WO2015014876A3 - Process for the preparation of a polythioethersulfide - Google Patents

Process for the preparation of a polythioethersulfide Download PDF

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Publication number
WO2015014876A3
WO2015014876A3 PCT/EP2014/066340 EP2014066340W WO2015014876A3 WO 2015014876 A3 WO2015014876 A3 WO 2015014876A3 EP 2014066340 W EP2014066340 W EP 2014066340W WO 2015014876 A3 WO2015014876 A3 WO 2015014876A3
Authority
WO
WIPO (PCT)
Prior art keywords
groups
range
polymer
branched
polythioethersulfide
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/EP2014/066340
Other languages
French (fr)
Other versions
WO2015014876A2 (en
Inventor
Jan TOBIS
Olaf Klobes
Günter SONNENBURG
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.)
Nouryon Chemicals International BV
Original Assignee
Akzo Nobel Chemicals International BV
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
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Application filed by Akzo Nobel Chemicals International BV filed Critical Akzo Nobel Chemicals International BV
Priority to RU2016105775A priority Critical patent/RU2653839C2/en
Priority to CN201480042468.5A priority patent/CN105408396B/en
Priority to EP14746999.3A priority patent/EP3027676B1/en
Priority to US14/905,087 priority patent/US9771457B2/en
Priority to JP2016530508A priority patent/JP6579585B2/en
Publication of WO2015014876A2 publication Critical patent/WO2015014876A2/en
Publication of WO2015014876A3 publication Critical patent/WO2015014876A3/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
    • 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
    • C08G75/12—Polythioether-ethers
    • 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
    • C08G75/14—Polysulfides
    • 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
    • C08G75/14—Polysulfides
    • C08G75/16—Polysulfides by polycondensation of organic compounds with inorganic polysulfides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Sealing Material Composition (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)

Abstract

Process for the production of a mercapto-terminated liquid polymer with the formula HS-R-(Sy-R)t-SH, wherein each R is independently selected from branched alkanediyl or branched arenediyi groups and groups with the structure - (CH2)p-O-(CH2)q-O-(CH2)r- and wherein 0-20% of the number or R-groups in the polymer are branched alkanediyl or branched arenediyl groups and 80-100% of the number or R-groups in the polymer have the structure -(CH2)p-O-(CH2)q-O-(CH2)r-,wherein t has a value in the range 1-60, y is an average value in the range 1.0-1.5, q is an integer the range 1 to 8, and p and r are integers the range 1-10. The resulting polymer has an improved ability of recovering its original shape after release from deforming compression forces and improved tendency to recover during the application of those forces
PCT/EP2014/066340 2013-08-02 2014-07-30 Process for the preparation of a polythioethersulfide Ceased WO2015014876A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
RU2016105775A RU2653839C2 (en) 2013-08-02 2014-07-30 Process for preparation of polythioethersulphide
CN201480042468.5A CN105408396B (en) 2013-08-02 2014-07-30 Method for preparing polythioether sulfides
EP14746999.3A EP3027676B1 (en) 2013-08-02 2014-07-30 Process for the preparation of a polythioethersulfide
US14/905,087 US9771457B2 (en) 2013-08-02 2014-07-30 Process for the preparation of a polythioethersulfide
JP2016530508A JP6579585B2 (en) 2013-08-02 2014-07-30 Process for preparing polythioether sulfides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13179125.3 2013-08-02
EP13179125 2013-08-02

Publications (2)

Publication Number Publication Date
WO2015014876A2 WO2015014876A2 (en) 2015-02-05
WO2015014876A3 true WO2015014876A3 (en) 2015-04-02

Family

ID=48906176

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2014/066340 Ceased WO2015014876A2 (en) 2013-08-02 2014-07-30 Process for the preparation of a polythioethersulfide

Country Status (6)

Country Link
US (1) US9771457B2 (en)
EP (1) EP3027676B1 (en)
JP (2) JP6579585B2 (en)
CN (1) CN105408396B (en)
RU (1) RU2653839C2 (en)
WO (1) WO2015014876A2 (en)

