EP4363374A1

EP4363374A1 - Polyalkylene oxides as dispersants for graphene material

Info

Publication number: EP4363374A1
Application number: EP22740830.9A
Authority: EP
Inventors: Kathrin Lehmann; Stefan Schumann; Valeri LEICH; Verena BREUERS; Jonas HÖNIG; Lea Muchajer; Thorsten Hoven; Peter Seidensticker
Original assignee: Evonik Operations GmbH
Current assignee: Evonik Operations GmbH
Priority date: 2021-07-02
Filing date: 2022-06-29
Publication date: 2024-05-08
Also published as: TW202311355A; WO2023275135A1; CN117597306A; KR20240027790A; CA3224256A1

Abstract

The present invention provides for the use of polyalkylene oxides containing at least one aromatic radical as dispersants for graphene material; a method for dispersing graphene material using the aforesaid polyalkylene oxides as dispersants; and compositions comprising the aforesaid dispersant and graphene material.

Description

Polyalkylene oxides as dispersants for graphene material

The present invention relates to polyalkylene oxides as dispersants for graphene material. Graphene material is used in a variety of technical fields. Extensive treatises on graphene, its production, properties and applications can be found in the specialist literature (see Römpp online, https://roempp.thieme.de/lexicon/RD-07-02758; Anaew. Chem. Int. Ed. 2014, 53, 7714-7718; Mater Today 2012, 15(3) 86-97). Graphene material is commercially available as a powder and often has very low bulk densities, ranging somewhere between 2 and 400 g/l. In addition to the low bulk densities, graphene material also has poor pourability and develops a high dust content when poured. This leads to poor handling, problems with weighing and dosing and must also be viewed critically from the perspective of environmental protection and occupational safety. Closed systems for feeding solids are also only of limited use, as they can address occupational safety issues, but so-called bridging in the continuous or semi-continuous dosing of graphene material in dispersing containers, kneaders or extrusion lines cannot be solved. Bridging is to be understood as meaning inhomogeneous dosing of solids which can lead to blockage of the feeder and thus require the unwanted opening and mechanical exposure of the feeder. Volumetric dosing is therefore often not feasible at all and gravimetric dosing is disrupted.

The poor handling is also evident, for example, when the powdery graphene material is incorporated into solvents and monomer resins (monomer resins) for so-called thermal interface materials as well as sealants and adhesives. In general, the incorporation of graphene material into liquid systems poses a challenge. In order to produce a well-filled sealant and adhesive, for example, the right point in time and the duration of the incorporation of powdery fillers are usually important. The shear forces acting during the mixing process break up filler agglomerates and thus contribute to distribution. The maximum degree of filling that can be achieved is therefore largely determined by the acting shear forces. Solvents and resins alone cannot adequately bind and stabilize freshly generated surfaces and functional groups, leading to separation and sedimentation. This means that it is not possible to achieve a usable, stable dispersion for further processing in formulations. Furthermore, precise and reliable dosing for sealants and adhesives with an easily controllable viscosity is important in order to achieve good interface contacts and thus strong adhesion or thermal and electrical conductivity in applications. The quality of the adhesive or sealant and the strength of the effect to be achieved, such as increased thermal or electrical conductivity, are heavily dependent on the dispersibility of the fillers and their influence on the Properties of the overall formulation (e.g. viscosity). The foregoing discussions also apply to other liquid systems.

However, creating stable dispersions of graphene material is problematic. Graphene material tends to agglomerate. These aggregates in turn lead to sedimentation, which is undesirable.

In order to improve the dispersibility of graphene material in solid and liquid systems, the use of dispersing agents is suggested in the prior art.

For example, WO 2012/059489 A1 discloses polymer compositions, in particular for thermoplastics or thermosets, which contain electrically conductive carbon substrates such as carbon black, carbon fibers, graphite, graphene and/or CNTs (carbon nanotubes) and salts with a non-metallic cation or a synergistic mixture of these salts together with metal salts, whereby the combination with special dispersing agents is essential. These special dispersing agents are dispersing agents based on esters or amides. It is preferred that the dispersants are selected from c1) polyacrylic acid esters, preparable by transesterification of a polyacrylic acid alkyl ester obtainable by polymerization, whose alkyl radicals have 1 to 3 carbon atoms, with a) saturated aliphatic alcohols having 4 to 50 carbon atoms and/or b) unsaturated aliphatic alcohols Alcohols having 4 to 50 carbon atoms, where a) and b) are used in such amounts that 30 to 100% of the ester groups are transesterified, and / or c2) polyester-polyamine condensation products obtainable by the partial or complete implementation of

A) one or more amino-functional polymers containing at least four amino groups

B) one or more polyesters of the general formulas (l)/(la)

TC(0)-[0-AC(0)] _x -0H (I)

T -0-[C(0)-A-0-] _y -Z (la) and

C) one or more polyethers of the general formula (II)/(IIa)

T-C(0)-B-Z (II)

TOBZ (lla) wherein

T is a hydrogen radical and/or an optionally substituted, linear or branched aryl, arylalkyl, alkyl or alkenyl radical having 1 to 24 carbon atoms,

A is at least one divalent radical selected from the group of linear, branched, cyclic and aromatic hydrocarbons,

Z is at least one radical selected from the group of sulfonic acids,

Sulfuric acids, phosphonic acids, phosphoric acids, carboxylic acids, isocyanates, epoxides, in particular phosphoric acid and (meth)acrylic acid,

B is a radical of general formula (III).

-(ClH _2l O)a-(CmH2mO)b-(CnH ₂ nO)c-(SO)d- (III)

SO = -CH ₂ -CH(Ph)-0- with Ph = phenyl radical, a,b,c are independently values from 0 to 100, with the proviso that the sum of a + b + c > 0, preferably 5 to 35, in particular 10 to 20, with the proviso that the sum of a+b+c+d>0, d>0, preferably 1 to 5, l,m,n independently of one another>2, preferably 2 to 4, x,y are independently > 2.

The commercially available products TEGOMER® DA 100 N (Evonik), TEGOMER® DA 102 (Evonik) and TEGOMER® P121 (Evonik) are described as examples of the dispersants c1). The commercially available product TEGOMER® DA 626 (Evonik) is again mentioned as an example of the dispersants c2). Thus, many different dispersants are disclosed, which in turn are useful for dispersing many different carbon substrates. The combination of graphene material and polyalkylene oxides having at least one aromatic radical is not disclosed.

