JP6189930B2 - ポリチオエーテル系シーラント - Google Patents
ポリチオエーテル系シーラント Download PDFInfo
- Publication number
- JP6189930B2 JP6189930B2 JP2015504641A JP2015504641A JP6189930B2 JP 6189930 B2 JP6189930 B2 JP 6189930B2 JP 2015504641 A JP2015504641 A JP 2015504641A JP 2015504641 A JP2015504641 A JP 2015504641A JP 6189930 B2 JP6189930 B2 JP 6189930B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- grams
- polythioether
- curable
- monomer
- 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.)
- Expired - Fee Related
Links
- 229920006295 polythiol Polymers 0.000 title claims description 51
- 239000000565 sealant Substances 0.000 title description 22
- 239000000203 mixture Substances 0.000 claims description 98
- 239000000178 monomer Substances 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 26
- 230000005855 radiation Effects 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 150000004662 dithiols Chemical class 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims 1
- IFBMOBFQBJZBMV-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphanyl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C IFBMOBFQBJZBMV-UHFFFAOYSA-N 0.000 claims 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 17
- 239000000945 filler Substances 0.000 description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000002105 nanoparticle Substances 0.000 description 8
- 239000000446 fuel Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 230000004584 weight gain Effects 0.000 description 4
- 235000019786 weight gain Nutrition 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 238000000034 method Methods 0.000 description 3
- 238000003847 radiation curing Methods 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical group CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 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
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000009477 glass transition Effects 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
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 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
- 239000005060 rubber 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
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 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
- C08G75/02—Polythioethers
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261619178P | 2012-04-02 | 2012-04-02 | |
| US61/619,178 | 2012-04-02 | ||
| US201361779393P | 2013-03-13 | 2013-03-13 | |
| US61/779,393 | 2013-03-13 | ||
| PCT/US2013/034623 WO2013151893A2 (en) | 2012-04-02 | 2013-03-29 | Polythioether sealants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015517012A JP2015517012A (ja) | 2015-06-18 |
| JP2015517012A5 JP2015517012A5 (enExample) | 2016-04-21 |
| JP6189930B2 true JP6189930B2 (ja) | 2017-08-30 |
Family
ID=48096324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015504641A Expired - Fee Related JP6189930B2 (ja) | 2012-04-02 | 2013-03-29 | ポリチオエーテル系シーラント |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20150065600A1 (enExample) |
| EP (1) | EP2834287B1 (enExample) |
| JP (1) | JP6189930B2 (enExample) |
| KR (1) | KR20140146145A (enExample) |
| CN (1) | CN104812806A (enExample) |
| CA (1) | CA2869325A1 (enExample) |
| WO (1) | WO2013151893A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2906350A1 (en) * | 2013-03-13 | 2014-10-09 | 3M Innovative Properties Company | Polythioether sealants |
| 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 |
| 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 |
| EP3237494B1 (en) | 2014-12-23 | 2021-06-16 | 3M Innovative Properties Company | Dual cure polythioether |
| EP3256542B1 (de) * | 2015-02-13 | 2022-07-06 | Chemetall GmbH | Dichtmasse auf basis von mercaptoterminiertem basispolymer/epoxidverbindung und verfahren zum härten mittels eines photolatenten katalysators |
| 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 |
| 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 |
| US11198757B2 (en) | 2016-11-03 | 2021-12-14 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and coumarin and related methods |
| WO2018085190A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Polythiol sealant compositions |
| US10591950B2 (en) | 2017-04-19 | 2020-03-17 | United States Of America As Represented By The Secretary Of The Army | Copolymerized bis-(ethylene oxy) methane polysulfide polymer and hydroxyl terminated poly butadiene as a solid fueled ramjet fuel |
| CN107312174B (zh) * | 2017-07-19 | 2019-10-18 | 北京化工大学 | 一种聚硫醚的合成方法 |
| 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 |
| EP4003708A1 (en) | 2019-07-25 | 2022-06-01 | 3M Innovative Properties Company | Methods of shimming an assembly |
| CN110903479A (zh) * | 2019-12-02 | 2020-03-24 | 锦西化工研究院有限公司 | 一种用作聚硫密封剂增塑剂的硫醚聚合物的制备方法 |
| CN111944392B (zh) * | 2020-08-25 | 2021-08-24 | 江南大学 | 一种超支化聚硫醚/环氧丙烯酸酯树脂复合光固化涂料及其制备方法和应用 |
| CN114031775B (zh) * | 2021-09-27 | 2023-07-07 | 武汉纺织大学 | 绿色无溶剂生物基抗菌胶粘剂及其制备方法 |
| CN115678011B (zh) * | 2022-11-11 | 2024-09-10 | 赛感科技(深圳)有限公司 | 聚硫醚弹性体及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9708589A (pt) * | 1996-04-05 | 1999-08-03 | Minnesota Mining & Mfg | Composição polimerizável por luz visível e processos para revestir um substrato com um revestimento protetor e para reparar um defeito em um substrato revestido |
| 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 |
| 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 |
| US6509418B1 (en) * | 1997-02-19 | 2003-01-21 | Prc-Desoto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
| 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 |
| SE522479C2 (sv) * | 2002-01-16 | 2004-02-10 | Ericsson Telefon Ab L M | Sammansatt effektförstärkare |
| 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 |
| US7390859B2 (en) * | 2005-02-08 | 2008-06-24 | Ppg Industries Ohio, Inc. | Compositions and methods of making compositions exhibiting fuel resistance |
| US20110319559A1 (en) * | 2010-06-25 | 2011-12-29 | PRC-DeSolo International, Inc. | Polythioether polymers, methods for preparation thereof, and compositions comprising them |
| US8729198B2 (en) * | 2010-08-13 | 2014-05-20 | Prc Desoto International, Inc. | Compositions comprising thiol-terminated polymers and sulfur-containing ethylenically unsaturated silanes and related cured sealants |
| US8932685B2 (en) * | 2010-08-13 | 2015-01-13 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
-
2013
- 2013-03-29 KR KR1020147030228A patent/KR20140146145A/ko not_active Ceased
- 2013-03-29 WO PCT/US2013/034623 patent/WO2013151893A2/en not_active Ceased
- 2013-03-29 CA CA2869325A patent/CA2869325A1/en not_active Abandoned
- 2013-03-29 US US14/389,905 patent/US20150065600A1/en not_active Abandoned
- 2013-03-29 EP EP13716668.2A patent/EP2834287B1/en not_active Not-in-force
- 2013-03-29 CN CN201380018818.XA patent/CN104812806A/zh active Pending
- 2013-03-29 JP JP2015504641A patent/JP6189930B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2869325A1 (en) | 2013-10-10 |
| US20150065600A1 (en) | 2015-03-05 |
| EP2834287B1 (en) | 2021-09-08 |
| WO2013151893A3 (en) | 2014-02-20 |
| KR20140146145A (ko) | 2014-12-24 |
| CN104812806A (zh) | 2015-07-29 |
| EP2834287A2 (en) | 2015-02-11 |
| JP2015517012A (ja) | 2015-06-18 |
| WO2013151893A2 (en) | 2013-10-10 |
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