GB536017A - Polymeric quaternary ammonium salts from ditertiary diamines and dihalides - Google Patents

Polymeric quaternary ammonium salts from ditertiary diamines and dihalides

Info

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
Application number
GB24771/39A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB536017A publication Critical patent/GB536017A/en
Expired legal-status Critical Current

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

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.
GB24771/39A 1938-08-30 1939-08-29 Polymeric quaternary ammonium salts from ditertiary diamines and dihalides Expired GB536017A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (15)

* Cited by examiner, † Cited by third party
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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