Process for the synthesis of functionalized cleavable amines by cyanoethylation followed by hydrogenation

Abstract

A process for preparing polyamines via (meth)acrylonitrile and / or crotononitrile addition to an amine followed by hydrogenation in the presence of a catalyst and hydrogen and optionally in the additional presence of ammonia, primary and / or secondary amine, comprises a) reacting at least one amine of general formula (I) with (meth)acrylonitrile and / or crotononitrile, thereby obtaining at least one first intermediate (I1), b) hydrogenating the at least one first intermediate (I1) to at least one polyamine compound (II), or hydrogenating the at least one first intermediate (I1) in the additional presence of ammonia, primary and / or secondary amine.

Description

Process for the synthesis of functionalized cleavable amines by cyanoethylation followed by hydrogenationThe present invention relates to a process for preparing polyamines via (meth)acrylonitrile and / or crotononitrileaddition to an amine followed by hydrogenation in the presence of a catalyst and hydrogen and optionally in theadditional presence of ammonia, primary and / or secondary amine. Further, the present invention relates to anintermediate which is obtainable or obtained by said process and a polyamine compound which is obtainable or obtained by said process. Yet further, the present invention relates to the use of said polyamine compound,containing at least one primary or secondary amine group, in or as co-reactant, hardener or curative for epoxy resinsand an epoxy resin composition containing such polyamine compound. Still further, the present invention relates to the use of said polyamine compound in specific applications. The recycling of products or materials containing epoxy resins is still unsatisfactory since no commercial solutions have been realized yet and the market strives for enabling technologies. So far, the recycling of e.g. wind turbine rotor blades is still unsatisfactory and unsatisfying with regard to the epoxy system component. Furthermore, for polyamines and products derived therefrom there are no solutions yet on how to improve the biodegradability of the polymers currently used.EP 1391448 A1 describes the synthesis of functionalized amines with aliphatic backbone and no cleavablefunctionality via addition of acrylonitrile to diamines, followed by hydrogenation.EP 1955997 A1 describes the reaction of ethylene diamine with acrylonitrile in the presence of a polar protic solventfollowed by hydrogenation. CN 116003769 A describes the synthesis of polyamine-based polyethers by reacting diamino polyethers with acrylonitrile followed by hydrogenation. There is a general need for cleavable functionalities within amines for various applications. For example, customers are seeking improved recyclability of epoxy systems in wind turbine rotor blades or better biodegradable polymer additives based on polyamines. Cleavable (poly)amines potentially represent a technology for solving this problem for the first time. This invention discloses a process for producing cleavable amines and describes various compounds that can be produced usingthis process. According to this process, the functionalized cleavable amine is synthesized in a two-step process.Starting from a cleavable amine and a vinyl nitrile compound like acrylonitrile (ACN), a single or multiple Michael addition reaction is used to synthesize a single or multiple cyanoethylated product as the desired intermediate forhydrogenation. This intermediate is then subjected to catalytic hydrogenation to yield the functionalized cleavableamine. Therefore, the present invention relates to a process for preparing polyamines via (meth)acrylonitrile and / or crotononitrile addition to an amine followed by hydrogenation in the presence of a catalyst and hydrogen andoptionally in the additional presence of ammonia, primary and / or secondary amine, comprisinga) reacting at least one amine of general formula (I)with (meth)acrylonitrile and / or crotononitrile, wherein the amine of general formula (I) comprises at least one, preferably terminal, group NH which is reacted with the (meth)acrylonitrile and / or crotononitrile, thereby obtaining at least one first intermediate (I1), wherein at least one, preferably terminal, group NH of the amine of general formula (I) is converted to a group N-CH2-CHR-CN or to a group N-CHR-CH2-CN with R being H or methyl, preferably to a group N-CH2-CH2-CN;b) hydrogenating the at least one first intermediate (I1) to at least one polyamine compound (II), comprisingconverting the at least one group N-CH2-CHR-CN or group N-CHR-CH2-CN, preferably the at least one group N-CH2-CH2-CN, to at least one group N-CH2-CHR-CH2-NH2 or group N-CHR-CH2-CH2-NH2, preferably to at least one group N-CH2-CH2-CH2-NH2; or hydrogenating the at least one first intermediate (I1) in the additional presence of ammonia, primary and / or secondary amine HNR’R” with R’ being H, C1-C3-alkyl, preferably H, methyl or ethyl, R” being H, C1-C3-alkyl,preferably H, methyl or ethyl, to at least one polyamine compound (III), comprising converting the at least one group N-CH2-CHR-CN or group N-CHR-CH2-CN, preferably the at least one group N-CH2-CH2-CN, to at least one group N-CH2-CHR-CH2-NR’R” or group N-CHR-CH2-CH2-NR’R”, preferably to at least one group N-CH2- CH2-CH2-NR’R”; wherein X is C or Si or HC-CH; wherein a1, a2, b1, b2, c1, c2, d1, d2 are independently of each other 0 or 1, with a1 + b1 + c1 + d1 ≥ 2 and a2 + b2 + c2 + d2 ≥ 2; wherein, if a1 = a2 = 0, YA1is H or optionally substituted C1-C12-alkyl; wherein, if a1 = 1 and a2 = 0, YA1is optionally substituted C1-C12-alkyl;wherein, if a1 = a2 = 1, or if a1 = 0 and a2 = 1, YA1is optionally substituted C1-C12-alkylene; wherein, if b1 = b2 = 0, YB1is H or optionally substituted C1-C12-alkyl; wherein, if b1 = 1 and b2 = 0, YB1is optionally substituted C1-C12-alkyl; wherein, if b1 = b2 = 1, or if b1 = 0 and b2 = 1, YB1is optionally substituted C1-C12-alkylene; wherein, if c1 = c2 = 0, YC1is H or optionally substituted C1-C12-alkyl; wherein, if c1 = 1 and c2 = 0, YC1is optionally substituted C1-C12-alkyl; wherein, if c1 = c2 = 1, or if c1 = 0 and c2 = 1, YC1is optionally substituted C1-C12-alkylene; wherein, if d1 = d2 = 0, YD1is H or optionally substituted C1-C12-alkyl; wherein, if d1 = 1 and d2 = 0, YD1is optionally substituted C1-C12-alkyl; wherein, if d1 = d2 = 1, or if d1 = 0 and d2 = 1, YD1is optionally substituted C1-C12-alkylene; wherein RA2, RA3, RB2, RB3, RC2, RC3, RD2, RD3are, independently of each other, H or optionally substituted C1-C12- alkyl, with at least one of RA2, RA3, RB2, RB3, RC2, RC3, RD2, and RD3being H; wherein, if X is C or Si- YA1 and YB1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when a1 = b1 = 1;and / or- YC1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when c1 = d1 = 1;wherein, if X is HC-CH and (O)a1(O)b1X(O)c1(O)d1isthen- YA1 and YC1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when a1 = c1 = 1;and / or- YB1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when b1 = d1 = 1; or- YA1 and YB1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when a1 = b1 = 1;and / or- YC1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when c1 = d1 = 1.All individual steps of the process of the present invention can be carried out continuously, in batch mode or in a semi-batch mode. The term “(meth)acrylonitrile” as used herein refers to acrylonitrile, methacrylonitrile, and a mixture thereof. Compound (I) and preferably compounds (II) and (III) may comprise at least one NH group or functionality which is preferably a NH2 group or functionality but can also be a substituted group or functionality NHR. All of thesehydrogen atoms can react with the above acrylonitrile. An N-H functionality in compounds (II) and (III) makes the compound especially suitable for use in epoxy resins, as outlined below. Further preferably, if the hydrogenation according to the present invention is carried out in the presence of a secondary amine, such as dimethyl amine, acompound (III) which contains exclusively tertiary amino groups is obtained; such a compound (III) can be usedadvantageously as a PU catalyst as described herein. Polyamine compound (II) contains primary amino groups, as shown above, and can additionally contain, e.g. viabackbone substitution, -NR- or -NH-.For compounds (I), (II), (III), (I1), HNR’R”, single compounds or mixtures can be employed. In step b), in addition to hydrogen, ammonia, primary amines and / or secondary amines can be employed. The structural unit X is C or Si or HC-CH, leading to the following exemplary structures of compounds (I), (II) and (III). Starting compounds (I) can be obtained by amination of the following hydroxyl compounds with preferably ammonia or suitable amines for this reaction including monomethylamine (MMA), monoethylamine, monopropylamine and monoisopropylamine as well as the respective secondary amines like dimethylamine (DMA):Preferably, the amine of general formula (I) comprises at least two, preferably terminal, groups NH which are reactedwith the (meth)acrylonitrile and / or crotononitrile.Generally, the amine of general formula (I) can be any one of the respective compounds disclosed in WO 2012071896 A1, WO 2013007128 A1, WO 2013184827 A1, WO 201554698 A1, WO 2019240840 A1, WO 2019240841 A1, US 20190016667 A1, US 20190016870 A1, US 20220356145 A1 or US 20220024854 A1, provided that it exhibits a structure according to formula (I) of the present invention. Preferably, if a1 = 1, then a2 = 1; if b1 = 1, then b2 = 1; if c1 = 1, then c2 = 1; and if d1 = 1, then d2 = 1. Preferably, RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, more preferably H, and RA3, RB3, RC3, RD3are H, or RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, more preferably H, and RA3, RB3, RC3, RD3are methyl, or RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, more preferably H, and RA3, RB3, RC3, RD3are ethyl, or RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, more preferably H, and RA3, RB3, RC3, RD3are propyl, or RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, more preferably H, and RA3, RB3, RC3, RD3are isopropyl, or RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are methyl, or RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are ethyl, or RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are propyl, or RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are isopropyl. Preferably, if X is C, two, one or none of YA1, YB1, YC1and YD1are H, more preferably one or none of YA1, YB1, YC1and YD1is H, more preferably none of YA1, YB1, YC1and YD1is H. Preferably, if X is Si or HC-CH, none of YA1, YB1, YC1and YD1is H. Preferably, X is C and a1 + b1 + c1 + d1 = 2. Preferably, X is Si and a1 + b1 + c1 + d1 ≥ 2. Preferably, X is HC-CH and a1 + b1 + c1 + d1 = 2 or a1 + b1 + c1 + d1 = 4. Preferably, X is HC-CH and a1 + b1 + c1 + d1 = 2, wherein a1 = c1 = 1 or b1 = d1 = 1. Preferably, X is HC-CH and a1 = b1 = c1 = d1 = 1.Preferably, the amine of general formula (I), the intermediate (I1), the polyamine compound (II) and the polyaminecompound (III) do not contain halogen and sulfur atoms, do not contain aromatic groups and contain at most two heterocyclic groups. Preferably, the amine of general formula (I), the intermediate (I1), the polyamine compound (II) and the polyaminecompound (III) are formed solely of C, H, O, N, and optionally additionally one or two, preferably one, Si atom(s).Preferably, if X is C, then the amine of general formula (I), the intermediate (I1), the polyamine compound (II) and thepolyamine compound (III) have a molecular weight of at most 480 g / mol, more preferably of at most 460 g / mol, morepreferably of at most 440 g / mol. Preferably, all alkyl groups and alkylene groups present in the at least one amine of general formula (I) are non- branched groups. The carbon chain (-CH2-) therein can be interrupted by one or more non-neighboring heteroatoms, preferably O or NH or N-alkyl. More preferably, the alkyl groups and alkylene groups can contain -CH2-CH2-O- structural elements. Preferably, all alkyl groups and alkylene groups present in the at least one amine of general formula (I) are C1-C6- groups, e.g. C1, C2, C3, C4, C5, C6-groups, more preferably C1-C4-groups, e.g. methyl(ene), ethyl or 1,2-ethylene,n-propyl or 1,3-propylene, n-butyl or 1,4-butylene. These groups can be substituted or, preferably, unsubstituted.Substituents may be any charge-neutral organyl group that is formed by removing one hydrogen from a chemically stable organic molecule as defined below. It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent. Definitions Within the context of the present invention, the term “N-H functionality” is defined as follows: A primary amino group (-NH2) has two N-H functionalities, a secondary amino group only one N-H functionality, and a tertiary amino group, by consequence, has no reactive N-H functionality. The term “alkyl” as used herein encompasses both straight and branched alkyl chain radicals and can furthermore also include cycloalkyl radicals. Unless explicitly defined differently, the term “alkyl group” as used hereinencompasses groups having up to 12, up to 10, more preferably up to 6 carbon atoms, including, but not beingrestricted to, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, thealkyl group is optionally substituted, for example by halogen, preferably fluorine, or cycloalkyls. The term “cycloalkylradical” as used herein encompasses monocyclic, polycyclic, and spiroalkyl radicals. Preferred cycloalkyl groups are those containing up to 12, more preferably up to 10, more preferably from 3 to 8 ring carbon atoms, including, but not being restricted to, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Further, the cycloalkyl group may be suitably substituted, for example by halogen, deuterium, alkyl or heteroalkyl. The term “alkylene” as used herein encompasses an alkanediyl functional group, sometimes, but not necessarily, having the free valencies on adjacent carbon atoms.The term “heteroalkyl group” or “heterocycloalkyl group”, if used herein, encompasses an alkyl and a cycloalkylradical, respectively, having at least one carbon atom replaced by a heteroatom. Unless explicitly defined differently, the term “heteroalkyl group” or “heterocycloalkyl group” as used herein encompasses groups having up to 12, up to10, more preferably up to 6 carbon atoms. Preferably, the at least one heteroatom is selected from the groupconsisting of O, S, N, P, B, and Si, and is more preferably O or N. Preferably from 1 to 5, more preferably from 1 to 3,more preferably 1 or 2 heteroatoms may be present in the radical, unless explicitly defined differently herein. The radical can be covalently linked with the remainder of the molecule via a carbon or heteroatom (e.g., N). Further, the heteroalkyl or heterocycloalkyl group may be suitably substituted, for example by halogen, deuterium, alkyl or heteroalkyl.The term “alkenyl group”, if used herein, encompasses both straight and branched chain alkene radicals. Alkenylgroups are essentially alkyl groups with more than one carbon atom that include at least one carbon-carbon double bond in the alkyl chain. The term “cycloalkenyl group”, if used herein, encompasses cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring. Unless explicitly defined differently, the term “alkenyl group” or “cycloalkenyl group” as used herein encompasses groups having up to 12, preferably up to 10, more preferably up to 6 carbon atoms. Further, the alkenyl group may be suitably substituted, for example by halogen, deuterium, alkyl or heteroalkyl.The term “heteroalkenyl” if used herein encompasses an alkenyl radical having at least one, preferably from 1 to 5,more preferably 1 to 3, more preferably 1 or 2 carbon atoms replaced by a heteroatom, unless explicitly defined differently herein. Preferably, the at least one heteroatom is selected from the group consisting of O, S, N, P, B, and Si, more preferably O, S, or N. Unless explicitly defined differently, the term “heteroalkenyl group” as used herein encompasses groups having up to 12, preferably up to 10, more preferably up to 6 carbon atoms. Further, the heteroalkenyl group may be suitably substituted, for example by halogen, deuterium, alkyl or heteroalkyl.The terms “aralkyl” or “arylalkyl”, if used herein, are used interchangeably and encompass an alkyl group which issubstituted with an aryl group. Further, the aralkyl group may be suitably substituted, for example by halogen,deuterium, alkyl or heteroalkyl. The term “heterocyclic group” if used herein encompasses aromatic and non-aromatic cyclic radicals containing at least one, preferably 1 to 5, more preferably 1 to 3 heteroatoms. Preferably the at least one heteroatom is selectedfrom the group consisting of O, S, N, P, B, and Si, more preferably is O or N. The term “heteroaromatic cyclicradicals” may be used interchangeably with the term “heteroaryl”. Preferred hetero-non-aromatic cyclic groups arethose containing from 3 to 7 ring atoms including at least one hetero atom, including, but not being restricted to,cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers / thio-ethers, such astetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Further, the heterocyclic group may be optionally substituted, for example by halogen, deuterium, alkyl or aryl. The heterocyclic group can be covalently linked with the remainder of the molecule via carbon and / or heteroatoms, preferably one carbon or nitrogen atom. The heterocyclicgroup can as well be linked with two carbon and / or heteroatoms with the remainder of the molecule.The term “aryl group” if used herein encompasses both single-ring aromatic hydrocarbon groups and polycyclicaromatic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) or wherein one carbon is common to two adjoining rings wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and / or heteroaryls. Preferred aryl groups are those containing 3 to 8 aromatic carbon atoms. Especially preferred is an aryl group having 6 carbons. Suitable aryl groups include phenyl, and radialene. Most preferred is phenyl which is optionally substituted by one or more non-aromatic groups. Further, the aryl group may be substituted, for example by halogen, alkyl, heteroalkyl, or deuterium. The aryl group is connected to the remainder of the molecule via one or two carbon atoms. The term “heteroaryl” if used herein refers to and includes both single-ring aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. The heteroatoms include, but are not limited to and are preferably selected from the group consisting of O, S, N, P, B, and Si, and is more preferably O or N. Hetero-single ring aromatic systems are preferably single rings with 5 or 6 ring atoms, and the ring can have from one to five / six, preferably 1 to 3 heteroatoms. The hetero-polycyclic ring systems can have two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) or wherein one carbon is common to two adjoining rings wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls. The hetero- polycyclic aromatic ring systems can have from 1 to 5, preferably 1 to 3 heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyrrole, pyrazole, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole,benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably 1,3,4- oxadiazole, furan, thiophene, 1,2,4-triazole, 1,2,3-triazole, and pyrazole groups, from which one hydrogen atom has been removed from a hydrogen-bearing carbon or heteroatom to form the covalent link to the remainder of the molecule. The heteroaryl group with two hydrogens removed can as well be linked with two carbon and / or heteroatoms with the remainder of the molecules, in which case the heteroaryl group can be part of a larger cyclic group. Further, the heteroaryl group may be suitably substituted, for example by halogen, deuterium, alkyl or aryl. If one or more of the above-defined groups are substituted, preferred substituents may be selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. In some instances, the preferred general substituents may be selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof. In yet other instances, the preferred substituents may be selected from the group consisting of halogen, alkyl, aryl, heteroalkyl, heteroaryl, alkenyl, cycloalkyl, heterocyclic groups, or of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. Generally, the terms “substituted” and “substitution” if used herein refer to a substituent otherthan H that is bonded to the relevant position, for example a carbon atom or a nitrogen atom. For example, when αrepresents mono-substitution, then one α must be other than H (i.e., a substitution). Similarly, when α represents di-substitution, then two of α must be other than H. Similarly, when α represents no substitution, α, for example, can bea hydrogen for available valencies of straight or branched chain or ring atoms, as in carbon atoms for benzene andthe nitrogen atom in pyrrole, or simply represents nothing for ring atoms with fully filled