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

Abstract

The present invention relates to a poly (urea-urethane) polymer, a poly (urea-urethane) polymer composite, a method for preparing the polymer and the composite. Furthermore, the present invention relates to a method of shaping the polymer and the use of the polymer and its composites as repairable and recyclable materials.

Description

[0001] The present invention relates to poly(urea - urethane) polymers, poly(urea - urethane) polymer composites, methods for preparing the polymers and the composites. Further, the present invention relates to methods of shaping the polymers and the use of the polymers and their composites as repairable and recyclable materials.

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

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

[0004] Therefore, there is a need to provide a new polymer. Thus, an object of the present invention is to provide a new polymer, in particular a poly(urea - urethane) polymer, obtained from isocyanates, amines, and polyols, which can be used in composites and is readily repairable and recyclable.

[0005] Surprisingly, it has been found that the polymers according to the present invention allow for the production of composites that can be used in many applications while being readily repairable and recyclable. In fact, the poly(urea - urethane) polymers according to the present invention have dynamic hindered urea bonds (HUBs) that act as dynamic covalent bonds in covalent adaptable systems / networks (CAS / CANs). Thus, it is thought that the introduction of bulky substituents to the nitrogen atoms weakens the bond such that there is a dissociation equilibrium between open and closed bonds, which is shifted to the open side by increasing the temperature. The HUBs split into the original constituent groups (depolymerization). The claimed materials are readily processable by thermomechanical processing methods as shown below and facilitate the chemical and mechanical recycling of the poly(urea - urethane) polymers.

[0006] Accordingly, the present invention relates to a poly(urea - urethane) polymer obtainable or obtained by a method comprising the following:

[0007] - reacting the following components:

[0008] (i) At least one isocyanate;

[0009] (ii) At least one polyol; and

[0010] (iii) At least one secondary amine having the following formula (I):

[0011]

[0012] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 - where n = 1, 2, 3, 4, 5, or 6 - and -Z1-Z 12 -Z1-; wherein

[0013] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0014] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0015] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0016] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0017] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0018] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0019] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0020] -Z8- is a substituted or unsubstituted 5- to 30-membered heteroalkenyl;

[0021] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0022] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroaryl;

[0023] -Z 11 - is an arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10

[0024] -Z 12 - is -N(R f )-;

[0025] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heteroalkyl, where at least one of one or more heteroatoms of Z 13 is from X a ;

[0026] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0027] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b being NH, the corresponding C a and / or C b is a C atom;

[0028] where

[0029] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 ​Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0030] R b and R e are each independently as defined for R c , R d , R f and R g ; or

[0031] There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or

[0032] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and

[0033] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both; or

[0034] (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and without R f and R g both; or

[0035] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and without R c and R d both;

[0036] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in any one of (A);

[0037] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A).

[0038] Preferably, the at least one secondary amine (iii) has the following formula (I)

[0039]

[0040] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10-, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9——where n = 1, 2, 3, 4, 5, or 6——and -Z1-Z 12 -Z1; where

[0041] -Z1 is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0042] -Z2 is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0043] -Z3 is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0044] -Z4 is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0045] -Z5 is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0046] -Z6 is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0047] -Z7 is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0048] -Z8 is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene;

[0049] -Z9 is a substituted or unsubstituted C6-C 30 arylene;

[0050] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene;

[0051] -Z 11 - is a C6-C arylene substituted by -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10

[0052] -Z 12 - is -N(R f )-;

[0053] -Z 13 ​- is a substituted or unsubstituted 5- to 30-membered heteroalkyl ring, wherein 13 at least one of the one or more heteroatoms of a is from X

[0054] wherein C a is a C atom or an H atom and C b is a C atom or an H atom, wherein C a and C b at least one of them is a C atom;

[0055] wherein X a is an O atom or NH and X b is an O atom or NH, wherein X a and X b at least one of them is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0056] wherein

[0057] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heteroalkyl ring, substituted or unsubstituted 5- to 30-membered heteroalkenyl ring, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroalkyl ring, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroalkenyl ring, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C10 an alkylene 5- to 30-membered heteroaryl,

[0058] R b and R e are each independently as defined for R c 、R d 、R f and R g ; or

[0059] there is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a 、C b 、X a 、X b and R a ; or

[0060] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and there is no R f and R g both; and

[0061] C b and R b form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and there is no R c and R d both.

[0062] Preferably, each of C a and C b is a C atom.

[0063] Preferably, X a is NH, X b is NH, and the secondary amine (iii) has the following formula (II)

[0064]

[0065] wherein C a 、C b 、R b 、R c 、R d 、R e 、R f 、R g and -R a - are as defined in formula (I).

[0066] Preferably, -R a- selected from the group consisting of: -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z9-Z1-Z9-, -Z1-Z5-Z1-, -Z1-Z9-Z1- and -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6, preferably selected from the group consisting of: -Z2-, -Z9-Z1-Z9- and -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6, more preferably selected from the group consisting of: -Z2- and -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6.

[0067] Preferably, -Z1- is selected from the group consisting of: -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH2-CH(CH2CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8- and -(CH2) 10 -.

[0068] Preferably, when R a is selected from the group consisting of: -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9- (where n = 1, 2, 3, 4, 5, or 6) and -Z1-Z 12 -Z1-, -Z1- is -CH2-.

[0069] Preferably, -Z9- is selected from the group consisting of phenylene, naphthylene, biphenylene, fluorenylene and indenyl, where -Z9- is more preferably phenylene. Preferably, phenylene is selected from the group consisting of ortho-phenylene, meta-phenylene and para-phenylene, more preferably ortho-phenylene and para-phenylene.

[0070] Preferably, -R a - is -Z9-Z1-Z9-, where -Z9- is phenylene, more preferably p-phenylene, and -Z1- is -CH2-.

[0071] Preferably, -R a - is -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6, where -Z9- is phenylene and -Z1- is -CH2-, and where -Z 11 - is a C6-arylene substituted with -NHR.

[0072] Preferably, in -Z 11 -, R is -C(R h )(R i )(R j ), where R h , R i and R j are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl. More preferably, R h , R i and R jEach is independently selected from the group consisting of: hydrogen, linear 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-pinan-1-yl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of: hydrogen, methyl, and ethyl, more preferably selected from the group consisting of: hydrogen, methyl, and ethyl. More preferably, any one of R h , R i and R j is H, and except for the one that is H, R h , R i and R j one of them is CH3. More preferably, except for the one that is CH3 or H, R h , R i and R j one of them is ethyl.

[0073] Alternatively, preferably, in -Z 11 -, R is -C(R h )(R i )(R j ), where C and R h form a substituted or unsubstituted C6-C 30 arylene, and not both R i and R j . For example, -Z 11 - can be -NH-Ph.

[0074] In the context of the present invention, preferably, -Z2- is a substituted or unsubstituted, linear or branched 2-membered to 500-membered heteroalkylene, more preferably a substituted or unsubstituted, linear or branched 2-membered to 35-membered heteroalkylene, more preferably a substituted or unsubstituted, linear or branched 2-membered to 30-membered heteroalkylene.

[0075] More preferably, -Z2- is selected from the group consisting of: -CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(where R x1 is -CH2-CH3, where R y1 is [-O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n )(where m1 + n1 + o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C(R l )(R m )(R n )(and where m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O] o3-CH2-CH(CH)3- (where n3 is in the range of 8 to 10 and m3 + o3 is in the range of 3 to 4, or where n3 is in the range of 12 to 13 and m3 + o3 is in the range of 5 to 7, or where n3 is in the range of 38 to 40 and m3 + o3 is in the range of 5 to 7), -[CH-CH2-O] m4 -CH2-CH2- (where m4 is in the range of 8 to 250), and -[CH2-CH2-NH] m5 - (where m5 is in the range of 10 to 100,000).

[0076] 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, where 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.

[0077] Preferably, in one or more of R y1 and R y2 , R l , R m and R n are independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl. More preferably, R l 、R m and R n are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl. More preferably, R l 、R m and R n are each independently selected from the group consisting of: hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-1-yl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, 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, any one of R l 、R m and R n is H, and except for the one that is H, one of R l 、R m and R n is CH3. More preferably, except for the one that is CH3 or H, one of R l 、R m and R n is ethyl. Alternatively, preferably, in one or more of R y1 and R y2 , C and R l form a substituted or unsubstituted C6-C 30 arylene, and there is no R m and R n both. For example, R y1 can be -CH2-[O-CH2-CH(CH3)] n1 -NH-Ph, and R y2 can be [-O-CH2-CH(CH3)] n2 -NH-Ph.

[0078] Preferably, -Z3- is selected from the group consisting of: -CH=CH- and -CH2-CH=CH-.

[0079] Preferably, -Z4- is selected from the group consisting of: -CH=CH-NH-, -CH=CH-O-, -CH=CH-CH2-O-.

[0080] Preferably, -Z5- is selected from the group consisting of cyclohexane-1,4-diyl, cyclohexane-1,3-diyl, and 2,6-diyl-norbornane.

[0081] Preferably, -Z6- is selected from the group consisting of 1,5-dioxaoctylene and 4,8-dioxabicyclo[3.3.0]octylene.

[0082] Preferably, -Z7- is selected from the group consisting of cyclopent-1,2-ene-3,5-diyl, 3-cyclohexene-1,2-diyl, 2,5-cyclohexadiene-1,4-diyl, cyclohex-1,2-ene-3,5-diyl, 2,5-cyclohexadiene-1,4-diyl, and cyclohept-1,2-ene-3,5-diyl.

[0083] Preferably, -Z 10 - is a triazinyl group, more preferably one or more of vic-triazinylene, asym-triazinylene, and sym-triazinylene.

[0084] Preferably, R c 、R d 、R f and R g are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-1-yl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl, and -C(OH)H-R k , more preferably selected from the group consisting of hydrogen, methyl, and ethyl, even more preferably selected from the group consisting of hydrogen, methyl, and ethyl,

[0085] wherein R k is selected from the group consisting of hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl.

[0086] 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.

[0087] Preferably, any one of R b , R c and R d is H, and any one of R e , R f and R g is H; except for the one that is H, one of R b , R c and R d is CH3, and except for the one that is H, one of R e , R f and R g is CH3.

[0088] Preferably, R b , R c and Rd any one of which is ethyl, and R e , R f and R g any one of which is ethyl; more preferably

[0089] except for the one that is ethyl, R b , R c and R d one of them is H,

[0090] except for the one that is ethyl, R e , R f and R g one of them is H,

[0091] except for the one that is ethyl or H, R b , R c and R d one of them is CH3, and

[0092] except for the one that is ethyl or H, R e , R f and R g one of them is CH3.

[0093] Preferably, the at least one secondary amine (iii) is

[0094] 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA).

[0095] 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, where R x1 is -CH2-CH3, where 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.

[0096] Preferably, the at least one secondary amine (iii) is

[0097] DIB-polyetheramine T403, where m1 + n1 + o1 = 5 to 6.

[0098] Alternatively, preferably, the at least one secondary amine (iii) is DIB-butylenediamine (N,N'-di-sec-butyl-1,4-butanediamine).

[0099] Alternatively, preferably, the at least one secondary amine (iii) is 2-(ethylamino)ethanol.

[0100] In the context of the present invention, suitable isocyanates are known per se to the person skilled in the art.

[0101] Preferably, the at least one isocyanate (i) has an NCO functionality of 2 or greater, more preferably 2 or 3.

[0102] Preferably, the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3 or greater, more preferably, the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3.

[0103] 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), toluene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, xylene 2,6 - diisocyanate, naphthalene 1,5 - diisocyanate (1,5 - NDI), butane 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), octane 1,8 - diisocyanate, nonane 1,9 - diisocyanate, decane 1,10 - diisocyanate, 2,2 - dimethylpentane 1,5 - diisocyanate, 2 - methylpentane 1,5 - diisocyanate (MPDI), 2,4,4(or 2,2,4) - trimethylhexane 1,6 - diisocyanate (TMDI), cyclohexane 1,3 - and 1,4 - diisocyanate, 1 - isocyanato - 3,3,5 - trimethyl - 5 - isocyanatomethylcyclohexane (IPDI), methylene - bis(isocyanatocyclohexane) (H12MDI), 2,4 - or 2,6 - diisocyanato - 1 - methylcyclohexane (H6TDI), 1 - isocyanato - 1 - methyl - 4(3) - isocyanatomethylcyclohexane (AMCI), 1,3 - bis(isocyanatomethyl)cyclohexane, 1,4 - bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane - 4,4',4" - triisocyanate, toluene - 2,4,6 - triyltriisocyanate, ethyl ester 1 - lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, triisocyanatomethylcyclohexane, 1,8 - diisocyanato - 4 - (isocyanatomethyl)octane, undecane 1,6,11 - triisocyanate, 1,7 - diisocyanato - 4 - (3 - isocyanatopropyl)heptane, 1,6 - diisocyanato - 3 - (isocyanatomethyl)hexane, 2,2 - bis[[4 - (isocyanatomethyl)phenyl]methyl]butyl n - [[4 - (isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6 - trioxotriazine - 1,3,5(2h,4h,6h) - triyl) tris(hexamethylene) isocyanate, 1,3,5 - triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3" - [(1h,3h,5h) - 2,4,6 - trioxo - 1,3,5 - triazine - 1,3,5 - triyltri(methylene)] tris[3,5,5 - trimethylcyclohexyl] triisocyanate, 1,3,5 - triazine - 2,4,6 - triisocyanate, 2,4,4' - triisocyanato - dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4' - diphenyl ether triisocyanate, 1,3 - bis(3 - isocyanato - 4 - methylphenyl) - 1,3 - diazetidine - 2,4 - dione and mixtures of two or more thereof,

[0104] More preferably, it is selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), naphthalene 1,5 - diisocyanate (1,5 - NDI), 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), methylene - bis(cyclohexyl isocyanate) (H12MDI), such as dicyclohexylmethane 4,4'- or 2,4'- or 2,2'-diisocyanate, and mixtures of two or more thereof.

[0105] Preferably, the at least one isocyanate (i) is selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and toluene diisocyanate (TDI).

[0106] Preferably, the at least one isocyanate (i) is selected from the group consisting of methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), and a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI); more preferably, it is selected from the group consisting of monomeric methylene diphenyl diisocyanate (mMDI) and a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI).

[0107] More preferably, the toluene diisocyanate (TDI) contains one or more of 2,4 - TDI and 2,6 - TDI, and is more preferably composed of them.

[0108] More preferably, the monomeric methylene diphenylene diisocyanate (mMDI) comprises, more preferably consists of, one or more of 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene(diphenyl diisocyanate) (2,2'-MDI) and 2,4'-methylene(diphenyl diisocyanate) (2,4'-MDI), more preferably 4,4'-methylene(diphenyl diisocyanate) (4,4'-MDI). More preferably, the at least one isocyanate (i) is monomeric methylene diphenylene diisocyanate (mMDI), which comprises, more preferably consists of, one or more of 4,4'-methylene (diphenyl diisocyanate) (4,4'-MDI), 2,2'-methylene (diphenyl diisocyanate) (2,2'-MDI) and 2,4'-methylene (diphenyl diisocyanate) (2,4'-MDI), more preferably 4,4'-methylene (diphenyl diisocyanate) (4,4'-MDI).

[0109] Other possible isocyanates are mentioned, for example, in “Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes] Polyurethane [Polyurethane]”, Carl Hanser Verlag, 3rd edition, 1993, Chapters 3.2 and 3.3.2.

[0110] Suitable polyols are known per se to the person skilled in the art.

[0111] In principle, any polyol conventionally used for preparing polyurethane can be used as polyol.The type of polyol can depend on the desired application purpose.Suitable polyol is polyester polyol, especially including aliphatic polyester polyol and aliphatic aromatic polyester polyol, polyester carbonate polyol, polyether ester polyol, aliphatic polycarbonate polyol, polyacrylate polyol, polyolefin polyol, aliphatic polyether alcohol and mixture thereof.Preferably, this at least one polyol is selected from polyester polyol, particularly aliphatic polyester polyol and aliphatic aromatic polyester polyol, aliphatic polycarbonate polyol, aliphatic polyether alcohol and mixture thereof.Especially, this at least one polyol comprises polyester polyol and / or aliphatic polyether polyol as described herein.Especially, this at least one polyol is selected from polyester polyol, aliphatic polyether polyol and combination thereof.

[0112] 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.

[0113] More preferably, the at least one polyol (i) is selected from the group consisting of polyester polyols and polyether polyols.

[0114] Suitable polyester polyols for use as polyols are, in particular, aliphatic polyester alcohols and aliphatic / aromatic polyester alcohols, i.e., polyester alcohols based on a dicarboxylic acid component selected from aliphatic dicarboxylic acids, cycloaliphatic dicarboxylic acids, aromatic dicarboxylic acids and combinations thereof and a diol component selected from aliphatic diols, cycloaliphatic diols and polyether polyols.

[0115] Suitable aliphatic diols for the preparation of polyester polyols generally have from 2 to 20 C atoms, in particular from 3 to 10 C atoms. Examples of aliphatic diols are ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,2-diol, butane-1,3-diol, butane-1,4-diol, butane-2,3-diol, pentane-1,2-diol, pentane-1,3-diol, pentane-1,4-diol, pentane-1,5-diol, pentane-2,3-diol, pentane-2,4-diol, hexane-1,2-diol, hexane-1,3-diol, hexane-1,4-diol, hexane-1,5-diol, hexane-1,6-diol, hexane-2,5-diol, heptane-1,2-diol, 1,7-heptanediol, 1,8-octanediol, 1,2-octanediol, 1,9-nonanediol, 1,2-decanediol, 1,10-decanediol, 1,2-dodecanediol, 1,12-dodecanediol, 1,5-hexadiene-3,4-diol, neopentyl glycol, (2,2-dimethylpropane-1,3-diol), 2,2-diethylpropane-1,3-diol, 2-methyl-2-ethylpropane-1,3-diol, 2-methyl-2,4-pentanediol, 2,4-dimethyl-2,4-pentanediol, 2-ethyl-1,3-hexanediol, 2,5-dimethyl-2,5-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, pinacol, diethylene glycol, triethylene glycol, dipropylene glycol and tripropylene glycol

[0116] Suitable alicyclic diols for the preparation of polyester polyols generally have 4 to 20 C atoms, in particular 5 to 10 C atoms. Examples of alicyclic diols are cyclopentanediol, cyclohexane-1,4-diol, cyclohexane-1,2-dimethanol, cyclohexane-1,3-dimethanol, cyclohexane-1,4-dimethanol and 2,2,4,4-tetramethylcyclobutane-1,3-diol. Further suitable diols for the preparation of polyester polyols are polyether diols, in particular polyethylene glycol HO(CH2CH2O)n-H, higher polypropylene glycol HO(CH[CH3]CH2O)n-H (where n is an integer and n≥4, for example, 4 to 20), and polyethylene glycol-polypropylene glycol, more particularly those having 4 to 20 repeating units, the sequence of ethyleneoxy and propyleneoxy units can be block or random, and polytetramethylene glycol, more particularly those having 4 to 20 repeating units, and poly-1,3-propanediol, more particularly those having 4 to 20 repeating units.

[0117] Preferred dicarboxylic acids for the preparation of polyester polyols are aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid, alicyclic dicarboxylic acids preferably having 8 to 12 carbon atoms such as tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexanedicarboxylic acid, and aliphatic dicarboxylic acids preferably having 3 to 40 carbon atoms such as malonic acid, succinic acid, 2-methylsuccinic acid, glutaric acid, 2-methylglutaric acid, 3-methylglutaric acid, α-ketoglutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, brassylic acid, fumaric acid, 2,2-dimethylglutaric acid, suberic acid, diglycolic acid, oxaloacetic acid, glutamic acid, aspartic acid, itaconic acid and maleic acid and dimer fatty acids such as dimer fatty acids of octadecadienoic acid or dimer fatty acids obtained by dimerization of other polyunsaturated fatty acids or fatty acid mixtures [CAS 61788-89-4].

