Patent GB-1097598-A (GB)
Title: Novel polymers and their use in providing antistatic finishes on textile fibres
IPC: C08F20/16
Filed: 1964-12-09
Abstract: A polymer cross-linkable by heating to a cross-linked polymer of molecular weight 10,000-200,000 having a water-solubility at 25 DEG C. of less than 10 parts per million by weight is prepared by polymerizing a monomer mixture comprising 2-20% by weight of an ethylenically unsaturated monomer containing an epoxy or methylol group and 98-80% by weight of the copolymerizable ester <FORM:1097598/C3/1> wherein n = 4-40, L = phenyl substituted by alkyl of 1-20 carbon atoms or by two such alkyl groups which may be the same or different, and R1 = H or CH3.  The monomer mixture may also contain 1-4% by weight of an ethylenically unsaturated carboxylic acid containing 3-5 carbon atoms, e.g. acrylic, methacrylic or crotonic acid.  1-10% by weight (based on the addition polymer) of a tertiary amine (e.g. tris-(di-lower alkylamino lower alkyl) phenol or dimethylaminopropylamine) can be used to facilitate cross-linking. Suitable epoxy monomers include glycidyl acrylate or methacrylate, butadiene monoepoxide, vinyl epoxybutyrate, vinylcyclohexene oxide, vinyl epoxystearate, 1,2 - epoxy - 3 - allylphenoxy-propane, allyl epoxy stearate, 1,2-epoxy-3-allyloxy-propane, allyl epoxy undecanoate and dicyclopentadiene monoxide.  Methylol monomers specified are methylolmaleimide, methylol acrylamide, methylol - vinyl - piperazine, methylol - vinyl - melamine, methylolated acrylo - and methacrylo-guanamine, methylolated thiourea or guanidine derivatives containing vinyl groups, and alpha-methylolated alkyl vinyl ketones. Polymerization is preferably effected in a solvent such as dimethylformamide using an azo catalyst such as azo-di-isobutyronitrile; after terminating polymerization a stabilizer such as 2,6-di-t-butyl-4-methylphenol may be added to the resultant polymer solution or dispersion.  The polymers are suitable for providing textile fibres and fabrics with an antistatic finish (see Division D1).  The preparation is illustrated of the acrylate ester of Igepal CO-880 (nonyl phenol ether of polyethylene glycol containing 30 ethylene oxide units) by reacting Igepal CO-880 with (a) acrylic acid in toluene in the presence of sulphuric acid, nitrobenzene and hydroquinone, (b) acrylyl chloride in acetone in the presence of triethylamine, or (c) ethyl acrylate in the presence of 2,6-di-t-butyl-4-methylphenol and the sodium salt of ethylenediamine tetraacetic acid.  Method (a) is also used for the preparation of acrylate esters of other polyglycol ethers of nonyl, dodecyl and dinonyl phenols (see Example 7).ALSO:Textile fibres and fabrics are provided with an antistatic finish by impregnating the fibre or fabric with a non-aqueous solution, or aqueous dispersion, of a cross-linkable polymer obtained by polymerising a monomer mixture of 2-20% by weight of an ethylenically unsaturated compound containing an epoxy or methylol group and 98-80% by weight of the ester. <FORM:1097598/D1-D2/1> where n=4-40, L=phenyl substituted by alkyl of 1-20 carbon atoms or by two such alkyl groups which may be the same or different and R1=H or CH3, and optionally 1-4% by weight of an ethylenically unsaturated acid of 3-5 carbon atoms (e.g. acrylic, methacrylic or crotonic acid), and then heating the resultant material to cross-link the impregnated polymer to a molecular weight of 10,000-200,000 and a solubility in water at 25 DEG C of less than 10 p.p.m.  The fibres or fabrics are treated by the usual methods such as dipping, padding or spraying, or by flowing a solution of the polymer onto a continuous tow of fibres.  The polymer solution or dispersion may contain 1-10%, by weight of polymer, of a tertiary amine to assist in the subsequent cross-linking process.  The fibres and fabrics may be derived from natural or synthetic polymers, e.g. acrylic, nylon.  Dacron (registered Trade Mark) polyester, and wool.