valencies, e.g., the nitrogenatom in pyridine. The maximum number of substitutions possible in a straight or branched chain or ring structuregenerally depends on the total number of available valencies in the ring atoms or number of hydrogen atoms that canbe replaced. All residues and substituents are selected in a way that a chemically stable and accessible chemicalgroup results. Generally, any type of substituent may replace a hydrogen atom in an organic or heterorganic group ofcompound (I) or compound (II) or compound (III), as long as it results in a chemical compound which is stable under conditions of steps (a) and (b) and which does not chemically react with other compounds and components of the process. In some instances, a pair of adjacent residues can be optionally joined (i.e., covalently linked with each other) or fused into a ring. The preferred ring formed therewith is a five-, six-, or seven-membered carbocyclic or heterocyclicring, including both instances where the portion of the ring formed by the pair of substituents is saturated and wherethe portion of the ring formed by the pair of substituents is unsaturated. As used herein, “adjacent” means that the two substituents involved can be on the same ring next to each other, or on two neighboring rings having the two closest available substitutable positions, such as 2,2′ positions in a biphenyl, or 1,8 position in a naphthalene, or 2,3-positions in a phenyl, or 1,2-positions in a piperidine, as long as they can form a stable fused ring system. In some instances, a pair of non-adjacent substituents can be optionally joined usually by an, at least partial, alkane or heteroalkene chain of atoms, thereby forming another macrocyclic ring system as part of the macrocyclic ring present as part of the coordination compound. In some instances, a pair of substituents present on the same carbon atom can be optionally joined, i.e., into an aryl or heteroaryl group, thus, forming a spiro linkage on said particular carbon atom.The term “organyl”, if used herein, refers to any chemically stable organic arrangement of atoms where one or morehydrogen atom have been removed such as to use those free vacancies to covalently link the organic group withanother molecular entity. Thus, the term “organyl” encompasses the majority of the above defined organic groups, forexample alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl,heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof with the number of carbon atoms and heteroatoms asdefined above for the respective term. The term “organyl” shall especially as well encompass sufficiently chemicallystable negatively charged species, such as anions, or anionic side groups.The terms “halo,” “halogen,” and “halide”, if used herein, are used interchangeably and refer to fluorine, chlorine,bromine, and iodine.According to the present invention, it is especially preferred that in the compounds (I), (I1), (II) and (III), there are nosubstituents. Step a) Preferably, reacting at least one amine of general formula (I) according to a) is carried out in the presence of at least one polar protic solvent, preferably comprising one or more of water and an alcohol, more preferably comprising one or more of water and methanol, more preferably comprising methanol, more preferably being methanol. Further preferably, the molar ratio of the at least one polar protic solvent to the at least one amine of general formula (I) is in the range of from 0.05 to 5, more preferably in the range of from 0.5 to 4, more preferably in the range of from 1.5 to 3.0, more preferably in the range of from 2.5 to 3.0. Alternatively further preferably, the molar ratio of the at least one polar protic solvent to the at least one amine of general formula (I) is in the range of from 0.05 to 5, more preferably in the range of from 0.1 to 2.0, more preferably in the range of from 0.15 to 1.0, more preferably in the range of from 0.2 to 0.5, more preferably in the range of from 0.25 to 0.35.Further preferably, the at least one polar protic solvent is present in an amount effective to increase the linear selectivityof the (meth)acrylonitrile and / or crotononitrile addition to the at least one amine of general formula (I). Preferably, thiseffect on the linear selectivity is particularly relevant for the following compounds:Preferably, reacting at least one amine of general formula (I) according to a) is carried out at a temperature in the range of from 10 to 150 °C, more preferably in the range of from 20 to 100 °C, more preferably in the range of from 30 to 80 °C. Preferably, reacting at least one amine of general formula (I) according to a) is carried out at a pressure in the rangeof from 0.8 to 1.2 bar(abs), more preferably in the range of from 0.9 to 1.1 bar(abs), more preferably at ambientpressure 1.0 bar(abs).Preferably, for reacting at least one amine of general formula (I) according to a), the at least one amine of general formula (I) and the (meth)acrylonitrile and / or crotononitrile are employed at a molar ratio of the (meth)acrylonitrile and / or crotononitrile relative to the reactive amino groups of the at least one amine of general formula (I) in the range of from 0.80 to 1.25, more preferably in the range of from 0.90 to 1.15, more preferably in the range of from 1.00 to 1.05.In particular, step a) can be carried out in continuous mode, in batch mode, or in semi-batch mode.Step b) Preferably, hydrogenating the at least one first intermediate (I1) in the additional presence of ammonia, primaryamine HNR’R” and / or secondary amine HNR’R” to at least one polyamine compound (III) according to b) is carriedout at a molar ratio of ammonia, primary and / or secondary amine HNR‘R‘‘ to cyano groups in the intermediate (I1) in the range of from 0.1 to 40, more preferably in the range of from 0.5 to 20, more preferably in the range of from 1.0 to 10.Preferably, hydrogenating the at least one first intermediate (I1), optionally in the additional presence of ammonia,primary amine HNR’R” and / or secondary amine HNR’R”, to at least one polyamine compound (II) or (III) according tob) is carried out at a temperature in the range of from 20 to 200 °C, more preferably in the range of from 40 to 160 °C, more preferably in the range of from 50 to 140 °C.Preferably, hydrogenating the at least one first intermediate (I1), optionally in the additional presence of ammonia,primary amine HNR’R” and / or secondary amine HNR’R”, to at least one polyamine compound (II) or (III) according tob) is carried out at a pressure in the range of from 1 to 325 bar(abs), more preferably in the range of from 10 to 200 bar(abs), more preferably in the range of from 60 to 190 bar(abs).In particular, step b) can be carried out in continuous mode, in batch mode or in semi-batch mode.By way of example, the following scheme illustrates reactions according to step b) in case the hydrogenation reaction is carried out with H2 alone, with H2 in the additional presence of a primary amine (here: monomethylamine (MMA)), and with H2 in the additional presence of a secondary amine (here: dimethylamine (DMA))along the following principal reaction mechanisms:Other suitable amines for this reaction include monopropylamine, monoethylamine and monoisopropylamine as wellas the respective secondary diamines. In the above scheme, R is preferably H or alkyl.Preferably, one or more additives are employed for the hydrogenation of the at least one first intermediate (I1) to atleast one polyamine according to b). Preferably, the one or more additives comprise at least one basic additive, wherein the at least one basic additive preferably comprises one or more of at least one basic metal salt and ammonia, more preferably one or more of at least one alkali hydroxide and ammonia, more preferably one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide and ammonia, more preferably one or more of lithium hydroxide and ammonia. The catalyst used for the hydrogenation of the at least one first intermediate (I1) to at least one polyamine according to b) to at least one polyamine compound (II) or (III) is preferably a heterogeneous catalyst, more preferably a heterogeneous catalyst in the form of a suspension or a fixed-bed catalyst. Preferably or optionally, the catalyst is supported on a suitable supporting material which preferably comprises one or more of charcoal, at least one aluminum oxide, at least one silicon oxide, at least one titanium oxide and at least one zirconium oxide.Preferably, the catalyst used for the hydrogenation of the at least one first intermediate (I1) to at least one polyamine according to b) to at least one polyamine compound (II) or (III) with at least one primary amino group, initially in thepresence of no amine or of ammonia, comprises one or more of nickel, cobalt and ruthenium, wherein morepreferably, the catalyst comprises cobalt and optionally consists of cobalt. More preferably the catalyst comprises, optionally consists of cobalt supported on a suitable supporting material as defined above. Preferably, the catalyst used for the hydrogenation of the at least one first intermediate (I1) to at least one polyamine according to b) in the presence of at least one primary and / or at least one secondary amine to at least one polyamine compound (III) with at least one secondary and / or tertiary amino group comprises one or more of copper, palladium, platinum and rhodium, wherein more preferably, the catalyst comprises palladium and optionally consists of palladium.More preferably the catalyst comprises, optionally consists of palladium supported on a suitable supporting material asdefined above. Further, the present invention relates to an intermediate (I1), obtainable or obtained by the above process. Further, the present invention relates to a polyamine compound (II) or (III), obtainable or obtained by the above process. Further, the present invention relates to an intermediate (I1) comprising at least one, preferably terminal, group CN, as defined above, preferably comprising at least two, preferably terminal, groups CN. Further, the present invention relates to a polyamine compound (II) and / or (III), comprising at least one, preferablyterminal, group NH, as defined above, preferably comprising at least two, preferably terminal, groups NH.Further, the present invention relates to the use of a polyamine compound (II) and / or (III) as defined above whichcontains at least one primary or secondary amine group or of a polyamine compound (II) as defined above in or asco-reactant, hardener or curative for epoxy resins.Further, the present invention relates to an epoxy resin composition, containing a polyamine compound (II) and / or(III) as defined above, which contains at least one primary or secondary amine group or containing a polyaminecompound (II) and / or (III) as defined above, preferably as a co-reactant, a hardener or a curative.Further, the present invention relates to an epoxy resin composition, containing a polyamine compound (II) and / or(III) as defined above, which contains at least one primary or secondary amine group or a polyamine compound (II)as defined above, reacted as a co-reactant, a hardener or a curative with an epoxy resin.Further, the present invention relates to the use of a polyamine compound (II) or (III) as defined above, or ofcompounds prepared therewith, for flotation; corrosion inhibition; asphalt emulsification; fertilizer-anticaking agents; additives for preventing caking of powdered minerals; emulsifiers, adjuvants, and intermediates in pesticide production; additives in plastic formulations; pigment-grinding aids; dispersants for pigments in paints, coatings, and magnetic tape; thickening agents in drilling muds, oil-based coatings and the paint industry; biocidal applications in households, swimming pools and oil fields; lubricants; petroleum additives; deicers for motor fuels; catalysis (such as in polyurethane formation); manufacturing of polyurethanes; intermediates for dyes, and of a polyamine compound (II) and / or (III) as defined above comprising tertiary amino groups as or for producing cleavable PU catalysts that can optionally be incorporated due to additional functional groups or upon cleavage. The functionalized cleavable amines which result from the functionalization of cleavable amines described herein exhibit a variety of uses. In general, the functionalized cleavable amines can be applied in any application that is typical for amines, as long as the backbone (ketal, acetal or silylketal functionality) does not have an (negative) influence on the application. Examples, possibly after further functionalization, include: epoxy hardening; flotation; corrosion inhibition; asphalt emulsification; fertilizer-anticaking agents; additives for preventing caking of powdered minerals; emulsifiers, adjuvants, and intermediates in pesticide production; additives in plastic formulations; pigment- grinding aids; dispersants for pigments in paints, coatings, and magnetic tape; thickening agents in drilling muds, oil- based coatings and the paint industry; biocidal applications in households, swimming pools and oil fields; lubricants; petroleum additives; deicers for motor fuels; catalysis (such as in polyurethane formation); manufacturing ofpolyurethanes; intermediates for dyes.It cannot be excluded that a compound which can be obtained by the advantageous process according to the present invention might be already disclosed in the prior art by chance in another context, such as being prepared by another process. Therefore, as a purely precautionary measure, one or more of the following compounds are excluded in the context of the present invention regarding the compounds as such, however not excluded in the context of the process of the present invention:- a polyamine compound (II) and / or (III), wherein X is C, a1, a2, b1, b2, c1, c2, d1, d2 are each 1, so that a1 +b1 + c1 + d1 = 4, and a2 + b2 + c2 + d2 = 4;- a compound of the formula C(-O(-CH2)x-NH-(-CH2)y-NHZ)4 with x = 2, y = 2, Z = H, or with x = 6, y = 2, Z = H,or with x = 2, y = 2, Z being (-CH2)2H;- one or more of the following compounds:- one or more of the following compounds:5 10Biodegradability As mentioned above, cleavable amines can potentially provide a solution to increase the recyclability of epoxy systems or enhance the biodegradability of polyamine-based polymers. The use of cleavable amines as epoxy hardeners enables better recycling of resulting epoxy systems, or as starting materials for polymers to increase the biodegradability.Ideally, the cleavable amines are readily biodegradable, i.e., show equal to or more than 60% oxygen consumptionwithin 28 days in the OECD 301 F test or at least show equal to or more than 60% within 56 days in the OECD 301 Ftest. Alternatively, the cleavable amines are inherently biodegradable in the OECD 302 B test, i.e., show equal to ormore than 70% dissolved organic carbon (DOC) levels. Even an incremental improvement of the biodegradability tomore than 20%, preferably more than 40% and even more preferably to more than 50% oxygen consumption within28 days in the OECD 301 F test would be a technical advantage vs. the current state of the art (no biodegradability at all or less than 10% oxygen consumption within 28 days in the OECD 301 F test). Hence, the present invention addresses the need to find improved cleavable amine architectures with a superior performance profile, a feasible preparation process and an improved biodegradation behavior. Preferably, compounds (II) and (III) demonstrate at least 20%, preferably at least 40% or more preferably at least60% biodegradability according to the OECD 301 A, B, C, D, E or F or OECD 302 B, preferably OECD 301 C orOECD 301 F, standard within 56 days, preferably within 28 days. In preferred embodiments, compounds (II) and (III) of the present invention demonstrate a biodegradation of at least 20%, at least 30%, at least 40%, at least 50%, or at least 60% biodegradability according to the OECD standard 301B, C, D or F within 28 days. The OECD standards 301 B, C, D and F are all respirometry test methods. The skilledperson is well-aware of these tests and therefore solely OECD standard 301 F will be described representatively.For the purposes of this invention, aerobic biodegradation in wastewater according to OECD 301 F is expressed as apercentage of the theoretical oxygen demand (ThOD, which is measured by the elemental analysis of the compound of interest), which is needed to completely biodegrade the compound sample. Thus, the amount of oxygen taken up by the microbial population during biodegradation of the test substance (corrected for uptake by blank inoculum, run in parallel) is expressed as a percentage of ThOD. The obtained values are preferably measured in triplicate usingthe OECD 301 F manometric respirometry method. The consumption of oxygen is determined by measuring thechange in pressure in the apparatus using an OxiTop® C (Xylem 35 Analytics Germany Sales GmbH & Co KG). Details for the tests performed are given in the experimental section below.  The OECD standards OECD 301 A, E and 302 B are Dissolved Organic Carbon (DOC) tests. Also, these tests are well-known for the skilled person. Therefore, solely OECD standard 301 A will be described representatively. Standard OECD 301 A is a DOC Die Away Test: The test substance is used at a high concentration compared to theother tests, i.e.10-40 mg DOC / L (DOC = Dissolved Organic Carbon). The DOC concentration is measured at definedintervals over a period of 28 days. However, the skilled person is also aware of other tests that can be used to determine the biodegradability of the inventive compounds. These tests include chemical, physical and biological tests. For example, the used test may bebased on the specific activity of an indicator enzyme or the amount of expression of an indicator gene. Physical testscan involve physical parameters, such as the density, surface tension or electric conductivity of the solvent of thesample. In such tests, the inventive compounds demonstrate a significant biodegradability, i.e. at least 20 %, at least30 %, at least 40 %, at least 50 %, at least 60 % or at least 70 % of the maximum biodegradation.In preferred embodiments, compounds (II) and (III) of the present invention demonstrate a biodegradation of at least20 %, at least 30 %, at least 40 %, at least 50 %, at least 60 % or at least 70 % biodegradability according to theOECD standard 301 A, E or 302 B within 28 days, and / or demonstrate at least 20 %, preferably at least 40 % ormore preferably at least 60 % biodegradability according to the OECD 301 A, B, C, D, E or F or OECD 302 B,preferably OECD 301 C or OECD 301 F, standard within 56 days, preferably within 28 days. Further aspect According to another aspect, the process of the present invention comprises the step of converting a chemicalmaterial obtainable by or obtained by the process as defined above to obtain a product Ω.Preferably, the product Ω is selected from:- building block or monomer; or- polymer, preferably polymer A, polymer composition, preferably polymer composition A, or polymer product,preferably polymer product A; or- agrochemical composition, agrochemical formulation auxiliary or agrochemically active ingredient; or- active pharmaceutical ingredient or intermediate thereof, pharmaceutical excipient, animal feed additive,human food additive, dietary supplements, aroma chemical or aroma composition; or- aqueous polymer dispersion, preferably polyurethane or polyurethane – poly(meth)acrylate hybrid polymerdispersion, emulsion, binder for paper and fiber coatings, UV-curable acrylic polymer for hot melts and coatings polyisocyanates, hyperbranched polyester polyol, polymeric dispersant for inorganic binder compositions, unsaturated polyester polyol or 100% curable composition; or- cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient or composition orformulation thereof; or- polymer B, polymer composition B, coating composition, other functional composition, foil, molded body,coating or coated substrate.Preferably, the content of the chemical material in the product Ω is 1 weight-% or more, preferably 2 weight-% ormore, more preferably 5 weight-% or more, more preferably 15 weight-% or more, more preferably 30 weight-% or more, more preferably 40 weight-% or more, more preferably 60 weight-% or more, more preferably 80 weight-% or more, more preferably 90 weight-% or more, more preferably 95 weight-% or more; and / orthe content of the chemical material in the product Ω is 100 weight-% or less, preferably 95 weight-% or less, morepreferably 90 weight-% or less, more preferably 50 weight-% or less, more preferably 25 weight-% or less, more preferably 10 weight-% or less; and preferably wherein the content is determined based on identity preservation and / or segregation and / or mass balance and / or book and claim chain of custody models, preferably based on mass balance, preferably the International Sustainability and Carbon Certification (ISCC) standard. The publication Prior Art Disclosure; Issue 684; paragraphs

