Patent GB-924762-A (GB)
Title: New derivatives of 1,4-bis-styryl-benzene and optical brightening therewith
Inventor: STILZ WALTER
IPC: C11D1/00
Filed: 1960-05-13
Abstract: Substituted 1,4-bis-styryl benzenes of the general formula: <FORM:0924762/IV(a)/1> in which X and X1 stand for carboxylic ester groups or N-alkyl carboxylic amide groups, are prepared by reacting terephthaladehyde with an ester of a carbalkoxy-benzylphosphonic acid or with an ester of a halogenmethylbenzoic acid, with the aid of a triarylphosphine and an alkali alcoholate, and if necessary converting the ester groups of the products into amide groups.  These substituted 1,4-bis-styryl benzenes are optical brightening agents (Group IV(c)).  In Example 1, the methyl ester of p-chlormethylbenzoic acid is stirred with triphenylphosphine in dimethylformamide at 80 DEG C. for 3 hours; and then terephthalaldehyde followed by sodium methylate are added.  The product is 1,4-bis-(para-carbmethoxy-styryl)-benzene, and this is converted, by heating it with diethanolamine, into 1,4-bis-(para-carbodiethanolamidostyryl)-benzene <FORM:0924762/IV(a)/2> Example 8 refers to 1,4-bis-(meta-carbdiethanolamido-styryl)-benzene.  Example 9 describes the preparation of a mixture of 1,4-bis-(para-carbethoxy-styryl) - benzene, 1,4 - bis - (metacarbmethoxy-styryl)-benzene and 1-(para-carbmethoxy-styryl) - 4-(meta1-carbmethoxy-styryl)-benzene, by reacting terephthalaldehyde with a mixture of meta- and para-carbmethoxy-benzyl-phosphonic acid diethyl ester.  The mixture of 1,4-bis-styryl-benzene diesters is then reacted with diethanolamine.  Example 19 states that 1,4-bis-(meta-carb-N-cyclohexylisopropanol-amidostyryl)-benzene is obtained by reacting 1,4 - bis - (meta-carbmethoxy-styryl)-benzene with N-cyclohexyl-iso-propanolamine.  It is stated that X and X1 in the general formula may stand for COO.C2H4OH, and similar groups. Compounds wherein the hydrogen atoms of the hydroxy groups in both the amides and the esters are substituted by glycol ether groups are obtained by the reaction of the amides or esters with ethylene oxide or propylene oxide.  Specification 813,539 is referred to.ALSO:Substituted 1, 4-bis-styryl benzenes of the general formula <FORM:0924762/IV(a)/1> in which X and X1 stand for carboxylic ester groups or N-alkyl carboxylic amide groups, act as brightening agents for textiles, paper and leather.  The brightening agent is preferably used in aqueous medium in amounts of about 0,0015 to 0.05% with reference to the weight of the substrate to be brightened.  In Example 1, previously bleached cotton fabric is treated, for 20 minutes, in a liquor, at 50 DEG  to 60 DEG C., containing 0,003 to 0,01 grams per litre of the compound having the structure <FORM:0924762/IV(a)/2> and 5 grams per litre of sodium sulphate decahydrate, the liquor to fabric ratio being 50:1.  After rinsing and drying, the fabric has a dazzling whiteness of good fastness to light and washing. Examples 5, 6 and 7 relate to the use of the same compound for brightening polycaprolactam fabric, yellowish paper, and soiled clothing, respectively.  Example 8 describes the use of 1, 4-bis-(metacarbdiethanolamidostyryl)-benzene for brightening cotton fabric.  For the preparation of the brightening agents, (see Group IV(b)).  Specification 813,539 is referred to.