Use of compounds and method for electrochemical disintegration
A monomer-based electrochemical approach introduces bond cleavage in polymers using an electrical voltage, addressing inefficiencies in existing disintegration methods and enabling sustainable recycling by ensuring irreversible decomposition.
Patent Information
- Application Number
- PCT/EP2025/066771
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-06-21
- Filing Date
- 2025-06-16
- Publication Date
- 2025-12-26
AI Technical Summary
Existing methods for polymer disintegration, particularly in the context of recycling and sustainability, are inefficient and often rely on petroleum-based compounds, which are not environmentally sustainable.
The use of a monomer with a specific formula that, when incorporated into polymers, allows for bond cleavage through the application of an electrical voltage, enabling electrochemical disintegration and irreversible decomposition.
This method facilitates the selective disintegration and recycling of polymers by introducing predetermined breaking points, allowing for chemical recycling of plastics without repolymerization.
Smart Images

Figure EP2025066771_26122025_PF_FP_ABST
Abstract
Description
[0001]Düsseldorf, June 16, 2025 Our reference: RD 42789 / AL RWTH Aachen University, a public corporation, Templergraben 55, 52062 Aachen, Germany Use of compounds and processes for electrochemical disintegration The invention relates to the technical field of electrochemical disintegration of polymers. Polymers are usually developed with a view to their stability and, depending on the application, inert properties. For example, Chien-Kung Lin et al., “Synthesis and mesomorphism of thermotropic liquid crystalline polyurethanes based on meta-diisocyanates with 4,4′-bis(ω-hydroxyalkoxy) biphenyls”, European Polymer Journal 36 (2000) 1183-1193, describe thermotropic liquid crystalline polyurethanes (LCPUs). Mireia Buaki-Sogo et al.“Formation and Properties of a Hybrid Organosilica with a p-Phenylene Vinylene Polymer Partially Grafted to the Walls”, ChemPhysChem 2013, 14, 618-626, describe a hybrid organosilica. Noelia Fuentes et al., “On / off electrochemical switches based on quinone-bisketals”, Chem. Commun., 2011, 47, 1586-1588, describe the synthesis and anodic oxidation of a series of 2,5-diaryl- or dialkynylaryl-substituted 1,4-dialkoxybenzenes to quinone bisketals. EP 4186942 A1 describes polyesters and polycarbonates with a high refractive index and high transparency. CN 116730874 A describes an isocyanate monomer obtained by reacting a diol or diamine with diisocyanate, wherein the curing polymerization with the modified isocyanate monomer and oligomer diol is carried out in such a way as to improve the heat resistance and rheological processing properties of the polyurethane elastomer obtained.JP 2017193523 A describes a 9,10-bis-{2-(substituted aminocarbonyloxy)alkoxy}-anthracene compound. DE 3618006 A1 describes hydroxyphenylurethanes, processes for their preparation from polychloromethane esters and aminophenols, their use in the production of macromolecular substances and as antioxidants, as well as chloromethane esters containing nine hydroxyphenylurethane groups. DE 3618007 A1 describes a process for the preparation of hydroxyphenylurethanes. With regard to the increasing demands for sustainability, so-called "debonding" has received increased attention in recent years. Dharun Vadugappatty Srinivasan et al.The article “Review of debonding techniques in adhesively bonded composite structures for sustainability”, Sustainable Materials and Technologies 30 (2021) e00345, provides an overview of strategies, process steps and selection criteria for debonding composite connections as well as debonding technologies using mechanical, thermal, electrical, chemical and optical methods. Debonding technology enables, for example in the electronics industry, the separation of high-quality components or simplifies the recycling of electronic components or automotive parts.WO 2022 / 254268 A1, for example, describes an article comprising a first component with a first electrically conductive surface and a second component with a second surface, wherein an adhesive composition containing a cured polymerizable ionic liquid is positioned between the first electrically conductive surface and the second surface, bonding the components together. The effort required to separate the components is reduced by applying a direct current potential to the adhesive composition. WO 2019 / 103990 A1 describes an electrically releasable adhesive composition. The adhesive consists of a basic ionic liquid and an optionally cross-linked polymer. The adhesive composition can be configured to be selectively releasable under the influence of an electromotive force and can be positioned between a first and a second electrically conductive surface.Furthermore, WO 2023 / 228050 A1 describes a composite adhesive composition comprising a variety of polymeric nanoparticles dispersed in a (meth)acrylate-based matrix. An ionic liquid can be added to the composite adhesive to enable electrical release. EP 3199344 A1 describes the electrical release of polyurethane hot melt adhesives using conductive inks.WO 2021 / 259594 A1 describes a curable and electrochemically debondable adhesive composition comprising an ethylene-unsaturated nonionic monomer, a polymerizable ionic compound, and a radical initiator, as well as a bonded structure comprising two material layers with an electrically conductive surface, wherein the curable and electrochemically degradable adhesive composition is located between the material layers, and a method for debonding this bonded structure by applying a voltage to both surfaces. The debonding of electrochemically debondable adhesives is predominantly carried out using ionic liquids, the use of which can generally be considered sustainable, but whose synthesis involves petroleum-based compounds reacting with halogenated compounds.With regard to the increasing demand for the disintegration of everyday plastic materials, particularly packaging materials, the degradation and disintegration of polymers have gained in importance. The present invention therefore aimed to provide a disintegration agent that overcomes at least one of the aforementioned disadvantages of the prior art.This problem is solved by using a monomer according to formula (1) to generate a bond cleavage in a polymer obtained from at least the monomer, wherein the bond cleavage is induced by applying an electrical voltage across the polymer, according to claim 1, a method for the electrochemical disintegration of a polymer obtained from the monomer according to claim 2, a composite comprising at least one substrate and a polymer according to claim 6, a composition suitable for releasable bonding according to claim 7, a polymerizable monomer according to claim 8, and a polymer obtained from at least the polymerizable monomer according to claim 10.Provided is a use of a monomer according to formula (1) as specified below or its racemates, enantiomers, diastereomers or salts for generating a bond rupture in a polymer obtained from at least one monomer according to formula (1), wherein the bond rupture is induced by applying an electrical voltage across the polymer: wherein: E1, E2 is ZR3 or ZR4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2; Z ist O, S oder N; R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 -Heteroaryl, preferably pyridinyl, C4-C20-heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20- Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 - Heteroaryl, C4-C20-heterocycloalkenyl, C1-C30-alkoxy, CN, SCN, NC, NCO, NO2, halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R 3 , R 4 For Z, O or S is independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z, N is independently selected from the group comprising R'''2; R5, R6, R5a, R6a is independently selected from the group comprising H and / or C1-C6 alkyl, R' is independently selected from the group comprising H, C1-C30 alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10-Aryl;R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n, n ais an integer independently selected from 0, 1, 2, 3, 4, or 5. Surprisingly, it was found that a voltage-induced bond rupture can be brought about when an electrical voltage is applied across polymers obtained by incorporating a monomer of formula (1). Thus, polymers constructed using monomers of formula (1) can be electrochemically disintegrated. Without committing to a specific theory, it is assumed that the monomers allow the incorporation of predetermined breaking points into the polymer, such that applying an electrical voltage across the polymer induces a selective bond rupture in the polymerized monomer unit. This can cause degradation or disintegration of the polymer. This makes it possible to provide polymers that can be decomposed by applying a voltage.Thus, a selectively decomposable polymer and electrochemical disintegration of polymer products made from it can be provided, as well as electrical debonding of substrates bonded using this polymer. Within the scope of this invention, the terms "debonding" and "unbonding" are used synonymously. The monomer can therefore be used to produce (high-performance) polymers that have predetermined breaking points and thus enable end-of-life recycling. In other words, the monomers can be used as electrochemical switches for bond rupture in polymers. Such switches can be triggered as an end-of-life option in plastics and thus enable chemical / molecular recycling of (persistent) plastics. However, the resulting degradation products cannot be repolymerized, so the electrical debonding is irreversible. The term "C1-C" is used to describe this process. 