EP4677005A1 - Composite de silicone thermoconducteur - Google Patents

Composite de silicone thermoconducteur

Info

Publication number
EP4677005A1
EP4677005A1 EP24711432.5A EP24711432A EP4677005A1 EP 4677005 A1 EP4677005 A1 EP 4677005A1 EP 24711432 A EP24711432 A EP 24711432A EP 4677005 A1 EP4677005 A1 EP 4677005A1
Authority
EP
European Patent Office
Prior art keywords
weight percent
composition
range
alkyl
concentration
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP24711432.5A
Other languages
German (de)
English (en)
Inventor
Zhanjie Li
Dan Zhao
Devin M. FERGUSON
Eric Joffre
Bizhong Zhu
Dorab Bhagwagar
Cassandra HALE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Silicones Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Silicones Corp filed Critical Dow Silicones Corp
Publication of EP4677005A1 publication Critical patent/EP4677005A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C08K3/18—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
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O 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
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • 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
    • 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
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • 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
    • C08K2003/2296—Oxides; Hydroxides of metals of zinc
    • 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
    • C08K2201/001—Conductive additives

Definitions

  • Thermally Conductive Silicone Composite Background of the Invention
  • the present invention relates to a thermally conductive silicone composite, particularly a composite containing an ester functionalized trialkoxysilane.
  • Thermally conductive silicone composites are widely used as thermal interface materials to transfer heat from a heat-generating electronic component to a heat sink.
  • High loadings of one or more thermally conductive fillers such as zinc oxide and alumina trihydrate (Al 2 O 3 .3H 2 O, ATH) are necessary to achieve the desired thermal conductivity.
  • ATH is particularly attractive because it is non-toxic, halogen-free, chemically inert, and inexpensive.
  • ATH also resists abrasion and has the further advantage of being a flame retardant.
  • the present invention addresses a need in the art by providing a composition comprising, based on the weight of the composition, a) from 50 to 90 weight percent alumina trihydrate; b) up to 30 weight percent zinc oxide c) from 0.1 to 2 weight percent of an ester-functionalized trialkoxysilane of Formula 1 or 2: where R is C1-C16-alkyl or C2-C16-alkenyl; each R 1 is independently C1-C6-alkyl; R 2 is H or methyl; and n is 1, 2, or 3; and d) from 10 to 20 weight percent of a polysiloxane of Formula 3: where each R 3 is independently C 1 -C 6 -alkyl or phenyl; each R 4 is independently C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl; and x is from 20 to 300.
  • the composition of the present invention is useful as a thermal interface material.
  • the present invention is a) from 50 to 90 weight percent alumina trihydrate; b) up to 30 weight percent zinc oxide c) from 0.1 to 2 weight percent of an ester-functionalized trialkoxysilane of Formula 1 or 2: where R is C 1 -C 16 -alkyl or C 2 -C 16 -alkenyl; each R 1 is independently C 1 -C 6 -alkyl; R 2 is H or methyl; and n is 1, 2, or 3; and d) from 10 to 20 weight percent of a polysiloxane of Formula 3: Formula 3 where each R 3 is independently C1-C6-alkyl or phenyl; each R 4 is independently C1-C6-alkyl or C 2 -C 6 -alkenyl; and x is from 20 to 300.
  • the concentration of the alumina trihydrate in the composition is in the range of from 50 or from 55 or from 60 weight percent, to 90 or to 70 or to 68 or 65 weight percent, based on the weight of the composition.
  • the composition may further comprises ZnO at a concentration up to 30 weight percent.
  • the composition comprises ZnO at a concentration in the range of from 5 or from 15 or from 18 or from 20 weight percent, to 30 or to 27 or to 24 weight percent, based on the weight of the composition.
  • the polysiloxane of Formula 3 is preferably a polydimethylsiloxane that is terminated with two trimethylsilyl groups, or one trimethylsilyl group and one vinyldimethylsilyl group, or two vinyldimethylsilyl groups.
  • each R 3 is methyl and each R 4 is independently methyl or vinyl;
  • x (also referred to as the degree of polymerization) is from 20 or from 50 or from 100, to 300 or to 200.
  • the concentration of the polysiloxane is from 10 or from 12 weight percent to 20 or to 18 or to 16 weight percent, based on the weight of the composition.
  • the concentration of the ester-functionalized trialkoxysilane is in the range of from 0.1 or from 0.2 or from 0.4 weight percent, to 2 or to 1 or to 0.6 weight percent based on the weight of the composition.
  • R is C1-C16-alkyl or C1-C10-alkyl or C1-C6-alkyl or C2-C16-alkenyl or C 2 -C 10 -alkenyl; R is preferably methyl; each R 1 is independently a C 1 -C 6 -alkyl group, preferably methyl; R 2 is preferably methyl; and n is preferably 1 or 2.
  • the ester-functionalized trialkoxysilane of Formula 1 can be prepared, for example, by the condensation of a salt of a carboxylic acid and a trialkoxysilyl alcohol, as described in WO 2011/101278 A1.
  • the compound of Formula 1 can also be prepared by a base catalyzed reaction of a salt of a carboxylic acid and a chloromethyltrialkoxysilane: or by an a
  • the ester-functionalized trialkoxysilane of Formula 2 can be prepared by the reaction of a trichlorosilane with an acrylate or a methacrylate in the presence of a hydrosilylation catalyst such as a platinum catalyst, followed by alkanolysis:
  • a trimethylsilyl-trimethoxysilyl treating agent of Formula 4 where each R 5 is independently C 1 -C 6 -alkyl, preferably methyl; Y is O or CH 2 -CH 2 , preferably O; and x is from 20 to 200.
  • the concentration of the compound of Formula 4 is in the range of from 0.2 or from 1 to 10 or to 8 weight percent, based on the weight of the composition.
  • the composition may be curable or non-curable.
  • each R 4 is a C 2 -C 6 -alkenyl group, preferably vinyl, and the composition further comprises a polysiloxane functionalized with at least two Si-H groups and having a degree of polymerization in the range of from 5 to 300 or to 200 or to 100 or to 50.
  • the mole-to-mole ratio of the Si-H groups to the alkenyl groups of the polysiloxane of Formula 3 is preferably in the range of from 0.2:1 to 2:1.
  • composition of the present invention exhibits a lower viscosity when an alkyltrialkoxysilane treating agent is replaced by an ester-functionalized trialkoxysilane treating agent.
  • pbw refers to parts by weight
  • TA refers to an ester-functionalized trialkoxysilane treating agent.
  • Thermal Conductivity Measurement Thermal conductivity was measured by ISO 22007-2:2015 (Test Method for Determining Thermal Conductivity) using a Hot Disk Instrument TPS 2500 S Hot Disk Instrument and a C5501 sensor. Each sample was placed into two cups with the planar sensor held between the cups. Analysis conditions: Fine-tuned analysis, Temperature drift compensation and time correction, calculation with selected between points 50-150. Table 2 illustrates the impact of the treating agent on thermal conductivity (TC) and viscosity at 0.1% strain (Viscosity).