[0118] The dicarboxylic acids for the preparation of polyester polyols can be free acids or their ester-forming derivatives. The derivatives are preferably understood to be the corresponding acid anhydrides, monoalkyl esters and dialkyl esters, preferably mono- and di-C1-C4 alkyl esters, more preferably monomethyl esters and dimethyl esters, and also the corresponding monoethyl esters and diethyl esters, and additionally mono-vinyl esters and di-vinyl esters, and also mixed esters, examples being mixed esters having different C1-C4 alkyl components.

[0119] Among the polyester polyols, preferred are polyester polyols based on a diol component selected from the group consisting of butanediol, neopentyl glycol, hexanediol, ethylene glycol, diethylene glycol and mixtures thereof and a dicarboxylic acid component selected from the group consisting of adipic acid, phthalic acid, isophthalic acid and combinations thereof. Particularly preferred are polyester polyols based on butanediol and / or neopentyl glycol and / or hexanediol and adipic acid and / or phthalic acid and / or isophthalic acid.

[0120] Suitable polyester polyols for use as polyols also include polycaprolactones, especially poly-C4-C12-caprolactones, in particular polycaprolactone (PCL). Polycaprolactones refer to aliphatic polyesters obtainable by ring-opening polymerization of lactones, especially C4-C12-lactones, in particular ε-caprolactone. Polycaprolactone has a repeating monomer unit of the general formula [-O-CHR-(CH2) m -CO-], where m is from 4 to 10, m = 4 in the case of caprolactone, and R is hydrogen. In the context of the present invention, the term polycaprolactone is understood to mean both homopolymers of ε-caprolactone and copolymers of ε-caprolactone. Suitable copolymers are, for example, copolymers of ε-caprolactone with monomers selected from the group consisting of lactic acid, lactide, glycolic acid, and glycolide. Polyester polyols are conventional components, which are known, for example, from Ullmanns der technischen Chemie [Encyclopedia of Industrial Chemistry], 4th edition, volume 19, pages 62 to 65.

[0121] Suitable aliphatic polyether polyols for use as polyols are, for example, addition products of C2-C4-alkylene oxides such as ethylene oxide, propylene oxide, 1,2-epoxybutane, 2,3-epoxybutane, or 2-methyloxirane. Further suitable polymeric polyols are aliphatic polyether polyols obtainable by condensation of polyaliphatic alcohols, aliphatic polyether polyols obtained by alkoxylation of aliphatic polyols, amines, and amino alcohols. Suitable polyols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, trimethylolpropane, glycerol, pentaerythritol, triethanolamine (= tris(2-hydroxyethyl)amine), sorbitol, or mixtures thereof. Suitable polyether alcohols generally have an OH functionality in the range from 1.5 to 3.0, especially in the range from 1.8 to 2.5. Suitable polyether alcohols preferably have an OH value in the range from 20 to 300 mg KOH / g, and especially in the range from 30 to 250 mg KOH / g. In the context of the present invention, unless otherwise stated, the OH value is measured according to EN ISO 4629-1:2016.

[0122] Generally, they have a number-average molecular weight Mn in the range from 400 to 10,000 g / mol, preferably in the range from 500 to 5,000 g / mol, as determined by gel permeation chromatography as described above. Preferred polyether components are polyethylene oxide polyols, polypropylene oxide polyols, and polytetramethylene oxide polyols (poly-THF) having a molecular weight Mn of 400 to 10,000 g / mol, preferably 500 to 5,000 g / mol. In this case, polyether polyols with a particularly low molecular weight can be water-soluble in the case of a correspondingly high OH content.

[0123] Preferably, the at least one polyol (ii) is a polyether polyol, and the polyether polyol is more preferably selected from the group consisting of: polytetrahydrofuran, trifunctional polyether polyols containing secondary hydroxyl groups, polypropylene glycol, sucrose-based polyether polyols, tetrafunctional polyether polyols based on ethylenediamine and propylene oxide, and mixtures of two or more thereof, and more preferably selected from the group consisting of: polytetrahydrofuran and trifunctional polyether polyols containing secondary hydroxyl groups.

[0124] Preferably, the at least one polyol (ii) is a polyether polyol, and the polyether polyol is more preferably selected from the group consisting of: polytetrahydrofuran (f = 2, Mn = 2000 g / mol, OH = 56 mg KOH / g), trifunctional polyether polyols containing secondary hydroxyl groups (f = 3, Mn = 3500 g / mol, OH = 48, viscosity (25 °C) = 600 mPa·s; or f = 3, Mn = 3000 g / mol, OH = 53 mg KOH / g, viscosity (25 °C) = 553 mPa·s), polypropylene glycol (f = 2, Mn = 500 g / mol, OH = 248 mg KOH / g, viscosity (25 °C) = 72 mPa·s), sucrose-based polyether polyols (f = 5, Mn = 500 g / mol, OH = 490 mg KOH / g, viscosity (25 °C) = 8450 mPa·s), tetrafunctional polyether polyols based on ethylenediamine and propylene oxide (f = 4, Mn = 300 g / mol, OH = 753 mg KOH / g, viscosity (25 °C) = 42000 mPa·s), and mixtures of two or more thereof, and more preferably selected from the group consisting of: polytetrahydrofuran (f = 2, Mn = 2000 g / mol, OH = 56 mg KOH / g) and trifunctional polyether polyols containing secondary hydroxyl groups (f = 3, Mn = 3500 g / mol, OH = 48, viscosity (25 °C) = 600 mPa·s; or f = 3, Mn = 3000 g / mol, OH = 53 mg KOH / g, viscosity (25 °C) = 553 mPa·s). For the viscosity at 25 °C: DIN 53 240, and for the OH value, DIN EN 12092.

[0125] Alternatively, aliphatic polycarbonate polyols suitable as polyols are obtainable by reaction of carbonic acid derivatives (e.g. diphenyl carbonate, dimethyl carbonate or phosgene) with diols. Such usable diols include, for example, ethylene glycol, propane-1,2- and -1,3-diol, butane-1,3- and 1,4-diol, hexane-1,6-diol, octane-1,8-diol, neopentyl glycol, 1,4-bishydroxymethyl-cyclohexane, 2-methylpropane-1,3-diol, 2,2,4-trimethylpentane-1,3-diol, dipropylene glycol, polypropylene glycol, dibutylene glycol, polybutylene glycol and also lactone-modified diols. The diol component preferably contains 40% to 100% by weight of hexane-1,6-diol and / or hexanediol derivatives, preferably those with ether or ester groups and terminal OH groups, such as the products obtained by the reaction of 1 mol of hexanediol with at least 1 mol, preferably 1 to 2 mol, of ε-caprolactone or by etherification of hexanediol itself to obtain di- or trihexanediol. Polyether polycarbonate polyols can also be used. Among the aliphatic polycarbonate polyols, preferred are polycarbonate polyols based on dimethyl carbonate and hexanediol and / or butanediol and / or ε-caprolactone. Very particularly preferred are polycarbonate polyols based on dimethyl carbonate and hexanediol and / or ε-caprolactone. Preferred polycarbonate polyols have a molecular weight Mn of 400 to 10.000 g / mol, preferably 500 to 5.000 g / mol, as determined by gel permeation chromatography as described above.

[0126] Other possible polyols are mentioned, for example, in “Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes] Polyurethane [Polyurethane]”, Carl Hanser Verlag, 3rd edition, 1993, Chapters 3.1, 3.2 and 3.3.2.

[0127] 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.

[0128] Preferably, the poly(ureaurethane) polymer is obtainable or obtained by a process comprising

[0129] (i), (ii) and / or (iii), more preferably (i) and (ii), are reacted with at least one additive, wherein the at least one additive is selected from the group consisting of benzoyl chloride and diethylene glycol bischloroformate.

[0130] Any other additives other than those known to the person skilled in the art as listed above may be used in the reaction of (i), (ii) and / or (iii).

[0131] Preferably, the poly(ureaurethane) polymer is obtainable or obtained in the absence of a catalyst.

[0132] Preferably, the poly(ureaurethane) polymer is obtainable or obtained by a process comprising

[0133] - reacting the at least one isocyanate (i) with the at least one polyol (ii) to obtain a prepolymer, and

[0134] - reacting the obtained prepolymer with the at least one secondary amine (iii);

[0135] or

[0136] - reacting the at least one isocyanate (i) with the at least one secondary amine (iii) to obtain a prepolymer, and

[0137] - reacting the obtained prepolymer with the at least one polyol (ii).

[0138] 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, even more preferably in the range of 1:0.30 to 1:0.20.

[0139] 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, even more preferably in the range of 1:0.8 to 1:0.7.

[0140] Preferably, the reaction of components (i), (ii) and / or (iii) is carried out at a temperature in the range of greater than 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, even more preferably in the range of 10 °C to 150 °C, even more preferably in the range of 20 °C to 90 °C.

[0141] Preferably, the poly(urea - urethane) polymer is obtainable or obtained by a process further comprising curing the mixture of (i), (ii) and (iii), more preferably at a temperature in the range of 90 °C to 200 °C, even more preferably in the range of 100 °C to 150 °C.

[0142] Preferably, the poly(urea - urethane) polymer is thermoplastic or thermosetting.

[0143] Preferably, the poly(urea - urethane) polymer of the present invention is a covalently adaptable polymer, preferably a covalently adaptable network (CAN) thermoset or a covalently adaptable system (CAS) / thermoplastic.

[0144] Preferably, the poly(urea - urethane) polymer of the present invention is recyclable.

[0145] Preferably, the poly(urea - urethane) polymer has a solubility in toluene in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure, more preferably the poly(urea - urethane) polymer has a solubility in toluene in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure.

[0146] Preferably, the poly(urea - urethane) polymer has a solubility in 1,3 - dimethyl - 2 - imidazolidinone in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure, more preferably the poly(urea - urethane) polymer has a solubility in an organic solvent in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure.

[0147] Preferably, the poly(urea - urethane) polymer has a melting point in the range of 10 °C to 200 °C at a pressure of 880 kPa, more preferably in the range of 50 °C to 190 °C at a pressure of 880 kPa, more preferably in the range of 60 °C to 180 °C at a pressure of 880 kPa, as determined by a hot press (preferably measured using a circular press with a 17 cm diameter and an applied force of 20 kN).

[0148] The present invention further relates to a composite material based on a poly(urea - urethane) polymer, which is obtainable or obtained by

[0149] - reacting the following components:

[0150] (i) at least one isocyanate;

[0151] (ii) at least one polyol; and

[0152] (iii) at least one secondary amine having the following formula (I):

[0153]

[0154] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 - —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; wherein

[0155] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0156] -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene;

[0157] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0158] -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene;

[0159] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0160] -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;

[0161] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0162] -Z8- is a substituted or unsubstituted 5- to 30-membered heteroalkenyl;

[0163] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0164] -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroaryl;

[0165] -Z 11 - is an arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10

[0166] -Z 12 - is -N(R f )-;

[0167] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heteroalkyl, where at least one of the one or more heteroatoms of Z 13 comes from X a ;

[0168] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0169] where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b being NH, the corresponding C a and / or C b is a C atom;

[0170] where

[0171] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 ​Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0172] R b and R e are each independently as defined for R c , R d , R f and R g ; or

[0173] There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or

[0174] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, and there is no R f and R g both; and

[0175] C b and R b form a substituted or unsubstituted C6-C 30 arylene, and there is no R c and R d both; or

[0176] (C)-C a and R e form a substituted or unsubstituted C6-C 30 arylene, and without R f and R g both; or

[0177] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and without R c and R d both;

[0178] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in any one of (A);

[0179] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A),

[0180] obtain a mixture comprising a poly(urea - urethane) polymer, more preferably a poly(urea - urethane) polymer as described herein;

[0181] and

[0182] - contacting the obtained mixture with (iv):

[0183] (iv) a filler selected from the group consisting of: glass fiber, carbon fiber, mineral fiber, textile, metal mesh, metal fiber, metal rod, carbonate, wood, and mixtures of two or more thereof.

[0184] Preferably, the at least one secondary amine (iii) has the following formula (I)

[0185]

[0186] wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 - where n = 1, 2, 3, 4, 5, or 6 - and -Z1-Z 12 -Z1-; wherein

[0187] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0188] -Z2- is a substituted or unsubstituted, straight-chain or branched 2-membered to 300,000-membered heteroalkylene;

[0189] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0190] -Z4- is a substituted or unsubstituted, straight-chain or branched 3-membered to 30-membered heteroalkenylene;

[0191] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0192] -Z6- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkylene;

[0193] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0194] -Z8- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkenylene;

[0195] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0196] -Z 10 - is a substituted or unsubstituted 5-membered to 30-membered heteroarylene;

[0197] -Z 11 - is a C6-C arylene group substituted by -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl groups; 10

[0198] -Z 12 - is -N(R f )-;

[0199] -Z 13 - is a substituted or unsubstituted 5- to 30-membered heteroalkylidene group, where at least one of the one or more heteroatoms of Z 13 comes from X a ;

[0200] where C a is a C atom or an H atom and C b is a C atom or an H atom, where C a and C b at least one of them is a C atom;

[0201] where X a is an O atom or NH and X b is an O atom or NH, where X a and X b at least one of them is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0202] where

[0203] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl groups, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl groups, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl groups, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl groups, substituted or unsubstituted C5-C 30 cycloalkyl groups, substituted or unsubstituted C5-C 30 cycloalkenyl groups, substituted or unsubstituted 5- to 30-membered heteroalkylidene groups, substituted or unsubstituted 5- to 30-membered heteroalkenylidene groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted 5- to 30-membered heteroaryl groups, substituted or unsubstituted C1-C​10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl,

[0204] R b and R e independently of each other as R c 、R d 、R f and R g are defined; or

[0205] without R b and R e and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a 、C b 、X a 、X b and R a ; or

[0206] (B)C a and R e form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and without R f and R g both; and

[0207] C b and R b form a substituted or unsubstituted C6-C 30 arylene, more preferably phenyl, and without R c and R d both.

[0208] Preferably, the filler (iv) is glass fiber.

[0209] 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.

[0210] Furthermore, the present invention relates to a method for preparing the poly(urea - urethane) polymer of the present invention, which comprises:

[0211] (a) React at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0212] (b) Contact the prepolymer obtained in (a) with at least one secondary amine having formula (I) as defined in the present invention to obtain a poly(ureaurethane) polymer; or

[0213] (a’) React at least one isocyanate (i) with at least one secondary amine having formula (I) as defined in the present invention to obtain a prepolymer;

[0214] (b’) Contact the prepolymer obtained in (a’) with at least one polyol (ii) to obtain a poly(ureaurethane) polymer.

[0215] Preferably, (a) or (a’) is carried out at a temperature in the range of 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0216] Preferably, one or more of (a) and (b) or one or more of (a’) and (b’), more preferably (a) and (b) or (a’) and (b’) are carried out in the absence of a solvent.

[0217] Preferably, (b) or (b’) is carried out at a temperature in the range of 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0218] Preferably, the method further comprises

[0219] (c) Curing the mixture obtained in (b) or (b’), more preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C.

[0220] Furthermore, the present invention relates to a method for preparing a composite material according to the present invention, the method comprising:

[0221] (1) Providing a poly(ureaurethane) polymer, which comprises

[0222] (1.1) Reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0223] (1.2) Contacting the prepolymer obtained in (1.1) with at least one secondary amine (iii) having formula (I) as defined in the present invention;

[0224] or

[0225] (1.1’) React at least one isocyanate (i) with at least one secondary amine, where the at least one secondary amine (iii) has the formula (I) as defined in the present invention, to obtain a prepolymer;

[0226] (1.2’) Contact the prepolymer obtained in (1.1’) with at least one polyol (ii);

[0227] (2) Contact the polymer obtained in (1.2) or (1.2’) with a filler (iv) as defined in the present invention.

[0228] Preferably, (1) is carried out at a temperature in the range of 0 °C to 200 °C, more preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, more preferably in the range of 20 °C to 90 °C.

[0229] Preferably, one or more of (1) and (2), more preferably (1) and (2), are carried out in the absence of a solvent.

[0230] Preferably, in (2), the contact of the polymer with the filler is carried out by mixing or pressing.

[0231] In the context of the present invention, it is also conceivable that step (2) uses other thermomechanical methods, such as injection molding, casting.

[0232] Preferably, the pressing is carried out at a pressure in the range of 440 kPa to 1320 kPa (preferably measured as an applied force of 10 to 30 kN pressed by a circular press with a diameter of 17 cm), more preferably in the range of 660 kPa to 1100 kPa (preferably measured as an applied force of 15 to 25 kN pressed by a circular press with a diameter of 17 cm), more preferably in the range of 792 kPa to 968 kPa (preferably measured as an applied force of 18 to 22 kN pressed by a circular press with a diameter of 17 cm).

[0233] Preferably, the pressing is a hot pressing, more preferably carried out at a temperature in the range of 100 °C to 200 °C, more preferably in the range of 120 °C to 160 °C, more preferably in the range of 130 °C to 150 °C.

[0234] Preferably, the pressing is carried out for a duration in the range of 1 to 60 min, more preferably in the range of 4 to 20 min, more preferably in the range of 5 to 10 min.

[0235] Preferably, the method further comprises

[0236] (1.3) The polymer obtained in (1.2) or (1.2’) is more preferably cured at a temperature in the range of 90°C to 150°C, more preferably in the range of 100°C to 120°C;

[0237] Or

[0238] (3) The polymer obtained in (2) is more preferably cured at a temperature in the range of 90°C to 150°C, more preferably in the range of 100°C to 120°C.

[0239] The present invention further relates to the use of the poly(ureaurethane) polymer according to the present invention or the poly(ureaurethane) polymer composite material according to the present invention as a recyclable material.

[0240] The present invention further relates to a recyclable article comprising the poly(ureaurethane) polymer according to the present invention or the poly(ureaurethane) polymer composite material according to the present invention.

[0241] The present invention further relates to a method for shaping the poly(ureaurethane) polymer according to the present invention or the poly(ureaurethane) polymer obtainable or obtained by the method according to the present invention, which comprises:

[0242] Shaping the poly(ureaurethane) polymer, wherein shaping the polymer comprises

[0243] (x) Applying pressure and heat to the poly(ureaurethane) polymer to obtain a shaped body, more preferably a foil or sheet; or

[0244] (x’) Extruding the poly(ureaurethane) polymer to obtain a shaped body, more preferably granules or a paste.

[0245] Preferably, the pressure applied according to (x) is in the range of 10 3 to 10 7 Pa, more preferably in the range of 1.5 x 10 3 to 10 6 Pa.

[0246] Preferably, the heating according to (x) is carried out at a temperature in the range of 60°C to 250°C, more preferably in the range of 65°C to 150°C, more preferably in the range of 70°C to 130°C.

[0247] Preferably, the extrusion according to (x’) is carried out at a temperature in the range of 140°C to 220°C, more preferably in the range of 160°C to 200°C, more preferably in the range of 170°C to 190°C.

[0248] 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.

[0249] The present invention is further illustrated by the following groups of examples and combinations of examples obtained from the dependencies and cross - references as shown. In particular, it should be noted that in each case where a series of examples is mentioned, for example, in the context of terms such as "a poly(urea - urethane) polymer as described in any one of Examples 1 to 4", each example in the series is intended to be explicitly disclosed to the person skilled in the art, that is, the wording of the term should be understood by the person skilled in the art as synonymous with "a poly(urea - urethane) polymer as described in any one of Examples 1, 2, 3, and 4". Furthermore, it should be clearly stated that the following groups of examples represent suitable structural parts of the general description of the preferred aspects of the present invention and thus appropriately support but do not represent the claims of the present invention.

