Patent GB-980092-A (GB)
Title: ª-cyano-2-alkenoxy-1-naphthalene acrylic acid ester compounds and methods for making same
IPC: D06M13/13
Filed: 1961-03-06
Abstract: The invention comprises compounds of the formula <FORM:0980092/C2/1> wherein R1 represents an alkenyl radical containing 3-20 carbon atoms, n is 1 or 2 and, when n is 1, R2 represents an alkyl, alkenyl, hydroxyalkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, hydroxyalkoxyalkyl, hydroxypolyalkoxyalkyl, or carboxyalkyl radical, or an aryl or heterocyclic radical which may be substituted e.g. by an alkyl, alkoxy, halo, hydroxyalkyl, carboxy, carboalkoxy, acyl or acylamino radical; and when n is 2, R2 represents an alkylene, arylene or divalent heterocyclic radical which may be substituted.  The compounds may be prepared by reacting a 2-alkenyloxy-1-naphthaldehyde with a cyanoacetic acid ester of the formula (CNCH2COO)nR2 in the presence of a secondary amine such as piperidine.  Extensive lists of values for R1 and R2 are given.  Compounds containing active hydrogen atoms, particularly hydroxy groups, may subsequently be reacted with an alkylene oxide to give a product containing 1-100 oxyalkyl groups. In examples compounds are prepared in which R1 represents allyl, methallyl, crotyl and decenyl and R2 represents methyl, ethyl, tetrahydrofurfuryl, glyceryl, hydroxyethyl, chloroethyl, bromoethyl, cyanoethyl, methoxyethyl, hydroxyethoxyethyl, carbomethoxyethoxyethyl, phenyl, p-chlorophenyl, p-methoxyphenyl, p-acetylaminophenyl, b -naphthyl, benzyl, ethylene, 1-phenyl-2,3-propylene and p-xylylene. Certain of the products are subsequently condensed with ethylene and/or propylene oxide. The compounds find application as U.V. absorbers.  2 - Allyloxy - 1 - naphthaldehyde is prepared by reacting 2-hydroxy-1-naphthaldehyde with allyl bromide.  a  - Cyano - tetrahydrofurfuryl acetate is prepared by esterification of acid and alcohol in the presence of an alkane sulphonic acid.  Cyanoacetic acid mono-glyceryl ester is prepared by esterifying the acid with glycerol in the presence of p-toluene sulphonic acid.ALSO:Synthetic polymers and films, sheets, and other articles made thereof are protected from deterioration by U.V. rays by incorporating in them a small proportion, e.g. 0.1-10% of an a -cyano-b -alkenyloxy-naphthyl-acrylate of the general formula <FORM:0980092/C3/1> wherein R1 is an alkenyl radical of 3-20 carbon atoms, n is 1 or 2 and, when n is 1, R2 is alkyl, alkenyl, hydroxyalkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, hydroxalkoxyalkyl, hydroxypolyalkoxyalkyl, or carboxyalkyl, or an aryl, or heterocyclic radical which may be substituted, e.g. by alkyl, alkoxy, halogen, hydroxalkyl, carboxy, carbalkoxy, acyl, or acylamino; and, when n is 2, R2 represents an alkylene, arylene, or a divalent heterocyclic radical.  Compounds of the stated formula containing active hydrogen atoms, particularly hydroxy groups may be reacted with an alkylene oxide to give products containing up to 100 oxyalkyl groups. In examples a compound of the stated formula in which R1 is - CH2 - CH=CH2, R2 is - CH2CH2OH and n is one, is poly-oxyalkylated with ethylene oxide in presence of potassium hydroxide to yield a product containing 35 oxyethyl groups, and with propylene oxide and subsequently with ethylene oxide to obtain a product containing 10 oxypropyl and 10 oxethyl groups. The compounds of the stated formula may be incorporated in high molecular weight polymers of formaldehyde to impart stability to U.V. rays as evidenced by resistance to the formation of surface cracks and crazing.  The compounds may be incorporated in the finished polymer but preferably in the polymerizing mass.ALSO:Alpha - cyano - beta - (2 - alkenyloxy - 1 - naphthyl) -acrylic esters, in which the alkenyl group has 3-20 carbon atoms (see Division C2), are incorporated as U.V. ray absorbers in paints, varnishes, lacquers, enamels and waxes which are thus protected from deterioration. This protection extends to the dried paint and other film coatings which are given resistance to cracking, loss of elasticity, fading, and change of colour.  The proportion of protective agent incorporated may be 0.1-10% based on the solids content of the organic material.ALSO:Alpha - cyano - beta - (2 - alkenyloxy - 1 - naphthyl)-acrylic esters, in which the alkenyl group has 3-20 carbon atoms (see Division C2), are incorporated as U.V. ray absorbers in creams, lotions, or other preparations to be used for protecting the skin from sunburn or sun tan.ALSO:The adhesive composition of a pressure-sensitive tape is protected against the degradative effects of exposure to ultra-violet light by incorporating in the transparent plastic backing material a small proportion, e.g. 0,1-10% of an alpha-cyano-beta-(2-alkenyloxy-1-naphthyl)-acrylic ester, in which the alkenyl group has 3-20 carbon atoms (see Division C2).  The protective substance may be incorporated in the plastic backing material in the manufacture thereof, or may be impregnated or coated thereon or therein.  The backing material is also protected from degradation.ALSO:Alpha-cyano-beta-(2-alkenyloxy-1-naphthyl) -acrylic esters, in which the alkenyl group has 3-20 carbon atoms (see Division C2), are incorporated as U-V ray absorbers in translucent fibrous materials such as textiles and paper to protect these materials from deterioration.  Coloured materials such as dyed textiles are also rendered resistant to fading on exposure to sunlight.