JP4414127B2 - アルキルエーテル末端基を少なくとも有するｐｆｐｅ類及び製造方法 - Google Patents
アルキルエーテル末端基を少なくとも有するｐｆｐｅ類及び製造方法 Download PDFInfo
- Publication number
- JP4414127B2 JP4414127B2 JP2002183282A JP2002183282A JP4414127B2 JP 4414127 B2 JP4414127 B2 JP 4414127B2 JP 2002183282 A JP2002183282 A JP 2002183282A JP 2002183282 A JP2002183282 A JP 2002183282A JP 4414127 B2 JP4414127 B2 JP 4414127B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- ocf
- perfluoropolyether
- compound
- distillate
- 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
- 238000004519 manufacturing process Methods 0.000 title description 6
- 125000005011 alkyl ether group Chemical group 0.000 title 1
- 239000010702 perfluoropolyether Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 37
- -1 alkyl sulfite Chemical compound 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 2
- 150000003841 chloride salts Chemical group 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000002978 peroxides Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 8
- 229920002492 poly(sulfone) Polymers 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000000711 cancerogenic effect Effects 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007539 photo-oxidation reaction Methods 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 150000005215 alkyl ethers Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VQUGQIYAVYQSAB-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-(1,2,2-trifluoroethenoxy)ethanesulfonyl fluoride Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)S(F)(=O)=O VQUGQIYAVYQSAB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002081 peroxide group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- 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
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/206664—Ozone or peroxide
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)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Semiconductor Memories (AREA)
- Non-Volatile Memory (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI001340A ITMI20011340A1 (it) | 2001-06-26 | 2001-06-26 | Pfpe aventi almeno un terminale alchiletereo e relativo processo dipreparazione |
| IT2001A001340 | 2001-06-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003064018A JP2003064018A (ja) | 2003-03-05 |
| JP2003064018A5 JP2003064018A5 (enExample) | 2005-09-22 |
| JP4414127B2 true JP4414127B2 (ja) | 2010-02-10 |
Family
ID=11447932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002183282A Expired - Fee Related JP4414127B2 (ja) | 2001-06-26 | 2002-06-24 | アルキルエーテル末端基を少なくとも有するｐｆｐｅ類及び製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US6982173B2 (enExample) |
| EP (2) | EP1275678B1 (enExample) |
| JP (1) | JP4414127B2 (enExample) |
| DE (2) | DE60230938D1 (enExample) |
| IT (1) | ITMI20011340A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20030372A1 (it) * | 2003-03-03 | 2004-09-04 | Solvay Solexis Spa | Perfluoropolieteri lineari aventi migliorata stabilita' termoossidativa. |
| US7544646B2 (en) | 2004-10-06 | 2009-06-09 | Thomas Michael Band | Method for lubricating a sootblower |
| US7581585B2 (en) * | 2004-10-29 | 2009-09-01 | 3M Innovative Properties Company | Variable position cooling apparatus |
| US20060090881A1 (en) * | 2004-10-29 | 2006-05-04 | 3M Innovative Properties Company | Immersion cooling apparatus |