[0250] 1. A poly(urea - urethane) polymer obtainable or obtained by a method comprising the following:

[0251] - Reacting the following components:

[0252] (i) At least one isocyanate;

[0253] (ii) At least one polyol; and

[0254] (iii) At least one secondary amine having the following formula (I):

[0255]

[0256] where -R a - Selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1 - Z5 -, -Z5 - Z1 - Z5 -, -Z1 - Z6 -, -Z1 - Z7 -, -Z1 - Z8 -, -Z1 - Z9 -, -Z9 - Z1 - Z9 -, -Z1 - Z 10 -, -Z3 - Z5 -, -Z3 - Z6 -, -Z3 - Z7 -, -Z3 - Z8 -, -Z3 - Z9 -, -Z3 - Z 10 -, -Z1 - Z5 - Z1 -, -Z1 - Z9 - Z1 -, -Z9 - Z1(-Z 11 -Z1) n -Z9 - —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1 - Z 12 -Z1 -; where

[0257] -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene;

[0258] -Z2- is a substituted or unsubstituted, straight-chain or branched 2-membered to 300,000-membered heteroalkylene;

[0259] -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene;

[0260] -Z4- is a substituted or unsubstituted, straight-chain or branched 3-membered to 30-membered heteroalkenylene;

[0261] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0262] -Z6- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkylene;

[0263] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0264] -Z8- is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkenylene;

[0265] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0266] -Z 10 - is a substituted or unsubstituted 5-membered to 30-membered heteroarylene;

[0267] -Z 11 - is an arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10 -Z

[0268] - is -N(R 12 )-; f )-;

[0269] -Z 13 - is a substituted or unsubstituted 5-membered to 30-membered heterocycloalkylene, where at least one of one or more heteroatoms of Z 13 is from X a ;

[0270] where C a is a C atom or an H atom and C b is a C atom or an H atom, where C a and C b at least one of which is a C atom;

[0271] wherein X a is an O atom or NH and X b is an O atom or NH, wherein X a and X b at least one of which is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0272] wherein

[0273] (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl,

[0274] R b and R e are each independently as defined for R c , R d , R f and R g ; or

[0275] there is no R b and Re and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a and C b and X a and X b and R a ; or

[0276] (B) C a and R e form a substituted or unsubstituted C6-C 30 arylene, preferably phenyl, and not both R f and R g ; and C b and R b form a substituted or unsubstituted C6-C 30 arylene, preferably phenyl, and not both R c and R d ; or

[0277] (C) -C a and R e form a substituted or unsubstituted C6-C 30 arylene, and not both R f and R g ; or

[0278] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and not both R c and R d ;

[0279] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently defined as any one of R c , R d , R f and R g in (A);

[0280] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently defined as any one of R c , R d, R f and R g is defined by any one of the following.

[0281] 2. The poly(urea - urethane) polymer according to Example 1, wherein X a is NH, X b is NH, and the secondary amine (iii) has the following formula (II)

[0282]

[0283] where C a 、C b 、R b 、R c 、R d 、R e 、R f 、R g and -R a - are defined as in formula (I).

[0284] 3. The poly(urea - urethane) polymer according to Example 1 or 2, wherein -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1 - Z5-, -Z5 - Z1 - Z5-, -Z9 - Z1 - Z9-, -Z1 - Z5 - Z1-, -Z1 - Z9 - Z1- and -Z9 - Z1(-Z 11 - Z1) n - Z9-, where n = 1, 2, 3, 4, 5, or 6, preferably selected from the group consisting of: -Z2-, -Z9 - Z1 - Z9- and -Z9 - Z1(-Z 11 - Z1) n - Z9-, where n = 1, 2, 3, 4, 5, or 6, more preferably selected from the group consisting of: -Z2- and -Z9 - Z1(-Z 11 - Z1) n - Z9-, where n = 1, 2, 3, 4, 5, or 6.

[0285] 4. The poly(urea-carbamate) polymer according to any one of Examples 1 to 3, wherein -Z1- is selected from the group consisting of: -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH(CH3)-CH2-CH2-, -CH2-CH2-CH(CH2CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, and -(CH2) 10 -.

[0286] 5. The poly(urea-carbamate) polymer according to any one of Examples 1 to 4, wherein -Z9- is selected from the group consisting of phenylene, naphthylene, biphenylene, fluorene, and indenyl, and -Z9- is preferably phenylene.

[0287] 6. The poly(urea-carbamate) polymer according to Example 5, wherein -R a - is -Z9-Z1-Z9-, where -Z9- is phenylene, preferably p-phenylene, and -Z1- is -CH2-.

[0288] 7. The poly(urea-carbamate) polymer according to Example 5, wherein -R a - is -Z9-Z1(-Z 11 -Z1) n -Z9-, where n = 1, 2, 3, 4, 5, or 6, where -Z9- is phenylene and -Z1- is -CH2-, and where -Z 11 - is a C6-arylene group substituted with -NHR.

[0289] 8. The poly(urea-carbamate) polymer according to any one of Examples 1 to 5, wherein -Z2- is a substituted or unsubstituted, linear or branched heteroalkylene group having 2 to 500 members, preferably a substituted or unsubstituted, linear or branched heteroalkylene group having 2 to 35 members, more preferably a substituted or unsubstituted, linear or branched heteroalkylene group having 2 to 30 members.

[0290] 9. The poly(urea - urethane) polymer according to Example 8, wherein -Z2- is selected from the group consisting of: -CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -(CH(CH3)-CH2-O) 1-100 -CH(CH3)-CH2-, -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -(where R x1 is -CH2-CH3, where R y1 is [-O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ), where m1 + n1 + o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C(R l )(R m )(R n ), and where m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O]o3 -CH2-CH(CH)3- (where n3 is in the range of 8 to 10 and m3 + o3 is in the range of 3 to 4, or where n3 is in the range of 12 to 13 and m3 + o3 is in the range of 5 to 7, or where n3 is in the range of 38 to 40 and m3 + o3 is in the range of 5 to 7), -[CH-CH2-O] m4 -CH2-CH2- (where m4 is in the range of 8 to 250), and -[CH2-CH2-NH] m5 -(where m5 is in the range of 10 to 100,000);

[0291] where -Z2- is preferably -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-CH2-[O-CH2-CH(CH3)] o1 -, where R x1 is -CH2-CH3, where R y1 is -CH2-[O-CH2-CH(CH3)] n1 -NH-C(R l )(R m )(R n ), where m1 + n1 + o1 is in the range of 5 to 6.

[0292] 10. The poly(urea - urethane) polymer according to any one of Examples 1 to 9, wherein R c , R d , R f and R g are independently selected from the group consisting of: hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec - butyl, tert - butyl, sec - isoamyl, 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 , preferably selected from the group consisting of: hydrogen, methyl and ethyl, more preferably selected from the group consisting of: hydrogen, methyl and ethyl,

[0293] where R k is selected from the group consisting of: hydrogen, straight - chain or branched, substituted or unsubstituted C1 - C 30 alkyl, straight - chain or branched, substituted or unsubstituted C2 - C 30Alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkylene C5-C 30 Cycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 Alkylene C6-C 30 Aryl and substituted or unsubstituted C1-C 10 Alkylene 5- to 30-membered heteroaryl.

[0294] 11. The poly(urea-carbamate) polymer according to any one of Examples 1 to 10, wherein R b and R e are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-alkyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl, preferably selected from the group consisting of hydrogen, methyl, and ethyl.

[0295] 12. The poly(urea-carbamate) polymer according to any one of Examples 1 to 11, wherein any one of R b , R c and R d is H, and any one of R e , R f and R g is H;

[0296] wherein except for the one that is H, one of R b , R c and R d is CH3, and except for the one that is H, one of R e , Rf and R g One of them is CH3.

[0297] 13. The poly(urea - urethane) polymer according to any one of Examples 1 to 12, wherein R b , R c and R d Any one of them is ethyl, and R e , R f and R g Any one of them is ethyl;

[0298] Preferably, wherein

[0299] Except for the one that is ethyl, R b , R c and R d One of them is H,

[0300] Except for the one that is ethyl, R e , R f and R g One of them is H,

[0301] Except for the one that is ethyl or H, R b , R c and R d One of them is CH3, and

[0302] Except for the one that is ethyl or H, R e , R f and R g One of them is CH3.

[0303] 14. The poly(urea - urethane) polymer according to any one of Examples 1 to 13, wherein the at least one secondary amine (iii) is 4,4'-methylenebis(N - sec - butylaniline) (DIB - MDA);

[0304] Or wherein the at least one secondary amine (iii) is DIB - butanediamine (N,N’ - di - sec - butyl - 1,4 - butanediamine);

[0305] Or wherein the at least one secondary amine (iii) is 2 - (ethylamino)ethanol.

[0306] 15. The poly(urea - urethane) polymer according to any one of Examples 1 to 13, wherein the at least one secondary amine (iii) is a sec - butyl - modified polyetheramine, CH3 - CH2 - CH(CH3)-NH - [CH(CH3)-CH2 - O] m1 -CH2 - C(R x1 )(R y1 ) - CH2 - [O - CH2 - CH(CH3)]o1 -NH-CH(CH3)-CH2-CH3, where R x1 is -CH2-CH3, where 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.

[0307] 16. The poly(urea - urethane) polymer according to any one of Examples 1 to 15, wherein the at least one isocyanate (i) has an NCO functionality of 2 or greater, preferably 2 or 3; wherein preferably the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3 or greater, preferably, the at least one isocyanate (i) is a mixture of an isocyanate having an NCO functionality of 2 and an isocyanate having an NCO functionality of 3.

[0308] 17. The poly(urea-carbamate) polymer according to any one of Examples 1 to 16, wherein the at least one isocyanate (i) is selected from the group consisting of: monomeric methylene diphenylene diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenylene diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, 2,6-xylene diisocyanate, naphthalene 1,5-diisocyanate (1,5-NDI), butane 1,4-diisocyanate, pentane 1,5-diisocyanate (PDI), hexane 1,6-diisocyanate (HDI), octane 1,8-diisocyanate, nonane 1,9-diisocyanate, decane 1,10-diisocyanate, 2,2-dimethylpentane 1,5-diisocyanate, 2-methylpentane 1,5-diisocyanate (MPDI), 2,4,4(or 2,2,4)-trimethylhexane 1,6-diisocyanate (TMDI), cyclohexane 1,3- and 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), methylene-bis(isocyanatocyclohexane) (H12MDI), 2,4- or 2,6-diisocyanato-1-methylcyclohexane (H6TDI), 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane (AMCI), 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane-4,4',4''-triisocyanate, toluene-2,4,6-triyltriisocyanate, ethyl ester 1-lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, tris(isocyanatomethyl)cyclohexane, 1,8-diisocyanato-4-(isocyanatomethyl)octane, undecane 1,6,11-triisocyanate, 1,7-diisocyanato-4-(3-isocyanatopropyl)heptane, 1,6-diisocyanato-3-(isocyanatomethyl)hexane, 2,2-bis[[4-(isocyanatomethyl)phenyl]methyl]butyl n-[[4-(isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6-trioxotriazine-1,3,5(2h,4h,6h)-triyl)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)]tris[3,5,5-trimethylcyclohexyl]triisocyanate, 1,3,5-triazine-2,4,6-triisocyanate, 2,4,4'-triisocyanato-dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4'-diphenyl ether triisocyanate, 1,3-bis(3-isocyanato-4-methylphenyl)-1,3-diazetidine-2,4-dione, and mixtures of two or more thereof,

[0309] preferably selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), naphthalene 1,5-diisocyanate (1,5-NDI), 1,4-diisocyanate, pentane 1,5-diisocyanate (PDI), hexane 1,6-diisocyanate (HDI), methylene-bis(isocyanatocyclohexane) (H12MDI), and mixtures of two or more thereof.

[0310] 18. The poly(urea-carbamate) polymer according to Example 17, wherein the at least one isocyanate (i) is selected from the group consisting of: monomeric methylene diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), and toluene diisocyanate (TDI).

[0311] 19. The poly(urea-carbamate) polymer according to any one of Examples 1 to 18, wherein the at least one polyol (i) is selected from the group consisting of: polyester polyols, polyether ester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols, and mixtures thereof.

[0312] 20. The poly(urea-carbamate) polymer according to Example 19, wherein the at least one polyol (i) is selected from the group consisting of polyester polyols and polyether polyols.

[0313] 21. The poly(urea-carbamate) polymer according to Example 20, wherein the at least one polyol (ii) is a polyether polyol, and the polyether polyol is preferably selected from the group consisting of: polytetrahydrofuran, trifunctional polyether polyols containing secondary hydroxyl groups, polypropylene glycol, sucrose-based polyether polyols, tetrafunctional polyether polyols based on ethylenediamine and propylene oxide, and mixtures of two or more thereof, more preferably from the group consisting of polytetrahydrofuran and trifunctional polyether polyols containing secondary hydroxyl groups.

[0314] 22. The poly(urea-carbamate) polymer according to any one of Examples 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.

[0315] 23. The poly(urea-carbamate) polymer according to any one of Examples 1 to 22, wherein the polymer is obtainable or obtained by a method comprising

[0316] reacting (i), (ii) and / or (iii), preferably (i) and (ii), with at least one additive selected from the group consisting of benzoyl chloride and diethylene glycol bischloroformate.

[0317] 24. The poly(urea-carbamate) polymer according to any one of Examples 1 to 23, wherein the polymer is obtainable or obtained by a method in the absence of a catalyst.

[0318] 25. The poly(urea-carbamate) polymer according to any one of Examples 1 to 24, which is obtained or obtainable by a method comprising

[0319] - reacting the at least one isocyanate (i) with the at least one polyol (ii) to obtain a prepolymer, and

[0320] - reacting the obtained prepolymer with the at least one secondary amine (iii);

[0321] or

[0322] obtained or obtainable by a method comprising:

[0323] - reacting the at least one isocyanate (i) with the at least one secondary amine (iii) to obtain a prepolymer, and

[0324] - reacting the obtained prepolymer with the at least one polyol (ii).

[0325] 26. The poly(urea-carbamate) polymer according to any one of Examples 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, more preferably in the range of 1:0.30 to 1:0.20.

[0326] 27. The poly(urea-carbamate) polymer according to any one of Examples 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, more preferably in the range of 1:0.8 to 1:0.7.

[0327] 28. The poly(urea-carbamate) polymer according to any one of embodiments 1 to 27, wherein the reaction of the component (i), (ii) and / or (iii) is carried out at a temperature in the range of greater than 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, and even more preferably in the range of 20 °C to 90 °C.

[0328] 29. The poly(urea-carbamate) polymer according to any one of embodiments 1 to 27, which is obtained or obtainable by a method further comprising curing a mixture of (i), (ii) and (iii) preferably at a temperature in the range of 90 °C to 200 °C, more preferably in the range of 100 °C to 150 °C.

[0329] 30. The poly(urea-carbamate) polymer according to any one of embodiments 1 to 29, which is thermoplastic or thermosetting.

[0330] 31. The poly(urea-carbamate) polymer according to any one of embodiments 1 to 30, which has a solubility in toluene in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure, preferably having a solubility in toluene in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 12 hours at a temperature of 110 °C and at ambient pressure.

[0331] 32. The poly(urea-carbamate) polymer according to any one of embodiments 1 to 31, which has a solubility in 1,3-dimethyl-2-imidazolidinone in the range of 0.05:1 to 1:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure, preferably having a solubility in an organic solvent in the range of 0.075:1 to 0.5:1 g / mL (grams of dissolved polymer: mL of solvent) measured after heating for a duration of at least 20 hours at a temperature of 130 °C and at ambient pressure.

[0332] 33. A poly(urea - urethane) polymer as described in any one of embodiments 1 to 32, having a melting point determined by a hot press (preferably measured using a circular press with a 17 cm diameter at an applied force of 20 kN) in the range of 10 °C to 200 °C at a pressure of 880 kPa, more preferably determined by a hot press (preferably measured using a circular press with a 17 cm diameter at an applied force of 20 kN) in the range of 50 °C to 190 °C at a pressure of 880 kPa, even more preferably determined by a hot press (preferably measured using a circular press with a 17 cm diameter at an applied force of 20 kN) in the range of 60 °C to 180 °C at a pressure of 880 kPa.

[0333] 34. A composite material based on a poly(urea - urethane) polymer, obtainable or obtained by

[0334] - reacting the following components:

[0335] (i) at least one isocyanate;

[0336] (ii) at least one polyol; and

[0337] (iii) at least one secondary amine having the following formula (I):

[0338]

[0339] where -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1 - Z5-, -Z5 - Z1 - Z5-, -Z1 - Z6-, -Z1 - Z7-, -Z1 - Z8-, -Z1 - Z9-, -Z9 - Z1 - Z9-, -Z1 - Z 10 -, -Z3 - Z5-, -Z3 - Z6-, -Z3 - Z7-, -Z3 - Z8-, -Z3 - Z9-, -Z3 - Z 10 -, -Z1 - Z5 - Z1-, -Z1 - Z9 - Z1-, -Z9 - Z1(-Z 11 -Z1) n -Z9 - —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1 - Z 12 -Z1-; where

[0340] -Z1- is a substituted or unsubstituted, straight - chain or branched C1 - C 30 alkylene;

[0341] -Z2- is a substituted or unsubstituted, linear or branched heteroalkylene group having 2 to 300,000 atoms;

[0342] -Z3- is a substituted or unsubstituted, linear or branched C2-C 30 alkenylene;

[0343] -Z4- is a substituted or unsubstituted, linear or branched heteroalkenylene group having 3 to 30 atoms;

[0344] -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene;

[0345] -Z6- is a substituted or unsubstituted hetero-cycloalkylene group having 5 to 30 atoms;

[0346] -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene;

[0347] -Z8- is a substituted or unsubstituted hetero-cycloalkenylene group having 5 to 30 atoms;

[0348] -Z9- is a substituted or unsubstituted C6-C 30 arylene;

[0349] -Z 10 - is a substituted or unsubstituted hetero-arylene group having 5 to 30 atoms;

[0350] -Z 11 - is a C6-C arylene group substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, linear or branched C1-C 30 alkyl; 10

[0351] -Z 12 - is -N(R f )-;

[0352] -Z 13 - is a substituted or unsubstituted hetero-cycloalkylene group having 5 to 30 atoms, where at least one of the one or more heteroatoms of Z 13 comes from X a ;

[0353] where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom;

[0354] where X a is an O atom or NH and X b is an O atom or NH, where X​a and X b at least one of which is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom;

[0355] wherein

[0356] (A) R c 、R d 、R f and R g are each independently selected from the group consisting of: hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl,

[0357] R b and R e are each independently as defined for R c 、R d 、R f and R g ; or

[0358] there is no R b and R e and C a and C b are connected to each other via a single bond to form a structure consisting of C a 、Cb , X a , X b and R a to form a heterocycle; or

[0359] (B) C a and R e form a substituted or unsubstituted C6-C 30 arylene, preferably phenyl, and without both R f and R g ; and C b and R b form a substituted or unsubstituted C6-C 30 arylene, preferably phenyl, and without both R c and R d ; or

[0360] (C) - C a and R e form a substituted or unsubstituted C6-C 30 arylene, and without both R f and R g ; or

[0361] -C b and R b form a substituted or unsubstituted C6-C 30 arylene, and without both R c and R d ;

[0362] wherein, when C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently defined as any one of R c , R d , R f and R g under (A);

[0363] wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently defined as any one of R c , R d , R f and R g under (A),

[0364] Obtain a mixture comprising a poly(ureaurethane) polymer, more preferably a poly(ureaurethane) polymer according to any one of Examples 1 to 33;

[0365] and

[0366] - Contact the obtained mixture with component (iv):

[0367] (iv) a filler selected from the group consisting of: glass fiber, carbon fiber, mineral fiber, textile, metal mesh, metal fiber, metal rod, carbonate, wood, and a mixture of two or more thereof.

[0368] 35. The composite material according to Example 34, wherein the filler (iv) is glass fiber.

[0369] 36. A method for preparing a poly(ureaurethane) polymer according to any one of Examples 1 to 33, comprising:

[0370] (a) React at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0371] (b) Contact the prepolymer obtained in (a) with at least one secondary amine having the formula (I) as defined in any one of Examples 1 to 15 to obtain the poly(ureaurethane) polymer; or

[0372] (a’) React at least one isocyanate (i) with at least one secondary amine having the formula (I) as defined in any one of Examples 1 to 15 to obtain a prepolymer;

[0373] (b’) Contact the prepolymer obtained in (a’) with at least one polyol (ii) to obtain a poly(ureaurethane) polymer.

[0374] 37. The method according to Example 36, wherein (a) or (a’) is carried out at a temperature in the range of 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, even more preferably in the range of 20 °C to 90 °C.

