GB677350A - Improved method of preparing halomethylated polymers of alkenyl aromatic compounds - Google Patents
Improved method of preparing halomethylated polymers of alkenyl aromatic compoundsInfo
- Publication number
- GB677350A GB677350A GB28876/49A GB2887649A GB677350A GB 677350 A GB677350 A GB 677350A GB 28876/49 A GB28876/49 A GB 28876/49A GB 2887649 A GB2887649 A GB 2887649A GB 677350 A GB677350 A GB 677350A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- bromide
- alpha
- ether
- vinyl
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/24—Haloalkylation
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polymers and copolymers of alkenyl aromatic compounds containing in chemically combined form at least 50 per cent of at least one monoalkenyl aromatic compound that contains a vinyl or isopropenyl radical are catalytically halomethylated by treatment at a temperature of - 10 DEG to 125 DEG C. with a halomethylating agent such as methylene chloride, bromide or bromo-chloride, chlormethyl methyl ether, bromomethyl methyl ether, alpha, alpha1-dichlorodimethyl ether, alpha, alpha1-dibromodimethyl ether, mixtures of hydrogen chloride and formaldehyde or paraformaldehyde, and mixtures of hydrogen iodide, paraformaldehyde, and an acid, the reaction being carried out in the presence of a solvent or swelling agent for the polymer such as the halomethylating agent, trioxane, carbon bisulphide and tetrachloroethylene; the halomethylating agent is employed in amount at least as great as that required to introduce into the polymer molecule at least one halomethyl group per ten aromatic nuclei. Polymers specified are those derived from one or more of styrene, alpha methyl styrene, nuclear chlorostyrenes, vinyl toluenes, vinyl xylene, vinyl naphthalenes and nuclear ethyl vinyl benzenes, and copolymers of these with butadiene, isoprene, 2,3-dimethyl butadiene, divinyl benzene and diallyl maleate. Suitable catalysts for the halomethylation reaction are zinc, iron, tin, and aluminium metals, zinc oxide, chloride and bromide, stannic chloride, aluminium chloride and bromide, ferric chloride and antimony pentachloride. The halomethylation reaction may be carried out in the presence of porous bodies such as earth or sandy formations in order to seal them, or the halomethylated resins may be treated with ammonia and amines such as trimethylamine which replace halogen atoms to provide anion exchange resins.ALSO:The dimers, trimers, and tetramers of styrene, and the dimers and trimers of alpha methyl styrene and nuclear chlorostyrenes are catalytically halomethylated by treatment at a temperature of -10 DEG to 125 DEG C. with a halomethylating agent such as methylene chloride, bromide, and chloro-bromide, chloromethyl methyl ether, bromomethyl methyl ether, alpha, alpha1 dichlorodimethyl ether, alpha, alpha1 dibromodimethyl ether, mixtures of hydrogen chloride and formaldehyde, and mixtures of hydrogen iodide, paraformaldehyde, and an acid, the reaction being carried out in the present of a solvent such as carbon bisulphide or tetrachloroethylene; the halomethylating agent is employed in amount at least as great as that required to introduce into the starting material at least one halomethyl group per ten aromatic nuclei. Suitable catalysts for the halomethylation reaction are zinc, iron, tin, and aluminium metals, zinc oxide, chloride, and bromide, stannic chloride, antimony pentachloride, aluminium chloride and bromide and ferric chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US677350XA | 1948-12-29 | 1948-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB677350A true GB677350A (en) | 1952-08-13 |
Family
ID=22078039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28876/49A Expired GB677350A (en) | 1948-12-29 | 1949-11-10 | Improved method of preparing halomethylated polymers of alkenyl aromatic compounds |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1018768A (en) |
| GB (1) | GB677350A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001096476A2 (en) * | 2000-06-15 | 2001-12-20 | Exxonmobil Chemical Company Inc | Thermoplastic blend of a chloromethylated styrene-isobutylene copolymer and a thermoplastic resin |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE959228C (en) * | 1954-04-30 | 1957-02-28 | Bayer Ag | Process for the preparation of derivatives of polyvinyl aromatics |
