heat to the poly(urea-urethane) polymer to obtain a molded body; or (x') extruding the poly(urea-urethane) polymer to obtain a molded article. A method comprising:

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