CN107207426B - 耐寒性密封剂及其组分 - Google Patents

耐寒性密封剂及其组分 Download PDF

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Publication number
CN107207426B
CN107207426B CN201680009517.4A CN201680009517A CN107207426B CN 107207426 B CN107207426 B CN 107207426B CN 201680009517 A CN201680009517 A CN 201680009517A CN 107207426 B CN107207426 B CN 107207426B
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polymer
polysulfide
polysulfide polymer
divalent group
formula
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Chinese (zh)
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CN107207426A (zh
Inventor
苏珊·E·德莫斯
乔纳森·D·祖克
马修·卡佩尔
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3M Innovative Properties Co
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3M Innovative Properties Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/18—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/14—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
    • 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
    • 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
    • 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
    • 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
    • C08G75/12—Polythioether-ethers
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Sealing Material Composition (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Epoxy Resins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN201680009517.4A 2015-02-13 2016-02-10 耐寒性密封剂及其组分 Expired - Fee Related CN107207426B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562116019P 2015-02-13 2015-02-13
US62/116,019 2015-02-13
PCT/US2016/017347 WO2016130673A1 (en) 2015-02-13 2016-02-10 Cold-tolerant sealants and components thereof

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CN107207426A CN107207426A (zh) 2017-09-26
CN107207426B true CN107207426B (zh) 2020-02-14

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US (2) US10287466B2 (enExample)
EP (1) EP3256512B1 (enExample)
JP (2) JP6715853B2 (enExample)
KR (1) KR20170116114A (enExample)
CN (1) CN107207426B (enExample)
BR (1) BR112017017414A2 (enExample)
CA (1) CA2976436A1 (enExample)
WO (1) WO2016130673A1 (enExample)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017044704A1 (en) 2015-09-10 2017-03-16 3M Innovative Properties Company Polymerizable compositions, polymerized compositions, and methods of making and using the same
JP6875519B2 (ja) * 2016-11-04 2021-05-26 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 硫黄含有ポリ（アルケニル）エーテル、硫黄含有ポリエーテル（アルケニル）エーテルを包含するプレポリマー及びその使用
EP3822298A1 (en) 2016-12-13 2021-05-19 3M Innovative Properties Co. Epoxy stabilization using substituted barbituric acids
EP3555169A1 (en) 2016-12-13 2019-10-23 3M Innovative Properties Company Epoxy stabilization using acid-coated nitrogen-containing catalysts, particles, and methods
WO2018112130A1 (en) 2016-12-14 2018-06-21 3M Innovative Properties Company Sealant tape
US20210062858A1 (en) 2017-09-26 2021-03-04 3M Innovative Properties Company Curable sealant compositions, seal cap, and methods of making and using the same
US11396583B2 (en) 2017-12-07 2022-07-26 Nouryon Chemicals International B.V. Process for the preparation of a polythioethersulfide
WO2019123260A2 (en) 2017-12-19 2019-06-27 3M Innovative Properties Company Multi-part composition having staged viscosity prior to hardening
US20210024793A1 (en) 2018-03-16 2021-01-28 3M Innovative Properties Company Compositions, method of bonding, and assembly
WO2019175709A1 (en) 2018-03-16 2019-09-19 3M Innovative Properties Company Compositions, method of bonding, and bonded assembly
EP3807043A1 (en) 2018-06-15 2021-04-21 3M Innovative Properties Company Assemblies and methods of making a shim
EP3856816A1 (en) 2018-09-25 2021-08-04 3M Innovative Properties Company Polymeric material including uretdione-containing material, polythiol, and acidic stabilizer, two-part compositions, and methods
WO2020065456A1 (en) 2018-09-25 2020-04-02 3M Innovative Properties Company One-part thermally curable composition
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
US20220258848A1 (en) 2019-07-25 2022-08-18 3M Innovative Properties Company Methods of shimming an assembly
WO2021094887A1 (en) 2019-11-15 2021-05-20 3M Innovative Properties Company Curable compositions and methods of making and using the same
WO2021124033A1 (en) 2019-12-19 2021-06-24 3M Innovative Properties Company Two-part compositions including a uretdione-containing material and inorganic filler, products, and methods
JP7613861B2 (ja) 2020-09-23 2025-01-15 サトーホールディングス株式会社 Ｒｆｉｄラベル及びｒｆｉｄラベルの使用方法
CN113913150B (zh) * 2021-11-18 2023-03-14 中国航发北京航空材料研究院 用于飞机钣金件的贴合面密封剂
US20260027675A1 (en) 2022-03-21 2026-01-29 3M Innovative Properties Company Curable composition, treated backing, coated abrasive articles including the same, and methods of making and using the same
US20250196292A1 (en) 2022-03-21 2025-06-19 3M Innovative Properties Company Curable composition, coated abrasive article containing the same, and methods of making and using the same
WO2025200154A1 (en) 2024-03-29 2025-10-02 3M Innovative Properties Company Two-part epoxy composition comprising thiol curative, and catalyst