[0375] 38. The method according to Example 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’), are carried out in the absence of a solvent.

[0376] 39. The method according to any one of Examples 36 to 38, wherein (b) or (b’) is carried out at a temperature in the range of 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, and even more preferably in the range of 20 °C to 90 °C.

[0377] 40. The method according to any one of Examples 36 to 39, further comprising

[0378] (c) curing the mixture obtained in (b) or (b’) at a temperature preferably in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C.

[0379] 41. A method for preparing a composite material according to Example 34 or 35, the method comprising:

[0380] (1) providing a poly(ureaurethane) polymer, which comprises

[0381] (1.1) reacting at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer;

[0382] (1.2) contacting the prepolymer obtained in (1.1) with at least one secondary amine, the at least one secondary amine (iii) having the formula (I) as defined in any one of Examples 1 to 15;

[0383] or

[0384] (1.1’) reacting at least one isocyanate (i) with at least one secondary amine - the at least one secondary amine (iii) having the formula (I) as defined in any one of Examples 1 to 15 - to obtain a prepolymer;

[0385] (1.2’) contacting the prepolymer obtained in (1.1’) with at least one polyol (ii);

[0386] (2) contacting the polymer obtained in (1.2) or (1.2’) with a filler as defined in Example 31 or 32.

[0387] 42. The method according to Example 41, wherein (1) is carried out at a temperature in the range of 0 °C to 200 °C, preferably in the range of 1 °C to 200 °C, more preferably in the range of 10 °C to 150 °C, and even more preferably in the range of 20 °C to 90 °C.

[0388] 43. The method according to Example 41 or 42, wherein one or more of (1) and (2), preferably (1) and (2), are carried out in the absence of a solvent.

[0389] 44. The method according to any one of Examples 41 to 43, wherein in (2), the contact of the polymer with the filler is carried out by mixing or pressing.

[0390] 45. The method according to Example 44, wherein the pressing is carried out at a pressure in the range of 440 kPa to 1320 kPa (preferably measured as an applied force of 10 to 30 kN pressed by a circular press having a diameter of 17 cm), more preferably in the range of 660 kPa to 1100 kPa (preferably measured as an applied force of 15 to 25 kN pressed by a circular press having a diameter of 17 cm), and more preferably in the range of 792 kPa to 968 kPa (preferably measured as an applied force of 18 to 22 kN pressed by a circular press having a diameter of 17 cm).

[0391] 46. The method according to any one of Examples 41 to 44, further comprising

[0392] (1.3) curing the polymer obtained in (1.2) or (1.2’) preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C;

[0393] or

[0394] (3) curing the polymer obtained in (2) preferably at a temperature in the range of 90 °C to 150 °C, more preferably in the range of 100 °C to 120 °C.

[0395] 47. Use of the poly(urea - urethane) polymer according to any one of Examples 1 to 33 or the poly(urea - urethane) polymer composite material according to Example 34 or 35 as a recyclable material.

[0396] 48. A recyclable article comprising the poly(urea - urethane) polymer according to any one of Examples 1 to 33 or the poly(urea - urethane) polymer composite material according to Example 34 or 35.

[0397] 49. A method for shaping the poly(urea - urethane) polymer according to any one of Examples 1 to 33 or the poly(urea - urethane) polymer obtainable or obtained by the method according to any one of Examples 36 to 40, comprising:

[0398] shaping the poly(urea - urethane) polymer, wherein shaping the polymer comprises

[0399] (x) applying pressure and heat to the poly(urea - urethane) polymer to obtain a shaped body, preferably a foil or a sheet; or

[0400] (x') The poly(urea-urethane) polymer is extruded to obtain a shaped body, preferably granules or a paste.

[0401] 50. The method according to Example 49, wherein the pressure applied according to (x) is in the range of 10 3 to 10 7 Pa, preferably in the range of 1.5 x 10 3 to 10 6 Pa.

[0402] 51. The method according to Example 49 or 50, wherein the heating according to (x) is carried out at a temperature in the range of 60 °C to 250 °C, preferably in the range of 65 °C to 150 °C, more preferably in the range of 70 °C to 130 °C.

[0403] 52. The method according to any one of Examples 49 to 51, wherein the extrusion according to (x') is carried out at a temperature in the range of 140 °C to 220 °C, preferably in the range of 160 °C to 200 °C, more preferably in the range of 170 °C to 190 °C.

[0404] In the context of the present invention, the term "alkylene" relates to an acyclic saturated hydrocarbon group, which may be an acyclic saturated hydrocarbon chain that combines different moieties, such as having 1 to 30 (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30) C atoms in the case of C1-C 30 alkylene, or having 1 to 5 (i.e., 1, 2, 3, 4 or 5) C atoms in the case of C1-C5 alkylene. 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-C6H 13 )-, -CH2-CH(n-C7H 15 )-, -CH2-CH(n-C8H 17)-, -CH(CH3)-CH(CH3)-, -C(CH3)2-, -CH2-C(CH3)2-CH2-, -CH2-[C(CH3)2]2-CH2-, -CH2-CH(CH3)-CH2-C(CH3)2-CH2-CH2-, -CH2-C(CH3)2-CH2-CH(CH3)-CH2-CH2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, -(CH2) 10 -, -(CH2)7-, -(CH2)9-, -(CH2) 11 -, -(CH2) 12 -, -(CH2) 13 -, -(CH2) 14 -, -(CH2) 15 -, -(CH2) 16 -, -(CH2) 17 -, -(CH2) 18 -, -(CH2) 19 -, -(CH2) 20 -, -(CH2) 21 -, -(CH2) 22 -, -(CH2) 23 -, -(CH2) 24 -, -(CH2) 25 -, -(CH2) 26 -, -(CH2) 27 -, -(CH2) 28 -, -(CH2) 29 - and -(CH2) 30 -.

[0405] In the context of the present invention, the term "heteroalkylene" refers to an alkylene as described above, in which one or more carbon atoms have been replaced by heteroatoms independently selected from the group consisting of oxygen, sulfur, and nitrogen (-NH-). The heteroalkylene may preferably have 1, 2, or 3 heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen (-NH-), particularly preferably 1 heteroatom, as one or more chain linkages. The heteroalkylene may preferably be 2- to 30-membered, particularly preferably 2- to 12-membered, and very particularly preferably 2- or 6-membered. More preferably, oxygen (-O-) is the most preferred heteroatom in the "heteroalkylene". Representative examples of heteroalkylene include, but are not limited to, (-CH2-O-CH2-) 1-500 , (-CH2-O-CH(CH3)-) 1-500 , -(CH(CH3)-CH2-O) 1-100-CH(CH3)-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-O-CH(CH3)-, -CH2-O-CH(CH2CH3)-, -CH2-O-CH(n-C3H7)-, -CH2-O-CH(n-C4H9)-, -CH2-O-CH(n-C5H 11 )-, -CH2-O-CH(n-C6H 13 )-, -CH2-O-CH(n-C7H 15 )-, -CH2-O-CH(n-C8H 17 )-, -CHO-(CH3)-CHO-(CH3)-, -CO-(CH3)2-, -CH2-O-C(CH3)2-CH2-, -CH2-[O-C(CH3)2]2-CH2-, -(CH2)3-O-CH2-, -(CH2)4-O-CH2-, -(CH2)5-O-CH2-, -(CH2)6-O-CH2-, -(CH2)8-OCH2-, -(CH2) 10 -O-CH2-, -(CH2)7-O-CH2-, -(CH2)9-O-CH2-, -(CH2) 11 -O-CH2-, -(CH2) 12 -O-CH2-, -(CH2) 13 -O-CH2-, -(CH2) 14 -O-CH2-, -(CH2) 15 -O-CH2-, -(CH2) 16 -O-CH2-, -(CH2) 17 -O-CH2-, -(CH2) 18 -O-CH2-, -(CH2) 19 -O-CH2-, -(CH2) 20 -O-CH2-, -(CH2) 21 -OCH2-, -(CH2) 22 -OCH2-, -(CH2) 23 -O-CH2-, -(CH2) 24 -OCH2-, -(CH2) 25 -OCH2-, -(CH2) 26 -OCH2-, -(CH2) 27 -O-CH2-, -(CH2) 28 -O-CH2-, -(CH2) 29 -O-CH2-, -(CH2) 30-O-CH2-, -CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH-, -CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-N(CH3)-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-NH-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-O-CH2-CH2-CH2-, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, -CH(CH3)-CH2-NH-CH2-CH(CH3)-, -CH2-CH2-NH-CH2-CH2-, -[CH(CH3)-CH2-O] m1 -CH2-C(R x1 )(R y1 )-[O-CH2-CH(CH3)] o1 -, where R x1 is -CH2-CH3 (where R y1 is [-O-CH2-CH(CH3)] n1 -NH-C d (R l (R m (R n ), and where m1 + n1 + o1 is in the range of 5 to 6), -[CH(CH3)-CH2-O] m2 -CH2-CH(R y2 )-[O-CH2-CH(CH3)] o2 -(where R y2 is [-O-CH2-CH(CH3)] n2 -NH-C d (R l (R m (R n ), and where m2 + n2 + o2 is in the range of 45 to 85), -[CH(CH3)-CH2-O] m3 -[CH2-CH2-O] n3 -[CH2-CH(CH3)-O] o3-CH2-CH(CH)3- (where n3 is in the range of 8 to 10 and m3 + o3 is in the range of 3 to 4, or where n3 is in the range of 12 to 13 and m3 + o3 is in the range of 5 to 7, or where n3 is in the range of 38 to 40 and m3 + o3 is in the range of 5 to 7), -[CH-CH2-O] m4 -CH2-CH2- (where m4 is in the range of 8 to 250), and -[CH2-CH2-NH] m5 -(where m5 is in the range of 10 to 100,000).

[0406] 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, and which may be branched or straight-chain and unsubstituted or at least monosubstituted, such as having 2 to 30 (i.e., 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30) C-atoms in the case of alkenylene, more preferably C2-C 30 alkenylene, most preferably C2-C 20 alkenylene, and most preferably C2-C 10 alkenylene, and especially C2-C6 alkenylene. Representative examples of alkenylene include, but are not limited to, -CH=CH- and -CH2-CH=CH-.

[0407] In the context of the present invention, the term "heteroalkenylene" relates to an alkenylene as described above, in which one or more carbon atoms have been replaced by heteroatoms independently selected from the group consisting of oxygen, sulfur and nitrogen (NH). The heteroalkenylene may preferably have 1, 2 or 3 heteroatoms, particularly preferably 1 heteroatom, selected from the group consisting of oxygen, sulfur and nitrogen (NH), as one or more chain linkages. The heteroalkenylene may preferably be 3-membered to 30-membered, particularly preferably 3-membered to 12-membered, very particularly preferably 3-membered or 6-membered. Representative examples of heteroalkenylene include, but are not limited to, -CH=CH-NH-, -CH=CH-O-, -CH=CH-CH2-O- and -CH=CH-S-.

[0408] In the context of the present invention, it is conceivable that if one or more of the substituents represent an alkylene, alkenylene, heteroalkylene and heteroalkenylene or contain such groups which are mono- or polysubstituted, then the group is preferably substituted by 1, 2, 3, 4 or 5, particularly preferably by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C1-5 -alkyl)2, -NH-phenyl, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein the above -C 1-5 alkyl residue is in each case straight-chain or branched and the above phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably by 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5-alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, and -S-CH2F. It is contemplated that the alkylene, alkenylene, heteroalkylene, and heteroalkenylene are each independently unsubstituted or substituted with 1, 2, or 3 substituents independently selected from the group consisting of phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -SH, -S-phenyl, -NH2, -N(CH3)2, -N(C2H5)2, and -N(CH3)(C2H5), wherein the phenyl residue is unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents independently selected from the group consisting of F, Cl, Br, I, -OH, -SH, -NO2, -CN, -O-CH3, -O-CF3, and -O-C2H5.

[0409] In the context of the present invention, the term "cycloalkylene" relates to saturated cyclic hydrocarbon groups. C5-C 30 Representative examples of cycloalkylene include, but are not limited to, cyclopentylene (e.g., cyclopent-1,3-ylidene, cyclopent-1,2-ylidene), cyclohexylene (e.g., cyclohex-1,4-ylidene, cyclohex-1,3-ylidene, and cyclohex-1,2-ylidene), cycloheptylene, cyclooctylene (e.g., 1,5-cyclooctylene),

[0410]

[0411] In the context of the present invention, the term "cycloalkylene" also relates to bridged cyclic hydrocarbon groups, such as cyclic hydrocarbon groups having 2 to 4 rings with 5 to 30 carbon atoms. Representative examples include, but are not limited to, norbornylene (e.g., 1,4-norbornylene and 2,5-norbornylene), norbornyl (e.g., 2,6-norbornyl), and adamantylene (e.g., 1,5-adamantylene and 2,6-adamantylene).

[0412] In the context of the present invention, the term "heterocycloalkylene" also relates to cyclic or polycyclic saturated divalent groups having 5 to 30 ring members, wherein the carbon atoms are replaced by 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S. Representative examples include, but are not limited to, 1,5-dioxaoctylene, 4,8-dioxabicyclo[3.3.0]octylene.

[0413] In the context of the present invention, the term "subcycloalkenyl" relates to a divalent cycloalkenyl ring structure, i.e., a cycloalkenyl having two single bonds as attachment points to other groups as defined herein. Representative examples of "subcycloalkenyl" include, but are not limited to, cyclopent-1,2-ene-3,5-ylidene, 3-cyclohexene-1,2-ylidene, 2,5-cyclohexadiene-1,4-ylidene, cyclohex-1,2-ene-3,5-ylidene, 2,5-cyclohexadiene-1,4-ylidene, and cyclohept-1,2-ene-3,5-ylidene.

[0414] In the context of the present invention, the term "subheterocycloalkenyl" relates to a cyclic or polycyclic non-aromatic unsaturated divalent group having 5 to 30 carbon atoms (wherein the carbon atoms are replaced by 1, 2, or 3 heteroatoms selected from the heteroatoms N, O, and S) and having 1, 2, or 3 double bonds.

[0415] In the context of the present invention, it is conceivable that if one or more of the substituents represent a mono- or poly-substituted subcycloalkyl, subcycloalkenyl, subheterocycloalkyl, and subheterocycloalkenyl, then the group is preferably substituted by 1, 2, 3, 4, or 5, particularly preferably by 1, 2, or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C 1-5 -alkyl)2, -NH-phenyl, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2, and -SO3H, wherein the above -C 1-5The alkyl residue is straight-chain or branched in each case and the abovementioned phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 -alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 -alkenyl, -C 2-5 -alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F. It is conceivable that the alkylene, alkenylene, heteroalkylene and heteroalkenylene groups are independently unsubstituted or substituted by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -SH, -S-phenyl, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5), where the phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -SH, -NO2, -CN, -O-CH3, -O-CF3 and -O-C2H5.

[0416] In the context of the present invention, the term "arylene" refers to a closed aromatic divalent ring or ring system, such as phenylene, naphthylene, biphenylene, fluorenylene and indenylene.

[0417] In the context of the present invention, the term "heteroarylene" refers to a closed aromatic divalent ring or ring system having at least one heteroatom selected from nitrogen, oxygen and sulfur. Representative examples of heteroarylene include, but are not limited to, furanylene, thienylene, pyridinylene, quinolinylene, isoquinolinylene, indolylene, isoindolylene, triazolylene, pyrrolylene, tetrazolylene, imidazolylene, pyrazolylene, oxazolylene, thiazolylene, benzofuranylene, benzothienylene, carbazolylene, benzoxazolylene, pyrimidinylene, benzimidazolylene, quinoxalinylene, benzothiazolylene, naphthyridinylene, isoxazolylene, isothiazolylene, purinylene, quinazolinylene, pyrazinylene, 1-oxopyridinylene, pyridazinylene, triazinylene (preferably one or more of vicinal-triazinylene, unsymmetrical-triazinylene and symmetrical-triazinylene), tetrazinylene, oxadiazolylene and thiadiazolylene.

[0418] In the context of the present invention, it is conceivable that, if one or more of the substituents represent a mono- or polysubstituted arylene and heteroarylene, this is preferably substituted by 1, 2, 3 or 4, particularly preferably by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -O-CH2-phenyl, -SH, -S-phenyl, -S-CH2-phenyl, -NH2, -N(C 1-5 -alkyl)2, -NH-phenyl, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-O-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, where the above -C 1-5The alkyl residue is straight-chain or branched in each case and the above-mentioned phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 -alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 -alkenyl, -C 2-5 -alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2 and -S-CH2F. It is conceivable that the alkylene, alkenylene, heteroalkylene and heteroalkenylene are independently of one another unsubstituted or substituted by 1, 2 or 3 substituents independently selected from the group consisting of: phenyl, F, Cl, Br, I, -NO2, -CN, -O-phenyl, -SH, -S-phenyl, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5), where the phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -SH, -NO2, -CN, -O-CH3, -O-CF3 and -O-C2H5.

[0419] In the context of the present invention, the term "alkyl" refers to an acyclic saturated hydrocarbon residue which can be branched or straight-chain and unsubstituted or at least monosubstituted, e.g. having 1 to 30 (i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30) C atoms in the case of C1-C 30 alkyl or having 1 to 5 (i.e. 1, 2, 3, 4 or 5) C atoms in the case of C1-C5 alkyl. In the context of the present invention, it is conceivable that if one or more of the substituents represent a monosubstituted or polysubstituted alkyl or contain a monosubstituted or polysubstituted alkyl, this is preferably substituted by 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3 substituents independently selected from the group consisting of: F, Cl, Br, I, -OH, -NO2, -CN, -SH, -NH2, -N(C 1-5 -alkyl)2, -N(C1-5 -(alkyl)(phenyl), -N(C 1-5 -(alkyl)(CH2-phenyl), -N(C 1-5 -(alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C 1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-)-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein said C 1-5 -alkyl residue is straight-chain or branched in each case and said phenyl residue is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2H5, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl. Particularly preferred substituents may be independently selected from the group consisting of: F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0420] In the context of the present invention, unsubstituted straight-chain C1-C 30Alkyl preferably refers to an alkyl selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, and tetracosyl; more preferably selected from the group consisting of hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, and tetracosyl; more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; and even more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0421] In the context of the present invention, unsubstituted branched C1-C 30The alkyl group preferably refers to an alkyl group selected from the group consisting of isopropyl, isobutyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, neopentyl, 2-methyl-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, isohexyl, isoheptyl, 2,6-dimethyl-4-heptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, isoeicosyl, and 3-pinanyl-methyl, more preferably selected from the group consisting of 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, isoeicosyl, 2-methyltricosyl, 2-ethyldocosyl, 3-ethylhenicosyl, 3-ethylicosyl, 4-propylhenicosyl, propylnonadecyl, 6-butyldodecyl, and 5-ethylundecyl. In the context of the present invention, a polysubstituted alkyl group should be understood as an alkyl group that is polysubstituted, preferably disubstituted or trisubstituted, on different or the same C atoms, for example, trisubstituted on the same C atom as in the case of -CF3, or substituted at different positions as in the case of -(CHCl)-(CH2F). The polysubstitution can be carried out with the same or different substituents. Representative examples of substituents include, but are not limited to, -CH3, -CF3, -CF2H, -CFH2, -(CH2)-OH, -(CH2)-NH2, -(CH2)-CN, -(CH2)-(CF3), -(CH2)-(CHF2), -(CH2)-(CH2F), -(CH2)-(CH2)-O-CH3, -(CH2)-(CH2)-NH2, -(CH2)-(CH2)-CN, -(CF2)-(CF3), -(CH2)-(CH2)-(CF3), and -(CH2)-(CH2)-(CH2)-O-CH3.

