ES2643480T3 - Politioéteres curables por radiación con enlace a base de alquino - Google Patents
Politioéteres curables por radiación con enlace a base de alquino Download PDFInfo
- Publication number
- ES2643480T3 ES2643480T3 ES14712918.3T ES14712918T ES2643480T3 ES 2643480 T3 ES2643480 T3 ES 2643480T3 ES 14712918 T ES14712918 T ES 14712918T ES 2643480 T3 ES2643480 T3 ES 2643480T3
- Authority
- ES
- Spain
- Prior art keywords
- composition according
- composition
- curable
- sealant
- radiation
- 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
Links
- 229920006295 polythiol Polymers 0.000 title claims description 30
- 230000005855 radiation Effects 0.000 title claims description 14
- 150000001345 alkine derivatives Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 51
- 239000000565 sealant Substances 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 20
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 11
- 239000000446 fuel Substances 0.000 claims description 9
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 7
- 238000001723 curing Methods 0.000 claims description 5
- 150000001993 dienes Chemical class 0.000 claims description 5
- 150000004662 dithiols Chemical class 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 230000008961 swelling Effects 0.000 claims description 4
- 230000004584 weight gain Effects 0.000 claims description 4
- 235000019786 weight gain Nutrition 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 238000003847 radiation curing Methods 0.000 claims description 2
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 9
- 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 7
- 229920000570 polyether Polymers 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 230000005670 electromagnetic radiation Effects 0.000 description 4
- 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
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 150000003573 thiols Chemical class 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-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
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011521 glass Substances 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
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000002904 solvent Substances 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
- 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
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241001300078 Vitrea Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 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
- 230000009477 glass transition Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 239000013500 performance material Substances 0.000 description 1
- 150000004291 polyenes Chemical class 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
- 229920001289 polyvinyl ether Polymers 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- 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 | |
| US201361779485P | 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 |
|---|---|
| ES2643480T3 true ES2643480T3 (es) | 2017-11-23 |
Family
ID=50382658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14712918.3T Active ES2643480T3 (es) | 2013-03-13 | 2014-03-05 | Politioéteres curables por radiación con enlace a base de alquino |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20160032059A1 (enExample) |
| EP (1) | EP2970589B1 (enExample) |
| JP (1) | JP6463723B2 (enExample) |
| KR (1) | KR20150127635A (enExample) |
| CN (1) | CN105073837B (enExample) |
| BR (1) | BR112015022647A2 (enExample) |
| CA (1) | CA2905328A1 (enExample) |
| ES (1) | ES2643480T3 (enExample) |
| PL (1) | PL2970589T3 (enExample) |
| PT (1) | PT2970589T (enExample) |
| WO (1) | WO2014164103A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2906350A1 (en) * | 2013-03-13 | 2014-10-09 | 3M Innovative Properties Company | Polythioether sealants |
| PL3090006T3 (pl) | 2013-12-30 | 2018-03-30 | 3M Innovative Properties Company | Kompozycje zawierające politiol, nienasycony związek chemiczny i barwnik oraz sposoby powiązane z takimi kompozycjami |
| WO2015102966A1 (en) | 2013-12-30 | 2015-07-09 | 3M Innovative Properties Company | Dye, filler made therefrom, compositions including the filler, and method of determining degree of cure of such compositions |
| EP3237494B1 (en) | 2014-12-23 | 2021-06-16 | 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 |
| US10745558B2 (en) * | 2015-06-29 | 2020-08-18 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
| JP2019521223A (ja) * | 2016-06-30 | 2019-07-25 | スリーエム イノベイティブ プロパティズ カンパニー | ポリチオール、不飽和化合物、光開始剤、及び有機ハイドロパーオキサイドを含む、二元硬化性チオール−エン組成物、並びにそれから調製した航空宇宙産業における使用のための架橋ポリマーシーラント |
| US11198757B2 (en) | 2016-11-03 | 2021-12-14 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and coumarin and related methods |
| JP2019534363A (ja) | 2016-11-03 | 2019-11-28 | スリーエム イノベイティブ プロパティズ カンパニー | シーラントを航空機用部品に適用する方法 |
| JP2020535257A (ja) * | 2017-09-26 | 2020-12-03 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性シーラント組成物、シールキャップ、並びにその作製方法及び使用 |
| PH12020500618B1 (en) * | 2018-01-30 | 2024-02-21 | Namics Corp | Resin composition and cured material of same, adhesive, semiconductor device, and electronic component |
| CN112262014A (zh) | 2018-06-15 | 2021-01-22 | 3M创新有限公司 | 组件和制备垫片的方法 |
| 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 |
| EP4003708A1 (en) | 2019-07-25 | 2022-06-01 | 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 |
| JPH0255732A (ja) * | 1988-08-23 | 1990-02-26 | Mitsubishi Petrochem Co Ltd | 架橋された重合体成形物 |
| JPH0255731A (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 |
| PL334395A1 (en) * | 1997-02-19 | 2000-02-28 | Courtaulds Aerospace | Composition of liquid polythioetheric polymers resisting exposure to fuels and having good flexibility at low temperatures as well as method of obtaining such polymers |
| 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 |
| BR0112023A (pt) * | 2000-06-30 | 2003-05-20 | Prc De Soto International Inc | Formulações vedantes e de envase que incluem polìmeros de terminação mercapto produzidos,pela reação entre um politiol e um monÈmero de éter de polivinila |
| 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 |
| JP4838882B2 (ja) * | 2006-05-05 | 2011-12-14 | ピーピージー インダストリーズ オハイオ，インコーポレイテッド | チオエーテル官能性ポリチオールオリゴマーおよびそれから調製される物品 |
| 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 |
| WO2013021494A1 (ja) * | 2011-08-10 | 2013-02-14 | 電気化学工業株式会社 | 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 CN CN201480013692.1A patent/CN105073837B/zh not_active Expired - Fee Related
- 2014-03-05 PL PL14712918T patent/PL2970589T3/pl unknown
- 2014-03-05 PT PT147129183T patent/PT2970589T/pt unknown
- 2014-03-05 BR BR112015022647A patent/BR112015022647A2/pt not_active Application Discontinuation
- 2014-03-05 EP EP14712918.3A patent/EP2970589B1/en not_active Not-in-force
- 2014-03-05 JP JP2016500637A patent/JP6463723B2/ja not_active Expired - Fee Related
- 2014-03-05 ES ES14712918.3T patent/ES2643480T3/es active Active
- 2014-03-05 KR KR1020157026902A patent/KR20150127635A/ko not_active Ceased
- 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 WO PCT/US2014/020587 patent/WO2014164103A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PL2970589T3 (pl) | 2017-12-29 |
| CN105073837B (zh) | 2017-11-10 |
| JP6463723B2 (ja) | 2019-02-06 |
| EP2970589B1 (en) | 2017-08-02 |
| KR20150127635A (ko) | 2015-11-17 |
| PT2970589T (pt) | 2017-10-23 |
| JP2016512278A (ja) | 2016-04-25 |
| EP2970589A1 (en) | 2016-01-20 |
| BR112015022647A2 (pt) | 2017-07-18 |
| CN105073837A (zh) | 2015-11-18 |
| CA2905328A1 (en) | 2014-10-09 |
| US20160032059A1 (en) | 2016-02-04 |
| WO2014164103A1 (en) | 2014-10-09 |
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