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US10253195B2 (en) 2014-11-24 2019-04-09 Ppg Industries Ohio, Inc. Coreactive materials and methods for three-dimensional printing
BR112017017216B1 (en) 2015-02-13 2022-09-27 Chemetall Gmbh METHOD FOR SEALING, COATING OR/AND AERODYNAMIC LEVELING OF AT LEAST ONE CONNECTION ELEMENT, AUTOMATIC APPARATUS, AND, USE OF THE INVENTIVE METHOD OR/AND THE INVENTIVE APPARATUS
AU2017355487B2 (en) 2016-11-04 2020-05-21 Prc-Desoto International, Inc. Sulfur-containing poly(alkenyl) ethers, prepolymers incorporating sulfur-containing poly(alkenyl) ethers, and uses thereof
CA3066089C (en) 2017-06-09 2022-09-13 Prc-Desoto International, Inc. Dual cure sealants
US10597565B2 (en) 2017-07-07 2020-03-24 Prc-Desoto International, Inc. Hydraulic fluid and fuel resistant sealants
US10434704B2 (en) 2017-08-18 2019-10-08 Ppg Industries Ohio, Inc. Additive manufacturing using polyurea materials
US12384097B2 (en) 2017-08-18 2025-08-12 Ppg Industries Ohio, Inc. Additive manufacturing using reactive compositions
US10351674B2 (en) 2017-10-17 2019-07-16 Prc-Desoto International, Inc. Sulfur-containing polymeric particles and compositions
WO2019110598A1 (en) 2017-12-07 2019-06-13 Akzo Nobel Chemicals International B.V. Process for the preparation of a polythioethersulfide
US10843180B2 (en) 2018-10-02 2020-11-24 Prc-Desoto International, Inc. Delayed cure micro-encapsulated catalysts
EP3924187A1 (en) 2019-02-11 2021-12-22 PPG Industries Ohio, Inc. Elastomeric compositions and methods of use
CN113710481A (en) 2019-02-11 2021-11-26 Ppg工业俄亥俄公司 Multilayer system and method for producing a multilayer system
KR20210124439A (en) 2019-02-11 2021-10-14 피피지 인더스트리즈 오하이오 인코포레이티드 3D printing of sealing caps
MX2021009606A (en) 2019-02-11 2021-11-12 Ppg Ind Ohio Inc Methods of making chemically resistant sealing components.
US11015097B2 (en) 2019-03-06 2021-05-25 Prc-Desoto International, Inc. Chemically resistant sealant compositions and uses thereof
US11015057B2 (en) 2019-04-03 2021-05-25 Prc-Desoto International, Inc. Dual-cure compositions
US11505702B2 (en) 2019-04-05 2022-11-22 Prc-Desoto International, Inc. Controlled cure rate using polyether-coated synergists
US11466125B2 (en) 2019-12-19 2022-10-11 Prc-Desoto International, Inc. Low nucleation temperature polythioether prepolymers and uses thereof
US11173692B2 (en) 2019-12-19 2021-11-16 Prc-Desoto International, Inc. Free radical polymerizable adhesion-promoting interlayer compositions and methods of use
US11608458B2 (en) 2019-12-19 2023-03-21 Prc-Desoto International, Inc. Adhesion-promoting interlayer compositions containing organic titanates/zirconates and methods of use
US11624007B2 (en) 2020-01-29 2023-04-11 Prc-Desoto International, Inc. Photocurable adhesion-promoting compositions and methods of use
US11214666B2 (en) 2020-04-15 2022-01-04 Prc-Desoto International, Inc. Controlling cure rate with wetted filler
EP3913011A1 (en) 2020-05-19 2021-11-24 Nouryon Chemicals International B.V. Aliphatic epoxy-terminated polysulfide polymer
KR20230136659A (en) 2021-02-16 2023-09-26 피알시-데소토 인터내쇼날, 인코포레이티드 Compositions Containing Free Radical Polymerization Initiators
AU2022252479B9 (en) 2021-03-29 2025-12-11 Prc-Desoto International, Inc. Hybrid dual cure compositions
CN117500884A (en) 2021-04-27 2024-02-02 Ppg工业俄亥俄公司 Multi-cure co-reactive compositions for additive manufacturing and uses thereof
CA3216610A1 (en) 2021-04-28 2022-11-03 Jonas DEMPFLE Isocyanate-functionalized organosilanes as adhesion promoters in sealant and primer compositions
WO2023034890A1 (en) 2021-09-02 2023-03-09 Prc-Desoto International, Inc. Applicators for high viscosity materials
CA3235109A1 (en) 2021-11-10 2023-05-19 Andrew P. LOUGHNER Linear sealing components and methods and compositions for additively manufacturing thereof
AU2023223405B2 (en) 2022-02-23 2025-05-15 Ppg Industries Ohio, Inc. Conductive articles and methods for additive manufacturing thereof
WO2024256647A1 (en) 2023-06-16 2024-12-19 Chemetall Gmbh Adhesion promoter for polysulfide- and polythioether-based sealants
EP4727993A1 (en) 2023-06-16 2026-04-22 Chemetall GmbH Adhesion promoter for polysulfide- and polythioether-based sealants

