Patent GB-481357-A (GB)
Title: Manufacture of condensation products of capillary activity
IPC: D06M13/402
Filed: 1936-07-09
Abstract: Urethane-like compounds which are stated to have dispersing properties are prepared by causing a chlorcarbonic ester of a carbocyclic hydroxy compound substituted in the nucleus by at least one radicle having at least 4 carbon atoms and consisting of an acyl radicle or a hydrocarbon radicle other than an aryl radicle, or of a hydroxyalkylether, a polyhydroxyalkylether or a polyglycol ether of such a carbocyclic hydroxy compound to react with a compound containing a primary or secondary amino group and also a group imparting solubility in water.  Solubility may also be effected by (a) treating the products with a sulphonating agent when they contain an alcoholic hydroxy group or an aromatic ring, (b) treating with an alkylating agent when they contain a basic nitrogen atom, or (c) treating with an alkylene oxide, halogenhydrin or an organic compound containing a carboxylic or sulphonic group and an atom or group capable of reacting with an amino or hydroxy group when the products contain such a group. The products may be used in association with soap, alcoholsulphonates, alkylated benzene or naphthalene sulphonic acids, soluble cellulose derivatives, alcohols, amines, phenols, alkyl phenols and hydrogenation products which have been treated with ethylene oxide, sodium carbonate, phosphates and perborates. In examples: (1) methyl taurine is treated with the chlorcarbonic esters of dodecylphenol, octylcyclohexanol, tetradecylnaphthylpentaglycolether, octylphenyldiglycolether and cyclohexylphenylmonoglycolether; (2) sarcosine is treated with the chlorcarbonic esters of dodecylphenol, octylphenyltriglycolether, dodecylphenyldodecaglycolether, octylcyclohexyltriglycolether, lauroylphenyltriglycolether and octylphenyltripropyleneglycolether; (3) methylglucamine is condensed with the chlorcarbonic ester of hexylphenylglycol ether; (4) ethylenediamine is condensed with the chlorcarbonic ester of octylphenylmonoglycol ether and the product sulphonated; (5) aminoethanol is condensed with the chlorcarbonic ester of octylphenylmonoglycolether and the product sulphonated; (6) sodium sulphanilate is condensed with the chlorcarbonic ester of octylphenyl; (7) sodium cyclohexyltauride is condensed with dodecylcyclohexanolchlorcarbonic ester; (8) the chlorcarbonic ester of octylphenylmonoglycol ether is condensed with dodecylamine in pyridine; (9) the chlorcarbonic ester of octylphenyltriglycolether is condensed with cyclohexylethanolamine in pyridine.  Ethanolamine sulphuric esters, aminoacetic acid, anthranilic acid and albumin decomposition products are mentioned as amino compounds containing water solubilising groups.  Samples have been furnished under Sect. 2 (5) of products prepared as follows: (1) by condensing sodium methyltaurine with dodecylphenolchlorcarbonicester, octylcyclohexanolchlorcarbonicester, the chlorcarbonicester of lauroylphenylpentaglycolether and the chlorcarbonicester of octylphenyltriglycolether; (2) sodium sarcosine is condensed with butylphenolchlorcarbonicester, caproylphenolchlorcarbonicester, the chlorcarbonicester of lauroylphenylpentaglycolether and the chlorcarbonicester of octylphenyltriglycolether; (3) caproylphenolchlorcarbonicester is condensed with piperidine sulphonicacid; (4) ethanolamine is condensed with octylphenolchlorcarbonicester and then solubilized with diglycollicanhydride and also condensed with butylphenolchlorcarbonicester and then solubilized with ethyleneoxide; (5) N-methylglucamine is condensed with the chlorcarbonicester of octylphenyldecaglycolether; (6) chlorcarbonicesters of technical iso-alkylphenylpentaglycolethers, in which the alkyl radicles contain 12-14 carbon atoms and are derived from polymerized olefines are condensed with N-dimethylpropylenediamine and then solubilized by treating with dimethylsulphate and also condensed with aniline and solubilized by sulphonation.ALSO:Urethane-like compounds are prepared by causing a chlorcarbonicester of a carbocyclic hydroxy compound substituted in the nucleus by at least one radicle having at least 4 carbon atoms and consisting of an acyl radicle or hydrocarbon radicle other than an aryl radicle, or of a hydroxy alkylether, a polyhydroxyalkylether or a polyglycolether of such a carbocyclic hydroxy compound to react with a compound containing a primary or secondary amino group and possibly also a group imparting solubility in water.  