GB790563A - Manufacture of polymeric quaternary ammonium compounds - Google Patents
Manufacture of polymeric quaternary ammonium compoundsInfo
- Publication number
- GB790563A GB790563A GB1771855A GB1771855A GB790563A GB 790563 A GB790563 A GB 790563A GB 1771855 A GB1771855 A GB 1771855A GB 1771855 A GB1771855 A GB 1771855A GB 790563 A GB790563 A GB 790563A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ammonium
- gamma
- beta
- methosulphate
- methacrylamide
- 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
- 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
Abstract
Quaternary ammonium compounds of the formula: (1) CH2 = C(R)-CONH-R1-N(tert)X wherein R stands for hydrogen or -CH3, R1 stands for an alkylene radical in which the carbon chain may be interrupted by heteroatoms for example oxygen, N(tert) stands for the group of atoms forming an aliphatic (including cycloaliphatic and araliphatic) or heterocyclic tertiary amine and X stands for the monovalent anion of a salt-forming acid, are made by reacting a compound of the formula: (2) CH2 = C(R)-CO.NH-R1-N = R1R2 wherein -N = R1R2 is a dialkylamino group or a heterocyclic ring and R and R1 have the significance stated above, with alkyl or aralkyl halides, alkyl sulphates or halogen substituted fatty carboxylic acids, if necessary in the presence of a polymerization inhibitor such as 2 : 4 - dimethyl - 6 - tert. - butylphenol. Compounds of formula (2) specified are N-(beta-diethylaminoethyl)-acrylamide and methacrylamide, N - (gamma - dimethylaminopropyl) acrylamide and methacrylamide, N-(beta-dimethylaminoethyl) acrylamide and methacrylamide, N - (gamma - diethylaminopropyl) methacrylamide, N - (beta - piperidinoethyl) methacrylamide, N - (beta - morpholinoethyl) methacrylamide, N - (gamma - piperidinopropyl) methacrylamide and N - (gammahexamethyleneiminopropyl) methacrylamide.ALSO:Polymeric quaternary ammonium compounds are made by polymerizing, in the absence of monomers free of quaternary ammonium groups, a compound of the formula: CH2 = C(R)-CO.NH-R1-N(tert)X wherein R is hydrogen or -CH3, R1 is an alkylene radical in which the carbon chain may be interrupted by heteroatoms for example oxygen, N(tert) is a group of atoms forming an aliphatic (including cycloaliphatic and araliphatic) or heterocyclic tertiary amine and X is the monovalent anion of a salt-forming acid. Polymerization may be carried out in aqueous solution in the presence of a catalyst such as benzoyl peroxide, potassium or ammonium persulphate or a mixture of ammonium persulphate and sodium hydrosulphite; in one procedure a mixture of monomer, catalyst and water is added gradually to a heated aqueous medium. The anion of the polymeric quaternary ammonium monomer may be replaced by a different anion by treatment with a suitable salt, e.g. silver acetate, sodium stearate or sodium dodecosulphate. In examples the following monomers are polymerized: (1) trimethyl-(b -methacrylaminoethyl) ammonium methosulphate, (2) methyl - (beta - methacrylaminoethyl) piperidinium methosulphate, (3) diethylmethyl - (beta - methacrylylaminoethyl) ammonium methosulphate, (4) trimethyl - (gammamethacrylaminopropyl) ammonium methosulphate, (5) methyldiethyl - (gamma - methacrylylaminopropyl) ammonium methosulphate, (6) trimethyl - (beta - acrylylaminoethyl) ammonium methosulphate, (7) methyldiethyl - (beta - acrylylaminoethyl) ammonium methosulphate, (8) trimethyl - (gammaacrylaminopropyl) ammonium methosulphate, (9) allyldiethyl - (beta - methacrylylaminoethyl) ammonium bromide, (10) methyldiethyl-(gamma - methacrylylaminopropyl) ammonium p - toluenesulphonate, (11) cetyldiethyl (gamma - methacrylaminopropyl) ammonium bromide, (13) butyldiethyl - (gamma - methacrylaminopropyl) ammonium bromide, (14) benzyldiethyl - (gammamethacrylaminopropyl) ammonium chloride, (15) methyldibutyl - (methacrylaminopropyl) ammonium methosulphate, (16) tributyl - (gamma - methacrylylaminopropyl) ammonium bromide, (17) benzyldibutyl - (gamma - methacrylaminopropyl) ammonium chloride, and (18) methyldibutyl-(gamma - acrylylaminopropyl) ammonium methosulphate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1771855A GB790563A (en) | 1955-06-20 | 1955-06-20 | Manufacture of polymeric quaternary ammonium compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1771855A GB790563A (en) | 1955-06-20 | 1955-06-20 | Manufacture of polymeric quaternary ammonium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB790563A true GB790563A (en) | 1958-02-12 |
Family
ID=10100013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1771855A Expired GB790563A (en) | 1955-06-20 | 1955-06-20 | Manufacture of polymeric quaternary ammonium compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB790563A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3302069A1 (en) * | 1982-02-01 | 1983-08-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Polymer- and surfactant-containing preparations, and the preparation and use thereof |
-
1955
- 1955-06-20 GB GB1771855A patent/GB790563A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3302069A1 (en) * | 1982-02-01 | 1983-08-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Polymer- and surfactant-containing preparations, and the preparation and use thereof |
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