[0422] In the context of the present invention, a substituted, straight-chain or branched C1-C 30 alkyl group also refers to a straight-chain or branched saturated hydrocarbon group having C1-C 30 carbon atoms substituted with a functional group selected from the group consisting of F, Cl, Br, I, -OH, 2-furyl, -NO2, -CN, -SH, -NH2, -N(C 1-5 -alkyl)2, -N(C 1-5 -alkyl)(phenyl), -N(C 1-5 -alkyl)(CH2-phenyl), -N(C 1-5 -alkyl)(CH2-CH2-phenyl), -C(=O)-H, -C(=O)-C1-5 -alkyl, -C(=O)-phenyl, -C(=S)-C 1-5 -alkyl, -C(=S)-phenyl, -C(=O)-OH, -C(=O)-O-C 1-5 -alkyl, -C(=O)-)-phenyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, -S(=O)-C 1-5 -alkyl, -S(=O)-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)2-phenyl, -S(=O)2-NH2 and -SO3H, wherein said C 1-5 -alkyl residue is in each case straight-chain or branched and said phenyl residue is preferably unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -CF3, -NH2, -O-CF3, -SH, -O-CH3, -O-C2H5, -O-C3H7, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl. Particularly preferred substituents may be independently selected from the group consisting of: F, Cl, Br, I, -NO2, -CN, -SH, -NH2, -N(CH3)2, -N(C2H5)2 and -N(CH3)(C2H5).

[0423] In the context of the present invention, the substituted, straight-chain or branched C1-C 30 alkyl also refers to having C1-C 30A branched or straight-chain saturated hydrocarbon group in which a carbon atom is substituted by a functional group selected from the group consisting of a hydroxyl group, an alkoxy group, C(=O)R, CN, and SR, and is preferably selected from the group consisting of: 1-methoxymethyl, 1-methoxymethyl, 1-methoxyethyl, 1-methoxypropyl, 1-methoxybutyl, 2-hydroxy-butyl, 1-methoxypentyl, 1-methoxyhexyl, 1-methoxyheptyl, 1-methoxyoctyl, 1-methoxynonyl, decyl, 1-methoxyundecyl, 1-methoxydodecyl, 1-methoxytridecyl, 1-methoxytetradecyl, 1-methoxypentadecyl, 1-methoxyhexadecyl, 1-methoxyheptadecyl, 1-methoxyoctadecyl, 1-methoxynonadecyl, 1-methoxyicosyl, 1-methoxydocosyl, 1-methoxytetracosyl, 2-methoxypropyl, 2-methoxybutyl, 2-methoxypentyl, 2-methoxyhexyl, 2-methoxyheptyl, 2-methoxyoctyl, 2-methoxynonyl, decyl, 2-methoxyundecyl, 2-methoxydodecyl, 2-methoxytridecyl, 2-methoxytetradecyl, 2-methoxypentadecyl, 2-methoxyhexadecyl, 2-methoxyheptadecyl, 2-methoxyoctadecyl, 2-methoxynonadecyl, 2-methoxyicosyl, 2-methoxydocosyl, 2-methoxytetracosyl, 1-acetoxymethyl, 1-acetoxyethyl, 1-acetoxypropyl, 1-acetoxybutyl, 1-acetoxypentyl, 1-acetoxyhexyl, 1-acetoxyheptyl, 1-acetoxyoctyl, 1-acetoxynonyl, decyl, 1-acetoxyundecyl, 1-acetoxydodecyl, 1-acetoxytridecyl, 1-acetoxytetradecyl, 1-acetoxypentadecyl, 1-acetoxyhexadecyl, 1-acetoxyheptadecyl, 1-acetoxyoctadecyl, 1-acetoxynonadecyl, 1-acetoxyicosyl, 1-acetoxydocosyl, 1-acetoxytetracosyl, 1-cyanomethyl, 1-cyanoethyl, 1-cyanopropyl, 1-cyanobutyl, 1-cyanopentyl, 1-cyanohexyl, 1-cyanoheptyl, 1-cyanooctyl, 1-cyanononyl, decyl, 1-cyanoundecyl, 1-cyanododecyl, 1-cyanotridecyl, 1-cyanotetradecyl, 1-cyanopentadecyl, 1-cyanohexadecyl, 1-cyanoheptadecyl, 1-cyanooctadecyl, 1-cyanononadecyl, 1-cyanoicosyl, 1-cyanodocosyl, 1-cyanotetracosyl, 2-cyanopropyl, 2-cyanobutyl, 2-cyanopentyl, 2-cyanohexyl, 2-cyanoheptyl, 2-cyanooctyl, 2-cyanononyl, decyl, 2-cyanoundecyl,2-cyanododecyl, 2-cyanotridecyl, 2-cyanotetradecyl, 2-cyanopentadecyl, 2-cyanohexadecyl, 2-cyanoheptadecyl, 2-cyanooctadecyl, 2-cyanononadecyl, 2-cyanoeicosyl, 2-cyanounicosyl, 2-cyanodocosyl, 2-cyanotricosyl, 2-cyanotetracosyl, 1-sulfonylmethyl, 1-sulfonylethyl, 1-sulfonylpropyl, 1-sulfonylbutyl, 1-sulfonylpentyl, 1-sulfonylhexyl, 1-sulfonylheptyl, 1-sulfonyloctyl, 1-sulfonylnonyl, decyl, 1-sulfonylundecyl, 1-sulfonyldodecyl, 1-sulfonyltridecyl, 1-sulfonyltetradecyl, 1-sulfonylpentadecyl, 1-sulfonylhexadecyl, 1-sulfonylheptadecyl, 1-sulfonyloctadecyl, 1-sulfonylnonadecyl, 1-sulfonyleicosyl, 1-sulfonylunicosyl, 1-sulfonyldocosyl, 1-sulfonyltricosyl and 1-sulfonyltetracosyl.

[0424] In the context of the present invention, the term "alkenyl" refers to an unsubstituted, straight-chain C2-C 30 alkenyl. Representative examples of alkenyl include, but are not limited to, 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-icosenyl and 2-icosenyl, more preferably selected from 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-icosenyl and 2-icosenyl, 20-henicosenyl, 2-docosenyl, 6-tricosenyl and 2-tetracosenyl.

[0425] Unsubstituted branched C2-C 30Representative examples of alkenyl groups include, but are not limited to, isopropenyl, isobutenyl, neopentenyl, 2-ethylhexenyl, 2-propylheptenyl, 2-butyl octenyl, 2-pentylnonenyl, 2-hexyldecenyl, isohexenyl, isoheptenyl, isooctenyl, isononenyl,isodecenyl, isododecenyl, isotetradecenyl, isohexadecenyl, isooctadecenyl, isoeicosanyl, 2-methyltricosanyl, 2-ethyldocosanyl, 3-ethylhenicosanyl, 3-ethyl eicosanyl, 4-propylhenicosanyl, 4-propylnonadecanyl, 6-butyldodecenyl, 5-ethylundecenyl, 1,4-hexadienyl, 1,3-hexadienyl, 2,5-hexadienyl, 3,5-hexadienyl, 2,4-hexadienyl, 1,3,5-hexatriene, 1,3,6-heptatriene, 1,4,7-octatriene or 2-methyl-1,3,5-hexatriene, 1,3,5,7-octatetraene, 1,3,5,8-nonatetraene, 1,4,7,10-undecatetraene, 2-ethyl-1,3,6,8-nonatetraene, 2-vinyl-1,3,5,8-nonatetraene, 1,3,5,7,9-decapentaene, 1,4,6,8,10-undecapentaene and 1,4,6,9,11-dodecapentaene.

[0426] In the context of the present invention, a substituted, straight-chain or branched C2-C 30 alkenyl group means a straight-chain or branched unsaturated hydrocarbon group having from C2-C 30 carbon atoms substituted by a functional group selected from: alkoxy, C(=O)R, CN and SR; where R is hydrogen, a substituted or unsubstituted straight-chain or branched C1-C 30 alkyl group, a substituted or unsubstituted straight-chain or branched C2-C 30 alkenyl group, a substituted or unsubstituted C5-C 30 cycloalkyl group, a substituted or unsubstituted C5-C 30 cycloalkenyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C7-C 30 arylalkyl group.

[0427] In the context of the present invention, the term "alkenyl" further means having C2-C 30A branched or straight-chain unsaturated hydrocarbon group in which a carbon atom is substituted with a functional group selected from the following: alkoxy, C(=O)R, CN, and SR; preferably selected from the group consisting of: 1-methoxyvinyl, 2-methoxypropenyl, 4-methoxybutenyl, 3-methoxypentenyl, 5-methoxyhexenyl, 2-methoxyheptenyl, 5-methoxyoctenyl, 3-methoxynonenyl, 6-methoxyundecenyl, 1-methoxydodec-2-enyl, 1-methoxytridec-5-enyl, 3-methoxytetradec-5-enyl, 3-methoxypentadec-12-enyl, 10-methoxyhexadec-15-enyl, 12-methoxyoctadec-16-enyl, 1-methoxyoctadec-3-enyl, 1-methoxynonadec-2-enyl, 1-methoxyicos-20-enyl, 1-methoxyheneicos-2-enyl, 1-methoxydocos-4-enyl, 1-methoxytricos-22-enyl, 1-methoxytetracos-23-enyl, 2-methoxyprop-1-enyl, 2-methoxybut-1-enyl, 2-methoxypent-4-enyl, 2-methoxyhex-2-enyl, 2-methoxyhept-3-enyl, 2-methoxyoct-7-enyl, 2-methoxynon-5-enyl, 2-methoxyundec-10-enyl, 2-methoxydodec-4-enyl, 2-methoxytridec-12-enyl, 2-methoxytetradec-10-enyl, 2-methoxypentadec-14-enyl, 2-methoxyhexadec-1-enyl, 2-methoxyoctadec-12-enyl, 2-methoxynonadec-10-enyl, 2-methoxyicos-18-enyl, 2-methoxyheneicos-2-enyl, 2-methoxydocos-3-enyl, 20-methoxytricos-2-enyl, 21-methoxytetracos-4-enyl, 1-acetoxyvinyl, 1-acetoxyprop-1-enyl, 1-acetoxybut-2-enyl, 1-acetoxypent-4-enyl, 1-acetoxyhex-2-enyl, 1-acetoxyhept-1-enyl, 1-acetoxyoct-7-enyl, 1-acetoxynon-2-enyl, 5-acetoxydec-3-enyl, 1-acetoxyundec-10-enyl, 1-acetoxydodec-2-enyl, 1-acetoxytridec-12-enyl, 10-acetoxytetradec-2-enyl, 15-acetoxypentadec-2-enyl, 10-acetoxyhexadec-2-enyl, 11-acetoxyoctadec-1-enyl, 13-acetoxyoctadec-2-enyl, 1-acetoxynonadec-14-enyl, 20-acetoxyicos-19-enyl, 1-acetoxyheneicos-2-enyl, 1-acetoxydocos-10-enyl, 1-acetoxytricos-22-enyl, 1-acetoxytetracos-23-enyl, 1-cyanoeth-1-enyl, 1-cyanoprop-2-enyl,1-cyanobut-2-enyl, 1-cyanopent-3-enyl, 1-cyanohex-5-enyl, 1-cyanohept-6-enyl, 1-cyanooct-2-enyl, 1-cyanonon-3-enyl, 11-cyanoundec-2-enyl, 10-cyanododec-2-enyl, 10-cyanotridec-12-enyl, 1-cyanotetradec-3-enyl, 1-cyanopentadec-14-enyl, 1-cyanohexadec-15-enyl, 1-cyanoheptadec-2-enyl, 1-cyanooctadec-3-enyl, 1-cyanononadec-18-enyl, 1-cyanoeicos-10-enyl, 1-cyanodocos-20-enyl, 15-cyanodocos-3-enyl, 1-cyanotricos-20-enyl, 1-cyanotetracos-2-enyl, 2-cyanoprop-2-enyl, 2-cyanobut-1-enyl, 2-cyanopent-1-enyl, 2-cyanohex-3-enyl, 2-cyanohept-6-enyl, 2-cyanooct-1-enyl, 2-cyanonon-8-enyl, 2-cyanoundec-10-enyl, 2-cyanododec-1-enyl, 2-cyanotridec-12-enyl, 2-cyanotetradec-10-enyl, 2-cyanopentadec-3-enyl, 2-cyanohexadec-2-enyl, 2-cyanoheptadec-1-enyl, 2-cyanooctadec-12-enyl, 2-cyanononadec-15-enyl, 2-cyanoeicos-1-enyl, 2-cyanodocos-5-enyl, 2-cyanotricos-22-enyl, 2-cyanotetracos-20-enyl, 1-sulfinyleth-1-enyl, 1-sulfinylprop-2-enyl, 1-sulfinylbut-2-enyl, 1-sulfinylpent-4-enyl, 1-sulfinylhex-2-enyl, 1-sulfinylhept-5-enyl, 1-sulfinyloct-3-enyl, 1-sulfinylnon-5-enyl, 1-sulfinylundec-10-enyl, 1-sulfinyldodec-11-enyl, 1-sulfinyltridec-2-enyl, 1-sulfinyltetradec-4-enyl, 1-sulfinylpentadec-5-enyl, 1-sulfinylhexadec-3-enyl, 1-sulfinylheptadec-2-enyl, 1-sulfinyloctadec-3-enyl, 1-sulfinylnonadec-15-enyl, 1-sulfinyleicos-18-enyl, 1-sulfinylheneicos-20-enyl, 1-sulfinyldocos-21-enyl, 1-sulfinyltricos-20-enyl and 1-sulfinyltetracos-22-enyl.、

[0428] In the context of the present invention, the term "heteroalkyl" means an alkyl group in which one or more carbon atoms have in each case been replaced by a heteroatom independently selected from the group consisting of oxygen, sulfur and nitrogen (NH). The heteroalkyl preferably contains 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as one or more chain linkages. In addition, the heteroalkyl can be 2- to 12-membered, preferably 2- to 6-membered.

[0429] In the context of the present invention, the term "heteroalkenyl" means an alkenyl group in which one or more carbon atoms have in each case been replaced by a heteroatom independently selected from the group consisting of oxygen, sulfur and nitrogen (NH). The heteroalkenyl preferably contains 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as one or more chain linkages. In addition, the heteroalkenyl can be 3- to 12-membered, preferably 3- to 6-membered.

[0430] In the context of the present invention, the term "cycloalkyl" means a monocyclic and bicyclic saturated alicyclic group having 5 to 30 carbon atoms. Unsubstituted or branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkyls include, but are not limited to, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl and bicyclo[3.1.1]heptyl.

[0431] In the context of the present invention, C5-C 30 The monocyclic and bicyclic cycloalkyls can be further branched with one or more identical or different alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, neopentyl, etc. Branched C3-C 10 Representative examples of monocyclic and bicyclic cycloalkyls include, but are not limited to, methylcyclohexyl and dimethylcyclohexyl.

[0432] In the context of the present invention, the term "cycloalkenyl" means a monocyclic and bicyclic unsaturated alicyclic group having 5 to 30 carbon atoms, which contains one or more double bonds. C5-C 30 Representative examples of cycloalkenyls include, but are not limited to, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl or cyclodecenyl. These groups can be branched with one or more identical or different alkyl groups, preferably branched with methyl, ethyl, n-propyl or isopropyl. Branched C5-C 30 Representative examples of monocyclic and bicyclic cycloalkenyls include, but are not limited to, methylcyclohexenyl and dimethylcyclohexenyl.

[0433] In the context of the present invention, the term "heterocycloalkyl" means a non-aromatic monocyclic or polycyclic ring containing 5 to 30 ring members, wherein at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S, and N. Representative examples of heterocycloalkyl include, but are not limited to, aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuryl, tetrahydrothiofuryl, tetrahydropyranyl, and pyranyl.

[0434] In the context of the present invention, the term "heterocycloalkenyl" refers to a non-aromatic unsaturated monocyclic or polycyclic ring containing 5 to 30 ring members (wherein at least one carbon atom as a ring member is replaced by at least one heteroatom selected from O, S, and N) and having at least one double bond. Representative examples include, but are not limited to, (2,3)-dihydrofuryl, (2,3)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1,4)-dihydropyridin-1-yl, dihydropyranyl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 4,5-dihydropyrazol-2-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydrothienyl, and (1,2,3,4)-tetrahydropyridin-1-yl.

[0435] In the context of the present invention, it is conceivable that if one or more of the substituents represent a mono- or polysubstituted heteroalkyl, heteroalkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl, then the group is preferably substituted by 1, 2, 3, 4 or 5, particularly preferably by 1, 2 or 3 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -OH, -SH, -NH2, oxo(=O), thioxo(=S), -C(=O)-OH, C 1-5 alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -(CH2)-O-C 1-5 -alkyl, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)-C 1-5 -alkyl, -NH-C 1-5 -alkyl, N(C 1-5 alkyl)(C 1-5 -alkyl), -C(=O)-O-C 1-5 -alkyl, -C(=O)-H, -C(=O)-C 1-5 -alkyl, -CH2-O-C(=O)-phenyl, -O-C(=O)-phenyl, -NH-S(=O)2-C 1-5 -alkyl, -NH-C(=O)-C 1-5 -alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, pyrazolyl, phenyl, furyl / furanyl, thiadiazolyl, thiophenyl / thienyl and benzyl, where the above C 1-5 alkyl residues are in each case straight-chain or branched and the cyclic substituents or the cyclic residues of these substituents themselves are in each case unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably by 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -CF3, -OH, -NH2, -O-CF3, -SH, -O-C 1-5-alkyl, -O-phenyl, -O-CH2-phenyl, -(CH2)-O-C 1-5 -alkyl, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -C 1-5 alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -C(=O)-O-C 1-5 -alkyl and -C(=O)-CF3.

[0436] In the context of the present invention, the term "aryl" refers to an aromatic compound which may have more than one aromatic ring. Substituted and unsubstituted C6-C 30 Representative examples of aryl include, but are not limited to, phenyl, benzyl, cyclohexyl(phenyl)methyl, naphthyl, anthracenyl, tetraphenyl, nonacenyl and phenanthryl.

[0437] In the context of the present invention, the term "heteroaryl" refers to a monocyclic or polycyclic, preferably monocyclic, bicyclic or tricyclic aromatic hydrocarbon residue having preferably 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 ring members, particularly preferably 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 have been replaced by heteroatoms independently selected from the group consisting of oxygen, sulfur and nitrogen (NH). The heteroaryl may contain 1, 2, 3, 4 or 5, preferably 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, sulfur and nitrogen (NH) as one or more ring members. The heteroaryl may be unsubstituted or mono-substituted or identically or differently multi-substituted. Representative examples of heteroaryl include, but are not limited to, thienyl, furyl, pyrrolyl, pyrazolyl, pyrazinyl, pyranyl, triazolyl, pyridyl, imidazolyl, indolyl, isoindolyl, benzo[b]furyl, benzo[b]thienyl, benzo[d]thiazolyl, benzodiazolyl, benzotriazolyl, benzoxazolyl, benzoisoxazolyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridazinyl, pyrimidinyl, indazolyl, quinoxalinyl, quinazolinyl, quinolinyl, naphthyridinyl and isoquinolinyl.

[0438] In the context of the present invention, an aryl or heteroaryl may be fused (anellated) to a monocyclic or bicyclic ring system. Representative examples of aryls fused to a monocyclic or bicyclic ring system include, but are not limited to, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinolinyl, (2,3)-dihydro-1H-isoindolyl, (1,2,3,4)-tetrahydronaphthyl, (2,3)-dihydrobenzo[1.4]dioxinyl, benzo[1.3]dioxolyl, and (3,4)-dihydro-2H-benzo[1.4]oxazinyl.

[0439] In the context of the present invention, the term "arylalkyl" refers to an aryl ring attached to an alkyl chain. Representative examples of arylalkyls include, but are not limited to, 1-phenylmethyl, 1-phenylethyl, 1-phenylpropyl, 1-phenylbutyl, 1-methyl-1-phenyl-propyl, 3-phenylpropyl, 4-phenylbutyl, 3-phenylbutyl, and 2-methyl-3-phenyl-propyl.