[1000] to

[8005] ; ISSN: 2198-4786; published: February 12, 2024 will be regarded as Reference RF1, which is incorporated herein by reference in its entirety. Preferably, theproduct Ω is a product as described in Reference RF1; paragraphs

[1000] to

[8005] . Preferably, the processdescribed herein is further a process for the production of a product.The converting step to obtain the product Ω preferably comprises one or more step(s) as described below and can beperformed by conventional methods well known to a person skilled in the art. The converting step preferably comprises one or more step(s) selected from: recycling, preferably depolymerizing, gasifying, pyrolyzing, and / or steam cracking; and / or purifying, preferably crystallizing, (solvent) extracting, distilling, evaporating, hydrotreating, absorbing, adsorbing and / or subjecting to ion exchanger; and / or assembling, preferably foaming, synthesizing, chemical conversion, chemically transforming, polymerizing and / or compounding; and / orforming, preferably foaming, extruding and / or molding; and / or finishing, preferably coating and / or smoothing. In addition, the one or more step(s) are described in detail in Reference RF1; paragraphs

[1000] to

[8005] . The term “building block”, as used in the context of the product Ω herein, comprises compounds, which are in agaseous or liquid state under standard conditions of 0 °C and 0.1 MPa. Building blocks are typically used in chemicalindustry to form secondary products, which provide a higher structural complexity and / or higher molecular weight than the building block on which the secondary product is based. The building block is preferably selected from the group consisting of hydrogen, carbon monoxide, carbon dioxide, ethylene oxide, ethylene glycols, syngas comprising a mixture of hydrogen and carbon monoxide, alkanes, alkenes, alkynes and aromatic compounds. The alkanes, alkenes, alkynes and aromatic compounds comprise in particular 1 to 12 carbon atoms, respectively. The term “monomer”, as used in the context of the product Ω herein, comprises molecules, which can react with each other to form polymer chains by polymerization. The monomer is preferably selected from the group consisting of (meth)acrylic acid, salts of (meth)acrylic acid; in particular sodium, potassium and zinc salts; (meth)acrolein and(meth)acrylates. (Meth)acrylates comprising 1 to 22 carbon atoms are preferred, in particular comprising 1 to 8carbon atoms. The terms (meth)acrylic acid, (meth)acrolein or (meth)acrylate relate to acrylic acid, acrolein or acrylate and also to methacrylic acid, methacrolein or methacrylate, where applicable. Further, the monomer can be selected from hexamethylenediamine (HMD) and adipic acid. The building block can further be an intermediate compound. The term “intermediate compound”, as used in the context of the product Ω herein, comprises organic reagents, which are applied for formation of compounds with higher molecular complexity. The intermediate compound can be selected for example from the group consisting ofphosgene, polyisocyanates and propylene oxide. The polyisocyanates are in particular aromatic di- andpolyisocyanates, preferably toluene diisocyanate (TDI) and / or diphenylmethane diisocyanate (MDI). The building block and the monomer and typical converting step(s) to obtain the building block or monomer are described in more detail in paragraphs

[1000] to

[1012] of Reference RF1. The term “polymer A”, as used in the context of the product Ω herein, comprises thermoplastic, e.g., polyamide or thermoplastic polyurethane, thermoset, e.g., polyurethane, elastomer, e.g., polybutadiene, or a copolymer or a mixture thereof and is defined in more detail in paragraphs

[2001] to

[2007] of Reference RF1. The term “polymer composition A”, as used in the context of the product Ω herein, comprises all compositions comprising a polymer as described above and one or more additive(s), e.g. reinforcement, colorant, modifier and / or flame retardant, and is defined in more detail in paragraph

[2008] of Reference RF1. The term “polymer product A”, as used in the context ofthe product Ω herein, comprises any product comprising the polymer A and / or polymer composition A as describedabove and is defined in more detail in paragraphs

[2009] and

[2010] of Reference RF1. The step(s) to obtain thepolymer, preferably polymer A, polymer composition, preferably polymer composition A or polymer product, preferably polymer product A is / are described in more detail in paragraph

[2011] of Reference RF1. The term “agrochemical composition”, as used in the context of the product Ω herein, typically relates to a composition comprising an agrochemically active ingredient and at least one agrochemical formulation auxiliary. Examples of agrochemical compositions, active ingredients and auxiliaries are described in more detail in ReferenceRF1, paragraph

[4001] . The agrochemical composition may take the form of any customary formulation. Theagrochemical compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The converting step(s) to obtain the agrochemically active ingredients and auxiliaries may be conducted in analogy to the production step(s) of their analogues that are based on petrochemicals or other precursors that are not gained by recycling processes. In addition, conversion to compounds mentioned in sections “Polymer” and “Cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter,further cosmetic ingredient or compositions or formulations thereof” may be performed as described in these sectionsas well as the respective paragraphs in Reference RF1. The term active pharmaceutical ingredients and / or intermediates thereof, as used in the context of the product Ω herein, comprises substances that provide pharmacological activity or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease, or to affect the structure or any function of the body. Intermediatesthereof are isolated products that are generated during a multi-step route of synthesis of an active pharmaceuticalingredient. The term pharmaceutical excipients, as used in the context of the product Ω herein, comprises compounds or compound mixtures used in compositions for various pharmaceutical applications, which are not substantially pharmaceutically active on itself. Active pharmaceutical ingredients and / or intermediates thereof and pharmaceutical excipients are defined in more detail in paragraph

[5001] of Reference RF1. The converting step(s) to obtain the active pharmaceutical ingredients and / or intermediates thereof and pharmaceutical excipients may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art. The terms animal feed additives, human food additives, dietary supplements, as used in the context of the product Ω herein, comprises Vitamins, Pro-Vitamins and active metabolites thereof including intermediates and precursors, especially Vitamin A, B, E, D, K and esters thereof, like acetate, propionate, palmitate esters or alcohols thereof like retinol or salts thereof and any combinations thereof; Tetraterpenes, especially isoprenoids like carotenoids and xanthophylls including their intermediates and precursors as well as mixtures and derivates thereof, especially beta carotene, Canthaxanthin, Citranaxanthin, Astaxanthin, Zeaxanthin, Lutein, Lycopene, Apo-carotenoids, and any combinations thereof; organic acids, especially formic acid, propionic acid and salts thereof, such as sodium, calcium or ammonium salts, and any combinations thereof, such as but not limited to mixtures of formic acid and sodium formiate, propionic acid and ammonium propionate, formic acid and propionic acid, formic acid and sodium formiateand propionic acid, propionic acid and sodium propionate and formic acid and sodium formiate; glycerides of carboxylic acids and short and medium chain fatty acids, conjugated linoleic acids, such as omega-6 fatty acid (C18:2) methyl ester and 1,2-propandiol and beverage stabilizers, such as polyvinylpyrrolidone-polymer or polyvinylimidazole / polyvinylpyrrolidone-copolymer. Animal feed additives, human food additives and dietary supplements are defined in more detail in paragraph

[5002] of Reference RF1. The converting step(s) to obtain the animal feed additives, human food additives, dietary supplements may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art. The terms aroma chemical and aroma composition as used in the context of the product Ω herein, comprise a volatile organic substance with a molecular weight between 70-250 g / mol comprising a functional group with a carbon skeleton of C5-C16carbon atoms comprising linear, branched, cyclic, for example with a ring size of C5-C18, bicyclic or tricyclic aliphatic chains and but not necessarily one or more unsaturated structural elements like double bonds, triplebonds, aromatics or heteroaromatics and preferably the one or more additional functional groups are selected fromalcohol, ether, ester, ketone, aldehyde, acetal, carboxylic acid, nitrile, thiol, amine. In one aspect, the aroma chemical is a terpene-based aroma chemical, for example selected from monoterpenes and monoterpenoids, sesquiterpenes and sesquiterpenoids, diterpenes, triterpenes or tetraterpenes. Aroma chemicals can be combined with further aroma chemicals to give an aroma composition. Aroma chemicals and aroma compositions are defined in more detail in paragraph

[5003] of Reference RF1. The converting step(s) to obtain the aroma chemical and aroma composition may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art. The term “aqueous polymer dispersion”, as used in the context of the product Ω herein, comprises aqueous composition(s) comprising dispersed polymer(s) and is defined in more detail in the section

[6001] entitled “aqueous polymer dispersion” of Reference RF1. The dispersed polymer(s) may be selected from acrylic emulsion polymer(s), styrene acrylic emulsion polymer(s), styrene butadiene dispersion(s), aqueous dispersion(s) comprising compositeparticles, acrylate alkyd hybrid dispersion(s), polyurethane(s) (including UV-curable polyurethanes) and polyurethane- poly(meth)acrylate hybrid polymer(s). The term “emulsion polymer”, as used in the context of the product Ω herein,comprises polymer(s) made by free-radical emulsion polymerization. Aqueous polyurethane dispersion(s) are definedin more detail in the section

[6002] entitled “Polyurethane dispersions” of Reference RF1. UV-curablepolyurethane(s) is / are defined in more detail in the section

[6017] of Reference RF1. Polyurethane -poly(meth)acrylate hybrid polymer(s) is / are defined in more detail in the section

[6016] of Reference RF1. The term “polymeric dispersant”, as used in the context of the product Ω herein, comprises preferably polymer(s) comprising polyether side chain, in particular polycarboxylate ether polymer(s) and polycondensation product(s) defined in more detail in paragraph

[6020] entitled “Polymeric dispersant” of Reference RF1. The converting (polymerization) step(s) to obtain the aqueous polymer dispersion(s) comprising emulsion polymer(s) is / are defined in more detail in the section

[6003] entitled “Emulsion polymerization” of Reference RF1.The converting (polymerization) step(s) to obtain the aqueous polyurethane dispersion(s) is / are defined in moredetail in the section

[6014] entitled “Process for the preparation of aqueous polyurethane dispersions” and section[6017)] entitled “Aqueous UV-curable polyurethane dispersions, their preparation and use and compositions containing them” of Reference RF1.Composition(s) and uses of aqueous polymer dispersion(s) and of polymeric dispersant(s) are defined in more detailin the following sections of Reference RF1:section

[6004] entitled “Uses of aqueous polymer dispersions”,section

[6005] entitled “Binders for architectural and construction coatings”section

[6006] entitled “Binders for paper coating”section

[6007] entitled “Binders for fiber bonding” section

[6008] entitled “Adhesive polymers and adhesive compositions” section

[6015] entitled “Aqueous polyurethane dispersions suitable for use in coating compositions”section

[6016] entitled “Aqueous polyurethane - poly(meth)acrylate hybride polymer dispersions suitable for use incoating compositions” section

[6017] entitled “Aqueous UV-curable polyurethane dispersions, their preparation and use and compositions containing them” section

[6018] entitled “Inorganic binder compositions comprising polymeric dispersants and their use”

[6019] 100% curable coating compositions UV-crosslinkable poly(meth)acrylate(s) and its / their uses are defined in more detail in section

[6009] entitled “UV- crosslinkable poly(meth)acrylates for use in UV-curable solvent-free hotmelt adhesives and their use for making pressure-sensitive self-adhesive articles” of Reference RF1. Polyisocyanate(s), composition(s) comprising them and their uses are defined in more detail in section

[6010] entitled “Polyisocyanates” of Reference RF1. Hyperbranched polyester polyol(s) and its / their uses are defined in more detail in section

[6011] entitled “Organicsolvent based hyperbranched polyester polyols suitable for use in coating compositions” of Reference RF1. Theconverting step(s) to obtain the hyperbranched polyester polyols is / are defined in more detail in the section