Solubility may also be effected by (a) treating the products with a sulphonating agent when they contain an alcoholic hydroxy group or an aromatic ring, (b) treating with an alkylating agent when they contain a basic nitrogen atom, or (c) treating with an alkylene oxide, halogenhydrin or an organic compound containing a carboxylic or sulphonic group and an atom or group capable of reacting with an amino or hydroxy group when the products contain such a group.  The soluble products or their salts are stated to have wetting, foaming, washing and dispersing properties.  They may be used in association with soap, alcoholsulphonates, alkylated benzene or naphthalene sulphonic acids, soluble cellulose derivatives, alcohols, amines, phenols, alkyl phenols and hydrogenation products which have been treated with ethylene oxide, sodium carbonate, phosphates and perborates. In examples: (1) methyltaurine is treated with the chlorcarbonicesters of dodecylphenol, octylcyclohexanol, tetradecylnaphthylpentaglycolether, octylphenyldiglycolether and cyclohexylphenylmonoglycolether; (2) sarcosine is treated with the chlorcarbonicesters of dodecylphenol, octylphenyltriglycolether, dodecylphenyl, dodecaglycolether, octylcyclohexyltriglycolether, lauroylphenyltriglycolether and octylphenyltripropyleneglycolether; (3) methylglucamine is condensed with the chlorcarbonicester of octylphenylmonoglycol ether and the product sulphonated; (5) aminoethanol is condensed with the chlorcarbonicester of octyl phenylmonoglycolether and the product sulphonated; (6) sodium sulphanilate is condensed with the chlorcarbonicester of octylphenol; (7) sodium cyclohexyltauride is condensed with dodecylcyclohexanolchlorcarbonicester; (8) the chlorcarbonicester of octylphenylmonoglycol ether is condensed with dodecylamine in pyridine; (9) the chlorcarbonicester of octylphenyltriglycolether is condensed with cyclohexylethanolamine in pyridine.  The ethers used as raw material may be prepared according to the process described in Specification 470,181.  Ethanolaminesulphuricesters, aminoaceticacid, anthranilic acid and albumindecomposition products are mentioned as examples of amino compounds containing water-solubilizing groups. Samples have been furnished under Sect. 2 (5) of products prepared as follows: (1) by condensing sodium methyl taurine with dodecylphenolchlorcarbonicester, octylcyclohexanol chlorcarbonicester, caproylphenolchlorcarbonicester, the chlorcarbonicester of lauroylphenylpentaglycolether and with the chlorcarbonicester of octylphenyltriglycolether; some of the products are purified by extracting with ether and acetone; (2) sodium sarcosine is condensed with butylphenolchlorcarbonicester, caproylphenolchlorcarbonicester, the chlorcarbonicester of lauroylphenylpentaglycolether, and the chlorcarbonicester of octylphenyltriglycol ether; (3) caproylphenolchlorcarbonicester is condensed with piperidine sulphonic acid; (4) ethanolamine is condensed with octylphenolchlorcarbonicester and then solubilized with diglycollic anhydride and also condensed with butylphenolchlorcarbonicester and then solubilized with ethyleneoxide; (5) N-methylglucamine is condensed with the chlorcarbonicester of octylphenyldecaglycolether; (6) chlorcarbonicesters of technical isoalkylphenyl pentaglycolethers, in which the alkylradicles contain 12-14 carbon atoms and are derived from polymerized olefines are condensed with N-dimethylpropylenediamine and then solubilized by treating with dimethylsulphate and also condensed with aniline and solubilized by sulphonation.