Other commercially available polyester-polyamine condensation products are also known from the prior art, such as Solsperse® 39000 (Lubrizol). Solsperse® 39000 has no aromatic residues. EP 1078946 A1 describes styrene oxide-containing polyalkylene oxide block copolymers obtained by alkoxylation and their use as low-foaming pigment wetting agents in aqueous pigment pastes, optionally containing co-solvent, aqueous and low-solvent paints and printing inks. Numerous inorganic and organic pigments are mentioned as pigments. The dispersing additives are said to be particularly preferred for the production of aqueous (gas) carbon black pastes. Specifically, black pastes are described which, in addition to the polyalkylene oxides mentioned, also contain carbon black (Raven® 1170). However, graphene material is not disclosed.

There was therefore a continuing need for graphene material dispersants that have at least one advantage over the prior art. In particular, these dispersants should allow high filling levels of graphene material and enable stable dispersions with low viscosities. In addition, the dispersants should enable graphene material to be dispersed in both polar and non-polar, continuous, preferably liquid phases, with the continuous, preferably liquid phases being intended in particular to be solvent, monomer, oligomer or polymer compositions.

Surprisingly, it has now been found that the use of polyalkylene oxides which have at least one aromatic radical as a dispersant for graphene material solves this problem.

A first object of the present invention is therefore the use of polyalkylene oxides which have at least one aromatic radical as a dispersant for graphene material.

A further object of the present invention is a method for dispersing graphene material, characterized in that the polyalkylene oxides used according to the invention are used as dispersing agents.

Yet another object of the present invention is a composition comprising or consisting of: (a) a continuous phase,

(b) a dispersing agent corresponding to the use according to the invention, and

(c) graphene material.

Yet another object of the present invention is a composition comprising or consisting of:

(i) a dispersing agent corresponding to the use according to the invention, and

(j) Graphene Material.

Advantageous configurations of the objects of the invention can be found in the claims, the examples and the description. In addition, it is expressly pointed out that the disclosure of the subject matter of the present invention includes all combinations of individual features of the description of the invention and the patent claims. In particular, embodiments of an object according to the invention also apply mutatis mutandis to the embodiments of the other objects according to the invention. The inventors found that using polyalkylene oxides containing at least one aromatic group as dispersants for graphene material has several advantages:

An advantage of the invention is the improved dispersibility of graphene material in polar as well as non-polar continuous, preferably liquid, phases, in particular selected from the group consisting of solvent, monomer, oligomer and polymer compositions. In contrast to this, the dispersants for graphene material known from the prior art are only compatible with very few continuous phases and tend to separate or inefficiently disperse even at very high dispersant concentrations.

Another advantage of the invention is that dispersions with high loading levels of graphene material can be obtained. Due to the high degree of filling, electrical and thermal conductivity of the dispersions can be achieved or improved.

Another advantage of the invention is improved handling and dosage in formulations, especially compared to graphene powders.

An advantage of the invention is also improved safety in handling, especially compared to powdered graphene material.

Another advantage of the invention is that the viscosity of compositions containing graphene material can be adjusted in a targeted manner. This is because the viscosity usually increases sharply during the dispersion of graphene material and can even lead to the compositions solidifying, as a result of which the compositions can become unusable. In the case of very low viscosities, on the other hand, the shearing effect during dispersing cannot be introduced in a targeted manner. This makes the dispersion process inefficient and does not result in sufficient dispersion of the graphene material. The polyalkylene oxides used according to the invention, on the other hand, act as viscosity-modifiers and allow the viscosity to be set in a targeted manner in order to enable effective dispersion at low and at high viscosity and to obtain a stable, highly loaded dispersion of the graphene material.

A further advantage of the invention is that the polyalkylene oxides used according to the invention do not adversely affect the intrinsic properties of the graphene material. The incorporation of the dispersion into thermoplastic, duroplastic or elastomeric polymer systems for adhesives and sealants is significantly facilitated or even made possible in the first place.

The objects according to the invention and their preferred embodiments are described below by way of example, without the invention being limited to these examples Embodiments should be limited. If ranges, general formulas or compound classes are specified below, these should not only include the corresponding ranges or groups of compounds that are explicitly mentioned, but also all sub-ranges and sub-groups of compounds that are obtained by removing individual values (ranges) or compounds can become. Any embodiment that can be obtained by combining regions/partial regions and/or groups/partial groups fully belongs to the disclosure content of the present invention and is considered to be disclosed explicitly, directly and unambiguously. If mean values are given below, they are numerical means unless otherwise stated. If measured values or material properties are given below, unless otherwise stated, these are measured values or material properties measured at 25° C. and preferably at a pressure of 101325 Pa (normal pressure). Room temperature (RT) means a temperature of 25 °C.

If number ranges are given below in the form "from X to Y" or "X to Y", with X and Y representing the limits of the number range, this is equivalent to the statement "from at least X up to and including Y", unless otherwise stated . Range specifications include the range limits X and Y, unless otherwise stated.

Wherever molecules or molecular fragments have one or more stereocenters or can be distinguished into isomers by symmetry or can be distinguished into isomers by other effects such as restricted rotation, all possible isomers are encompassed by the present invention.

The word fragment "poly" includes compounds that are made up of at least two monomer units.

The word fragment "Cx-Cy ^" when referring to a compound or group means a compound or group having x to y carbon atoms. The designation “Ci-C2o-organyl radical” therefore stands for an organyl radical, ie an organic radical with 1 to 20 carbon atoms. The designation “Ci-Ce-acyl radical” correspondingly stands for an acyl radical with 1 to 8 carbon atoms. The designation "Ci-Cs-alkyl radical" accordingly stands for an alkyl radical having 1 to 8 carbon atoms. The designation “C6-Ci3-hydrocarbon radical” correspondingly designates a hydrocarbon radical with 6 to 13 carbon atoms.

The following formulas describe compounds or structural units, which in turn may be made up of repeating units, such as repeating fragments, blocks, or monomer units, and may have a molecular weight distribution. the Frequency of these repeating units is indicated by indices. The corresponding indices are the numerical average (number average) over all repeat units unless otherwise indicated. The indices of these units used in the formulas are therefore to be regarded as statistical averages (number averages), unless otherwise stated. The index numbers used and the value ranges of the specified indices are therefore understood to be mean values of the possible statistical distribution of the structures actually present and/or their mixtures, unless otherwise stated. The repeating units in the formulas below can be distributed arbitrarily. The structures built up from the repeating units can be built up in blocks with any number of blocks and any sequence or they can be subject to a randomized distribution; they can also have an alternating structure or also form a gradient via the chain, if such a chain is present; in particular, they can also form all mixed forms in which groups of different distributions can follow one another, if appropriate. Special implementations can result in the statistical distributions being restricted by the implementation. For all areas that are not affected by the restriction, the statistical distribution does not change.

