GB834227A - Poly-n-quaternary ammonium electrolytes and í¡í¡ thereof - Google Patents

Poly-n-quaternary ammonium electrolytes and í¡í¡ thereof

Info

Publication number
GB834227A
GB834227A GB29394/59A GB2939459A GB834227A GB 834227 A GB834227 A GB 834227A GB 29394/59 A GB29394/59 A GB 29394/59A GB 2939459 A GB2939459 A GB 2939459A GB 834227 A GB834227 A GB 834227A
Authority
GB
United Kingdom
Prior art keywords
groups
dimethyl
ester
quaternary ammonium
acid
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
GB29394/59A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB834227A publication Critical patent/GB834227A/en
Expired legal-status Critical Current

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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J41/00Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/08Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/12Macromolecular compounds
    • B01J41/14Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds

Abstract

Water - soluble, poly - N - quaternary ammonium electrolytes are formed from proteins or polypeptides containing free amino or carboxyl groups in side chains by directly quaternizing amino groups to form products with at least 6 identical or different quaternary ammonium groups per molecule, or, in the case of starting materials containing free carboxyl groups, by reacting the carboxyl groups, if desired after esterification, either with a diamine containing a primary and a tertiary amine group, the latter then being quaternized, or with a diamine containing a primary amine and a quaternary ammonium group. Suitable agents for quaternization are alkyl halides, e.g. butyl bromide, lauryl bromide; ethylene iodohydrin; bromoacetamide; a -bromopropane sulphonic acid amide; ethane- or o-toluene-sulphonic acid methyl ester, methane- or benzene-sulphonic acid ethyl ester; dimethyl-, diethyl- or dipropyl sulphate; butane-1,3- or -1,4-sultone. Different alkylating agents can be used successively or simultaneously. By selecting suitable ones it is possible to introduce acid, ester or salt groups. The ester groups are subsequently saponified. Hydrophilic groups, e.g. acid amide, ureido, ureylene, hydroxyl, amino, carboxyl or sulphonic groups or ether or thioether bridges may also be introduced into the molecule. Groups with a negative charge, e.g. carboxyl or sulphonic acid, should be present in the final product in smaller number than the quaternary nitrogen atoms, and as salts, e.g. carboxylates. The products may be purified by dissolving, e.g. in methanol, glycol, butane-1,3-diol and precipitating, e.g. by addition of ether, acetone or isopropyl alcohol. They may be vacuum or freeze dried. Anions can be exchanged by means of anion exchangers. The examples relate to treatment of synthetic polypeptides (see Group IV (a)). The products are useful in pharmacy.ALSO:Water-soluble poly-N-quaternary ammonium electrolytes are formed from synthetic polypeptides, containing free amino or carboxyl groups in side chains, by directly quatenizing amino groups to form products with at least 6 identical or different quaternary ammonium groups per molecule or, in the case of polypeptides having free carboxyl groups, by reacting the carboxyl groups, if desired after esterification, either with a diamine containing a primary and a tertiary amine group the latter then being quaternized, or with a diamine containing a primary amine and a quaternary ammonium group. Suitable quaternizing agents are alkyl halides, e.g. butyl or lauryl bromide; ethylene iodohydrin; bromoacetamide; a -bromopropane sulphonic acid amide; ethane- or o-toluene-sulphonic acid methyl ester, methane-or benzene-sulphonic acid ethyl ester; dimethyl-diethyl or dipropyl sulphate; butane-1,3- or -1,4-sultone. Different alkylating agents can be used successively or simultaneously. By selecting suitable ones it is possible to introduce acid, ester or salt groups. The ester groups are subsequently saponified. Hydrophilic groups, e.g. acid amide, ureido, ureylene, hydroxyl, amino, carboxylic or sulphonic groups or ether or thioether bridges may also be introduced into the molecule. Groups with a negative charge, e.g. carboxyl or sulphonic acid, should be present in the final product in smaller number than the quaternary nitrogen atoms, and as salts, e.g. carboxylates. The products may be purified by solution, e.g. in methanol, glycol, butane-1,3-diol followed by precipitation, e.g. with ether, acetone or isopropyl alcohol. They may be vacuum or freeze dried. Anions can be exchanged by means of anion exchangers. In examples: (1) polylysine hydrochloride is reacted with dimethyl sulphate in presence of sodium carbonate; (2) polyglutamic acid-g -methyl ester is heated with N,N-dimethyl propylene diamine. The product is heated with a solution of propane sultone in dimethyl formamide and then with dimethyl sulphate. Unreacted ester groups are saponified; (3) a co-polypeptide is formed from l-glutamic acid-g -methyl ester N-carboxy anhydride and glycine - N - carboxy anhydride, and is heated with N,N-dimethyl propylene diamine and then with dimethyl sulphate; (4) a co-polypeptide is formed from "N" - carbobenzyloxy - l - lysine - N - carboxy anhydride and l-alanine-N-carboxy anhydride, the carbobenzyloxy group is split off and the product reacted with dimethyl sulphate; (5) a -polyglutamic acid dimethylaminopropylamide is heated with chloroacetic acid methyl ester and then with dimethyl sulphate; (6) a copolypeptide is prepared from l-glutamic acid-d -methyl ester-N-carboxy anhydride, glycine-N-carbomyanhydride and l-leucine-N-carboxyanhydride and is heated with N,N-dimethyl propylene diamine and then with dimethyl sulphate. The products are useful in pharmacy.
GB29394/59A 1955-01-22 1956-01-20 Poly-n-quaternary ammonium electrolytes and í¡í¡ thereof Expired GB834227A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE834227X 1955-01-22

Publications (1)

Publication Number Publication Date
GB834227A true GB834227A (en) 1960-05-04

Family

ID=6760618

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29394/59A Expired GB834227A (en) 1955-01-22 1956-01-20 Poly-n-quaternary ammonium electrolytes and í¡í¡ thereof

Country Status (1)

Country Link
GB (1) GB834227A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3907755A (en) * 1972-05-03 1975-09-23 Rhone Poulenc Sa Sulfonated polymers derived from L-lysine
GB2174097A (en) * 1985-03-22 1986-10-29 Ceskoslovenska Akademie Ved Polymeric stabilizer of water-in-oil emulsions
EP1830639A1 (en) * 2004-12-30 2007-09-12 Appeartex AB Antimicrobial and antiviral product

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3907755A (en) * 1972-05-03 1975-09-23 Rhone Poulenc Sa Sulfonated polymers derived from L-lysine
GB2174097A (en) * 1985-03-22 1986-10-29 Ceskoslovenska Akademie Ved Polymeric stabilizer of water-in-oil emulsions
EP1830639A1 (en) * 2004-12-30 2007-09-12 Appeartex AB Antimicrobial and antiviral product
EP1830639A4 (en) * 2004-12-30 2012-03-14 Appeartex Ab Antimicrobial and antiviral product

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