WO2023275135A1 - Polyalkylenoxide als dispergiermittel für graphen-material - Google Patents
Polyalkylenoxide als dispergiermittel für graphen-material Download PDFInfo
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- WO2023275135A1 WO2023275135A1 PCT/EP2022/067880 EP2022067880W WO2023275135A1 WO 2023275135 A1 WO2023275135 A1 WO 2023275135A1 EP 2022067880 W EP2022067880 W EP 2022067880W WO 2023275135 A1 WO2023275135 A1 WO 2023275135A1
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- WIPO (PCT)
- Prior art keywords
- graphene
- graphene material
- polyalkylene oxides
- specifications
- oxide
- Prior art date
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- 230000001419 dependent effect Effects 0.000 description 1
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- BNMYXGKEMMVHOX-UHFFFAOYSA-N dimethyl butanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC BNMYXGKEMMVHOX-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
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- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- BGSFCOHRQUBESL-UHFFFAOYSA-N ethyl prop-2-enyl carbonate Chemical compound CCOC(=O)OCC=C BGSFCOHRQUBESL-UHFFFAOYSA-N 0.000 description 1
- CYEDOLFRAIXARV-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound CCCOC(=O)OCC CYEDOLFRAIXARV-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/182—Graphene
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/182—Graphene
- C01B32/194—After-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/042—Graphene or derivatives, e.g. graphene oxides
Definitions
- 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.
- 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.
- 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
- 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).
- 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).
- 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.
- 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.
- graphene material dispersants that have at least one advantage over the prior art.
- these dispersants should allow high filling levels of graphene material and enable stable dispersions with low viscosities.
- 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.
- 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,
- Yet another object of the present invention is a composition comprising or consisting of:
- 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.
- 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 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.
- Range specifications include the range limits X and Y, unless otherwise stated.
- fragment includes compounds that are made up of at least two monomer units.
- 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.
- 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.
- polyalkylene oxides stands for a polyalkylene oxide or several polyalkylene oxides, preferably several polyalkylene oxides.
- 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.
- the at least one aromatic radical is a phenyl radical.
- the mass fraction of all aromatic residues 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.
- 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.
- 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
- 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.
- polyalkylene oxides are selected from compounds of general formula (C),
- 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,
- polyalkylene oxides are selected from compounds of the general formula (D),
- 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,
- 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
- SO styrene oxide
- EO ethylene oxide
- PO propylene oxide
- 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).
- 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
- 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.
- 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.
- 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.
- 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.
- 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).
- 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.
- polyglycerols can also be used as hydroxy-functional compounds R 1 (OH) n .
- R 2 comprises no SO moieties, no PO moieties, no BO moieties and no EO moieties.
- R 2 is preferably hydrogen (H).
- 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).
- the polyalkylene oxides can also comprise further heteroatoms, such as nitrogen atoms, for example.
- 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.
- 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.
- 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
- 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.
- 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 .
- the graphene material is in the form of granules, flakes, powder, films, layers, platelets, nanoribbons and/or fibers.
- 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
- 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.
- (meth)acrylic acid stands for methacrylic acid and/or acrylic acid.
- (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 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.
- the continuous phase contains a plasticizer selected from the group consisting of phthalates, citrates and adipates as the main component.
- the continuous phase contains a baking lacquer, e.g. based on silicone, as the main component.
- the continuous phase contains an unsaturated polyester resin (UPES) or vinyl ester resin as a main component.
- UPES unsaturated polyester resin
- vinyl ester resin vinyl ester resin
- 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.
- 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.
- 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.
- dissolver e.g. DISPERMAT® dissolver
- Ultra-Turrax e.g. DISPERMAT® dissolver
- Wet jet mill e.g. a high speed mixer
- conching machine e.g. a 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.
- 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.
- Yet another object of the present invention is a composition comprising or consisting of:
- 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.
- 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%.
- 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%.
- Yet another object of the present invention is a composition comprising or consisting of:
- 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.
- 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%.
- 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%.
- 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;
- 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
- viscosity modifiers include flow aids; defoamers; ionic liquids; wetting agents; and/or anti-scratch agents.
- 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.
- EMC electromagnetic shielding
- compositions according to the invention are also suitable as an additive for the following materials: elastomers, duroplastics, thermoplastics, thermoplastic elastomers.
- compositions according to the invention 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,
- thermoplastic 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,
- Gap filier 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),
- thermoplastics preferably PET, PMMA, PC, POM, PA, PBT, PEBA, TPU, PU, TPE, in high-performance thermoplastics, preferably PPS, PEEK, PES, PI, PEI, in copolymers,
- compositions preferably lead to at least one of the following effects in the aforementioned applications/materials:
- UV - radiation absorption
- Dispersing agents (dispersing additives, in short: “additives”)
- 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.
- DBP dibutyl phthalate
- CTAB cetyltrimethylammonium bromide
- 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.