[6012] entitled “Preparation of organic solvent based hyperbranched polyester polyols” of Reference RF1. Coating composition(s) comprising hyperbranched polyester polyol(s), polyisocyanate(s) and additive(s) and substrate(s)coated therewith are defined in more detail in section

[6013] entitled “Organic solvent based two component coatingcompositions comprising hyperbranched polyester polyols and polyisocyanates” of Reference RF1. Unsaturated polyester polyol(s), solvent-based coating composition(s) comprising said unsaturated polyester polyol(s) and substrate(s) for coating with said coating composition(s) are defined in more detail in section

[6018] entitled “Organic solvent based coating composition comprising unsaturated polyester polyols” of Reference RF1.100% curable coating composition(s) is / are defined in more detail in section

[6019] of Reference RF1. Polymeric dispersant(s) for inorganic binder compositions is / are defined in more detail in section

[6020] of Reference RF1. The inorganic binder composition(s) comprising the polymeric dispersants and their use are defined in more detail in section

[6021] of Reference RF1. The converting step(s) to obtain the polymeric dispersant(s) are defined in more detail in section

[6020] of Reference RF1. The term “inorganic binder composition” comprising the polymeric dispersant(s), as used in the context of the product Ω herein, comprises preferably in particular hydraulically setting compositions and compositions comprising calcium sulfate and is defined in more detail in section

[6021] ofReference RF1 entitled “Inorganic binder compositions comprising the polymeric dispersant and their use”. Specificbuilding material formulation(s) comprising polymeric dispersant(s) or building product(s) produced by a building material formulation comprising a polymeric dispersant are disclosed in more detail in section

[6021] of Reference RF1. The term “cosmetic surfactant”, as used in the context of the product Ω herein, comprises non-ionic, anionic, cationic and amphoteric surfactants and is defined in more detail in paragraph

[7002] of Reference RF1. The term “emollient”, as used in the context of the product Ω herein, refers to a chemical compound used for protecting, moisturizing, and / or lubricating the skin and is defined in more detail in paragraph

[7003] of Reference RF1. The term “wax”, as used in the context of the product Ω herein, comprises pearlizers and opacifiers and is defined in more detail in paragraph

[7004] of Reference RF1. The term “cosmetic polymer”, as used in the context of the product Ω herein, comprises any polymer that can be used as an ingredient in a cosmetic formulation and is defined in more detail inparagraph

[7005] of Reference RF1. The term “UV filter”, as used in the context of the product Ω herein, refers to achemical compound that blocks or absorbs ultraviolet light and is defined in more detail in paragraph

[7006] of Reference RF1. The term “further cosmetic ingredient”, as used in the context of the product Ω herein, comprises any ingredient suitable for making a cosmetic formulation. Several sources disclose cosmetically acceptable ingredients. E. g. the database Cosing on the internet pages of the European Commission discloses cosmetic ingredients and the International Cosmetic Ingredient Dictionary and Handbook, edited by the Personal Care Products Council (PCPC), discloses cosmetic ingredients. The term “composition and / or formulation thereof” with reference to the cosmeticsurfactant, emollient, wax, cosmetic polymer, UV filter and / or further cosmetic ingredient refers to personal careand / or cosmetic compositions or formulations defined in more detail in paragraph

[7007] of Reference RF1. The converting step(s) to obtain the cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter or further cosmeticingredient is / are defined in more detail in paragraph

[7008] of Reference RF1.The terms “polymer B”, “polymer composition B”, “coating composition”, “other functional composition”, “foil”, “molded body”, “coating” and “coated substrate” are well known to the person skilled in the art and are defined in more detail from paragraph

