WO2016106352A1 - Dual cure polythioether - Google Patents

Dual cure polythioether Download PDF

Info

Publication number
WO2016106352A1
WO2016106352A1 PCT/US2015/067450 US2015067450W WO2016106352A1 WO 2016106352 A1 WO2016106352 A1 WO 2016106352A1 US 2015067450 W US2015067450 W US 2015067450W WO 2016106352 A1 WO2016106352 A1 WO 2016106352A1
Authority
WO
WIPO (PCT)
Prior art keywords
peroxide
composition according
amine
grams
curable
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.)
Ceased
Application number
PCT/US2015/067450
Other languages
English (en)
French (fr)
Inventor
Sheng Ye
Junting LI
Yizhong Wang
Joel D. Oxman
Susan E. Demoss
Jonathan D. Zook
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.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=55221521&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2016106352(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to KR1020177020355A priority Critical patent/KR20170097754A/ko
Priority to JP2017531873A priority patent/JP7016698B2/ja
Priority to BR112017013742A priority patent/BR112017013742A2/pt
Priority to US15/533,758 priority patent/US10703906B2/en
Priority to EP15828442.2A priority patent/EP3237494B1/en
Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to CN201580070296.7A priority patent/CN107108894B/zh
Priority to CA2970960A priority patent/CA2970960A1/en
Publication of WO2016106352A1 publication Critical patent/WO2016106352A1/en
Anticipated expiration legal-status Critical
Priority to US16/946,253 priority patent/US11319440B2/en
Ceased 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B64—AIRCRAFT; AVIATION; COSMONAUTICS
    • B64D—EQUIPMENT FOR FITTING IN OR TO AIRCRAFT; FLIGHT SUITS; PARACHUTES; ARRANGEMENT OR MOUNTING OF POWER PLANTS OR PROPULSION TRANSMISSIONS IN AIRCRAFT
    • B64D45/00—Aircraft indicators or protectors not otherwise provided for
    • B64D45/02—Lightning protectors; Static dischargers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/04—Polymeric products of isocyanates or isothiocyanates with vinyl compounds
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28—Chemically modified polycondensates
    • C08G8/34—Chemically modified polycondensates by natural resins or resin acids, e.g. rosin
    • 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
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • 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
    • C08K5/14—Peroxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/02—Polythioethers; Polythioether-ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
    • C09J181/02—Polythioethers; Polythioether-ethers
    • 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
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/265—Calcium, strontium or barium carbonate
    • 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
    • C08K2201/011—Nanostructured additives

Definitions

  • the amine is selected from the group consisting of dihydroxyethyl-p-toluidine, ⁇ , ⁇ -diisopropylethylamine, and N, N, N', N", N"-pentamethyl-diethylenetriamine.
  • the peroxide is selected from the group consisting of di-tert-butyl peroxide, methyl ethyl ketone peroxide, and benzoyl peroxide.
  • the composition may additionally comprise a polythiol monomer having three or more thiol groups.
  • the composition may additionally comprise one or more fillers.
  • the composition may additionally comprise one or more nanoparticle fillers.
  • the polythioether polymer exhibits high jet fuel resistance characterized by a volume swell of less than 30% and a weight gain of less than 20% when measured according to Society of Automotive Engineers (SAE) International Standard AS5127/1.
  • SAE Society of Automotive Engineers
  • the present disclosure provides a dual cure polythioether material such as a sealant.
  • the sealant has both cure on demand properties and dark cure properties.
  • the sealant may be cured by exposure to actinic radiation in 120 seconds or less, in some embodiments 90 seconds or less, in some embodiments 60 seconds or less, in some embodiments 30 seconds or less, and in some embodiments 20 seconds or less.
  • cure on demand can be initiated with UV light, in some with visible light, in some with LED sourced UV light, and in some with LED sourced visible light.
  • the initially photoinitiated cure propagates by a dark cure mechanism into adjacent portions of the polythioether material that are without light access.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Aviation & Aerospace Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Sealing Material Composition (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/US2015/067450 2014-12-23 2015-12-22 Dual cure polythioether Ceased WO2016106352A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA2970960A CA2970960A1 (en) 2014-12-23 2015-12-22 Dual cure polythioether
JP2017531873A JP7016698B2 (ja) 2014-12-23 2015-12-22 ２系統硬化のポリチオエーテル
BR112017013742A BR112017013742A2 (pt) 2014-12-23 2015-12-22 politioéter de cura dupla
US15/533,758 US10703906B2 (en) 2014-12-23 2015-12-22 Dual cure polythioether
EP15828442.2A EP3237494B1 (en) 2014-12-23 2015-12-22 Dual cure polythioether
KR1020177020355A KR20170097754A (ko) 2014-12-23 2015-12-22 이중 경화 폴리티오에테르
CN201580070296.7A CN107108894B (zh) 2014-12-23 2015-12-22 双固化聚硫醚
US16/946,253 US11319440B2 (en) 2014-12-23 2020-06-12 Dual cure polythioether