30Unless otherwise specified, "-Alkyl" comprises straight-chain or branched alkyl groups with 1 to 30 carbon atoms. C1-C 10 -Alkyl groups, for example, selected from the group comprising methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, heptyl, isoheptyl, octyl, isooctyl, 2-ethylhexyl, neooctyl, nonyl and / or decyl. The term “C2-C 30 Unless otherwise specified, "-alkenyl" includes straight-chain or branched alkenyl groups with 2 to 30 carbon atoms. The term "C6-C20-aryl" refers to aromatic residues with 6 to 20 carbon atoms. Preferred aryl groups are selected from phenyl, naphthyl, indenyl, or biphenyl. The phenyl aryl group is particularly preferred. For the purposes of this invention, the term "phenylalkyl" includes the group consisting of alkyl-phenyl, where phenylalkyl includes, for example, phenylethyl and benzyl. The term "C3-C 30The term “-alkyl epoxide” in the context of the present invention refers to alkyl groups with a terminal epoxide group, wherein “C3” counts the carbon atoms of the entire group and includes the two carbon atoms of the epoxide group and at least one carbon atom of the alkyl group. The term “C5-C 20"Heteroaryl" in the context of the present invention refers to aromatic mono-, bi-, or tricyclic aryl groups comprising one or more, for example, 2, 3, 4, 5, or 6 heteroatoms selected from the group consisting of N, O, and S, wherein the heteroatoms partially replace the specified number of carbon atoms. In particular, one, two, three, or four heteroatoms selected from the group consisting of N, O, and S may be included. Heteroaryl residues may be selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl, triazolyl, pyridazinyl, 1,3,5-triazinyl, furyl, thienyl, and / or benzothienyl. Preferred heteroaryl residues are mononuclear heteroaryl residues with 4, 5, or 6 carbon atoms, preferably pyridinyl, in particular selected from 2-pyridinyl, 3-pyridinyl, and 4-pyridinyl. Within the scope of this invention, for the The term "pyridinyl" and the more common short form "pyridyl" are used synonymously for the substituent pyridine. The term "C4-C 20"Heterocycloalkenyl" in the context of the present invention refers to mono-, bi-, or tricyclic cycloalkenyl groups comprising one or more, for example, 2, 3, 4, 5, or 6 heteroatoms selected from the group consisting of N, O, and S, wherein the heteroatoms partially replace the specified number of carbon atoms. Preferred heterocycloalkenyl groups are mononuclear heterocycloalkenyl groups with 4, 5, or 6 carbon atoms, preferably imidazolyl, oxazolyl, oxazolidonyl, oxolanyl, oxolenyl, thiazolyl, thiazolidonyl, thiolanyl, and / or thiolenyl. The term "halogen" includes fluorine, chlorine, bromine, and iodine, with fluorine being preferred. The compounds described herein can have at least one stereocenter whose substituents cannot change their relative positions. This allows for various spatial arrangements. This is the case, for example, when a single carbon atom in a molecule bears four different substituents.This carbon atom is referred to as the stereocenter. Accordingly, racemates, enantiomers, and diastereomers of the compounds are included. Furthermore, the compounds, particularly those with charged or polar substituents, can exist in the form of their salts, for example, as sodium, potassium, or ammonium salts, chloride, bromide, iodide, sulfate, or nitrate salts. In embodiments of the monomer usable according to the invention, R1 and R2 are independently selected from the group comprising H, C6-C. 10 -Aryl, preferably phenyl, C5-C 10 - Heteroaryl preferably pyridinyl, C4-C 10 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C6-C 10 -Aryl, C5-C 10 -Heteroaryl, C4-C 20-Heterocycloalkenyl, or phenylethynyl, each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C10-alkyl, C1-C10-alkoxy, CN, SCN, NC, NCO, NO2, F,CF3, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – In embodiments of the monomer usable according to the invention, the substituents are nonpolar substituents selected from the group comprising C1-C 10 -Alkyl, C1-C 10 -Alkoxy, CN, SCN, NC, NCO, NO2, F and / or CF3. In other embodiments of the monomer usable according to the invention, the substituents are polar groups selected from [SR'2] + , [NR'3] + ,[PR'3]+ and / or SO3–. For the groups [SR'2]+, [NR'3]+, [PR'3]+, R' is preferably selected independently of each other from the group comprising hydrogen, C1-C 10 -Alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10-Aryl, in particular from hydrogen, methyl, ethyl or phenyl. In further embodiments of the monomer usable according to the invention, R 1 , R 2 independently selected from the group comprising hydrogen and C6-C10 aryl, preferably phenyl, wherein C6-C 10 -Aryl, in particular phenyl, is unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C3 alkyl, in particular methyl, C1-C3 alkoxy, in particular methoxy, CN and / or CF3. C6-C 10 -Aryl, in particular phenyl, can be unsubstituted or singly, doubly, or triply substituted, for example, singly in the para position, doubly in the para and meta positions or in both meta positions, or triply in the para and both ortho positions. In further embodiments of the monomer usable according to the invention, R 1 , R 2independently selected from the group comprising hydrogen, preferably unsubstituted C5-C10 heteroaryl, preferably pyridinyl, C4-C10 heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, in particular selected from hydrogen and phenylethynyl. In embodiments of the monomer usable according to the invention, E 1 , E 2 independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2. Where R'' is preferably selected from the group comprising C1-C10-alkyl, C3-C10-cycloalkyl, C6-C 10 -Aryl, C2-C 10 -Alkenyl, C3-C 10 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 10 -Alkyl. R''' is preferably selected independently of each other and is from the group comprising H, C1-C 30-Alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C10 alkyl, C3-C10 cycloalkyl, C6-C10 aryl, NCO and / or C1-C10 alkyl substituted with NCO. In embodiments of the monomer usable according to the invention, R 5 , R 6 , R 5a , R 6a independently selected from the group comprising H and / or C1-C6 alkyl, in particular hydrogen, methyl and ethyl. Preferably, R 5 and R 5a and / or R 6 and R 6a equal. Preferably R 5 , R 6 , R 5a and R 6a Hydrogen. The monomer usable according to the invention can be symmetrical or asymmetrical. The side chains on the two oxygen atoms can be the same or different. R 5 and R 5a , R 6 and R 6aThey can be the same or different. In particular, the two side chains can have different lengths, and n and n' can be different lengths. a may differ. Preferably, the monomer usable according to the invention is symmetrical and R5 and R5a, R6 and R6a, and n and na are identical. a are an integer independently selected from 0, 1, 2, 3, 4, or 5. In embodiments, n and n are a independently of each other 1, 2 or 3, in particular 1. Preferably n and na are equal. 1 , E 2 In preferred embodiments of the monomer usable according to the invention, a group ZR is 3 or ZR 4 Into this In the embodiments, the monomer usable according to the invention corresponds to the following formula (9): where Z is chosen from O, S or N and R 1 , R 2 , R 3 , R 4and n are defined as described above. It may be preferred that Z is nitrogen. Preferably, Z is oxygen. In preferred embodiments of the monomer usable according to the invention, the monomer has the following formula (10): wherein: R 1 , R 2 independently of one another is hydrogen, phenyl, pyridinyl or phenylethynyl, each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C30 alkyl, C3-C10 cycloalkyl, C6-C10 aryl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R 3 , R 4 R' is selected independently from the group comprising H, C(O)OR'', C(O)R'', C(O)NR''''2 and / or R''; R' is selected independently from the group comprising H, C1-C30-alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10-Aryl; R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n is an integer selected from 0, 1, 2, 3, 4 or 5. The R groups 3 , R 4 provide a derivatization of the monomer for application in various bond types. For the R residues 3 , R 4It is therefore preferred that these allow polymerization with various other monomers. R 3 , R 4 are independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R''. In embodiments of the monomer usable according to the invention, R 3 , R 4 Hydrogen. However, it may be preferred to protect the free alcohol groups, for example in the form of an ether or ester, or to provide, for example, a carbamate group. These are synthetically accessible, for example, by reacting the respective alcohol with alkylating agents, acids, or cyanates. The monomer usable according to the invention is preferably an alcohol, a urethane, ether, ester, carbamate, or amide. In embodiments of the monomer usable according to the invention, R 3 , R 4 selected from C(O)OR'', C(O)R'', C(O)NR'''2 and / or R''. Preferably, R'' is selected from the group comprising C1-C10 -Alkyl, especially methyl or ethyl, C3-C 10 -Cycloalkyl, C6-C 10 -Aryl, C2-C 10 -Alkenyl, C2-C10 alkyl epoxides and / or C1-C10 alkyl substituted with OH, NCO or COOH. Preferably, R'' is selected from the group comprising C1-C5 alkyl, -(CH2) q -OH with q is 1, 2, or 3, -(CH2) q -CH=CH2 with q is 1, 2, or 3, C3-C5 alkyl epoxide with terminal epoxide group, - (CH2) r -NCO with r is 1, 2, or 3. For the group R 3 , R 4 are C(O)R'' is R'' preferably -(CH2) s - COOH with s is 1, 2, or 3. In the case that groups R 3 , R 4 C(O)NR'''2sind, is R''' preferably selected from the group comprising H, C1-C 10 -Alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 10 -Alkyl, C3-C 10 -Cycloalkyl, C6-C 10-Aryl, NCO and / or C1-C substituted with NCO (isocyanate). 10 -Alkyl, in particular -(CH2)r-NCO with r is 1, 2, or 3. In embodiments of the monomer usable according to the invention, R 3 , R 4 Selected from hydrogen, methyl, ethyl, isopropyl, -(CH2)2-OH, C(O)CH3, C(O)C3H7, C(O)-HN-C2H5, or C(O)-HN-C4H9. Preferably, n is 1 or 2, particularly 1. In these embodiments, bond cleavage could be induced by applying an electrical voltage across polymers built from these monomers, yielding stable degradation products. For modifying the electrochemical properties, synthetic variations of group R have proven particularly suitable. 1 , R 2 proved to be decisive. R 1 , R 2The monomers usable according to the invention can be hydrogen or unsubstituted phenyl, pyridinyl, or phenylethynyl, independently of one another. It is advantageous that the properties can be modified by substitution, for example, in the case where R 1 , R 2 Phenyl are, are susceptible to influence. In particular, R 1 , R 2 The phenyl group may be singly or multiply, in particular doubly, substituted, preferably with substituents selected from C1-C3 alkyl, in particular methyl, C1-C3 alkoxy, in particular methoxy, CN, or CF3. The phenyl group may in particular be singly substituted at the para position, or doubly substituted at the para and meta positions, or at both meta positions, or triply substituted at the para and both ortho positions. Preferred groups R 1 , R 2 The monomers usable according to the invention are selected from hydrogen and the compounds according to the following formulas (14) to (20): The monomer usable according to the invention can have the following formulas (21) to (27) in embodiments: It may be preferable that R 3 , R 4 The monomer usable according to the invention is hydrogen. It may further be preferred to protect the free alcohol groups, for example in the form of an ether or ester, or to provide a carbamate group. The monomer usable according to the invention may, in embodiments, have the following formulas (28) to (31): wherein Ph is phenyl, unsubstituted or singly or multiply, in particular doubly, substituted with C1-C3 alkyl, in particular methyl, C1-C3 alkoxy, in particular methoxy, CN, or CF3. The monomers of formulas (29) to (31) are synthetically obtainable by reacting the monomer of formula (21) with methyl tosylate, isobutyric acid, or butyl isocyanate. The monomer usable according to the invention may, in embodiments, in particular have the following formulas (32) to (36): It has been found that polymers obtained from polymerization with a monomer according to formula (1) can be disintegrated by applying an electrical voltage across the polymer. A further aspect of the present invention relates accordingly to a method for the electrochemical disintegration of a polymer obtained from at least one of the monomers according to formula (1) or their racemates, enantiomers, diastereomers, or salts: in which: E 1 , E 2 is ZR3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2;Z is O, S or N;R1, R2 independently selected from the group comprising H, C1-C30-alkyl,C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 -Heteroaryl, preferably pyridinyl, C4-C 20 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 - Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 - Heteroaryl, C4-C 20 -Heterocycloalkenyl, C1-C 30-Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R 3 , R 4 for Z, O or S is independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z, N is independently selected from R'''2; R 5 , R 6 , R 5a , R 6a R' is selected independently from the group comprising H and / or C1-C6 alkyl; R'' is selected independently from the group comprising H, C1-C30 alkyl, C3-C10 cycloalkyl and / or C6-C10 aryl; R'' is selected independently from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30-Alkyl,R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n, n a is an integer independently selected from 0, 1, 2, 3, 4, or 5, where in step a) the polymer is provided and in step b) an electrical voltage is applied across the polymer, causing a bond rupture in the polymer. For the description of the groups E 1 , E 2 , Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 5a , R 6a , R', R'', R''', n and n aFor details, particularly regarding preferred embodiments, reference is made to the preceding description. Without committing to a specific theory, it is assumed that applying an electrical voltage across the polymer causes the hydroquinone core of the monomers to react to form a degradation product, for example, a ketal, or the corresponding benzoquinone, or a mixture of benzoquinone or ketal, and that the polymer bond is cleaved. Thus, the monomers allow for the incorporation of predetermined breaking points into a polymer, thereby inducing selective bond cleavage and thus causing degradation or disintegration of the polymer. Applying a voltage across the polymer leads to its decomposition or disintegration. The term "disintegration" of a plastic generally refers to the cleavage of the macromolecule.According to the described use of the monomers, this can be induced here by cleavage through selective bond rupture. By applying a voltage across the polymer, degradation products of the monomer are formed according to formula (1). For monomers with Z, the following degradation products were obtained: oxygen-symmetric or unsymmetric ketals of formulas (37) and / or (38) below, or quinones of formula (39) below, mixtures thereof, as well as compounds exhibiting both ketal and quinone characteristics, such as the compounds of formula (40) below. in which R 1 , R 2 , R 5 , R 6 , R 5a , R 6a , n and n aas defined above. The degradation products are not repolymerizable, so the reaction is electrochemically irreversible. The monomers according to formula (1) are polymerizable with each other or, preferably, with other monomers different from these, preferably selected from the group comprising polyols, acids, diisocyanates, acrylic acid, acrylates, methacrylates and / or formaldehyde, or mixtures thereof. Mixtures may include diisocyanates and at least two different diols. For example, copolymers of polyurethane with an incorporated switchable monomer and polyesters from conventional building blocks can be produced. In embodiments of the inventive use of the monomer or the process, the polymer comprises repeating units according to the following formulas (2) to (6) or their racemates, enantiomers, diastereomers or salts: in which: R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C30 alkenyl, C6-C20 aryl, preferably phenyl, C5-C20 heteroaryl, preferably pyridinyl, C4-C 20 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 - Heteroaryl, C4-C 20-Heterocycloalkenyl or phenylethynyl are each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C30-alkyl, C2-C30-alkenyl, C3-C10-cycloalkyl, C6-C20-aryl, C5-C20-heteroaryl, C4-C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ;X a polymerization partner obtained from at least one further monomer different from the monomer according to formula (1), preferably selected from the group comprising polyols, acids, diisocyanates, acrylic acid, acrylates, methacrylates and / or formaldehyde;Y is selected from the group comprising H, X and / or R''';R' independently selected from the group comprising H, C1-C30-alkyl,C3-C 10 -Cycloalkyl and / or C6-C 10-Aryl;R''' independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or C1-C substituted with NCO (isocyanate). 