The first object of the invention is the use of polyalkylene oxides, which have at least one aromatic radical, as a dispersant for graphene material.

The plural “polyalkylene oxides” stands for a polyalkylene oxide or several polyalkylene oxides, preferably several polyalkylene oxides.

The singular "graphene material" means one or more graphene materials, preferably one graphene material.

The “use of polyalkylene oxides that have at least one aromatic group as a dispersant for graphene material” is therefore equivalent to the “use of one or more polyalkylene oxides that have at least one aromatic group as a dispersant for one or more graphene materials. “.

The “use of polyalkylene oxides that have at least one aromatic group as a dispersant for graphene material” is therefore synonymous with the “use of at least one polyalkylene oxide that has at least one aromatic group as a dispersant for at least one graphene material.” .

The polyalkylene oxides are therefore also referred to below as dispersants. The dispersing agent thus consists of the polyalkylene oxides which can be used according to the invention. The polyalkylene oxides which can be used according to the invention must have at least one aromatic radical in order to achieve the object of the invention. Without being bound by theory, it is believed that the aromatic moiety enhances the interaction of the polyalkylene oxides with the graphene material.

It is preferred that the at least one aromatic radical is a phenyl radical.

In order to achieve an optimal effect, it is also preferred that the mass fraction of all aromatic residues, based on the total mass of the dispersant, is from 2% to 40%, preferably from 5% to 25%, in particular from 7% to 15%.

The polyalkylene oxides contain units of the formula (A) wherein the radicals R ^A , R ^B , R ^c and R ^D are each independently organic radicals or hydrogen (H). The organic radicals can each independently be linear or branched or cyclic, saturated or unsaturated, aliphatic or aromatic, substituted or unsubstituted, or a combination thereof, where possible (eg cycloaliphatic). The proviso here is that at least one unit is present in which at least one of the radicals ^RA , RB, ^Rc and ^RD ^is an aromatic radical. The organic radicals are preferably hydrocarbon radicals which contain no heteroatoms, in particular Ci-Ce hydrocarbon radicals which contain no heteroatoms. It is preferred that the polyalkylene oxides contain units in which exactly one of the four radicals ^RA , RB, ^Rc and ^RD is a phenyl radical and the other three radicals are ^hydrogen (H). It is therefore preferred that the polyalkylene oxides have at least one unit of the formula -O-CH ₂ -CHPh- or of the formula -CH ₂ -CHPh-O-, where Ph is a phenyl radical.

It is further preferred that the polyalkylene oxides are selected from compounds of the general formula (B),

R ¹ [0(S0)a(P0)b(B0)c(E0)dR ² ]n (B) where the following applies: R ¹ is in each case independently selected from the group of n-bonded ones

Ci-C2o organyl radicals;

R ² is each independently selected from the group consisting of Ci-Cs-acyl radicals, Ci-Cs-alkyl radicals and hydrogen, SO = styrene oxide,

PO = propylene oxide,

BO = butylene oxide,

EO = ethylene oxide, n = 1 to 6, preferably 1 to 4, in particular 1 to 3, a = 1 to 10, preferably 1 to 5, in particular 1 to 3, b = 0 to 50, preferably 0 to 20, in particular 0 to 15, c = 0 to 10, preferably 0 to 5, in particular 0 to 3, d = 0 to 50, preferably 0 to 20, in particular 0 to 15.

It is preferred in formula (B) that a+b+c+d>3.

For example, it is preferred that the polyalkylene oxides are selected from compounds of general formula (C),

R ¹ 0(S0)a(P0) _b (B0)c(E0)dR ² (C) where:

R ¹ is each independently selected from the group of monovalent C6-Ci3 hydrocarbon radicals,

R ² is each independently selected from the group consisting of Ci-Cs-acyl radicals, Ci-Ce-alkyl radicals and hydrogen,

SO = styrene oxide,

PO = propylene oxide,

BO = butylene oxide,

EO = ethylene oxide, a = 1 to 1.9, b = 0 to 3, c = 0 to 3, d = 3 to 50, with the proviso that d > a+b+c.

It is preferred in formula (C) that a+b+c+d>3.

It is further preferred that the polyalkylene oxides are selected from compounds of the general formula (D),

R ¹ [0(S0)a(P0)b(B0)c(E0)dR ² ]n (D) where:

R ¹ is each independently selected from the group of n-bonded Ci-C2o-organyl radicals; R ² is each independently selected from the group consisting of Ci-Ce-acyl radicals, Ci-Cs-alkyl radicals and hydrogen,

SO = styrene oxide,

PO = propylene oxide,

BO = butylene oxide,

EO = ethylene oxide, n = 1 to 6, preferably 1 to 4, in particular 1 to 3, a = 1 to 10, preferably 1 to 5, in particular 1 to 3, b = 0 to 50, preferably 3 to 20, in particular 3 to 15, c=0, d=0.

In the case of the formula (B) or (C) or (D), it is preferred that a+b+c+d>3, preferably>4, in particular>5.

In formula (B) or (C) or (D), SO (styrene oxide) represents a unit of the formula (A) in which exactly one of the four radicals ^{RA, R B} ^, R ^c and R ^D is a phenyl radical is and the remaining three radicals are hydrogen (H).

In formula ( ^B ) or ( ^C ) or ( ^D ), EO (ethylene oxide) represents a unit of the formula (A) in which all four radicals ^RA , RB , Rc and RD are hydrogen (H). .

In formula ( ^B ) or ( ^C ) or ( ^D ), PO (propylene oxide) represents a unit of the formula (A) in which precisely one of the four radicals ^RA , RB, Rc and RD is a methyl radical is and the remaining three radicals are hydrogen (H).

In formula ( ^B ) or ( ^C ) or ( ^D ), BO (butylene oxide) represents a unit of the formula ( ^A ) in which exactly one of the four radicals RA, RB, Rc and RD is an ethyl radical and the other three radicals are ^hydrogen (H) or in which exactly two of the four radicals ^RA , RB, ^Rc and ^RD are methyl radicals and the other two radicals are hydrogen (H).

The person skilled in the art is familiar with the fact that the compounds of the formula (B) or (C) or (D) are usually present as a mixture. The hydrophobic/hydrophilic balance can be controlled by the various alkylene oxide monomers and their proportion in the overall polymer in such a way that the dispersant can be tailored to the graphene material and the continuous phase. EO units are hydrophilic, and PO, BO and SO units are hydrophobic.

