CA2808229C - Fluorinated ethoxylated polyurethanes - Google Patents
Fluorinated ethoxylated polyurethanes Download PDFInfo
- Publication number
- CA2808229C CA2808229C CA2808229A CA2808229A CA2808229C CA 2808229 C CA2808229 C CA 2808229C CA 2808229 A CA2808229 A CA 2808229A CA 2808229 A CA2808229 A CA 2808229A CA 2808229 C CA2808229 C CA 2808229C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- diisocyanate
- liquid
- compound
- perfluoroalkyl
- 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
- 239000004814 polyurethane Substances 0.000 title abstract description 5
- 229920002635 polyurethane Polymers 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000007788 liquid Substances 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 20
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 46
- 239000012530 fluid Substances 0.000 claims description 40
- 239000006260 foam Substances 0.000 claims description 40
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 33
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- 229920000642 polymer Polymers 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
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- 239000001993 wax Substances 0.000 claims description 14
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 13
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 230000003247 decreasing effect Effects 0.000 claims description 7
- 239000004816 latex Substances 0.000 claims description 7
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 6
- 230000000149 penetrating effect Effects 0.000 claims description 5
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- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
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- 230000007797 corrosion Effects 0.000 claims description 2
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- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- XAOJFQKNOVRHCS-UHFFFAOYSA-N 4-isocyanato-2-(isocyanatomethyl)-1,1,2-trimethylcyclohexane Chemical compound CC1(C)CCC(N=C=O)CC1(C)CN=C=O XAOJFQKNOVRHCS-UHFFFAOYSA-N 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 description 52
- 238000000576 coating method Methods 0.000 description 41
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 30
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 30
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 8
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004901 trioxanes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
-
- 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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
-
- 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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K13/00—Etching, surface-brightening or pickling compositions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3726—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Cosmetics (AREA)
- Degasification And Air Bubble Elimination (AREA)
- Detergent Compositions (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/869,897 | 2010-08-27 | ||
| US12/869,897 US9464160B2 (en) | 2010-08-27 | 2010-08-27 | Fluorinated ethoxylated polyurethanes |
| PCT/US2011/049465 WO2012027729A1 (en) | 2010-08-27 | 2011-08-26 | Fluorinated ethoxylated polyurethanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2808229A1 CA2808229A1 (en) | 2012-03-01 |
| CA2808229C true CA2808229C (en) | 2019-03-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2808229A Expired - Fee Related CA2808229C (en) | 2010-08-27 | 2011-08-26 | Fluorinated ethoxylated polyurethanes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9464160B2 (enExample) |
| EP (1) | EP2609130B1 (enExample) |
| JP (1) | JP5978213B2 (enExample) |
| KR (1) | KR101821000B1 (enExample) |
| CN (1) | CN103080176B (enExample) |
| AU (1) | AU2011293133B2 (enExample) |
| CA (1) | CA2808229C (enExample) |
| NZ (1) | NZ606396A (enExample) |
| WO (1) | WO2012027729A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101480179B1 (ko) * | 2011-12-30 | 2015-01-09 | 제일모직주식회사 | Ｃｍｐ 슬러리 조성물 및 이를 이용한 연마 방법 |
| US20150112036A1 (en) * | 2013-10-17 | 2015-04-23 | E I Du Pont De Nemours And Company | Partially fluorinated polymers |
| US10995298B2 (en) | 2014-07-23 | 2021-05-04 | Becton, Dickinson And Company | Self-lubricating polymer composition |
| CN104774604B (zh) * | 2014-10-29 | 2017-09-29 | 中国石油化工股份有限公司 | 一种含氟聚氨酯类co2气溶性发泡剂及其制备方法和用途 |
| MX2017007379A (es) | 2014-12-17 | 2017-11-06 | Dow Global Technologies Llc | Tensioactivos para espumas de poliuretano. |
| KR101807258B1 (ko) | 2016-11-10 | 2017-12-08 | 한국바이오젠 주식회사 | 불소 함유 실릴화 폴리우레탄 감압점착제 및 이의 제조방법 |
