GB536017A - Polymeric quaternary ammonium salts from ditertiary diamines and dihalides - Google Patents
Polymeric quaternary ammonium salts from ditertiary diamines and dihalidesInfo
- Publication number
- GB536017A GB536017A GB24771/39A GB2477139A GB536017A GB 536017 A GB536017 A GB 536017A GB 24771/39 A GB24771/39 A GB 24771/39A GB 2477139 A GB2477139 A GB 2477139A GB 536017 A GB536017 A GB 536017A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibromide
- bis
- tetramethyl
- dihalide
- radicals
- 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.)
- Expired
Links
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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
536,017. Polymeric quaternary compounds. DU PONT DE NEMOURS & CO., E. I. Aug. 29, 1939, No. 24771. Convention date, Aug. 30, 1938. [Class 2 (iii)] Linear polymeric quaternary ammonium compounds are prepared by heating a dihalide, preferably a di-primary dihalide, with a ditertiary diamine. Dihalides, wherein the halogen atoms are attached to singly-bonded carbon atoms, include aliphatic or aromatic, cyclic or acyclic, straight or branched chain, saturated or unsaturated, unsubstituted or substituted diiodides, di-bromides or di-chlorides such as triglycol dichloride, dichlordipropyl ether, methylene dibromide, 1:3-dichloropropane, iso-butylene dibromide, trimethylethylene dibromide, 1:4- dibromopentane, p-xylylene dibromide, 1:4- cyclohexylenedichloride, methylenediiodide, 1-bromo-10-chlorodecane, octamethylenediiodide, 2:6-dibromo-n-heptane, tetramethylenedichloride, 2:3-dibromobutane, dodecamethylenedibromide, decamethylene dibromide and ethylene dichloride ; other radicals that may occur in the dihalide and which do not interfere in the reaction include ether, hydroxyl, keto, nitro, thiol, sulphide, carboxyl and ester groups. Diamines, wherein each nitrogen atom must be attached to at least two saturated radicals, include aliphatic, aromatic, cyclic, acyclic, homocyclic, heterocyclic, saturated, unsaturated substituted or unsubstituted diamines such as N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethyltriethyleneglycoldiamine N:N:N<SP>1</SP>:N<SP>1</SP>-tetraethyl- 1: 4-diaminocyclohexane, 1:10-bis-(diethylaminomethoxy)-decane, N:N<SP>1</SP>- bis-(2-hydroxyethyl)-piperazine, bis-(4-morpholine)-dodecane, bis-(1-piperidyl)-octane, 1:6-bis- (dimethylamino)-2:5-dimethylhexane, N:N:N<SP>1</SP>: N<SP>1</SP>-tetramethyl-p-phenylenediamine, N-N-N<SP>1</SP>N<SP>1</SP>- tetramethyl -1:6- diamino - 3 - hexene, N - allyl- N: N<SP>1</SP> : N<SP>1</SP>- trimethyloctadecamethylenediamine, N:N:N<SP>1</SP>:N<SP>1</SP>-diethylene - 1:2 - ethylenediamine, N:N: N<SP>1</SP>: N<SP>1</SP>- tetramethyldecamethylenediamine, N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylethylene diamine, N:N: N<SP>1</SP>:N<SP>1</SP>-tetramethyl-p-p<SP>1</SP>-diamino diphenylmethane, and N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylhexamethylenediamine ; other radicals that may occur in the diamine and do not interfere with the reaction include ether, sulphide, ketone, nitro, amide, hydroxyl and thiol groups. The amino and its halide must be so selected that their combined radical length exceeds seven. The products may be used as photographic chemicals, leather-treating chemicals, mold inhibitors, bactericides, pour-point depressors, pigment dispersion control agents, surface-active agents, modifying-agents for viscose or cellulose acetate, or as adhesives. In examples, solutions in methanol of decamethylene dibromide and (1) N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylhexamethylenediaamine, (2 )N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethyldecamethylenediamine, (3) N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylethylenediamine, or (4) N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethyl-p-p<SP>1</SP>- diaminodiphenylmethane are heated to yield polymers ; (5) ethylene dichloride is heated with N:N:N<SP>1</SP>:N<SP>1</SP>-tetramethylhexamethylenediamine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US536017XA | 1938-08-30 | 1938-08-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB536017A true GB536017A (en) | 1941-04-30 |
