CA2905328A1 - Radiation curable polythioethers with alkyne-based linkage - Google Patents
Radiation curable polythioethers with alkyne-based linkage Download PDFInfo
- Publication number
- CA2905328A1 CA2905328A1 CA2905328A CA2905328A CA2905328A1 CA 2905328 A1 CA2905328 A1 CA 2905328A1 CA 2905328 A CA2905328 A CA 2905328A CA 2905328 A CA2905328 A CA 2905328A CA 2905328 A1 CA2905328 A1 CA 2905328A1
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- monomer
- composition
- polythioether polymer
- 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.)
- Abandoned
Links
- 229920006295 polythiol Polymers 0.000 title claims abstract description 42
- 230000005855 radiation Effects 0.000 title claims abstract description 21
- 150000001345 alkine derivatives Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 229920000642 polymer Polymers 0.000 claims abstract description 29
- 239000000565 sealant Substances 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 21
- 150000001993 dienes Chemical class 0.000 claims abstract description 6
- 150000004662 dithiols Chemical class 0.000 claims abstract description 6
- 150000003573 thiols Chemical class 0.000 claims abstract description 6
- 239000003822 epoxy resin Substances 0.000 claims abstract description 5
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 14
- 239000000446 fuel Substances 0.000 claims description 8
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 6
- 239000002105 nanoparticle Substances 0.000 claims description 5
- 230000004584 weight gain Effects 0.000 claims description 4
- 235000019786 weight gain Nutrition 0.000 claims description 4
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- 241000579895 Chlorostilbon Species 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229910052876 emerald Inorganic materials 0.000 description 1
- 239000010976 emerald Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RSPZSDWVQWRAEF-UHFFFAOYSA-N hepta-1,6-diyne Chemical compound C#CCCCC#C RSPZSDWVQWRAEF-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- DSOJWVLXZNRKCS-UHFFFAOYSA-N octa-1,7-diyne Chemical compound C#CCCCCC#C DSOJWVLXZNRKCS-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000012812 sealant material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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
- C08G75/14—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361779485P | 2013-03-13 | 2013-03-13 | |
| US61/779,485 | 2013-03-13 | ||
| PCT/US2014/020587 WO2014164103A1 (en) | 2013-03-13 | 2014-03-05 | Radiation curable polythioethers with alkyne-based linkage |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2905328A1 true CA2905328A1 (en) | 2014-10-09 |
Family
ID=50382658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2905328A Abandoned CA2905328A1 (en) | 2013-03-13 | 2014-03-05 | Radiation curable polythioethers with alkyne-based linkage |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20160032059A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2970589B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6463723B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20150127635A (cg-RX-API-DMAC7.html) |
| CN (1) | CN105073837B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112015022647A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2905328A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2643480T3 (cg-RX-API-DMAC7.html) |
| PL (1) | PL2970589T3 (cg-RX-API-DMAC7.html) |
| PT (1) | PT2970589T (cg-RX-API-DMAC7.html) |
| WO (1) | WO2014164103A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016516848A (ja) * | 2013-03-13 | 2016-06-09 | スリーエム イノベイティブ プロパティズ カンパニー | ポリチオエーテル系シーラント |
| PT3090006T (pt) | 2013-12-30 | 2017-12-22 | 3M Innovative Properties Co | Composições que incluem um politiol, um composto insaturado e um corante e métodos relacionados com essas composições |
| EP3090025A4 (en) | 2013-12-30 | 2017-08-23 | 3M Innovative Properties Company | Dye, filler made therefrom, compositions including the filler, and method of determining degree of cure of such compositions |
| WO2016106352A1 (en) | 2014-12-23 | 2016-06-30 | 3M Innovative Properties Company | Dual cure polythioether |
| WO2016176548A1 (en) | 2015-04-29 | 2016-11-03 | 3M Innovative Properties Company | Composition including a polythiol and a polyepoxide and methods relating to the composition |
| CA2991039A1 (en) * | 2015-06-29 | 2017-01-05 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
