CA2878529C - Thermally conductive flexible adhesive for aerospace applications - Google Patents

Thermally conductive flexible adhesive for aerospace applications Download PDF

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Publication number
CA2878529C
CA2878529C CA2878529A CA2878529A CA2878529C CA 2878529 C CA2878529 C CA 2878529C CA 2878529 A CA2878529 A CA 2878529A CA 2878529 A CA2878529 A CA 2878529A CA 2878529 C CA2878529 C CA 2878529C
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CA
Canada
Prior art keywords
adhesive
boron nitride
adhesive material
nitride particles
particles
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.)
Active
Application number
CA2878529A
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English (en)
French (fr)
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CA2878529A1 (en
Inventor
Peter Babilo
Randall Jay Moss
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.)
Boeing Co
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Boeing Co
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 Boeing Co filed Critical Boeing Co
Publication of CA2878529A1 publication Critical patent/CA2878529A1/en
Application granted granted Critical
Publication of CA2878529C publication Critical patent/CA2878529C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/4855Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by their physical properties, e.g. being electrically-conductive
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B32B37/1284Application of adhesive
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/14Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers
    • B32B37/16Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with all layers existing as coherent layers before laminating
    • B32B37/18Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with all layers existing as coherent layers before laminating involving the assembly of discrete sheets or panels only
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/38Boron-containing compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00Use of pretreated ingredients
    • C08K9/04Ingredients treated with organic substances
    • C08K9/06Ingredients treated with organic substances with silicon-containing compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08Materials not undergoing a change of physical state when used
    • C09K5/14Solid materials, e.g. powdery or granular
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00Printed circuits
    • H05K1/02Details
    • H05K1/0201Thermal arrangements, e.g. for cooling, heating or preventing overheating
    • H05K1/0203Cooling of mounted components
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00Printed circuits
    • H05K1/02Details
    • H05K1/0201Thermal arrangements, e.g. for cooling, heating or preventing overheating
    • H05K1/0203Cooling of mounted components
    • H05K1/0209External configuration of printed circuit board adapted for heat dissipation, e.g. lay-out of conductors, coatings
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00Apparatus or processes for manufacturing printed circuits
    • H05K3/30Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/303Surface mounted components, e.g. affixing before soldering, aligning means, spacing means
    • H05K3/305Affixing by adhesive
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2063/00Use of EP, i.e. epoxy resins or derivatives thereof, as moulding material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2509/00Use of inorganic materials not provided for in groups B29K2503/00 - B29K2507/00, as filler
    • B29K2509/02Ceramics
    • B29K2509/04Carbides; Nitrides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29LINDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00Other particular articles
    • B29L2031/34Electrical apparatus, e.g. sparking plugs or parts thereof
    • B29L2031/3406Components, e.g. resistors
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B32B2037/1253Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives curable adhesive
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00Electrical equipment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/38Boron-containing compounds
    • C08K2003/382Boron-containing compounds and nitrogen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2463/00Presence of epoxy resin
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/01Dielectrics
    • H05K2201/0104Properties and characteristics in general
    • H05K2201/0133Elastomeric or compliant polymer
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/02Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203Fillers and particles
    • H05K2201/0206Materials
    • H05K2201/0209Inorganic, non-metallic particles
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/02Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203Fillers and particles
    • H05K2201/0206Materials
    • H05K2201/0239Coupling agent for particles
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2203/00Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
    • H05K2203/12Using specific substances
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Mechanical Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
CA2878529A 2014-02-25 2015-01-16 Thermally conductive flexible adhesive for aerospace applications Active CA2878529C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14/189,302 US9464214B2 (en) 2014-02-25 2014-02-25 Thermally conductive flexible adhesive for aerospace applications
US14/189,302 2014-02-25

Publications (2)

Publication Number Publication Date
CA2878529A1 CA2878529A1 (en) 2015-08-25
CA2878529C true CA2878529C (en) 2019-01-08

Family

ID=52465170

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2878529A Active CA2878529C (en) 2014-02-25 2015-01-16 Thermally conductive flexible adhesive for aerospace applications

Country Status (6)