| JP4828114B2 (ja) * | 2004-11-15 | 2011-11-30 | 富士通株式会社 | 組成物を含む潤滑剤、磁気記録媒体、ヘッドスライダおよび磁気記録装置 |
| US7385089B2 (en) * | 2005-12-23 | 2008-06-10 | 3M Innovative Properties Company | Fluorochemical ketone compounds and processes for their use |
| AU2013201452B2 (en) * | 2006-01-13 | 2016-01-07 | The Chemours Company Fc, Llc. | Refrigerant additive compositions containing perfluoropolyethers |
| US8188323B2 (en) * | 2006-01-13 | 2012-05-29 | E.I. Du Pont De Nemours And Company | Refrigerant compositions containing perfluoropolyethers |
| EP1979432B1 (en) * | 2006-01-13 | 2018-12-05 | The Chemours Company FC, LLC | Refrigerant additive compositions containing perfluoropolyethers |
| US7759532B2 (en) | 2006-01-13 | 2010-07-20 | E.I. Du Pont De Nemours And Company | Refrigerant additive compositions containing perfluoropolyethers |
| ITMI20060381A1 (it) * | 2006-03-02 | 2007-09-03 | Solvay Solexis Spa | Fluidi di scambio termico |
| EP2069455A1 (en) | 2006-09-01 | 2009-06-17 | E.I. Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| JP5258779B2 (ja) * | 2006-11-30 | 2013-08-07 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | フッ素化潤滑剤 |
| ITMI20062308A1 (it) * | 2006-11-30 | 2008-06-01 | Solvay Solexis Spa | Additivi per alo-polimeri |
| JP5347242B2 (ja) * | 2007-06-04 | 2013-11-20 | Ｄｉｃ株式会社 | グリース基油拡散防止剤 |
| EP2025731A1 (en) * | 2007-08-06 | 2009-02-18 | Solvay Solexis S.p.A. | Heat Transfer fluid |
| JP5591806B2 (ja) * | 2008-09-26 | 2014-09-17 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | 熱伝達方法 |
| EP2370269B1 (en) * | 2008-12-11 | 2015-08-05 | 3M Innovative Properties Company | Patterning process |
| US8329830B2 (en) | 2009-06-30 | 2012-12-11 | 3M Innovative Properties Company | Surface treatment process and treated article |
| WO2011079020A1 (en) | 2009-12-22 | 2011-06-30 | 3M Innovative Properties Company | Process for preparing shelf-stable curable polysilazanes, and polysilazanes prepared thereby |
| US9153268B1 (en) | 2013-02-19 | 2015-10-06 | WD Media, LLC | Lubricants comprising fluorinated graphene nanoribbons for magnetic recording media structure |
| CN104085225B (zh) * | 2014-05-30 | 2016-04-20 | 刘保伸 | 便于握持的异轴笔 |
| CN104132472B (zh) * | 2014-07-16 | 2017-03-29 | 广东美芝制冷设备有限公司 | 空调系统 |
| CN104101138B (zh) * | 2014-07-16 | 2017-03-29 | 广东美芝制冷设备有限公司 | 空调系统 |
| KR102268129B1 (ko) | 2017-10-16 | 2021-06-22 | 주식회사 엘지화학 | 비반응성 불소계 화합물 및 이를 포함하는 광중합성 조성물 |
| CN115651186B (zh) * | 2022-11-08 | 2024-05-14 | 浙江巨化技术中心有限公司 | 一种制备全氟聚醚酸的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| NL6709067A (enExample) | 1964-04-09 | 1968-01-08 | ||
| US4094911A (en) * | 1969-03-10 | 1978-06-13 | Minnesota Mining And Manufacturing Company | Poly(perfluoroalkylene oxide) derivatives |
| US4453018A (en) * | 1982-04-01 | 1984-06-05 | International Telephone And Telegraph Corporation | Process for the alkylation of phenolic compounds with alkyl sulfites |
| US5202480A (en) * | 1988-09-28 | 1993-04-13 | Exfluor Research Corporation | Fluorination of acetals, ketals and orthoesters |
| US5539059A (en) * | 1988-09-28 | 1996-07-23 | Exfluor Research Corporation | Perfluorinated polyethers |
| JPH0531801Y2 (enExample) * | 1990-01-29 | 1993-08-16 | ||
| US5237108A (en) * | 1990-03-06 | 1993-08-17 | Ausimont S.R.L. | Perfluoropolyethers and processes for their preparation |