[0440] In the context of the present invention, it is conceivable that if one or more of the substituents represent a mono- or polysubstituted aryl, heteroaryl, arylalkyl, or contain an aryl or heteroaryl, this may preferably be substituted by 1, 2, 3, 4, or 5, particularly preferably by 1, 2, or 3 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5 -alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, -S(=O)2-C 1-5 -alkyl, -S(=O)-C 1-5 -alkyl, -NH-C 1-5 -alkyl, N(C 1-5 alkyl)2, -C(=O)-O-C 1-5 -alkyl, -C(=O)-H; -C(=O)-C 1-5 -alkyl, -CH2-O-C(=O)-phenyl, -O-C(=O)-phenyl, -NH-S(=O)2-C 1-5-alkyl, -NH-C(=O)-C 1-5 -alkyl, -C(=O)-NH2, -C(=O)-NH-C 1-5 -alkyl, -C(=O)-N(C 1-5 -alkyl)2, pyrazolyl, phenyl, furyl / furanyl, thiazolyl, thiadiazolyl, thiophenyl / thienyl, benzyl and phenethyl, wherein said C 1-5 alkyl residue is in each case straight-chain or branched and the cyclic substituent or the cyclic residues of these substituents themselves are unsubstituted or substituted by 1, 2, 3, 4 or 5, preferably by 1, 2, 3 or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, -C 1-5 alkyl, -(CH2)-O-C 1-5 -alkyl, -C 2-5 alkenyl, -C 2-5 alkynyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -S-C 1-5 -alkyl, -S-phenyl, -S-CH2-phenyl, -O-C 1-5-alkyl, -O-phenyl, -O-CH2-phenyl, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, and -S-CH2F; most preferably, these substituents are each independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, neopentyl, vinyl, allyl, ethynyl, propargyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -CH2-O-CH3, -CH2-O-C2H5, -SH, -NH2, -C(=O)-OH, -S-CH3, -S-C2H5, -S(=O)-CH3, -S(=O)2-CH3, -S(=O)-C2H5, -S(=O)2-C2H5, -O-CH3, -O-C2H5, -O-C3H7, -O-C(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, -S-CH2F, -S(=O)2-phenyl, pyrazolyl, phenyl, -N(CH3)2, -N(C2H5)2, -NH-CH3, -NH-C2H5, -CH2-O-C(=O)-phenyl, -NH-S(=O)2-CH3, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-C(CH3)3, -C(=O)-H, -C(=O)-CH3, -C(=O)-C2H5, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -O-C(=O)-phenyl, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-N(CH3)2, phenyl, furyl / furanyl, thiadiazolyl, thiophenyl / thienyl, and benzyl,wherein the cyclic substituent or the cyclic residue of these substituents themselves is in each case unsubstituted or substituted by 1, 2, 3, 4, or 5, preferably by 1, 2, 3, or 4 substituents independently selected from the group consisting of: F, Cl, Br, I, -CN, -NO2, -SH, -NH2, -C(=O)-OH, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, neopentyl, vinyl, allyl, ethynyl, propargyl, -C≡C-Si(CH3)3, -C≡C-Si(C2H5)3, -CH2-O-CH3, -CH2-O-C2H5, -S-CH3, -S-C2H5, -S(=O)-CH3, -S(=O)2-CH3, -S(=O)-C2H5, -S(=O)2-C2H5, -O-CH3, -O-C2H5, -O-C3H7, -O-C(CH3)3, -CF3, -CHF2, -CH2F, -O-CF3, -O-CHF2, -O-CH2F, -C(=O)-CF3, -S-CF3, -S-CHF2, and -S-CH2F.,

[0441] In the context of the present invention, the substituted aryl may be selected from the group consisting of: 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-aminophenyl, 3-aminophenyl, 4-aminophenyl, 2-dimethylaminophenyl, 3-dimethylaminophenyl, 4-dimethylaminophenyl, 2-methylaminophenyl, 3-methylaminophenyl, 4-methylaminophenyl, 2-acetylphenyl, 3-acetylphenyl, 4-acetylphenyl, 2-methylsulfinylphenyl, 3-methylsulfinylphenyl, 4-methylsulfinylphenyl, 2-methylsulfonylphenyl, 3-methylsulfonylphenyl, 4-methylsulfonylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 2-fluoromethylphenyl, 3-fluoromethylphenyl, 4-fluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-tert-butylphenyl, 3-tert-butylphenyl, 4-tert-butylphenyl, 2-carboxyphenyl, 3-carboxyphenyl, 4-carboxyphenyl, 2-vinylphenyl, 3-vinylphenyl, 4-vinylphenyl, 2-ethynylphenyl, 3-ethynylphenyl, 4-ethynylphenyl, 2-allylphenyl, 3-allylphenyl, 4-allylphenyl,2-trimethylsilylethynylphenyl, 3-trimethylsilylethynylphenyl, 4-trimethylsilylethynylphenyl, 2-formylphenyl, 3-formylphenyl, 4-formylphenyl, 2-acetamidophenyl, 3-acetamidophenyl, 4-acetamidophenyl, 2-dimethylaminocarbonylphenyl, 3-dimethylaminocarbonylphenyl, 4-dimethylaminocarbonylphenyl, 2-methoxymethylphenyl, 3-methoxymethylphenyl, 4-methoxymethylphenyl, 2-ethoxymethylphenyl, 3-ethoxymethylphenyl, 4-ethoxymethylphenyl, 2-aminocarbonylphenyl, 3-aminocarbonylphenyl, 4-aminocarbonylphenyl, 2-methylaminocarbonylphenyl, 3-methylaminocarbonylphenyl, 4-methylaminocarbonylphenyl, 2-carboxymethylesterphenyl, 3-carboxymethylesterphenyl, 4-carboxymethylesterphenyl, 2-carboxyethylesterphenyl, 3-carboxyethylesterphenyl, 4-carboxyethylesterphenyl, 2-carboxy-tert-butylesterphenyl, 3-carboxy-tert-butylesterphenyl, 4-carboxy-tert-butylesterphenyl, 2-methylsulfanylphenyl, 3-methylsulfanylphenyl, 4-methylsulfanylphenyl, 2-ethylsulfanylphenyl, 3-ethylsulfanylphenyl, 4-ethylsulfanylphenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoro-methoxyphenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-4-methylphenyl, (2,3)-difluorophenyl, (2,3)-dimethylphenyl, (2,3)-dichlorophenyl, 3-fluoro-2-trifluoro-methylphenyl, (2,4)-dichlorophenyl, (2,4)-difluorophenyl, 4-fluoro-2-trifluoromethylphenyl, (2,4)-dimethoxyphenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-nitrophenyl, 2-chloro-4-methylphenyl, 2-chloro-5-trifluoromethylphenyl, 2-chloro-5-methoxyphenyl, 2-bromo-5-trifluoromethylphenyl, 2-bromo-5-methoxyphenyl, (2,4)-dibromophenyl, (2,4)-dimethylphenyl, 2-fluoro-4-trifluoromethylphenyl, (2,5)-difluorophenyl, 2-fluoro-5-trifluoro-methylphenyl, 5-fluoro-2-trifluoromethylphenyl, 5-chloro-2-trifluoromethylphenyl, 5-bromo-2-trifluoromethylphenyl, (2,5)-dimethoxyphenyl, (2,5)-bis-trifluoromethylphenyl, (2,5)-dichlorophenyl, (2,5)-dibromophenyl, 2-methoxy-5-nitrophenyl, 2-fluoro-6-trifluoro-methylphenyl, (2,6)-dimethoxyphenyl, (2,6)-dimethylphenyl, (2,6)-dichlorophenyl, 2-chloro-6-fluorophenyl, 2-bromo-6-chlorophenyl, 2-bromo-6-fluorophenyl, (2,6)-difluorophenyl, (2,6)-difluoro-3-methylphenyl, (2,6)-dibromophenyl, (2,6)-dichlorophenyl, 3-chloro-2-fluorophenyl,3-chloro-5-methylphenyl, (3,4)-dichlorophenyl, (3,4)-dimethylphenyl, 3-methyl-4-methoxyphenyl, 4-chloro-3-nitrophenyl, (3,4)-dimethoxyphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-fluoro-4-trifluoromethylphenyl, (3,4)-difluorophenyl, 3-cyano-4-fluorophenyl, 3-cyano-4-methylphenyl, 3-cyano-4-methoxyphenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-methylphenyl, 3-bromo-4-methoxyphenyl, 4-chloro-2-fluorophenyl, 4-chloro-3-trifluoromethyl, 4-bromo-3-methylphenyl, 4-bromo-5-methylphenyl, 3-chloro-4-fluorophenyl, 4-fluoro-3-nitrophenyl, 4-bromo-3-nitrophenyl, (3,4)-dibromophenyl, 4-chloro-3-methylphenyl, 4-bromo-3-methylphenyl, 4-fluoro-3-methylphenyl, 3-fluoro-4-methylphenyl, 3-fluoro-5-methylphenyl, 2-fluoro-3-methylphenyl, 4-methyl-3-nitrophenyl, (3,5)-dimethoxyphenyl, (3,5)-dimethylphenyl, (3,5)-bis-trifluoromethylphenyl, (3,5)-difluorophenyl, (3,5)-dinitrophenyl, (3,5)-dichlorophenyl, 3-fluoro-5-trifluoromethylphenyl, 5-fluoro-3-trifluoro-methylphenyl, (3,5)-dibromophenyl, 5-chloro-4-fluorophenyl, 5-chloro-4-fluorophenyl, 5-bromo-4-methylphenyl, (2,3,4)-trifluorophenyl, (2,3,4)-trichlorophenyl, (2,3,6)-trifluorophenyl, 5-chloro-2-methoxyphenyl, (2,3)-difluoro-4-methyl, (2,4,5)-trifluorophenyl, (2,4,5)-trichlorophenyl, (2,4)-dichloro-5-fluorophenyl, (2,4,6)-trichlorophenyl, (2,4,6)-trimethylphenyl, (2,4,6)-trifluorophenyl, (2,4,6)-trimethoxyphenyl, (3,4,5)-trimethoxyphenyl, (2,3,4,5)-tetrafluorophenyl, 4-methoxy-(2,3,6)-trimethylphenyl, 4-methoxy-(2,3,6)-trimethylphenyl, 4-chloro-2,5-dimethylphenyl, 2-chloro-6-fluoro-3-methylphenyl, 6-chloro-2-fluoro-3-methyl, (2,4,6)-trimethylphenyl and (2,3,4,5,6)-pentafluorophenyl.,

[0442] In the context of the present invention, examples of substituted heteroaryl are 3-methylpyridin-2-yl, 4-methylpyridin-2-yl, 5-methylpyridin-2-yl, 6-methylpyridin-2-yl, 2-methylpyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, 6-methylpyridin-3-yl, 2-methylpyridin-4-yl, 3-methylpyridin-4-yl, 3-fluoropyridin-2-yl, 4-fluoropyridin-2-yl, 5-fluoropyridin-2-yl, 6-fluoropyridin-2-yl, 3-chloropyridin-2-yl, 4-chloropyridin-2-yl, 5-chloropyridin-2-yl, 6-chloropyridin-2-yl, 3-trifluoromethylpyridin-2-yl, 4-trifluoromethylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 6-trifluoromethylpyridin-2-yl, 3-methoxypyridin-2-yl, 4-methoxypyridin-2-yl, 5-methoxypyridin-2-yl, 6-methoxypyridin-2-yl, 4-methylthiazol-2-yl, 5-methylthiazol-2-yl, 4-trifluoromethylthiazol-2-yl, 5-trifluoromethylthiazol-2-yl, 4-chlorothiazol-2-yl, 5-chlorothiazol-2-yl, 4-bromothiazol-2-yl, 5-bromothiazol-2-yl, 4-fluorothiazol-2-yl, 5-fluorothiazol-2-yl, 4-cyanothiazol-2-yl, 5-cyanothiazol-2-yl, 4-methoxythiazol-2-yl, 5-methoxythiazol-2-yl, 4-methyloxazol-2-yl, 5-methyloxazol-2-yl, 4-trifluoromethyloxazol-2-yl, 5-trifluoromethyloxazol-2-yl, 4-chlorooxazol-2-yl, 5-chlorooxazol-2-yl, 4-bromooxazol-2-yl, 5-bromooxazol-2-yl, 4-fluorooxazol-2-yl, 5-fluorooxazol-2-yl, 4-cyanooxazol-2-yl, 5-cyanooxazol-2-yl, 4-methoxyoxazol-2-yl, 5-methoxyoxazol-2-yl, 2-methyl-(1,2,4)-thiadiazol-5-yl, 2-trifluoromethyl-(1,2,4)-thiadiazol-5-yl, 2-chloro-(1,2,4)-thiadiazol-5-yl, 2-fluoro-(1,2,4)-thiadiazol-5-yl, 2-methoxy-(1,2,4)-thiadiazol-5-yl, 2-cyano-(1,2,4)-thiadiazol-5-yl, 2-methyl-(1,2,4)-oxadiazol-5-yl, 2-trifluoromethyl-(1,2,4)-oxadiazol-5-yl, 2-chloro-(1,2,4)-oxadiazol-5-yl, 2-fluoro-(1,2,4)-oxadiazol-5-yl, 2-methoxy-(1,2,4)-oxadiazol-5-yl and 2-cyano-(1,2,4)-oxadiazol-5-yl.

[0443] In the context of the present invention, the term "substituted" for any one of the alkylenes, heteroalkylenes, alkenylenes, heteroalkenylenes, cycloalkylenes, hetero cycloalkylenes, cycloalkenylenes, hetero cycloalkenylenes, arylenes and heteroarylenes disclosed herein respectively refers to mono - substituted or multi - substituted alkylenes, heteroalkylenes, alkenylenes, heteroalkenylenes, cycloalkylenes, hetero cycloalkylenes, cycloalkenylenes, hetero cycloalkenylenes, arylenes and heteroarylenes, which may preferably be substituted with 1, 2, 3, 4 or 5, more preferably with 1, 2 or 3 substituents. Examples of substituents are - NHR 1 , where R 1 is - C(R u )(R v )(R w ), where R u , R v and R w are independently selected from the group consisting of: hydrogen, straight - chain or branched, substituted or unsubstituted C1 - C 30 alkyl, straight - chain or branched, substituted or unsubstituted C2 - C 30 alkenyl, substituted or unsubstituted, straight - chain or branched 2 - to 30 - membered heteroalkyl, substituted or unsubstituted, straight - chain or branched 3 - to 30 - membered heteroalkenyl, substituted or unsubstituted C5 - C 30 cycloalkyl, substituted or unsubstituted C5 - C 30 cycloalkenyl, substituted or unsubstituted 5 - to 30 - membered heterocycloalkyl, substituted or unsubstituted 5 - to 30 - membered heterocycloalkenyl, substituted or unsubstituted C6 - C 30 aryl, substituted or unsubstituted 5 - to 30 - membered heteroaryl, substituted or unsubstituted C1 - C 10 alkylene C5 - C 30 cycloalkyl, substituted or unsubstituted C1 - C 10 alkylene C5 - C 30 cycloalkenyl, substituted or unsubstituted C1 - C 10 alkylene 5 - to 30 - membered heterocycloalkyl, substituted or unsubstituted C1 - C 10 alkylene 5 - to 30 - membered heterocycloalkenyl, substituted or unsubstituted C1 - C 10 alkylene C6 - C 30 aryl and substituted or unsubstituted C1 - C 10 alkylene 5 - to 30 - membered heteroaryl. More preferably, R u , R v and R w are independently selected from the group consisting of: hydrogen, straight - chain or branched, substituted or unsubstituted C1 - C 30 alkyl. Even more preferably, R u , R v and R wEach of the following is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-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, preferably, in -NHR 1 In, R 1 Yes-C(R u )(R v )(R w ), where C and R u Forming substituted or unsubstituted C6-C 30 Arylene, and no R v and R w Both. For example, -NHR 1 It may be -NH-Ph.

[0444] In the context of the present invention, for -Z 12 -,-N(R f )-means that the N atom is bonded to C in formula (I) a R f bonded to form a heterocyclic ring.

[0445] In the context of the present invention, a reversible NCO bond designates a bond between the N of the urea group (from the secondary hindered amine) and the C (of the NCO) which can be formed and cleaved reversibly.

[0446] In the context of the present invention, "thermosetting polymer" refers to a network polymer comprising a covalently bonded structure having at least three covalent bond attachment points between polymer chains, wherein preferably the at least three covalent bond attachment points between polymer chains form part of the polymer network.

[0447] In the context of the present invention, "thermoplastic polymer" refers to a linear polymer comprising a covalently bonded structure with two covalently bonded attachment points between polymer chains, wherein preferably these two covalently bonded attachment points between polymer chains form part of a linear polymer system.

[0448] In the context of the present invention, isocyanate is a general term for molecules containing at least one isocyanate functional group. Thus, the term "at least one isocyanate" is interpreted to cover one or more monoisocyanates, one or more diisocyanates, one or more triisocyanates, one or more tetraisocyanates, and one or more isocyanates having a higher number of isocyanate functional groups, such as polymers having one or more isocyanate functional groups. In the context of the present invention, an example of an isocyanate is polymethylene polyphenyl isocyanate, commonly also referred to as pMDI.

[0449] In the context of the present invention, the abbreviation "SHA" stands for secondary hindered amine. Secondary hindered amines are a general term well known in the art. In particular, in this term, a secondary amine is given its usual definition of an amine bonded to two separate carbons of any hybridization, where the carbons cannot be carbonyl carbons. A hindered substituent is defined as at least one carbon bonded to the amino group, which is further directly bonded to at least two other carbon groups. In the context of the present invention, non-limiting examples of secondary hindered amines are 4,4'-methylenebis(N-sec-butylaniline) (DIB-MDA), DIB-diamine (N,N’-di-sec-butyl-1,4-diaminobutane), or a sec-butyl-modified polyetheramine having the 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, where 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.

[0450] The present invention is further illustrated by the following examples.

[0451] Examples

[0452] Material Abbreviations

[0453] polyTHF (commercial product from BASF): polytetrahydrofuran (polytetramethylene ether glycol) (functionality = 2; average molecular weight Mn = 2000 g / mol, OH = 56 mg KOH / g).

[0454] MDI: 4,4’-methylenebis(phenyl isocyanate) purchased from BASF Polyurethanes GmbH

[0455] BDO: 1,4 - butanediol purchased from Alfa Aesar

[0456] DIBIS: Diethylene glycol bis - chloroformate purchased from BASF Polyurethanes GmbH

[0457] Benzoyl chloride purchased from Sigma Aldrich

[0458] TDI, a mixture of 80% 2,4 - and 20% 2,6 - toluene diisocyanate, purchased from BASF

[0459] pMDI: Polymerized diphenylmethane diisocyanate (product of BASF)

[0460] DIB - MDA: 4,4'-methylenebis(N - sec - butylaniline) purchased from abcr

[0461] DIB - butanediamine: N,N’ - di - sec - butyl - 1,4 - butanediamine DIB - polyetheramine T403 prepared from polyetheramine T403 purchased from BASF

[0462] Polyol 1 = trifunctional polyether polyol and mainly contains secondary hydroxyl groups - functionality = 3, Mn = 3500 g / mol, OH = 48 mg KOH / g, viscosity (25°C) = 600 mPa.s

[0463] Polyol 2 = glycerol - based trifunctional polyether polyol - functionality = 3, Mn = 420 g / mol, OH = 400 mgKOH / g, viscosity (25°C) = 373 mPa.s

[0464] Polymer type TP: Thermoplastic

[0465] Polymer type TS: Thermosetting plastic

[0466] Analysis methods

[0467] TGA (Thermogravimetric analysis): The spectra were obtained in a gold crucible under N2 atmosphere according to ISO 11358

[0468] NCO content: The content of NCO was determined according to DIN EN ISO 14896 (determined with Metrohm Modell 916TI - Touch)

[0469] Melting point: Samples of the polyurethane urea were cut into cubes with dimensions of 0.2×0.2×0.2 cm 3A cube with dimensions is transferred to a hot press, model number: PW20H(2006) of P / O / Weber. The sample is pressed with a circular press having a diameter of 17 cm with a force of 20 kN (equivalent to a pressure of approximately 880 kPa) for at least 5 minutes and the temperature is raised. When the solid polymer undergoes an obvious phase transition, the melting point is determined.

[0470] DSC (Differential Scanning Calorimetry) measurement: According to ASTM D 3418, DSC analysis is performed on a sample of approximately 5 - 10 mg using a DSC model Q20 of TA Instruments brand.

