DD257828C4 - Verfahren zur herstellung von urethanen aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen - Google Patents

Verfahren zur herstellung von urethanen aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen

Info

Publication number: DD257828C4
Authority: DD; German Democratic Republic
Prior art keywords: adduct; isocyanate; formula; compound; formulas
Prior art date: 1986-07-03

Application number

DD87304536A

Other languages

German (de)

English (en)

Other versions

DD257828A5 (de

Inventor

Frank Wehowsky

Rolf Kleber

Lothar Jaeckel

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1986-07-03

Filing date

1987-07-02

Publication date

1989-03-01

1987-07-02 Application filed by ��@��k�� filed Critical ��@��k��

1988-06-29 Publication of DD257828A5 publication Critical patent/DD257828A5/de

1989-03-01 Publication of DD257828C4 publication Critical patent/DD257828C4/de

Links

239000012948 isocyanate Substances 0.000 title claims abstract description 39
150000002513 isocyanates Chemical class 0.000 title claims abstract description 29
150000003673 urethanes Chemical class 0.000 title claims abstract description 23
-1 FLUORO ALCOHOLS Chemical class 0.000 title claims abstract description 19
150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title description 3
125000001931 aliphatic group Chemical group 0.000 claims abstract description 29
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims abstract description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims 1
239000004753 textile Substances 0.000 abstract description 19
239000010985 leather Substances 0.000 abstract description 6
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract description 5
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 3
230000002209 hydrophobic effect Effects 0.000 abstract description 2
230000001588 bifunctional effect Effects 0.000 abstract 2
125000005442 diisocyanate group Chemical group 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 57
239000000203 mixture Substances 0.000 description 24
239000000047 product Substances 0.000 description 19
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
239000004744 fabric Substances 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
239000000463 material Substances 0.000 description 8
238000010438 heat treatment Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000011521 glass Substances 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 4
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 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
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
239000000839 emulsion Substances 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
229940018563 3-aminophenol Drugs 0.000 description 2
229940090248 4-hydroxybenzoic acid Drugs 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
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
JERCPDZTVRGVSH-UHFFFAOYSA-N benzene-1,2-diol;benzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1.OC1=CC=CC=C1O JERCPDZTVRGVSH-UHFFFAOYSA-N 0.000 description 2
ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 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
239000003795 chemical substances by application Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000470 constituent Substances 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
239000012975 dibutyltin dilaurate Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000835 fiber Substances 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
150000003254 radicals Chemical class 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 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
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 2
125000005628 tolylene group Chemical group 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
241001494479 Pecora Species 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000010411 cooking Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007598 dipping method Methods 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
238000004043 dyeing Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 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
150000008282 halocarbons Chemical class 0.000 description 1
YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 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
239000003607 modifier Substances 0.000 description 1
229940094933 n-dodecane Drugs 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
229920001522 polyglycol ester Polymers 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000005871 repellent Substances 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
238000009987 spinning Methods 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
238000009988 textile finishing Methods 0.000 description 1
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 1
125000003944 tolyl 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
239000003039 volatile agent Substances 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
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- 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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
- 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)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD87304536A 1986-07-03 1987-07-02 Verfahren zur herstellung von urethanen aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen DD257828C4 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863622284 DE3622284A1 (de)	1986-07-03	1986-07-03	Urethane aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen, verfahren zu ihrer herstellung und ihre verwendung

Publications (2)

Publication Number	Publication Date
DD257828A5 DD257828A5 (de)	1988-06-29
DD257828C4 true DD257828C4 (de)	1989-03-01

Family

ID=6304271

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87304536A DD257828C4 (de)	1986-07-03	1987-07-02	Verfahren zur herstellung von urethanen aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen

Country Status (12)

