Patent GB-793113-A (GB)
Title: New carboxymethylated glycol ethers and their preparation
IPC: C08G65/332
Filed: 1955-07-11
Abstract: The invention comprises water-soluble carboxymethylated glycol ethers of C13 branched-chain primary alcohols having the general formula: R-(O-CH2CH2)n-O-CH2COOM, wherein R is an alkyl radical derived from the C13 primary alcohol, n is any integer from 1 to 10 and M is hydrogen or other cation, and mixtures of these compounds with the corresponding uncarboxymethylated ethers.  The products may be prepared by condensing the C13 alcohol with 1 to 10 mols. of ethylene oxide and partially or completely carboxymethylating the resulting glycol ether by reaction with a mono-halo acetic acid or salt thereof, and if necessary, acidifying the reaction product when the free carboxymethyl acid is desired.  Tetramethyl nonanol, derived from propylene tetramer by the oxo synthesis, is the preferred alcohol.  The carboxymethylation may be carried out as described in Specification 669,936; it is preferably carried out to completion in the case of the tri-, tetra- and pentaglycol ethers, to 40-75 per cent completion with the hexa-, hepta- and octa-glycol ethers and to 10-25 per cent completion with the nona- and deca-glycol ethers.  The products are useful as surface-active agents (see Groups Groups III and IV (a)).  In examples: (1) tetramethyl nonanol is reacted with 5 mols. of ethylene oxide, the resulting ether is treated with 1.1 mol. pulverized NaOH and next carboxymethylated with 1 mol. of sodium chloracetate at 40-50 DEG  C. and neutralized with H2SO4; (2) tetramethyl nonanol is reacted with 6 mols. of ethylene oxide and the product is 50 per cent carboxymethylated with 0.5 mol., each of NaOH and sodium chloracetate; the wetting power of the product is compared with those of the 75 and 100 per cent carboxymethylated ethers; (3) tetramethylnonanol is converted into the hepta-, octa-, nona- and deca-glycol ethers respectively and similarly carboxymethylated to the extent of 10-50 per cent; (4) tetramethyl nonanol in excess is reacted with ethylene oxide and the product distilled to remove unchanged alcohol; the residual diglycol ether, containing some mono-, tri- and tetra-glycol ethers, is then completely carboxymethylated. Specification 719,445 also is referred to.ALSO:Water - soluble carboxymethylated glycol ethers of a C13 branched-chain primary alcohol having the general formula R-(O-CH2CH2)n-O-CH2COOM wherein R represents the alkyl radical of the C13 alcohol, n is any integer from 1 to 10 and M is hydrogen or other cation, e.g. sodium, are used alone or with the corresponding un-carboxymethylated glycol ethers as wetting agents in vat-dyeing. The products, the preparation of which is described (see Group IV (b)), are preferably derived from tetramethyl nonanol, obtained by the oxo synthesis from propylene tetramer. Specifications 669,936 and 719,445 are referred to.ALSO:Detergent compositions comprise watersoluble carboxymethylated glycol ethers having the general formula R-(O-CH2CH2)n-O-CH2COOM, wherein R is the alkyl radical of a C13 branched chain primary alcohol, n is an integer from 1 to 10 and M is a cation, e.g. hydrogen or sodium, or a mixture of the carboxymethylated ethers and the corresponding uncarboxymethylated ethers.  The ethers or mixture of ethers may be used in conjunction with other surface-active polyglycol ethers which are soluble or emulsifiable in water such as branched or straight chained primary or secondary decyl-, undecyl-, dodecyl-, tri-decyl-, tetra-decyl- or alkyl phenyl-polyglycol ethers.  The compositions are effective in cotton washing.  Specifications 669,936, [Group IV (b)], and 719,445 are referred to.