| EP3538616B1 (en) * | 2016-11-10 | 2021-01-06 | PPG Coatings Europe B.V. | Surfactants for intumescent foam stabilization |
| KR101879849B1 (ko) * | 2016-11-17 | 2018-07-20 | 황진상 | 고무입자를 포함한 폴리우레탄 접착 수지 조성물 및 이를 이용한 모바일 기기용 접착 테이프 |
| KR101923545B1 (ko) * | 2016-11-17 | 2019-02-28 | 황진상 | 방수성 폴리우레탄 수지 조성물 제조방법 및 이를 이용한 모바일 기기용 접착 테이프 |
| US11613719B2 (en) | 2018-09-24 | 2023-03-28 | Becton, Dickinson And Company | Self-lubricating medical articles |
| CN110105537B (zh) * | 2019-04-25 | 2021-08-13 | 江南大学 | 一种聚氨酯硬泡材料及其制备方法 |
| CN114949372B (zh) | 2021-02-25 | 2023-08-29 | 贝克顿·迪金森公司 | 聚氨酯型医疗制品 |
| CN114957597A (zh) | 2021-02-25 | 2022-08-30 | 贝克顿·迪金森公司 | 聚氨酯型医疗制品 |
| US11739259B1 (en) * | 2022-04-07 | 2023-08-29 | Saudi Arabian Oil Company | Interfacial assembly of integrated silica nanoparticles and fluorosurfactant heterostructures in foamed fracturing fluids |
| CN116715822A (zh) * | 2023-06-01 | 2023-09-08 | 东营众悦石油科技有限公司 | 一种井下作业用起泡剂及其制备方法 |
| CN119613296B (zh) * | 2024-12-05 | 2025-09-19 | 科峻成精密科技(东莞)有限公司 | 金属散热片用蚀刻组合物及其制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2723999A (en) | 1954-01-15 | 1955-11-15 | American Cyanamid Co | Fluorinated alcohol-ethylene oxide condensates |
| US3591547A (en) | 1968-04-12 | 1971-07-06 | Olin Corp | Urethane coating compositions based on polyols prepared from fluorinated glycidyl ethers |
| CA1023768A (en) | 1972-12-21 | 1978-01-03 | Horst Jager | Polyfluoroalkyl iodides, process for their manufacture, and their use |
| JPS5621031B2 (enExample) | 1973-10-03 | 1981-05-16 | ||
| US3952075A (en) | 1973-10-03 | 1976-04-20 | Asahi Denka Kogyo K.K. | Fluorine-containing compounds |
| JPS539204B2 (enExample) | 1973-10-03 | 1978-04-04 | ||
| DE3319368A1 (de) * | 1983-05-27 | 1984-11-29 | Bayer Ag, 5090 Leverkusen | Perfluoralkylgruppen-enthaltende polyurethane und verfahren zu ihrer herstellung |
| JPS63245492A (ja) | 1987-03-31 | 1988-10-12 | Hitachi Maxell Ltd | 潤滑剤とこれを用いた磁気記録媒体 |
| US5107033A (en) | 1988-03-02 | 1992-04-21 | E. I. Du Pont De Nemours And Company | Perfluoroalkyl polyether glycols and their use |
| US4841007A (en) | 1988-03-28 | 1989-06-20 | Becton Dickinson And Company | Fluorinated polyetherurethanes and medical devices therefrom |
| WO1995011877A1 (fr) | 1993-10-27 | 1995-05-04 | Elf Atochem S.A. | Alcools polyfluores et leurs procedes de preparation |
| DE19522476A1 (de) | 1995-06-21 | 1997-01-02 | Bayer Ag | Fluor enthaltende Dispergierhilfsmittel für wäßrige Lacke |
| US5605956A (en) * | 1995-10-16 | 1997-02-25 | E. I. Du Pont De Nemours And Company | Fluorinated polyisocyanates |
| US5597874A (en) | 1995-10-16 | 1997-01-28 | E. I. Du Pont De Nemours And Company | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
| KR20050090233A (ko) | 2004-03-08 | 2005-09-13 | 니카코리아 (주) | 불소계 수분산 우레탄 및 그 제조방법 |
| WO2009029512A2 (en) | 2007-08-24 | 2009-03-05 | Rhodia, Inc. | Two component waterborne polyurethane coatings for anti-graffiti application |
| CN102203153B (zh) | 2008-08-28 | 2014-03-12 | 界面生物公司 | 热稳定的缩二脲和异氰脲酸酯基表面改性大分子及其应用 |
| JP5484716B2 (ja) | 2008-11-26 | 2014-05-07 | 富士フイルム株式会社 | 内燃機関用潤滑剤組成物 |
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2010
- 2010-08-27 US US12/869,897 patent/US9464160B2/en active Active
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2011
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- 2011-08-26 AU AU2011293133A patent/AU2011293133B2/en not_active Ceased
- 2011-08-26 CA CA2808229A patent/CA2808229C/en not_active Expired - Fee Related
- 2011-08-26 JP JP2013526194A patent/JP5978213B2/ja not_active Expired - Fee Related
- 2011-08-26 WO PCT/US2011/049465 patent/WO2012027729A1/en not_active Ceased
- 2011-08-26 KR KR1020137007596A patent/KR101821000B1/ko not_active Expired - Fee Related
- 2011-08-26 NZ NZ606396A patent/NZ606396A/en not_active IP Right Cessation
- 2011-08-26 EP EP11755178.8A patent/EP2609130B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2609130B1 (en) | 2014-11-26 |
| KR20130101518A (ko) | 2013-09-13 |
| CN103080176B (zh) | 2015-11-25 |
| AU2011293133B2 (en) | 2014-05-22 |
| CN103080176A (zh) | 2013-05-01 |
| EP2609130A1 (en) | 2013-07-03 |
| HK1184803A1 (zh) | 2014-01-30 |
| WO2012027729A1 (en) | 2012-03-01 |
| NZ606396A (en) | 2014-07-25 |
| JP2013542177A (ja) | 2013-11-21 |
| US9464160B2 (en) | 2016-10-11 |
| JP5978213B2 (ja) | 2016-08-24 |
| CA2808229A1 (en) | 2012-03-01 |
| US20120053252A1 (en) | 2012-03-01 |
| AU2011293133A1 (en) | 2013-02-21 |
| KR101821000B1 (ko) | 2018-01-22 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20160824 |
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| MKLA | Lapsed |
Effective date: 20220301 |
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| MKLA | Lapsed |
Effective date: 20200831 |