WO2023061579A1 - ELEKTRISCH LEITFÄHIGE SILICONZUSAMMENSETZUNG MIT KOHLENSTOFFNANORÖHREN UND RUß - Google Patents
ELEKTRISCH LEITFÄHIGE SILICONZUSAMMENSETZUNG MIT KOHLENSTOFFNANORÖHREN UND RUß Download PDFInfo
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- WO2023061579A1 WO2023061579A1 PCT/EP2021/078323 EP2021078323W WO2023061579A1 WO 2023061579 A1 WO2023061579 A1 WO 2023061579A1 EP 2021078323 W EP2021078323 W EP 2021078323W WO 2023061579 A1 WO2023061579 A1 WO 2023061579A1
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- WIPO (PCT)
- Prior art keywords
- electrically conductive
- weight
- carbon
- silicone elastomer
- carbon black
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- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229920002050 silicone resin Chemical group 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/24—Conductive material dispersed in non-conductive organic material the conductive material comprising carbon-silicon compounds, carbon or silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08K3/041—Carbon nanotubes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/70—Additives characterised by shape, e.g. fibres, flakes or microspheres
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N30/00—Piezoelectric or electrostrictive devices
- H10N30/01—Manufacture or treatment
- H10N30/06—Forming electrodes or interconnections, e.g. leads or terminals
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N30/00—Piezoelectric or electrostrictive devices
- H10N30/01—Manufacture or treatment
- H10N30/06—Forming electrodes or interconnections, e.g. leads or terminals
- H10N30/067—Forming single-layered electrodes of multilayered piezoelectric or electrostrictive parts
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N30/00—Piezoelectric or electrostrictive devices
- H10N30/80—Constructional details
- H10N30/87—Electrodes or interconnections, e.g. leads or terminals
- H10N30/877—Conductive materials
- H10N30/878—Conductive materials the principal material being non-metallic, e.g. oxide or carbon based
-
- 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
Definitions
- the invention relates to electrically conductive, crosslinking silicone elastomer compositions, a process for their production and their use as electrically conductive printing ink in non-contact printing processes for the production of electrodes for sensors, actuators or EAP layer systems.
- Electrically conductive printing inks are used for the production of printed electronics in order to apply electrodes in electronic components over a large area or in a structured manner to a substrate using any desired printing process.
- the printing of electrically conductive elastomers onto an elastic carrier (such as e .g . silicone, TPU) enables the construction of fully or partially elastic electronic components that retain their electrical properties almost unchanged even when stretched or compressed .
- electrically conductive elastomeric inks can be printed on flexible (but not stretchable) substrates such as B.
- Conductive printing inks for printed electronics are known and some are also commercially available. They typically contain at least one polymeric binder, at least one conductive component such as e.g. B. Metal or carbon particles and at least one solvent for adjusting the viscosity. Basically, conductive carbon particles such as B.
- Carbon black and carbon nanotubes (CNT) as fillers have the disadvantage that they greatly increase the viscosity of the formulation, which reduces the printability of the ink significantly more difficult, so that solvents are typically used for dilution in order to reduce the effective concentration of the particles in the printing ink and thus make the printing ink applicable.
- US2016351289 describes that a solvent content of at least 10% must be contained in a silicone-based conductive printing ink so that it can be applied.
- organic solvents are used in the field of silicone printing inks, which are very difficult to completely remove afterwards and entail high costs for the user in terms of occupational safety and environmental protection.
- carbon black is usually added to a CNT-containing formulation, as this typically causes a less pronounced increase in viscosity than CNTs do, improves the conductivity of the electrode and ensures a more homogeneous charge distribution in the electrode of the final component.
- CNT-containing formulation For highly conductive materials with a low specific resistance ⁇ 10 - 100 ohm* cm, carbon blacks are typically used, which are characterized by a high surface area and structure. Typically, as the surface area increases, soot conductivity increases. BET measurements of high-conductivity carbon black typically result in values > 800 m2/g. A typical example of this is Ketj enblack EC 600JD (BET 1400 m 2 /g).
- Carbon blacks with smaller surface areas (BET ⁇ 300 m2/g) must be used in a larger proportion by volume and mass of the overall formulation and result in lower electrical conductivity. Furthermore, > 20% by weight of carbon black is typically required so that the specific resistance falls well below 100 Qcm
- Solids content based on a silicone elastomer, carbon black as well CNT the latter being characterized as being at least 30 nm thick.
- the latter property gives the solvent-based, conductive printing ink good printability in screen printing, which is not possible with thin CNTs ( ⁇ 30 nm).
- the high-conductivity carbon black Ketjenblack EC300J is used (manufacturer information: BET 800 m2/g; OAN 310-345 ml/100g).