Country Link
US (4) US9464214B2 (enExample)
EP (1) EP2911483B1 (enExample)
JP (1) JP6546403B2 (enExample)
CN (1) CN104861909B (enExample)
BR (1) BR102015003268B8 (enExample)
CA (1) CA2878529C (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9464214B2 (en) 2014-02-25 2016-10-11 The Boeing Company Thermally conductive flexible adhesive for aerospace applications
CN111995975B (zh) * 2015-11-04 2022-12-02 日立化成株式会社 粘接剂组合物和结构体
US10529641B2 (en) * 2016-11-26 2020-01-07 Texas Instruments Incorporated Integrated circuit nanoparticle thermal routing structure over interconnect region
KR102524428B1 (ko) 2017-05-10 2023-04-24 세키스이가가쿠 고교가부시키가이샤 절연성 시트 및 적층체
JP2020037634A (ja) * 2018-09-03 2020-03-12 トヨタ自動車株式会社 熱伝導性材料、その製造方法、及び熱伝導性組成物
CA3115812C (en) 2018-10-12 2023-08-01 Ppg Industries Ohio, Inc. Compositions containing thermally conductive fillers
CN110194946B (zh) * 2019-05-16 2021-10-12 上海大学 有机硅封装胶及其制备方法
WO2021035383A1 (en) * 2019-08-23 2021-03-04 Evonik Specialty Chemicals (Shanghai) Co., Ltd. Thermal conductive filler and preparation method thereof
CN110488454B (zh) * 2019-09-06 2020-11-03 中国科学院长春光学精密机械与物理研究所 一种基于柔性铰链的反射镜支撑结构
EP4232520B1 (en) 2020-10-20 2024-07-10 The Boeing Company Phthalonitrile-based high temperature resistive inks

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US4869954A (en) * 1987-09-10 1989-09-26 Chomerics, Inc. Thermally conductive materials
JPH0551540A (ja) * 1991-08-27 1993-03-02 Kawasaki Steel Corp 窒化硼素の処理方法
KR100196754B1 (ko) * 1995-07-19 1999-06-15 글렌 에이치. 렌젠 주니어 실온 안정성, 일성분계, 열전도성의 가요성 에폭시 접착제
JP3511118B2 (ja) 1996-08-16 2004-03-29 日立化成工業株式会社 接着剤、半導体装置の製造方法、および半導体装置
US6202917B1 (en) * 1998-08-19 2001-03-20 Hughes Electronics Corporation Co-processing of adhesive curing and solder reflow in an electronic assembly operation
US7445797B2 (en) 2005-03-14 2008-11-04 Momentive Performance Materials Inc. Enhanced boron nitride composition and polymer-based compositions made therewith
JP4528397B2 (ja) * 1999-12-17 2010-08-18 ポリマテック株式会社 接着方法および電子部品
EP1797155B1 (en) * 2004-08-23 2015-10-07 General Electric Company Thermally conductive composition and method for preparing the same
CN101035876A (zh) * 2004-08-23 2007-09-12 莫门蒂夫性能材料股份有限公司 导热性组合物及其制备方法
JP5343335B2 (ja) * 2006-09-29 2013-11-13 東レ株式会社 電子機器用接着剤シート
CN100491490C (zh) * 2006-11-09 2009-05-27 上海大学 低粘度导热胶粘剂及其制备方法
US7906373B1 (en) 2008-03-26 2011-03-15 Pawel Czubarow Thermally enhanced electrically insulative adhesive paste
US8017689B2 (en) * 2008-08-08 2011-09-13 The Yokohama Rubber Co., Ltd. Composition of epoxy resin, core-shell particles and curing agent
US20100167002A1 (en) * 2008-12-30 2010-07-01 Vitex Systems, Inc. Method for encapsulating environmentally sensitive devices
JP4848434B2 (ja) 2009-01-30 2011-12-28 日東電工株式会社 熱伝導性粘着剤組成物および熱伝導性粘着シート
US8288466B2 (en) 2009-05-13 2012-10-16 E I Du Pont De Nemours And Company Composite of a polymer and surface modified hexagonal boron nitride particles
TWI534256B (zh) * 2011-05-16 2016-05-21 Showa Denko Kk Hardened heat dissipation composition
KR20150008140A (ko) * 2012-05-16 2015-01-21 아라까와 가가꾸 고교 가부시끼가이샤 신축성 방열 시트 및 이의 신축성 방열 시트가 부착된 물품
US9464214B2 (en) 2014-02-25 2016-10-11 The Boeing Company Thermally conductive flexible adhesive for aerospace applications

Also Published As

Publication number Publication date
US11292943B2 (en) 2022-04-05
BR102015003268A2 (pt) 2017-07-18
US20180265751A1 (en) 2018-09-20
US20190264073A1 (en) 2019-08-29
EP2911483A1 (en) 2015-08-26
CN104861909B (zh) 2020-01-10
CA2878529A1 (en) 2015-08-25
US10336916B2 (en) 2019-07-02
US9464214B2 (en) 2016-10-11
EP2911483B1 (en) 2023-09-06
US20150240132A1 (en) 2015-08-27
JP2015160955A (ja) 2015-09-07
BR102015003268B8 (pt) 2020-07-07
JP6546403B2 (ja) 2019-07-17
CN104861909A (zh) 2015-08-26
BR102015003268B1 (pt) 2020-06-16
US10005927B2 (en) 2018-06-26
US20160376477A1 (en) 2016-12-29

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