The alkylene oxide units can be arranged, for example, randomly or in blocks. The alkylene oxide units are particularly preferably arranged in blocks. The polyalkylene oxides are therefore preferably block copolymers. The polyalkylene oxides are therefore preferably block-copolymeric polyalkylene oxides. It is thus preferred that the polyalkylene oxides are block-copolymeric, styrene oxide-based polyalkylene oxides. It is preferred that the hydrophobic units such as SO, PO or BO and the hydrophilic EO units form separate blocks. It is preferred that the hydrophilic EO moieties form a block attached to R ² . R ² is preferably hydrogen (H). The hydrophobic moieties SO, PO and BO are preferably located between the EO block and R ¹ . It is therefore preferred that the radical R ¹ , the SO, PO and BO units, and the oxygen atom(s) connecting R ¹ to the alkylene oxide units form a contiguous part in the polyalkylene oxide , to which in turn the EO units terminated by R ² are bound. In one case it can be preferred that in formula (B) or (C) or (D) d>a+b+c and in another case that in formula (B) or (C) and (D) d < a+b+c, respectively. In the first case, the polyalkylene oxides are more hydrophobic, in the second case more hydrophilic. In addition to carbon and hydrogen atoms, R ¹ can also include heteroatoms, for example selected from N and O, in particular N. However, it is preferred that R ¹ includes no SO units, no PO units, no BO units and no EO units . R ¹ preferably has no heteroatoms. R ¹ is preferably each independently selected from the group of monovalent C6-Ci3-hydrocarbon radicals. Preferably, each R ¹ is independently linear (ie, unbranched) or branched or cyclic, saturated or unsaturated, aliphatic or aromatic, or a combination thereof where possible. More preferably, each R ¹ is independently a saturated aliphatic radical, linear or branched. It is even more preferred that R ¹ is a linear or branched or cycloaliphatic radical having 6 to 13 carbon atoms. Even more preferably, R ¹ is a linear, aliphatic radical, in particular selected from the group consisting of n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl. Suitable compounds of the formula (B) or (C) or (D) and their syntheses are described in EP 1 078 946 A1 and are commercially available, for example, under the name TEGOMER® DA 646. The radical R ¹ is derived from corresponding hydroxy-functional compounds R ¹ (OH) _n , where n is as defined in formula (B) or (D). Examples of suitable hydroxy-functional compounds R ¹ (OH) _n can be found in the examples (see Table 1). Other suitable hydroxy-functional compounds R ¹ (OH) _n can be selected from the group of sugars and sugar alcohols, such as glucose, gulose and sorbitol. Furthermore, polyglycerols can also be used as hydroxy-functional compounds R ¹ (OH) _n .

It is preferred that R ² comprises no SO moieties, no PO moieties, no BO moieties and no EO moieties. R ² is preferably hydrogen (H). It is preferred that the number-average molecular weight (M _n ) of the polyalkylene oxides is from 400 g/mol to 4000 g/mol, preferably from 500 g/mol to 2500 g/mol, in particular from 600 g/mol to 1500 g/mol. The number-average molecular weight (M _n ) is preferably determined by means of gel permeation chromatography (GPC).

In addition to oxygen atoms, the polyalkylene oxides can also comprise further heteroatoms, such as nitrogen atoms, for example. However, it is preferred that the polyalkylene oxides contain no phosphorus atoms. It is furthermore preferred that the polyalkylene oxides contain no sulfur atoms. It is therefore also preferred that the polyalkylene oxides contain no further heteroatoms apart from oxygen and optionally nitrogen atoms. The polyalkylene oxides are therefore preferably composed only of carbon, hydrogen, oxygen and optionally nitrogen atoms. The polyalkylene oxides therefore preferably consist of carbon, hydrogen, oxygen and optionally nitrogen atoms. It is particularly preferred that the polyalkylene oxides contain no further heteroatoms apart from oxygen atoms. The polyalkylene oxides are therefore particularly preferably composed only of carbon, hydrogen and oxygen atoms. The polyalkylene oxides therefore particularly preferably consist of carbon, hydrogen and oxygen atoms.

It is also preferred that the graphene material is a graphene material according to ISO-TS 80004-13, preferably selected from the group consisting of monolayer graphene, bilayer graphene, trilayer graphene, few-layer graphene, multi-layer graphene, one to ten layer graphene, epitaxial graphene, exfoliated graphene, graphene nanoribbons, graphene nanoplates, graphene nanoplatelets, graphene nanosheets, graphene microsheets, graphene nanoflakes, graphene quantum dots, graphene oxide, graphene oxide nanosheets, multi-layer graphene oxide and reduced graphene oxide, and their mixtures, with particular preference being given to graphene material with one to ten graphene layers.

It is preferred that the graphene material has a carbon fraction (mass fraction of carbon based on the total mass of the graphene material) of at least 80%, preferably at least 90%, in particular at least 95%.

The graphene material is preferably a single-layer or multi-layer graphene material, ie a graphene material that comprises one or more graphene layers. Graphene material with two to ten graphene layers is preferably used as the multilayer graphene material.

It is preferred that the graphene material has a thickness of less than 10 nm, preferably less than 5 nm, in particular less than 3 nm. It is preferred that the graphene material has a bulk density of from 0.01 g/cm ³ to 0.10 g/cm ³ , preferably from 0.01 g/cm ³ to 0.08 g/cm ³ , in particular from 0. 0.1 g/cm ³ to 0.05 g/cm ³ .

Preferably, the graphene material is in the form of granules, flakes, powder, films, layers, platelets, nanoribbons and/or fibers.

Further details on graphene material, its production, properties and applications can also be found in the specialist literature (see Römpp online, httosV/roemoo.thieme.de/lexicon/RD-07-02758; Angew. Chem. Int Ed. 2014, 53, 7714-7718; Mater Today 2012, 15(3), 86-97).

The graphene material can be dispersed in liquid continuous phases using the aforementioned polyalkylene oxides. It is preferred that the graphene material is dispersed in a liquid continuous phase, the main component of which is compounds selected from the group consisting of polyethers, in particular polyether polyols, polyesters, in particular polyester polyols, polycarbonates, in particular polycarbonate polyols, polybutadienes, in particular polybutadiene polyols, epoxy resins, polysiloxanes , silicone oils, vegetable oils, mineral oils, synthetic organic oils, silyl-modified polymers, silyl-modified reactive diluents, (meth)acrylic acid, (meth)acrylates, cyanoacrylates, dihydrolevoglucosenone (Cyrene®), dimethylformamide (DMF), organic carbonates, acetone, glycols, dimethyl sulfoxide (DMSO ), tetrahydrofuran (THF), methyl ethyl ketone (MEK), acetates, N-methyl-2-pyrrolidone (NMP), alcohols and dibasic esters (DBE).