- the printing ink described in US9253878 has very good electrical conductivity ⁇ 1 Ohm*cm.
- CNT-containing silicone elastomers are known. Silicone elastomers containing both CNT and carbon black are described in CN103160128. The silicone elastomers described here are characterized by a high proportion of carbon black. The carbon black is also characterized by a high surface area (BET 1400-1500 m 2 /g). At least 3.7% by weight of carbon black is claimed, but the examples show that a total filler content (CB + CNT) of at least 8.5% is necessary to obtain good electrical properties, so that the specific resistance is ⁇ 20 Ohm*cm. No printing process using these compositions is disclosed.
- CB + CNT total filler content
- the high aspect ratio of the conductive particles ensures that the conductive particles, in contrast to spherical particles, can form a conductive network through the entire system with lower amounts of filler, which also persisted when the elastomer was stretched. This ensures good electron conduction even when the elastomer is stretched.
- WO 2009/153192 A2 describes, for example, a method for producing conductive layers on semiconductor structures, a metal powder dispersion being applied to a carrier and being detached from the carrier onto a target by a laser beam.
- WO 2010/069900 A1 describes, for example, laser transfer printing of color.
- WO 2015/181810 A1 describes a laser transfer method for printing metallic bodies.
- a metal film on a transparent substrate is heated at specific points and positioned in the form of drops.
- the object of the present invention was to provide electrically conductive, crosslinking silicone elastomer compositions with a specific resistance of ⁇ 10 ohms * cm, which manages with small amounts of carbon black in combination with CNT, but without the use of solvents, but at the same time have good application properties Printing ink in non-pressurized application processes such as e.g. shows the laser transfer printing process.
- the viscosity of the silicone elastomer composition according to the invention is a maximum of 60 at a shear rate of 10 s ⁇ 1. 000 mPas . It can therefore be used as a printing ink without the addition of a solvent in order to print electrodes for dielectric elastomer sensors, actuators and generators. Furthermore, the expansion factor of the relative increase in resistance R/Ro is reduced.
- the subject matter of the invention is therefore an electrically conductive, crosslinking silicone elastomer composition containing: -0.5 to 3.0% by weight carbon black with a maximum BET surface area of 300 m 2 /g,
- Carbon Nanotubes CNT
- addition-crosslinking, peroxide-crosslinking, condensation-crosslinking, or radiation-crosslinking silicone elastomer compositions can be used.
- Peroxidic or addition-crosslinking compositions are preferred.
- Addition-crosslinking compositions are particularly preferred.
- the silicone elastomer compositions can be formulated in one or two parts.
- the silicone elastomer compositions are crosslinked by supplying heat, UV light and/or moisture.
- the following silicone elastomer compositions are suitable, for example: HTV (addition-crosslinking), HTV (radiation-crosslinking), LSR, RTV 2 (addition-crosslinking), RTV 2 (condensation-crosslinking), RTV 1, TPSE (thermoplastic silicone elastomer), thiol-ene and
- the preferred addition-crosslinking silicone elastomer compositions contain
- (B) at least one linear organopolysiloxane compound having Si-bonded hydrogen atoms, or instead of (A) and (B) or in addition to (A) and (B) (C) at least one linear organopolysiloxane compound having Si-C-bonded radicals with aliphatic carbon-carbon multiple bonds and Si-bonded hydrogen atoms, and
- the silicone compositions can be one-component silicone compositions as well as two-component silicone compositions.
- the two components of the compositions according to the invention can contain all of the ingredients in any combination, generally with the proviso that one component does not simultaneously contain siloxanes with aliphatic multiple bonds, siloxanes with Si-bonded hydrogen and catalyst, i.e. essentially not simultaneously the components ( A) , (B) and
- the compounds (A) and (B) or (C) used in the compositions according to the invention are selected in such a way that crosslinking is possible.
- compound (A) has at least two aliphatically unsaturated radicals and (B) at least three Si-bonded hydrogen atoms
- compound (A) has at least three aliphatically unsaturated radicals and siloxane (B) has at least two Si-bonded hydrogen atoms
- siloxane (C) is used which has aliphatically unsaturated radicals and Si-bonded hydrogen atoms in the ratios mentioned above.
- the compound (A) used according to the invention can be silicon-free organic compounds preferably having at least two aliphatically unsaturated groups and organosilicon compounds preferably having at least two aliphatically unsaturated groups, or mixtures thereof.
- silicon-free organic compounds (A) are examples of silicon-free organic compounds (A).
- the silicone compositions according to the invention preferably contain at least one aliphatically unsaturated organosilicon compound as component (A), it being possible to use all aliphatically unsaturated organosilicon compounds previously used in addition-crosslinking compositions, such as, for example, silicone block copolymers Urea segments, silicone block copolymers with amide segments and/or imide segments and/or ester-amide segments and/or polystyrene segments and/or silarylene segments and/or carborane segments and silicone graft copolymers with ether - Groups .