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201462095952P 2014-12-23 2014-12-23
US62/095,952 2014-12-23

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US15/533,758 A-371-Of-International US10703906B2 (en) 2014-12-23 2015-12-22 Dual cure polythioether
US16/946,253 Continuation US11319440B2 (en) 2014-12-23 2020-06-12 Dual cure polythioether

Publications (1)

Publication Number Publication Date
WO2016106352A1 true WO2016106352A1 (en) 2016-06-30

Family

ID=55221521

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/067450 Ceased WO2016106352A1 (en) 2014-12-23 2015-12-22 Dual cure polythioether

Country Status (8)

Country Link
US (2) US10703906B2 (enExample)
EP (1) EP3237494B1 (enExample)
JP (1) JP7016698B2 (enExample)
KR (1) KR20170097754A (enExample)
CN (1) CN107108894B (enExample)
BR (1) BR112017013742A2 (enExample)
CA (1) CA2970960A1 (enExample)
WO (1) WO2016106352A1 (enExample)

Cited By (21)

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WO2018005416A1 (en) * 2016-06-30 2018-01-04 3M Innovative Properties Company Dual curable thiol-ene composition, comprising a polythiol, an unsaturated compound, a photoinitiator and an organic hydroperoxide, as well as a cross-linked polymer sealant prepared therefrom for use in aerospace
WO2018085190A1 (en) * 2016-11-03 2018-05-11 3M Innovative Properties Company Polythiol sealant compositions
WO2018227149A1 (en) 2017-06-09 2018-12-13 Prc-Desoto International, Inc. Dual cure sealants
WO2019064103A1 (en) 2017-09-26 2019-04-04 1/1 Ok3M Innovative Properties Company CURABLE SEALING COMPOSITIONS, SEALING CAP, AND METHODS OF MAKING AND USING THE SAME
WO2019123393A1 (en) 2017-12-22 2019-06-27 3M Innovative Properties Company Multilayered polyetherketoneketone articles and methods thereof
US10434704B2 (en) 2017-08-18 2019-10-08 Ppg Industries Ohio, Inc. Additive manufacturing using polyurea materials
WO2019202472A2 (en) 2018-04-17 2019-10-24 3M Innovative Properties Company Conductive films
WO2019234693A1 (en) 2018-06-07 2019-12-12 3M Innovative Properties Company Lightning strike protection film
WO2019239273A1 (en) 2018-06-15 2019-12-19 3M Innovative Properties Company Assemblies and methods of making a shim
US10526440B2 (en) 2015-04-29 2020-01-07 3M Innovative Properties Company Method of making a polymer network from a polythiol and a polyepoxide
WO2020095153A1 (en) * 2018-11-09 2020-05-14 3M Innovative Properties Company Curable sealant compositions, seal cap, and methods of making and using the same
JP2020158778A (ja) * 2015-02-13 2020-10-01 スリーエム イノベイティブ プロパティズ カンパニー 耐寒性シーラント及びその構成成分
WO2020206220A1 (en) * 2019-04-03 2020-10-08 Prc-Desoto International, Inc. Dual-cure compositions
WO2021014277A1 (en) 2019-07-25 2021-01-28 3M Innovative Properties Company Methods of shimming an assembly
US10982105B2 (en) 2014-11-24 2021-04-20 Ppg Industries Ohio, Inc. Methods for reactive three-dimensional printing by extrusion
WO2021094887A1 (en) * 2019-11-15 2021-05-20 3M Innovative Properties Company Curable compositions and methods of making and using the same
US12226983B2 (en) 2019-02-11 2025-02-18 Ppg Industries Ohio, Inc. Multilayer systems and methods of making multilayer systems
US12384097B2 (en) 2017-08-18 2025-08-12 Ppg Industries Ohio, Inc. Additive manufacturing using reactive compositions
US12434434B2 (en) 2019-02-11 2025-10-07 Ppg Industries Ohio, Inc. Methods of making chemically resistant sealing components
US12441049B2 (en) 2019-02-11 2025-10-14 Ppg Industries Ohio, Inc. 3D printing of seal caps
US12503544B2 (en) 2020-02-10 2025-12-23 Ppg Industries Ohio, Inc. Elastomeric compositions and methods of use