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1545259A (en) * 1976-12-22 1979-05-02 Elf Aquitaine Polymeric organic polysulphides
US5430192A (en) * 1993-08-26 1995-07-04 Morton International, Inc. Polysulfide sealants with reduced moisture vapor transmission
US20030050511A1 (en) * 2001-09-12 2003-03-13 Gilmore John Richard Preparation of polysulfide compositions
WO2011113774A1 (en) * 2010-03-17 2011-09-22 Akzo Nobel Chemicals International B.V. Process for depolymerizing polysulfides and the preparation of bis-mercapto-diethers
WO2012139984A1 (en) * 2011-04-12 2012-10-18 Shanghai Ici Research & Development & Management Co. Ltd. Process for the preparation of a polysulfide

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2392402A (en) * 1940-10-12 1946-01-08 Thiokol Corp Monodisulphide polymer
US2466963A (en) * 1945-06-16 1949-04-12 Thiokol Corp Polysulfide polymer
JP3761552B2 (en) * 2004-03-01 2006-03-29 横浜ゴム株式会社 Process for producing polysulfide compound and rubber composition containing the same
US20070096396A1 (en) * 2005-10-27 2007-05-03 Sawant Suresh G Dimercaptan terminated polythioether polymers and methods for making and using the same
CN101486795A (en) * 2009-01-22 2009-07-22 锦西化工研究院 Novel method for preparing liquid polysulphide rubber
JP2013144756A (en) 2012-01-16 2013-07-25 Toray Fine Chemicals Co Ltd Curable composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1545259A (en) * 1976-12-22 1979-05-02 Elf Aquitaine Polymeric organic polysulphides
US5430192A (en) * 1993-08-26 1995-07-04 Morton International, Inc. Polysulfide sealants with reduced moisture vapor transmission
US20030050511A1 (en) * 2001-09-12 2003-03-13 Gilmore John Richard Preparation of polysulfide compositions
WO2011113774A1 (en) * 2010-03-17 2011-09-22 Akzo Nobel Chemicals International B.V. Process for depolymerizing polysulfides and the preparation of bis-mercapto-diethers
WO2012139984A1 (en) * 2011-04-12 2012-10-18 Shanghai Ici Research & Development & Management Co. Ltd. Process for the preparation of a polysulfide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JORCZAK AND E M FETTES J S: "Polysulfide Liquid Polymers", INDUSTRIAL AND ENGINEERING CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 43, no. 2, 1 February 1951 (1951-02-01), pages 324 - 328, XP009107340, ISSN: 0019-7866, DOI: 10.1021/IE50494A022 *

Also Published As

Publication number Publication date
CN105408396B (en) 2017-06-23
EP3027676B1 (en) 2017-10-25
JP2018127633A (en) 2018-08-16
JP2016527361A (en) 2016-09-08
US9771457B2 (en) 2017-09-26
RU2016105775A (en) 2017-09-07
RU2016105775A3 (en) 2018-03-06
JP6579585B2 (en) 2019-09-25
CN105408396A (en) 2016-03-16
WO2015014876A2 (en) 2015-02-05
US20160152775A1 (en) 2016-06-02
RU2653839C2 (en) 2018-05-15
EP3027676A2 (en) 2016-06-08

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