Patent GB-967597-A (GB)
Title: Process for the preparation of derivatives of polymers or copolymers of alpha,beta-ethylenically unsaturated aldehydes
IPC: C08G2/00
Filed: 1961-12-21
Abstract: Derivatives of polymers of ethylenically unsaturated aldehydes characterized by the presence of a plurality of structural units <FORM:0967597/C3/1> and <FORM:0967597/C3/2> and optionally <FORM:0967597/C3/3> in which the R's are hydrogen or similar or dissimilar hydrocarbon radicals, may be prepared by reacting the aldehyde polymer in the presence of a basic compound having a dissociation constant greater than 2.0 x 10-5 with (1) an aldehyde of formula RCHO where R is hydrogen or a hydrocarbon radical and/or (2) a ketone of formula R1COR1 where the R's are similar or dissimilar hydrocarbon radicals, or (3) compounds which liberate such aldehydes and ketones. Specified polymers are polymers of acrolein or beta ethyl, butyl, octyl or phenyl acrolein, and copolymers thereof with conjugated dienes, vinyl and allyl esters, ethylenically unsaturated hydrocarbons, acrylic and methacrylic esters and nitriles, vinyl and vinylidene halides, vinylamines and vinyl heterocyclic compounds. Specified basic materials are alkali metal, alkaline earth metal and ammonium hydroxides and strong amines.  Specified aldehydes are formaldehyde (trioxane and paraformaldehyde), acetaldehyde, propionaldehyde, butryaldehydes, valeraldehyde, crotonaldehyde, benzaldehyde and 1-naphthaldehyde, and specified ketones are methyl ethyl methyl isobutyl, dimethyl, diethyl, dibutyl, diisobutyl, ethyl octyl, methylphenyl, methyl cyclohexyl, dioctyl, allyl methyl and methyl isopropenyl ketones. Examples describe the reaction of polyacrolein with (I to III, VI and VIII) formaldehyde in the presence of sodium hydroxide, and the conversion of the products to sodium salts; the conversion of the products to (IV) ammonium and (V and VII) sodium, potassium and ammonium salts; (IX) the reaction of an acrolein ethyl acrylate copolymer with formaldehyde in the presence of sodium hydroxide; the use of copolymers of acrolein with (X) methyl acrylate or acrylonitrile; and the use of (XI) benzaldehyde and (XII) methyl ethyl ketone and ethyl butyl ketone. The products may be used for sizing paper and textile fibres, or dispersing agents and soil conditioners, and the salts thereof as stabilizers, paint driers, insecticides, wood preservatives, and oil additives. Ammonium and amine salts may be converted to amide and nitrile derivatives.  The polymers may be esterified or converted to lactones, reacted with polyisocyanates and polyisothiocyanates to form polyurethanes, or reacted with mercaptans and amines.ALSO:Textile yarns and fabrics may be sized with sizing materials comprising alkali metal and ammonium salts of polymers characterized by the presence of a plurality of structural units <FORM:0967597/D1-D2/1> and <FORM:0967597/D1-D2/2> and optionally <FORM:0967597/D1-D2/3> in which the R's are hydrogen or similar or dissimilar hydrocarbon radicals, which polymers may be prepared by reacting aldehydes or ketones, or compounds which yield aldehydes or ketones, with polymers of ethylenically unsaturated aldehydes in the presence of basic compounds having a dissociation constant greater than 2.0 x 10-5.  Examples describe the wash sizing of cotton yarns by padding with aqueous solutions of the (I-III, VI and VIII) sodium, (IV) ammonium, and (V and VII) sodium, potassium and ammonium salts of the reaction product of polyacrolein with formaldehyde in the presence of caustic soda; the sodium, potassium and ammonium salts of the reaction products of copolymers of acrolein with (IX) ethyl acrylate and (X) methyl acrylate, acrylonitrile or methyl ethyl ketone and formaldehyde; and sizes prepared as in Examples I to IV and X where the formaldehyde is replaced by (XI) benzaldehyde and (XII) methyl ethyl ketone or ethyl butyl ketone.  In Example XIII the sizes of Examples I to XI are applied to cotton fabrics, and in Example XIV the sizes of Examples I to X are applied to fabrics of rayon, nylon, polyacrylonitrile and polyethylene terephthalate.