30-Alkyl; n is an integer selected from 0, 1, 2, 3, 4, or 5; m is an integer selected from 1, 2, 3, 4; o is an integer in the range of 2 to 200,000. For the description of groups E1, E2, Z, R1, R2, R3, R4, R5, R6, R', R'', R''', and n, in particular their preferred embodiments, reference is made to the preceding description. The repeating units of the polymer according to formulas (2) to (6) each comprise a polymerized unit of the monomer of formula (1) and a polymerization partner X obtained from at least one further monomer different from the monomer according to formula (1). The at least one further monomer is preferably selected from the group comprising polyols, acids, diisocyanates, acrylic acid, acrylates, methacrylates, and / or formaldehyde. X can, for example, be a hexanediol. In embodiments, o is an integer in the range of ≥ 2 to ≤ 100,000, preferably in the range of ≥ 2 to ≤ 1,000.In embodiments, m is an integer selected from 1, 2, 3, or 4. It may be preferred that the polymerized unit of the monomer of formula (1) is present in the polymer in a smaller proportion and that m is 2, 3, or 4. For the repeating units of the polymer formed from Z, which is nitrogen, according to formulas (3) and (6), the possibilities arise that the nitrogen, as a substituent Y, binds a hydrogen molecule or a residue R''', or binds a further polymerization partner X from a further monomer different from the monomer according to formula (1). Preferably, the polymer may contain repeating units based on Z, which is oxygen, according to formulas (2) or (5). In embodiments, the polymer is a polyurethane, a polyester, a polyether, or a polyamide. In embodiments, the polymer is a polyurethane comprising repeating units according to the following formula (7): wherein p is an integer in the range of 2 to 200,000. In embodiments, p is an integer in the range of ≥ 2 to ≤ 100,000, preferably in the range of ≥ 2 to ≤ 1,000. The polymerization of a polyol according to formula (1) with polyisocyanates yielded polyurethanes that exhibited adhesive properties and, surprisingly, are suitable for bonding or as adhesives. The polyurethanes proved suitable for bonding various surfaces such as metal or plastic, particularly aluminum. In particular, it was shown that the monomer building blocks, acting as "electrochemical switches," enable bond rupture of the polymer and thus allow the bonded surfaces to be separated or "debonded." The polymerization of a monomer according to formula (1) with other monomers is suitable for producing polymers that are suitable, for example, as thermoplastic materials or for the production of molded parts.Polymers obtained from at least one monomer according to formula (1) are thus also suitable for the production of plastic products. In plastic products, the monomer building blocks can also act as "electrochemical switches," enabling bond rupture of the polymer and thus facilitating disintegration and the degradation or recycling of (persistent) plastics. Processes for the electrochemical disintegration of a polymer obtained from monomers according to formula (1) can therefore be designed for various applications. In embodiments, in step a), a mixture comprising the polymer, or a product made from the polymer, a solvent, and optionally a salt is provided, and in step b), the mixture from step a) is electrolyzed in an electrochemical cell comprising an anode and a cathode, which are in electrical connection with the mixture.Electrolysis induces bond cleavage in the monomer building block to form one or more polymer degradation products. These embodiments are suitable for applications in the chemical recycling of polymer products. According to the described process, the mixture is electrolyzed in an electrochemical cell comprising an anode and a cathode, which are electrically connected to the mixture, to form one or more polymer degradation products. For the purposes of this application, the term "electrochemical cell" refers to arrangements used in electrochemistry or based on electrochemical processes. Electrolysis cells are used to obtain various substances by applying a voltage. Electrolytic reduction takes place at the cathode, while electrolytic oxidation occurs at the anode.In particular, the degradation products of the polymer are formed by anodic oxidation. For monomers with oxygen Z, the degradation products can be symmetrical or unsymmetrical ketals of formulas (37), (38) or quinones of formula (39), mixtures thereof, as well as compounds exhibiting both ketal and quinone characteristics, such as the compounds of formula (40). The electrolyzable mixture can be a suspension of the polymer in a solvent. Depending on the polymer, the solvent can comprise organic solvents, preferably alcohols, water, or mixtures thereof. The term "alcohol" here includes monohydric and polyhydric alcohols. Preferably, the alcohol is selected from the group consisting of methanol, ethanol, propanol, and / or isopropanol. Alcoholic, in particular methanolic, solutions can be used. The mixture comprises a polymer or...The polymer product and solvent preferably contain one or more salts that facilitate charge transport in the electrolyte. In principle, all salts soluble in solvents are suitable. Examples of suitable salts include hydroxides and halides, particularly alkali metal halides such as NaCl or KCl, alkali metal hydroxides such as NaOH, KOH, or LiOH, or mixtures thereof. Hydroxides and halides are soluble in alcohol, water, and mixtures thereof. For example, solutions of potassium hydroxide in methanol or ethanol can be used. The concentration of the salt or hydroxide can range from ≥0.1 M to ≤1 M. Other electrolysis parameters, such as electrode material, current, temperature, or pressure, are adjustable. For example, platinum can be used as the anode material and / or graphite as the cathode material. The current density of the electrolysis can be in the range of ≥1 mA / cm². 2 up to ≤ 100 mA / cm 2 , preferably in the range of ≥ 10 mA / cm2 up to ≤ 30 mA / cm 2The electrical voltage can vary for different applications and, for example, range from 0.1 V to 250 V and / or be applied for a period of time ranging from 1 s to 30 min. Electrolysis can be carried out at normal pressure and, if necessary, at elevated temperatures, which can improve the energy balance of the electrochemical degradation. In other embodiments, the electrochemical disintegration method can be used for the (re)dissolving of paints and coatings based on polymers obtained from monomers according to formula (1). In such embodiments, in step a) the polymer is applied to a substrate, and in step b) a voltage is applied to the substrate and / or across the polymer. Applying the voltage induces bond cleavage in the monomer building block to form one or more degradation products of the polymer.The substrate can optionally have an electrically conductive surface or be an electrically conductive substrate itself. A substrate can be made of, for example, metal, plastic, or a composite material. In further embodiments, the electrochemical disintegration method can be used for applications in the field of debonding adhesive polymers or adhesives.In such embodiments, in step a) a composite is prepared, comprising at least two joining parts and the polymer, wherein the polymer is applied between at least one surface of each joining part, the polymer or one of the further layers forming an adhesive bond between the surfaces of the joining parts, and wherein the joining parts optionally have an electrically conductive surface or are electrically conductive, and in step b) a voltage is applied to the joining parts and / or across the polymer to break the composite. Applying the electrical voltage across the polymer induces bond rupture in the monomer unit to form one or more degradation products of the polymer. In embodiments, the electrochemical disintegration method is thus a method for irreversible disassembly. The joining parts can be made, for example, of metal, plastic, or a composite material.The electrochemically cleavable monomer unit in the polymer allows the substrates to be debonded or irreversibly unbonded by applying an electrical voltage. The adhesive bond based on polymers containing an electrochemically cleavable monomer unit enables targeted debonding of the polymer between the components. This allows, for example, the recovery of individual components, especially metals, from bonded objects. The components themselves can already be electrically conductive, such as metal parts, or optionally have an electrically conductive surface that allows a voltage to be applied across the polymer. Optionally, one or more additional layers can be applied between the surfaces of the components. One or more of these additional layers can be an adhesive layer. Such an arrangement would also allow for one-sided debonding.The electrical voltage can also vary in these embodiments for different applications and, for example, be in the range of 0.1 V to 250 V, or in the range of 5 V to 100 V, and / or be applied for a period of time in the range of 1 s to 30 min. It was found that two aluminum substrates, between which a polyurethane comprising repeating units according to formula (7) had been applied, could be separated from each other in less than 30 seconds when a voltage of 5 V was applied. Another aspect concerns a composite comprising at least one substrate, in particular two joining elements, and a polymer obtained from at least the monomer according to formula (1) or its racemates, enantiomers, diastereomers, or salts, as specified below: wherein: E. 1 , E 2 is ZR 3 or ZR 4or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2;Z is O, S or N;R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 -Heteroaryl, preferably pyridinyl, C4-C 20 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 - Heteroaryl, C4-C20-heterocycloalkenyl or phenylethynyl are each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 - Heteroaryl, C4-C 20 -Heterocycloalkenyl, C1-C 30-Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ;R3, R4 for Z is O or S independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z is N independently selected from R'''2; R 5 , R 6 , R 5a , R 6a selected independently from the group comprising H and / or C1-C6 alkyl,R' selected independently from the group comprising H, C1-C30 alkyl,C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl;R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30-Alkyl,R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C 