Patent GB-1007820-A (GB)
Title: Improvements in and relating to sulfophenoxyalkoxy-aromatic dicarboxylic acids, salts and esters and dyeable polyesters
IPC: C07C69/92
Filed: 1962-10-30
Abstract: The invention comprises a dyeable linear polyester which is a condensation product of an aromatic dicarboxylic acid or dialkyl ester thereof with a diol, such as an acrclic or alicyclic aliphatic glycol, an aromatic diol, an aliphatic-aromatic diol, or a diester thereof, and from 0.1 to 10 mole per cent, based on the total amount of dicarboxylic acid compounds present, of a sulphonated compound of the formula <FORM:1007820/C3/1> wherein M designates an alkali metal atom, n is an integer from 1 to 12, Ar is an arenyl radical, and R is a hydrogen atom or an alkyl radical having 1 to 8 carbon atoms. Linear polyesters may also be made from a hydrocarboxylic acid or ester thereof with a sulphonated compound as above, or by the partial replacement of a diol or aromatic dicarboxylic acid or ester with a hydroxycarboxylic acid or ester in the above polyesters.  A monofunctional aromatic acid or ester can also be added as a molecular weight regulator.  Illustrative of molecular weight regulators which can also serve as dye-assistants are compounds of the formula <FORM:1007820/C3/2> according to Specification No. 40928/62.  In Examples (3) to (8) describe the preparation of polyesters from dimethyl terephthalate, ethylene glycol and dimethyl 5-(2-[4-(sodiumsulpho) phenoxy]ethoxy)-isophthalate; (9) includes also methyl (2 - [sodiumsulpho]phenoxy) acetate ; (10) includes methyl benzoate; (11) uses dimethyl 2-(5-[4-potassiumsulpho-phenoxy]-pentoxy) terephthalate; (12) is as in (11) but includes methyl 6-(4-[sodiumsulpho[phenoxy) hexanoate; and (13) describes a polyester from dimethyl terephthalate, dimethyl isophthalate, dimethyl 2-(5-[4-lithiumsulpho-phenoxy]pentoxy) terephthalate and 1,4 - cyclohexanedimethanol.  Polyesterification is effected in the presence of the usual catalysts and, possibly, titanium dioxide. The polyesters may be melt-spun to form filaments and yarns which can be woven into fabrics and dyed by conventional techniques.ALSO:The invention comprises compounds of the formula <FORM:1007820/C2/1> in which X is an -SO3H or -SO3M radical, wherein M is an alkali metal, n is an integer from 1 to 12, Ar is an arenyl radical, i.e. a trivalent aromatic hydrocarbon radical, such as a phenenyl or naphthenyl radical, and R is a hydrogen atom or an alkyl radical having 1 to 8 carbon atoms.  The novel compounds may be made by reacting a phenoxyalkoxyphthalic acid or ester of the formula above where X is hydrogen, and Ar, n and R are as above, with a sulphonating agent comprised of a mixture of sulphuric acid and acetic anhydride, at a temperature of from -15 DEG  to 50 DEG  C. The acid or ester is preferably introduced into the sulphonating agent in solution in an inert solvent, such as methylene dichloride, ethylene dichloride or ethyl acetate.  The sulphonated phenoxy alkoxyphthalic acid or ester can be reacted with an alkali metal hydroxide or lakoxide or an alkali metal salt of an acid weaker than sulphonic acid, such as acetic or benzoic, to form the corresponding alkali metal sulphonate.  The phenoxyalkoxyphthalic acids and esters, used as starting materials, may be obtained by the reaction of a phenoxyalkyl halide with an alkali metal dicarboxy or dicarbalkoxy phenolate, in a solvent such as ethanol, N,N-dimethylformamide or dioxane at a temperature of from 20 DEG  to 100 DEG  C.  Examples describe the preparation of (1) dimethyl 5 - (2 - phenoxy - ethoxy) isophthalate, its sulphonation to dimethyl 5-(2-[4-sulphophenoxy] ethoxy) isophthalate and sodium salt formation; dibutyl 5-(2-[4-potassiumsulpho) phenoxy] ethoxy) isophthalate; (2) dimethyl 2 - (5 - phenoxypentoxy) - terephthalate, its sulphonation to dimethyl 2-(5-[4-sulphophenoxy] pentoxy) terephthalate and its conversion to dimethyl 2-(5-[4-(potassiumsulpho) phenoxy] pentoxy) terephthalate and the corresponding lithium salt; diethyl 2-(8-[4-(sodiumsulpho) phenoxy] octoxy) terephthalate.