GB850311A - Aralkyl esters of unsaturated monocarboxylic acids and polymeric compositions obtained therefrom - Google Patents
Aralkyl esters of unsaturated monocarboxylic acids and polymeric compositions obtained therefromInfo
- Publication number
- GB850311A GB850311A GB30/57A GB3057A GB850311A GB 850311 A GB850311 A GB 850311A GB 30/57 A GB30/57 A GB 30/57A GB 3057 A GB3057 A GB 3057A GB 850311 A GB850311 A GB 850311A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- methacrylate
- dimethylbenzyl
- benzene
- compounds
- 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
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
Abstract
The invention comprises polymeric compounds derived from monomers of formula (R-R1)n-Ar wherein R is the radical derived by the removal of the carboxyl hydrogen atom from an alpha, beta-ethylenically unsaturated monocarboxylic acid, R1 is an alkylene radical, n is 1 or 2 and Ar is a phenyl radical having at least two ring substituents other than an (R-R1) group, said substituents being alkyl or haloalkyl radicals having from 1-4 carbon atoms (see Group IV(b)). Specified monomers include dimethylbenzyl acrylate, 1:4-dimethyl -3:5- dimethacryloxymethyl-or-diacryloxymethyl - benzene, 1:4-dimethyl-3-chloromethyl - 5 - acryloxymethyl-ormethacryloxymethyl-benzene, and 1:4-dimethyl-3-acryloxymethyl-5- methacryloxymethylbenzene. The monomers may be used to prepare homopolymers and also interpolymers by copolymerisation with other monomers such as olefinic hydrocarbons, halo-olefinic hydrocarbons, alkenyl nitriles and unsaturated esters, acids and amides. The polymerisation is carried out in bulk, in solution or by emulsion or bead methods using inorganic or organic peroxidic compounds or diazo compounds as catalysts. In examples the polymerisation of the following monomers or mixtures thereof is specified: dimethylbenzyl methacrylate; 1:5-dimethyl - 2:4 - dimethacryloxymethyl- and -diacryloxymethylbenzenes; 1:5-dimethyl - 2:4 - dimethacryloxymethylbenzene and methyl methacrylate or dimethyl methacrylate; 1:5-dimethyl - 2:4-dimethacryloxymethyl benzene, dimethylbenzyl methacrylate and triallyl cyanurate; 1:5-dimethyl-2:4-dimethacryloxymethylbenzene, dimethylbenzyl methacrylate and triallyl cyanurate with or without allyl methacrylate; dimethylbenzyl methacrylate, acrylamide and ethyl acrylate are copolymerised in butanol solution and the mixture reacted further with a butanol solution of formaldehyde and maleic anhydride to give a film-forming resin (see Group III); dimethylbenzyl methacrylate, styrene and propylene maleate phthalate polyester, diethylene glycol bis (allyl carbonate), 1:5 dimethyl-2:4-dimethacryloxymethylbenzene, dimethylbenzyl methacrylate, methyl methacrylate and diallyl itaconate.ALSO:The invention comprises compounds of formula: (R-R1)n-Ar wherein R is the radical derived by the removal of the carboxyl hydrogen atom from an alpha, beta-ethylenically unsaturated monocarboxylic acid, R1 is an alkylene radical, n is 1 or 2 and Ar is a phenyl radical having at least two ring substituents other than an (R-R1) group, said ring substituents being alkyl or haloalkyl radicals having from one to four carbon atoms. The compounds are used to form polymeric compositions (see Group IV(a)). They are prepared by reacting the corresponding mono- or dihaloalkyl-benzenes with salts of alpha, beta-unsaturated acids. Specified acids are acrylic, methacrylic, 2-butenoic, 2-methyl-2-propenoic and oleic. In an Example a mixture of monochloromethyl-p-xylene, potassium methacrylate, hydroquinone, methacrylic acid, and dimethylformamide is refluxed, potassium chloride is filtered off, the filtrate is washed with dimethyl formamide and water and the product extracted with toluene. The toluene layer is washed with water, dried and distilled in vacuo to give 2 : 5-dimethylbenzyl methacrylate. Further compounds prepared similarly are 1 : 4-dimethyl-3 : 5-dimethacryloxymethyl-benzene, dimethylbenzyl acrylate (mixture of isomers) and 1 : 5-dimethyl-2 : 4-diacryloxymethyl-benzene. Further compounds specified are 1 : 4-dimethyl-3-chloromethyl-5-acryloxymethyl-or-methacryloxymethyl benzene, 1 : 4-dimethyl-3 : 5-diacryloxymethylbenzene and 1 : 4-dimethyl-3-acryloxymethyl-5-methacryloxymethyl-benzene.ALSO:Steel and glass plates are coated with a resin composition obtained by copolymerizing dimethylbenzyl methacrylate, acrylamide and ethyl acrylate in butanol solution and treating the mixture obtained with a butanol solution of formaldehyde and maleic anhydride and the films baked. The composition can be pigmented with titanium dioxide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US850311XA | 1956-01-05 | 1956-01-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB850311A true GB850311A (en) | 1960-10-05 |
Family
ID=22189027
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30/57A Expired GB850311A (en) | 1956-01-05 | 1957-01-01 | Aralkyl esters of unsaturated monocarboxylic acids and polymeric compositions obtained therefrom |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB850311A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5041511A (en) * | 1989-01-26 | 1991-08-20 | Menicon Co., Ltd. | Ocular lens material |
-
1957
- 1957-01-01 GB GB30/57A patent/GB850311A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5041511A (en) * | 1989-01-26 | 1991-08-20 | Menicon Co., Ltd. | Ocular lens material |
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