- silicone block copolymers Urea segments
- silicone block copolymers with amide segments and/or imide segments and/or ester-amide segments and/or polystyrene segments and/or silarylene segments and/or carborane segments and silicone graft copolymers with ether - Groups such as, for example, silicone block copolymers Urea segments, silicone block copolymers with amide segments and/or
- organosilicon compounds (A) which have Si-C-bonded radicals with aliphatic carbon-carbon multiple bonds are preferably linear or branched organopolysiloxanes composed of units of the general formula (I)
- R 4 independently of one another, identical or different, is an organic or inorganic radical free from aliphatic carbon-carbon multiple bonds
- R 5 independently, identically or differently, is a monovalent, substituted or unsubstituted, Si-C- bonded hydrocarbon radical having at least one aliphatic carbon to ff -carbon to ff multiple bond, a is 0, 1, 2 or 3, and b is 0 , 1 or 2, with the proviso that the sum of a + b is less than or equal to 3 and at least 2 radicals R 5 are present per molecule.
- the radical R 4 can be monovalent or polyvalent radicals, the polyvalent radicals, such as bivalent, trivalent and tetravalent radicals, then several such as about two, three or four siloxy moieties of formula (I) join together.
- R 4 are the monovalent radicals -F, -CI, -Br, -OR 6 , -CN, -SCN, -NCO and Si-C-bonded, substituted or unsubstituted hydrocarbon radicals which atoms with oxygen or of the group -C(O)- can be interrupted, as well as divalent radicals Si- bonded on both sides according to formula (I).
- radical R 4 is a Si—C-bonded, substituted hydrocarbon radical
- preferred substituents are halogen atoms, phosphorus radicals, cyano radicals, -OR 6 , -NR 6 -, -NR 6 2 , -NR 6 -C ( 0) -NR 6 H 2, -C(O)-NR 6 H 2 , -C(O)R 6 , -C(O)OR 6 , -SO 2 -Ph and -CgFs.
- R 6 are independently, identically or differently, a hydrogen atom or a monovalent hydrocarbon radical having 1 to 20 carbon atoms and Ph is the phenyl radical.
- radicals R 4 are alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl , neo-pentyl, tert-pentyl, hexyl, such as n-hexyl, heptyl, such as n-heptyl, octyl, such as n-octyl and iso-octyl, such as 2, 2, 4-trimethylpentyl, nonyl, such as the n-nonyl radical, decyl radicals such as the n-decyl radical, dodecyl radicals such as the n-dodecyl radical, and octadecyl radicals such as the n-octadecyl radical, cycloalkyl radicals such as
- substituted radicals R 4 are haloalkyl radicals, such as the 3, 3, 3-trifluoro-n-propyl radical, the 2, 2, 2, 2', 2', 2'-hexafluoroisopropyl radical, the heptafluoroisopropyl radical, haloaryl radicals, such as the above -, m- and p-chlorophenyl radical , - (CH 2 )- N (R 6 ) c (o) NR 6 2 , - (CH 2 ) n -c (O) NR 6 2 , - (CH 2 ) O - C(0) R6 , -( CH2 ) O -C(0) OR6 , -( CH2 ) O -C(0) NR6H2 , -( CH2 )-C(0)-( CH2 ) P C (0) CH 3 , -(CH 2 ) -O-CO-R 6 , -(CH 2 )-NR 6 ,
- R 4 identically divalent radicals Si-bonded on both sides according to formula (I) are those which are derived from the monovalent examples given above for radical R 4 in that an additional bond takes place by substitution of a hydrogen atom
- examples of such radicals are - (CH 2 )-, -CH(CH 3 )-, -C(CH 3 ) 2 -, -CH(CH 3 )-CH 2 - , -C 6 H 4 -, -CH (Ph)-CH 2 - , -C(CF 3 ) 2 -, - (CH 2 ) O -C 6 H 4 - (CH 2 ) o -, - (CH 2 ) O - C 6 H 4 -C 6 H 4 - (CH 2 ) o -, - (CH 2 O) P , (CH 2 CH 2 O) O , - (CH 2 ) 0 -O X -C 6 H 4 -SO 2 -C 6 H 4 -O X
- the radical R 4 is preferably a monovalent, Si-C-bonded, optionally substituted hydrocarbon radical having 1 to 18 carbon atoms, free from aliphatic carbon-carbon multiple bonds, particularly preferably a monovalent, from aliphatic carbon-carbon Multiple bond-free, Si-C-bonded hydrocarbon radical having 1 to 6 carbon atoms, in particular around the methyl or phenyl radical.
