CA2970960A1 - Dual cure polythioether - Google Patents
Dual cure polythioether Download PDFInfo
- Publication number
- CA2970960A1 CA2970960A1 CA2970960A CA2970960A CA2970960A1 CA 2970960 A1 CA2970960 A1 CA 2970960A1 CA 2970960 A CA2970960 A CA 2970960A CA 2970960 A CA2970960 A CA 2970960A CA 2970960 A1 CA2970960 A1 CA 2970960A1
- Authority
- CA
- Canada
- Prior art keywords
- peroxide
- composition according
- amine
- grams
- 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 25
- 230000009977 dual effect Effects 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 150000001412 amines Chemical class 0.000 claims abstract description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 150000002978 peroxides Chemical class 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims abstract description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims abstract description 6
- VDMLVOIDGSOUTA-UHFFFAOYSA-N 2-(4-methylanilino)ethane-1,1-diol Chemical compound CC1=CC=C(NCC(O)O)C=C1 VDMLVOIDGSOUTA-UHFFFAOYSA-N 0.000 claims abstract description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims abstract description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001993 dienes Chemical class 0.000 claims abstract description 5
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012966 redox initiator Substances 0.000 claims abstract description 5
- 150000004662 dithiols Chemical class 0.000 claims abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
- 239000000565 sealant Substances 0.000 claims description 15
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 14
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 7
- 239000002105 nanoparticle Substances 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- 229920002379 silicone rubber Polymers 0.000 description 8
- 239000004945 silicone rubber Substances 0.000 description 8
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 239000008240 homogeneous mixture Substances 0.000 description 6
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000009477 glass transition Effects 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
- 102100025848 Acyl-coenzyme A thioesterase 8 Human genes 0.000 description 2
- 101710175468 Acyl-coenzyme A thioesterase 8 Proteins 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-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
- 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 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-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
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- -1 CMP diene Chemical class 0.000 description 1
- 241000579895 Chlorostilbon Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 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 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 229910052876 emerald Inorganic materials 0.000 description 1
- 239000010976 emerald Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910002011 hydrophilic fumed silica Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- XOTMHFNWERTCLG-UHFFFAOYSA-N tris(4-ethenoxybutyl) benzene-1,2,4-tricarboxylate Chemical compound C=COCCCCOC(=O)C1=CC=C(C(=O)OCCCCOC=C)C(C(=O)OCCCCOC=C)=C1 XOTMHFNWERTCLG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B64—AIRCRAFT; AVIATION; COSMONAUTICS
- B64D—EQUIPMENT FOR FITTING IN OR TO AIRCRAFT; FLIGHT SUITS; PARACHUTES; ARRANGEMENT OR MOUNTING OF POWER PLANTS OR PROPULSION TRANSMISSIONS IN AIRCRAFT
- B64D45/00—Aircraft indicators or protectors not otherwise provided for
- B64D45/02—Lightning protectors; Static dischargers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/04—Polymeric products of isocyanates or isothiocyanates with vinyl 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
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/34—Chemically modified polycondensates by natural resins or resin acids, e.g. rosin
-
- 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
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
-
- 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
- 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
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Aviation & Aerospace Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Sealing Material Composition (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462095952P | 2014-12-23 | 2014-12-23 | |
| US62/095,952 | 2014-12-23 | ||
| PCT/US2015/067450 WO2016106352A1 (en) | 2014-12-23 | 2015-12-22 | Dual cure polythioether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2970960A1 true CA2970960A1 (en) | 2016-06-30 |
Family
ID=55221521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2970960A Abandoned CA2970960A1 (en) | 2014-12-23 | 2015-12-22 | Dual cure polythioether |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US10703906B2 (OSRAM) |