[8000] to

[8005] of Reference RF1.Embodiments The present invention is further illustrated by the following set of embodiments and combinations of embodiments resulting from the dependencies and back-references as indicated. In particular, it is noted that in each instancewhere a range of embodiments is mentioned, for example in the context of a term such as "The process of any oneof embodiments 1 to 4", every embodiment in this range is meant to be explicitly disclosed for the skilled person, i.e. the wording of this term is to be understood by the skilled person as being synonymous to "The process of any one of embodiments 1, 2, 3 and 4". Further, it is explicitly noted that the following set of embodiments represents a suitably structured part of the general description directed to preferred aspects of the present invention, and, thus, suitably supports, but does not represent the claims of the present invention. 1. A process for preparing polyamines via (meth)acrylonitrile and / or crotononitrile addition to an amine followed by hydrogenation in the presence of a catalyst and hydrogen and optionally in the additional presence of ammonia, primary and / or secondary amine, comprisinga) reacting at least one amine of general formula (I)with (meth)acrylonitrile and / or crotononitrile, wherein the amine of general formula (I) comprises at least one, preferably terminal, group NH which is reacted with the (meth)acrylonitrile and / or crotononitrile, thereby obtaining at least one first intermediate (I1), wherein at least one, preferably terminal, group NH of the amine of general formula (I) is converted to a group N-CH2-CHR-CN or to a group N-CHR-CH2-CN with R being H or methyl, preferably to a group N-CH2-CH2-CN; b) hydrogenating the at least one first intermediate (I1) to at least one polyamine compound (II),comprising converting the at least one group N-CH2-CHR-CN or group N-CHR-CH2-CN, preferably the at least one group N-CH2-CH2-CN, to at least one group N-CH2-CHR-CH2-NH2 or group N-CHR-CH2- CH2-NH2, preferably to at least one group N-CH2-CH2-CH2-NH2; or hydrogenating the at least one first intermediate (I1) in the additional presence of ammonia, primary and / or secondary amine HNR’R” with R’ being H, C1-C3-alkyl, preferably H, methyl or ethyl, R” beingH, C1-C3-alkyl, preferably H, methyl or ethyl, to at least one polyamine compound (III), comprising converting the at least one group N-CH2-CHR-CN or group N-CHR-CH2-CN, preferably the at least one group N-CH2-CH2-CN, to at least one group N-CH2-CHR-CH2-NR’R” or group N-CHR-CH2-CH2-NR’R”, preferably to at least one group N-CH2-CH2-CH2-NR’R” wherein X is C or Si or HC-CH; wherein a1, a2, b1, b2, c1, c2, d1, d2 are independently of each other 0 or 1, with a1 + b1 + c1 + d1 ≥ 2 and a2 + b2 + c2 + d2 ≥ 2;wherein, if a1 = a2 = 0, YA1 is H or optionally substituted C1-C12-alkyl;wherein, if a1 = 1 and a2 = 0, YA1is optionally substituted C1-C12-alkyl; wherein, if a1 = a2 = 1, or if a1 = 0 and a2 = 1, YA1is optionally substituted C1-C12-alkylene; wherein, if b1 = b2 = 0, YB1is H or optionally substituted C1-C12-alkyl; wherein, if b1 = 1 and b2 = 0, YB1is optionally substituted C1-C12-alkyl; wherein, if b1 = b2 = 1, or if b1 = 0 and b2 = 1, YB1is optionally substituted C1-C12-alkylene; wherein, if c1 = c2 = 0, YC1is H or optionally substituted C1-C12-alkyl; wherein, if c1 = 1 and c2 = 0, YC1is optionally substituted C1-C12-alkyl; wherein, if c1 = c2 = 1, or if c1 = 0 and c2 = 1, YC1is optionally substituted C1-C12-alkylene; wherein, if d1 = d2 = 0, YD1is H or optionally substituted C1-C12-alkyl; wherein, if d1 = 1 and d2 = 0, YD1is optionally substituted C1-C12-alkyl; wherein, if d1 = d2 = 1, or if d1 = 0 and d2 = 1, YD1is optionally substituted C1-C12-alkylene;wherein RA2, RA3, RB2, RB3, RC2, RC3, RD2, RD3 are, independently of each other, H or optionally substituted C1-C12-alkyl, with at least one of RA2, RA3, RB2, RB3, RC2, RC3, RD2, and RD3being H; wherein, if X is C or Si- YA1 and YB1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when a1 = b1= 1; and / or- YC1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when c1 = d1= 1; wherein, if X is HC-CH and (O)a1(O)b1X(O)c1(O)d1isthen- YA1 and YC1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when a1 = c1= 1; and / or- YB1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when b1 = d1= 1; or -YA1 and YB1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when a1 = b1= 1; and / or -YC1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably when c1 = d1= 1.2. The process of embodiment 1, wherein the (meth)acrylonitrile is acrylonitrile, methacrylonitrile or a mixturethereof.3. The process of embodiment 1 or 2, wherein the amine of general formula (I) comprises at least two, preferablyterminal, groups NH which are reacted with the (meth)acrylonitrile and / or crotononitrile.4. The process according to any one of embodiments 1 to 3, wherein, if a1 = 1, then a2 = 1; if b1 = 1, then b2 =1; if c1 = 1, then c2 = 1; and if d1 = 1, then d2 = 1.5. The process of any one of embodiments 1 to 4, wherein RA2, RB2, RC2 and RD2 are H, methyl, ethyl, propyl orisopropyl, preferably H, and RA3, RB3, RC3, RD3are H, or wherein RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, preferably H, and RA3, RB3, RC3, RD3 are methyl, or wherein RA2, RB2, RC2 and RD2 are H,methyl, ethyl, propyl or isopropyl, preferably H, and RA3, RB3, RC3, RD3are ethyl, or wherein RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, preferably H, and RA3, RB3, RC3, RD3are propyl, or wherein RA2, RB2, RC2and RD2are H, methyl, ethyl, propyl or isopropyl, preferably H, and RA3, RB3, RC3, RD3are isopropyl, or wherein RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are methyl, or wherein RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are ethyl, or wherein RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are propyl, or wherein RA2, RB2, RC2and RD2are H and RA3, RB3, RC3, RD3are isopropyl.6. The process of any one of embodiments 1 to 5, wherein all alkyl groups and alkylene groups present in the atleast one amine of general formula (I) are non-branched groups.7. The process of any one of embodiments 1 to 6, wherein all alkyl groups and alkylene groups present in the atleast one amine of general formula (I) are C1-C6-groups, preferably C1-C4-groups. 8. The process of any one of embodiments 1 to 7, wherein, if X is C, two, one or none of YA1, YB1, YC1and YD1are H, preferably wherein one or none of YA1, YB1, YC1and YD1is H, more preferably wherein none of YA1, YB1, YC1and YD1is H, with the corresponding a1, b1, c1, d1 being 0 so that no hydroxyl group is covalently linked with X.9. The process of any one of embodiments 1 to 7, wherein, if X is Si or HC-CH, none of YA1, YB1, YC1 and YD1 isH. 10. The process of any one of embodiments 1 to 8, wherein X is C and a1 + b1 + c1 + d1 = 2.11. The process of any one of embodiments 1 to 7 or 9, wherein X is Si and a1 + b1 + c1 + d1 ≥ 2.12. The process of any one of embodiments 1 to 7 or 9, wherein X is HC-CH anda1 + b1 + c1 + d1 = 2 or a1 + b1 + c1 + d1 = 4.13. The process of any one of embodiments 1 to 7, 9 or 12, wherein X is HC-CH and a1 + b1 + c1 + d1 = 2,wherein a1 = c1 = 1 or b1 = d1 = 1. 14. The process of any one of embodiments 1 to 7, 9 or 12, wherein X is HC-CH and a1 = b1 = c1 = d1 = 1.15. The process of any one of embodiments 1 to 14, wherein reacting at least one amine of general formula (I)according to a) is carried out in the presence of at least one polar protic solvent, preferably comprising one or more of water and methanol, more preferably comprising methanol, more preferably being methanol.16. The process of embodiment 15, wherein the molar ratio of the at least one polar protic solvent to the at leastone amine of general formula (I) is in the range of from 0.05 to 5, preferably in the range of from 0.5 to 4,more preferably in the range of from 1.5 to 3.0, more preferably in the range of from 2.5 to 3.0.17. The process of embodiment 15, wherein the molar ratio of the at least one polar protic solvent to the at leastone amine of general formula (I) is in the range of from 0.05 to 5, preferably in the range of from 0.1 to 2.0,more preferably in the range of from 0.15 to 1.0, more preferably in the range of from 0.2 to 0.5, more preferably in the range of from 0.25 to 0.35.18. The process of any one of embodiments 15 to 17, wherein the at least one polar protic solvent is present in anamount effective to increase the linear selectivity of the (meth)acrylonitrile and / or crotononitrile addition to the at least one amine of general formula (I). 19. The process of any one of embodiments 1 to 18, wherein the at least one amine of general formula (I), the intermediate (I1), the polyamine compound (II) and the polyamine compound (III) do not contain halogen andsulfur atoms, do not contain aromatic groups and at most two heterocyclic groups.20. The process of embodiment 19, wherein the at least one amine of general formula (I), the intermediate (I1),the polyamine compound (II) and the polyamine compound (III) are formed solely of C, H, O, N, and optionallyadditionally one or two, preferably one, Si atoms.The process of any one of embodiments 1 to 20, preferably embodiment 19 or 20, wherein when X is C, the atleast one amine of general formula (I), the intermediate (I1), the polyamine compound (II) and the polyaminecompound (III) have a molecular weight of at most 480 g / mol, preferably of at most 460 g / mol, morepreferably of at most 440 g / mol.The process of any one of embodiments 1 to 21, wherein reacting at least one amine of general formula (I)according to a) is carried out at a temperature in the range of from 10 to 150 °C, preferably in the range of from 20 to 100 °C, more preferably in the range of from 30 to 80 °C. The process of any one of embodiments 1 to 22, wherein reacting at least one amine of general formula (I) according to a) is carried out at a pressure in the range of from 0.8 to 1.2 bar(abs), preferably in the range offrom 0.9 to 1.1 bar(abs), more preferably at ambient pressure of 1.0 bar(abs).The process of any one of embodiments 1 to 23, wherein for reacting at least one amine of general formula (I)according to a), the at least one amine of general formula (I) and the (meth)acrylonitrile and / or crotononitrile are employed at a molar ratio of the (meth)acrylonitrile and / or crotononitrile relative to the reactive amino groups of the at least one amine of general formula (I) in the range of from 0.80 to 1.25, preferably in the range of from 0.90 to 1.15, more preferably in the range of from 1.00 to 1.05.The process of any one of embodiments 1 to 24, wherein hydrogenating the at least one first intermediate (I1)to at least one polyamine according to b) exhibits one or more of the following features:- it is carried out at a temperature in the range of from 20 to 200 °C, preferably in the range of from 40 to160 °C, more preferably in the range of from 50 to 140 °C;- it is carried out at a pressure in the range of from 1 to 325 bar(abs), preferably in the range of from 10to 200 bar(abs), more preferably in the range of from 60 to 190 bar(abs);- it is carried out at a molar ratio of ammonia, primary and / or secondary amine HNR‘R‘‘ to cyano groupsin the intermediate (I1) in the range of from 0.1 to 40, preferably in the range of from 0.5 to 20, more preferably in the range of from 1.0 to 10.The process of any one of embodiments 1 to 25, wherein one or more additives are employed for thehydrogenation of the at least one first intermediate (I1) to at least one polyamine according to b), the one or more additives preferably comprising at least one basic additive, wherein the at least one basic additive preferably comprises one or more of at least one basic metal salt and ammonia, more preferably one or more of at least one alkali hydroxide and ammonia, more preferably one or more of lithium hydroxide, sodiumhydroxide, potassium hydroxide and ammonia, more preferably one or more of lithium hydroxide and ammonia.27. The process of any one of embodiments 1 to 26, wherein the catalyst used for the hydrogenation of the atleast one first intermediate (I1) to at least one polyamine according to b) is a heterogeneous catalyst, preferably a heterogeneous catalyst in the form of a suspension or a fixed-bed catalyst, wherein, preferably or optionally, the catalyst is supported on a suitable supporting material which preferably comprises one or more of charcoal, at least one aluminum oxide, at least one silicon oxide, at least one titanium oxide and at least one zirconium oxide, and wherein -the catalyst used for the hydrogenation of the at least one first intermediate (I1) according to b) to atleast one polyamine compound with at least one primary amino group, initially in the presence of no amine or of ammonia, preferably comprises one or more of nickel, cobalt and ruthenium, wherein more preferably, the catalyst comprises cobalt and optionally consists of cobalt, wherein more preferably, the catalyst comprises, optionally consists of cobalt supported on a suitable supporting material as defined above; -the catalyst used for the hydrogenation of the at least one first intermediate (I1) according to b) in thepresence of at least one primary and / or at least one secondary amine to at least one polyaminecompound with at least one secondary and / or tertiary amino group preferably comprises one or more of copper, palladium, platinum and rhodium, wherein more preferably, the catalyst comprises palladium and optionally consists of palladium, wherein more preferably, the catalyst comprises, optionally consists of palladium supported on a suitable supporting material as defined above. 28. An intermediate (I1), obtainable or obtained by the process according to any one of embodiments 1 to 27.29. A polyamine compound (II) or (III), obtainable or obtained by the process according to any one ofembodiments 1 to 27, that preferably demonstrates at least 20%, preferably at least 40% or more preferably at least 60% biodegradability according to the OECD 301 A, B, C, D, E or F or OECD 302 B, preferably OECD 301 C or OECD 301 F, standard within 56 days, preferably within 28 days.30. An intermediate (I1) comprising at least one, preferably terminal, group CN, as defined in any one ofembodiments 1 to 14 and 19 to 21.31. The intermediate (I1) of embodiment 30, comprising at least two, preferably terminal, groups CN.32. A polyamine compound (II) or (III) comprising at least one, preferably terminal, group NH, as defined in any one of embodiments 1 to 14 and 19 to 21.The polyamine compound (II) or (III) of embodiment 32, comprising at least two, preferably terminal, groupsNH.Use of a polyamine compound (II) or (III) according to any one of embodiments 29, 32 and 33 which containsat least one primary or secondary amine group or of a polyamine compound (II) or (III) according to any one ofembodiments 29, 32 and 33 in or as co-reactant, hardener or curative for epoxy resins.An epoxy resin composition, containing a polyamine compound (II) or (III) according to any one ofembodiments 29, 32 and 33, which contains at least one primary or secondary amine group or containing apolyamine compound (II) or (III) according to any one of embodiments 29, 32 and 33, preferably as a co-reactant, a hardener or a curative.An epoxy resin composition, containing a polyamine compound (II) or (III) according to any one ofembodiments 29, 32 and 33, which contains at least one primary or secondary amine group or a polyaminecompound (II) or (III) according to any one of embodiments 29, 32 and 33, reacted as a co-reactant, ahardener or a curative with an epoxy resin.Use of a polyamine compound (II) or (III) according to any one of embodiments 29, 32 and 33, or ofcompounds prepared therewith, for flotation; corrosion inhibition; asphalt emulsification; fertilizer-anticaking agents; additives for preventing caking of powdered minerals; emulsifiers, adjuvants, and intermediates inpesticide production; additives in plastic formulations; pigment-grinding aids; dispersants for pigments inpaints, coatings, and magnetic tape; thickening agents in drilling muds, oil-based coatings and the paint industry; biocidal applications in households, swimming pools and oil fields; lubricants; petroleum additives; deicers for motor fuels; catalysis (such as in polyurethane formation); manufacturing of polyurethanes;intermediates for dyes, and of a polyamine compound (II) or (III) according to any one of embodiments 29, 32and 33 which contains tertiary amino groups as or for producing cleavable PU catalysts which are optionallyincorporated due to additional functional groups or upon cleavage.A process, preferably according to any one of embodiments 1 to 27, comprising the step of converting achemical material obtainable by or obtained by the process according to any one of embodiments 1 to 27 toobtain a product Ω.The process of embodiment 38, wherein the product Ω is selected from:- building block or monomer; or- polymer, preferably polymer A, polymer composition, preferably polymer composition A, or polymerproduct, preferably polymer product A; or- agrochemical composition, agrochemical formulation auxiliary or agrochemically active ingredient; or- active pharmaceutical ingredient or intermediate thereof, pharmaceutical excipient, animal feedadditive, human food additive, dietary supplements, aroma chemical or aroma composition; or -aqueous polymer dispersion, preferably polyurethane or polyurethane – poly(meth)acrylate hybridpolymer dispersion, emulsion, binder for paper and fiber coatings, UV-curable acrylic polymer for hot melts and coatings polyisocyanates, hyperbranched polyester polyol, polymeric dispersant for inorganic binder compositions, unsaturated polyester polyol or 100% curable composition; or -cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient orcomposition or formulation thereof; or -polymer B, polymer composition B, coating composition, other functional composition, foil, moldedbody, coating or coated substrate.40. The process of embodiment 38 or 39,wherein the content of the chemical material in the product Ω is 1 weight-% or more, preferably 2 weight-% ormore, more preferably 5 weight-% or more, more preferably 15 weight-% or more, more preferably 30 weight- % or more, more preferably 40 weight-% or more, more preferably 60 weight-% or more, more preferably 80 weight-% or more, more preferably 90 weight-% or more, more preferably 95 weight-% or more; and / or wherein the content of the chemical material in the product Ω is 100 weight-% or less, preferably 95 weight-%or less, more preferably 90 weight-% or less, more preferably 50 weight-% or less, more preferably 25 weight- % or less, more preferably 10 weight-% or less; and preferably wherein the content is determined based on identity preservation and / or segregation and / or mass balance and / or book and claim chain of custody models, preferably based on mass balance, preferably the International Sustainability and Carbon Certification (ISCC) standard. The invention is further illustrated by the following examples. General synthesis procedure The following section describes a general method for the synthesis of functionalized cleavable amines (II) and (III) using acrylonitrile as vinyl nitrile. The technology used in this patent application describes the addition of acrylonitrileto a di- or higher polyamine, followed by hydrogenation of the cyano groups to yield the corresponding propylamine-extended di- or higher polyamine (functionalized cleavable amine). The addition of polar protic solvents, such aswater, MeOH, EtOH, or iPrOH can increase linear selectivity, meaning it discriminates against the double addition of ACN to the same nitrogen atom of a primary amino group. This linear selectivity is desirable for certain applications. The method with the addition of a solvent represents one variation of the process. In another variation of the process, the solvent is used in small quantities (as an additive) to enhance linear selectivity while maximizing the space-time yield. This allows for a high linear selectivity to be achieved while maintaining a high overall efficiency.Starting from a cleavable amine and a vinyl nitrile compound like acrylonitrile (ACN), a single or multiple Michael addition reaction is used to synthesize a single or multiple cyanoethylated product as the desired intermediate for hydrogenation. This intermediate is then subjected to catalytic hydrogenation to yield the functionalized cleavable amine. In the first reaction stage, ACN is added to the cleavable amine. As side components, mainly ACN adducts with toolow or too high stoichiometry in relation to ACN or incorrect regioisomers due to the double addition of two ACNequivalents to the same nitrogen atom of a primary amino group are obtained. The product and side component spectrum strongly depends on the molecular ratio between N-H functionality in the cleavable amine and ACN. For example, a cleavable diamine with two primary amino groups has four NH functionalities. The desired intermediate exhibits one cyanoethylation per primary amino group. Side products would include the mono-adduct, the tri-adduct, as well as the N,N-adduct as a regioisomer to the desired N,N'-adduct. The selectivity between linear (N,N'-adduct) and branched (N,N-adduct) can be controlled by the addition of polar protic solvents such as water or methanol. Increasing amounts of added solvent correlate with increased linearity. However, at high concentrations of MeOH, the increase in selectivity gradually decreases. For the mentioned diamine with two primary amino groups, the use of2.05 equivalents of ACN and 28 mol% MeOH based on the amount of cleavable diamine yields optimum results,taking into account factors such as space-time yield and distillation and raw material costs.The synthesis of the cyanoethylated product is carried out either continuously, in semi-batch mode or in a batchmode. Initially, the semi-batch synthesis was pursued, and only this variation will be described below.In the semi-batch synthesis, the cleavable amine is introduced into an addition reactor and optionally a solvent oradditive, preferably methanol, is added under stirring. The cleavable amine or mixture is heated to the reactiontemperature, and then ACN is added dropwise with stirring. The dosing rate should be chosen in a way that preventsACN accumulation and allows the desired reaction temperature to be maintained. Therefore, the dosing ratedepends on the reaction kinetics and the cooling capacity of the reactor. Ensuring the initiation of the reaction (e.g., through reaction control) is crucial. The reaction is preferably carried out at temperatures in the range of from 30 to 80 °C. Lower temperatures hinder heat dissipation due to lower temperature gradients between the reaction andcooling medium, while higher temperatures are often not possible due to the safety limitations. After the ACN dosingis completed, the reaction mixture is further stirred at the reaction temperature for a defined period to ensure complete conversion of ACN (preferred residual ACN concentration: less than 0.1 GC area%). Optionally, a solvent can be added after the synthesis to prevent a potential crystallization of the cyanoethylated product mixture. Optionally, the reaction mixture can be cooled to a desired temperature below the reaction temperature, either before or after adding the solvent. The resulting reaction mixture, regardless of whether a solvent was added before or after the reaction, is referred to as the reaction mixture. The reaction mixture is used without further workup for future hydrogenation.In the second reaction stage (b), the reaction mixture is converted into the functionalized cleavable amine raw product through catalytic hydrogenation in the presence of a catalyst and hydrogen. The hydrogenation can be carried out continuously or in a (semi) batch mode. Initially, the semi-batch synthesis was pursued, and only this variation will be described below. The following describes the suspension catalysis using a suspension catalyst, preferably Grace 2724, with high linear selectivity. The hydrogenation is preferably conducted in the presence of ammonia, which reduces the formation of oligomers. The observed side components depend on the obtained ACN adducts, the cleavable amines used, and the number of N-H functionalities in the cleavable amine. In the case of the preferred catalyst Grace 2724 for suspension catalysis, it is a cobalt suspension catalyst from W. R. Grace & Co. The composition of this catalyst is as follows: Al: 2-6 wt.