1-C30-Alkyl; n, n ais an integer independently selected from 0, 1, 2, 3, 4, or 5, wherein the bond is preferably a bond that can be dissolved by applying an electrical voltage. For the description of groups E1, E2, Z, R1, R2, R3, R4, R5, R6, R5a, R6a, R', R'', R''', n, and na, as well as the description of the substrate and the joining elements, in particular their preferred embodiments, reference is made to the preceding description. A further aspect relates to a composition suitable for dissolvable bonding, comprising a polymerizable monomer according to formula (1) as specified below or its racemates, enantiomers, diastereomers, or salts, and / or a polymerizable prepolymer obtained from at least the monomer according to formula (1) specified below or its racemates, enantiomers, diastereomers, or salts, and optionally an electrically conductive additive: w orin: E 1 , E 2 is ZR 3 or ZR 4or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2; Z ist O, S oder N; R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C30 alkenyl, C6-C20 aryl, preferably phenyl, C5-C20 heteroaryl, preferably pyridinyl, C4-C 20 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 - Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C30-alkyl, C2-C30-alkenyl, C3-C10-cycloalkyl, C6-C20-aryl, C5-C20-heteroaryl, C4-C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] +and / or SO3 – ; R 3 , R 4 for Z, O or S is independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z, N is independently selected from R'''2;R 5 , R 6 , R 5a , R 6a R' is selected independently from the group comprising H and / or C1-C6 alkyl, R' is selected independently from the group comprising H, C1-C30 alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl; R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30-Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n, n ais an integer independently selected from 0, 1, 2, 3, 4, or 5. For the description of groups E1, E2, Z, R1, R2, R3, R4, R5, R6, R5a, R6a, R', R'', R''', n, and na, in particular their preferred embodiments, reference is made to the preceding description. The composition may, in particular, be a curing or crosslinking composition. The composition may contain polymerizable monomers according to formula (1). In other embodiments, the composition may contain polymerizable prepolymers obtained from at least the monomer according to formula (1). A prepolymer is understood to be a reactive oligomer that is still polymerizable and can thus react with further monomers or prepolymers to form a polymer. The composition suitable for releasable bonding may contain an electrically conductive additive.The additive remains in the fully polymerized composition during hardening or polymerization and can improve the electrical conductivity across the polymer. This can contribute to more electrochemically cleavable monomer units in the polymer being accessible to induced bond cleavage, and debonding can be carried out more homogeneously, faster, or at a lower voltage. Examples of electrically conductive additives include organic or inorganic salts, carbon black, carbon nanotubes, or ionic liquids. Another subject matter is a polymerizable monomer, wherein the polymerizable monomer is a monomer according to formula (1) as specified below, or its racemates, enantiomers, diastereomers, or salts. in which: E 1 , E 2 is ZR 3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2; Zist O, S oder N; R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 -Heteroaryl, preferably pyridinyl, C4-C 20 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, preferably phenyl, C5-C 20 - Heteroaryl, C4-C20-heterocycloalkenyl or phenylethynyl are each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 - Heteroaryl, C4-C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, especially F, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 –;R3, R4 for Z is O or S independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z is N independently selected from R'''2; R 5 , R 6 , R 5a , R 6a selected independently from the group comprising H and / or C1-C6 alkyl,R' selected independently from the group comprising H, C1-C30 alkyl,C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl;R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl,R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30-Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl;n, na is an integer independently selected from 0, 1, 2, 3, 4 or 5, where: a) for Z is O, n is 0 and R 3 and R 4 are H, R 1 and R 2 are not simultaneously unsubstituted phenyl, b) for Z is O, n is 1 and R 3 and R 4 are H, R 1 and R 2 not simultaneously H, CH2Cl, unsubstituted phenyl or phenylethynyl, or phenyl substituted with C10-aryl, or c) for Z is O, n is 1 and R 1 and R 2 are H, R 3 and R 4 not simultaneously C(O)NR'''2 with R''' are H or a group selected from (12) or (13) are. In embodiments of the monomer, R 1 , R 2 Selected independently from the group comprising C6-C 10 -Aryl, preferably phenyl, C5-C10 -Heteroaryl, preferably pyridinyl, C4-C 10 - Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl, each singly or multiply substituted with substituents selected from the group comprising C1-C 10 -Alkyl, C1-C 10 -Alkoxy, CN, SCN, NC, NCO, NO2, F, CF3, [SR'2]+, [NR'3]+, [PR'3]+ and / or SO3–. In embodiments of the monomer, the substituents are nonpolar substituents selected from the group comprising C1-C 10 -Alkyl, C1-C 10 -Alkoxy, CN, SCN, NC, NCO, NO2, F, or CF3. In other embodiments of the monomer, the substituents are polar groups selected from [SR'2]+, [NR'3]+, [PR'3]+, and / or SO3–. For the groups [SR'2]+, [NR'3]+, [PR'3]+, R' is preferably selected independently of each other from the group comprising hydrogen, C1-C 10 -Alkyl, C3-C 10 - Cycloalkyl and / or C6-C 10-Aryl, in particular from hydrogen, methyl, ethyl or phenyl. In further embodiments of the monomer, R 1 , R 2 independently of each other C6-C 10 -Aryl, preferably phenyl, singly or multiply substituted with substituents selected from the group comprising C1-C3 alkyl, in particular methyl, C1-C3 alkoxy, in particular methoxy, CN and / or CF3. C6-C 10 -Aryl, especially phenyl, can be unsubstituted or singly, doubly, or triply substituted, for example, singly in the para position, doubly in the para and meta positions or in both meta positions, or triply in the para and both ortho positions. In further embodiments of the monomer, R1 and R2 are independently selected from the group comprising unsubstituted C5-C 10 -Heteroaryl, preferably pyridinyl, C4-C 10 -Heterocycloalkenyl, preferably imidazolyl, or phenylethynyl. In embodiments of the monomer, E 1 , E2 independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2. Here, R'' is preferably selected from the group comprising C1-C 10 -Alkyl, C3-C 10 -Cycloalkyl, C6-C 10 -Aryl, C2-C 10 -Alkenyl, C3-C 10 - Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 10 -Alkyl. R''' is preferably selected independently of each other and is from the group comprising H, C1-C 30 -Alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C10 alkyl, C3-C10 cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 10 -Alkyl. In embodiments of the monomer, R 5 , R 6 , R 5a , R 6aindependently selected from the group comprising H and / or C1-C6 alkyl, in particular hydrogen, methyl and ethyl. Preferably, R 5 and R 5a and / or R 6 and R 6a equal. Preferably R 5 , R 6 , R 5a and R 6a Hydrogen. The monomer can be symmetrical or asymmetrical. The side chains on the two oxygen atoms can be the same or different. R 5 and R 5a , R 6 and R 6a They can be the same or different. In particular, the two side chains can have different lengths, and n and n' can be different lengths. a They may be different. Preferably, the monomer is symmetrical and R 5 and R5a, R6 and R6a, and n and na are equal. a are an integer independently selected from 0, 1, 2, 3, 4, or 5. In embodiments, n and n are aindependently of each other 1, 2 or 3, in particular 1. Preferably n and n a same. E 1 , E 2 In preferred embodiments of the monomer, a group ZR 3 or ZR 4 In these embodiments, the monomer corresponds to formula (9) wherein Z is selected from O, S or N and R 1 , R 2 , R 3 , R 4 and n are defined as described for the monomer. It may be preferred that Z is nitrogen. Preferably, Z is oxygen. In preferred embodiments, the monomer has the following formula (10): in which: R 1 , R 2 independently of one another phenyl, pyridinyl or phenylethynyl, each singly or multiply substituted with substituents selected from the group comprising C1-C30 alkyl, C3-C 10 -Cycloalkyl, C6-C 10 -Aryl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3]+ and / or SO3 – , or unsubstituted pyridinyl; R 3 , R 4 R' is selected independently from the group comprising H, C(O)OR'', C(O)R'', C(O)NR''''2 and / or R''; R' is selected independently from the group comprising H, C1-C30-alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl; R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30-Alkyl; n is an integer selected from 0, 1, 2, 3, 4 or 5. In embodiments of the monomer, R 3 , R 4 Hydrogen. However, it may be preferred to protect the free alcohol groups, for example in the form of an ether or ester, or to provide, for example, a carbamate group. The monomer is preferably an alcohol, a urethane, ether, ester, carbamate, or amide. In further embodiments of the monomer, R 3 , R 4 selected from C(O)OR'', C(O)R'', C(O)NR'''2 and / or R''. Preferably, R'' is selected from the group comprising C1-C 10 - Alkyl, especially methyl or ethyl, C3-C 10 -Cycloalkyl, C6-C 10 -Aryl, C2-C 10 -Alkenyl, C2-C 10 -Alkyl epoxides and / or C1-C10 alkyl substituted with OH, NCO or COOH. Preferably, R'' is selected from the group comprising C1-C5 alkyl, -(CH2) q -OH with q is 1, 2, or 3, -(CH2) q- CH=CH2 with q is 1, 2, or 3, C3-C5 alkyl epoxide with terminal epoxide group, -(CH2) r -NCO with r is 1, 2, or 3. For the group R 3 , R 4 are C(O)R'' is R'' preferably -(CH2) s -COOH with s is 1, 2, or 3. In the case that group R 3 , R 4 C(O)NR'''2sind, is R''' preferably selected from the group comprising H, C1-C 10 -Alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 10 -Alkyl, C3-C 10 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or C1-C substituted with NCO (isocyanate). 