- a defined amount of the continuous phase e.g. polyether polyol, polyester polyol, methyl methacrylate, polybutadiene diol, etc.
- the continuous phase e.g. polyether polyol, polyester polyol, methyl methacrylate, polybutadiene diol, etc.
- additive on pigment AoP [%] ).
- Filler means the graphene material or carbon black.
- 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.
- 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.
- 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.
- 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”:
- 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.
- 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).
- the zero gap here: 0.5 mm
- 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:
- 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:
- 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.
- 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 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 filler i.e. graphene material or soot
- 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]
- Example 2 Pastes based on polyester polyol
- Dynacoll® 7250 (Evonik) is used as the continuous phase (see Tables 4 and 5): Table 4: Weights [g]
- Example 3 Paste based on polybutadiene diol
- Polyvest® HT Evonik
- Table 6 Weights [g]
- Example 4 Epoxy-based paste
- Epikote® Resin 828 Hydrophilicity
- Table 8 Weights [g]
- Example 5 Pastes based on methyl methacrylate
- MERACRYL® MMA raw material
- Table 10 Weight [g]
- 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]
- 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]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Carbon And Carbon Compounds (AREA)
Abstract
Description
Claims
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KR1020247003490A KR20240027790A (ko) | 2021-07-02 | 2022-06-29 | 그래핀 물질을 위한 분산제로서의 폴리알킬렌 옥시드들 |
CN202280047218.5A CN117597306A (zh) | 2021-07-02 | 2022-06-29 | 作为石墨烯材料的分散剂的聚环氧烷 |
CA3224256A CA3224256A1 (en) | 2021-07-02 | 2022-06-29 | Polyalkylene oxides as dispersants for graphene material |
EP22740830.9A EP4363374A1 (de) | 2021-07-02 | 2022-06-29 | Polyalkylenoxide als dispergiermittel für graphen-material |
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KR (1) | KR20240027790A (de) |
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CN116281989A (zh) * | 2023-04-12 | 2023-06-23 | 江西省科学院应用化学研究所 | 一种龙脑樟活性分子改性修饰石墨烯薄膜及其制备方法 |
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EP1078946A1 (de) | 1999-08-27 | 2001-02-28 | Goldschmidt AG | Durch Alkoxylierung erhaltene blockcopolymere, styrenoxidhaltige Polyalkylenoxide und deren Verwendung |
WO2004044035A1 (de) * | 2002-11-12 | 2004-05-27 | Clariant Gmbh | Styroloxidhaltige copolymere und deren verwendung als emulgatoren und dispergiermittel |
WO2012059489A1 (de) | 2010-11-05 | 2012-05-10 | Evonik Goldschmidt Gmbh | Zusammensetzung aus polymeren und elektrisch leitfähigem kohlenstoff |
CN104194461A (zh) * | 2014-08-14 | 2014-12-10 | 济南圣泉集团股份有限公司 | 一种改性石墨烯及其制备方法,以及一种水性防静电环氧地坪涂料及其制备方法 |
WO2020173821A1 (en) * | 2019-02-26 | 2020-09-03 | Byk-Chemie Gmbh | Composition comprising a comb copolymer |
-
2022
- 2022-06-29 CA CA3224256A patent/CA3224256A1/en active Pending
- 2022-06-29 CN CN202280047218.5A patent/CN117597306A/zh active Pending
- 2022-06-29 TW TW111124324A patent/TW202311355A/zh unknown
- 2022-06-29 EP EP22740830.9A patent/EP4363374A1/de active Pending
- 2022-06-29 WO PCT/EP2022/067880 patent/WO2023275135A1/de active Application Filing
- 2022-06-29 KR KR1020247003490A patent/KR20240027790A/ko unknown
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EP1078946A1 (de) | 1999-08-27 | 2001-02-28 | Goldschmidt AG | Durch Alkoxylierung erhaltene blockcopolymere, styrenoxidhaltige Polyalkylenoxide und deren Verwendung |
WO2004044035A1 (de) * | 2002-11-12 | 2004-05-27 | Clariant Gmbh | Styroloxidhaltige copolymere und deren verwendung als emulgatoren und dispergiermittel |
WO2012059489A1 (de) | 2010-11-05 | 2012-05-10 | Evonik Goldschmidt Gmbh | Zusammensetzung aus polymeren und elektrisch leitfähigem kohlenstoff |
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Cited By (2)
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CN116281989A (zh) * | 2023-04-12 | 2023-06-23 | 江西省科学院应用化学研究所 | 一种龙脑樟活性分子改性修饰石墨烯薄膜及其制备方法 |
CN116281989B (zh) * | 2023-04-12 | 2024-02-13 | 江西省科学院应用化学研究所 | 一种龙脑樟活性分子改性修饰石墨烯薄膜及其制备方法 |
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CN117597306A (zh) | 2024-02-23 |
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EP4363374A1 (de) | 2024-05-08 |
CA3224256A1 (en) | 2023-01-05 |
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