WO2019175755A1 - Dispensable chemical composition with high amount of filler materials and low thixotropic index levels - Google Patents

Dispensable chemical composition with high amount of filler materials and low thixotropic index levels Download PDF

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Publication number
WO2019175755A1
WO2019175755A1 PCT/IB2019/051977 IB2019051977W WO2019175755A1 WO 2019175755 A1 WO2019175755 A1 WO 2019175755A1 IB 2019051977 W IB2019051977 W IB 2019051977W WO 2019175755 A1 WO2019175755 A1 WO 2019175755A1
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WO
WIPO (PCT)
Prior art keywords
polymers
dimethylsiloxane
siloxane
composition according
comprised
Prior art date
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Ceased
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PCT/IB2019/051977
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English (en)
French (fr)
Inventor
Paolo Vacca
Gaetano CAMPANELLA
Emiliano BERTINOTTI
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SAES Getters SpA
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SAES Getters SpA
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Priority to JP2019542731A priority Critical patent/JP7199363B2/ja
Priority to KR1020197023191A priority patent/KR102498509B1/ko
Priority to EP19715225.9A priority patent/EP3559089B1/en
Priority to US16/468,384 priority patent/US10954387B2/en
Priority to CN201980001036.2A priority patent/CN110494473B/zh
Publication of WO2019175755A1 publication Critical patent/WO2019175755A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • 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
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • 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
    • 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
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • 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
    • C08K3/34—Silicon-containing compounds
    • 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
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • 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
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2203—Oxides; Hydroxides of metals of lithium
    • 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
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2206—Oxides; Hydroxides of metals of calcium, strontium or barium
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/016—Additives defined by their aspect ratio
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the present invention relates to a dispensable chemical composition
  • a dispensable chemical composition comprising a blend of siloxane polymeric components and suitable to integrate high amount of filler materials (while maintaining low thixotropic index levels).
  • the dispensable composition of the present invention can be usefully employed in manufacturing electronic or opto-electronic devices.
  • the thixotropic index is a measure of the shear-dependent properties and can be defined as the ratio of viscosities measured at a certain lower rpm (or low shear rate) to viscosities measured at a certain higher rpm (or high shear rate).
  • thixotropic index is usually obtained considering viscosities recorded at shear rates of 5 s 1 and 50 s 1 .
  • TI values lower than 3 generally comprised between 2 and 3 (i.e. typical TI for gel state) and simultaneously higher viscosity values (comprised between
  • filler materials into an organic matrix is strictly related to the rheological and mechanical properties thereof and in particular, due to the rheological characteristics of typical siloxane-based formulations, it is commonly known that, in order to achieve good dispensability characteristics, the filler content should not be higher than 50% wt.
  • the present invention can be employed to obtain a composite sorber material to be used in a moisture-sensitive device in order to control the water level, both as a barrier positioned adjacent to the device perimeter by preventing moisture from entering electronic devices, and as a getter to absorb water amount at their inside.
  • moisture-sensitive device there is intended any sealed device which requires moisture levels in the range of about 0,1 to 5000 parts per million (ppm) of water vapor, because their performance is affected by moisture.
  • MEMs micro-electromechanical devices
  • MOEMs micro-opto- electromechanical devices
  • OLEDs organic light-emitting diode
  • OLETs organic solar cells
  • the typical approach for the preservation of these devices is to perform the encapsulation process by using suitable sealants, to reduce moisture transmission from the external environment, and to insert a desiccant composition inside the enclosure containing the moisture-sensitive device.
  • EP 2751029 in the applicant’s name, discloses a desiccant composition suitable to be manipulated and used in manufacturing processes for moisture-sensitive devices, effectively reducing the aggregation phenomenon of the inorganic oxide particles dispersed therein, through the functionalization of the external surface by fatty acid anions.
  • a desiccant composition suitable to be manipulated and used in manufacturing processes for moisture-sensitive devices, effectively reducing the aggregation phenomenon of the inorganic oxide particles dispersed therein, through the functionalization of the external surface by fatty acid anions.
  • a“mechanical thixotropic filler” in order to modulate the thixotropic index without increasing the volume resistivity of the curable silicone composition.
  • the present invention discloses a blend composition of at least two siloxane components, characterized by two different molecular weights in the ranges between 35000 and 70000 g/mol for a first component and between 10000 and 30000 g/mol for a second component, in a ratio of the first to the second component comprised between 0, 1 and 0,45 which can be formulated with at least one filler in an amount higher than 50%, up to 70%, by weight with respect to the total weight of the composition, resulting in suitable rheological values for a dispensing paste.
  • the final composition obtained is therefore characterized by thixotropic index values comprised between 2 and 3, and concurrently viscosity values comprised between 50000 and 120000 mPa at a shear rate of 5 s 1 and between 20000 and 50000 mPa at a shear rate of 50 s 1 .
