JP3310439B2 - ヒドロキシル基および／またはメルカプト基を含むフオスフオノ−およびフオスフイノカルボン酸のフッ素化されたカルボン酸エステル、その製造法、および使用法 - Google Patents
ヒドロキシル基および／またはメルカプト基を含むフオスフオノ−およびフオスフイノカルボン酸のフッ素化されたカルボン酸エステル、その製造法、および使用法Info
- Publication number
- JP3310439B2 JP3310439B2 JP01205594A JP1205594A JP3310439B2 JP 3310439 B2 JP3310439 B2 JP 3310439B2 JP 01205594 A JP01205594 A JP 01205594A JP 1205594 A JP1205594 A JP 1205594A JP 3310439 B2 JP3310439 B2 JP 3310439B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- linear
- carbon atoms
- branched
- phosphono
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims description 37
- 125000003396 thiol group Chemical group [H]S* 0.000 title claims description 33
- MEUIIHOXOWVKNP-UHFFFAOYSA-N phosphanylformic acid Chemical class OC(P)=O MEUIIHOXOWVKNP-UHFFFAOYSA-N 0.000 title claims description 30
- 150000001733 carboxylic acid esters Chemical class 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 238000004078 waterproofing Methods 0.000 claims description 5
- 239000010985 leather Substances 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000011111 cardboard Substances 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000007040 multi-step synthesis reaction Methods 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- DSRUAYIFDCHEEV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(2-hydroxyethyl)-n-methylbutane-1-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DSRUAYIFDCHEEV-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 239000004519 grease Substances 0.000 description 4
- -1 perfluoro groups Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- PLGACQRCZCVKGK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-n-(2-hydroxyethyl)-n-methyloctane-1-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PLGACQRCZCVKGK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- GPXCJKUXBIGASD-UHFFFAOYSA-N 1-phosphonobutane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)C(C(O)=O)P(O)(O)=O GPXCJKUXBIGASD-UHFFFAOYSA-N 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DLEPCXYNAPUMDZ-UHFFFAOYSA-N butan-2-ylphosphonic acid Chemical compound CCC(C)P(O)(O)=O DLEPCXYNAPUMDZ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
- D06M13/29—Phosphonic or phosphonous acids or derivatives thereof containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/36—Hydrogen production from non-carbon containing sources, e.g. by water electrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4300800A DE4300800C2 (de) | 1993-01-14 | 1993-01-14 | Hydroxy- und/oder mercaptogruppenhaltige fluorierte Carbonsäureester von Phosphono- und Phosphinocarbonsäuren, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| DE4300800.3 | 1993-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06279469A JPH06279469A (ja) | 1994-10-04 |
| JP3310439B2 true JP3310439B2 (ja) | 2002-08-05 |
Family
ID=6478182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP01205594A Expired - Fee Related JP3310439B2 (ja) | 1993-01-14 | 1994-01-10 | ヒドロキシル基および／またはメルカプト基を含むフオスフオノ−およびフオスフイノカルボン酸のフッ素化されたカルボン酸エステル、その製造法、および使用法 |
Country Status (9)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6646088B2 (en) | 2000-08-16 | 2003-11-11 | 3M Innovative Properties Company | Urethane-based stain-release coatings |
| DE10101190A1 (de) * | 2001-01-12 | 2002-08-01 | Clariant Gmbh | Verwendung einer Pulver-Zusammensetzung zur Hydrophobierung von Baustoffmassen |
| US6803109B2 (en) | 2001-03-09 | 2004-10-12 | 3M Innovative Properties Company | Water-and oil-repellency imparting urethane oligomers comprising perfluoroalkyl moieties |
| US6753380B2 (en) | 2001-03-09 | 2004-06-22 | 3M Innovative Properties Company | Water-and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
| US6890360B2 (en) | 2001-12-17 | 2005-05-10 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
| US20040147188A1 (en) * | 2003-01-28 | 2004-07-29 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