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1063683A (zh) * 1990-12-28 1992-08-19 法国石油公司 新的含硫化合物，它们的制备及其用作润滑油中的添加剂
US20030008977A1 (en) * 1997-02-19 2003-01-09 Zook Jonathan D. Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer
US20090069407A1 (en) * 2007-03-28 2009-03-12 Phero Tech International Inc. Compounds, compositions and methods for repelling blood-feeding arthropods and deterring their landing and feeding

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2664414A (en) 1952-03-08 1953-12-29 Shell Dev Monomers and polymers of unsaturated thioethers
GB1276362A (en) 1968-05-21 1972-06-01 Aquitaine Petrole Synthesis of halogenated thioethers
CH628074A5 (de) 1977-03-10 1982-02-15 Ciba Geigy Ag Haertbare mischungen auf basis von epoxidverbindungen.
US4366307A (en) 1980-12-04 1982-12-28 Products Research & Chemical Corp. Liquid polythioethers
US4609762A (en) 1984-01-30 1986-09-02 Products Research & Chemical Corp. Thioethers having a high sulfur content and method therefor
JPH0477576A (ja) * 1990-07-13 1992-03-11 Tatsuta Electric Wire & Cable Co Ltd 圧電ブザー及びその電極形成用塗料
US5415794A (en) * 1990-12-28 1995-05-16 Institut Francais Du Petrole New sulfured compounds, their preparation and their use as additives for lubricating oils
US5225472A (en) 1992-05-19 1993-07-06 Courtaulds Aerospace, Inc. Low viscosity polythiol and method therefor
DE69318369T2 (de) 1992-10-22 1999-01-28 Ajinomoto Co., Inc., Tokio/Tokyo Polythiol-Epoxidharz-Mischung mit längerer Verarbeitungszeit
US5464910A (en) 1993-12-22 1995-11-07 Shikoku Chemicals Corporation Epoxy resin adduct combined with a borate ester and phenolic compound
US5593795A (en) 1995-05-01 1997-01-14 Minnesota Mining And Manufacturing Company Polymer electrolyte composition based upon thiol-ene chemistry
US5912319A (en) 1997-02-19 1999-06-15 Courtaulds Aerospace, Inc. Compositions and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility
ATE243232T1 (de) * 1997-02-19 2003-07-15 Prc Desoto Int Inc Zusammensetzung und verfahren zur herstellung von flüssiger, treibstoffbeständiger polymere mit hoher biegsamkeit bei tiefer temperatur
US6372849B2 (en) 1997-02-19 2002-04-16 Prc-Desoto International, Inc. Sealants and potting formulations including polymers produced by the reaction of a polythiol and polyvinyl ether monomer
US5959071A (en) 1998-03-31 1999-09-28 Courtaulds Aerospace, Inc. Composition and method for producing polythioethers having pendent methyl chains
JP4704573B2 (ja) 1999-05-10 2011-06-15 スリーエム イノベイティブ プロパティズ カンパニー エン−チオールエラストマーを作成するための組成物
ATE297429T1 (de) 2000-03-09 2005-06-15 Advanced Chemistry And Technol Hochfeste polymere und raumfahrtversiegelungen daraus
MXPA02012550A (es) * 2000-06-30 2004-05-05 Prc De Soto International Inc Formulaciones obturantes y encapsulantes que incluyen polimeros producidos por la reaccion de un politiol y monomero polivinil eter.
US7097883B2 (en) * 2003-06-05 2006-08-29 Ppg Industries Ohio, Inc. Low temperature liquid polythioether polymers
US20050010003A1 (en) * 2003-07-11 2005-01-13 Prc-Desoto International, Inc. Epoxy-capped polythioethers
US7622548B2 (en) 2003-07-11 2009-11-24 Prc Desoto International, Inc. Epoxy- or amine/hydroxy-capped polythioethers
JP4569129B2 (ja) * 2004-03-04 2010-10-27 三菱化学株式会社 リチウム二次電池用非水系電解液及びそれを用いたリチウム二次電池
US7390859B2 (en) 2005-02-08 2008-06-24 Ppg Industries Ohio, Inc. Compositions and methods of making compositions exhibiting fuel resistance
US8349951B2 (en) 2005-05-31 2013-01-08 Prc Desoto International, Inc. Polythioether polymers and curable compositions containing them
US20070096396A1 (en) 2005-10-27 2007-05-03 Sawant Suresh G Dimercaptan terminated polythioether polymers and methods for making and using the same
KR101029908B1 (ko) 2006-05-05 2011-04-18 피피지 인더스트리즈 오하이오 인코포레이티드 싸이오에터 작용성 올리고머성 폴리싸이올로부터 제조된 조성물 및 제품
US7879955B2 (en) 2007-05-01 2011-02-01 Rao Chandra B Compositions including a polythioether
US7875666B2 (en) 2008-04-24 2011-01-25 Prc-De Soto International, Inc. Thioethers, methods for their preparation, and compositions including such thioethers
KR101089540B1 (ko) 2008-11-07 2011-12-05 요코하마 고무 가부시키가이샤 1액형 열경화성 에폭시 수지 조성물
TWI586749B (zh) 2010-11-19 2017-06-11 漢高日本股份有限公司 單組分環氧樹脂組成物
CN103282401A (zh) 2011-01-05 2013-09-04 纳美仕有限公司 树脂组合物
US9056949B2 (en) * 2013-06-21 2015-06-16 Prc-Desoto International, Inc. Michael addition curing chemistries for sulfur-containing polymer compositions employing bis(sulfonyl)alkanols
US9062139B2 (en) * 2013-03-15 2015-06-23 Prc-Desoto International, Inc. Sulfone-containing polythioethers, compositions thereof, and methods of synthesis
JP7016698B2 (ja) * 2014-12-23 2022-02-07 スリーエム イノベイティブ プロパティズ カンパニー ２系統硬化のポリチオエーテル