| CA3029558A1 (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 |
| WO2018085534A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and a coumarin and related methods |
| 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 |
| 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 |
| US20200347227A1 (en) * | 2018-01-30 | 2020-11-05 | Namics Corporation | Resin composition and cured material of same, adhesive, semiconductor device, and electronic component |
| EP3807043A1 (en) | 2018-06-15 | 2021-04-21 | 3M Innovative Properties Company | Assemblies and methods of making a shim |
| CN109206615A (zh) * | 2018-08-31 | 2019-01-15 | 浙江大学 | 一种聚烯硫醚类化合物及其制备方法 |
| US20220258848A1 (en) | 2019-07-25 | 2022-08-18 | 3M Innovative Properties Company | Methods of shimming an assembly |
| US12428559B2 (en) | 2019-11-15 | 2025-09-30 | 3M Innovative Properties Company | Curable compositions and methods of making and using the same |
| US20250290002A1 (en) * | 2024-03-13 | 2025-09-18 | The Boeing Company | Jet reference fluid formulations for fuel surrogates and methods thereof |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62232424A (ja) * | 1986-04-02 | 1987-10-12 | Showa Highpolymer Co Ltd | 硬化可能な組成物 |
| JPH0645696B2 (ja) * | 1988-05-10 | 1994-06-15 | 昭和高分子株式会社 | 硬化可能な樹脂組成物 |
| JPH0645697B2 (ja) * | 1988-06-02 | 1994-06-15 | 昭和高分子株式会社 | 硬化可能な樹脂組成物 |
| JPH0255731A (ja) * | 1988-08-23 | 1990-02-26 | Mitsubishi Petrochem Co Ltd | 架橋された重合体成形物 |
| JPH0255732A (ja) * | 1988-08-23 | 1990-02-26 | Mitsubishi Petrochem Co Ltd | 架橋された重合体成形物 |
| JP2820356B2 (ja) * | 1993-04-27 | 1998-11-05 | 積水フアインケミカル株式会社 | 光硬化性樹脂組成物 |
| JPH09241589A (ja) * | 1996-03-13 | 1997-09-16 | Minnesota Mining & Mfg Co <3M> | 衝撃緩和性粘着シート及び衝撃緩和構造体 |
| 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 |
| BR9812092A (pt) * | 1997-02-19 | 2000-11-21 | Courtaulds Aerospace Inc | Politioéter, método para a produção do poliéster e composição polimerizável |
| WO2002002710A2 (en) * | 2000-06-30 | 2002-01-10 | Prc-De Soto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
| US20100210745A1 (en) * | 2002-09-09 | 2010-08-19 | Reactive Surfaces, Ltd. | Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes |
| US7097883B2 (en) * | 2003-06-05 | 2006-08-29 | Ppg Industries Ohio, Inc. | Low temperature liquid polythioether polymers |
| US7553925B2 (en) * | 2006-05-05 | 2009-06-30 | Ppg Industries Ohio, Inc. | Thioether functional oligomeric polythiols and articles prepared therefrom |
| US8440736B2 (en) * | 2008-04-07 | 2013-05-14 | University Of Southern Mississippi | Photocuable thiol-ene low gas permeability membranes |
| US8932685B2 (en) * | 2010-08-13 | 2015-01-13 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
| JP5831891B2 (ja) * | 2011-08-10 | 2015-12-09 | デンカ株式会社 | 樹脂組成物の製造方法と接着剤 |
| FR2983204B1 (fr) * | 2011-11-30 | 2014-01-10 | Hutchinson | Composition liquide d'etancheite reticulable a la demande, son procede de preparation et ses applications |
-
2014
- 2014-03-05 US US14/775,018 patent/US20160032059A1/en not_active Abandoned
- 2014-03-05 CA CA2905328A patent/CA2905328A1/en not_active Abandoned
- 2014-03-05 PL PL14712918T patent/PL2970589T3/pl unknown
- 2014-03-05 EP EP14712918.3A patent/EP2970589B1/en not_active Not-in-force
- 2014-03-05 ES ES14712918.3T patent/ES2643480T3/es active Active
- 2014-03-05 JP JP2016500637A patent/JP6463723B2/ja not_active Expired - Fee Related
- 2014-03-05 KR KR1020157026902A patent/KR20150127635A/ko not_active Ceased
- 2014-03-05 WO PCT/US2014/020587 patent/WO2014164103A1/en not_active Ceased
- 2014-03-05 BR BR112015022647A patent/BR112015022647A2/pt not_active Application Discontinuation
- 2014-03-05 CN CN201480013692.1A patent/CN105073837B/zh not_active Expired - Fee Related
- 2014-03-05 PT PT147129183T patent/PT2970589T/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112015022647A2 (pt) | 2017-07-18 |
| JP6463723B2 (ja) | 2019-02-06 |
| EP2970589B1 (en) | 2017-08-02 |
| WO2014164103A1 (en) | 2014-10-09 |
| CN105073837B (zh) | 2017-11-10 |
| ES2643480T3 (es) | 2017-11-23 |
| KR20150127635A (ko) | 2015-11-17 |
| CN105073837A (zh) | 2015-11-18 |
| PT2970589T (pt) | 2017-10-23 |
| JP2016512278A (ja) | 2016-04-25 |
| PL2970589T3 (pl) | 2017-12-29 |
| EP2970589A1 (en) | 2016-01-20 |
| US20160032059A1 (en) | 2016-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190304 |
|
| FZDE | Discontinued |
Effective date: 20210907 |
|
| FZDE | Discontinued |
Effective date: 20210907 |