GB648254A - Alpha-substituted n-hydroxyalkylacrylamides - Google Patents
Alpha-substituted n-hydroxyalkylacrylamidesInfo
- Publication number
- GB648254A GB648254A GB29409/46A GB2940946A GB648254A GB 648254 A GB648254 A GB 648254A GB 29409/46 A GB29409/46 A GB 29409/46A GB 2940946 A GB2940946 A GB 2940946A GB 648254 A GB648254 A GB 648254A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polymerization
- chloride
- dihydroxy
- polymerized
- propylamine
- 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
- C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
Landscapes
- 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
Polymerized a -substituted mono-(N-hydroxy alkyl) acrylamides are prepared by the polymerization of the corresponding monomers having as the a -substituent a hydrocarbon radical or halogen. Polymerization may be effected at or below room temperature with the aid of ultra-violet light or by means of a polymerization catalyst or heat. Polymerization in the presence of an organic solvent such as acetone or water gives a gel or viscous solution. The monomers may be interpolymerized with monomeric compounds containing the radical CH2=C<, e.g. vinyl compounds such as vinyl acetate or chloride, acrylic compounds such as acrylic acid, methacrylic acid, acrylonitrile and methacrylamide. The preparation of the monomers, which are stated to be novel, is given (see Group IV (b)). In an example, N-b -ethanolmethacrylamide is heated in water in the presence of benzoyl peroxide yielding a thermo-irreversible gel. Corresponding amides derived from gamma-hydroxy propylamine, a : b -dihydroxy propylamine, b : b 1-dihydroxyisopropylamine and b : b 1-dihydroxy-tert.-butylamine and from acrylyl chlorides having as an a -substituent such radicals as ethyl, propyl, isopropyl, butyl, phenyl, methyl phenyl, cyclohexyl or methyl cylcohexyl or bromine or chlorine may also be so polymerized. The subject-matter of Specification 648,252 is disclaimed. The Specification as open to inspection under Sect. 91 relates to the polymerization of a -substituted mono-(N-hydroxy alkyl) acrylamides in general and contains further examples wherein (1) ethanolamine in dioxane solution is reacted with a diethyl ether solution of methacrylyl chloride whereby N-ethanol methacrylamide is formed as a rubbery polymer; (2) monomeric N-ethanol methacrylamide is polymerized in methanol. This subject-matter does not appear in the Specification as accepted.ALSO:Alpha-substituted mono-(N-hydroxyalkyl)-acrylamides are prepared by reacting a -substituted acrylyl chlorides, containing as the a -substituent a halogen or hydrocarbon radical, with at least an equimolecular amount of a free hydroxy alkyl primary amine. It is preferred to carry out the reaction at between 0 DEG and 25 DEG C. in presence of an organic solvent. Preferably excess of the amine is employed to neutralize the hydrogen chloride formed; if stoichiometrical proportions of reactants are employed, an additional alkali such as sodium or potassium hydroxide or sodium carbonate is preferably employed. The products may be polymerized (see Group IV (a)). In an example, methacrylyl chloride is reacted with excess ethanolamine in acetone, the oily layer of ethanolamine hydrochloride formed is removed and the acetone stripped from the monomeric product N-ethanol methacrylamide. Similar products may be obtained using gammahydroxy propylamine, a : b -di-hydroxy propylamine, b : b 1 - dihydroxy isopropylamine and b : b 1 - dihydroxy - tert. - butylamine and a -chloro-, bromo-, ethyl-, propyl-, isopropyl-, butyl-, phenyl-, methyl phenyl-, cyclohexyl-, and methyl-cyclohexyl acrylyl chlorides. Specifications 401,435 and 475,131 are referred to. The subject-matter of Specification 648,251 is disclaimed. The Specification as open to inspection under Sect. 91 relates to the use of any a -substituted acrylyl chloride and is not limited as regards proportions of reactants. In a further example, ethanolamine in dioxane solution is reacted with an equal part of methacrylyl chloride in diethyl ether yielding N-ethanol methacrylamide which polymerizes as it is formed. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US648254XA | 1945-10-16 | 1945-10-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB648254A true GB648254A (en) | 1951-01-03 |
Family
ID=22058472
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29409/46A Expired GB648254A (en) | 1945-10-16 | 1946-10-02 | Alpha-substituted n-hydroxyalkylacrylamides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB648254A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1374828A1 (en) * | 2002-06-26 | 2004-01-02 | Ivoclar Vivadent AG | Dental material on the basis of hydroxyalkyl acrylamides |
CN102617787A (en) * | 2012-03-21 | 2012-08-01 | 东南大学 | Hydrogel contact lens material and preparation method thereof |
-
1946
- 1946-10-02 GB GB29409/46A patent/GB648254A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1374828A1 (en) * | 2002-06-26 | 2004-01-02 | Ivoclar Vivadent AG | Dental material on the basis of hydroxyalkyl acrylamides |
DE10228540A1 (en) * | 2002-06-26 | 2004-01-22 | Ivoclar Vivadent Ag | Dental materials based on hydroxyalkylacrylamides |
CN102617787A (en) * | 2012-03-21 | 2012-08-01 | 东南大学 | Hydrogel contact lens material and preparation method thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2524432A (en) | Esters of epoxy alcohols with propenoic compounds | |
US2311548A (en) | Polymers of amides of alpha-methylene monocarboxylic acids | |
US2348705A (en) | Ethylenesulphonyl polymer | |
GB351508A (en) | Improvements in the manufacture and production of artificial masses and articles therefrom | |
KR930004257A (en) | Method for preparing fluoxetine and novel intermediates | |
US2586995A (en) | Polyfurcate azonitriles | |
GB702017A (en) | Improvements relating to acrylonitrile compositions | |
GB840908A (en) | Sulpho esters of alpha-methylene carboxylic acids and polymers thereof | |
US3177187A (en) | Sym-tetrafluorodichloroisopropyl acrylate compounds and polymers thereof | |
US2834763A (en) | Copolymers of trifluoroethyl acrylate | |
GB967503A (en) | Improvements relating to photographic colour formers | |
GB648254A (en) | Alpha-substituted n-hydroxyalkylacrylamides | |
US2694699A (en) | Alpha-sulfonoxy acrylates and polymers thereof | |
US2579384A (en) | N,n-disubstituted vinyl dithiocarbamates | |
US2541465A (en) | Alpha-fluoromethacrylamides and polymers thereof | |
GB705887A (en) | ||
US2675371A (en) | Polymers of alpha-sulfo and sulfonamidomethyl acrylonitriles | |
US2592248A (en) | Alpha-acylamino acrylamides and polymers thereof | |
US3013001A (en) | N-substituted pyrazole compounds and polymerization products thereof | |
US2728749A (en) | Fluoroalkyl vinyl sulfonates and polymers thereof | |
US3432484A (en) | Preparation of thermoplastic polymers by low temperature polymerization of vinyl monomers | |
US2515132A (en) | Interpolymers of diallyl esters of diethyl ether-dicarboxylic acids | |
CA1147750A (en) | Process for the preparation of antioxidant amides | |
GB836755A (en) | Improvements in and relating to polymers | |
US2659715A (en) | Alpha-acylaminomethyl acrylonitriles and polymers thereof |