Novel monomers, polymers, lacquers, and coated articles

Abstract

Abstract b -Methacryloxyisopropyl acid maleate is prepared by heating maleic anhydride, 2-hydroxypropyl methacrylate, benzene and hydroquinone. b -Acryloxyl(ethyl, isopropyl, butyl or decyl) acid maleates, succinates and phthalates, 6-methacryloxyhexyl acid maleate, 3-methacryloxy propyl acid succinate, 10-acryloxydecyl acid succinate, 4-acryloxybutyl acid phthalate, and b -methacryloxy-(ethyl, or isopropyl) acid maleates, succinates and phthalates and b -methacryloxydecyl acid succinate and b -methacryloxy-octyl and phthalate may be prepared similarly.ALSO:Copolymers comprise 0.25-99.75% of an acid of formula <FORM:0991904/C3/1> where R is H or CH3, A is C2- 10 alkylene, of which at least 2 C extend between the adjoining O atoms and Y is -CH2CH2-, -CH = CH-or o-phenylene, and 99.75-0.25% of at least one other ethylenically unsaturated monomer. When Y is -CH = CH-, the balance of the monomer mixture comprises a non-hydrocarbon monomer, e.g. methyl methacrylate or ethyl or n-butyl acrylate. The acid monomer may be b -methacryloxy-(isopropyl or ethyl)-acid (maleate, succinate or phthalate); b -acryloxy-(isopropyl or ethyl)-acid (maleate or succinate); b -methacryloxy-decyl acid succinate; b -methacryloxy-octyl acid phthalate; b -acryloxy-ethyl acid phthalate; 4-acryloxy-butyl acid phthalate; 10-acryloxy-decyl acid succinate; 3-methacryloxy-propyl acid succinate; 6-methacryloxy-hexyl acid maleate or their salts, e.g. amine, alkali metal or ammonium salts. The nonacid monomer may be acrylonitrile, methacrylonitrile; acrylic and methacrylic acids and their esters, amides and salts; itaconic acid and its drivatives, e.g. esters; diethyl citraconate; maleic anhydride; maleic and fumaric acids and their esters; vinyl ethers and esters; vinyl sulphides; styrene; vinyl toluene; and allyl esters of monocarboxylic acids. The copolymer may be prepared in bulk, solution (e.g. in dimethyl formamide), emulsion (using nonionic, cationic and/or anionic emulsifiers, a number of which are specified), or suspension to produce e.g. granules, 0.1-3% or more of a free radical catalyst, e.g. an organic or inorganic peroxide, a persulphate or an azo catalyst, may be used. A redoxy system may be used for emulsion polymerization together with a chain transfer agent or regulator, e.g. mercapto-ethanol. The copolymer may be isolated, if insoluble in the copolymerization solution, by filtering and washing, or by precipitation from a solution by adding a non-solvent for the copolymer, or by distilling off the solvent. A lacquer or enamel comprises 1/2 -10% copolymer in a solvent, e.g. xylene and/or butoxyethyl acetate and may contain methyl methacrylate and/or acrylic and methacrylic acid and esters. Aqueous emulsion dispersions of the polymers can be used as water-base paints or in alkaline spinning solutions.ALSO:Substrates are coated with a lacquer or enamel comprising 0,5-10% of the copolymer below in an organic solvent, e.g. xylene and/or butoxyethyl acetate. The copolymer comprises 0,25-99,75% of acid of formula H2C=CR-COOAOOC-Y-COOH, where R is H or CH3, A is a C2-10 alkylene of which at least 2 C atoms extend between the O atoms and Y is -CH2CH2-, -CH=CH- or o-phenylene and 99,75-0,25% of at least one other ethylenically unsaturated monomer. The substrates may be bare or primed metal such as steel, Al or brass; glass, asbestos, cement, shingles, leather, wood, paper and textiles. In an example, rutile TiO2 and copolymer solution containing xylol and 2-ethoxyethyl acetate (3 : 1 blend) was sprayed on to cold rolled steel panels primed with alkyd-epoxy resin primer which were then dried for 1/2 hour at 180 DEG F.ALSO:The shrinkage of wool is reduced by depositing on to a wool fabric 5-15% of the copolymer below from a 10-30% aqueous dispersion. The fabric after drying may be heated to 240-350F. for 1/4-1/2 hour. The copolymer comprises 0.25-99.75% of an acid of formula H2C = CR-COOAOOC-Y-COOH, where R is H or CH3, A is a C2-10 alkylene with at least 2 C between the O atoms and Y is a -CH2CH2-, -CH = CH- or o-phenylene group, and 99.75-0.25% of at least one other ethylenically unsaturated monomer.

Inventors

• 👤 David H Clemens

Bibliographic Details