Preferably, the vegetable oil is selected from the group consisting of linseed oil, soybean oil, rapeseed oil, castor oil, epoxidized linseed oil, epoxidized soybean oil, epoxidized rapeseed oil and epoxidized castor oil,

The silyl-modified polymers preferably have triethoxysilyl and/or trimethoxysilyl groups. It is preferred that the polymer backbone is a polysiloxane (silicone), polybutadiene, or a polyether backbone.

The term “(meth)acrylic acid” stands for methacrylic acid and/or acrylic acid. The designation “(meth)acrylate” stands for methacrylic acid ester and/or acrylic acid ester. The (meth)acrylates are preferably selected from the group consisting of n-butyl methacrylate, isobutyl methacrylate, cyclohexyl methacrylate, 2-hydroxyethyl methacrylate, 2-ethylhexyl methacrylate, methyl methacrylate, ethyl methacrylate, vinyl methacrylate, n-butyl acrylate, isobutyl acrylate, cyclohexyl acrylate, 2-hydroxyethyl acrylate , 2-ethylhexyl acrylate, methyl acrylate, ethyl acrylate and vinyl acrylate.

The organic carbonates are preferably selected from the group consisting of dimethyl carbonate, propylene carbonate, allyl ethyl carbonate, vinylene carbonate, methyl ethyl carbonate, ethylene carbonate, fluoroethylene carbonate, butylene carbonate, diethyl carbonate, methyl propyl carbonate, ethyl propyl carbonate, methyl isopropyl carbonate, dipropyl carbonate, dibutyl carbonate and chloroethylene carbonate.

The glycols are preferably selected from the group consisting of ethylene glycol, diethylene glycol. triethylene glycol. Tetraethylene Glycol, Propylene Glycol, Dipropylene Glycol, Tripropylene Glycol and Tetrapropylene Glycol.

The acetates are preferably selected from the group consisting of methyl acetate and ethyl acetate, n-propyl acetate and n-butyl acetate.

The alcohols are preferably selected from the group consisting of ethanol, methanol, propanol, isoamyl alcohol, 1-butanol, isopropanol, phenoxyethanol and 2-(2-phenoxyethoxy)ethanol.

The dibasic esters (DBE) are preferably selected from the group consisting of dimethyl succinate (DBE-4), dimethyl glutarate (DBE-5) and dimethyl adipate (DBE-6). Mixtures are commonly used, such as DBE-9, which is a mixture of DBE-4 and DBE-5.

It is further preferred that the continuous phase contains a plasticizer selected from the group consisting of phthalates, citrates and adipates as the main component.

It is further preferred that the continuous phase contains a baking lacquer, e.g. based on silicone, as the main component.

It is further preferred that the continuous phase contains an unsaturated polyester resin (UPES) or vinyl ester resin as a main component.

It is further preferred that the continuous phase contains a phenoplast (UF, MUF) or an aminoplast as the main component.

The main component of the continuous phase is understood to mean the component of the continuous phase that is predominant in terms of its mass fraction. It is preferred that the mass fraction of the main component is at least 50%, preferably at least 90%, in particular 100% based on the total mass of the continuous phase, with the upper limit being 100%. Another subject of the present invention is a method for dispersing graphene material, characterized in that the polyalkylene oxides used according to the invention are used as dispersing agents. It is preferred that the method comprises the following, directly or indirectly consecutive, preferably immediately consecutive, method steps: a) submission of a continuous phase; b) addition of a dispersing agent corresponding to the use according to the invention; c) Addition and dispersion of graphene material.

Alternatively, it is preferred that the process comprises the following, directly or indirectly consecutive, preferably immediately consecutive, process steps: i) submission of a dispersing agent corresponding to the use according to the invention; j) Addition and dispersion of graphene material.

The term “dispersant” is to be understood here as meaning the aforementioned polyalkylene oxides. The dispersing agent thus consists of one or more of the polyalkylene oxides which can be used according to the invention. The dispersing preferably takes place under the action of shearing. This achieves a high energy input. This leads to the breaking up of the agglomerates and exfoliation, creating fresh, unsaturated surfaces. These points of attack, namely functional groups such as hydroxyl, carboxy, aldehyde, keto, epoxy and amino groups, and conjugated systems are suitable for attachment to various dispersants and stabilizers. Such in-situ additives make the dispersion very effective, resulting in higher filling levels and more stable dispersions. Higher filling levels then allow greater flexibility in the formulation for the end use such as adhesives and sealants as well as thermal interface materials.

In the process according to the invention, in particular in step c) or j), various dispersing techniques and apparatuses can be used, such as apparatuses selected from the group consisting of bead mill, dissolver (e.g. DISPERMAT® dissolver), three-roll mill, Ultra-Turrax, Wet jet mill, conching machine, high shear mixer, preferably high speed mixer, high speed mixer and thermomixer. The dispersion can also take place by means of ultrasound. The dispersion is particularly preferably carried out using a dissolver (e.g. DISPERMAT® dissolver) or a bead mill.

It is preferred that the power or energy is introduced or applied for 0.1 min to 99 h, preferably for 0.1 min to 2 h, particularly preferably for 1 min to 15 min. The method according to the invention has the advantage of being very easy to carry out and thus of being able to produce compositions which have a high proportion by mass of graphene material.

(a) a continuous phase,

(b) a dispersing agent corresponding to the use according to the invention, and

(c) graphene material. Here, too, the dispersant is to be understood as meaning the aforementioned at least one polyalkylene oxide. The dispersing agent thus consists of one or more of the polyalkylene oxides which can be used according to the invention.

It is preferred that the mass fraction of component (c) based on the mass of the composition is from 0.1% to 90%, preferably from 5% to 60%, in particular from 25% to 40%. The mass of component (c) divided by the mass of the composition is thus from 0.1% to 90%, preferably from 5% to 60%, in particular from 25% to 40%.

It is preferred that the mass fraction of component (b) based on the mass of component (c) is from 0.01% to 200%, preferably from 30% to 150%, in particular 50% to 100%.