%, Co: ≥ 86 wt.%, Fe: 0-1 wt.%, Ni: 1-4 wt.%, Cr: 1.5-3.5 wt.%. The average particle size ranges from 25 to 55 µm. For Grace 2724, the catalyst is first washed several times with a solvent, preferably MeOH, to remove water from the system (as the catalyst is stored as aqueous paste). The catalyst is then suspended in a solvent, preferably MeOH (preferably, the catalyst is suspended in methanol, with the amount of initial methanol being 20 wt.% of the organic material present in the reactor later; the amount of reaction mixture dosed in the first attempt corresponds to the remaining 80 wt.%). Hydrogen and ammonia (preferably 10 wt.% NH3based on the total amount of organic material in the reactor) are added, and the reaction pressure and temperature are adjusted. The reaction mixture is then added over a defined period under stirring. The dosing rate is adjusted to prevent the accumulation of nitrile species in the reactor and to avoid catalyst deactivation. Additionally, the dosing rate should allow for the dissipation ofreaction heat. Ensuring the initiation of the reaction (e.g., through reaction control) is crucial. The reaction ispreferably carried out at a temperature in the range of from 50 to 140 °C and a reactor pressure in the range of from 60 to 190 bar(abs). Lower temperatures slow down the reaction, while higher temperatures lead to decomposition and scrambling reactions, which also reduce the catalyst's lifetime. Lower pressures reduce the hydrogenation rate, resulting in slower dosing rates. High reaction pressures are preferred. After the reaction mixture is fully dosed, the reaction mixture obtained in this reaction (reaction mixture 2) is further stirred at the reaction temperature and pressure for a defined time to ensure complete conversion of nitrile species (preferred residual nitrile species concentration: less than 0.1 GC area%). After the reaction is completed, the system is cooled and depressurized. The resulting mixture is collected while the catalyst is retained in the reactor. Preferably, 80 wt.% of the reaction mixture 2 is removed from the reactor, leaving 20 wt.% of the reaction mixture 2 in the reactor to suspend the catalyst for the next hydrogenation cycle. The details of filtration depend on the specific reactor type and available peripherals and need to be evaluated on a case-by-case basis if necessary. Preferably, after filtration, the used ammonia is distilled and recovered. The resulting mixture is referred to as the raw product. The distillation of the raw product can be carried out continuously or in a (semi)batch mode. Initially, the batch distillation was pursued, and only this variation will be described below.The collected and homogenized raw product is introduced into the bottom of the distillation column. The distillation is conducted under reduced pressure, with a minimal pressure, preferably less than 20 mbar sump pressure, being preferred to reduce thermal stress on the distillation sump and to provide a greater margin to the onset of decomposition reactions. By increasing the temperature at isobaric conditions, the light components (solvents, light-boiling components) are gradually removed. Subsequently, the product is distilled and collected. Due to similar vaporpressure curves, it is difficult to achieve a distillation separation between the regioisomers with common separation stages. Thus, the purified product contains a low percentage of N,N-functionalized cleavable amines. The ratio between the regioisomers can be significantly influenced by adjusting the selectivity in the addition stage. After the desired amount of valuable product is obtained, the vapor supply is closed, and the vacuum is broken. Depending on the safety concept of the distillation, either multiple batches of raw material can be filled into the column and distilledbefore the sump is removed, or the sump has to be removed after each distillation. The light-boiling and heavy-boiling components are sent for incineration. The obtained purified product is stored until further use. Theconcentration of the obtained functionalized cleavable amine in the purified product is preferably greater than 98.5 GC area%. The products of hydrogenation, functionalized cleavable amines with acetal, ketal, or silyl ketal functionality in the backbone, are partially thermolabile. If these raw products cannot be distilled without significant decomposition, they can be used in further applications without further workup. This is also possible if high purity is not required for furtheruse or if the side components do not impair or even enhance the final product performance. For example, a rawproduct composition containing at least 50 wt.%, preferably at least 60 wt.%, more preferably at least 70 wt.% compound (II) or (III) can be employed. Examples Abbreviations: KDA 2,2'-(propane-2,2-diylbis(oxy))bis(ethan-1-amine) according to formula below MPA-KDA N1-(2-((2-(2-aminoethoxy)propan-2-yl)oxy)ethyl)propane-1,3-diamine according to formula below BPA-KDA N1,N1'-((propane-2,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(propane-1,3-diamine) according to formula below MCE-KDA 3-((2-((2-(2-aminoethoxy)propan-2-yl)oxy)ethyl)amino)propanenitrile according to formula below BCE-KDA 8,8-dimethyl-7,9-dioxa-4,12-diazapentadecanedinitrile according to formula belowN,N-BCE-KDA 3,3'-((2-((2-(2-aminoethoxy)propan-2-yl)oxy)ethyl)azanediyl)dipropanenitrileaccording to formula belowTCE-KDA 4-(2-cyanoethyl)-8,8-dimethyl-7,9-dioxa-4,12-diazapentadecanedinitrileaccording to formula belowN,N’’’-DM-BPA-KDA N1,N1'-((propane-2,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(N3-methylpropane-1,3-diamine)according to formula belowADA 4,4'-(ethane-1,1-diylbis(oxy))bis(butan-1-amine)according to formula belowMCE-ADA 3-((4-(1-(4-aminobutoxy)ethoxy)butyl)amino)propanenitrileaccording to formula belowBCE-ADA 10-methyl-9,11-dioxa-4,16-diazanonadecanedinitrileaccording to formula belowN,N-BCE-ADA 3,3'-((4-(1-(4-aminobutoxy)ethoxy)butyl)azanediyl)dipropanenitrileaccording to formula belowTCE-ADA 4-(2-cyanoethyl)-10-methyl-9,11-dioxa-4,16-diazanonadecanedinitrileaccording to formula belowBPA-ADA N1,N1'-((ethane-1,1-diylbis(oxy))bis(butane-4,1-diyl))bis(propane-1,3-diamine)according to formula belowDADA-1 constitutional isomer 1 (two 5-membered rings): [2,2'-bi(1,3-dioxolane)]-4,4'-diyldimethanamineaccording to formula belowDADA-2 constitutional isomer 2 (5-membered and 6-membered ring): 2-(4-(aminomethyl)-1,3-dioxolan-2-yl)-1,3-dioxan-5-amine; according to formula belowDADA-3 constitutional isomer 3 (two 6-membered rings): [2,2'-bi(1,3-dioxane)]-5,5'-diamineaccording to formula belowBCE-DADA-1 constitutional isomer 1 (two 5-membered rings): 3,3'-(([2,2'-bi(1,3-dioxolane)]-4,4'-diylbis(methylene))bis(azanediyl))dipropanenitrile; according to formula belowBCE-DADA-2 constitutional isomer 2 (5-membered and 6-membered ring): 3-(((2-(5-((2-cyanoethyl)amino)-1,3-dioxan-2-yl)-1,3-dioxolan-4-yl)methyl)amino)propanenitrile; according to formula belowBCE-DADA-3 constitutional isomer 3 (two 6-membered rings): 3,3'-([2,2'-bi(1,3-dioxane)]-5,5'-diylbis(azanediyl))dipropanenitrile; according to formula below BPA-DADA-1 constitutional isomer 1 (two 5-membered rings): N1,N1'-([2,2'-bi(1,3-dioxolane)]-4,4'- diylbis(methylene))bis(propane-1,3-diamine); according to formula belowBPA-DADA-2 constitutional isomer 2 (5-membered and 6-membered ring): N1-((2-(5-((3-aminopropyl)amino)-1,3-dioxan-2-yl)-1,3-dioxolan-4-yl)methyl)propane-1,3-diamine; according to formula belowBPA-DADA-3 constitutional isomer 3 (two 6-membered rings): N1,N1'-([2,2'-bi(1,3-dioxane)]-5,5'-diyl)bis(propane-1,3-diamine); according to formula belowSDA-MEOA 2,2'-((dimethylsilanediyl)bis(oxy))bis(ethan-1-amine)according to formula belowBCE-SDA-MEOA 8,8-dimethyl-7,9-dioxa-4,12-diaza-8-silapentadecanedinitrileaccording to formula belowBPA-SDA-MEOA N1,N1'-(((dimethylsilanediyl)bis(oxy))bis(ethane-2,1-diyl))bis(propane-1,3-diamine)according to formula belowSDA-MMEOA 2,2'-((dimethylsilanediyl)bis(oxy))bis(N-methylethan-1-amine)according to formula belowBCE-SDA-MMEOA 4,8,8,12-tetramethyl-7,9-dioxa-4,12-diaza-8-silapentadecanedinitrileaccording to formula belowBPA-SDA-MMEOA N1,N1'-(((dimethylsilanediyl)bis(oxy))bis(ethane-2,1-diyl))bis(N1-methylpropane-1,3-diamine)according to formula below ACN = acrylonitrile MeOH = methanol MMA = monomethylamine DMA = dimethylamine MEOA-HCl = monoethanolamine hydrochloride THF = tetrahydrofurane BDO = butane-1,4-diolExample 1: Synthesis procedure for KDA, BCE / MCE-KDA and BPA / MPA-KDAThe terms “top“ and “bottom” describe that the respective compound is depicted above or below the other mentioned compound, respectively.Synthesis of KDA KDA was synthesized according to the above standard procedure or obtained commercially. Synthesis of BCE-KDA / MCE-KDAKDA (185 g, 1.14 mol, 1.00 eq.) was charged into a double-jacketed stirred vessel together with MeOH (22.2 g, 0.69mmol, 0.61 eq.). The mixture was heated to 50 °C under stirring (300 rpm). ACN (124 g, 2.34 mol, 2.05 eq.) wasadded over 4 hours while maintaining the internal temperature of the reaction mixture at 50 °C. After the completionof ACN addition, the reaction mixture was stirred for additional 2 hours at 50 °C. The crude product was obtained asa faintly yellowish, clear liquid. The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x0.32 mm); 80 °C – 5 min – 5 °C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min) andNMR spectroscopy. The crude product that was used without any further purification comprised MCE-KDA with 23.1GC-area% and BCE-KDA with 69.9 GC-area% Synthesis of BPA-KDA / MPA-KDA The reaction mixture containing MCE-KDA and BCE-KDA was diluted with THF in a ratio 2:1 (mass ratio) and the resulting solution was used as the feedstock for hydrogenation. In a 300 mL autoclave equipped with a gas- entrainment impeller, Raney-Cobalt Grace 2724 catalyst (5.0 g, 5 wt.% based on MCE-KDA / BCE-KDA reaction mixture without THF dilution) was charged and washed three times with THF (10 mL). After removing the third wash solution, 30 g of THF was added to the Grace catalyst. Subsequently, the autoclave was purged with an inert gas, ammonia (10 g, 10 wt.% based on MCE-KDA / BCE-KDA reaction mixture without THF dilution) was added, and the autoclave was pressurized to 50 bar using hydrogen gas. The autoclave was then heated under stirring (700 rpm) to100 °C, and the final reaction pressure of 180 bar was achieved by further pressurizing with hydrogen. The feedmixture of MCE-KDA / BCE-KDA and THF (100 g reaction mixture containing MCE-KDA and BCE-KDA in 50 g THF) was then added over a period of 8 hours. After the completion of dosing, the reaction mixture was stirred for 4 hours under reaction conditions. Hydrogen was continuously supplied during dosing and post-reaction period to maintain the reaction pressure at 180 bar. After the reaction, the system was cooled and depressurized. This reaction was repeated multiple times to collect sufficient material for distillation. The crude product was obtained as a slightlycloudy, yellowish-greenish liquid, with Raney-Co as a black sediment at the bottom. The reaction mixture wasanalyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5 °C / min – 260 °C – 49 min;Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min) and NMR spectroscopy. The crude product comprised MPA-KDA with 25.4 GC-area% and BPA-KDA with 69.7 GC-area% (excluding THF in the integration).Distillation of BPA-KDA and MPA-KDAThe combined reaction outputs were filtered, and then the solvent and light-boiling components were removed undervacuum. Subsequently, the separation and purification of MPA-KDA and BPA-KDA were carried out using fractional distillation (three-neck flask, packed column, internal temperature thermometer, head temperature thermometer, inertization using N2). The product MPA-KDA was obtained as faintly yellowish, clear liquid. The product BPA-KDA was obtained as colorless, clear liquid. The products were analyzed using gas chromatography (CP-Volamine (30 mx 0.32 mm); 80 °C – 5 min – 5 °C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min) andNMR spectroscopy. MPA-KDA was obtained with a purity of 93 GC area% and BPA-KDA was obtained with a purityof 96 GC area%. The products MPA-KDA and BPA-KDA were obtained with distillations yields of 71 and 81 %,respectively. The distillation yields were calculated by dividing the mass of each product within the isolated product fraction by the mass of the respective product in the crude product to be distilled.Example 2: Influence of MeOH in the synthesis of BCE-KDASynthesis of BCE-KDA using 100 g KDA per reaction: KDA (100 g, 616 mmol, 1.00 eq., >99 GC area% purity) was charged into a double-jacketed stirred vessel togetherwith different amounts of MeOH (see table 1 below). The mixture was heated to 50 °C under stirring (300 rpm). ACN(67.1 g, 1.26 mol, 2.05 eq.) was added over 4 hours while maintaining the internal temperature of the reactionmixture at 50 °C. After the completion of ACN addition, the reaction mixture was stirred for an additional 2 hours at50 °C. The crude product was obtained as a faintly yellowish, clear liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The respective crude productcomposition is shown in the table 1 below. No TCE-KDA formation was observed.Product characterization was performed using GC-MS and NMR spectroscopy.Table 1 Results of the BCE-KDA synthesis using 100 g KDA per reaction with different amounts of MeOH. MCE- N,N- MeO BCE- Molar ra H ACN KDA BCE- Others # tio MeOH [GC [GC [GC KDA KD KDA MeOH / KDA A [GC area%] area%] area%] [GC [GC area%] [GC area%] area%] area%] 0.00 5.43 1.44 28.16 2.05 62.22 0.701 0 0Excluded 5.43 1.44 28.16 2.05 62.22 0.701731.22 2.15 0.27 16.44 0.58 78.90 0.442 0.28mmolExcluded 2.18 0.28 16.64 0.59 79.87 0.441.7314.29 1.62 0.00 0.82 0.00 82.68 0.593 2.80molExcluded 1.89 0.00 0.95 0.00 96.46 0.70Synthesis of BCE-KDA using 50 g KDA per reaction & 60 °C post-reaction temperature:KDA (50 g, 308 mmol, 1.00 eq., >99 GC area% purity) was charged into a double-jacketed stirred vessel togetherwith different amounts of MeOH (see table 2 below). The mixture was heated to 50 °C under stirring (300 rpm). ACN(33.5 g, 632 mmol, 2.05 eq.) was added over 4 hours while maintaining the internal temperature of the reactionmixture at 50 °C. After the completion of ACN addition, the reaction mixture was stirred for an additional 3 hours at60 °C. The crude product was obtained as a faintly yellowish, clear liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The respective crude productcomposition is shown in the table 2 below. No TCE-KDA formation was observed.Product characterization was performed using GC-MS and NMR spectroscopy. Table 2Results of the BCE-KDA synthesis using 50 g KDA per reaction and 60 °C post-reaction temperature with differentamounts of MeOH. MC N,N- Molar ratio MeOH ACN KDA E- K BCE- BCE- Others # MeOH [G DA KDA MeOH / KDA C [GC [GC [GC KDA [ [GC area%] area%] area%] area%] [GC GC ar area%] area%] ea%] 0.06 0.10 2.48 34.83 2.30 58.90 1.331 0 0Excluded 0.10 2.48 34.85 2.30 58.93 1.342 0.28 0.54 1.02 0.21 15.56 0.69 81.11 0.8786.3 Excluded 1.02 0.22 15.65 0.70 81.55 0.87mmol 86313.19 0.42 0.00 1.62 0.00 83.63 1.143 2.80mmolExcluded 0.49 0.00 1.87 0.00 96.33 1.31Example 3: Influence of H2O in the synthesis of BCE-KDASynthesis of BCE-KDA using 50 g KDA per reaction & 60 °C post-reaction temperature:KDA (50 g, 308 mmol, 1.00 eq., >99 GC area% purity) was charged into a double-jacketed stirred vessel togetherwith different amounts of H2O (see table 3 below). The mixture was heated to 50 °C under stirring (300 rpm). ACN(33.5 g, 632 mmol, 2.05 eq.) was added over 4 hours while maintaining the internal temperature of the reactionmixture at 50 °C. After the completion of ACN addition, the reaction mixture was stirred for an additional 3 hours at60 °C. The crude product was obtained as a faintly yellowish, clear liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The respective crude productcomposition is shown in the table 3 below. No TCE-KDA formation was observed. Product characterization was performed using GC-MS and NMR spectroscopy. Table 3Results of the BCE-KDA synthesis using 50 g KDA per reaction and 60 °C post-reaction temperature with differentamounts of H2O. ACN KDA MCE- N,N-BCE- Mol KDA BCE-KDA Others # ar ratio HO [GC [G KDA H / KDA 2 2O C [GC [ [GC [GC area%] area%] area%] GC area%] area%] area%]1 0 0 0.10 2.48 34.83 2.30 58.90 1.3386.3 20.28 2.41 0.11 6.47 0.09 84.58 6.24mmol 863 32.80 1.24 1.07 4.56 0.00 88.67 4.47mmolExample 4: Synthesis procedure for N,N’’’-DM-BPA-KDASynthesis of KDA KDA was synthesized according to the above standard procedure or obtained commercially. Synthesis of BCE-KDA: KDA (270 g, 1.66 mol, 1.00 eq.) was charged into a double-jacketed stirred vessel together with MeOH (32.4 g, 1.01mmol, 0.61 eq.). The mixture was heated to 50 °C under stirring (300 rpm). ACN (181 g, 3.41 mol, 2.05 eq.) wasadded over 4 hours while maintaining the internal temperature of the reaction mixture at 50 °C. After the completionof ACN addition, the reaction mixture was stirred for an additional 2 hours at 50 °C. The crude product (421 g) wasobtained as a faintly yellowish, clear liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The crude product that was usedwithout any further purification comprised BCE-KDA with 81.9 GC area%. Product characterization was performed using GC-MS and NMR spectroscopy. Synthesis of N,N’’’-DM-BPA-KDA: The reaction mixture containing BCE-KDA was diluted with THF in a mass ratio 3:1 (BCE-KDA:THF) and the resulting solution was used as the feedstock for hydrogenation. In a 300 mL autoclave equipped with a gas- entrainment impeller and a catalyst basket, a palladium catalyst (0.75 wt.% Pd on Al2O3; 22.5 g, 50 wt.