Country	Link
US (1)	US4782175A (fr)
EP (1)	EP0253186B1 (fr)
JP (1)	JPS6314764A (fr)
KR (1)	KR880001581A (fr)
AT (1)	ATE64593T1 (fr)
AU (1)	AU593919B2 (fr)
BR (1)	BR8703371A (fr)
CA (1)	CA1296018C (fr)
DD (1)	DD257828C4 (fr)
DE (2)	DE3622284A1 (fr)
ES (1)	ES2023382B3 (fr)
SU (1)	SU1590038A3 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3722375A1 (de) *	1987-07-07	1989-01-19	Hoechst Ag	Fluor und polysiloxan enthaltende urethane, verfahren zu ihrer herstellung und ihre verwendung
DE3744423A1 (de) *	1987-12-29	1989-07-13	Hoechst Ag	Urethane aus aliphatischen fluoralkoholen, isocyanaten und substituierten aromatischen verbindungen, verfahren zu ihrer herstellung und ihre verwendung
US4935535A (en) *	1989-01-19	1990-06-19	National Science Council	Ultraviolet-autocurable benzophenone tetracarboxylic dianhydride-based polyurethane acrylate oligomers
JP2503657B2 (ja) *	1989-06-05	1996-06-05	大日本インキ化学工業株式会社	撥水撥油剤
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
US5580645A (en) *	1989-12-29	1996-12-03	E. I. Du Pont De Nemours And Company	Substrates treated with polyfluoro nitrogen-containing organic compounds
US5276175A (en) *	1991-04-02	1994-01-04	Minnesota Mining And Manufacturing Company	Isocyanate derivatives comprising flourochemical oligomers
DE69207779T2 (de)	1991-11-12	1996-05-30	Minnesota Mining & Mfg	Derivate fluoroaliphatischer dimer-säuren und deren verwendung
JP2523095Y2 (ja) *	1991-11-15	1997-01-22	株式会社テック	ロードセル秤
US5486210A (en)	1992-01-30	1996-01-23	Reeves Brothers, Inc.	Air bag fabric containing graft polymer thereon
US5407728A (en)	1992-01-30	1995-04-18	Reeves Brothers, Inc.	Fabric containing graft polymer thereon
DE69310156T2 (de) *	1992-02-28	1997-09-18	Du Pont	Schmutzabweisende fluorcarbamate
DE4244951C2 (de) *	1992-12-01	1998-08-06	Minnesota Mining & Mfg	Fasersubstrat mit Wasser-, Öl-, Schmutzabweisungsvermögen und Weichgriffigkeit
US5496642A (en) *	1994-05-09	1996-03-05	Olin Corporation	Low VOC, fluorocompound-containing one-component and two-component coating compositions for slippery coatings
EP0841405B1 (fr)	1996-11-07	1999-12-29	Minnesota Mining And Manufacturing Company	Utilisation de copolymères amphiphiles contenant des monomères fluorés pour imperméabiliser des cuirs
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US6525127B1 (en)	1999-05-11	2003-02-25	3M Innovative Properties Company	Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates
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1986
- 1986-07-03 DE DE19863622284 patent/DE3622284A1/de not_active Withdrawn
1987
- 1987-06-27 EP EP87109287A patent/EP0253186B1/fr not_active Expired - Lifetime
- 1987-06-27 ES ES87109287T patent/ES2023382B3/es not_active Expired - Lifetime
- 1987-06-27 AT AT87109287T patent/ATE64593T1/de not_active IP Right Cessation
- 1987-06-27 DE DE8787109287T patent/DE3770885D1/de not_active Expired - Fee Related
- 1987-07-01 US US07/068,924 patent/US4782175A/en not_active Expired - Fee Related
- 1987-07-02 AU AU75052/87A patent/AU593919B2/en not_active Ceased
- 1987-07-02 DD DD87304536A patent/DD257828C4/de not_active IP Right Cessation
- 1987-07-02 BR BR8703371A patent/BR8703371A/pt unknown
- 1987-07-02 KR KR1019870007013A patent/KR880001581A/ko not_active Ceased
- 1987-07-02 CA CA000541102A patent/CA1296018C/fr not_active Expired - Fee Related
- 1987-07-02 JP JP62164136A patent/JPS6314764A/ja active Pending
- 1987-07-02 SU SU874202846A patent/SU1590038A3/ru active