10 - Alkyl, in particular -(CH2) r-NCO with r is 1, 2, or 3. In embodiments, R3, R4 are selected from hydrogen, methyl, ethyl, isopropyl, -(CH2)2-OH, C(O)CH3, C(O)C3H7, C(O)-HN-C2H5, or C(O)-HN-C4H9. Preferably, n is equal to 1 or 2, in particular 1. R1, R2 can be pyridinyl or phenylethynyl independently of each other. In particular, R1, R2 can be 2 The phenyl group may be singly or multiply, in particular doubly substituted, preferably with substituents selected from C1-C3 alkyl, in particular methyl, C1-C3 alkoxy, in particular methoxy, CN, or CF3. The phenyl group may in particular be singly substituted in the para position, or doubly substituted in the para and meta positions, or in both meta positions, or triple substituted in the para and both ortho positions. Preferred groups R 1 , R 2The monomers are selected from the groups according to formulas (14), (15), (17), (18), (19) and (20). The monomer may, in embodiments, have formulas (23) to (27). It may be preferred that R 3 , R 4Hydrogen. It may further be preferred to protect the free alcohol groups, for example, in the form of an ether or ester, or to provide a carbamate group. In embodiments, the monomer may have formulas (28) to (31), wherein Ph is phenyl, singly or multiply, in particular doubly, substituted with C1-C3 alkyl, in particular methyl, C1-C3 alkoxy, in particular methoxy, CN, or CF3. Another object is a polymer obtained from at least the polymerizable monomer as described above and preferably at least one further monomer different therefrom selected from the group comprising polyols, acids, diisocyanates, acrylic acid, acrylates, methacrylates, and / or formaldehyde. Unless otherwise stated, the technical and scientific terms used have the meanings commonly understood by a person skilled in the art in the field to which this invention belongs.Examples and figures illustrating the present invention are given below. Figure 1 shows cyclic voltagrams of the monomers of formulas (22), (32), (33), (35), (36), (21), (23), (24), (27), (26), and (25) in Figures 1A to 1K. Figure 2 shows the current flow applied to a voltage of 5 V across two aluminum plates bonded with an oligomer according to Example 2.1. Chemicals: The examples were carried out using commercially available chemicals without further purification. The apparatus used was stored in a drying oven at 100 °C and, unless otherwise specified, was baked out three times under high vacuum and purged with argon (Argon 4.8, Air Products GmbH) before the syntheses. The syntheses were carried out in accordance with general Schlenk techniques.Solvents of analytical purity were used and, to ensure working under the exclusion of oxygen and moisture, were degassed before use and stored over a molecular sieve. Magnetic stirrers were used for the syntheses and catalysis. Example 1: Synthesis of monomers according to formula (1). 1.1 Synthesis of 2,5-Diphenyl-1,4-hydroxyquinone The synthesis was carried out in air. 2,5-Diphenyl-1,4-benzoquinone (10.00 g, 38.4 mmol, 1.00 eq) was placed together with zinc powder (10.00 g, 153.0 mmol, 4.0 eq) and zinc chloride (10.00 g, 73.4 mmol, 1.9 eq) and dissolved in ethanol (200 mL). The suspension was refluxed for 4 h and then filtered. The filtrate was then concentrated to approximately 50 mL and poured into demineralized water (200 mL). The precipitated product was filtered off, dissolved in acetone, and dried over potassium carbonate. The solvent was removed under reduced pressure, and the product was recrystallized in dichloromethane. 2,5-Diphenyl-1,4-hydroxyquinone was obtained as a white solid. 1.2 Synthesis of 1,4-diethoxy-2,5-diphenyl-1,4-hydroquinone according to formula (22) 2,5-Diphenyl-1,4-hydroxyquinone obtained from Example 1.1 (500 mg, 1.91 mmol, 1.00 eq) was reacted with ethylene carbonate (369 mg, 4.19 mmol, 2.2 eq) and tetrabutylammonium fluoride trihydrate (TBAF ∙ 3 H₂O, 6.1 mg, 0.019 mmol, 1 mol%) in N,N-dimethylacetamide (DMAc, 2 mL) and stirred at 150 °C for at least 16 h. The solution was then poured into water, the precipitated product was filtered off, dissolved in acetone, and dried over potassium carbonate. The solvent was removed under reduced pressure, the product was reconstituted in a small amount of dichloromethane (DCM), and the product was purified by column chromatography (eluent ratio: ethyl acetate:pentane 1:1). The product was obtained as a white solid. 1,4-Diethoxy-2,5-diphenyl-1,4-hydroquinone according to formula (22) obtained from Example 1.2 (100 mg, 0.29 mmol, 1.00 eq), sodium hydride suspension (NaH, 60% in paraffin oil, 45.6 mg, 1.14 mmol, 4.0 eq), and para-toluenesulfonic acid methyl ester (121 mg, 0.65 mmol, 2.3 eq) were placed in N,N-dimethylformamide (DMF, 10 mL) and stirred for 20 h. The suspension was then diluted with ethyl acetate (40 mL) and washed three times with aqueous hydrochloric acid (10%, 5 mL). The organic phases were finally dried over magnesium sulfate (MgSO4), and the solvent was removed under reduced pressure. The product was obtained as a slightly yellowish solid. 1.4 Synthesis of O,O'-(2-Hydroxyethyisobutyra tyl)-2,5-diphenyl-1,4-hydroquinone according to formula (33) 1,4-Diethoxy-2,5-diphenyl-1,4-hydroquinone according to form (22) obtained from Example 1.2 (100 mg, 0.29 mmol, 1.00 eq), para-toluenesulfonic acid (pTSA, a saturate), and isobutyric acid (0.12 mL, 114 mg, 1.3 mmol, 2.5 eq) were reacted with sodium sulfate (Na₂SO₄, 5 g) in toluene and refluxed for 10 h. After completion of the reaction, the solution was filtered and the organic phase was washed three times with deionized water. The organic phase was then dried over MgSO₄ and the solvent was removed under reduced pressure. The product was obtained as a slightly yellowish solid. erhalten. 1.5 Synthesis of O,O'-(2-Hydroxyethylphenylurea) etanyl)-2,5-diphenyl-1,4-hydroquinone according to formula 1,4-Diethoxy-2,5-diphenyl-1,4-hydroquinone according to formula (22) obtained from Example 1.2 (160 mg, 0.46 mmol, 1.00 eq) was placed in DMAc (1 mL) and phenyl isocyanate (0.11 mL, 1.02 mmol, 2.2 eq) was added. The solution was stirred for 2 h at 50 °C and the reaction progress was then monitored by thin-layer chromatography. After complete conversion, the reaction solution was poured into a mixture of deionized water and methanol (5 mL : 5 mL) and the precipitated product was filtered off. The product was dissolved in DCM, dried over MgSO4, and the solvent was removed under reduced pressure. The product was obtained as a colorless solid. 1.6 Synthesis of O,O'-(2-Hydroxyethylbutyluret anyl)-2,5-diphenyl-1,4-hydroquinone according to formula (35) 1,4-Diethoxy-2,5-diphenyl-1,4-hydroquinone according to formula (22) obtained from Example 1.2 (100 mg, 0.46 mmol, 1.00 eq) was reacted with triethylamine (0.15 mL, 110 mg, 1.1 mmol, 3.8 eq) in DMAc (1.5 mL) and butyl isocyanate (0.1 mL, 0.90 mmol, 3.1 eq) was added. The solution was stirred at 50 °C and the reaction progress was monitored by thin-layer chromatography. After 5 h, the reaction was stopped, the reaction mixture was added to methanol (10 mL), and the product was precipitated with deionized water (10 mL). The product was then washed with methanol, dissolved in ethyl acetate, dried over MgSO4, and the solvent was removed under reduced pressure. The product was obtained as a colorless solid. 1.7 Synthesis of O-(2-ethanoylethoxy)O'-(ethoxy)-2,5-diphenyl-1,4-hydroquinone according to formula (36) 2,5-Diphenyl-1,4-hydroxyquinone obtained from Example 1.1 (1.387 g, 5.28 mmol, 1.00 eq) was reacted with ethylene carbonate (1.630 g, 18.5 mmol, 3.5 eq) and TBAF × 3 H₂O (12 mg, 0.038 mmol, 0.7 mol%) in DMAc (4 mL) and stirred for 16 h at 150 °C. The solution was then purified by column chromatography (mixing ratio: pentane:ethyl acetate 1:2). The solvent was removed from the product fraction under reduced pressure, the product was dissolved in acetone, and precipitated with water. Finally, the precipitated product was filtered off, dried over MgSO₄ in ethyl acetate solution, and the solvent was removed under reduced pressure. The product was obtained as a colorless solid. 