The mass of component (b) divided by the mass of component (c) is therefore from 0.01% to 200%, preferably from 30% to 150%, in particular 50% to 100%.

(i) a dispersing agent, according to the use according to the invention, and 0 graphene material.

Here, too, the dispersant is to be understood as meaning the aforementioned at least one polyalkylene oxide. The dispersing agent thus consists of one or more of the polyalkylene oxides which can be used according to the invention.

It is preferred that the mass fraction of component (j) based on the mass of the composition is from 0.1% to 90%, preferably from 5% to 60%, in particular from 25% to 40%. The mass of component (j) divided by the mass of the composition is thus from 0.1% to 90%, preferably from 5% to 60%, in particular from 25% to 40%.

It is preferred that the mass fraction of component (i) based on the mass of component (j) is from 0.01% to 200%, preferably from 30% to 150%, in particular 50% to 100%. The mass of component (i) divided by the mass of component (j) is therefore from 0.01% to 200%, preferably from 30% to 150%, in particular 50% to 100%.

The composition according to the invention can also contain other additives, such as fillers to improve the electrical conductivity, preferably selected from the group consisting of poly-3,4-ethylenedioxythiophene (PEDOT), polyaniline, carbon nanotubes, carbon black, carbon fibers, metal particles, metal fibers, silver nanowires, graphite (e.g. expanded graphite) and manganese oxide; Fillers to improve thermal conductivity, preferably selected from the group consisting of hBN, AIN, Al2O3, S1O2, ZnO, MgO, SiC, nanodiamonds; flame retardants; impact modifiers; color pigments; UV stabilizers;

viscosity modifiers; flow aids; defoamers; ionic liquids; wetting agents; and/or anti-scratch agents.

The combination of components (a), (b) and (c) gives a stable dispersion, preferably with a low viscosity, even when (c) is filled to a high degree.

Correspondingly, the combination of components (i) and (j) with a high degree of filling of (j) also provides a stable dispersion, preferably with low viscosity. The compositions according to the invention, in particular in the form of a paste, can be used in a variety of ways, e.g. Hose systems, membranes, fuel cells, cable systems, for electromagnetic shielding (EMC), for thermal management in battery systems, as well as for adhesives and sealants as well as potting compounds.

The compositions according to the invention, in particular in the form of a paste, are also suitable as an additive for the following materials: elastomers, duroplastics, thermoplastics, thermoplastic elastomers.

The compositions according to the invention, in particular in the form of a paste, are particularly suitable as an additive for the following materials/applications:

- Adhesives and sealants (especially for electrically and / or thermally conductive) including epoxy resins, phenolic resins, polyurethanes, silane-modified polymers (silyl-modified polymers, SMP), acrylates, reactive hot melts,

- Silicones (RTV, HTV, LSR, HCR),

- acrylates,

- Polyurethanes, e.g. thermoplastic polyurethanes, - Rubber, preferably SBR, BR, natural rubber, polybutadiene, functionalized polybutadiene,

- Duromers, preferably polyurethanes, polyester resins, phenolic resins, epoxy resins, acrylate resins, silicone resins,

- Thermal Interface Materials: Gap filier, tapes, greases and phase change materials, potting, packaging, underfills, casts, coatings, protective coatings,

- Thermoplastics, selected from standard thermoplastics, preferably PE, PP, PS, PVC, alpha-olefins, butadiene derivatives, Vestenamer® (Evonik),

- in technical thermoplastics, preferably PET, PMMA, PC, POM, PA, PBT, PEBA, TPU, PU, TPE, in high-performance thermoplastics, preferably PPS, PEEK, PES, PI, PEI, in copolymers,

- semi-finished products,

- in the automotive sector: electric drives, thermal management in battery systems, charging infrastructure in the vehicle and externally, electronics and power electronics, fuel cells, sensors, displays, cockpit, interactive surfaces, EMC shielding (electromagnetic shielding),

- Electronics and power electronics (connection),

- Connection and cooling of microchips, electronic components, displays, displays,

- Connection and cooling of LED headlights / spotlights, LEDs, area lighting,

- Connection and cooling of communication systems,

- Hydrogen technology and gas systems that require antistatic and gas tightness (gaskets, fuel cells, tanks, connectors, plugs, pipes / lines),

- Mineral oils, silicone oils, processing oils, vegetable oils, modified vegetable oils, motor, hydraulic and gear oils, greases, gels, phase change materials, for electrical and thermal conductivity and for reducing sliding friction.

The compositions preferably lead to at least one of the following effects in the aforementioned applications/materials:

- (improved) electrical conductivity,

- (improved) thermal conductivity,

- reduced friction,

- improved mechanics,

- increased scratch resistance,

- coloring / pigment,

- radiation absorption (UV),

- Antibacterial / antiviral effect,

- improved flame protection,

- reduced gas permeability. examples

Examples are given below which serve solely to illustrate the practice of this invention for those skilled in the art. They do not constitute any limitation of the claimed subject matter.

Dispersing agents (dispersing additives, in short: “additives”)

The following polyalkylene oxides corresponding to the stoichiometry given in Table 1 are prepared as dispersants according to the invention. The numerical values indicate the molar ratio of alkylene oxide (SO, PO, BO, EO) to starting alcohol. Additive 4 is therefore based on 1 mol SO, 2 mol BO, 8 mol PO, 0 mol EO in each case based on 1 mol hexan-1-ol. The synthesis from starter alcohol and the corresponding alkylene oxides takes place as described in EP 1078946 A1. The radical R ¹ of the additives in Table 1 is derived from the starting alcohol used in each case (for example, hexan-1-ol leads to R ¹ =hexyl). For all additives in Table 1 applies: R ² = H.

Table 1: Chemical composition of the dispersing additives 1 to 18 Dispersants that can be used according to the invention are additives 1 to 16. They contain aromatic radicals. Dispersants that cannot be used according to the invention are Additives 17 and 18 and Solsperse® 39000 (Lubrizol) and TEGOMER® DA 100 N (Evonik). These contain no aromatic residues.

fillers

graphs:

A graphene with the following properties was used as the graphene material: Dv50=20 pm (determined by laser diffraction), surface resistance <10 ohms/square (four-point test on a 25 pm film from the filter membrane), tap density ³ =0.251 like ^-3 (according to ASTM D7481).

Soot:

A carbon black which can be used to improve the electrical conductivity was used as a filler which cannot be used according to the invention. It is characterized by a DBP absorption (DBP = dibutyl phthalate) of 119ml/100g determined according to ASTM D 2414, a bulk density of 300 g/dm ³ determined according to ASTM D1513, a sieve residue of less than 250ppm in a 325 mesh sieve and a CTAB -Surface area (CTAB = cetyltrimethylammonium bromide) of 135m ² /g determined according to method ASTM D3765.

