SE181818C1 - - Google Patents

Description

Inventor: M Dunnenberger and AE Siegrist Priority begra frail March 11, 1960 (Switzerland) It has been shown that the optical whiteness of organic materials, especially polyester materials, can be Moja by a cc, i3-di- [benzoxazo1y1- (2 Ethylene of the formula C-CH = CI-I-C (1) van denotes a phenyl or cyclohexyl residue, is incorporated into the organic materials or added to the preparation mixtures for them or applied to them. The residue R in the formula (1) thus has the composition C6H6n.-1. wherein n represents 1 or 2.

The novel compounds of formula (1), which are apparently used according to the Lipp invention, can be prepared according to processes which are known for the preparation of other α, 16-di- [benzoxazolyl- (2) j-ethylenes, for example according to what is described below. the manufacturing process. 3-Amino-4-oxy-1,1'-diphenyl or 1-oxy-2-amino-4-cyclohexylbenzene is condensed at elevated temperature in a molecular ratio of 2: 1 with fumaric acid, aspartic acid or preferably malic acid or functional derivatives, e.g. ex. dialkyl esters, of these acids and thereafter the precipitation of the dibenzoxazolyl compound is effected without the precipitation of intermediates by means of catalysts and, if malic acid or aspartic acid is used as starting materials, the cleavage of water and ammonia from the residues of these acids, respectively. Boric acid was suitably used as the catalyst and the reaction is preferably carried out in an organic solvent such as xylene.

The novel α4-di- [benzoxazolyl- (2)] -ethylene compounds of formula (1), which are to be used according to the invention, are suitable for optical whiteness enhancement of the most diverse organic materials. Good results are obtained, for example, in the increase in whiteness of lacquers, such as alkyd resin lacquers or nitrocellulose ester lacquers. These compounds can also be used elsewhere to increase the whiteness of films. They are furthermore suitable for increasing the whiteness of synthetic fibers, e.g. fibers of cellulose esters, such as acetate silk, polyacrylonitrile, polyamide or polyvinyl chloride. However, they have been found to be particularly valuable for increasing the whiteness of polyester fibers, especially fibers of terephthalic acid polyglycol esters. On these fibers they are preferably used in the form of a fine dispersion in water. Sada = dispersions can be prepared on and off If the edge is in high concentration with kanda dispersants, e.g. polyglycol ethers in high molecular weight alcohols or o-alkylphenols, and are optionally diluted with water for use. Especially on the polyester fibers, a much more light-resistant, whitening-enhancing effect is obtained with the new whitening-enhancing agents. In comparison with the known compound α4-di- [5-methylbenz-oxazolyl- (2)] -ethylene, the bhda according to the invention distinguish any other new compounds of formula (1) in that they show as optical brighteners for polyester fibers a significantly stronger effect.

In the following example, parts, unless otherwise indicated, denote parts by weight and percent by weight. The temperatures are given in degrees Celsius.

Example. A fine dispersed paste is prepared from 12 parts of one of the hada described in the following compounds A and B, 12 parts of a storage product of about 30 moles of ethylene oxide in a mixture of saturated fatty alcohols having an average of over 18 carbon atoms and 76 parts of water. Polyester fibers, e.g. dakron, which is treated with 0.2% of one of these pastes for 30 minutes at 60 to 1000 in a bath ratio of 1:30 in a bath containing 1 ml of ammonia per liter, and then rinsed and dried, having a lighter appearance on the untreated material.

Compound A can be prepared as follows: 18.5 parts of 3-amino-4-oxy-1,1'-diphenyl, 6.7 parts of malic acid and 0.3 parts of boric acid are stirred with 300 2 parts of xylene for 6 hours in a stream of nitrogen gas. in coclates the mixture cools, at which temperature the water formed is deposited benzoxazolyl- (2) The fat of the formula continuously with a water trap. Man •> ../ N \ \ C — CH = CH — C are separated in the form of yellow crystals.

Replacement: approximately 19 parts.

A preparation which has been recrystallized three times from dimethylformamide, slurries at 256.8 to 257.4 ° and shows the following analytical value C221-11202N 2 calculated value: C 81.14 H 4.38 N 6.76 found value: C 80, 71 H 4.28 N 6.71.

H2C-H, C HC - / / / IC-CH = H2C — H2C N / \ 0 / If instead of 1-oxy-2-amino-4,5-dimethylbenzene 19.1 parts of 1-oxy-benzene are used 2-amino-4-cyclohexylbenzene, there is obtained α, β-di45-cyclohexylbenzoxazolyl- (2) Feten (= compound B) of the formula N 2 "\\ / —C.f 4 CH 2 CH 2 -Cl O / \ / with the same purity and in approximately the same yield The preparation drops at 205.4 to 206 ° and shows the following analytical value: C221-12202N2 calculated value: C 79.21 H 6.65 N 6.60 fauna value: C 79 45 H 6.86 N 6.48, wherein a, 13-di- [benzoxazolyl- (2) 1-ethylene compounds of the formula N / N 2 (\ - RC-CH = CH-Cl

Claims (1)

Patent claim: Intended to increase the optical whiteness of organic materials, in particular polyester materials, can characterize in which R represents a phenyl or cyclohexyl group, is incorporated into the organic materials or added to the preparation mixtures for them or fixed thereon. Request publications: Stockholm 1962. Kungl. Boktr. P. A. Norstedt J Muer. 620089