Patent GB-757285-A (GB)
Title: Substituted acrylamides and polymers thereof
IPC: C07C233/89
Filed: 1954-10-22
Abstract: Polymers of compounds of formul  <FORM:0757285/IV(a)/1> and <FORM:0757285/IV(a)/2> wherein R represents hydrogen, an alkyl radical of 1 to 3 carbon atoms, phenyl or cyclohexyl, R1 is a divalent saturated aliphatic hydrocarbon radical of 1 to 6 carbon atoms, R2 and R3 are the same or different and represent alkyl radicals of 1 to 3 carbon atoms, R5 represents an alkyl radical of 1 to 4 carbon atoms, X represents chlorine, bromine or iodine and R1 is a divalent saturated aliphatic hydrocarbon radical of 1 to 6 carbon atoms interposing one or two carbon atoms between the amino and carboxylic groups, are made by polymerizing said compounds alone or in admixture with other monomers.  The polymerization is effected in the manner described in Specifications 406,338, 501,169, 504,958 and 524,975.  The Specification contains extensive lists of monomers of the above general formul .  Other suitable monomers are esters of acrylic and substituted acrylic acids, vinyl esters, vinyl halides, vinylidene halides, styrene, allyl halides, allyl esters, N-acylallylamine derivatives and esters of maleic, fumaric, aconitic, itaconic and citraconic acids.  The polymers have film-forming properties and can be cast, extruded or coated to form hard, flexible, films, fibres or layers.  Those with hydrophilic properties are useful as gelatin substitutes. Specification 702,017 is referred to.  Reference has been directed by the Comptroller to Specification 546,459.ALSO:The invention comprises compounds of formul <FORM:0757285/IV(a)/1> and <FORM:0757285/IV(a)/2> wherein R represents a hydrogen atom, an alkyl radical of 1 to 3 carbon atoms, phenyl or cyclohexyl, R1 is a divalent saturated aliphatic hydrocarbon radical of 1 to 6 carbon atoms, R2 and R3 are the same or different and represent alkyl radicals of 1 to 3 carbon atoms, R5 represents an alkyl radical of 1 to 4 carbon atoms, X represents chlorine, bromine or iodine and R1 is a divalent saturated aliphatic hydrocarbon radical of 1 to 6 carbon atoms inertposing one or two carbon atoms between the amino and carboxylic groups.  R is preferably a methyl radical; R1 is preferably a -(CH2)n-radical where n is an integer from 2 to 6 and R1 is preferably a -CHR11-CHR111- radical where R11 and R111 are hydrogen or methyl or ethyl radicals, or a -CHR4- radical where R4 is hydrogen or a methyl, ethyl, propyl or isopropyl radical.  Compounds of the first formula, wherein R1 is a group interposing two carbon atoms, are prepared by reacting a dialkylaminoalkylacrylamide CH2=CR-CONH-R1-NR2R3 with a b -lactone, preferably in presence of an inert liquid diluent at a temperature of - 20 DEG  C. to +40 DEG  C. under substantially anhydrous conditions. Compounds of the second formula are prepared by reacting the above dialkylaminoalkylacrylamide with an alkyl ester of an a - or b -halogen substituted fatty acid, preferably in an inert liquid diluent at a temperature of - 20 DEG  C. to +60 DEG  C., or above 60 DEG  C. in the presence of a polymerization inhibitor. The compounds of the second formula may be converted into corresponding compounds of the first formula by alkaline hydrolysis and subsequent acidification to a pH of between 6.5 and 7.5.  Specified b -lactones are propiolactone, b -butyrolactone, b -isobutyrolactone and b -valerolactone. Specified a -halogen fatty acid esters are methyl, ethyl, propyl, isopropyl and butyl esters of chloroacetic, bromoacetic, iodoacetic, a -chloropropionic, a -bromopropionic, a -idopropionic, a -chlorobutyric, a -bromobutyric and a -iodobutyric acids.  Specified b -halogen fatty acid esters are methyl b -bromopropionate and methyl b -iodopropionate.  Specified dialkylaminoalkylacrylamides are those derived from acrylic, a -methacrylic, a -ethylacrylic, a -propylacrylic, a  - isopropylacrylic, a  - phenylacrylic and a -cyclohexylacrylic acids and dialkylaminoethylamine, -propylamine, -isopropylamine, -n-butylamine, -n-amylamine and -n-hexylamine, the dialkyl being preferably dimethyl, diethyl, methylethyl and methylpropyl.  The examples describe the preparation of the following betaines: N-3-methacrylamidopropyl - N : N - dimethyl - b  - aminopropionate, N - 2 - methacrylamidoethyl - N : Ndimethyl - b  - aminopropionate, N - 3 - acrylamidoethyl - N : N - dimethyl - b  - aminopropionate, N - 2 - acrylamidoethyl - N : N - dimethyl - b  - aminopropionate, N - 2 - methacrylamidoethyl - N : N - dimethylaminoacetate, N - 2 - methacrylamidoethyl - N : Ndimethylaminoacetate, N - 2 - methacrylamidoethyl - N : N - dimethyl - a  - aminopropionate, N - 2 - methacrylamidoethyl - N : N - diethylaminoacetate, N - 3 - methacrylamidopropylN : N - dimethylaminoacetate, N - 3 - methacrylamidopropyl - N : N - dimethyl - a  - aminopropionate, N - 3 - methacrylamidopropylN : N - diethylaminoacetate, N - 2 - acrylamidoethyl - N : N - dimethylaminoacetate, N - 2 - acrylamidoethyl - N : N - dimethyl - a -aminopropionate, N - 2 - acrylamidoethylN : N - diethylaminoacetate, N - 3 - acrylamidopropyl - N : N - dimethylaminoacetate, N - 3 - acrylamidopropyl - N : N - dimethyla  - aminopropionate and N - 3 - acrylamidopropyl - N : N - diethylaminoacetate, together with an extensive list of esters of thereof.  Specification 702,017 is referred to.  Reference has been directed by the Comptroller to Specification 546,459.