DD259849A5 - Verfahren zur herstellung von perfluoralkylgruppen, epichlorhydringruppen und dialkoholreste enthaltenden urethanen und ihre verwendung - Google Patents
Verfahren zur herstellung von perfluoralkylgruppen, epichlorhydringruppen und dialkoholreste enthaltenden urethanen und ihre verwendung Download PDFInfo
- Publication number
- DD259849A5 DD259849A5 DD86296171A DD29617186A DD259849A5 DD 259849 A5 DD259849 A5 DD 259849A5 DD 86296171 A DD86296171 A DD 86296171A DD 29617186 A DD29617186 A DD 29617186A DD 259849 A5 DD259849 A5 DD 259849A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- adduct
- formula
- epichlorohydrin
- groups
- perfluoroalkyl
- Prior art date
Links
- 150000003673 urethanes Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 13
- 239000012948 isocyanate Substances 0.000 claims abstract description 25
- 239000004753 textile Substances 0.000 claims abstract description 25
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 21
- -1 urethane compound Chemical class 0.000 claims abstract description 21
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 239000011737 fluorine Substances 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000002209 hydrophobic effect Effects 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 58
- 239000000203 mixture Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 28
- 239000004744 fabric Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 150000002009 diols Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 229920000909 polytetrahydrofuran Polymers 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000013065 commercial product Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WKIWNEKYNOOPRL-UHFFFAOYSA-N 2,5-bis(chloromethyl)-1,4-dioxane Chemical compound ClCC1COC(CCl)CO1 WKIWNEKYNOOPRL-UHFFFAOYSA-N 0.000 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 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical group ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 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 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- MCVKSYYBBHNAFN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO MCVKSYYBBHNAFN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- CWHYTESDVACLIN-UHFFFAOYSA-N 3-chlorobutane-1,2-diol Chemical compound CC(Cl)C(O)CO CWHYTESDVACLIN-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241001091551 Clio Species 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- OXEMATRCWUHWJV-UHFFFAOYSA-N decane;hexane Chemical compound CCCCCC.CCCCCCCCCC OXEMATRCWUHWJV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/58—Y being a hetero atom
- C07C275/62—Y being a nitrogen atom, e.g. biuret
-
- 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
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyethers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853540147 DE3540147A1 (de) | 1985-11-13 | 1985-11-13 | Perfluoralkylgruppen, epichlorhydringruppen und dialkoholreste enthaltende urethane, verfahren zu ihrer herstellung und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD259849A5 true DD259849A5 (de) | 1988-09-07 |
Family
ID=6285803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86296171A DD259849A5 (de) | 1985-11-13 | 1986-11-11 | Verfahren zur herstellung von perfluoralkylgruppen, epichlorhydringruppen und dialkoholreste enthaltenden urethanen und ihre verwendung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4766234A (fr) |
| EP (1) | EP0222334B1 (fr) |
| JP (1) | JPH0811748B2 (fr) |
| KR (1) | KR940008917B1 (fr) |
| AT (1) | ATE66914T1 (fr) |
| AU (1) | AU589232B2 (fr) |
| BR (1) | BR8605583A (fr) |
| CA (1) | CA1276164C (fr) |
| DD (1) | DD259849A5 (fr) |
| DE (2) | DE3540147A1 (fr) |
| ES (1) | ES2026445T3 (fr) |
| SU (1) | SU1445555A3 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3622284A1 (de) * | 1986-07-03 | 1988-01-07 | Hoechst Ag | Urethane aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3722375A1 (de) * | 1987-07-07 | 1989-01-19 | Hoechst Ag | Fluor und polysiloxan enthaltende urethane, verfahren zu ihrer herstellung und ihre verwendung |
| DE3943127A1 (de) * | 1989-12-28 | 1991-07-04 | Hoechst Ag | Urethane als aliphatischen fluoralkoholen, isocyanaten und carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung |
| CA2032813C (fr) * | 1989-12-29 | 2002-09-24 | Jack R. Kirchner | Composes organiques azotes polyfluores |
| US5276175A (en) * | 1991-04-02 | 1994-01-04 | Minnesota Mining And Manufacturing Company | Isocyanate derivatives comprising flourochemical oligomers |
| DE4431467A1 (de) * | 1994-09-03 | 1996-03-07 | Basf Ag | Caramoylcarbonsäureamide |
| DE19610111A1 (de) * | 1996-03-14 | 1997-09-18 | Wacker Chemie Gmbh | Zusammensetzungen für die wasser- und ölabweisende Behandlung saugfähiger Materialien |
| DE19634500A1 (de) * | 1996-08-26 | 1998-03-05 | Wacker Chemie Gmbh | Zusammensetzungen für die wasser- und ölabweisende Behandlung saugfähiger Materialien |
| US7169858B2 (en) * | 2003-02-27 | 2007-01-30 | Cognis Corporation | Polyfluorinated compounds useful as surfactants, foam control agents and/or rheology modifiers |
| CN103342814B (zh) * | 2013-07-19 | 2015-07-29 | 湖南工程学院 | 一种含短氟碳链涂层整理剂及其制备方法和应用 |
| CN110770271B (zh) * | 2017-05-19 | 2023-04-18 | 埃特纳科技有限公司 | 官能化氟化单体的制备方法、氟化单体及用于制备其的组合物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681426A (en) * | 1968-08-30 | 1972-08-01 | Hoechst Ag | Fluorinated polymers having bisurethano side chains |
| US3657320A (en) * | 1968-11-08 | 1972-04-18 | Allied Chem | Perfluoroalkoxyalkyl-substituted carbamates |
| BE756287A (fr) * | 1969-09-17 | 1971-03-17 | Hoechst Ag | Produits de polyaddition d'ethylene-imines utilisables pour l'appretagede textiles |
| US4289892A (en) * | 1970-03-03 | 1981-09-15 | Minnesota Mining And Manufacturing Company | Fluorochemical foam stabilizer and foamed polyurethanes made therewith |
| US3952075A (en) * | 1973-10-03 | 1976-04-20 | Asahi Denka Kogyo K.K. | Fluorine-containing compounds |
| US3994951A (en) * | 1975-07-17 | 1976-11-30 | Pennwalt Corporation | Polyoxyalkylene fluoroalkyltrimellitates |
| US4264484A (en) * | 1979-01-24 | 1981-04-28 | Minnesota Mining And Manufacturing Company | Carpet treatment |
| US4340749A (en) * | 1979-12-21 | 1982-07-20 | Minnesota Mining And Manufacturing Company | Carpet treatment |
| US4321404A (en) * | 1980-05-20 | 1982-03-23 | Minnesota Mining And Manufacturing Company | Compositions for providing abherent coatings |
| US4468527A (en) * | 1980-12-08 | 1984-08-28 | Minnesota Mining And Manufacturing Company | Fluorinated alcohols |
| US4525305A (en) * | 1982-10-25 | 1985-06-25 | Minnesota Mining And Manufacturing Company | Leather with fluorochemical finish |
| US4958039A (en) * | 1984-08-24 | 1990-09-18 | E. I. Du Pont De Nemours And Company | Modified fluorocarbonylimino biurets |
| DE3530967A1 (de) * | 1985-08-30 | 1987-03-05 | Hoechst Ag | Perfluoralkyl- und epichlorhydrin-gruppen enthaltende urethane, diese urethane enthaltende waessrige dispersionen und ihre verwendung |
| DE3672718D1 (de) * | 1985-08-30 | 1990-08-23 | Hoechst Ag | Perfluoralkyl- und epichlorhydrin-gruppen enthaltende urethane, diese urethane enthaltende waessrige dispersionen und ihre verwendung. |
-
1985
- 1985-11-13 DE DE19853540147 patent/DE3540147A1/de not_active Withdrawn
-
1986
- 1986-11-07 DE DE8686115437T patent/DE3681250D1/de not_active Expired - Lifetime
- 1986-11-07 AT AT86115437T patent/ATE66914T1/de not_active IP Right Cessation
- 1986-11-07 EP EP86115437A patent/EP0222334B1/fr not_active Expired - Lifetime
- 1986-11-07 ES ES198686115437T patent/ES2026445T3/es not_active Expired - Lifetime
- 1986-11-11 DD DD86296171A patent/DD259849A5/de not_active IP Right Cessation
- 1986-11-12 SU SU864028507A patent/SU1445555A3/ru active
- 1986-11-12 AU AU65041/86A patent/AU589232B2/en not_active Ceased
- 1986-11-12 US US06/930,504 patent/US4766234A/en not_active Expired - Lifetime
- 1986-11-12 CA CA000522649A patent/CA1276164C/fr not_active Expired - Lifetime
- 1986-11-12 BR BR8605583A patent/BR8605583A/pt not_active IP Right Cessation
- 1986-11-12 JP JP61267877A patent/JPH0811748B2/ja not_active Expired - Lifetime
- 1986-11-13 KR KR1019860009579A patent/KR940008917B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0222334A2 (fr) | 1987-05-20 |
| BR8605583A (pt) | 1987-08-18 |
| SU1445555A3 (ru) | 1988-12-15 |
| ES2026445T3 (es) | 1992-05-01 |
| EP0222334B1 (fr) | 1991-09-04 |
| US4766234A (en) | 1988-08-23 |
| CA1276164C (fr) | 1990-11-13 |
| EP0222334A3 (en) | 1988-08-03 |
| DE3681250D1 (de) | 1991-10-10 |
| ATE66914T1 (de) | 1991-09-15 |
| AU589232B2 (en) | 1989-10-05 |
| DE3540147A1 (de) | 1987-05-14 |
| JPH0811748B2 (ja) | 1996-02-07 |
| AU6504186A (en) | 1987-05-21 |
| KR940008917B1 (ko) | 1994-09-28 |
| JPS62120352A (ja) | 1987-06-01 |
| KR870004945A (ko) | 1987-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NPV | Change in the person, the name or the address of the representative (addendum to changes before extension act) | ||
| ENJ | Ceased due to non-payment of renewal fee |