  • the final composition is characterized by a ratio of the two siloxane components comprised between 0,15 and 0,45 and suitable rheological values for a dispensing paste consisting of thixotropic index values comprised between 2 and 3, and concurrently viscosity values comprised between 60000 and 120000 mPa at a shear rate of 5 s 1 and between 30000 and 50000 mPa at a shear rate of 50 s 1 .
  • the blend consists of two siloxane components and its average molecular weight is comprised between 20000 and 40000 g/mol.
  • composition, object of the present invention comprises a blend of at least two siloxane polymeric components selected among siloxane polymers, siloxane copolymers, dimethylsiloxane polymers, vinylmethylsiloxane polymers, phenylsiloxane polymers, diethylsiloxane-dimethylsiloxane copolymers, vinylmethylsiloxane-dimethylsiloxane copolymers, -trimethylsiloxane and -vinyl terminated polydimethylsiloxane, -dimethylvinyl terminated dimethylsiloxane polymers.
  • siloxane polymeric components selected among siloxane polymers, siloxane copolymers, dimethylsiloxane polymers, vinylmethylsiloxane polymers, phenylsiloxane polymers, diethylsiloxane-dimethylsiloxane copolymers, vinylmethylsiloxane-d
  • the first siloxane polymeric component is characterized by a molecular weight comprised between 35000 and 70000 g/mol, and it can be selected among dimethylsiloxane polymers and -trimethylsiloxy terminated dimethylsiloxane polymers, phenylsiloxane polymers, diethylsiloxane-dimethylsiloxane copolymers, vinylmethylsiloxane - dimethylsiloxane copolymers, -vinyl terminated polydimethylsiloxane and -vinyl terminated diphenylsiloxane-dimethylsiloxane copolymers, -dimethylvinyl terminated dimethylsiloxane polymers.
  • the second siloxane component with a molecular weight comprised between 10000 and 30000 g/mol can be selected in a group consisting of dimethylsiloxane polymers, vinylmethylsiloxane-dimethylsiloxane copolymers, diethylsiloxane-dimethylsiloxane copolymers with diethylsiloxane unit content lower than 25%, vinylmethylsiloxane - dimethylsiloxane copolymers with vinylmethylsiloxane unit content lower than 25%, -trimethylsiloxane and -vinyl terminated dimethylsiloxane polymers, -vinyl terminated diphenylsiloxane-dimethylsiloxane copolymers, -trimethylsiloxy terminated vinylmethylsiloxane polymers, -vinylphenylmethyl terminated vinylphenylsiloxane- phenylmethylsiloxane copolymer,
  • the present composition is then completed with at least one first filler material in an amount comprised between 50 and 70% by weight, preferably between 55 and 65%, and selected in a group consisting of alkaline earth metal oxides, lithium oxide, aluminosilicates, zeolites, metal organic framework MOF, adsorbing polymers and organic acid.
  • said first filler material can be characterized by a shape factor, defined as the ratio between length and thickness of the particles, comprised between 1 and 5, and when they are used as powders, the maximum of the granulometric distribution is generally comprised between 0, 1 and 20 pm.
  • a second filler selected in a group consisting of fumed silica, silica, graphene and graphene oxide, CNT, phyllosilicate, nanocrystalline cellulose, polymer fibers and particles, can be optionally added in an amount lower than 10% by weight.
  • Different samples are prepared mixing together single or blended dimethylsiloxane polymers with calcium oxide or LTA zeolites as first filler and graphene oxide as second filler.
  • Sample compositions 1 to 4 are in accordance with the present invention and compared to sample 5, characterized by a different ratio between the two siloxane matrices, and sample 7 which was prepared according to EP 2550692.
  • Viscosities for each sample have been measured for the blend of the polymeric components in the selected ratio at a shear rate of 5 s 1 and compared to the final compositions containing the fillers.
  • Viscosity (cP) at different shear rates (s- 1) has been measured by means of a rotational rheometer in flow curve test mode, with 20 mm cone/plate geometry and 0,052 mm gap.
  • Test temperature is preserved by a Peltier cell and a thermostatic bath. Obtained values are the result of averaging over three analyses performed on fresh material amounts.
  • Thixotropic indexes of both the blends and the compositions have been calculated as the ratio of viscosities measured at a shear rate of 5 s _1 (low shear rate) to viscosity measured at a shear rate of 50 s 1 (high shear rate).
  • the comparative examples 5 and 6 point out that, although the final molecular weight of the blend is similar to the values according to our invention (i.e. examples 2 and 4), a different ratio between the two siloxane matrices (higher than 0,45) brings to viscosity values not suitable for a dispensing paste.
  • sample 7 characterized by a single siloxane matrix according to EP 2550692 shows to have unsuitable rheological values, with both viscosities and thixotropic index values of the final composition outside from the typical range of a dispensing paste.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Sealing Material Composition (AREA)
PCT/IB2019/051977 2018-03-14 2019-03-12 Dispensable chemical composition with high amount of filler materials and low thixotropic index levels Ceased WO2019175755A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2019542731A JP7199363B2 (ja) 2018-03-14 2019-03-12 高含量のフィラー材料及び低チクソトロピックインデックスレベルの分配可能な化学組成物
KR1020197023191A KR102498509B1 (ko) 2018-03-14 2019-03-12 다량의 충전제 물질 및 낮은 요변성 지수 수준을 갖는 분배가능한 화학적 조성물
EP19715225.9A EP3559089B1 (en) 2018-03-14 2019-03-12 Dispensable chemical composition with high amount of filler materials and low thixotropic index levels
US16/468,384 US10954387B2 (en) 2018-03-14 2019-03-12 Dispensable chemical composition with high amount of filler materials and low thixotropic index levels
CN201980001036.2A CN110494473B (zh) 2018-03-14 2019-03-12 具有大量填料材料和低触变指数水平的可分配化学组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102018000003535 2018-03-14
IT102018000003535A IT201800003535A1 (it) 2018-03-14 2018-03-14 Composizione chimica distribuibile con elevata quantità di materiale di carica e bassi livelli di indice tixotropico