Also Published As

Publication number	Publication date
AU7505287A (en)	1988-01-07
JPS6314764A (ja)	1988-01-21
DD257828A5 (de)	1988-06-29
ATE64593T1 (de)	1991-07-15
DE3622284A1 (de)	1988-01-07
EP0253186A2 (fr)	1988-01-20
BR8703371A (pt)	1988-03-15
CA1296018C (fr)	1992-02-18
EP0253186A3 (en)	1988-09-21
SU1590038A3 (ru)	1990-08-30
EP0253186B1 (fr)	1991-06-19
KR880001581A (ko)	1988-04-25
AU593919B2 (en)	1990-02-22
ES2023382B3 (es)	1992-01-16
DE3770885D1 (de)	1991-07-25
US4782175A (en)	1988-11-01

Legal Events

Date	Code	Title	Description
2000-05-11	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD257828C4 (de)	1989-03-01	Verfahren zur herstellung von urethanen aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen
EP0298364B1 (fr)	1993-10-06	Uréthanes contenant du fluor et une chaîne de polysiloxane, procédé de préparation et leur application
EP0325918B1 (fr)	1993-03-31	Polyuréthanes modifiés contenant des groupes perfluoroaliphatiques et leur utilisation
EP0872503B1 (fr)	2002-09-04	Produits de réaction d'isocyanates avec des composés hydroxyles pour l'apprêt textile
EP1088929B1 (fr)	2005-08-31	Compositions pour le finissage oléo-et hydrofuge de matériaux fibreuses
DE3002369A1 (de)	1980-08-07	Verfahren zur schmutz- und fleckenabweisenden ausruestung von textilen bodenbelaegen oder des textilen ausgangsmaterials und fluessiges mittel zur durchfuehrung des verfahrens
EP0322759B1 (fr)	1993-09-01	Méthanes préparés de fluoro alcools, isocyanates et composés aromatiques substituées, procédé de leur préparation et leur utilisation
DE69030564T2 (de)	1997-09-25	Stickstoff enthaltende organische Polyfluorverbindungen
DE3943127A1 (de)	1991-07-04	Urethane als aliphatischen fluoralkoholen, isocyanaten und carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung
EP0213580B1 (fr)	1990-07-18	Uréthanes contenant des groupements perfluoralcoyle et épichlorhydrine, leur dispersion aqueuse et leur application
EP0036076A2 (fr)	1981-09-23	Procédé de préparation d'apprêts exempts de formaldéhyde pour matières textiles cellulosiques et leurs applications
EP0560161A1 (fr)	1993-09-15	Composition et procédé de traitement de textiles
EP0222334B1 (fr)	1991-09-04	Uréthanes contenant des groupements perfluoroalcoyle, groupes obtenus à partir d'épichlorhydrine et des restes diols, procédé de préparation et utilisation
EP1013687B1 (fr)	2005-04-13	Dispersions aqueuses pour l'ennoblissement textile
DE69310156T2 (de)	1997-09-18	Schmutzabweisende fluorcarbamate
DE3802633A1 (de)	1989-08-03	Modifizierte, perfluoraliphatische gruppen enthaltende polyurethane und deren verwendung
DD249267A5 (de)	1987-09-02	Perfluoralkyl- und epichlorhydrin-gruppen enthaltende urethane, diese urethane enthaltende waessrige dispersionen und ihre verwendung
DE2120090A1 (de)	1972-11-09	Neue Hilfsstoffe zur Ausrüstung von Keratinfasern enthaltenden Textilien
EP0359039A2 (fr)	1990-03-21	Procédé d'apprêt infraissable de matériaux textiles
DE3607773A1 (de)	1987-09-10	Fluoralkylliganden enthaltende polyurethane, verfahren zu ihrer herstellung und ihre zubereitungen und ihre verwendung
DE2403454A1 (de)	1974-08-08	N-heterocyclische perfluoralkylcarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE3605844A1 (de)	1987-08-27	Perfluoralkyl- und epichlorhydrin-gruppen enthaltende urethane, diese urethane enthaltende waessrige dispersionen und ihre verwendung
AT338224B (de)	1977-08-10	Verfahren zur herstellung von neuen aminodicarbonsaurediesterverbindungen
DE4022443A1 (de)	1992-01-16	Perfluoraliphatische gruppen enthaltende copolymere mit urethan- und siloxaneinheiten
DE2525508A1 (de)	1976-12-16	Diaminoalkylphosphonsaeuredialkylester und verfahren zu ihrer herstellung