| US20070014927A1 (en) * | 2005-07-15 | 2007-01-18 | Buckanin Richard S | Fluorochemical urethane composition for treatment of fibrous substrates |
| US7459186B2 (en) | 2005-08-05 | 2008-12-02 | Wacker Chemical Corporation | Masonry sealing compositions comprising semi-crystalline ethylene-vinyl acetate polymer emulsions |
| US8338517B2 (en) * | 2007-05-23 | 2012-12-25 | 3M Innovative Properties Company | Aqueous compositions of fluorinated surfactants and methods of using the same |
| CN101679548B (zh) | 2007-06-06 | 2012-07-18 | 3M创新有限公司 | 氟化组合物以及由其制备的表面处理剂 |
| EP2160421A1 (en) * | 2007-06-06 | 2010-03-10 | 3M Innovative Properties Company | Fluorinated ether compositions and methods of using the same |
| JP2010529263A (ja) * | 2007-06-08 | 2010-08-26 | スリーエム イノベイティブ プロパティズ カンパニー | ペルフルオロアルキル部分を含む撥水性及び撥油性付与エステルオリゴマー |
| US8993116B2 (en) * | 2007-06-08 | 2015-03-31 | 3M Innovative Properties Company | Blends of fluoroalkyl-containing ester oligomers with polydicarbodiimide(S) |
| CN102149674A (zh) * | 2008-07-18 | 2011-08-10 | 3M创新有限公司 | 氟化醚化合物及其使用方法 |
| CN102282191A (zh) * | 2008-11-25 | 2011-12-14 | 3M创新有限公司 | 氟化醚尿烷及其使用方法 |
| CN102333841B (zh) | 2008-12-18 | 2014-11-26 | 3M创新有限公司 | 使含烃地层与氟化磷酸酯和膦酸酯组合物接触的方法 |
| US8629089B2 (en) | 2008-12-18 | 2014-01-14 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| CN117004122A (zh) * | 2023-09-04 | 2023-11-07 | 吴江市拓研电子材料有限公司 | 一种耐高温耐油铁氟龙扎带及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424243A1 (de) | 1974-05-18 | 1975-11-27 | Bayer Ag | Perfluoralkansulfonamidoalkanphosphonsaeure- bzw. -phosphinsaeurederivate |
| DE2439281A1 (de) | 1974-08-16 | 1976-02-26 | Henkel & Cie Gmbh | Beta-trifluormethyl-beta-phosphonobuttersaeure und derivate |
| US4293441A (en) | 1979-03-12 | 1981-10-06 | Minnesota Mining And Manufacturing Company | Corrosion inhibiting heat transfer liquid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4602092A (en) * | 1983-09-19 | 1986-07-22 | E. R. Squibb & Sons, Inc. | Method for making phosphinic acid intermediates |
| DE3605800A1 (de) * | 1986-02-22 | 1987-08-27 | Bayer Ag | 2-phosphonobutan-1,2,4-tricarbonsaeurederivate als emulgatoren |
-
1993
- 1993-01-14 DE DE4300800A patent/DE4300800C2/de not_active Expired - Fee Related
- 1993-12-17 TW TW082110701A patent/TW271447B/zh active
- 1993-12-23 US US08/172,274 patent/US5424474A/en not_active Expired - Fee Related
-
1994
- 1994-01-03 EP EP94100003A patent/EP0606831B1/de not_active Expired - Lifetime
- 1994-01-03 DE DE59408219T patent/DE59408219D1/de not_active Expired - Fee Related
- 1994-01-03 ES ES94100003T patent/ES2133422T3/es not_active Expired - Lifetime
- 1994-01-10 JP JP01205594A patent/JP3310439B2/ja not_active Expired - Fee Related
- 1994-01-11 CA CA002113239A patent/CA2113239A1/en not_active Abandoned
- 1994-01-13 KR KR1019940000456A patent/KR940018390A/ko not_active Ceased
- 1994-01-14 CN CN94100611A patent/CN1042634C/zh not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424243A1 (de) | 1974-05-18 | 1975-11-27 | Bayer Ag | Perfluoralkansulfonamidoalkanphosphonsaeure- bzw. -phosphinsaeurederivate |
| DE2439281A1 (de) | 1974-08-16 | 1976-02-26 | Henkel & Cie Gmbh | Beta-trifluormethyl-beta-phosphonobuttersaeure und derivate |
| US4293441A (en) | 1979-03-12 | 1981-10-06 | Minnesota Mining And Manufacturing Company | Corrosion inhibiting heat transfer liquid |
Also Published As
| Publication number | Publication date |
|---|---|
| KR940018390A (ko) | 1994-08-16 |
| EP0606831A1 (de) | 1994-07-20 |
| US5424474A (en) | 1995-06-13 |
| DE4300800C2 (de) | 1996-09-19 |
| CN1096788A (zh) | 1994-12-28 |
| JPH06279469A (ja) | 1994-10-04 |
| DE59408219D1 (de) | 1999-06-17 |
| CN1042634C (zh) | 1999-03-24 |
| DE4300800A1 (de) | 1994-07-21 |
| TW271447B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-03-01 |
| ES2133422T3 (es) | 1999-09-16 |
| CA2113239A1 (en) | 1994-07-15 |
| EP0606831B1 (de) | 1999-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |