Patent GB-1012312-A (GB)
Title: Improvements in or relating to amphoteric phenolic compounds
IPC: A01N57/22
Filed: 1961-11-08
Abstract: Detergent compositions comprise an amphoteric phenolic compound of one of the formulae <FORM:1012312/C4-C5/1> <FORM:1012312/C4-C5/2> <FORM:1012312/C4-C5/3> wherein A represents a mono or polycyclic aromatic hydrocarbon; R is hydrogen or an alkyl, aryl or polycyclic radical, halogen, nitro, amino or diazonium; x is an integer of 1 to 5; R5 and R6 are hydrogen or non-aromatic (i.e. the nitrogen is not joined directly to aromatic) radicals or form together a divalent aliphatic group which with the nitrogen atom forms a heterocyclic ring; M is hydrogen, an alkali metal, ammonium or amine salt-forming group; R1 is a non-aromatic hydrocarbon radical containing less than 10 carbon atoms; n is an integer in the range 1-10 and m is 0 or an integer of 1-9; provided that in formula I, a and b are each 1 or 2; in formula II, b is 1, 2, or 3 and a is 0, 1 or 2; in formula III, b is 1 or 2 and a is 0, 1 or 2; in water with the optional presence of quaternary ammonium germicides, phenolic germicides or organo-metallic germicides. Examples describe compositions in which several of the following are present : ethylene diamine tetraacetate acid and its sodium salt, potassium pyrophosphate, trisodium phosphate, cocobenzyl - dimethyl ammonium chloride, potassium hydroxide, o-benzyl-p-chlorophenol, isopropanol, an organo-tin germicide, pine oil, phosphoric acid, sulphuric acid, sodium bisulphite or sulphite, an alkyl aryl sodium sulphonate detergent, and sodium xylene sulphonate.  Azo dyes are made in examples by coupling the sodium salt of 2-(N-sulphoethyl-N-methylamino - methyl) - 4 - nonylphenol with diazotized sulphanilic acid or benzene diazonium chloride in caustic soda.ALSO:The invention comprises compounds having the general formula <FORM:1012312/C2/1> <FORM:1012312/C2/2> <FORM:1012312/C2/3> wherein A represents a mono- or polycyclic aromatic hydrocarbon group; R is hydrogen or an alkyl, aryl or polycyclic radical, halogen, nitro, amine or diazonium; #c is an integer less than 6; R5 and R6 and hydrogen or non-aromatic radicals or form together a divalent aliphatic group which with the nitrogen atom forms a heterocyclic ring; M is hydrogen, an alkali metal, ammonium or amine salt-forming group; R1 is a non-aromatic hydrocarbon structure containing less than 10 carbon atoms; n is an integer in the range 1-10 and m is 0 or an integer of 1-9. In Formula (I), a and b are each 1 or 2; in Formula (II) b is 1, 2 or 3 and a is 0, 1 or 2, b being no more than 2 when a is 1 or 2; in Formula (III), b is 1 or 2, and a is 0, 1 or 2.  The expression "non-aromatic" means that the radicals are not directly linked to the nitrogen by an aromatic nucleus.  The sulphonic, carboxylic and phosphonic acid radicals may also be replaced by the corresponding ester or amide radicals.  The compounds in which a is 0 may be prepared by the condensation of phenols, having at least one free nuclear position ortho or para to the phenolic hydrogen group, with formaldehyde and secondary non-aromatic amino sulphonic, carboxylic or phosphonic acids.  The compounds in which a is 1 or 2 are made by reacting phenols having at least two free nuclear positions ortho and para, or both ortho, to the phenolic hydroxyl group, with formaldehyde, a non-aromatic secondary amino acid, or a salt thereof, and a primary or secondary non-aromatic amine, such as mono- or di-methyl-, ethyl, propyl or isopropyl amine or diethanolamine. The addition of an alcohol, glycol, fatty acid, aromatic acid, sodium xylene sulphonate, soap, wetting agent or emulsifier may be necessary to make the reaction proceed. If compounds of Formula (II) in which a is 0 and b is 1 are reacted with formaldehyde, the product obtained has the following formula <FORM:1012312/C2/4> The products of the invention react further with formaldehyde and mercaptans.  Detailed examples are given of the preparation of products falling into the above general formulae and further products of the formulae <FORM:1012312/C2/5>ALSO:Germicidal compositions comprise a compound of one of the formul  <FORM:1012312/A5-A6/1> <FORM:1012312/A5-A6/2> <FORM:1012312/A5-A6/3> wherein A represents a mono- or polycyclic aromatic hydrocarbon; R is hydrogen or an alkyl, aryl or polycyclic radical, halogen, nitro, amino, or diazonium; x is an integer less than 6; R5 and R6 are hydrogen or nonaromatic radicals (i.e. the nitrogen is not joined directly to aromatic radicals) or form together a divalent aliphatic group which with the nitrogen atom forms a heterocyclic ring; M is hydrogen, an alkali metal, ammonium, or amine salt-forming group; R1 is a non-aromatic hydrocarbon radical containing less than 10 carbon atoms; n is an integer in the range 1-10 and m is o or an integer of 1-9; provided that in formula I, a and b are each 1 or 2; in formula II, b is 1, 2 or 3 and a is 0, 1 or 2; in formula III, b is 1 or 2 and a is 0, 1, 2; together with a quaternary ammonium germicide or phenolic germicide.  Examples illustrate compositions comprising a compound of formula II (obtained from sodium N-methyl taurate, p-nonyl phenool, formaldehyde and dimethyl amine) together with germicides such as cocobenzyldimethyl ammonium chloride, o-benzyl-p-chlorophenol, an organotin germicide, alkyl aryl sulphonate detergents and other components including tetrapotassium pyrophosphate, ethylene diamine tetraacetic acid, potassium hydroxide, isopropanol, pine oil, phosphoric acid and sodium xylene sulphonate.