Landscapes

  • 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)

Abstract

La présente invention concerne une composition comprenant du trihydrate d'alumine, un trialcoxysilane fonctionnalisé par un ester et un polysiloxane. La composition de la présente invention est utile en tant que composite thermoconducteur présentant des propriétés de viscosité et de conductivité thermique souhaitables.
EP24711432.5A 2023-03-06 2024-02-19 Composite de silicone thermoconducteur Pending EP4677005A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363450116P 2023-03-06 2023-03-06
PCT/US2024/016357 WO2024186466A1 (fr) 2023-03-06 2024-02-19 Composite de silicone thermoconducteur

Publications (1)

Publication Number Publication Date
EP4677005A1 true EP4677005A1 (fr) 2026-01-14

Family

ID=90364307

Family Applications (1)

Application Number Title Priority Date Filing Date
EP24711432.5A Pending EP4677005A1 (fr) 2023-03-06 2024-02-19 Composite de silicone thermoconducteur

Country Status (6)

Country Link
EP (1) EP4677005A1 (fr)
JP (1) JP2026507036A (fr)
KR (1) KR20250157501A (fr)
CN (1) CN120693361A (fr)
TW (1) TW202436478A (fr)
WO (1) WO2024186466A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2026054988A (ja) * 2024-09-17 2026-03-30 信越化学工業株式会社 硬化性オルガノポリシロキサン組成物、剥離コーティング剤、及び剥離及び剥離フィルム
JP2026054987A (ja) * 2024-09-17 2026-03-30 信越化学工業株式会社 オルガノポリシロキサン及びその製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE504619T1 (de) * 2005-02-14 2011-04-15 Byk Chemie Gmbh Organosilan-modifizierte polysiloxane und deren verwendung zur oberflächenmodifizierung
DE102010002202A1 (de) * 2010-02-22 2011-08-25 Wacker Chemie AG, 81737 Verfahren zur Herstellung esterfunktioneller Silane
CN105189685B (zh) * 2013-02-11 2017-08-08 道康宁公司 用于形成导热热自由基固化有机硅组合物的方法

Also Published As

Publication number Publication date
WO2024186466A1 (fr) 2024-09-12
JP2026507036A (ja) 2026-02-27
CN120693361A (zh) 2025-09-23
TW202436478A (zh) 2024-09-16
KR20250157501A (ko) 2025-11-04

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