| EP (1) | EP3237494B1 (OSRAM) |
| JP (1) | JP7016698B2 (OSRAM) |
| KR (1) | KR20170097754A (OSRAM) |
| CN (1) | CN107108894B (OSRAM) |
| BR (1) | BR112017013742A2 (OSRAM) |
| CA (1) | CA2970960A1 (OSRAM) |
| WO (1) | WO2016106352A1 (OSRAM) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107108833B (zh) | 2014-11-24 | 2022-06-14 | Ppg工业俄亥俄公司 | 通过挤出用于反应性三维打印的方法 |
| JP6715853B2 (ja) * | 2015-02-13 | 2020-07-01 | スリーエム イノベイティブ プロパティズ カンパニー | 耐寒性シーラント及びその構成成分 |
| US20180127538A1 (en) | 2015-04-29 | 2018-05-10 | 3M Innovative Properties Company | Composition including a polythiol and a polyepoxide and methods relating to the composition |
| 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 |
| EP3535333A1 (en) | 2016-11-03 | 2019-09-11 | 3M Innovative Properties Company | Composition including a polythiol, a polyepoxide, a photolatent base, and an amine and methods relating to the composition |
| CA3042860A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Polythiol sealant compositions |
| EP3535621A1 (en) | 2016-11-03 | 2019-09-11 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and a coumarin and related methods |
| KR102253386B1 (ko) * | 2017-06-09 | 2021-05-17 | 피알시-데소토 인터내쇼날, 인코포레이티드 | 이중 경화 실란트 |
| 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 |
| 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 |
| EP3728506A1 (en) | 2017-12-22 | 2020-10-28 | 3M Innovative Properties Company | Multilayered polyetherketoneketone articles and methods thereof |
| US11648761B2 (en) | 2018-04-17 | 2023-05-16 | 3M Innovative Properties Company | Conductive films |
| EP3802324B1 (en) | 2018-06-07 | 2022-11-30 | 3M Innovative Properties Company | Lightning strike protection film |
| WO2019239273A1 (en) | 2018-06-15 | 2019-12-19 | 3M Innovative Properties Company | Assemblies and methods of making a shim |
| EP3877449A1 (en) * | 2018-11-09 | 2021-09-15 | 3M Innovative Properties Company | Curable sealant compositions, seal cap, and methods of making and using the same |
| CN118082177A (zh) | 2019-02-11 | 2024-05-28 | Ppg工业俄亥俄公司 | 制作耐化学性密封组件的方法 |
| AU2020221901B2 (en) | 2019-02-11 | 2022-07-07 | Ppg Industries Ohio, Inc. | 3D printing of seal caps |
| AU2020221467B2 (en) | 2019-02-11 | 2022-11-17 | Ppg Industries Ohio, Inc. | Multilayer systems and methods of making multilayer systems |
| US11015057B2 (en) * | 2019-04-03 | 2021-05-25 | Prc-Desoto International, Inc. | Dual-cure compositions |
| US12467018B2 (en) | 2019-07-08 | 2025-11-11 | 3M Innovative Properties Company | Cleaning and polishing fluid and method of using |
| WO2021014277A1 (en) | 2019-07-25 | 2021-01-28 | 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 |
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| KR102495856B1 (ko) * | 2022-03-31 | 2023-02-06 | 김용환 | 사상 시스템 |
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| KR20150131076A (ko) | 2013-03-13 | 2015-11-24 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 폴리티오에테르 실란트 |
| CA2905328A1 (en) | 2013-03-13 | 2014-10-09 | 3M Innovative Properties Company | Radiation curable polythioethers with alkyne-based linkage |
| CN105452229B (zh) | 2013-03-15 | 2019-03-12 | 3M创新有限公司 | 作为染料的苯并噻唑-2-基偶氮-苯基化合物，包括该染料的组合物，以及确定此类组合物的固化程度的方法 |
| CA2909377A1 (en) * | 2013-04-15 | 2014-10-23 | 3M Innovative Properties Company | Light weight seal cap |
| US10072135B2 (en) | 2013-12-30 | 2018-09-11 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
-
2015
- 2015-12-22 KR KR1020177020355A patent/KR20170097754A/ko not_active Withdrawn
- 2015-12-22 US US15/533,758 patent/US10703906B2/en active Active
- 2015-12-22 JP JP2017531873A patent/JP7016698B2/ja active Active
- 2015-12-22 BR BR112017013742A patent/BR112017013742A2/pt not_active Application Discontinuation
- 2015-12-22 CN CN201580070296.7A patent/CN107108894B/zh active Active
- 2015-12-22 EP EP15828442.2A patent/EP3237494B1/en active Active
- 2015-12-22 CA CA2970960A patent/CA2970960A1/en not_active Abandoned
- 2015-12-22 WO PCT/US2015/067450 patent/WO2016106352A1/en not_active Ceased
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2020
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|---|---|
| JP2018501356A (ja) | 2018-01-18 |
| EP3237494A1 (en) | 2017-11-01 |
| CN107108894A (zh) | 2017-08-29 |
| WO2016106352A1 (en) | 2016-06-30 |
| US20170362434A1 (en) | 2017-12-21 |
| US20200308403A1 (en) | 2020-10-01 |
| EP3237494B1 (en) | 2021-06-16 |
| JP7016698B2 (ja) | 2022-02-07 |
| CN107108894B (zh) | 2021-04-06 |
| BR112017013742A2 (pt) | 2018-03-13 |
| KR20170097754A (ko) | 2017-08-28 |
| US11319440B2 (en) | 2022-05-03 |
| US10703906B2 (en) | 2020-07-07 |
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