DE1111825B - Verfahren zur Herstellung von hochpolymeren quaternaeren Ammoniumverbindungen - Google Patents
Verfahren zur Herstellung von hochpolymeren quaternaeren AmmoniumverbindungenInfo
- Publication number
- DE1111825B DE1111825B DEB52479A DEB0052479A DE1111825B DE 1111825 B DE1111825 B DE 1111825B DE B52479 A DEB52479 A DE B52479A DE B0052479 A DEB0052479 A DE B0052479A DE 1111825 B DE1111825 B DE 1111825B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- solution
- acid amide
- water
- temperature
- 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
- 229920000642 polymer Polymers 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 7
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229920001131 Pulp (paper) Polymers 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 5
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- MEWMVDVKCVAIJI-UHFFFAOYSA-N CCN(CC)CC=C(C)C(N)=O Chemical compound CCN(CC)CC=C(C)C(N)=O MEWMVDVKCVAIJI-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- -1 alkyl halogen compounds Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SKWFFIUBNIHMJV-UHFFFAOYSA-N 1-ethenoxy-n,n-diethylethanamine Chemical compound CCN(CC)C(C)OC=C SKWFFIUBNIHMJV-UHFFFAOYSA-N 0.000 description 1
- KHQXOTRXULHTQF-UHFFFAOYSA-N 2-(diethylaminomethyl)prop-2-enamide Chemical compound CCN(CC)CC(=C)C(N)=O KHQXOTRXULHTQF-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- BCBHWVAFKCCWBG-UHFFFAOYSA-N chloroethene;ethenyl propanoate Chemical compound ClC=C.CCC(=O)OC=C BCBHWVAFKCCWBG-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical group NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- IQBHTRVNLWHNBL-UHFFFAOYSA-N n-(diethylaminomethyl)-2-methylprop-2-enamide Chemical compound CCN(CC)CNC(=O)C(C)=C IQBHTRVNLWHNBL-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
- D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
- D21H17/45—Nitrogen-containing groups
- D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE588422D BE588422A (enrdf_load_stackoverflow) | 1959-03-14 | ||
| DEB52479A DE1111825B (de) | 1959-03-14 | 1959-03-14 | Verfahren zur Herstellung von hochpolymeren quaternaeren Ammoniumverbindungen |
| DEB52505A DE1118968B (de) | 1959-03-14 | 1959-03-17 | Verfahren zur Herstellung von hochpolymeren quaternaeren Ammoniumverbindungen |
| GB861960A GB887900A (en) | 1959-03-14 | 1960-03-11 | Improvements in the production of highly polymeric quaternary ammonium compounds |
| FR821235A FR1252325A (fr) | 1959-03-14 | 1960-03-14 | Procédé pour la production de composés d'ammonium quaternaires, macromoléculaires |
| FR841475A FR78541E (fr) | 1959-03-14 | 1960-10-18 | Procédé pour la production de composés d'ammonium quaternaires macromoléculaires |
| GB1589163A GB982269A (en) | 1959-03-14 | 1963-04-23 | Production of highly polymerised quarternary ammonium compounds |
| FR932671A FR83494E (fr) | 1959-03-14 | 1963-04-25 | Procédé pour la production de composés d'ammonium quaternaires, macromoléculaires |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB52479A DE1111825B (de) | 1959-03-14 | 1959-03-14 | Verfahren zur Herstellung von hochpolymeren quaternaeren Ammoniumverbindungen |
| DEB66972A DE1213996B (de) | 1962-04-25 | 1962-04-25 | Verfahren zur Herstellung von hochpolymeren quaternaeren Ammoniumverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1111825B true DE1111825B (de) | 1961-07-27 |
Family
ID=25965352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB52479A Pending DE1111825B (de) | 1959-03-14 | 1959-03-14 | Verfahren zur Herstellung von hochpolymeren quaternaeren Ammoniumverbindungen |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE588422A (enrdf_load_stackoverflow) |
| DE (1) | DE1111825B (enrdf_load_stackoverflow) |
| GB (2) | GB887900A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002254A1 (en) * | 1977-12-02 | 1979-06-13 | The Dow Chemical Company | Preparation of N-(aminomethyl)-alpha,beta-ethylenically unsaturated carboxamides, their polymers and the quaternized carboxamides thereof |
| FR2441610A1 (fr) * | 1978-11-16 | 1980-06-13 | Texaco Development Corp | Composes quaternaires d'acrylamide ou de methacrylamide et leur utilisation comme catalyseurs pour la preparation de polymeres contenant des liaison isocyanurate et urethane |
| FR2455033A1 (fr) * | 1979-04-23 | 1980-11-21 | Texaco Development Corp | Composes quaternaires alkoxypropyles d'acrylamide ou de methacrylamide |
| EP0604844A1 (de) * | 1992-12-22 | 1994-07-06 | Röhm Gmbh | Verfahren zur Herstellung von Trialklammoniumalkyl(meth)acryl-Verbindungen |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179098B (de) * | 1961-05-03 | 1964-10-01 | Basf Ag | Flotationsmittel zum Klaeren von Papierfasern enthaltenden Abwaessern |
| US4057533A (en) * | 1972-07-03 | 1977-11-08 | Gaf Corporation | Process for preparation of quaternized cationic vinyllactam-acrylamide copolymers |
| CA1101158A (en) * | 1976-10-26 | 1981-05-19 | John A. Sedlak | Strengthening agents |
| US4229267A (en) * | 1979-06-01 | 1980-10-21 | Richardson Chemical Company | Alkaline bright zinc plating and additive therefor |
| JP2661241B2 (ja) * | 1988-03-03 | 1997-10-08 | 住友化学工業株式会社 | エチレン共重合体を有効成分とする殺菌剤および殺菌性樹脂組成物 |
| DE4430069A1 (de) * | 1994-08-25 | 1996-02-29 | Stockhausen Chem Fab Gmbh | Wäßrige, lösungsmittelfreie Dispersionen von kationischen Polymerisaten enthaltende Papierleimungsmittel und Verfahren zur Herstellung von geleimtem Papier unter Verwendung dieser Mittel |
-
0
- BE BE588422D patent/BE588422A/xx unknown
-
1959
- 1959-03-14 DE DEB52479A patent/DE1111825B/de active Pending
-
1960
- 1960-03-11 GB GB861960A patent/GB887900A/en not_active Expired
-
1963
- 1963-04-23 GB GB1589163A patent/GB982269A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002254A1 (en) * | 1977-12-02 | 1979-06-13 | The Dow Chemical Company | Preparation of N-(aminomethyl)-alpha,beta-ethylenically unsaturated carboxamides, their polymers and the quaternized carboxamides thereof |
| FR2441610A1 (fr) * | 1978-11-16 | 1980-06-13 | Texaco Development Corp | Composes quaternaires d'acrylamide ou de methacrylamide et leur utilisation comme catalyseurs pour la preparation de polymeres contenant des liaison isocyanurate et urethane |
| FR2455033A1 (fr) * | 1979-04-23 | 1980-11-21 | Texaco Development Corp | Composes quaternaires alkoxypropyles d'acrylamide ou de methacrylamide |
| EP0604844A1 (de) * | 1992-12-22 | 1994-07-06 | Röhm Gmbh | Verfahren zur Herstellung von Trialklammoniumalkyl(meth)acryl-Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB887900A (en) | 1962-01-24 |
| BE588422A (enrdf_load_stackoverflow) | |
| GB982269A (en) | 1965-02-03 |
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