| DE1068019B (en) * | 1956-11-02 | 1960-03-31 | Rohm a Haas Company, Philadelphia, Pa. (V. St. A.) | Process for the production of quaternary ammonium anion exchange resins |
| DE1745717A1 (en) * | 1957-03-09 | 1970-01-29 | Bayer Ag | Process for the production of crosslinked copolymers with a sponge structure |
| NL110165C (en) * | 1957-12-24 |
-
1949
- 1949-11-10 GB GB28876/49A patent/GB677350A/en not_active Expired
- 1949-12-06 FR FR1018768D patent/FR1018768A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001096476A2 (en) * | 2000-06-15 | 2001-12-20 | Exxonmobil Chemical Company Inc | Thermoplastic blend of a chloromethylated styrene-isobutylene copolymer and a thermoplastic resin |
| WO2001096466A2 (en) * | 2000-06-15 | 2001-12-20 | Exxonmobil Chemical Patents Inc. | Thermoplastic blend of a chloromethylated styrene-isobutylene-copolymer and a thermoplastic resin |
| WO2001096476A3 (en) * | 2000-06-15 | 2003-08-14 | Exxonmobil Chemical Company In | Thermoplastic blend of a chloromethylated styrene-isobutylene copolymer and a thermoplastic resin |
| WO2001096466A3 (en) * | 2000-06-15 | 2003-09-04 | Exxonmobil Chem Patents Inc | Thermoplastic blend of a chloromethylated styrene-isobutylene-copolymer and a thermoplastic resin |
| US6843292B2 (en) | 2000-06-15 | 2005-01-18 | Exxonmobil Chemical Patents Inc. | Thermoplastic blend |
| US6907911B2 (en) | 2000-06-15 | 2005-06-21 | Exxonmobil Chemical Patents Inc. | Thermoplastic blend |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1018768A (en) | 1953-01-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Stork et al. | Anions of protected cyanohydrins as acyl carbanion equivalents and their use in a new synthesis of ketones | |
| Holy | Reactions of the radical anions and dianions of aromatic hydrocarbons | |
| Crivello et al. | Diaryliodonium salts as thermal initiators of cationic polymerization | |
| GB1291819A (en) | Manufacture of benzylidene sorbitols | |
| Calvo et al. | Heterogeneous catalytic hydroarylation of olefins at a nanoscopic aluminum chlorofluoride | |
| GB677350A (en) | Improved method of preparing halomethylated polymers of alkenyl aromatic compounds | |
| EP0000090B1 (en) | Modified phenolic resins, method for their preparation and their use as selective metal chelating agents | |
| Fry et al. | Electrochemical and mercury-promoted reduction of. alpha.,. alpha.'-dibromophenylacetones in acetic acid | |
| Freeman et al. | Chromyl chloride oxidations. VI. Nature of the activated complex in the electrophilic addition to styrenes | |
| CA1037642A (en) | Process for the chloromethylation of styrene-divinylbenzene copolymers | |
| CN108384032A (en) | A method of preparing cross-linking type aryloxy polyphosphazene elastomer | |
| Olah et al. | Stable carbonium ions. CIV. Protonated alicyclic ethers and sulfides | |
| GB1104994A (en) | The improved process for perparation of living polymer | |
| Beak | Equilibration studies: The determination of the relative thermodynamic stabilities of one set of isomeric pyrones | |
| Kulkarni et al. | Cumyl phenyl sulfide forms bicumyl instead of cumyllithium upon reductive lithiation. Thiophenoxide as a leaving group in nucleophilic substitution by SET | |
| Gandini et al. | Cationic Polymerisation Initiation Processes with Alkenyl Monomers | |
| Hayano et al. | The Protonation of Aromatic Hydrocarbon Radical Anions. II. Interpretations of the Rate Constants in Terms of HMO Calculations | |
| Iwabuchi et al. | Preparation of macroreticular redox resins with hydroquinone and catechol units as pendant groups and their properties | |
| Gibson | Chemical Modification of Polymers. IV. Another Example of Facile Nucleaphilic Attack on a Polymer by a Reissert Anion | |
| Kapur | Chain transfer in the peroxide catalyzed polymerization of styrene | |
| US2548764A (en) | Chlorination of hydrocarbons | |
| Katsarava et al. | Synthesis of polyamides by active polycondensation. The structural and kinetical aspects of active esters aminolysis reactions | |
| CN109622594A (en) | A method of improving heavy metal pollution of soil using polymer absorption process | |
| Gotoh et al. | Radiation‐induced cationic dimerization and polymerization of styrene in methylene chloride solution. I | |
| Schramm et al. | The Alkali Metal Catalyzed Alkylation of Toluene with Propylene |