[0471] Swelling ratio, insoluble fraction and soluble fraction: A sample of polyurethane urea is cut into cubes with dimensions of 0.5×0.5×0.5 cm 3 The sample is allowed to swell in THF at room temperature for 24 h. Subsequently, the excess THF is removed. The swollen sample is weighed (m(swollen)). The sample is first dried under ambient conditions and then dried under vacuum at 65 °C to remove the absorbed THF. Finally, the mass of the dried sample (m(dried)) is evaluated. The swelling ratio and insoluble fraction are determined via the following equations:

[0472] Swelling ratio = [m(swollen) - m(dried)] / m(dried)

[0473] Insoluble fraction = m(dried) / m(dried)

[0474] Soluble fraction = 1 - insoluble fraction

[0475] Table 1 Overview

[0476]

[0477]

[0478] Reference Example 1A: Preparation of Prepolymer

[0479] 100 g of 4,4′-methylenebis(phenyl isocyanate) (mMDI) (0.400 mol) is immersed in a flask and placed under N2. The mixture is heated. When the MDI is melted, 0.02 g of benzoyl chloride (141 μmol) is added. 233 g of polytetrahydrofuran (polyTHF) (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) is melted and slowly added to the mixture containing mMDI at 80 °C. When the NCO value reaches <8% (molar ratio NCO:OH is approximately 1:0.3), the reaction is terminated by cooling. Prepolymer 1a is obtained as a colorless, slightly opaque liquid.

[0480] Reference Example 1B: Preparation of Prepolymer

[0481] 17.4 g of toluene diisocyanate (TDI) (0.100 mol) was placed in a flask and kept 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. When the NCO value reached <8% (molar ratio of NCO:OH ~ 1:0.3), the reaction was terminated by cooling. Prepolymer 1b was obtained as a colorless, slightly opaque liquid.

[0482] Reference Example 1C: Preparation of Prepolymer

[0483] 34.0 g of polymeric diphenylmethane diisocyanate (pMDI) (0.100 mol) and 8 mg of DIBIS (35 μmol) were mixed. 75.0 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the pMDI-containing mixture at 80 °C. When the NCO value reached <8% (molar ratio of NCO:OH approximately 1:0.25), the reaction was terminated by cooling. Prepolymer 1c was obtained as a slightly brownish, slightly opaque liquid.

[0484] Reference Example 1D: Preparation of Prepolymer

[0485] 20.0 g of mMDI (0.060 mol) was added to 20.0 g of pMDI (0.080 mol) and 8 mg of DIBIS (35 μmol). 77.5 g of polyTHF (functionality = 2, M n = 2000 g / mol, hydroxyl value = 55 mg KOH / g) was melted and slowly added to the mMDI / pMDI-containing mixture at 80 °C. When the NCO value reached <8% (molar ratio of NCO:OH approximately 1:0.3)), the reaction was terminated by cooling. A prepolymer was obtained as a slightly brownish, slightly opaque liquid.

[0486] Reference Example 2: Preparation of Prepolymer

[0487] 75.0 g of MDI (0.300 mol) was placed in a flask and kept under N2. It was heated to 80 °C, and 188 g of polyol 1 (a trifunctional polyether polyol with propylene oxide (PO) end groups and secondary hydroxyl groups, functionality = 3, M nA mixture of = 3500 g / mol, hydroxyl value = 48 mg KOH / g, viscosity (25 °C) = 600 mPa·s) and 0.008 g DIBIS (35 μmol). When the NCO value reaches <8% (molar ratio NCO:OH is about 1:0.3)), the reaction is terminated by cooling. A prepolymer 2 in the form of a colorless, slightly opaque liquid is obtained.

[0488] Reference Example 3: Preparation of DIB-Polyetheramine T403

[0489] In the presence of a palladium catalyst (Pd / Ag on alumina, having a main θ content, based on alumina, having 0.3 wt.-% Pd, 0.1 wt.-% Ag, the EM distribution is eggshell, catalyst purchased from BASF - such a catalyst is described in WO 2006 / 040159 A1) (17.75 g, 14.06 wt%), 100 g (0.21 mol, 1 equivalent) of polyetheramine T403 and 26.6 g of butan-2-one (0.36 mol, 1.7 equivalents) were charged into a 300 mL steel pressure autoclave. The autoclave was sealed, purged with nitrogen and heated to 140 °C at atmospheric pressure. Subsequently, the autoclave was pressurized with H2 (160 bar) at the same temperature for 20 h. The autoclave was cooled and vented. The crude compound was filtered, and volatiles and water were removed under reduced pressure to obtain 98 g of a colorless, transparent liquid, which was used without any further purification.

[0490] Comparative Example 1A: Preparation of a poly(urea-carbamate) polymer according to the prior art and its recyclability test

[0491] 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) (molar ratio NCO:OH 1.00:1.00 to 1.05:1.00) was added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separation foil and cured in an oven at 105 °C for 40 min. A material in the form of a white opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0492] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (0.2 × 0.2 × 0.2 cm 3), and transfer it to a hot press. Apply a pressure of 880 kPa to the sample and press for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The sample starts to melt at about 110 °C to 120 °C and forms a cookie-shaped plate after cooling. Additional tests are disclosed in Examples 9 and 10 below.

[0493] Example 1A: Preparation of a Covalent Adaptable System (CAS) Poly(ureaurethane) Polymer According to the Invention and Testing of Its Recyclability

[0494] Heat 60.0 g of prepolymer 1a (7.94% NCO) obtained according to Reference Example 1A to 70 °C, degas and place under N2. Add 16.1 g of 4,4'-methylene-bis[N-(1-methylpropyl)-phenylamine] (DIB-MDA) (51.8 mmol) (molar ratio NCO:NH 1.00:1.00 to 1.05:1.00), and stir the mixture in a high-speed mixer at 2000 rpm for 20 seconds. Cast the obtained mixture into a silicone rubber mold lined with a separating foil and cure at 105 °C in a drying oven for 40 min. A yellow transparent solid plate material is obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0495] Recyclability test (melting). Cut a sample of the obtained plate into small cubes (about 0.2 × 0.2 × 0.2 cm 3 ), and transfer it to a hot press. Apply a pressure of 880 kPa to the sample and press for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The sample starts to melt at about 70 °C and forms a thin foil after cooling. Additional tests are disclosed in Examples 9 and 10 below.

[0496] Conclusion: The product obtained according to the invention starts to melt at a temperature of about 70 °C, far lower than that of Comparative Example 1A, and allows the formation of a thin foil - which is recyclable.

[0497] Comparative Example 1B: Preparation of a Poly(ureaurethane) Polymer According to the Prior Art

[0498] 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) (molar ratio NCO:OH 1.00:1.00 to 1.05:1.00) was added and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with release foil and cured in an oven at 105 °C for 16 h. A material in the form of a colorless transparent viscoelastic plate was obtained, which showed already flowing at room temperature. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0499] Example 1B: Preparation of a covalent adaptable system (CAS) poly(urea - urethane) polymer according to the invention

[0500] 30.0 g of prepolymer 1b (7.47% NCO) according to Reference Example 1B was heated to 70 °C, degassed and placed under N2. 8.39 g of DIB-MDA (25.4 mmol) (molar ratio NCO:NH 1.00:1.00 to 1.05:1.00) was added and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with release foil and cured in an oven at 105 °C for 40 min. A material in the form of a yellow transparent viscoelastic plate was obtained, which showed already flowing at room temperature. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0501] Comparative Example 1C: Preparation of a poly(urea - urethane) polymer according to the prior art and its recyclability test

[0502] 30.0 g of prepolymer 1c (7.15% NCO) according to Reference Example 1C was mixed with 2.19 g of BDO (24.2 mmol) (molar ratio NCO:OH 1.05:1.00) and stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with release foil and cured in an oven at 105 °C for 90 min. A material in the form of a slightly brown opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0503] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples did not melt at temperatures up to 180 °C.

[0504] Example 1C: Preparation of a Covalent Adaptable Network (CAN) Poly(ureaurethane) Polymer According to the Invention and Testing of Its Recyclability

[0505] 30.0 g of prepolymer 1c (7.15% NCO) according to Reference Example 1C was mixed with 8.03 g of DIB-MDA (24.2 mmol) (molar ratio NCO:OH 1.05:1.00) and stirred in a high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 90 min. A material in the form of a slightly brown opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0506] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (ca. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. The samples were pressed under a pressure of 880 kPa for at least 5 min (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples started to melt at ca. 160 °C and formed thin foils after cooling.

[0507] Conclusion: Contrary to Comparative Example 1C, the product obtained according to the invention was able to melt and allowed the formation of thin foils - it is recyclable.

[0508] Comparative Example 1D: Preparation of a Poly(ureaurethane) Polymer According to the Prior Art and Testing of Its Recyclability

[0509] 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 high-speed mixer at 2000 rpm for 20 s. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 90 min. A material in the form of a grayish-white opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0510] Recyclability test (melting). Samples of the obtained plates were cut into small cubes (ca. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. The samples were pressed under a pressure of 880 kPa for at least 5 min (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples did not melt at temperatures up to 180 °C.

[0511] Example 1D: Preparation of a Covalent Adaptable Network (CAN) Poly(ureaurethane) Polymer According to the Invention and Testing of Its Recyclability

[0512] 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 high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a slightly opaque yellow solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0513] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples started to melt at about 140 °C and formed a thin foil after cooling.

[0514] Conclusion: Contrary to Comparative Example 1D, the product obtained according to the invention is capable of melting and allows the formation of a thin foil - it is recyclable.

[0515] Comparative Example 2: Preparation of a Poly(ureaurethane) Polymer According to the Prior Art and Testing of Its Recyclability

[0516] 30.0 g of prepolymer 2 (7.50% NCO) obtained according to Reference Example 2 and 2.30 g of BDO (25.3 mmol) (molar ratio NCO:OH was 1.00:1.00 to 1.05:1.00) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a white opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0517] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples did not melt at temperatures up to 180 °C.

[0518] Recyclability test (extrusion). To test the extrusion properties, a sample of the obtained plate was cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), and it was transferred to an extruder. The sample was extruded at 200 °C, and it did not melt, and the material clogged the extruder. When the extrusion chamber was opened, the material was regained as a brittle solid.

[0519] Example 2: Preparation of a covalently adaptable network (CAN) poly(ureaurethane) polymer according to the invention and its recyclability test

[0520] 30.0 g of prepolymer 2 (7.50% NCO) obtained according to Reference Example 2 and 8.43 g of DIB-MDA (25.5 mmol) (molar ratio NCO:NH 1.00:1.00 to 1.05:1.00) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0521] Recyclability test (melting). A sample of the obtained plate was cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), and it was transferred to a hot press. A pressure of 880 kPa was applied to the sample and pressed for at least 5 minutes (a force of 20 kN was applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The sample started to melt at about 100 °C and formed a thin foil after cooling.

[0522] Conclusion: Contrary to Comparative Example 2, the product obtained according to the invention can be melted and allows the formation of a thin foil - it is recyclable.

[0523] Recyclability test (extrusion). To test the extrusion properties, a sample of the obtained plate was cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), and it was transferred to an extruder. The sample was extruded at 180 °C. At this temperature, the sample could be extruded as a homogeneous, flowable paste with a maximum torque of 2.2 kNm.

[0524] Conclusion: Contrary to Comparative Example 2, the product obtained according to the invention can be extruded and allows the formation of a homogeneous paste - it is recyclable.

[0525] Comparative Example 3: Preparation of a poly(ureaurethane) polymer according to the prior art

[0526] 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) (molar ratio NCO:OH is 1.05:1.00) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a slightly yellow transparent solid plate was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0527] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ), and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples did not melt at temperatures up to 180 °C.

[0528] Example 3: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the present invention

[0529] 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) prepared as described in Reference Example 3 (molar ratio NCO:NH is 1.05:1.00) were added, and the mixture was stirred in a high - speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid was obtained. The characteristics of the obtained material are recorded in Tables 1 and 2.

[0530] Recyclability test (melting). Samples of the obtained plate were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ), and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples started to melt at about 100 °C and formed a thin foil after cooling.

[0531] Conclusion: Contrary to Comparative Example 3, the product obtained according to the present invention can be melted and allows the formation of a thin foil - it is recyclable.

[0532] Properties / Recyclability of the Materials Prepared in Table 2

[0533]

[0534]

[0535] Example 4: Preparation of a Composite Material According to the Invention Containing Glass Fibers

[0536] 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) (NCO:NH molar ratio 1.05:1.00) was added. The mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. Subsequently, 300 mg of single glass fibers were stirred in as a filler material. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 40 min. A material in the form of a yellow opaque plate was obtained.

[0537] Example 5: Mechanical Recycling

[0538] The material obtained from Example 4 was cut and pressed at 880 kPa at 140 °C for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). As a result, a thin foil was obtained, showing that the composite material is mechanically recyclable.

[0539] Example 6: Mechanical Recycling Test of the Composite Material According to the Invention

[0540] A sample of the yellow opaque solid plate obtained according to Example 2 was cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. The sample was pressed at 880 kPa at 140 °C for at least 5 minutes to obtain a thin foil (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). Single glass fibers were placed between two foils, and the structure was pressed at 880 kPa at 140 °C for at least 5 minutes to obtain a composite material in the form of a thin foil (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method).

[0541] Recycling Test: The obtained composite material in the form of a thin foil was cut into pieces and these pieces were pressed at 880 kPa at 140 °C for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). As a result, a thin foil was obtained, showing that the composite material is mechanically recyclable.

[0542] Example 7: Chemical recycling of the composite material according to the invention

[0543] 22.0 g of the composite material according to Example 4 was immersed in 150 mL of dry toluene and heated to reflux with stirring. After 4 h, before the resin was completely dissolved, the material began to swell. When the solution was cooled, the mixture underwent a sol-gel transition, which was reversible when heated again. Then, the dissolved gel was hot-filtered, and the glass fibers were filtered out.

[0544] The filtrate was collected in a flask. The filtrate was gelled and dried first in a rotary evaporator at 120 °C and 50 mbar under reduced pressure at an elevated temperature, and then in a vacuum oven at 80 °C.

[0545] The resulting solid was pressed at 140 °C under a pressure of 880 kPa for at least 5 minutes to obtain a thin foil (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). A single glass fiber was placed between two foils, and the structure was pressed at 140 °C under a pressure of 880 kPa for at least 5 minutes to obtain a new composite material from the recycled polymer (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The chemical recycling according to Example 7 is shown in Figure 3 in.

[0546] Example 8: Chemical recycling in the presence of an amine

[0547] Approximately 5 g of the monolithic material (poly(ureaurethane) polymer) obtained according to Example 2 was immersed in 50 mL of toluene. 2.6 g of DIB-MDA (1 equivalent relative to the reversible NCO bonds) was added to scavenge the open NCO-bonds formed by the thermal cleavage of the urethane bonds. After stirring at reflux for 16 h, the material was completely dissolved. The toluene was removed under reduced pressure to obtain a mixture containing the amine-terminated prepolymer as an uncured viscous liquid. The mixture was diluted with 1 mL of toluene, and the amine-terminated prepolymer was precipitated by adding it to 50 g of n-heptane to remove the excess DIB-MDA. The amine-terminated prepolymer was separated from the solvent and the dissolved DIB-MDA therein by decantation. Then the amine-terminated prepolymer was dried to obtain 4.51 g of an amine (DIB-MDA)-terminated prepolymer with an amine value of 75.2 mg KOH / g.

[0548] Formation of new poly(ureaurethane) polymers (monoliths): The amine (DIB-MDA)-capped prepolymer was reacted with the prepolymer of Example 2 to obtain a recycled covalent adaptable network (CAN) poly(urea-urethane) polymer, which is the same material as the monolith (poly(ureaurethane) polymer) obtained according to Example 2.

[0549] Example 9: Testing - Recycling properties of the polymers obtained in Example 1A and Comparative Example 1A

[0550] The plates obtained according to Example 1A and Comparative Example 1A were cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ).

[0551] 19.1 Approximately 5 g of a sample of the material according to Example 1A was mixed with 50 mL of toluene and heated under reflux for 16 h. The mixture was then cooled. The CAS material according to Example 1A completely dissolved in toluene, such that a homogeneous slightly yellow liquid mixture was obtained. After removal of the solvent, a transparent slightly yellow solid was obtained.

[0552] 19.2 Approximately 5 g of a sample of the material according to Comparative Example 1A was mixed with 50 mL of toluene and heated under reflux for 16 h. The mixture was then cooled. The material did not dissolve.

[0553] This example is shown in Figure 1 . Thus, it has been demonstrated by this example that, contrary to the materials of the prior art, the CAS material according to the invention is reversibly soluble in toluene, allowing its chemical recycling.

[0554] Example 10: Testing - Melting behavior of the polymers obtained in Example 1A and Comparative Example 1A

[0555] The materials obtained in Example 1A and Comparative Example 1A were cut into small cubes (approx. 0.2×0.2×0.2 cm 3 ), transferred to a hot press, and then subjected to compression molding in the hot press at 20 kN for 5 minutes at different temperatures (i.e., 80 °C, 100 °C, and 120 °C). The products obtained are shown in Figure 2 .

[0556] In the case of the material of Example 1A, a foil was obtained at 80 °C, while at 80 °C and even 100 °C, the material of the comparative example remained as a white block. At 120 °C, for the comparative example a fine white opaque plate was formed, while for the example of the invention a fine transparent foil was obtained. Thus, it was shown that the material according to the invention melts at much lower temperatures compared to common materials.

[0557] Example 11: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the invention from an aliphatic diamine

[0558] 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) (molar ratio NCO:NH 1.05:1.00) were added, and the mixture was stirred in a high - speed mixer at 2000 rpm for 20 s. The mixture immediately became solid and was cured at 105 °C for 1 h and at room temperature for 48 h to obtain an off - white opaque material.

[0559] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (0.2×0.2×0.2 cm 3 ) and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples started to melt at about 100 °C and formed circular plates after cooling.

[0560] Recyclability test (solution, toluene). 2 g of the plate obtained from the melt test were cut into small cubes (0.2×0.2×0.2 cm 3 ) and immersed in 20 mL of toluene. The mixture was heated to 110 °C for 24 h. The sample did not dissolve.

[0561] Recyclability test (solution, DMI). 2 g of the obtained plate were cut into small cubes (0.2×0.2×0.2 cm3) and immersed in 20 mL of 1,3 - dimethyl - 2 - imidazolidinone. The mixture was heated to 130 °C for 24 h. The sample completely dissolved to give a clear solution.

[0562] Higher temperatures are required to recycle polymers containing aliphatic amines according to the invention by dissolution in organic solvents.

[0563] Reference Example 4: Preparation of the prepolymer

[0564] 20 g of 4,4′ - methylene - bis - (phenyl isocyanate) (MDI, functionality 2) (0.080 mol) and 20 g of Lupranat M20 FB (pMDI, functionality approximately 2.5) (0.06 mol) were immersed in a flask and placed under N2. The mixture was heated, and when the MDI melted, 0.02 g of benzoyl chloride (141 μmol) was added. 82.6 g of polytetrahydrofuran (polyTHF) (f = 2, M n= 2000 g / mol, #OH = 55 mg KOH / g) was melted and slowly added to the MDI / pMDI mixture at 80 °C. When the NCO value reached <8% (the molar ratio of NCO:OH was approximately 1:0.3), the reaction was terminated by cooling. A prepolymer in the form of a yellow clear liquid was obtained.

[0565] Example 12: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the invention from N-(2 - hydroxyethyl)aniline

[0566] 15.0 g of the prepolymer according to Reference Example 4 (7.3% NCO) and 1.70 g of N-(2 - hydroxyethyl)aniline (12.4 mmol) (molar ratio NCO:XH 1.05:1.00, where X is the sum of O and N) were added, and the mixture was stirred in a high - speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a separating foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained.

[0567] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (0.2×0.2×0.2 cm 3 ) and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples started to melt at about 180 °C and formed cookie - shaped plates after cooling.