Family
ID=21985357
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24771/39A Expired GB536017A (en) | 1938-08-30 | 1939-08-29 | Polymeric quaternary ammonium salts from ditertiary diamines and dihalides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB536017A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2716134A (en) * | 1950-04-19 | 1955-08-23 | Eastman Kodak Co | N, n, n', n'-tetrasubstituted diamines |
US3055902A (en) * | 1959-08-04 | 1962-09-25 | Ciba Geigy Corp | Bis-(1-piperidino) alkanes |
US3931319A (en) * | 1974-10-29 | 1976-01-06 | Millmaster Onyx Corporation | Capped polymers |
US4012446A (en) * | 1974-10-29 | 1977-03-15 | Millmaster Onyx Corporation | Capped polymers |
US4027020A (en) * | 1974-10-29 | 1977-05-31 | Millmaster Onyx Corporation | Randomly terminated capped polymers |
US4091113A (en) * | 1975-09-04 | 1978-05-23 | Kewanee Industries, Inc. | Randomly terminated capped polymers |
US5512597A (en) * | 1991-11-08 | 1996-04-30 | Alcon Laboratories, Inc. | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
US5536494A (en) * | 1994-10-04 | 1996-07-16 | Alcon Laboratories, Inc. | Polyethylene oxide-containing quaternary ammunium polymers and pharmaceutical compositions containing an antimicrobial amount of same |
US5547663A (en) * | 1991-11-08 | 1996-08-20 | Alcon Laboratories, Inc. | Absolute molecular weight polymers and methods for their use |
US6051611A (en) * | 1991-11-08 | 2000-04-18 | Alcon Laboratories, Inc. | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobias |
US8106151B2 (en) * | 2007-04-17 | 2012-01-31 | Abbot Medical Optics Inc. | Polyquaternium-1 synthesis methods |
US8431751B1 (en) | 2008-12-24 | 2013-04-30 | Alcon Research, Ltd. | Polymeric quaternary ammonium compounds with vicinal hydroxy groups |
CN116410464A (en) * | 2023-04-14 | 2023-07-11 | 湖南大学 | Main chain cationic polymer capable of being click chemically modified and preparation method thereof |
-
1939
- 1939-08-29 GB GB24771/39A patent/GB536017A/en not_active Expired
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2716134A (en) * | 1950-04-19 | 1955-08-23 | Eastman Kodak Co | N, n, n', n'-tetrasubstituted diamines |
US3055902A (en) * | 1959-08-04 | 1962-09-25 | Ciba Geigy Corp | Bis-(1-piperidino) alkanes |
US3931319A (en) * | 1974-10-29 | 1976-01-06 | Millmaster Onyx Corporation | Capped polymers |
US4012446A (en) * | 1974-10-29 | 1977-03-15 | Millmaster Onyx Corporation | Capped polymers |
US4027020A (en) * | 1974-10-29 | 1977-05-31 | Millmaster Onyx Corporation | Randomly terminated capped polymers |
US4091113A (en) * | 1975-09-04 | 1978-05-23 | Kewanee Industries, Inc. | Randomly terminated capped polymers |
US5512597A (en) * | 1991-11-08 | 1996-04-30 | Alcon Laboratories, Inc. | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobials |
US5547663A (en) * | 1991-11-08 | 1996-08-20 | Alcon Laboratories, Inc. | Absolute molecular weight polymers and methods for their use |
WO1997045473A1 (en) * | 1991-11-08 | 1997-12-04 | Alcon Laboratories, Inc. | Absolute molecular weight polymers and methods for their use |
US6051611A (en) * | 1991-11-08 | 2000-04-18 | Alcon Laboratories, Inc. | Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobias |
US5536494A (en) * | 1994-10-04 | 1996-07-16 | Alcon Laboratories, Inc. | Polyethylene oxide-containing quaternary ammunium polymers and pharmaceutical compositions containing an antimicrobial amount of same |
US8106151B2 (en) * | 2007-04-17 | 2012-01-31 | Abbot Medical Optics Inc. | Polyquaternium-1 synthesis methods |
US8309679B2 (en) | 2007-04-17 | 2012-11-13 | Abbott Medical Optics Inc. | Polyquaternium-1 synthesis methods |
US8431751B1 (en) | 2008-12-24 | 2013-04-30 | Alcon Research, Ltd. | Polymeric quaternary ammonium compounds with vicinal hydroxy groups |
CN116410464A (en) * | 2023-04-14 | 2023-07-11 | 湖南大学 | Main chain cationic polymer capable of being click chemically modified and preparation method thereof |
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