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1063683A (zh) * 1990-12-28 1992-08-19 法国石油公司 新的含硫化合物，它们的制备及其用作润滑油中的添加剂
US20030008977A1 (en) * 1997-02-19 2003-01-09 Zook Jonathan D. Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer
US20090069407A1 (en) * 2007-03-28 2009-03-12 Phero Tech International Inc. Compounds, compositions and methods for repelling blood-feeding arthropods and deterring their landing and feeding

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A CONVENIENT SYNTHESIS OF POLYSULFIDES BY PHASE TRANSFER CATALYSIS;D. ROBERTS et al;《 Phosphorus,Sulfur,and Silicon》;20060923;第83卷;第50页sheme II *
A novel tin (II) dithioether complex;A.R. Hutchison et al;《 Journal of Organometallic Chemistry》;20051222;第691卷;第1659页Fig.1 *
Novel synthesis of symmetrical 3,30-allyl dithioethers as photoplastic monomer precursors by equal molar rate addition of reactants and solvent controlled oligomerization;Cornelis M. et al;《Monatsh Chem》;20130403;第144卷;第893页左栏scheme 1 *

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WO2016130673A1 (en) 2016-08-18
CN107207426A (zh) 2017-09-26
JP6972238B2 (ja) 2021-11-24
EP3256512A1 (en) 2017-12-20
CA2976436A1 (en) 2016-08-18
KR20170116114A (ko) 2017-10-18
JP2018506543A (ja) 2018-03-08
US10544339B2 (en) 2020-01-28
BR112017017414A2 (pt) 2018-04-03
JP6715853B2 (ja) 2020-07-01
US20180016480A1 (en) 2018-01-18
US10287466B2 (en) 2019-05-14
EP3256512B1 (en) 2022-07-20
US20190256752A1 (en) 2019-08-22
JP2020158778A (ja) 2020-10-01

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