1.8 Synthesis of 2,5-diaryl-1,4-hyroquinones ($9ab) R = 3,4-Methoxyphenyl, Xylyl, 4-Nitrilephenyl, 4-Methoxyphenyl, 4-Trifluoromethylphenyl. The syntheses of the diarylhydroquinones were carried out via a Suzuki reaction. The starting material weights for this reaction are given for the synthesis of the xylyl derivative; for the subsequent syntheses, the corresponding starting material weight was adjusted to 1.00 eq. 2,5-Dibromohydroquinone (1.00 g, 3.73 mmol, 1.00 eq) was reacted with the corresponding arylboronic acid (7.65 mmol, 2.05 eq) in THF (30 mL) and stirred for 30 min at 80 °C. Subsequently, an aqueous K₂CO₃ solution (1.12 M, 10 mL, 3 eq) was added dropwise to the reaction solution over one minute, and bis(tri-tert-butylphosphine)palladium was added. The reaction solution was stirred for one hour at 70 °C and then transferred to a separatory funnel. The aqueous phase was removed, ethyl acetate (100 mL) was added to the organic phase, and the organic fraction was washed twice with water.The organic phase was then dried over magnesium sulfate, and the solvent was removed under reduced pressure. For further purification, the product was further purified by column chromatography and recrystallized in dichloromethane. Simple filtration proved to be a sufficient purification method for these products. Table 1: 2,5-Diaryl-1,4-hydroxyquinone Compound R Arylboronic Acid Compound No. $. 9a Xylyl $9b 3,4-Dimethoxyphenyl$9c 4-nitrilephenyl$9d 4-Methoxyphenyl $9e 4- Trifluoromethylphenyl 1.9 Synthesis of 2,5-diaryl-1,4-hyroquinones according to formulas (23) to (27) R = 3,4-Methoxyphenyl, Xylyl, 4-Nitrilphenyl, 4-Meth 4-Trifluoromethylphenyl The corresponding hydroquinone of formula $9 ae (1.00 eq) was reacted with ethylene carbonate (264.4 mg, 3.00 mmol, 2.2 eq) and tetrabutylammonium fluoride trihydrate (TBAF ∙ 3 H₂O, 4.3 mg, 0.014 mmol, 1 mol%) in DMAc (1 mL) and stirred for at least 16 h at 150 °C. The product was then purified by column chromatography. The starting materials and batch sizes are given in Table 2. The prepared 2,5-diaryl-1,4-hydroquinones of formulas (23) to (27) are summarized in Table 3. Table 2: Initial weights for the syntheses of the 2,5-diaryl-1,4-hyroquinones of formulas (23) to (27) Compound R Initial weight hydroquinone Initial weight hydroquinone Formula 9 ae [mg] 9 ae [mmol] (23) Xylyl 43 4.6 1.36 (24) 3,4-Dimethoxyphenyl 27 5.0 0.71 (27) 4-Nitrilephenyl 50 1.60 (26) 4-Methoxyphenyl 25 0 0.78 (25) 4-Trifluoromethylphenyl 25 8 3.73 Table 3: 2,5-Diaryl-1,4-hyroquinones according to formulas (23) to (27) Compound No.R Compound(23) Xylyl(24) 3,4-Dimethoxyphenyl(27) 4-Nitrilephenyl(26) 4-Methoxyphenyl(25) 4-TrifluoromethylphenylExample 2 Synthesis of polyurethanes 2.1 Synthesis of polyurethanes with meta-tetramethylxylylene diisocyanate. To synthesize the oligomeric polyurethane diols, 1,4-hyroxyethoxybenzene (5.00 g, 1.0 eq) was dissolved in acetone under reflux (100 mL). Subsequently, meta-tetramethylxylylene diisocyanate (0.67–0.92 eq, 3.9–5.4 mL) and dibutyltin dilaurate (DBTL, 0.1 mL) were added, and the reaction solution was refluxed for 1.5 h. The solution was then concentrated under reduced pressure. The desired molar mass of the oligomers was adjusted in the reactions via the diol-to-diisocyanate ratio; molar masses of 1100 g / mol were obtained for three polymerizations. -1 , 3300 g∙mol -1 and 5500 g∙mol -1 The goal was to achieve a successful synthesis. End-group analysis using NMR confirmed the synthesis. 2.2 Synthesis of Copolymers The synthesis of ethane was based on a method by W. Zhou, et al. (ChemSusChem 2021, 14, 4176). Copolymers with one mol% or five mol% switchable diol in the total amount of diol (switchable diol and hexanediol) were synthesized, where m = 0.95 and n = 0.05 and m = 0.99 and n = 0.01, respectively. The synthesis of the polyurethane with five mol% switchable diol is described below. Initially, diphenylmethane-4,4'-diisocyanate (MDI; 1.337 g; 5.344 mmol; 1 eq) and 1,4-diethoxy-2,5-diphenyl-1,4-hydroquinone according to formula (22) (93.7 mg; 0.267 mmol; 0.05 eq) were placed in dimethylacetamide (DMAc, 5.4 ml) according to formula (22). Subsequently, 1,6-hexanediol (600 mg; 5.075 mmol; 0.95 eq) in DMac (2 ml) was slowly added dropwise to the solution. The solution was then stirred for 2 h at room temperature and for a further 2 h at 60 °C. The product was precipitated in water, filtered, and then washed with water and diethyl ether. The product was obtained as a white solid.The synthesis of the polymer with one mol% switchable diol was carried out analogously. Example 3: Cyclovoltammetry of the monomers. A three-electrode setup was used to characterize the monomers by cyclic voltammetry. A standard scan rate of 100 mV∙s was used. -1A platinum electrode tip (round, 1 mm diameter) was selected as the working electrode, and a platinum wire as the counter electrode. An Ag / AgNO3 solution with an AgNO3 concentration of 0.01 mol / L in MeCN and a 0.1 mol / L TBAPF6 conducting salt were used as the reference electrode. Ferrocene was added to the solutions after the measurement was completed as an internal reference, and the measurement was referenced to the ferrocene / ferrocenyl redox couple. Measurements of 18 µmol of each monomer were carried out in 6 mL of acetonitrile (MeCN) with 0.2 mol / L of tetrabutylammonium hexafluorophosphate (TBAPF6) as the conducting salt. The cyclic voltagrams of the individual monomers, formulas (22), (32), (33), (35), (36), (21), (23), (24), (27), (26), and (25), are shown in Figures 1A to 1K. As can be seen in Figures 1A to 1K, the cyclic voltagrams of the individual monomers showed only slight shifts of the maxima towards higher voltages.The irreversibility of the reaction is evident from the irreversible peak at 1.45 to 1.6 V. Furthermore, it is assumed that electron-withdrawing substituents require a higher voltage to form the degradation products. Example 4: Electrolyses of the monomers of formulas (22) and (35). A two-electrode setup was used for the electrolyses of the monomers of formulas (22) and (35). Based on a setup described by Fuentes et al. (Chem. Commun., 2011, 47, 1586-1588), a platinum mesh (50 x 50 mm, 745 mesh size) was used as the anode and a graphite rod (10 x 50 mm) as the cathode. The electrolyte solution was a methanolic potassium hydroxide solution (1 wt%). Under these conditions, constant-current electrolyses up to approximately 50 mA and a cutoff voltage of 3.5 V were performed at room temperature (20±2°C).For the electrolysis of formula (22), 80 mL of a 7.8 millimolar solution was used, while for the electrolysis of the monomer of formula (35), 40 mL of a 2.3 millimolar solution was used. The degradation products were determined by NMR. It was found that the electrolysis of the monomer of formula (22) yielded a mixture of the following degradation products: The quinone shown below was obtained by electrolysis of the monomer of formula (35): Example 5 Bonding using the oligomers and debonding: The reaction mixtures of the oligomers with molar masses of 1100 g∙mol obtained from Example 2.1 1 , 3300 g∙mol -1 and 5500 g∙mol -1The mixtures were concentrated to contain 33–60 wt% acetone and mixed with 3–5 wt% sodium iodide (NaI) for bonding. These viscous mixtures were applied to an area of approximately 2.5 x 3 cm on an aluminum plate (approx. 2.5 x 10 cm). A second aluminum plate was then placed on top of the bonded surfaces, and the bonded plates were dried at 40 °C for one to two days. A voltage was then applied to the bonded plates using a 9 V battery or a potentiostat, and the current flow was recorded. Figure 2 shows the current flow at a voltage of 5 V for the oligomer with a molar mass of 1100 g / mol. -1As can be seen in Figure 2, the curve showed a rapid rise to a maximum followed by an almost exponential decline. This corresponds to the expected course of constant voltage electrolysis. Furthermore, it was observed that after approximately 200 seconds at 5 V, the bonded plates separated without any external influence. This indicates successful debonding of the metal plates. A yellow discoloration of the bonded surface further suggests the formation of benzoquinone as a degradation product of the prepolymer and thus supports the postulated debonding mechanism. The components for debonding the invention underlying this patent application were developed in a project funded by the German Federal Ministry of Education and Research (BMBF) under grant number 222991543100011, project name SAVER2.
Claims
Patent claims 1. Use of a monomer according to formula (1) as specified below or its racemates, enantiomers, diastereomers or salts to produce a bond cleavage in a polymer obtained from at least one monomer according to formula (1), wherein the bond cleavage is induced by applying an electrical voltage across the polymer: in which: E 1 , E 2 is ZR 3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2;Z is O, S or N;R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20-Heteroaryl, C4-C20-heterocycloalkenyl or phenylethynyl are each unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4- C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R3, R4 for Z is O or S independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z is N independently selected from R'''2; R 5 , R 6 , R 5a , R 6a selected independently from the group comprising H and / or C1-C6 alkyl,R' selected independently from the group comprising H, C1-C30 alkyl,C3-C 10 -Cycloalkyl and / or C6-C 10-Aryl; R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C30 alkyl substituted with OH, NCO or COOH, R''' is independently selected from the group comprising H, C1-C30 alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C 1-C30-Alkyl; n, n a is an integer independently selected from 0, 1, 2, 3, 4 or 5.
