Patent GB-973113-A (GB)
Title: Improvements relating to bis-triazinylaminostilbene compounds and their use for optically brightening organic materials
IPC: C11D3/42
Filed: 1961-07-27
Abstract: The invention comprises bis-triazinyl aminostilbene compounds of the general formula <FORM:0973113/C1/1> and water-soluble salts thereof, wherein A represents an aromatic radical, Y represents an alkyl or alkoxyalkyl radical in which each alkyl and alkoxy group contains not more than 3 carbon atoms and n is 2 or 3.  They may be prepared by reacting 1 mol. of 4,41-bis(411,611-dihalo-111, 311, 511-triazinyl-211-amino) stilbene-2, 21-disulphonic acid or water-soluble salt thereof with, in any order, 2 moles of a primary aromatic amine A-NH2 and 2 moles of an amine NH2-(CH2)n-O-Y.  The sulphonic acid is preferably used as an aqueous solution of a soluble salt thereof; the first step may be effected at 5 DEG -60 DEG C. and the second at 70 DEG -100 DEG C. The reactions may be effected in the presence of a buffer salt, e.g., an alkali metal salt of either a fatty acid having not more than 4 carbon atoms or carbonic acid.  In typical examples, (1) an aqueous solution of the di-sodium salt of 4,41-diamino-stilbene-2, 21-disulphonic acid and Na2CO3 is added to cyanuric chloride in aqueous acetone yielding a suspension of the di-sodium salt of 4, 41-bis(411, 611-dichloro-111, 311, 511-triazinyl amino) stilbene-2, 21-di-sulphonic acid to which is first added an acetone solution of aniline and Na2CO3 to maintain alkalinity and then 3-methoxypropyl amine and the product is thereafter salted out; (3) 2-methoxy ethylamine and Na2CO3 are added to the di-sodium salt of the bis(dichlorotriazinyl amino) stilbene disulphonic acid of (1) in water followed by the addition of, for example, 1- or 2-amino-naphthalene and NaOH.  Other compounds of the above general formula are prepared wherein A represents phenyl or phenyl substituted by methyl, methoxy, methyl sulphonyl, -COOH, -CONH2, methyl amido-, -SO2NH2, chlorine or bromine and Y-O-(CH2)nis methoxy methyl, methoxy ethyl, ethoxy ethyl, propoxy ethyl, methoxy propyl, ethoxy propyl, 3-(methoxy ethoxy)-propyl, 2-(methoxy ethoxy) ethyl or 2-(ethoxy ethoxy) ethyl.  The aromatic group A may also be fluorine substituted.  The products may be used as optical brightening agents for detergents (see Division C5) and organic fibres (see Division D1).  Amines of the general formula Y-O(CH2)n-NH2 where Y and n are as defined above may be prepared by reacting strong acid (e.g. hydrochloric) esters of the corresponding hydroxy compounds with NH3 under pressure.  3-(methoxy ethoxy) propylamine is obtained by catalytic reduction of the corresponding nitrile.ALSO:Detergent compositions comprise, as a brightening agent, a bis-triazinyl amino stilbene derivative having the general formula <FORM:0973113/C4-C5/1> or a water-soluble salt thereof, where A is an aromatic radical which may bear substituents, Y is an alkyl or alkoxy alkyl radical, the alkyl and alkoxy groups both having not more than 3 carbon atoms, and n is 2 or 3.  Example 7 describes a composition in powder form comprising lauryl sulphate, dodecyl benzene sulphonate, sodium tripolyphosphate, tetrasodium pyrophosphate, sodium sulphate and the sodium salt of 4,41 - bis[411 - (b  - ethoxyethylamino) - 611 - (p - methylphenylamino) - 111,311,511 - triazinyl - (211) - amino] - stilbene - 2,21 - disulphonic acid. Other examples of the above-defined brightening agents are provided.ALSO:Organic fibrous material is optically brightened by treatment with a stilbene derivative having the general formula <FORM:0973113/D1-D2/1> or water-soluble salts thereof, wherein A represents an aromatic radical which may bear, for example, C1-4 alkyl, C1-4 alkoxy, COOH, amido, sulphonamido, alkyl sulphonyl, Cl, Br or F substituents, Y represents an alkyl or alkoxyalkyl group, each alkyl and alkoxy group thereof containing not more than 3 carbon atoms and n is 2 or 3.  They may be used in neutral or alkaline wash liquors for the treatment of cellulose materials.  Example 8 describes the washing of household linen using an aqueous wash comprising the sodium salt of 4,41-bis-[411-(b -ethoxy ethylamino)-611-(p-methyl phenylamino)-111, 311, 511-triazinyl amino]-stilbene-2,21-disulphonic acid, lauryl sulphate, dodecyl benzene sulphonate, sodium tripolyphosphate, sodium pyrophosphate and sodium sulphate. Numerous other stilbene derivatives of the above class are mentioned (see Division C2).