- the radical R 5 from formula (I) can be any group accessible to an addition reaction (hydrosilylation) with a SiH-functional compound. If the radical R 5 is a Si—C-bonded, substituted hydrocarbon radical, the preferred substituents are halogen atoms, cyano radicals and —OR 6 , where R 6 has the meaning given above.
- the radical R 5 is preferably an alkenyl and alkynyl group having 2 to 16 carbon atoms, such as vinyl, allyl, methallyl, 1-propenyl, 5-hexenyl, ethynyl, butadienyl, hexadienyl, Cyclopentenyl, cyclopentadienyl, cyclohexenyl, vinylcyclohexylethyl, divinylcyclohexylethyl, norbornenyl, vinylphenyl and styryl radicals, particular preference being given to using vinyl, allyl and hexenyl radicals.
- alkenyl and alkynyl group having 2 to 16 carbon atoms such as vinyl, allyl, methallyl, 1-propenyl, 5-hexenyl, ethynyl, butadienyl, hexadienyl, Cyclopentenyl, cyclopentadieny
- component (A) can vary within wide limits, for example between 10 2 and 10 6 g/mol.
- component (A) can be a relatively low molecular weight alkenyl-functional oligosiloxane, such as 1,2-divinyltetramethyldisiloxane, but it can also be a high polymer polydimethylsiloxane having chain or terminal Si-bonded vinyl groups, e.g. B. with a molecular weight of 10 5 g/mol (number average determined by NMR).
- the structure of the molecules forming component (A) is also not specified;
- the structure of a relatively high molecular weight, ie oligomeric or polymeric, siloxane can be linear, cyclic, branched or else resinous or network-like.
- Linear and cyclic polysiloxanes are preferably composed of units of the formula R 4 3SiOi/2, R 5 R 4 2SiOi/2, R 5 R 4 SiOi/2 and R 4 2SiC>2/2, where R 4 and R 5 are the ones given above have meaning .
- Branched and network polysiloxanes also contain trifunctional and/or tetrafunctional units, preference being given to those of the formulas R 4 SiO3/2, R 5 SiO3/2 and SiC>4/2. It is of course also possible to use mixtures of different siloxanes which meet the criteria for component (A).
- component (A) is the use of vinyl-functional, essentially linear polydiorganosiloxanes having a viscosity of from 0.01 to 500,000 Pa ⁇ s, particularly preferably from 0.1 to 100,000 Pa ⁇ s, in each case at 25° C., measured according to DIN EN ISO 3219: 1994 and DIN 53019 using a calibrated rheometer with a cone and plate system, cone CP50-2 with an included angle of 2° and a shear rate of 1 s -1 .
- organosilicon compounds (B) All hydrogen-functional organosilicon compounds which have also previously been used in addition-crosslinkable compositions can be used as organosilicon compounds (B).
- organopolysiloxanes (B) which have Si-bonded hydrogen atoms preferably linear, cyclic or branched organopolysiloxanes from units of the general formula (III)
- R 4 has the meaning given above, c is 0,1, 2 or 3 and d is 0, 1 or 2, with the proviso that the sum of c+d is less than or equal to 3 and there are at least two Si-bonded hydrogen atoms per molecule.
- the organopolysiloxane (B) used according to the invention preferably contains Si-bonded hydrogen in the range from 0.04 to 1.7 percent by weight, based on the total weight of the organopolysiloxane (B).
- component (B) can also vary within wide limits, for example between 10 2 and 10 6 g/mol.
- component (B) can be a relatively low molecular weight SiH-functional oligosiloxane, such as tetramethyldisiloxane, but also a high polymer polydimethylsiloxane having chain or terminal SiH groups, or a silicone resin having SiH groups.
- the structure of the molecules forming component (B) is also not specified;
- the structure of a relatively high molecular weight, ie oligomeric or polymeric, SiH-containing siloxane can be linear, cyclic, branched or else resinous or network-like.
- Linear and cyclic polysiloxanes (B) are preferably composed of units of the formula R 4 3SiOi/2, HR 4 2SiOi/2, HR 4 SiC>2/2 and R 4 2SiC>2/2, where R 4 has the meaning given above .
- Branched and network-like polysiloxanes additionally contain trifunctional and/or tetrafunctional units, preference being given to those of the formulas R 4 SiC>3/2, HSiOs/2 and SiC>4/2, where R 4 has the meaning given above.
- component (B) Mixtures of different siloxanes that meet the criteria for component (B) can of course also be used be used.
- the molecules forming component (B) can optionally also contain aliphatically unsaturated groups in addition to the obligatory SiH groups.
- Particular preference is given to using low molecular weight SiH-functional compounds such as tetrakis(dimethylsiloxy)silane and tetramethylcyclotetrasiloxane, and higher molecular weight SiH-containing siloxanes such as poly(hydrogenmethyl)siloxane and
- Constituent (B) is preferably present in the crosslinkable silicone compositions of the invention in such an amount that the molar ratio of SiH groups to aliphatically unsaturated groups from (A) is from 0.1 to 20, particularly preferably from 0.3 to 2.0 .
- the components (A) and (B) used according to the invention are commercially available products or can be prepared by conventional processes.
- the silicone compositions according to the invention can contain organopolysiloxanes (C) which simultaneously contain aliphatic carbon-carbon
- the silicone compositions according to the invention can also contain all three components (A), (B) and (C). If siloxanes (C) are used, they are preferably those composed of units of the general formulas (IV), (V) and (VI)
- R 4 and R 5 have the meaning given above f is 0, 1, 2 or 3, g is 0, 1 or 2 and h is 0, 1 or 2, with the proviso that per molecule there are at least two radicals R 5 and at least two Si-bonded hydrogen atoms are present.
- organopolysiloxanes (C) are those composed of SiO 4 /2, R 4 3 SiOi / 2, R 4 2R 5 SiOi / 2 and R 4 2HSiOi / 2 units, so-called MQ resins, these resins additionally R 4 SiO 3 /2 and R 4 2SiO units may contain, and linear organopolysiloxanes consisting essentially of R 4 2R 5 SiOi / 2, R 4 2SiO and R 4 HSiO units with R 4 and R 5 have the same meaning as above .
- the organopolysiloxanes (C) preferably have an average viscosity of 0.01 to 500,000 Pas, particularly preferably 0.1 to 100,000 Pas, in each case at 25° C., measured according to DIN EN ISO 3219: 1994 and DIN 53019 using a calibrated Rheometer with a cone and plate system, cone CP50-2 with an included angle of 2° and a shear rate of 1 s- 1 .
- Organopolysiloxanes (C) are commercially available or can be prepared using customary methods.
- Addition-crosslinking silicone compositions according to the invention can be selected from the group comprising
- (D) mean a hydrosilylation catalyst.
- the silicone composition usually contains 30-95% by weight, preferably 30-80% by weight and particularly preferably 40-70% by weight of (A), based on the total mass of the silicone composition.
- the silicone composition usually contains 0.1-60% by weight, preferably 0.5-50% by weight and particularly preferably 1-40% by weight of (B), based on the total mass of the silicone composition.
- the silicone composition contains component (C), there are usually 30-95% by weight, preferably 30-80% by weight, particularly preferably 40-70% by weight, of (C) in the formulation included, based on the total mass of the silicone composition.
- the amount of component (D) can be between 0.1 and 1000 parts per million (ppm), 0.5 and 100 ppm, or 1 and 50 ppm of the platinum group metal, depending on the total weight of the components.
- the amounts of all the components present in the silicone composition are chosen so that they add up to 100% by weight. % based on the total weight of the silicone composition.
- Component (D) can be a platinum group metal, for example platinum, rhodium, ruthenium, palladium, osmium or iridium, an organometallic compound or a combination thereof.
- component (D) are compounds such as hexachloroplatinic(IV) acid, platinum dichloride, platinum acetylacetonate and complexes of said compounds encapsulated in a matrix or a nucleus shell-like structure.
- the low molecular weight platinum complexes of organopolysiloxanes include 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane complexes with platinum. Further examples are platinum phosphite complexes, platinum phosphine complexes or alkyl platinum complexes. These compounds can be encapsulated in a resin matrix.
- the concentration of component (D) is sufficient to catalyze the hydrosilylation reaction of components (A) and (B) upon exposure to generate the heat required in the process described herein.
- the amount of Component (D) can be between 0.1 and 1000 parts per million (ppm), 0.5 and 100 ppm, or 1 and 50 ppm of the platinum group metal, depending on the total weight of the components.
- the cure rate may be low when the platinum group metal component is below 1 ppm. Using more than 100 ppm of the platinum group metal is uneconomical or may reduce the stability of the adhesive formulation.
- CNT refers to carbon nanotubes, also known as carbon nanotubes. These are nanomaterials that have the shape of hollow cylinders and consist of hexagonal carbon structures. The person skilled in the art is not restricted in his choice of CNTs; he can use any CNTs that are commercially available or can be produced using methods known from the literature.
- the CNTs are used in a content in the range from 0.1-5% by weight, based on the total weight of the composition; a content in the range from 0.1-3% by weight is preferred.
- CNTs with an average diameter of 1-50 nm and an aspect ratio (ratio of length to diameter L/B) of 10-10,000 are preferably used.