2. Method for the electrochemical disintegration of a polymer obtained from at least one monomer according to formula (1) or its racemates, enantiomers, diastereomers or salts as specified below: in which: E 1 , E 2is ZR 3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2; Z ist O, S oder N; R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4- C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3, C6F5, [SR'2] + , [NR'3]+ , [PR'3] + and / or SO3 – ; R 3 , R 4 for Z, O or S is independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z, N is independently selected from R'''2; R 5 , R 6 , R 5a , R 6a R' is selected independently from the group comprising H and / or C1-C6 alkyl; R' is selected independently from the group comprising H, C1-C30 alkyl, C3-C10 cycloalkyl and / or C6-C10 aryl; R'' is selected independently from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30-Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n, n a is an integer independently selected from 0, 1, 2, 3, 4, or 5, wherein in step a) the polymer is provided and in step b) an electrical voltage is applied across the polymer, thereby causing bond rupture in the polymer.
3. Use according to claim 1 or method according to claim 2, characterized in that the polymer comprises repeating units according to the following formulas (2) to (6) or their racemates, diastereomers, or salts: worin: R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4- C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 –;X a polymerization partner obtained from at least one further monomer different from the monomer according to formula (1), preferably selected from the group comprising polyols, acids, diisocyanates, acrylic acid, acrylates, methacrylates and / or formaldehyde;Y is selected from the group comprising H, X and / or R''';R' independently selected from the group comprising H, C1-C30-alkyl,C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl; R''' independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30-Alkyl; is an integer selected from 0, 1, 2, 3, 4 or 5, m is an integer selected from 1, 2, 3, 4, o is an integer in the range of 2 to 200,000.
4. Use or method according to claim 3, characterized in that the polymer is a polyurethane comprising repeating units according to the following formula (7): where p is an integer in the range of 2 to 200,000.5.A method according to any one of claims 2 to 4, characterized in that, in step a), a mixture comprising the polymer, a solvent and optionally a salt is provided and, in step b), the mixture from step a) is electrolyzed in an electrochemical cell comprising an anode and a cathode which are in electrical contact with the mixture, or, in step a), the polymer is provided applied to a substrate, wherein the substrate optionally has an electrically conductive surface or is an electrically conductive substrate, and, in step b), a voltage is applied to the substrate and / or across the polymer, or, in step a), a composite comprising at least two joining parts and the polymer, wherein the polymer is applied between at least one surface of each joining part, and wherein, optionally, one or more further layers are applied between the surfaces of the joining parts, wherein the polymer or one of the further layers is applied. Layers form an adhesive bond between the surfaces of the joining parts, wherein the joining parts optionally have an electrically conductive surface or are electrically conductive, and in step b) a voltage is applied to the joining parts and / or across the polymer to break the bond of the joining parts.
6. Bond comprising at least one substrate, in particular two joining parts, and a polymer consisting of at least the monomer according to formula (1) or its racemates, enantiomers, diastereomers or salts: w orin: E 1 , E 2 is ZR 3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2; Z ist O, S oder N; R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -alkyl, C2-C30 alkenyl, C6-C20 aryl, C5-C20 heteroaryl, C4-C20 heterocycloalkenyl or phenylethynyl, where C1-C30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C20-Heterocycloalkenyl, C1-C30-Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3,C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R 3 , R 4 for Z is O or S independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z is N independently selected from R'''2; R 5 , R 6 , R 5a , R 6aR' is selected independently from the group comprising H and / or C1-C6 alkyl, R' is selected independently from the group comprising H, C1-C30 alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl; R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n, n ais an integer independently selected from 0, 1, 2, 3, 4 or 5, wherein the compound preferably is a V that can be released by applying an electrical voltage erbund ist.
7. Composition suitable for releasable bonding, comprising a polymerizable monomer according to formula (1) as specified below or its racemates, enantiomers, diastereomers or salts and / or a polymerizable prepolymer obtained from at least the monomer according to formula (1) specified below or its racemates, enantiomers, diastereomers or salts and optionally an electrically conductive additive: wherein: E 1 , E 2 is ZR 3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2; Z ist O, S oder N; R 1 , R 2 Selected independently from the group comprising H, C1-C 30-alkyl, C2-C30 alkenyl, C6-C20 aryl, C5-C20 heteroaryl, C4-C20 heterocycloalkenyl or phenylethynyl, where C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C20-Heterocycloalkenyl, C1-C30-Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3,C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R 3 , R 4For Z, O or S is independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z, N is independently selected from the group comprising R'''2; R5, R6, R5a, R6a is independently selected from the group comprising H and / or C1-C6 alkyl, R' is independently selected from the group comprising H, C1-C30 alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl; R'' is independently selected from the group comprising C1-C30 alkyl, C3-C30 cycloalkyl, C6-C10 aryl, C2-C30 alkenyl, C3-C30 alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C30-alkyl, C3-C30-cycloalkyl, C6-C10-aryl, NCO and / or C1-C substituted with NCO 30 -Alkyl; n, na is an integer independently selected from 0, 1, 2, 3, 4 or 5.
8. Polymerizable monomer, characterized in that the polymerizable monomer is a monomer according to formula (1) as specified below or its racemates, enantiomers, diastereomers or salts: in which: E 1 , E 2 is ZR 3 or ZR 4 or independently selected from the group comprising C(O)OH, C(O)OR'', C(O)R'' and / or C(O)NR'''2;Z is O, S or N;R 1 , R 2 Selected independently from the group comprising H, C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20 -Heterocycloalkenyl or phenylethynyl, wherein C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4-C 20-Heterocycloalkenyl or phenylethynyl are either unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C2-C 30 -Alkenyl, C3-C 10 -Cycloalkyl, C6-C 20 -Aryl, C5-C 20 -Heteroaryl, C4- C 20 -Heterocycloalkenyl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – ; R 3 , R 4 for Z, O or S is independently selected from the group comprising H, C(O)OR'', C(O)R'', C(O)NR'''2 and / or R'', or for Z, N is independently selected from R'''2; R 5 , R 6 , R 5a , R 6aR' is selected independently from the group comprising H and / or C1-C6 alkyl; R'' is selected independently from the group comprising H, C1-C30 alkyl, C3-C10 cycloalkyl and / or C6-C10 aryl; R'' is selected independently from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30 -Alkyl,R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or simply or multiple substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n, n ais an integer independently selected from 0, 1, 2, 3, 4 or 5, where: a) for Z is O, n is 0 and R 3 and R 4 are H, R 1 and R 2 are not simultaneously unsubstituted phenyl, b) for Z is O, n is 1 and R 3 and R 4 are H, R 1 and R 2 not simultaneously H, CH2Cl, unsubstituted phenyl or phenylethynyl, or with C 10 -aryl substituted phenyl are, or c) for Z is O, n is 1 and R1 and R2 are H, R3 and R4 are not simultaneously C(O)NR'''2 with R''' being H or a group selected from (13) are.
9. Polymerizable monomer according to claim 8, characterized in that the polymerizable monomer is a monomer according to formula (10) as specified below or its racemates, enantiomers, diastereomers or salts: in which: R 1 , R 2independently of one another phenyl, pyridinyl or phenylethynyl, each singly or multiply substituted with substituents selected from the group comprising C1-C30 alkyl, C3-C 10 -Cycloalkyl, C6-C 10 -Aryl, C1-C 30 -Alkoxy, CN, SCN, NC, NCO, NO2, Halogen, CF3, C6F5, [SR'2] + , [NR'3] + , [PR'3] + and / or SO3 – , or unsubstituted pyridinyl; R 3 , R 4 R' is selected independently from the group comprising H, C(O)OR'', C(O)R'', C(O)NR''''2 and / or R''; R' is selected independently from the group comprising H, C1-C30-alkyl, C3-C 10 -Cycloalkyl and / or C6-C 10 -Aryl; R'' independently selected from the group comprising C1-C30 alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, C2-C 30 -Alkenyl, C3-C 30 -Alkyl epoxides and / or C1-C substituted with OH, NCO or COOH 30-Alkyl, R''' is independently selected from the group comprising H, C1-C30-alkyl, phenyl and / or benzyl, wherein phenyl and benzyl are unsubstituted or singly or multiply substituted with substituents selected from the group comprising C1-C 30 -Alkyl, C3-C 30 -Cycloalkyl, C6-C 10 -Aryl, NCO and / or NCO-substituted C1-C 30 -Alkyl; n is an integer selected from 0, 1, 2, 3, 4 or 5.
10. Polymer obtained from at least the polymerizable monomer according to claim 8 or 9 and preferably at least one further monomer different therefrom selected from the group comprising polyols, acids, diisocyanates, acrylic acid, acrylates, methacrylates and / or formaldehyde.
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