DE2250718A1 - Aus fluorkohlenstoffen bestehende oberflaechenaktive mittel - Google Patents
Aus fluorkohlenstoffen bestehende oberflaechenaktive mittelInfo
- Publication number
- DE2250718A1 DE2250718A1 DE19722250718 DE2250718A DE2250718A1 DE 2250718 A1 DE2250718 A1 DE 2250718A1 DE 19722250718 DE19722250718 DE 19722250718 DE 2250718 A DE2250718 A DE 2250718A DE 2250718 A1 DE2250718 A1 DE 2250718A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- groups
- chain
- stands
- alkyl
- 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.)
- Pending
Links
- 239000004094 surface-active agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 alkylphenoxyl Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 9
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000013256 coordination polymer Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 101001077374 Oryza sativa subsp. japonica UMP-CMP kinase 3 Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000006082 mold release agent Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- XPJRQAIZZQMSCM-UHFFFAOYSA-N heptaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCO XPJRQAIZZQMSCM-UHFFFAOYSA-N 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009736 wetting Methods 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
- C08G65/02—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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4814671 | 1971-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2250718A1 true DE2250718A1 (de) | 1973-04-19 |
Family
ID=10447558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722250718 Pending DE2250718A1 (de) | 1971-10-15 | 1972-10-16 | Aus fluorkohlenstoffen bestehende oberflaechenaktive mittel |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4846583A (enrdf_load_stackoverflow) |
| DE (1) | DE2250718A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2156364A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1354138A (enrdf_load_stackoverflow) |
| IT (1) | IT968823B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2852593A1 (de) * | 1977-12-07 | 1979-06-13 | Ciba Geigy Ag | Fluorierte nichtionische tenside |
| US4170540A (en) * | 1978-03-31 | 1979-10-09 | Hooker Chemicals & Plastics Corp. | Method for forming microporous membrane materials |
| US4289600A (en) * | 1978-03-31 | 1981-09-15 | Hooker Chemicals & Plastics Corp. | Microporous membrane materials |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7401510A (enrdf_load_stackoverflow) * | 1973-02-09 | 1974-08-13 | ||
| JPS5756453B2 (enrdf_load_stackoverflow) * | 1973-10-15 | 1982-11-30 | ||
| JPS50101306A (enrdf_load_stackoverflow) * | 1974-01-22 | 1975-08-11 | ||
| JPS50101307A (enrdf_load_stackoverflow) * | 1974-01-22 | 1975-08-11 | ||
| JPS591319B2 (ja) * | 1975-09-30 | 1984-01-11 | 株式会社ネオス | 含フッ素界面活性剤の製法 |
| US4460791A (en) * | 1978-09-22 | 1984-07-17 | Ciba-Geigy Corporation | Oil recovery by fluorochemical surfactant waterflooding |
| JPS59204144A (ja) * | 1983-04-12 | 1984-11-19 | Daikin Ind Ltd | 新規含フッ素化合物およびその製法 |
| US5154846A (en) * | 1988-12-27 | 1992-10-13 | Allied-Signal Inc. | Fluorinated butylene oxide based refrigerant lubricants |
| US4975212A (en) * | 1988-12-27 | 1990-12-04 | Allied-Signal Inc. | Fluorinated lubricating compositions |
| US5100569A (en) * | 1990-11-30 | 1992-03-31 | Allied-Signal Inc. | Polyoxyalkylene glycol refrigeration lubricants having pendant, non-terminal perfluoroalkyl groups |
| US5658962A (en) | 1994-05-20 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| US7055579B2 (en) | 2003-12-16 | 2006-06-06 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| US7128133B2 (en) | 2003-12-16 | 2006-10-31 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| US6953082B2 (en) | 2003-12-16 | 2005-10-11 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
-
1971
- 1971-10-15 GB GB1354138D patent/GB1354138A/en not_active Expired
-
1972
- 1972-10-10 IT IT3032572A patent/IT968823B/it active
- 1972-10-12 JP JP10161872A patent/JPS4846583A/ja active Pending
- 1972-10-13 FR FR7236408A patent/FR2156364A1/fr not_active Withdrawn
- 1972-10-16 DE DE19722250718 patent/DE2250718A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2852593A1 (de) * | 1977-12-07 | 1979-06-13 | Ciba Geigy Ag | Fluorierte nichtionische tenside |
| US4170540A (en) * | 1978-03-31 | 1979-10-09 | Hooker Chemicals & Plastics Corp. | Method for forming microporous membrane materials |
| US4289600A (en) * | 1978-03-31 | 1981-09-15 | Hooker Chemicals & Plastics Corp. | Microporous membrane materials |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4846583A (enrdf_load_stackoverflow) | 1973-07-03 |
| FR2156364A1 (enrdf_load_stackoverflow) | 1973-05-25 |
| GB1354138A (en) | 1974-06-05 |
| IT968823B (it) | 1974-03-20 |
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