- SWCNTs single-walled carbon nanotubes
- MWCNTs multi-walled carbon nanotubes
- Carbon blacks can be used in all available and known modifications, such as furnace, thermal, gas, channel and acetylene blacks. Of course, mixtures of different carbon blacks can also be used. According to the invention, carbon blacks are used which have a maximum BET surface area of 300 m2/g according to ASTM D6556.
- the carbon black content is preferably 0.5 to 20% by weight and particularly preferably 0.5 to 3.0% by weight, based on the total weight of the silicone elastomer composition according to the invention.
- the masses described can optionally contain all other additives which are known to the person skilled in the art for addition-crosslinkable compositions from the prior art.
- additives can be, for example, rheological additives, inhibitors, light stabilizers, flame retardants, dispersants, heat stabilizers, etc.
- Another object of the present invention is the production of the inventive electrically conductive, crosslinking silicone elastomer composition, characterized in that a) in IK systems, all components are mixed in one or more steps and then pressure filtration through a metal mesh with a maximum mesh size 200 ⁇ m, or that b) in the case of 2K systems only the components of the A or B composition are mixed in one or more steps and then pressure filtration of the A or B composition through a metal mesh with a mesh size of at most 200 ⁇ m.
- the metal mesh used in the pressure filtration preferably has a mesh size of at most 100 ⁇ m.
- the methods for mixing the components and for the pressure filtration and the apparatus which can be used therein are sufficiently known to the person skilled in the art from the prior art.
- the dispersion takes place, for example, with a roll mill, kneader or, in particular, a dissolver (high-speed mixer), a scraper usually being used in addition in order to achieve uniform distribution of the conductive fillers.
- a planetary dissolver with scraper is preferably used.
- a vacuum planetary dissolver with scraper and paddle stirrer is particularly preferably used.
- Dissolver discs with any arrangement and number of teeth can be used.
- the filter mesh does not clog when a paste containing particles with a high aspect ratio (L/W > 10) is passed through it.
- the filtration step would have a negative impact on the electrical properties of the material. This is not the case: both the electrical resistance of the uncrosslinked printing ink and the electrical behavior of the vulcanized sample under elongation remain constant.
- a further object of the invention is the use of the conductive crosslinking silicone elastomer composition according to the invention as an electrically conductive printing ink in non-contact printing processes for the production of electrically conductive elastomers on elastic carriers.
- the electrically conductive, crosslinking silicone elastomer composition according to the invention is used as a printing ink, e.g. used in a contactless printing process, this creates a Printed image that has a smooth surface that is free of jags.
- This is of decisive advantage if multi-layer systems are to be produced in which the conductive material is to be introduced between further layers, eg by lamination or overlaying.
- the electrically conductive, crosslinking silicone elastomer composition according to the invention can be used as a printing ink for other non-contact printing processes such as, for example, spray, drop-on-demand processes or laser transfer printing (LIFT processes). It is preferably used in laser transfer printing (LIFT process).
- the electrically conductive, crosslinking silicone elastomer composition according to the invention is particularly preferably suitable as a printing ink for printing electrodes for dielectric elastomer sensors, actuators and generators and EAP layer systems.
- a further subject of the invention is therefore electrically conductive films with a layer thickness of at most 200 ⁇ m, produced from electrically conductive, crosslinking silicone elastomer composition containing:
- CNT carbon nanotubes
- Another subject of the invention are therefore electrically conductive films made from electrically conductive, crosslinking silicone elastomer composition containing: 0.5 to 3.0% by weight of carbon black with a maximum BET surface area of 300 m 2 / g,
- CNT carbon nanotubes
- the electrically conductive films with a maximum layer thickness of 200 gm are produced from an electrically conductive, crosslinking silicone elastomer composition containing:
- the electrically conductive films preferably exhibit an elongation factor of the relative increase in resistance R/Ro of less than or equal to 1.5.
- Example 1 The examples below were carried out at a pressure of the surrounding atmosphere, ie at about 1013 hPa, and at room temperature, ie about 23° C. or a temperature which occurs when the reactants combine at room temperature without additional heating or cooling.
- a pressure of the surrounding atmosphere ie at about 1013 hPa
- room temperature ie about 23° C. or a temperature which occurs when the reactants combine at room temperature without additional heating or cooling.
- Carbon black A Birla Conductex 7055 Ultra (BET 55 g/m 2 , OAN 170 cm 3 / 100g).
- Carbon black B Ensaco 260G (BET 68 g/m 2 , OAN 190 mL/100 g)
- Carbon Black C Ketjenblack EC-600JD (available from Nouryon, BET 1400 g/m 2 , OAN 495 cm 3 /100g).
- the BET measurement was carried out using gas adsorption with nitrogen in accordance with ASTM D6556.
- the OAN values are specified by the manufacturer.