Publications (1)

Publication Number Publication Date
WO2019175755A1 true WO2019175755A1 (en) 2019-09-19

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PCT/IB2019/051977 Ceased WO2019175755A1 (en) 2018-03-14 2019-03-12 Dispensable chemical composition with high amount of filler materials and low thixotropic index levels

Country Status (8)

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US (1) US10954387B2 (https=)
EP (1) EP3559089B1 (https=)
JP (1) JP7199363B2 (https=)
KR (1) KR102498509B1 (https=)
CN (1) CN110494473B (https=)
IT (1) IT201800003535A1 (https=)
TW (1) TWI766150B (https=)
WO (1) WO2019175755A1 (https=)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021178119A1 (en) * 2020-03-05 2021-09-10 Dow Global Technologies Llc Shear thinning thermally conductive silicone compositions
WO2024242157A1 (ja) * 2023-05-23 2024-11-28 デンカ株式会社 放熱グリース

Citations (5)

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US5922470A (en) * 1993-12-22 1999-07-13 Schering-Plough Healthcare Products, Inc. Soft polysiloxanes having a pressure sensitive adhesive
EP1788031A1 (en) * 2005-11-22 2007-05-23 Shin-Etsu Chemical Co., Ltd. Thermally conductive silicone rubber composition
WO2011117094A1 (en) * 2010-03-22 2011-09-29 Saes Getters S.P.A. Composition for the protection of moisture sensitive devices
EP2751029A1 (en) 2012-06-08 2014-07-09 Saes Getters S.p.A. Desiccant composition containing surface-modified powders of metal oxides useful for manufacture and protection of moisture-sensitive devices
WO2014143627A1 (en) * 2013-03-14 2014-09-18 Dow Corning Corporation Curable silicone compositions, electrically conductive silicone adhesives, methods of making and using same, and electrical devices containing same

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Patent Citations (7)

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US5922470A (en) * 1993-12-22 1999-07-13 Schering-Plough Healthcare Products, Inc. Soft polysiloxanes having a pressure sensitive adhesive
EP1788031A1 (en) * 2005-11-22 2007-05-23 Shin-Etsu Chemical Co., Ltd. Thermally conductive silicone rubber composition
WO2011117094A1 (en) * 2010-03-22 2011-09-29 Saes Getters S.P.A. Composition for the protection of moisture sensitive devices
EP2550692A1 (en) 2010-03-22 2013-01-30 SAES GETTERS S.p.A. Composition for the protection of moisture sensitive devices
EP2751029A1 (en) 2012-06-08 2014-07-09 Saes Getters S.p.A. Desiccant composition containing surface-modified powders of metal oxides useful for manufacture and protection of moisture-sensitive devices
WO2014143627A1 (en) * 2013-03-14 2014-09-18 Dow Corning Corporation Curable silicone compositions, electrically conductive silicone adhesives, methods of making and using same, and electrical devices containing same
US9447308B2 (en) 2013-03-14 2016-09-20 Dow Corning Corporation Curable silicone compositions, electrically conductive silicone adhesives, methods of making and using same, and electrical devices containing same

Also Published As

Publication number Publication date
EP3559089A1 (en) 2019-10-30
CN110494473B (zh) 2023-01-17
US20200062961A1 (en) 2020-02-27
US10954387B2 (en) 2021-03-23
TW201938663A (zh) 2019-10-01
KR102498509B1 (ko) 2023-02-10
TWI766150B (zh) 2022-06-01
CN110494473A (zh) 2019-11-22
IT201800003535A1 (it) 2019-09-14
EP3559089B1 (en) 2023-01-25
KR20200133173A (ko) 2020-11-26
JP2021515814A (ja) 2021-06-24
JP7199363B2 (ja) 2023-01-05

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