Production of pastes using the DISPERMAT ⁸¹ dissolver

In principle, the pastes are produced discontinuously (working in batches) using a suitable dispersing unit, a dissolver (DISPERMAT ^® Dissolver CV4-Plus, VMA-GETZMANN). The pastes are prepared in a 250 mL stainless steel container using a dissolver disc with a diameter of 40 mm. A batch size of 100 g paste is selected for a 250 mL stainless steel container. Depending on the experiment, a defined amount of the continuous phase (e.g. polyether polyol, polyester polyol, methyl methacrylate, polybutadiene diol, etc.) is placed in the stainless steel container. When using a dispersing additive, a defined amount of the additive is added to the continuous phase in relation to the amount of filler used (additive on pigment = AoP [%] ). “Pigment” or “filler” means the graphene material or carbon black. The following relationships apply between the mass of the continuous phase m _{kontl Phdse} the total mass of the composition m _total , the mass of the filler m _Fmstoff , the mass of the additive m _{Add ltlv} , the maximum degree of filling degree of filling _mdX , and the mass of the additive based on the Mass of the amount of filler AoP (additive on pigment, additive on pigment): The container with the continuous phase and the dispersing additive is clamped into the device on the DISPERMAT® dissolver and the agitator is shut down so that the dissolver disc is in the continuous phase but does not touch the bottom of the beaker. To prevent the dispersing additive from sinking to the bottom of the stainless steel container, the dispersing additive is stirred into the continuous phase for 1 minute at 750 rpm (rpm=revolutions per minute). The filler is added very slowly in portions. The stirrer is set between 750 rpm and 1000 rpm depending on the dust formation. The portionwise addition takes place over a period of approx. 5 minutes. After the addition is complete, the speed of the stirrer on the DISPERMAT ^® Dissolver is increased to 2000 rpm to 2500 rpm so that ideal dispersion can take place. This condition is maintained for another 5 minutes until the graphene-based paste is fully dispersed.

Visual assessment of the laaer stability of the paste

A test tube with a bottom diameter of 2.5 cm is filled with 40 g of paste and stored at room temperature for 12 h and 72 h and then examined. Another sample is stored for 72 h at 50 °C and then assessed. The assessment includes a visual assessment by 2 people for syneresis and paste appearance. In addition, the run-off of the paste is examined using a metal spatula. The following criteria apply to the assessment of "unstable" or "stable":

Unstable (Stability: "No"):

The paste forms at least 2mm of clear serum on the surface. The paste appears gritty. The paste does not run off the spatula homogeneously.

Stable (Stability: "Yes") ::

The paste forms less than 2mm of clear serum. The paste appears homogeneous and creamy. The paste runs off the spatula homogeneously. Viscosity - Rheological analysis of the pastes

The viscosities of the pastes are determined using a rheometer (Physica MCR 301/Anton Paar). The measuring body axis D-CP/PP7 without transponder (Anton Paar) is used for the examination, which is connected to a 25mm disposable measuring plate (disposable measuring plate D-PP25/ AL/S07 D:25mm/ Anton Paar). Before starting the measurement, the zero gap (here: 0.5 mm) is set. The following pastes are measured at this gap width. The rheometer is now ready for the measurement. A defined amount of the paste is placed on the rheometer plate and the preset measuring gap of 0.5 mm is adjusted. The excess paste is then removed from the edges (“the sample is trimmed”). Only now is the measurement started. A linear ramp is run with a shear rate of 0.1 s ^_1 to 1000 s ^_1 . The following conditions/parameters apply:

Data points: Specifications:

Quantity: 100 Size: g Shear rate

Duration: ramp linear Profile: ramp (linear)

Start value: 5 s Start value: 0.1 [1/s]

Final value: 1 s Final value: 1000 [1/s] For the graphic evaluation, the viscosity is plotted against the shear rate. The course of the curve of pastes with and without additive is then compared, for example. Often only the values at a shear rate of 1 s ^_1 and 10 s ^_1 are compared with each other. Hegman grindometer test

Devices used:

The Hegman grindometer is used to determine the dispersibility of particles or agglomerates in a liquid continuous phase. It does not determine the actual grain size or grain distribution.

The grindometer is a flat block of steel with two shallow, wedge-shaped grooves cut into its surface. These troughs run from a maximum depth at one end of the Grindometers evenly to the zero point at the other end of the steel block. The wedge depth can be read from the scales engraved on the side. The Hegman scale ranges from 0 to 8, with a higher Hegman number (Hegman value) indicating smaller particles. The following assignment of Hegman number and pm applies:

0 Hegman = 100 pm 4 Hegman = 50 pm 8 Hegman = 0 pm The cleaned and dry grindometer is placed on an even, non-slip surface. The paste to be examined is filled into the grooves of the grindometer at the deepest point. The paste must flow slightly over the edge of the groove. The squeegee is placed parallel to the short side of the grindometer at the deepest point of the grooves and quickly pulled perpendicular to the flat end of the groove of the grindometer. Immediately after the sample has been smeared, the grindometer is examined at a right angle to the long side and at an angle of 20° to 30° to its surface and held to the light in such a way that the surface structure of the paste in the groove becomes visible. The point at which a large number of particles or scratch marks from particles are visible in the channel for the first time is determined and the associated scale value (Hegman scale) is read off.

An early disturbance in the grooves (high Hegman number) means that the paste contains e.g. residual agglomerates or the filler (i.e. graphene material or soot) is poorly dispersed in the continuous phase and thus greater instability of the paste is to be expected and also with the other aforementioned disadvantages of an incompletely dispersed graphene in the end application.

The grindometer test is then evaluated as follows: Preparation of a graphene paste

The graphene pastes according to the following examples are produced as follows:

1. Place the continuous phase in a 250mL metal beaker.

2. Addition of the dispersing additive (100% AoP). Stir in briefly with a spatula so that the additive does not settle to the bottom.

3. Stir the additive into the continuous phase using a DISPERMAT® dissolver for approx. 1 minute at 750 rpm with a 40mm dispersing disc.

4. Slowly add the filler in portions over a period of approx. 5 minutes at 750 - 1000 rpm.

5. After the addition of the filler is complete, stirring is continued for 5 minutes at 2000-2500 rpm until the filler is completely dispersed.

