DE2601438A1 - Quaternisiertes halogenhaltiges alkylenoxidcopolymerisat - Google Patents
Quaternisiertes halogenhaltiges alkylenoxidcopolymerisatInfo
- Publication number
- DE2601438A1 DE2601438A1 DE19762601438 DE2601438A DE2601438A1 DE 2601438 A1 DE2601438 A1 DE 2601438A1 DE 19762601438 DE19762601438 DE 19762601438 DE 2601438 A DE2601438 A DE 2601438A DE 2601438 A1 DE2601438 A1 DE 2601438A1
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- quaternized
- water
- mol
- alkylene oxide
- 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.)
- Withdrawn
Links
- 229920001577 copolymer Polymers 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 229920000647 polyepoxide Polymers 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 229920003169 water-soluble polymer Polymers 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 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 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- -1 Alkyl glycidyl ethers Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 2
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000011272 standard treatment Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YTURKLITUCHJSO-UHFFFAOYSA-N 2-(3-phenoxypropoxymethyl)oxirane Chemical class C=1C=CC=CC=1OCCCOCC1CO1 YTURKLITUCHJSO-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- SMBYUOXUISCLCF-UHFFFAOYSA-N n-ethyl-n-methylpropan-1-amine Chemical compound CCCN(C)CC SMBYUOXUISCLCF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
- C08L71/03—Polyepihalohydrins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54357775A | 1975-01-23 | 1975-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2601438A1 true DE2601438A1 (de) | 1976-07-29 |
Family
ID=24168614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762601438 Withdrawn DE2601438A1 (de) | 1975-01-23 | 1976-01-16 | Quaternisiertes halogenhaltiges alkylenoxidcopolymerisat |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4062832A (enExample) |
| JP (1) | JPS5198799A (enExample) |
| BE (1) | BE837867A (enExample) |
| CA (1) | CA1078996A (enExample) |
| DE (1) | DE2601438A1 (enExample) |
| FR (1) | FR2298569A1 (enExample) |
| GB (1) | GB1502061A (enExample) |
| IT (1) | IT1053414B (enExample) |
| NL (1) | NL7600598A (enExample) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2483749A (en) * | 1948-02-24 | 1949-10-04 | Gen Mills Inc | Quaternary ammonium salts |
| US3320317A (en) * | 1963-07-09 | 1967-05-16 | Dow Chemical Co | Quaternary ammonium adducts of polyepichlorohydrin |
| US3428680A (en) * | 1964-01-03 | 1969-02-18 | Procter & Gamble | Polyquaternary ammonium salts of polymerized epichlorohydrin |
| GB1208474A (en) * | 1968-04-29 | 1970-10-14 | Agfa Gevaert Nv | Electroconductive layers for use in electrographic and electrophotographic recording elements |
| BE754115A (fr) * | 1968-07-08 | 1971-01-29 | Dow Chemical Co | Copolymeres d'oxyde d'alkylene pouvant etre utilises dans la fabrication d'articles elastomeres |
| US3640766A (en) * | 1970-01-07 | 1972-02-08 | Nalco Chemical Co | Electrophotographic-recording member and process of producing the same |
| US3674725A (en) * | 1970-12-18 | 1972-07-04 | Nalco Chemical Co | Cationization of starch for filler retention utilizing a cationic polyepihalohydrin-tertiary amine polymer |
| US3864288A (en) * | 1973-10-15 | 1975-02-04 | Goodrich Co B F | Quaternized polyepihalohydrin thickening agent |
-
1976
- 1976-01-16 DE DE19762601438 patent/DE2601438A1/de not_active Withdrawn
- 1976-01-21 NL NL7600598A patent/NL7600598A/xx not_active Application Discontinuation
- 1976-01-22 JP JP51005510A patent/JPS5198799A/ja active Pending
- 1976-01-22 CA CA244,081A patent/CA1078996A/en not_active Expired
- 1976-01-22 IT IT47745/76A patent/IT1053414B/it active
- 1976-01-22 FR FR7601675A patent/FR2298569A1/fr not_active Withdrawn
- 1976-01-23 GB GB2738/76A patent/GB1502061A/en not_active Expired
- 1976-01-23 BE BE163767A patent/BE837867A/xx unknown
- 1976-03-03 US US05/663,381 patent/US4062832A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5198799A (enExample) | 1976-08-31 |
| US4062832A (en) | 1977-12-13 |
| CA1078996A (en) | 1980-06-03 |
| GB1502061A (en) | 1978-02-22 |
| BE837867A (fr) | 1976-07-23 |
| NL7600598A (nl) | 1976-07-27 |
| FR2298569A1 (fr) | 1976-08-20 |
| IT1053414B (it) | 1981-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0025515B1 (de) | Verwendung von stickstoffhaltigen Kondensationsprodukten als Retentionsmittel, Flockungsmittel und Entwässerungsbeschleuniger bei der Papierherstellung | |
| DE1595179C3 (de) | Verfahren zur Herstellung eines linearen hochmolekularen Polymeren | |
| EP0895521B1 (de) | Modifizierte, feinteilige, wasserunlösliche polymerisate von aziridinen | |
| EP0428003B1 (de) | Verfahren zur Herstellung von Polyetherglykolen | |
| EP0229622A2 (de) | Verfahren zur Herstellung von 2-Oxo-1,3-dioxolanen | |
| DE2230728A1 (de) | Verfahren zur stereoregulären Polymerisation von alpha-Olefinen | |
| DE1645660A1 (de) | Epoxyharz-Mischungen | |
| DE2127082B2 (de) | Verfahren zur Herstellung von wasserlöslichen, hochmolekularen Polyätheraminen und deren Salze und deren Verwendung | |
| DE2244513A1 (de) | Amin-modifizierte polyalkylenoxide | |
| DE1256896B (de) | Verfahren zur Herstellung von Copolymerisaten des Formaldehyds | |
| DE2035794A1 (de) | Alkylenoxydinterpolymere | |
| EP0314619B1 (de) | Epoxidharzgemische | |
| DE1907243A1 (de) | Hexafluorantimonat-Amin-Katalysatoren | |
| EP0000714B1 (de) | Hilfsmittel zur Verbesserung der Retention, Entwässerung und Aufbereitung, insbesondere bei der Papierherstellung | |
| EP0158247B1 (de) | Papierhilfsmittel | |
| DE1720912A1 (de) | Verfahren zur Herstellung von hochmolekularen,hydroxylgruppenhaltigen Polyaethern | |
| DE2601438A1 (de) | Quaternisiertes halogenhaltiges alkylenoxidcopolymerisat | |
| DE2127840A1 (de) | Hitzehartbare Formpulver unter Ver wendung von Glycidylmethacrylat und aro matischen Aminen | |
| DE2406367C2 (de) | Ionenbindungen aufweisende, vernetzte makromolekulare Polyäther und Verfahren zu deren Herstellung | |
| EP0362138B1 (de) | Epoxidharzgemische | |
| EP3713989B1 (de) | Hochmolekulare polyoxyalkylene mit tiefer glastemperatur hergestellt nach der grafting-through-methode | |
| EP0362140B1 (de) | Epoxidharzgemische | |
| DE3427063A1 (de) | Verfahren zur herstellung von kationischen monomeren, solche monomere und verfahren zur herstellung von polymeren | |
| DE1795364C3 (de) | Verfahren zur Herstellung von Blockmischpolymeren | |
| DE1518119C2 (de) | Verfahren zur Herstellung von 2 2 Bis (phenylol) propan di glycidyl ather |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |