Patent GB-1012798-A (GB)
Title: N-substituted acetamide compounds
IPC: C08G12/22
Filed: 1962-08-30
Abstract: Monomers of the formula <FORM:1012798/C3/1> wherein R represents hydrogen or methyl; R1 represents hydrogen, a saturated C1- 6 aliphatic hydroxy-substituted hydrocarbon radical having from 1 to 3 hydroxyl groups, or a (C1- 4) alkoxy-substituted hydrocarbon radical having from 1 to 6 carbon atoms excluding the carbon atom(s) in the alkoxy group; and R0 represents a saturated C1- 6 aliphatic hydroxy-substituted hydrocarbon group having from 1 to 3 hydroxyl groups or a (C1- 4) alkoxy-substituted hydrocarbon group having from 1 to 6 carbon atoms excluding the carbon atom(s) in the alkoxy group are (a) used as plasticizers for polyamides such as nylon 66, copolymers of vinyl or vinylidene chloride with acrylonitrile or vinyl acetate, copolymers of vinylchloride with vinylidene chloride, copolymers of acrylonitrile with vinyl acetate, vinyl pyridines, ethylene or isobutylene, and homopolymers of vinyl chloride, vinylidene chloride and acrylonitrile, the monomer being introduced into the melt, solution or dispersion of the polymer before its extrusion, casting or moulding into fibres, films, sheets or rods; (b) used as modifiers for aminoplast resinforming condensates such as those based on urea-formaldehyde or melamine-formaldehyde, a small amount of a free radical initiator being optionally included to induce addition polymerization before, during, or after the thermosetting condensation reaction; the compound may also enter into the polycondensation reaction; or (c) polymerized in bulk, solution, emulsion or suspension alone or in admixture with one or more other mono- or poly-ethylenically unsaturated comonomers in the presence of a polymerization catalyst.  Specified comonomers are 2- and 4-vinyl-pyridines, acrylonitrile, methacrylonitrile, acrylic, methacrylic and itaconic acids and their methyl, ethyl, isopropyl, butyl, tert.-butyl, octyl, dodecyl, octadecyl, octenyl and oleyl esters, diethyl and dimethyl maleates and fumarates, diethyl citraconate, diethyl chloromaleate, dimethylaminoethyl, tert.-butylaminoethyl and dimethyl aminopropyl, acrylates and methacrylates, acrylamide, methacrylamide, N-methylacrylamide, N - butyl - methacrylamide, dimethylaminoethyl - acrylamide and methacrylamide, dimethylaminopropyl - acrylamide and methacrylamide, hydroxyethyl, octyl, dodecyl, ureidoethyl, ureidoisobutyl, ethyl, and butyl vinyl ethers, butyl, methyl and dodecyl vinyl sulphides, vinyl acetate, propionate and laurate, styrene, a -methylstyrene, para-methylstyrene, para-chlorostyrene, vinyl toluene, vinyl naphthalene, vinylcarbozole, divinyl benzene, trivinylbenzene, ethylenediacrylate and dimethacrylate, bis - (vinyloxyethyl) - urea, and vinyloxyethyl acrylate and methacrylate.  Specified catalysts are benzoyl, acetyl and caproyl peroxides, butyl hydroperoxide, butyl perbenzoate, azodiisobutyronitrile, azodiisobutyramide, dimethyl, diethyl and dibutyl azodiisobutyrates, azobis - (a ,g  - dimethylvaleronitrile), azobis - (a  - methylbutyronitrile), azobis-(a  - methylvaleronitrile), dimethyl and diethyl azobismethylvalerates, hydrogen peroxide and sodium, potassium and ammonium persulphates, optionally in conjunction with reducing agents such as alkali metal sulphites, bisulphites, metabisulphites and hydrosulphites, or hydrazine.  Mercaptoethanol may be employed as a chain transfer agent.  Specified solvents are methanol, ethanol, isopropanol, 2 - methoxyethanol, ethyl acetate, ethoxyethyl acetate, acetonitrile, acetone, water, toluene, dimethylformamide and dimethylacetamide. Specified emulsifying agents are tert.-octyl, dodecyl and octadecyl phenoxypolyethoxyethanols, sodium lauryl sulphate, lauryl pyridinium chloride and (octylbenzyl) trimethyl ammonium chloride. The above polymers may be spun or cast to form fibres or films, may be used as flocculents, thickeners or adhesives, or may be used in admixture with water, 2-methoxyethanol, ethoxyethyl acetate, sodium or ammonium salts of a maleic acid/diisobutylene copolymer, titanium dioxide, zinc oxide, water-ground mica, hydroxyethyl cellulose, ethylene or diethylene glycol, tert.-octylphenoxy - polyethoxyethanol and dibutyl phthalate to provide water based paints, or curable coatings on glass, wood, metal or porcelain panels.ALSO:The invention comprises compounds of the formula:-<FORM:1012798/C2/1> wherein R represents hydrogen or methyl; R1 represents hydrogen, a saturated C1-6 aliphatic hydroxyl-substituted hydrocarbon group having from 1 to 3 hydroxyl groups, or a (C1-4) alkoxy-substituted hydrocarbon group having from 1 to 6 carbon atoms excluding the carbon atom(s) in the alkoxy group; and R0 represents a saturated C1-6 aliphatic hydroxyl-substituted hydrocarbon group having from 1 to 3 hydroxyl groups or a (C1-4) alkoxy-substituted hydrocarbon group having from 1 to 6 carbon atoms excluding the carbon atom(s) in the alkoxy group.  The compounds are prepared by reacting a compound of the formula CH2 = C(R)COOY with a compound of the formula XCH2CONR1R0, where Y represents silver or an alkali metal and X represents chlorine or bromine. The compounds may be polymerized or copolymerized, or may be reacted with alcohols, mercaptans, primary or secondary amines, nitroalkanes, malonates, acetoacetates or sodium bisulphite.  Alpha-halogenacetamides of the formula:-XCH2CONR0R1 are prepared by reacting an amine HNR0R1 with an ester of the formula:-XCH2COOR11 where R11 represents a C1-18 alkyl group.ALSO:Dodecyl mercaptan and dodecylamine reaction products of, homopolymers of, formaldehyde treated homopolymers of and copolymers of compounds of the formula:-  <FORM:1012798/D1-D2/1> wherein R represents hydrogen or methyl, R0 represents a saturated C1-6 aliphatic hydroxyl-substituted hydrocarbon group having from 1 to 3 hydroxyl groups or a (C1-4) alkoxy-substituted hydrocarbon group having from 1 to 6 carbon atoms excluding the carbon atom(s) in the alkoxy group, and R1 represents hydrogen or R0, are used alone or in admixture with starch, gelatine and aminoplasts such as formaldehyde condensates with urea, N, N1-ethyleneured, melamine, 5-(C1-4 alkyl)-substituted-tetrahydro-5-triazones-2 and 5-hydroxyethyl-tetrahydro-5-triazone-2, for sizing and imparting wet strength to paper by addition to the pulp; for sizing, softening, waterproofing and lubricating cotton, rayon and leather; and for shrink-proofing wool and bonding non-woven fabrics by padding with aqueous dispersions thereof, followed by drying and beating to 240-350 DEG F.ALSO:Polymers and copolymers of esteramides of the formula <FORM:1012798/B1-B2/1> wherein R represents hydrogen or methyl; R1 represents specified hydroxy or alkoxy substituted hydrocarbon radicals and R0 represents hydrogen or R1, are used (1) in aqueous dispersion for the primary coating of leather; (2) in admixture with water, sodium or ammonium salts of a maleic anhydride/diisobutylene copolymer, titanium oxide, zinc oxide, water ground mica, hydroxyethyl cellulose, ethylene or diethylene glycol and tert.-octylphenoxypolyethoxyethanol as brushing coats on white and yellow pine, oak, maple, cypress and Douglas fir panels, masonry, and wood panels previously primed with alkyd resin paints; (3) as solutions in 2-methoxyethanol or ethoxyethyl acetate for coating panels of wood, glass, porcelain, cold-rolled steel and metals previously primed with a mixture of an alkyd resin with a butylated methylolmelamine resin; and (4) in admixture with oxalic acid and bis-(methoxymethyl) urea, optionally plasticized with dibutyl phthalate, to provide cast films on glass panels, metal surfaces or previously primed metal surfaces, which are cured at 300  DEG F.