[0568] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2×0.2×0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N - butylamine was added to scavenge the open NCO bonds. The mixture was heated to 110 °C. The sample completely dissolved, but a turbid solution was obtained.

[0569] Recyclability test (solution, DMI). 3 g of the obtained plate was cut into small cubes (0.2×0.2×0.2 cm 3 ) and immersed in 30 mL of 1,3 - dimethyl - 2 - imidazolidinone. 1 g of N - butylamine was added to scavenge the open NCO bonds. The mixture was heated to 120 °C. The sample completely dissolved after 1 h to give a clear solution.

[0570] Example 13: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer according to the invention from 2-(ethylamino)ethanol

[0571] 15.0 g of the prepolymer according to Reference Example 4 (7.3% NCO) and 1.10 g of 2-(ethylamino)ethanol (12.8 mmol) (molar ratio NCO:XH 1.05:1.00, X = sum of O and N) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained.

[0572] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and transferred to a hot press. A pressure of 880 kPa was applied to the samples for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The samples started to melt at about 150 °C and formed cookie-shaped plates after cooling.

[0573] Recyclability test (solution, toluene): 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 13 mL of toluene. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 110 °C. The sample did not dissolve but swelled.

[0574] Recyclability test (solution, DMI). 3 g of the obtained plate was cut into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immersed in 30 mL of 1,3-dimethyl-2-imidazolidinone. 1 g of N-butylamine was added to scavenge the open NCO bonds. The mixture was heated to 120 °C. The sample completely dissolved after 4 h to give a clear solution.

[0575] Comparative Example 14: Preparation of a covalently adaptable network (CAN) poly(urea - urethane) polymer from 1,4 - butanediol

[0576] 15.0 g of the prepolymer according to Reference Example 4 (7.3% NCO) and 1.12 g of 1,4 - butanediol (12.4 mmol) (molar ratio NCO:XH 1.05:1.00, X = O) were added, and the mixture was stirred in a high-speed mixer at 2000 rpm for 20 seconds. The mixture was cast into a silicone rubber mold lined with a release foil and cured in an oven at 105 °C for 90 min. A material in the form of a yellow opaque solid plate was obtained.

[0577] Recyclability test (melt). Samples of the obtained plate were cut into small cubes (approx. 0.2 × 0.2 × 0.2 cm 3), and transfer it to a hot press. Apply a pressure of 880 kPa to the sample and press for at least 5 minutes (a force of 20 kN applied in a circular press with a diameter of 17 cm according to the above melting point analysis method). The sample does not melt at temperatures up to 180 °C.

[0578] Recyclability test (solution, toluene): Cut 3 g of the obtained plate into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immerse them in 13 mL of toluene. Add 1 g of N-butylamine to scavenge the open NCO bonds. Heat the mixture to 110 °C. The sample does not dissolve.

[0579] Recyclability test (solution, DMI). Cut 1 g of the obtained plate into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immerse them in 10 mL of 1,3-dimethyl-2-imidazolidinone. Add 0.33 g of N-butylamine to scavenge the open NCO bonds. Heat the mixture to 120 °C. The sample does not dissolve after 7 h, and the sample swells in the solvent.

[0580] Comparative Example 15: Prepared according to WO 2022189242

[0581] Dissolve 16.5 g of pMDI in THF and cool to 0 °C. With stirring, drop DIB-MDA (20.23 g) in THF into the pMDI / THF solution. Stir the reaction mixture at 0 °C for 1 h, and then slowly heat to reflux for 6 h. Remove the solvent, and cure the sample at 140 °C for 24 h. Obtain product 15a as a yellow solid.

[0582] Recyclability test (solution, toluene). Cut 3 g of solid 15a into small cubes (0.2 × 0.2 × 0.2 cm 3 ) and immerse them in 30 mL of toluene. Heat the mixture to 110 °C for 4 h. The sample does not dissolve.

[0583] Immerse 3 g of plate 15a in 30 mL of toluene and add 0.9 g of 1,4-butanediol (2.00 equivalents of OH butanediol / equivalent of HUB in the plate). Stir the mixture under reflux for 24 h. After this time, the material swells but does not dissolve.

[0584] Cut 3 g of 15a into pieces and immerse them in a small amount of toluene (5 mL), add 0.4 g of diisopropylamine. Heat the mixture under reflux for 8 h. The cubes dissolve and a yellow liquid is obtained.

[0585] Immerse a 3 g plate 15a in 30 mL of toluene and add 0.4 g of DIB-MDA (0.25 equivalents of SHA DIB-MDA / equivalent of HUB in the plate). Stir the mixture under reflux overnight. When cooled, the mixture did not gel. When the solvent was removed, a viscous liquid that was still soluble in THF was obtained. Description of the Drawings

[0586] Figure 1 Shows different steps related to the test of the recycling characteristics of the plates obtained in Comparative Example 1A and Example 1A. 1. Shredding / cutting; 2. Addition of toluene; 3. Heating for 16 h, followed by cooling; 4. Removal of toluene.

[0587] Figure 2 Shows the test results after compression molding of Example 1A and Comparative Example 1A at different temperatures. The arrows show that the comparative example only obtained small pieces at 80 °C and 100 °C, indicating no melting at these temperatures, while a foil was already obtained at 80 °C with the material of Example 1A.

[0588] Figure 3 Shows different steps related to the test of the recycling characteristics of the plates obtained in Comparative Example 2 and Example 2. 1. Shredding / cutting; 2. Addition of toluene; Heating for 16 h, followed by cooling;

[0589] Figure 4 Shows the test results after compression molding of Example 2 and Comparative Example 2 at different temperatures. Comparative Example 2 did not melt at all at temperatures up to 180 °C, while Example 2 melted at about 130 °C

[0590] Figure 5 Shows different steps related to the test of the recycling characteristics of the composite material of Example 4. 1. Add toluene to the block of the composite material of Example 4 and heat under reflux for 16 h; 2. Hot filtration; a: Separated glass fibers, b: Gel the filtrate and dry; 3. Press b at 880 kPa at 140 °C for 5 min (apply a force of 20 kN in a circular press with a diameter of 17 cm according to the above melting point analysis method) to obtain a thin foil, 4. Recycled composite material with glass fibers obtained by pressing glass fibers between two foils.

[0591] Cited Literature

[0592] - Kunststoffhandbuch [Plastics handbook], Volume 7, Polyurethane [Polyurethanes], Carl Hanser Verlag, 3rd edition, 1993, Chapters 3.1, 3.2 and 3.3.2

[0593] -Ullmann’s Encyclopedia of Industrial Chemistry][Encyclopedia of Ullmann's Industrial Chemistry], 4th Edition, Volume 19, pages 62 to 65

[0594] -WO 2006 / 040159 A1

Claims

1. A poly(urea - urethane) polymer obtainable or obtained by a process comprising the following: - Reacting the following components: (i) At least one isocyanate; (ii) At least one polyol; and (iii) At least one secondary amine having the following formula (I): where -R a - is selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z 10 -, -Z 11 -, -Z 13 -, -Z1 - Z5-, -Z5 - Z1 - Z5-, -Z1 - Z6-, -Z1 - Z7-, -Z1 - Z8-, -Z1 - Z9-, -Z9 - Z1 - Z9-, -Z1 - Z 10 -, -Z3 - Z5-, -Z3 - Z6-, -Z3 - Z7-, -Z3 - Z8-, -Z3 - Z9-, -Z3 - Z 10 -, -Z1 - Z5 - Z1-, -Z1 - Z9 - Z1-, -Z9 - Z1(-Z 11 -Z1) n -Z9 - —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1 - Z 12 -Z1-; where -Z1- is a substituted or unsubstituted, straight - chain or branched C1 - C 30 alkylene; -Z2- is a substituted or unsubstituted, straight - chain or branched 2 - to 300,000 - membered heteroalkylene; -Z3- is a substituted or unsubstituted, straight - chain or branched C2 - C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight - chain or branched 3 - to 30 - membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5 - C 30 cycloalkylene; -Z6- is a substituted or unsubstituted 5 - to 30 - membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5 - C 30 cycloalkenylene; -Z8- is a substituted or unsubstituted 5 - to 30 - membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6 - C 30 arylene; -Z10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene; -Z 11 - is a C6-C arylene substituted with -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10 -Z 12 - is -N(R f )-; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkyl, where at least one of the one or more heteroatoms of Z 13 comes from X a ; where C a is a C atom or an H atom and C b is a C atom or an H atom, where at least one of C a and C b is a C atom; where X a is an O atom or NH and X b is an O atom or NH, where at least one of X a and X b is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom; where (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, straight-chain or branched, substituted or unsubstituted C1-C 30 alkyl, straight-chain or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, straight-chain or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 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 10Alkylene C5-C 30 Cycloalkenyl, C1-C substituted or unsubstituted 10 Alkylene 5- to 30-membered heterocycloalkyl, C1-C substituted or unsubstituted 10 Alkylene 5- to 30-membered heterocycloalkenyl, C1-C substituted or unsubstituted 10 Alkylene C6-C 30 Aryl and C1-C substituted or unsubstituted 10 Alkylene 5- to 30-membered heteroaryl, R b and R e are each independently as defined for R c , R d , R f and R g ; or There is no R b and R e , and C a and C b are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or (B)C a and R e form a C6-C substituted or unsubstituted 30 arylene, and there is no R f and R g both; and C b and R b form a C6-C substituted or unsubstituted 30 arylene, and there is no R c and R d both; or (C)-C a and R e form a C6-C substituted or unsubstituted 30 arylene, and there is no R f and R g both; or -C b and R b form a C6-C substituted or unsubstituted 30 arylene, and there is no R c and R d both; wherein, When C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently defined as any one of R c , R d , R f and R g as defined below in (A); Wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in any one of (A) below.

2. The poly(urea - urethane) polymer according to claim 1, wherein,X a is NH, X b is NH, and the secondary amine (iii) has the following formula (II) where C a and C b and R b and R c and R d and R e and R f and R g and -R a - are as defined in formula (I).

3. The poly(urea - urethane) polymer according to claim 1 or 2, wherein, -R a -Selected from the group consisting of: -Z1-, -Z2-, -Z5-, -Z9-, -Z 10 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z9-Z1-Z9-, -Z1-Z5-Z1-, -Z1-Z9-Z1- and -Z9-Z1(-Z 11 -Z1) n -Z9, where n = 1, 2, 3, 4, 5, or 6.

4. The poly(urea - urethane) polymer according to any one of claims 1 to 3, wherein, R c , R d , R f and R g are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isopentyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinanyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, cyclohexyl(phenyl)methyl and -C(OH)HR k , wherein R k is selected from the group consisting of: hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl.

5. The poly(urea - urethane) polymer according to any one of claims 1 to 4, wherein, R b and R e are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, dodecyl, sec-butyl, tert-butyl, sec-isoamyl, 2-pentyl, 2-methyl-4-pentyl, 3-pentyl, 2-methyl-pentyl, 2,6-dimethyl-4-heptyl, 3-pinan-alkyl-methyl, cyclopentyl, cyclohexyl, dicyclohexylmethyl, cyclohexylmethyl, cyclododecyl, phenyl, benzyl, and cyclohexyl(phenyl)methyl.

6. The poly(urea - urethane) polymer according to any one of claims 1 to 5, wherein, R b , R c and R d Any one of them is H, and R e , R f and R g Any one of is H; wherein, except for the one that is H, R b , R c and R d is one of CH3, and except for the one that is H, R e , R f and R g is one of CH3.

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

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

10. The poly(urea - urethane) polymer according to any one of claims 1 to 7, wherein, The at least one secondary amine (iii) is a sec-butyl-modified polyetheramine having the 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, where 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.

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 diphenyl diisocyanate (mMDI), polymethylene polyphenylene polyisocyanate (pMDI), a mixture of monomeric methylene diphenyl diisocyanate and polymethylene polyphenylene polyisocyanate (MDI), toluene diisocyanate (TDI), isomers of xylylene diisocyanate (XDI), isomers of diisocyanatobenzene, dimethylbenzene 2,6 - diisocyanate, naphthalene 1,5 - diisocyanate (1,5 - NDI), butane 1,4 - diisocyanate, pentane 1,5 - diisocyanate (PDI), hexane 1,6 - diisocyanate (HDI), octane 1,8 - diisocyanate, nonane 1,9 - diisocyanate, decane 1,10 - diisocyanate, 2,2 - dimethylpentane 1,5 - diisocyanate, 2 - methylpentane 1,5 - diisocyanate (MPDI), 2,4,4(or 2,2,4) - trimethylhexane 1,6 - diisocyanate (TMDI), cyclohexane 1,3 - and 1,4 - diisocyanate, 1 - isocyanato - 3,3,5 - trimethyl - 5 - isocyanatomethylcyclohexane (IPDI), methylene - bis(isocyanatocyclohexane) (H12MDI), 2,4 - or 2,6 - diisocyanato - 1 - methylcyclohexane (H6TDI), 1 - isocyanato - 1 - methyl - 4(3) - isocyanatomethylcyclohexane (AMCI), 1,3 - bis(isocyanatomethyl)cyclohexane, 1,4 - bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)norbornane (NBDI), triphenylmethane - 4,4',4" - triisocyanate, toluene - 2,4,6 - triyltriisocyanate, ethyl ester 1 - lysine triisocyanate, triisocyanatocyclohexane, tris(isocyanatomethyl)cyclohexane, triisocyanatomethylcyclohexane, 1,8 - diisocyanato - 4 - (isocyanatomethyl)octane, undecane 1,6,11 - triisocyanate, 1,7 - diisocyanato - 4 - (3 - isocyanatopropyl)heptane, 1,6 - diisocyanato - 3 - (isocyanatomethyl)hexane, 2,2 - bis[[4 - (isocyanatomethyl)phenyl]methyl]butyl n - [[4 - (isocyanatomethyl)phenyl]methyl]carbamate, (2,4,6 - trioxotriazine - 1,3,5(2h,4h,6h) - triyl)tri(hexamethylene) isocyanate, 1,3,5 - triisocyanatobenzene, tris(isocyanatohexyl)biuret, 3,3',3" - [(1h,3h,5h) - 2,4,6 - trioxo - 1,3,5 - triazine - 1,3,5 - triyltri(methylene)]tris[3,5,5 - trimethylcyclohexyl]triisocyanate, 1,3,5 - triazine - 2,4,6 - triisocyanate, 2,4,4' - triisocyanato - dicyclohexylmethane, triisocyanate triphenyl thiophosphate, 2,4,4' - diphenyl ether triisocyanate, 1,3 - bis(3 - isocyanato - 4 - methylphenyl) - 1,3 - diazetidine - 2,4-diketones and mixtures of two or more thereof., 12. The poly(urea - urethane) polymer according to any one of claims 1 to 11, wherein, The at least one polyol (i) is selected from the group consisting of polyester polyols, polyether ester polyols, polycarbonate polyols, polyacrylate polyols, polyolefin polyols, polyether polyols, and mixtures of two or more thereof.

13. A composite material based on a poly(urea - urethane) polymer, which can be obtained or has been obtained by a method comprising the following: - Reacting the following components: (i) At least one isocyanate; (ii) At least one polyol; and (iii) At least one secondary amine having the following formula (I): where -R a - Selected from the group consisting of: -Z1-, -Z2-, -Z3-, -Z4-, -Z5-, -Z6-, -Z7-, -Z7-, -Z8-, -Z9-, -Z10 -, -Z 11 -, -Z 13 -, -Z1-Z5-, -Z5-Z1-Z5-, -Z1-Z6-, -Z1-Z7-, -Z1-Z8-, -Z1-Z9-, -Z9-Z1-Z9-, -Z1-Z 10 -, -Z3-Z5-, -Z3-Z6-, -Z3-Z7-, -Z3-Z8-, -Z3-Z9-, -Z3-Z 10 -, -Z1-Z5-Z1-, -Z1-Z9-Z1-, -Z9-Z1(-Z 11 -Z1) n -Z9 —— where n = 1, 2, 3, 4, 5, or 6 —— and -Z1-Z 12 -Z1-; where -Z1- is a substituted or unsubstituted, straight-chain or branched C1-C 30 alkylene; -Z2- is a substituted or unsubstituted, straight-chain or branched 2- to 300,000-membered heteroalkylene; -Z3- is a substituted or unsubstituted, straight-chain or branched C2-C 30 alkenylene; -Z4- is a substituted or unsubstituted, straight-chain or branched 3- to 30-membered heteroalkenylene; -Z5- is a substituted or unsubstituted C5-C 30 cycloalkylene; -Z6- is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene; -Z7- is a substituted or unsubstituted C5-C 30 cycloalkenylene; -Z8- is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylene; -Z9- is a substituted or unsubstituted C6-C 30 arylene; -Z 10 - is a substituted or unsubstituted 5- to 30-membered heteroarylene; -Z 11 - is an arylene substituted by -NHR or -OR, where R is selected from the group consisting of H and substituted or unsubstituted, straight-chain or branched C1-C 30 alkyl; 10 -Z 12 - is -N(R f )-; -Z 13 - is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, where at least one of one or more heteroatoms of Z 13 is from X​a ; where C a is a C atom or an H atom and C b is a C atom or an H atom, where C a and C b at least one of them is a C atom; where X a is an O atom or NH and X b is an O atom or NH, where X a and X b at least one of them is NH, provided that for X a and / or X b is NH, the corresponding C a and / or C b is a C atom; where (A) R c , R d , R f and R g are each independently selected from the group consisting of: hydrogen, linear or branched, substituted or unsubstituted C1-C 30 alkyl, linear or branched, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkyl, substituted or unsubstituted C1-C 10 alkylene C5-C 30 cycloalkenyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C 10 alkylene C6-C 30 aryl and substituted or unsubstituted C1-C 10 alkylene 5- to 30-membered heteroaryl, R b and R e are each independently as R c , R d , Rf and R g Definition; or Without R b and R e , and C a and C b Are connected to each other via a single bond to form a heterocycle composed of C a , C b , X a , X b and R a ; or (B) C a and R e Form a substituted or unsubstituted C6-C 30 Arylene, and without R f and R g Both; and C b and R b Form a substituted or unsubstituted C6-C 30 Arylene, and without R c and R d Both; or (C) -C a and R e Form a substituted or unsubstituted C6-C 30 Arylene, and without R f and R g Both; or -C b and R b Form a substituted or unsubstituted C6-C 30 Arylene, and without R c and R d Both; Wherein, When C a and R e form a substituted or unsubstituted C6-C 30 arylene, R b , R c and R d are each independently as defined for R c , R d , R f and R g in any one of (A); wherein, when C b and R b form a substituted or unsubstituted C6-C 30 arylene, R e , R f and R g are each independently as defined for R c , R d , R f and R g in (A) below, Obtain a mixture comprising a poly(ureaurethane) polymer, preferably the poly(ureaurethane) polymer according to claims 1 to 11, - contacting the obtained mixture with (iv): (iv) a filler selected from the group consisting of glass fibers, carbon fibers, mineral fibers, textiles, metal meshes, metal fibers, metal rods, carbonates, wood, and mixtures of two or more thereof.

14. A method for preparing a poly(urea - urethane) polymer according to any one of claims 1 to 12, the method comprising: (a) React at least one isocyanate (i) with at least one polyol (ii) to obtain a prepolymer; (b) Contact the prepolymer obtained in (a) with at least one secondary amine to obtain the poly(ureaurethane) polymer, the at least one secondary amine having the formula (I) as defined in any one of claims 1 to 10; or (a') React at least one isocyanate (i) with at least one secondary amine to obtain a prepolymer, the at least one secondary amine having the formula (I) as defined in any one of claims 1 to 10; (b') Contact the prepolymer obtained in (a') with at least one polyol (ii) to obtain the poly(ureaurethane) polymer.

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

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

17. A method for shaping the poly(urea - urethane) polymer according to any one of claims 1 to 12 or the poly(urea - urethane) polymer obtainable or obtained by the method according to claim 13, the method comprising: Shape the poly(ureaurethane) polymer, wherein shaping the polymer comprises (x) applying pressure and heat to the poly(ureaurethane) polymer to obtain a shaped body, or (x') extruding the poly(ureaurethane) polymer to obtain a shaped body.

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