% based on BCE-KDA reaction mixture without THF dilution) together with THF (15.0 g) was charged. Subsequently, theautoclave was purged first with an inert gas and afterwards with hydrogen gas. MMA (54.0 g, 1.74 mol) was added, and the autoclave was pressurized to 30 bar using hydrogen gas. The autoclave was then heated under stirring (700rpm) to 130 °C, and the autoclave was further pressurized to 170 bar with hydrogen gas. The feed mixture of BCE-KDA and THF (60.0 g) was then added over a period of 6 hours. After the completion of dosing, the reaction pressure was increased to 180 bar by further pressurizing with hydrogen gas and the reaction mixture was stirred for 12 hours under reaction conditions. Hydrogen gas was continuously supplied during dosing and post-reaction period to maintain the reaction pressure at 170 and 180 bar, respectively. After the reaction, the system was cooled and depressurized. The crude product (58.1 g) was obtained as a clear, yellowish liquid.The reaction mixture was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2min – 8 °C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 18 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1mL / min). The crude product comprised N,N’’’-DM-BPA-KDA with 72.0 GC area% (excluding THF and the stabilizer of THF in the integration). Product characterization was performed using GC-MS and NMR spectroscopy. This reaction was repeated multiple times to collect sufficient material for distillation. By this, 310 g of BCE-KDA reaction mixture was used for the synthesis of N,N’’’-DM-BPA-KDA crude product. Distillation of N,N’’’-DM-BPA-KDA: The combined crude products were filtered prior to the distillation. An aliquot (132 g, 24.5 GC area% N,N’’’-DM-BPA- KDA, 68.2 GC area% N,N’’’-DM-BPA-KDA excluding THF and the stabilizer of THF in the integration, ca.32.3 g pure N,N’’’-DM-BPA-KDA) of the resulting combined crude products was taken. The separation and purification of N,N’’’- DM-BPA-KDA was carried out using fractional distillation (three-neck flask, Vigreux column, internal temperature thermometer, head temperature thermometer, inertization using N2, reflux divider). The product N,N’’’-DM-BPA-KDAwas collected at a head temperature of 158 °C at a pressure below 1 mbar and was obtained as light blue, clearliquid (22.7 g).The product was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2 min – 8°C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 18 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1 mL / min).N,N’’’-DM-BPA-KDA was obtained with a purity of 90.5 GC area% (ca.20.5 g pure N,N’’’-DM-BPA-KDA). The product N,N’’’-DM-BPA-KDA was obtained with a distillation yield of 63 %. The distillation yield was calculated by dividing the mass of the product within the isolated product fraction by the mass of the product in the crude product to be distilled. Product characterization was performed using GC-MS and NMR spectroscopy.Example 5: Synthesis procedure for BPA-ADASynthesis of bis-BDO acetal: In a 5 L glass reactor, 2390 g (26.5 mol) of 1,4-butanediol and 640 mg (6.66 mmol) of methanesulfonic acid wereplaced, and 770 g (6.63 mol) of hydroxybutyl vinyl ether was added dropwise over 3 hours at 25-30 °C. The mixturewas stirred for an additional 2 hours at room temperature and was then neutralized with 14 mL of 1 molar sodiumhydroxide. All volatile components were distilled off at 150 °C and 1 mbar. The crude product (715 g) was obtainedas a clear liquid.The reaction mixture was analyzed using gas chromatography (Optima-Wax (30 m x 0.25 mm x 0.25 µm); 40 °C – 5min – 10 °C / min – 240 °C – 35 min; Inj. / Det.: 250 °C / 250 °C; split: 50:1; N2; 1.092 mL / min). The crude productthat was used without further purification comprised bis-BDO acetal with 88 GC area%, tris-BDO diacetal with 10 GC area% and 1,4-butanediol with 2 GC area% besides the added sodium hydroxide / sodium methanesulfonate. Synthesis of ADA:In a 2.5 L autoclave equipped with a mechanical stirrer, a temperature and pressure sensor, a gas inlet and anelectrical heating mantle, a Ni, Co, Cu on alumina catalyst (100 g), as described in WO 2011 / 067199 A1, contained in a wire mesh basket, was placed. The autoclave was purged with inert gas and the catalyst was activated under hydrogen gas. A mixture of bis-BDO acetal reaction product (300 g, 1.45 mol, 1 eq.) in 300 g THF was added. Subsequently, the autoclave was purged with inert gas, ammonia (495 g, 29.1 mol, 20 eq.) was added and the autoclave was pressurized to 50 bar using hydrogen gas. The autoclave was then heated under stirring (700 rpm) to180 °C, and the final reaction pressure of 180 bar was achieved by further pressurizing with hydrogen. The reactionmixture was stirred for 15 hours under reaction conditions. Hydrogen gas was continuously supplied during the reaction to maintain the reaction pressure at 180 bar. After the reaction, the system was cooled and depressurized. The crude product (514 g) was obtained as a slightly cloudy, grayish liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The crude product comprised ADAwith 66.3 GC area%, the intermediate mono-alcohol aminated bis-BDO acetal with 4.9 GC area%, bis-BDO acetal asreactant with 0.1 GC area% and the di-alcohol aminated tris-BDO diacetal with 15.8 GC area% (excluding THF and the stabilizer of THF in the integration). The conversion for bis-BDO acetal was >99 % and the selectivity towards ADA was 85 %. This reaction was repeated twice (300 g and 235 g bis-BDO acetal as reactant, 78.3 GC area% bis-BDO acetal analyzed using CP-Volamine, ca.418 g pure bis-BDO acetal) to collect sufficient material for distillation (965 g combined crude product). Distillation of ADA: The reaction outputs were filtered, combined and then the solvent and light-boiling components were removed undervacuum resulting in the crude product to be distilled (417 g, 67.5 GC area% ADA, ca.281 g pure ADA).Subsequently, the separation and purification of ADA was carried out using fractional distillation (three-neck flask, packed column, internal temperature thermometer, head temperature thermometer, inertization using N2, automaticreflux distributor). The product ADA was collected at a head temperature of 125 °C at a pressure of 4 mbar and wasobtained as colorless, clear liquid (133 g).The product was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5 °C / min –260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). ADA was obtained with a purity of 98.3 GCarea% (ca.130 g pure ADA). The product ADA was obtained with a distillation yield of 46 %. The distillation yield was calculated by dividing the mass of the product within the isolated product fraction by the mass of the product in the crude product to be distilled. Product characterization was performed using GC-MS and NMR spectroscopy. Synthesis of BCE-ADA: ADA (50.0 g, 245 mmol, 1.00 eq.) was charged into a double-jacketed stirred vessel together with MeOH (2.20 g,68.5 mmol, 0.28 eq.). The mixture was heated to 50 °C under stirring (300 rpm). ACN (26.6 g, 502 mmol, 2.05 eq.)was added over 4 hours while maintaining the internal temperature of the reaction mixture at 50 °C. After thecompletion of ACN addition, the reaction mixture was stirred for an additional 3 hours at 60 °C. The crude product(75.7 g) was obtained as a colorless, clear liquid.The reaction mixture was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2min – 8 °C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 27.5 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1mL / min). The crude product that was used without any further purification comprised BCE-ADA with 87.9 GC area%.Product characterization was performed using GC-MS and NMR spectroscopy. Synthesis of BPA-ADA: The reaction mixture containing BCE-ADA was diluted with THF in a mass ratio 30:70 (BCE-ADA:THF) and the resulting solution was used as the feedstock for hydrogenation. In a 300 mL autoclave equipped with a gas- entrainment impeller, Raney-Cobalt Grace 2724 catalyst (1.5 g, 5 wt.% based on BCE-ADA reaction mixture without THF dilution) was charged and washed three times with THF (10 mL). After removing the third wash solution, 30 g of THF was added to the Grace catalyst. Subsequently, the autoclave was purged first with an inert gas and afterwards with hydrogen gas. Ammonia (6 g, 20 wt.% based on BCE-ADA reaction mixture without THF dilution) was added, and the autoclave was pressurized to 50 bar using hydrogen gas. The autoclave was then heated under stirring (700rpm) to 100 °C, and the autoclave was further pressurized to 160 bar with hydrogen gas. The feed mixture of BCE-ADA and THF was then added over a period of 8 hours. After the completion of dosing, the reaction pressure was increased to 180 bar by further pressurizing with hydrogen gas and the reaction mixture was stirred for 8 hours under reaction conditions. Hydrogen gas was continuously supplied during dosing and post-reaction period to maintain the reaction pressure at 160 and 180 bar, respectively. After the reaction, the system was cooled and depressurized. The crude product (106 g) was obtained as a slightly cloudy, yellowish liquid, with Raney-Co as a black sediment at the bottom.The reaction mixture was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2min – 8 °C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 27.5 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1mL / min). The crude product comprised BPA-ADA with 88.9 GC area% (excluding THF and the stabilizer of THF in the integration). Product characterization was performed using GC-MS and NMR spectroscopy.Example 6: Influence of MeOH in the synthesis of BCE-ADASynthesis of BCE-ADA using 50 g ADA per reaction & 60 °C post-reaction temperature:ADA (50.0 g, 245 mmol, 1.00 eq.) was charged into a double-jacketed stirred vessel together with different amountsof MeOH (see table 4 below). The mixture was heated to 50 °C under stirring (300 rpm). ACN (26.6 g, 502 mmol,2.05 eq.) was added over 4 hours while maintaining the internal temperature of the reaction mixture at 50 °C. Afterthe completion of ACN addition, the reaction mixture was stirred for an additional 3 hours at 60 °C. The crudeproduct was obtained as a faintly yellowish, clear liquid.The reaction mixture was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2min – 8 °C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 27.5 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1mL / min). The respective crude product composition is shown in the table 4 below. Product characterization was performed using GC-MS and NMR spectroscopy. Table 4Results of the BCE-ADA synthesis using 50 g ADA per reaction and 60 °C post-reaction temperature with differentamounts of MeOH. MCE- N,N- MeOH ACN ADA BC BCE- TCE- Molar ratio A E- Others # MeOH [GC [GC [ DA ADA ADA MeOH / ADA GC ea%] [GC ADA [GC area%] area%] ar [GC [GC area%] [GC area%] area%] area%] area%] 0.13 0.03 10.32 43.33 0.97 39.23 1.29 4.701 0 0Excluded 0.03 10.33 43.39 0.97 39.28 1.29 4.7168.51.66 0.73 0.04 2.24 0.00 87.92 3.55 3.862 0.28mmolExcluded 0.74 0.04 2.28 0.00 89.40 3.61 3.93Example 7: Synthesis procedure for BPA-DADASynthesis of DADA: 100 g of a reduced-passivated catalyst containing Cu, Ni, Co and aluminium oxide, prepared according to WO2011067199 A1, example 5, were filled into a basket and placed in a 2.5 L autoclave with electrical heating, a hydrogen supply line, temperature and pressure sensors and mechanical stirrer (disc type). The autoclave wasclosed and purged with nitrogen at 10 bars. Then, it was pressurized with hydrogen to 50 bars and heated in about0.7 °C / min to 260 °C. The pressure was increased with hydrogen to 85 bar and the autoclave was maintained atthese conditions in order to reduce the catalyst. After 12 h, it was allowed to cool down and cautiously depressurizedto ambient pressure. The autoclave was again purged with nitrogen, and 200 g of a diacetal (obtained according toDD253180 A1 from glycerol and glyoxal, purity by GC 94 %) and 200 g of tetrahydrofuran were sucked in. After purging again with nitrogen at 5 bars, 500 g of liquid ammonia were added with a high-pressure pump. The autoclave was pressurized with hydrogen to 10 bars, the stirrer was switched on, the speed adjusted to 800 rpm, and theautoclave was heated to 180 °C. The pressure was increased to 200 bar with hydrogen, and the autoclavemaintained at these conditions for 24 h, before it was again allowed to cool to room temperature and depressurized. The reaction mixture was removed, and solvent was evaporated at a rotavapor. The residue was transferred into a 250 mL 3-neck-flask and distilled over a Vigreux column with 15 cm length and 4 cm inner diameter without refluxdivisor at 2-10 mbar. One fraction (77 g) was collected at 175-190 °C sump temperature and 150-160 °C headtemperature at 2 mbar and one fraction (47 g) at 190-200 °C sump temperature and 160-165 °C head temperature at1 mbar. Both fractions were analyzed by gas chromatography on a Volamin column with 30 m length, a diameter of320 micrometer and film thickness of 5 micrometer. Temperature program: 40 °C, 2 min holding time, 8 °C / minheating to 230 °C, 3.75 min holding time, 20 °C / min heating to 290 °C, 30 min holding time. Temperature ofinj. / detector 250 °C / 300 °C, gas flow 1mL / min of N2, split: 50:1. The first fraction contained 87 % of various isomersof the aminated bisacetal, and the second fraction 93 % as evidenced by GC-MS and NMR. In all, 8 isomers were detected by GC and found to have an identical relative molecular mass of 204 with ionization by electron impact and chemical ionization. Synthesis of BCE-DADA: DADA (50.0 g, 245 mmol, 1.00 eq.) was charged into a double-jacketed stirred vessel together with MeOH (2.20 g,68.6 mmol, 0.28 eq.). The mixture was heated to 50 °C under stirring (300 rpm). ACN (26.6 g, 502 mmol, 2.05 eq.)was added over 4 hours while maintaining the internal temperature of the reaction mixture at 50 °C. After thecompletion of ACN addition, the reaction mixture was stirred for an additional 3 hours at 60 °C. The crude product(74.2 g) was obtained as a colorless, clear liquid.The reaction mixture was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2min – 8 °C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 27.5 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1mL / min). The crude product comprised BCE-DADA isomers with 62.6 GC area%, together with 18.3 GC area% of the intermediate mono-cyanoethylated DADA isomers and 9.7 GC area% ACN. Product characterization was performed using GC-MS and NMR spectroscopy. Synthesis of BPA-DADA: The reaction mixture containing BCE-DADA was diluted with THF in a mass ratio 30:70 (BCE-DADA:THF) and the resulting solution was used as the feedstock for hydrogenation. In a 300 mL autoclave equipped with a gas- entrainment impeller, Raney-Cobalt Grace 2724 catalyst (1.5 g, 5 wt.% based on BCE-DADA reaction mixture without THF dilution) was charged and washed three times with THF (10 mL). After removing the third wash solution,30 g of THF was added to the Grace catalyst. Subsequently, the autoclave was purged first with an inert gas andafterwards with hydrogen gas. Ammonia (6 g, 20 wt.% based on BCE-DADA reaction mixture without THF dilution) was added, and the autoclave was pressurized to 50 bar using hydrogen gas. The autoclave was then heated understirring (700 rpm) to 80 °C, and the autoclave was further pressurized to 160 bar with hydrogen gas. The feedmixture of BCE-DADA and THF was then added over a period of 8 hours. After the completion of dosing, the reaction pressure was increased to 180 bar by further pressurizing with hydrogen gas and the reaction mixture was stirred for 12 hours under reaction conditions. Hydrogen gas was continuously supplied during dosing and post-reaction period to maintain the reaction pressure at 160 and 180 bar, respectively. After the reaction, the system was cooled and depressurized. The crude product (108 g) was obtained as a slightly cloudy, yellowish liquid, with Raney-Co as a black sediment at the bottom.The reaction mixture was analyzed using gas chromatography (RTX5-Amine (30 m x 0.25 mm x 0.25 µm); 40 °C – 2min – 8 °C / min – 230 °C – 3.75 min – 20 °C / min – 290 °C – 27.5 min; Inj. / Det.: 250 °C / 300 °C; split: 50:1; N2; 1mL / min). The crude product comprised BPA-DADA isomers with 55.3 GC area% (excluding THF and the stabilizer ofTHF in the integration). Product characterization was performed using GC-MS and NMR spectroscopy.Example 8: Synthesis procedure for BPA-SDA-MEOASynthesis of SDA-MEOA: Monoethanolamine (367 g, 6.00 mol, 2.40 eq.) was added to a 1L four-neck flask (stirrer, packed column, internal temperature thermometer, dropping funnel). Dimethoxydimethylsilane (316 g, 95 % purity, 2.50 mol, 1.00 eq.) was added via dropping funnel within minutes while stirring the mixture at 300 rpm. The mixture was stirred for 30 min atroom temperature before it was heated up using an oil bath with a final oil bath temperature of 110 °C until aninternal temperature of 95-96 °C was reached under complete reflux (63-65 °C head temperature). The reactionmixture was stirred under these conditions for 2h. Then, light-boiling components were distilled off and based on thespeed of distillation, the temperature was successively increased. After an internal temperature of 150 °C wasreached, the reaction mixture was stirred under these conditions for 3h. The crude product (487 g) was obtained as a colorless, clear liquid.The crude product was analyzed using gas chromatography (RTX Volatile Amine (60 m x 0.32 mm x 5 µm); 40 °C –5 min – 20 °C / min – 140 °C – 10 °C / min – 200 °C – 20 °C / min – 290 °C – 35 min; Inj. / Det.: 200 °C / 300 °C; split:50:1; N2; 2 mL / min). The crude product comprised SDA-MEOA with 43.3 GC area%. This reaction was repeated multiple times to collect sufficient material for distillation (1606 g, 43.3 GC area% SDA- MEOA). Distillation of SDA-MEOA: The separation and purification of SDA-MEOA was carried out using fractional distillation (three-neck flask, packed column, internal temperature thermometer, head temperature thermometer, inertization using N2, reflux divider). Theproduct SDA-MEOA was collected at a head temperature of 68-71 °C at a pressure of ca.3 mbar and was obtainedas colorless, clear liquid (681 g).The product was analyzed using gas chromatography (RTX Volatile Amine (60 m x 0.32 mm x 5 µm); 40 °C – 5 min– 20 °C / min – 140 °C – 10 °C / min – 200 °C – 20 °C / min – 290 °C – 35 min; Inj. / Det.: 200 °C / 300 °C; split: 50:1;N2; 2 mL / min). SDA-MEOA was obtained with a purity of 93.2 GC area% (ca.634 g pure SDA-MEOA).The product SDA-MEOA was obtained with a distillation yield of 91 %. The distillation yield was calculated by dividing the mass of the product within the isolated product fraction by the mass of the product in the crude product to be distilled. Product characterization was performed using NMR spectroscopy.Synthesis of BCE-SDA-MEOA: SDA-MEOA (100.0 g, 561 mmol, 1.00 eq.) was charged into a double-jacketed stirred vessel. The mixture washeated to 50 °C under stirring (300 rpm). ACN (61.0 g, 1.15 mol, 2.05 eq.) was added over 3 hours while maintainingthe internal temperature of the reaction mixture at 50 °C. After the completion of ACN addition, the reaction mixturewas stirred for an additional 4 hours at 60 °C. The crude product (160 g) was obtained as a colorless, clear liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The crude product that was usedwithout any further purification comprised BCE-SDA-MEOA with 82.6 GC area%. Product characterization was performed using GC-MS and NMR spectroscopy. Synthesis of BPA-SDA-MEOA: The reaction mixture containing BCE-SDA-MEOA was diluted with THF in a mass ratio 45:10 (BCE-SDA- MEOA:THF) and the resulting solution was used as the feedstock for hydrogenation. In a 300 mL autoclave equipped with a gas-entrainment impeller, Raney-Cobalt Grace 2724 catalyst (3.7 g, 10 wt.% based on BCE-SDA-MEOA) was charged and washed three times with THF (10 mL). After removing the third wash solution, 20 g of THF was added to the Grace catalyst and the BCE-SDA-MEOA solution in THF (55 g) was added as well. Subsequently, the autoclave was purged first with an inert gas and afterwards with hydrogen gas. The autoclave was pressurized to 50bar using hydrogen gas. The autoclave was then heated under stirring (700 rpm) to 50 °C, and the autoclave wasfurther pressurized to 180 bar with hydrogen gas. The reaction mixture was stirred for 96 hours under reaction conditions. Hydrogen gas was continuously supplied during the reaction period to maintain the reaction pressure at 180 bar. After the reaction, the system was cooled and depressurized. The crude product (71.3 g) was obtained as a slightly cloudy, yellowish liquid, with Raney-Co as a black sediment at the bottom. The catalyst was removed via filtration, followed by removal of volatiles from the crude product. Product analysis and characterization was performed using NMR spectroscopy. The obtained product comprised BPA-SDA-MEOA with ca.30 mol%.Example 9: Synthesis procedure for BPA-SDA-MMEOASynthesis of SDA-MMEOA: N-Methylethanolamine (413 g, 5.50 mol, 2.40 eq.) was added to a 1L four-neck flask (stirrer, packed column, internal temperature thermometer, dropping funnel). Dimethoxydimethylsilane (290 g, 95 % purity, 2.29 mol, 1.00 eq.) was added via dropping funnel within minutes while stirring the mixture at 400 rpm. The mixture was heated up using anoil bath with a final oil bath temperature of 120 °C until an internal temperature of 97-98 °C was reached undercomplete reflux (62-63 °C head temperature). The reaction mixture was stirred under these conditions for 2h. Then,light-boiling components were distilled off and based on the speed of distillation, the temperature was successivelyincreased. After an internal temperature of 150 °C was reached, the reaction mixture was stirred under theseconditions for 3h. The crude product (515 g) was obtained as a colorless, clear liquid.The crude product was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The crude product comprised SDA-MMEOA with 41.8 GC area%. This reaction was repeated multiple times to collect sufficient material for distillation (950 g, 39.8 GC area% SDA- MMEOA). Distillation of SDA-MMEOA: The separation and purification of SDA-MMEOA was carried out using fractional distillation (three-neck flask, packed column, internal temperature thermometer, head temperature thermometer, inertization using N2, reflux divider). Theproduct SDA-MMEOA was collected at a head temperature of 75-76 °C at a pressure of ca.4 mbar and wasobtained as colorless, clear liquid (387 g).The product was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5 °C / min –260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). SDA-MMEOA was obtained with a purity of93.3 GC area% (ca.361 g pure SDA-MMEOA). The product SDA-MMEOA was obtained with a distillation yield of 95 %. The distillation yield was calculated by dividing the mass of the product within the isolated product fraction by the mass of the product in the crude product to be distilled. Product characterization was performed using NMR spectroscopy. Synthesis of BCE-SDA-MMEOA:SDA-MMEOA (100.0 g, 93 % purity, 451 mmol, 1.00 eq.) was charged into a double-jacketed stirred vessel. Themixture was heated to 50 °C under stirring (300 rpm). ACN (48.1 g, 906 mmol, 2.01 eq.) was added over 3 hourswhile maintaining the internal temperature of the reaction mixture at 50 °C. After the completion of ACN addition, thereaction mixture was stirred for an additional 4 hours at 60 °C. The crude product (151 g) was obtained as acolorless, clear liquid.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The crude product comprised BCE-SDA-MMEOA with 88.7 GC area%.To complete conversion and remove remaining ACN residues, the reaction mixture was heated to 60 °C at 1 mbarfor 2h.The reaction mixture was analyzed using gas chromatography (CP-Volamine (30 m x 0.32 mm); 80 °C – 5 min – 5°C / min – 260 °C – 49 min; Inj. / Det.: 250 °C / 300 °C, split: 50:1; N2; 1 mL / min). The crude product that was usedwithout any further purification comprised BCE-SDA-MMEOA with 92.1 GC area%. Product characterization was performed using NMR spectroscopy. Synthesis of BPA-SDA-MMEOA: The reaction mixture containing BCE-SDA-MMEOA was directly used without further dilution as the feedstock for hydrogenation. In a 300 mL autoclave equipped with a gas-entrainment impeller, Raney-Cobalt Grace 2724 catalyst (6.9 g, 10 wt.% based on BCE-SDA-MMEOA) was charged and washed three times with THF (10 mL). After removing the third wash solution, the BCE-SDA-MMEOA reaction mixture (75.0 g, 92 % purity, 221 mmol) was added. Subsequently, the autoclave was purged first with an inert gas and afterwards with hydrogen gas. Theautoclave was pressurized to 50 bar using hydrogen gas. The autoclave was then heated under stirring (700 rpm) to50 °C, and the autoclave was further pressurized to 180 bar with hydrogen gas. The reaction mixture was stirred for96 hours under reaction conditions. Hydrogen gas was continuously supplied during the reaction period to maintain the reaction pressure at 180 bar. After the reaction, the system was cooled and depressurized. The crude product (73.1 g) was obtained as a slightly cloudy, greyish liquid, with Raney-Co as a black sediment at the bottom. The catalyst was removed via filtration, followed by removal of volatiles from the crude product. Product analysis and characterization was performed using NMR spectroscopy. The obtained product comprised BPA-SDA-MMEOA with ca.40 mol%.