Example 1: Pastes based on polyetherpolyol Desmophen®1110 BD (Covestro) is used as the continuous phase to produce the paste based on polyetherpolyol (see Tables 2 and 3): Table 2: Weights [g]

Table 3: Results nb = not determined, since the initial stability of the paste was not given and therefore homogeneous sampling for a viscosity determination was not possible or necessary.

Example 2: Pastes based on polyester polyol When producing a paste based on polyester polyol, Dynacoll® 7250 (Evonik) is used as the continuous phase (see Tables 4 and 5): Table 4: Weights [g]

Table 5: Results nb = not determined, since the initial stability of the paste was not given and therefore homogeneous sampling for a viscosity determination was not possible or necessary.

Example 3: Paste based on polybutadiene diol When producing a paste based on polybutadiene diol, Polyvest® HT (Evonik) is used as the continuous phase (see Tables 6 and 7): Table 6: Weights [g]

Table 7: Results nb = not determined, since the initial stability of the paste was not given and therefore homogeneous sampling for a viscosity determination was not possible or necessary.

Example 4: Epoxy-based paste When preparing an epoxy-based paste, Epikote® Resin 828 (Hexion) is used as the continuous phase (see Tables 8 and 9): Table 8: Weights [g]

Table 9: Results Hardened after 1 month of storage and can therefore no longer be used

Example 5: Pastes based on methyl methacrylate In the production of a paste based on methyl methacrylate, MERACRYL® MMA (raw material) is used as the continuous phase (see Tables 10 and 11): Table 10: Weight [g]

Table 11 : Results Hardened after 1 month of storage and can therefore no longer be used

Example 6: Pastes based on vegetable oil Castor oil is used as the continuous phase in the production of a paste based on vegetable oil (see Tables 12 and 13): Table 12: Weight [g]

Table 13: Results

Example 7: Pastes based on silyl-modified polymers (SMPs) in the production of a paste based on silyl-modified polymers (SMPs) TEGOPAC® RDS 1 used as the continuous phase (see Tables 14 and 15) Table 14: Weight [ G]

Table 15: Results nb = not determined, since the initial stability of the paste was not given and therefore homogeneous sampling for a viscosity determination was not possible or necessary. Only combinations of the polyalkylene oxides that can be used according to the invention and graphene material lead (regardless of the continuous phase) to compositions with high stability, low viscosity and good results in the Hegman grindometer test.

Claims

patent claims

1. Use of polyalkylene oxides which have at least one aromatic radical as a dispersant for graphene material.

2. Use according to claim 1, characterized in that the at least one aromatic radical is a phenyl radical.

3. Use according to claim 1 or 2, characterized in that the mass fraction of all aromatic residues based on the total mass of the dispersant is from 2% to 40%, preferably from 5% to 25%, in particular from 7% to 15%.

4. Use according to any one of claims 1 to 3, characterized in that the

Polyalkylene oxides have at least one unit of the formula -O-Chh-CHPh- or of the formula -CFh-CHPh-O-, where Ph is a phenyl radical.

5. Use according to any one of claims 1 to 4, characterized in that the

Polyalkylene oxides are selected from compounds of general formula (B),

R ¹ [0(S0)a(P0)b(B0)c(E0)dR ² ]n (B) where:

R ¹ is each independently selected from the group of n-bonded Ci-C2o-organyl radicals;

SO = styrene oxide,

PO = propylene oxide,

BO = butylene oxide,

6. The use as claimed in any of claims 1 to 5, characterized in that the polyalkylene oxides contain no further heteroatoms apart from oxygen and optionally nitrogen atoms.

7. Use according to one of claims 1 to 6, characterized in that the graphene material is a graphene material according to ISO-TS 80004-13, preferably selected from the group consisting of monolayer graphene, bilayer graphene, trilayer graphene, few -layer graphene, multi-layer graphene, one to ten layer graphene, epitaxial graphene, exfoliated graphene, graphene nanoribbons, graphene nanoplates, graphene nanoplatelets, graphene nanosheets, graphene microsheets, graphene nanoflakes, graphene quantum dots, graphene oxide, graphene oxide nanosheets, multi-layer graphene oxide and reduced graphene oxide and their mixtures.

8. Use according to any one of claims 1 to 7, characterized in that the graphene material is dispersed in a liquid continuous phase, the main component of which is selected from the group consisting of polyethers, in particular polyether polyols, polyesters, in particular polyester polyols, polycarbonates, in particular Polycarbonate polyols, polybutadienes, in particular polybutadiene polyols, epoxy resins, polysiloxanes, vegetable oils, mineral oils, synthetic organic oils, silyl-modified polymers, silyl-modified reactive diluents, (meth)acrylates, cyanoacrylates, dihydrolevoglucosenone (Cyrene®), dimethylformamide (DMF), organic carbonates, acetone, glycols, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), acetates, N-methyl-2-pyrrolidone (NMP), alcohols and dibasic esters (DBE).

9. A method for dispersing graphene material, characterized in that polyalkylene oxides are used as the dispersing agent, wherein the specifications according to any one of claims 1 to 8 apply.

10. The method according to claim 9, comprising the following, directly or indirectly consecutive, preferably immediately consecutive, process steps: a) submission of a continuous phase, preferably according to the specifications according to claim 8, b) addition of a dispersant, according to the specifications according to one of claims 1 to 6, c) adding and dispersing graphene material, preferably according to the specifications of claim 7.

11. The method according to claim 9, comprising the following, directly or indirectly consecutive, preferably immediately consecutive process steps: i) submission of a dispersing agent according to the specifications according to one of claims 1 to 6, j) addition and dispersing of graphene material, preferably according to the specifications according to claim 7.

12. A composition, preferably obtainable according to the method of claim 10, comprising or consisting of:

(a) a continuous phase, preferably according to the specifications of claim 8,

(b) a dispersing agent, according to the specifications of any one of claims 1 to 6, and (c) graphene material, preferably according to the specifications of claim 7.

13. Composition, preferably obtainable according to the method of claim 11, comprising or consisting of:

(i) a dispersant as defined in any one of claims 1 to 6, and

(j) graphene material, preferably according to the specifications of claim 7.

14. The composition of claim 12 or 13, characterized in that the mass fraction of component (c) or (j) based on the mass of the composition from 0.1% to 90%, preferably from 5% to 60%, in particular from 25% to 40% is 15. The composition according to claim 12 or 13, characterized in that the mass fraction of component (b) or (i) based on the mass of component (c) or (j) is 0.01% to 200%, preferably from 30% to 150%, especially 50% to 100%.