| US5305221A (en) * | 1990-05-04 | 1994-04-19 | Atherton Robert W | Real world modeling and control process for integrated manufacturing equipment |
| JPH04110386A (ja) | 1990-08-31 | 1992-04-10 | Daikin Ind Ltd | 熱伝達用流体 |
| IT1249319B (it) * | 1991-04-26 | 1995-02-22 | Ausimont Spa | Perfluoropolieteri ad elevata viscosita' e basso contenuto di ossigeno perossidico, e procedimento per la loro preparazione |
| US5382704A (en) * | 1993-06-30 | 1995-01-17 | E. I. Du Pont De Nemours And Company | Fluorinated methyl ethers |
| GB9326354D0 (en) * | 1993-12-23 | 1994-02-23 | British Aerospace | Methods and apparatus for the testing,monitoring and improvement of manufacturing process effectiveness |
| US6240328B1 (en) * | 1994-01-10 | 2001-05-29 | Motorola, Inc. | Manufacturing method for assembling products by generating and scheduling dynamically assembly instructions |
| US5444632A (en) * | 1994-04-28 | 1995-08-22 | Texas Instruments Incorporated | Apparatus and method for controlling and scheduling processing machines |
| IT1274591B (it) | 1994-08-05 | 1997-07-18 | Ausimont Spa | Processo per la preparazione di poliossiperfluoroalcani idrogeno terminati |
| US5718293A (en) | 1995-01-20 | 1998-02-17 | Minnesota Mining And Manufacturing Company | Fire extinguishing process and composition |
| US5546326A (en) * | 1995-04-04 | 1996-08-13 | Taiwan Semiconductor Manufacturing Company Ltd | Dynamic dispatching rule that uses long term due date and short term queue time to improve delivery performance |
| IT1282626B1 (it) * | 1996-02-14 | 1998-03-31 | Ausimont Spa | Processo di preparazione di perfluoropolieteri perossidici |
| IT1282627B1 (it) * | 1996-02-14 | 1998-03-31 | Ausimont Spa | Procedimento per la preparazione di perfluoropoliossialchileni perossidici |
| US5781454A (en) * | 1996-03-25 | 1998-07-14 | Raytheon Company | Process modeling technique |
| US5750797A (en) * | 1996-04-15 | 1998-05-12 | Minnesota Mining And Manufacturing Company | Process for the production of hydrofluoroethers |
| IT1313597B1 (it) * | 1999-08-04 | 2002-09-09 | Ausimont Spa | Lubrificanti perfluoropolieterei contenenti gruppi solfonilfluoruro |
-
2001
- 2001-06-26 IT IT2001MI001340A patent/ITMI20011340A1/it unknown
-
2002
- 2002-06-21 DE DE60230938T patent/DE60230938D1/de not_active Expired - Fee Related
- 2002-06-21 EP EP02013790A patent/EP1275678B1/en not_active Expired - Lifetime
- 2002-06-21 EP EP06010608A patent/EP1690911B1/en not_active Expired - Lifetime
- 2002-06-21 DE DE60213723T patent/DE60213723T2/de not_active Expired - Lifetime
- 2002-06-24 JP JP2002183282A patent/JP4414127B2/ja not_active Expired - Fee Related
- 2002-06-26 US US10/179,977 patent/US6982173B2/en not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| US7488852B2 (en) | 2009-02-10 |
| US6982173B2 (en) | 2006-01-03 |
| ITMI20011340A0 (it) | 2001-06-26 |
| US20060264682A1 (en) | 2006-11-23 |
| EP1690911B1 (en) | 2009-01-14 |
| EP1690911A1 (en) | 2006-08-16 |
| DE60213723D1 (de) | 2006-09-21 |
| US20050250964A1 (en) | 2005-11-10 |
| JP2003064018A (ja) | 2003-03-05 |
| DE60213723T2 (de) | 2007-09-06 |
| EP1275678B1 (en) | 2006-08-09 |
| EP1275678A2 (en) | 2003-01-15 |
| EP1275678A3 (en) | 2003-04-23 |
| US7115783B2 (en) | 2006-10-03 |
| US20030013923A1 (en) | 2003-01-16 |
| ITMI20011340A1 (it) | 2002-12-26 |
| DE60230938D1 (de) | 2009-03-05 |
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