- ViPo 1,000 Vinyldimethylsiloxy-terminated polydimethylsiloxane with a viscosity of 1,000 mPa*s, available from Gelest Inc. under the product designation DMS-V31 (Gelest catalogue).
- HPo 1000 Hydridodimethylsiloxy-terminated polydimethylsiloxane having a viscosity of 1000 mPa*s, available from Gelest Inc. under the product designation DMS-H31 (Gelest catalogue).
- An a,w-dimethylhydrogensiloxypoly(dimethylmethylhydrogen)siloxane (viscosity 130-200 mm 2 /s; 0.145-0.165% by weight H) was used as the crosslinking agent.
- a platinum complex with phosphite ligands was chosen as the hydrosilylation catalyst for one-component systems, as described in EP2050768B1 (catalyst 6).
- the viscosity measurements were carried out on an air-bearing MCR 302 rheometer from Anton Paar at 25.degree. A cone and plate system (25 mm, 2°) with a gap of 105 ⁇ m was used. The excess material was removed (trimmed) with a spatula at a gap spacing of 115 pm. The cone then moved to 105 pm slit spacing so that the entire slit is filled. Before each measurement, a "pre-shear" is performed, in which the shear history is erased by sample preparation, plotting, and trimming. Pre-shear occurs for 60 seconds at a shear rate of 10 s -1 , followed by a rest period of 300 seconds.
- the shear viscosity is determined using a step profile in which the sample is sheared at a constant shear rate of 1 s -1 , 10 s -1 and 100 s -1 for 100 seconds each. A reading is recorded every 10 seconds, resulting in 10 readings per shear rate. The mean value from these 10 measurement points gives the shear viscosity at the respective shear rate.
- the storage modulus G' was determined by means of an amplitude test. In this oscillation test, the amplitude y is varied from 0.01 to 1000% (with a circle frequency w of 10 s -1 , logarithmic ramp , 30 measuring points ) . Typically, the linear viscoelastic (LVE) range is found at low amplitude values, in which G′, when plotted over y as a double logarithm, has a plateau value. The plateau value is the storage modulus G' to be determined.
- LVE linear viscoelastic
- the contact resistance is not measured, since the current is applied to two contacts and the voltage U of the current I v that has already flowed through the sample is measured at two other contacts.
- the resistance R of uncured siloxanes is measured using the Model 2110 5 digit measured by Keithley Instrument and a measuring apparatus made from PP natural and stainless steel (1.4571) electrodes.
- the measuring device is connected to the electrodes by means of brass contacts and laboratory cables.
- the measuring apparatus is a mold with defined dimensions for L ⁇ W ⁇ H of 16 cm ⁇ 3 cm ⁇ 0.975 cm, into which the siloxane is painted for the measurement.
- the two outer flat electrodes are attached at a distance of 16 cm, which means that the current flows through the entire sample.
- the two point electrodes with a diameter of 1 cm are located in the base plate at a distance of 12 cm (1) and measure the voltage.
- the specific resistance is calculated from the measured resistance R using the following formula.
- the printing inks were vulcanized in the form of a 2 mm plate and the type 1 shoulder stick was punched.
- the test specimen is subjected to a four-wire measurement. This is clamped in the middle between two electrically conductive clamping jaws so that the distance between them is 84.0 mm.
- the clamping jaws which represent the two outer electrical contacts, are structured, which means that the structure achieves a penetration effect into the material (piercing).
- the two internal contacts are made by positioning two tendon 11 clamps 29.5 mm from the nearest jaw and 25 cm apart.
- the two inner measuring clamps are pre-treated with silver conductive paste.
- the printing ink was prepared analogously to printing ink 1 in example 1, with the difference that carbon black premix B was used.
- the printing ink was prepared analogously to printing ink 3 in example 3, with the difference that carbon black premix B was used.
- Example 5 Production of Printing Ink 5 (Not According to the Invention)
- the printing ink was prepared analogously to printing ink 1 in example 1, with the difference that carbon black premix C was used.
- the printing ink was prepared analogously to printing ink 3 in example 3, with the difference that carbon black premix C was used.
- the following table compares the amounts of CNT and carbon black used in the examples and the results of the measurements.
- printing inks 5, 6 and 7, which are not the subject of the present invention have a higher viscosity. Should R/Ro at 50% elongation not exceed the value of 1.5 the viscosity of the printing inks with high-conductivity carbon black with a BET of 1400 g/m 2 (printing inks 6 and 7) is at least 100 Pas.
- the soot-free printing inks are characterized by either high viscosity (No. 8) or low conductivity (No. 9). In summary, it can be seen that only printing inks 1, 2, 3 and 4, which contain a carbon black with a low BET surface area, combine good electrical properties and low viscosity.