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CA3042864A1 (en) 2016-11-03 2018-05-11 3M Innovative Properties Company Composition including a polythiol, a polyepoxide, a photolatent base, and an amine and methods relating to the composition
CA3042861A1 (en) 2016-11-03 2018-05-11 3M Innovative Properties Company Compositions including a photolatent amine, camphorquinone, and a coumarin and related methods
WO2021005533A1 (en) 2019-07-08 2021-01-14 3M Innovative Properties Company Cleaning and polishing fluid and method of using
CN113929908B (zh) * 2021-09-28 2023-08-04 武汉纺织大学 一种生物基抗菌胶粘剂及其制备方法
CN118786165A (zh) * 2022-03-01 2024-10-15 纳美仕有限公司 树脂组合物、粘接剂、密封材料、固化物、半导体装置及电子部件
KR102495856B1 (ko) * 2022-03-31 2023-02-06 김용환 사상 시스템

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Cited By (42)

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US12187904B2 (en) 2014-11-24 2025-01-07 Ppg Industries Ohio, Inc. Coreactive materials and methods for three-dimensional printing
US11920046B2 (en) 2014-11-24 2024-03-05 Ppg Industries Ohio, Inc. Coreactive materials and methods for three-dimensional printing
US11634599B2 (en) 2014-11-24 2023-04-25 Ppg Industries Ohio, Inc. Coreactive materials and methods for three-dimensional printing
US11220610B2 (en) 2014-11-24 2022-01-11 Ppg Industries Ohio, Inc. Methods for reactive three-dimensional printing by inkjet printing
US11028279B2 (en) 2014-11-24 2021-06-08 Ppg Industries Ohio, Inc. Coreactive materials and methods for three-dimensional printing
US10982105B2 (en) 2014-11-24 2021-04-20 Ppg Industries Ohio, Inc. Methods for reactive three-dimensional printing by extrusion
JP2020158778A (ja) * 2015-02-13 2020-10-01 スリーエム イノベイティブ プロパティズ カンパニー 耐寒性シーラント及びその構成成分
US10526440B2 (en) 2015-04-29 2020-01-07 3M Innovative Properties Company Method of making a polymer network from a polythiol and a polyepoxide
US11041049B2 (en) 2016-06-30 2021-06-22 3M Innovative Properties Company Dual curable thiol-ene composition, comprising a polythiol, an unsaturated compound, a photoinitiator and an organic hydroperoxide, as well as a cross-linked polymer sealant prepared therefrom for use in aerospace
WO2018005416A1 (en) * 2016-06-30 2018-01-04 3M Innovative Properties Company Dual curable thiol-ene composition, comprising a polythiol, an unsaturated compound, a photoinitiator and an organic hydroperoxide, as well as a cross-linked polymer sealant prepared therefrom for use in aerospace
WO2018085190A1 (en) * 2016-11-03 2018-05-11 3M Innovative Properties Company Polythiol sealant compositions
US10858558B2 (en) 2016-11-03 2020-12-08 3M Innovative Properties Company Polythiol sealant compositions
CN110719928A (zh) * 2017-06-09 2020-01-21 Prc-迪索托国际公司 双重固化密封剂
CN110719928B (zh) * 2017-06-09 2022-08-12 Prc-迪索托国际公司 双重固化密封剂
US20200199300A1 (en) * 2017-06-09 2020-06-25 Prc-Desoto International, Inc. Dual Cure Sealants
WO2018227149A1 (en) 2017-06-09 2018-12-13 Prc-Desoto International, Inc. Dual cure sealants
JP2020523443A (ja) * 2017-06-09 2020-08-06 ピーアールシー−デソト インターナショナル，インコーポレイティド 二重硬化シーラント
US11655340B2 (en) 2017-06-09 2023-05-23 Prc-Desoto International, Inc. Dual cure sealants
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CN107108894A (zh) 2017-08-29
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EP3237494B1 (en) 2021-06-16
JP2018501356A (ja) 2018-01-18
US11319440B2 (en) 2022-05-03
JP7016698B2 (ja) 2022-02-07
US10703906B2 (en) 2020-07-07
KR20170097754A (ko) 2017-08-28
US20170362434A1 (en) 2017-12-21
CN107108894B (zh) 2021-04-06
US20200308403A1 (en) 2020-10-01
EP3237494A1 (en) 2017-11-01

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