Patent GB-759854-A (GB)
Title: Detersive polyoxyethylene ethers and compositions thereof
Inventor: BARKER GEORGE ERNEST
IPC: C11D1/72
Filed: 1953-04-14
Abstract: The invention comprises a polyoxyethylene mono-ether reaction product of from 10 to 20 molar proportions of ethylene oxide with one molar proportion of a saturated multi-branched chain alcohol, or mixture of such alcohols, containing from 11 to 15 carbon atoms per mol. and having the configuration characteristic of alcohols produced by the oxo synthesis from C10 to C14 olefinic polymers of propylene, isobutylene or mixtures of propylene and isobutylene.  The multi-branched chain alcohols may be prepared from the olefinic polymers by the oxo synthesis itself or by other methods yielding alcohols of the required configuration, for example, by forming the hydrogen bromide addition product of the olefine which is reacted with metallic magnesium to form the corresponding Grignard reagent, followed by reaction with formaldehyde and then acid hydrolysis.  The preferred alcohols are those obtained by the oxo synthesis from tri-isobutylene and/or tetrapropylene.  The ethers may be prepared by reaction of the alcohols with ethylene oxide under conditions of elevated pressure and temperature as described in Specification 380,431, In an example tridecyl alcohol obtained by the oxo synthesis from tetrapropylene is heated at 100-130 DEG  C. in presence of sodium methylate in an autoclave and ethylene oxide fed in at 30 p.s.i.g., the product being a mixture of mono-ethers of tridecyl alcohol averaging 14 oxyethylene groups per mol. Other poly-oxyethylene ether-products referred to include an ether derived from a tridecyl alcohol obtained by the oxo synthesis from triisobutylene and containing 12 oxyethylene groups, an ether derived from a tetradecyl alcohol obtained likewise from a polymer of 3:1 propylene-butylene mixture, and containing 16 oxyethylene groups and an ether derived from a pentadecyl alcohol obtained likewise from a C14 polymer prepared by polymerizing about equimolar quantities of propylene and isobutylene, and containing 14 oxyethylene groups.  The products are detergents (see Group III) and vary from viscous liquids to soft waxes.  They may be converted into a solid form by intimate mixing with finely divided crystalline urea which may be in the solid or molten condition and in examples (1) two parts by weight of urea and one part of a polyoxyethylene ether of an oxo alcohol, prepared from tri - isobutylene, containing 16 oxyethylene groups, are mixed together into a paste at room temperature and on standing a solid product is formed; (2) equal parts of urea and a polyoxyethylene ether of an oxo alcohol, formed from tetrapropylene, containing 12 oxyethylene groups are heated together at 110-115 DEG  C. with some water and the liquid mixture is sprayed down a cooling column whereby a solid granular product is obtained.  Specification 683,383 also is referred to.ALSO:Synthetic detergents comprise a polyoxyethylene mono-ether reaction product of from 10 to 20 molar proportions of ethylene oxide with one molar proportion of a saturated multi-branched-chain alcohol, or mixture of such alcohols, containing from 11 to 15 carbon atoms per molecule and having the configuration characteristic of alcohols produced by the oxo synthesis from C10 to C14 olefinic polymers of propylene, isobutylene or mixtures of propylene and isobutylene (see Group IV(b)). ethers may be used singly or as mixtures thereof and, if desired, in conjunction with alkaline builders such as alkali metal carbonates, phosphates, borates and silicates, suspending agents such as sodium carboxymethyl cellulose and extruding agents such as sodium sulphate or chloride. The ethers are viscous liquids as soft waxes and may be converted into a solid form by incorporation of urea. Examples of detergent compositions are (1) a polyoxyethylene ether of a tridecyl alcohol, obtained by the oxo synthesis from tri-isobutylene having 12 oxyethylene groups, sodium carboxymethyl cellulose, sodium tripolyphosphate, sodium metasilicate and sodium carbonate; (2) a polyoxyethylene ether of a tetradecyl alcohol, obtained by oxo synthesis from a propylene/isobutylene polymer, the ether having 16 oxyethylene groups, tetrasodium pyrophosphate, sodium sesquicarbonate and water; (3) a polyoxyethylene ether, having 14 oxyethylene groups, of pentadecyl alcohol obtained by the oxo synthesis from a propylene/isobutylene polymer, sodium carboxymethyl cellulose, tetrasodium pyrophosphate, sodium ortho silicate and soda ash.  In examples describing solid urea-ether products (1) urea and a poly oxyethylene ether of an oxo alcohol from tri-isobutylene and having 16 oxyethylene groups are mixed together and then allowed to stand, forming a hard mass; the freshly formed mixture may first be extruded in sheet or ribbon form; (2) urea and a polyoxyethylene ether of a tridecyl oxo alcohol containing 12 oxyethylene groups are heated with some water and the resulting liquid sprayed down a cooling column to give a solid granular product.  Specifications 380,431 and 683,383 are referred to.