GB1406869A - Preparation of reaction products of epoxides and epoxy- silicones processes for their manufacture and their use - Google Patents

Abstract

1406869 Reaction products of epoxides and epoxy-silicones CIBA-GEIGY AG 6 Nov 1972 [11 Nov 1971] 51123/72 Headings C3B and C3T [Also in Division D1] Stable preparations of epoxide reaction products are prepared by reacting (a) a reaction product of (a 1 ) an epoxide which contains at least 2 epoxide groups per molecule and is free of siloxane groups, (a 2 ) an epoxy-silicone which contains at least 2 epoxide groups and (a 3 ) a C 12 -C 22 fatty amine with (b) an aliphatic saturated dicarboxylic acid or a polyaminoamide in the presence of an oganic solvent at 25 degrees to 120‹ C. and optionally subsequently further reacting with (C) a polyfunctional compound which possesses, as functional groups or atoms, mobile halogen, vinyl or carboxylic acid ester groups and optionally at most one carboxylic acid, cyano, hydroxyl or epoxide group. Preferred epoxides (a 1 ) are derived from polyhydric phenols or polyphenols such as resorcinol or phenol-formaldehyde condensates, or more particularly from bis-phenols, e.g. a polyglycidyl ether of 2,2-bis-(4<SP>1</SP>-hydroxyphenyl)-propane. The epoxy-silicone component (a 2 ) preferably has an average molecular weight of 10<SP>3</SP> to 10<SP>6</SP> and contains structural units of the formula -(R 1 R 2 )SiO-, and -(R 3 )(Q)Si-O-, wherein R 1 -R 3 are C 1 -C 10 alkyl or alkoxy radicals, or an aryl radical and Q is a monovalent organic radical, preferably a C 3 -C 8 aliphatic radical, which carries a vicinal epoxide group. Preferred monofatty amines (a 3 ) have the formula H 3 C(CH 2 ) x NH 2 wherein x = 11- 21. Preferred components (b) are aliphatic saturated dicarboxylic acids of at least 7 carbon atoms which can optionally be used together with an anhydride of an aromatic dicarboxylic acid with at least 8 carbon atoms or of an aliphatic mono- or di-carboxylic acid with at least 4 carbon atoms. Preferred acids (b) have the formula HOOC(CH 2 ) y COOH where y=5- 12, and preferred anhydrides are maleic or phthalic anhydride. Component (b) can also be a polyaminoamide which is preferably obtained by condensation of a polymeric unsaturated fatty acid, preferably aliphatic ethylenically unsaturated dimeric to trimeric fatty acids, with a polyalkylenepolyamine. The preferred polyaminoamide is a reaction product of dimerized to trimerized linoleic or linolenic acid with a polyamine of the formula wherein n = 1, 2 or 3. Preferred component (c) is an epihalogenohydrin, others being glycerine dichlorohydrin, acrylic acid, methylolacrylamide and acrylonitrile. In order to ensure that the reaction products are soluble or dispersible in water the pH of the reaction mixture is adjusted not later than after the completion of the reaction to 7À5-12 if component (b) used is a dicarboxylic acid, and to 2-8 if (b) used is a polyaminoamide. The stable preparations can be used for finishing textiles, to which preparations are preferably added adducts of fatty amines with 12-22 carbon atoms and 6-30 mols of ethylene oxide which are preferably esterified with at least dibasic oxygen-containing acids. In the examples the epoxy-silicone component (a 2 ) is prepared by first preparing a hydrogencontaining polymethylsiloxane by copolymerizing the following silicones in the presence of concentrated sulphuric acid: α,#-bis-trimethylsiloxypolydimethylsiloxane, α,#-bis-trimethylsiloxy-polymethyl-H-siloxane, octamethylcyclotetrasiloxane and hexamethyldisiloxane. The resulting silicone oil is then reacted with allyl glycidylether using chloroplatinic acid as catalyst to produce polyglycidoxypropylsiloxane (a 2 ). Next the reaction product (a) is prepared by reacting an epoxide formed from 2,2-bis- (41-hydroxyphenyl)-propane and epichlorohydrin, the above epoxy silicone (a 2 ) and a mixture of 1-aminoeicosane and 1-aminodocosane in n-butylglycol, which is then reacted with sebacic acid in Example 1 or a condensation product of polymerized oleic acid and diethylenetriamine in Example 4 as component (b), and then with epichlorohydrin (component C). The resulting mixture in Example 1 is diluted with trichloroethylene to which is added triethylamine and an adduct of ethylene oxide and a fatty amine mixture (C 16 -C 22 ), which is further diluted with water to form an emulsion. The resulting mixture of Example 4 is diluted with glacial acetic acid and water. The preparations are used for treating wool yarn.