Patent GB-648254-A (GB)
Title: Alpha-substituted n-hydroxyalkylacrylamides
IPC: C08F20/58
Filed: 1946-10-02
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.