GB874235A - Unsaturated esters of polyoxyalkylene glycols - Google Patents
Unsaturated esters of polyoxyalkylene glycolsInfo
- Publication number
- GB874235A GB874235A GB22122/58A GB2212258A GB874235A GB 874235 A GB874235 A GB 874235A GB 22122/58 A GB22122/58 A GB 22122/58A GB 2212258 A GB2212258 A GB 2212258A GB 874235 A GB874235 A GB 874235A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- butyl
- added
- cresol
- tert
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Acrylic and methacrylic esters of polyoxyalkylene glycols or of their mono-alkyl ethers are prepared by reacting acrylic or methacrylic acid, anhydride, acid halide or ester with the polyoxyalkylene compound, containing, as a stabilizer, a phenolic compound of the formula: <FORM:0874235/IV (a)/1> where R1 is hydrogen, alkyl or alkoxy, and R2 and R3 are hydrogen or alkyl, at least one being alkyl when R1 is hydrogen or alkyl. The stabilized polymers are prepared as described in Specification 874,234. Specified stabilizers are 2, 6- di-tert. butyl-p-cresol, p-hydroxyanisole, 2, 6-di-tert. butyl-phenol, 2-tert. butyl-p-cresol, 2-butyl-p-hydroxy-anisole, 2, 6-dibutyl-p-hydroxy -anisole, and 2, 6-dimethyl-p-cresol. A solvent is generally first added to the stabilized polymer, e.g. toluene, heptane, benzene, cyclohexane, and isopropyl ether. Polymerization inhibitors are also preferably included, e.g. hydroquinone, copper powder, cupric salts and their chelates. Esterification catalysts, such as sulphuric, benzene sulphonic and toluene sulphonic acids, are added, the mixture heated to reflux, e.g. 100 DEG -110 DEG C., and the acrylic compound is added, preferably in slight excess. Oxygen may be introduced when employing reduced pressures and hydroquinone as inhibitor. The product is neutralized with alkaline material and may be washed. Further inhibitor is then preferably added. The examples describe the preparation of: (1) and (2) polyoxyethylene glycol (200) and (300)-dimethacrylate; (3) polyoxyethylene glycol (600)-diacrylate; (4) polyoxypropylene glycol (1869)-dimethacrylate; (5) the monomethacrylic ester of polyoxypropylene-glycol monobutyl ether (3,000).ALSO:Acrylic and methacrylic esters of polyoxyalkylene glycols or of their mono-alkyl ethers are prepared by reacting acrylic or methacrylic acid, anhydride, acid halide or ester with the polyoxyalkylene compound, containing, as a stabilizer, a phenolic compound of the formula <FORM:0874235/IV (b)/1> where R1 is hydrogen, alkyl or alkoxy, and R2 and R3 are hydrogen or alkyl, at least one being alkyl when R1 is hydrogen or alkyl. The stabilized polymers are prepared as described in Specification 874,234. Specified stabilizers are 2,6-di-tert.butyl-p-cresol, p-hydroxyanisole, 2,6-di-tert.butyl phenol, 2-tert. butyl-p-cresol, 2-butyl-p-hydroxy-anisole, 2,6-dibutyl-p-hydroxyanisole and 2,6-dimethyl-p-cresol. A solvent is generally first added to the stabilized compound, e.g. toluene, heptane, benzene, cyclohexane and isopropyl ether Polymerization inhibitors are also preferably included, e.g. hydroquinone, copper powder, cupric salts and their chelates. Esterification catalysts, such as sulphuric, benzenesulphonic and toluenesulphonic acids, are added, the mixture heated to reflux, e.g. 100 DEG -110 DEG C., and the acrylic compound is added, preferably in slight excess. Oxygen may be introduced when employing reduced pressures and hydroquinone as inhibitor. After neutralising with alkaline material and optional washing, further inhibitor is preferably added. The examples describe the preparation of: (1) and (2) polyoxyethylene glycol (200) and (300)-dimethacrylate; (3) polyoxyethylene glycol (600)-diacrylate; (4) polyoxypropylene glycol (1869) - dimethacrylate; and (5) the monomethacrylic ester of polyoxypropylene glycol monobutyl ether (3000).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US874235XA | 1957-07-11 | 1957-07-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB874235A true GB874235A (en) | 1961-08-02 |
Family
ID=22205103
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22122/58A Expired GB874235A (en) | 1957-07-11 | 1958-07-10 | Unsaturated esters of polyoxyalkylene glycols |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB874235A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1247824A3 (en) * | 1997-06-10 | 2006-07-19 | Nippon Shokubai Co., Ltd. | Process for producing a polycarboxylic acid as an effective compound for a cement admixture |
-
1958
- 1958-07-10 GB GB22122/58A patent/GB874235A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1247824A3 (en) * | 1997-06-10 | 2006-07-19 | Nippon Shokubai Co., Ltd. | Process for producing a polycarboxylic acid as an effective compound for a cement admixture |
EP0884290B2 (en) † | 1997-06-10 | 2011-11-09 | Nippon Shokubai Co., Ltd. | Process for producing a polycarboxylic acid |
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