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Abstract
Description
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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CN202180103288.3A CN118103925A (zh) | 2021-10-13 | 2021-10-13 | 具有碳纳米管和炭黑的导电硅酮组合物 |
PCT/EP2021/078323 WO2023061579A1 (de) | 2021-10-13 | 2021-10-13 | ELEKTRISCH LEITFÄHIGE SILICONZUSAMMENSETZUNG MIT KOHLENSTOFFNANORÖHREN UND RUß |
KR1020247011804A KR20240052090A (ko) | 2021-10-13 | 2021-10-13 | 탄소 나노튜브 및 카본 블랙을 포함하는 전기 전도성 실리콘 조성물 |
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PCT/EP2021/078323 WO2023061579A1 (de) | 2021-10-13 | 2021-10-13 | ELEKTRISCH LEITFÄHIGE SILICONZUSAMMENSETZUNG MIT KOHLENSTOFFNANORÖHREN UND RUß |
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Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2050768A1 (de) | 2007-10-02 | 2009-04-22 | Wacker Chemie AG | Härtbare Siliconzusammensetzungen |
WO2009153192A2 (de) | 2008-06-18 | 2009-12-23 | Basf Se | Verfahren zur herstellung von elektroden für solarzellen |
WO2010069900A1 (de) | 2008-12-17 | 2010-06-24 | Basf Se | Verfahren und druckmaschine zum bedrucken eines substrates |
CN103160128A (zh) | 2013-04-10 | 2013-06-19 | 北京化工大学 | 一种极低压缩变形低硬度的导电硅橡胶材料及制备方法 |
US20140060903A1 (en) | 2012-08-30 | 2014-03-06 | Shin-Etsu Chemical Co., Ltd. | Conductive ink composition, formation of conductive circuit, and conductive circuit |
WO2015181810A1 (en) | 2014-05-27 | 2015-12-03 | Orbotech Ltd. | Printing of 3d structures by laser-induced forward transfer |
US9253878B2 (en) | 2012-03-29 | 2016-02-02 | Sumitomo Riko Company Limited | Conductive composition and conductive film |
US20160351289A1 (en) | 2015-05-28 | 2016-12-01 | Honda Motor Co., Ltd. | Conductive paste composition |
WO2020063799A1 (en) * | 2018-09-28 | 2020-04-02 | Dow Silicones Corporation | Liquid silicone rubber composition |
WO2020156632A1 (de) * | 2019-01-28 | 2020-08-06 | Wacker Chemie Ag | Verfahren zur aufbringung wenigstens einer siliconschicht mittels laser-transferdruck |
-
2021
- 2021-10-13 CN CN202180103288.3A patent/CN118103925A/zh active Pending
- 2021-10-13 WO PCT/EP2021/078323 patent/WO2023061579A1/de active Application Filing
- 2021-10-13 KR KR1020247011804A patent/KR20240052090A/ko unknown
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2050768A1 (de) | 2007-10-02 | 2009-04-22 | Wacker Chemie AG | Härtbare Siliconzusammensetzungen |
EP2050768B1 (de) | 2007-10-02 | 2012-12-05 | Wacker Chemie AG | Härtbare Siliconzusammensetzungen |
WO2009153192A2 (de) | 2008-06-18 | 2009-12-23 | Basf Se | Verfahren zur herstellung von elektroden für solarzellen |
WO2010069900A1 (de) | 2008-12-17 | 2010-06-24 | Basf Se | Verfahren und druckmaschine zum bedrucken eines substrates |
US9253878B2 (en) | 2012-03-29 | 2016-02-02 | Sumitomo Riko Company Limited | Conductive composition and conductive film |
US20140060903A1 (en) | 2012-08-30 | 2014-03-06 | Shin-Etsu Chemical Co., Ltd. | Conductive ink composition, formation of conductive circuit, and conductive circuit |
CN103160128A (zh) | 2013-04-10 | 2013-06-19 | 北京化工大学 | 一种极低压缩变形低硬度的导电硅橡胶材料及制备方法 |
WO2015181810A1 (en) | 2014-05-27 | 2015-12-03 | Orbotech Ltd. | Printing of 3d structures by laser-induced forward transfer |
US20160351289A1 (en) | 2015-05-28 | 2016-12-01 | Honda Motor Co., Ltd. | Conductive paste composition |
WO2020063799A1 (en) * | 2018-09-28 | 2020-04-02 | Dow Silicones Corporation | Liquid silicone rubber composition |
WO2020156632A1 (de) * | 2019-01-28 | 2020-08-06 | Wacker Chemie Ag | Verfahren zur aufbringung wenigstens einer siliconschicht mittels laser-transferdruck |
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KR20240052090A (ko) | 2024-04-22 |
CN118103925A (zh) | 2024-05-28 |
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