Claims

Claims 1. A process for preparing polyamines via (meth)acrylonitrile and / or crotononitrile addition to an amine followed by hydrogenation in the presence of a catalyst and hydrogen and optionally in the additional presence of ammonia, primary and / or secondary amine, comprisinga) reacting at least one amine of general formula (I)with (meth)acrylonitrile and / or crotononitrile, wherein the amine of general formula (I) comprises at least one, preferably terminal, group NH which is reacted with the (meth)acrylonitrile and / or crotononitrile, thereby obtaining at least one first intermediate (I1), wherein at least one, preferably terminal, group NH of the amine of general formula (I) is converted to a group N-CH2-CHR-CN or to a group N-CHR-CH2-CN with R being H or methyl, preferably to a group N-CH2-CH2-CN; b) hydrogenating the at least one first intermediate (I1) to at least one polyamine compound (II),comprising converting the at least one group N-CH2-CHR-CN or group N-CHR-CH2-CN, preferably the at least one group N-CH2-CH2-CN, to at least one group N-CH2-CHR-CH2-NH2or group N-CHR-CH2-CH2-NH2,preferably to at least one group N-CH2-CH2-CH2-NH2; or hydrogenating the at least one first intermediate (I1) in the additional presence of ammonia, primary and / or secondary amine HNR’R” with R’ being H, C1-C3-alkyl, preferably H, methyl or ethyl, R” being H, C1-C3-alkyl, preferably H, methyl or ethyl, to at least one polyamine compound (III), comprising converting the at least one group N-CH2-CHR-CN or group N-CHR-CH2-CN, preferably the at least one group N-CH2-CH2-CN, to at least one group N-CH2-CHR-CH2-NR’R” or group N-CHR-CH2-CH2-NR’R”, preferably to at least one group N-CH2-CH2-CH2-NR’R” wherein X is C or Si or HC-CH; wherein a1, a2, b1, b2, c1, c2, d1, d2 are independently of each other 0 or 1, with a1 + b1 + c1 + d1 ≥ 2 and a2 + b2 + c2 + d2 ≥ 2; wherein, if a1 = a2 = 0, YA1is H or optionally substituted C1-C12-alkyl; wherein, if a1 = 1 and a2 = 0, YA1is optionally substituted C1-C12-alkyl;wherein, if a1 = a2 = 1, or if a1 = 0 and a2 = 1, YA1is optionally substituted C1-C12-alkylene; wherein, if b1 = b2 = 0, YB1is H or optionally substituted C1-C12-alkyl; wherein, if b1 = 1 and b2 = 0, YB1is optionally substituted C1-C12-alkyl; wherein, if b1 = b2 = 1, or if b1 = 0 and b2 = 1, YB1is optionally substituted C1-C12-alkylene; wherein, if c1 = c2 = 0, YC1is H or optionally substituted C1-C12-alkyl; wherein, if c1 = 1 and c2 = 0, YC1is optionally substituted C1-C12-alkyl; wherein, if c1 = c2 = 1, or if c1 = 0 and c2 = 1, YC1is optionally substituted C1-C12-alkylene; wherein, if d1 = d2 = 0, YD1is H or optionally substituted C1-C12-alkyl; wherein, if d1 = 1 and d2 = 0, YD1is optionally substituted C1-C12-alkyl; wherein, if d1 = d2 = 1, or if d1 = 0 and d2 = 1, YD1is optionally substituted C1-C12-alkylene; wherein RA2, RA3, RB2, RB3, RC2, RC3, RD2, RD3are, independently of each other, H or optionally substituted C1- C12-alkyl, with at least one of RA2, RA3, RB2, RB3, RC2, RC3, RD2, and RD3 being H;wherein, if X is C or Si -YA1 and YB1 can be covalently linked to form a 5- or 6-membered ring with X, preferably whena1 = b1 = 1; and / or -YC1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably whenc1 = d1 = 1; wherein, if X is HC-CH and (O)a1(O)b1X(O)c1(O)d1 isthen -YA1 and YC1 can be covalently linked to form a 5- or 6-membered ring with X, preferably whena1 = c1 = 1; and / or -YB1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably whenb1 = d1 = 1; or -YA1 and YB1 can be covalently linked to form a 5- or 6-membered ring with X, preferably whena1 = b1 = 1; and / or -YC1 and YD1 can be covalently linked to form a 5- or 6-membered ring with X, preferably whenc1 = d1 = 1.

2. The process of claim 1, wherein X is HC-CH and a1 + b1 + c1 + d1 = 2, wherein a1 = c1 = 1 or b1 = d1 = 1.

3. The process of claim 1, wherein X is HC-CH and a1 = b1 = c1 = d1 = 1.

4. The process of any one of claims 1 to 3, wherein reacting at least one amine of general formula (I) accordingto a) is carried out in the presence of at least one polar protic solvent.

5. The process of any one of claims 1 to 4, wherein when X is C, the at least one amine of general formula (I),the intermediate (I1), the polyamine compound (II) and the polyamine compound (III) have a molecular weight of at most 480 g / mol.

6. The process of any one of claims 1 to 5, wherein- reacting at least one amine of general formula (I) according to a) exhibits one or more of the followingfeatures: -- it is carried out at a temperature in the range of from 10 to 150 °C, preferably in the range offrom 20 to 100 °C, more preferably in the range of from 30 to 80 °C;-- it is carried out at a pressure in the range of from 0.8 to 1.2 bar(abs), preferably in the range offrom 0.9 to 1.1 bar(abs), more preferably at ambient pressure of 1.0 bar(abs);-- the at least one amine of general formula (I) and the (meth)acrylonitrile and / or crotononitrile areemployed at a molar ratio of the (meth)acrylonitrile and / or crotononitrile relative to the reactive amino groups of the at least one amine of general formula (I) in the range of from 0.80 to 1.25, preferably in the range of from 0.90 to 1.15, more preferably in the range of from 1.00 to 1.05;- wherein hydrogenating the at least one first intermediate (I1) to at least one polyamine according to b)exhibits one or more of the following features: -- it is carried out at a temperature in the range of from 20 to 200 °C, preferably in the range offrom 40 to 160 °C, more preferably in the range of from 50 to 140 °C; -- it is carried out at a pressure in the range of from 1 to 325 bar(abs), preferably in the range offrom 10 to 200 bar(abs), more preferably in the range of from 60 to 190 bar(abs); -- it is carried out at a molar ratio of ammonia, primary and / or secondary amine HNR‘R‘‘ to cyanogroups in the intermediate (I1) in the range of from 0.1 to 40, preferably in the range of from 0.5 to 20, more preferably in the range of from 1.0 to 10;- one or more additives are employed for the hydrogenation of the at least one first intermediate (I1) toat least one polyamine according to b), the one or more additives preferably comprising at least one basic additive, wherein the at least one basic additive preferably comprises one or more of at least one basic metal salt and ammonia, more preferably one or more of at least one alkali hydroxide and ammonia, more preferably one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide and ammonia, more preferably one or more of lithium hydroxide and ammonia;- the catalyst used for the hydrogenation of the at least one first intermediate (I1) according to b) is aheterogeneous catalyst, preferably a heterogeneous catalyst in the form of a suspension or a fixed-bed catalyst, wherein, preferably or optionally, the catalyst is supported on a suitable supporting materialwhich preferably comprises one or more of charcoal, at least one aluminum oxide, at least one silicon oxide, at least one titanium oxide and at least one zirconium oxide, wherein -- the catalyst used for the hydrogenation of the at least one first intermediate (I1) according to b)to at least one polyamine compound with at least one primary amino group, initially in the presence of no amine or of ammonia, preferably comprises one or more of nickel, cobalt and ruthenium, wherein more preferably, the catalyst comprises cobalt and optionally consists of cobalt, wherein more preferably, the catalyst comprises, optionally consists of cobalt supported on a suitable supporting material; -- the catalyst used for the hydrogenation of the at least one first intermediate (I1) according to b)in the presence of at least one primary and / or at least one secondary amine to at least one polyamine compound with at least one secondary and / or tertiary amino group preferably comprises one or more of copper, palladium, platinum and rhodium, wherein more preferably, the catalyst comprises palladium and optionally consists of palladium, wherein more preferably, the catalyst comprises, optionally consists of palladium supported on a suitable supporting material.

7. An intermediate (I1), obtainable or obtained by the process according to any one of claims 1 to 6.

8. An intermediate (I1), preferably the intermediate (I1) of claim 7, comprising at least one, preferably terminal, group CN, as defined in any one of claims 1 to 6.

9. A polyamine compound (II) or (III), obtainable or obtained by the process according to any one of claims 1 to6.

10. A polyamine compound (II) or (III), preferably the polyamine compound (II) or (III) of claim 9, comprising atleast one, preferably terminal, group NH, being at least one N-H functionality of at least one amino group ofthe polyamine of general formula (II) or (III) as defined in any one of claims 1 to 6.

11. Use of a polyamine compound (II) or (III) according to claim 9 or 10 which contains at least one primary orsecondary amine group, or use of a polyamine compound (II) or (III) according to claim 8 or 9 in or as co-reactant, hardener or curative for epoxy resins.

12. An epoxy resin composition, containing a polyamine compound (II) or (III) according to claim 9 or 10, whichcontains at least one primary or secondary amine group or containing a polyamine compound (II) or (III) according to claim 9 or 10, as a co-reactant, a hardener or a curative.

13. An epoxy resin composition, containing a polyamine compound (II) or (III) according to claim 9 or 10, whichcontains at least one primary or secondary amine group or a polyamine compound (II) or (III) according to claim 9 or 10, reacted as a co-reactant, a hardener or a curative with an epoxy resin.

14. Use of a polyamine compound (II) or (III) according to claim 9 or 10, or of compounds prepared therewith, forflotation; corrosion inhibition; asphalt emulsification; fertilizer-anticaking agents; additives for preventing caking of powdered minerals; emulsifiers, adjuvants, and intermediates in pesticide production; additives in plastic formulations; pigment-grinding aids; dispersants for pigments in paints, coatings, and magnetic tape; thickening agents in drilling muds, oil-based coatings and the paint industry; biocidal applications in households, swimming pools and oil fields; lubricants; petroleum additives; deicers for motor fuels; catalysis (such as in polyurethane formation); manufacturing of polyurethanes; intermediates for dyes, and of a polyamine compound (II) and / or polyamine compound (III) according to any one of claims 9 or 10 which contains tertiary amino groups as or for producing cleavable PU catalysts that can optionally be incorporated due to additional functional groups or upon cleavage.

15. A process, preferably according to any one of claims 1 to 6, comprising the step of converting a chemicalmaterial obtainable or obtained by the process according to any one of claims 1 to 6 to obtain a product Ω.

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