Novel benzoxazole compounds

Claim 2

Benzoxazole compounds of the formula ##STR69## wherein R 1 represents hydrogen, halogen, cyano, alkyl of 1 to 8 carbon atoms, cyclohexyl, alkyl of 1 to 4 carbon atoms which is substituted by halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, while the phenyl moiety of a phenylalkyl radical can contain in addition one or two substituents selected from the group consisting of halogen, methyl or methoxy; alkoxy of 1 to 4 carbon atoms which is unsubstituted or substituted by cyano or alkoxy of 1 to 4 carbon atoms; phenyl or phenoxy which is unsubstituted or substituted by one or two radicals selected from the group consisting of halogen, cyano, alkyl or alkoxy, each of 1 to 4 carbon atoms; the sulpho group and the derivatives thereof; the carboxyl group and the derivatives thereof; a sulphonyl group; or together with R 2 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, R 2 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, or together with R 1 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, and A represents a group of the formula ##STR70## wherein R 3 represents a carboxyl group and the derivatives thereof, a sulpho group and the salts thereof, a sulphonyl or cyano group, R 4 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, the sulpho group and the salts thereof or the carboxyl group and the derivatives thereof, R 5 represents hydrogen, alkyl of 1 to 8 carbon atoms, alkyl of 1 to 4 carbon atoms which is substituted by halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, while the phenyl moiety of a phenylalkyl radical can contain in addition one or two substituents selected from the group consisting of halogen, methyl or methoxy; cyclohexyl; alkoxy of 1 to 4 carbon atoms which is unsubstituted or substituted by cyano or alkoxy of 1 to 4 carbon atoms; phenyl or phenoxy which is unsubstituted or substituted by one or two radicals selected from the group consisting of halogen, cyano, alkyl or alkoxy, each of 1 to 4 carbon atoms; halogen, cyano, sulphonyl, the carboxyl group or the derivatives thereof; the sulpho group or the derivatives thereof; or together with R 6 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical; and R 6 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, or together with R 5 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical.

Claim 3

Benzoxazole compounds according to claim 1 of the formula ##STR71## wherein R 1 ' represents hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl containing 1 to 3 carbon atoms in the alkyl moiety, alkoxyalkyl having a total of 2 to 6 carbon atoms, halogen, cyano, benzyl, alkoxy of 1 to 4 carbon atoms, alkoxyalkoxy having a total of 2 to 6 carbon atoms, phenyl, phenoxy, carbalkoxy of 2 to 5 carbon atoms, the carboxyl group and the alkali metal, alkaline earth metal, ammonium and amine salts thereof, or together with R 2 ' in the ortho-position represents the butadienylene radical, R 2 ' represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, alkoxy of 1 to 4 carbon atoms, or together with R 1 ' in the ortho-position represents the butadienylene radical; and A 1 represents a group of the formula ##STR72## wherein R 3 ' represents alkylsulphonyl of 1 to 4 carbon atoms, cyano, a group of the formula --COOY, in which Y represents hydrogen, alkyl of 1 to 4 carbon atoms or an alkali metal, alkaline earth metal, ammonium or amine ion; or represents a group of the formula --SO 3 Y 1 , in which Y 1 represents hydrogen, an alkali metal, alkaline earth metal, ammonium or amine ion, R 4 ' represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, or the sulpho group and the alkali metal salts thereof, R 5 ' represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxyalkyl having a total of 2 to 6 carbon atoms, cyanoalkyl containing 1 to 3 carbon atoms in the alkyl moiety, benzyl, alkoxy of 1 to 4 carbon atoms, alkoxyalkoxy of 2 to 6 carbon atoms, phenyl, phenoxy, halogen, cyano, alkylsulphonyl of 1 to 4 carbon atoms, a group of the formula --COOY, in which Y represents hydrogen, alkyl of 1 to 4 carbon atoms or an alkali metal, alkaline earth metal, ammonium or amine ion; or represents a group of the formula --SO 3 Y 1 , in which Y 1 represents hydrogen, an alkali metal, alkaline earth metal, ammonium or amine ion, a group of the formula ##STR73## in which Z 1 represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxyalkyl having a total of 2 to 6 carbon atoms, cyanoalkyl containing 1 to 3 carbon atoms in the alkyl moiety, Z 2 has the meaning of Z 1 and in addition represents benzyl, or Z 1 or Z 2 together with the nitrogen atom to which they are attached form a morpholine or piperidine ring, or together with R 6 ' in the ortho-position represent the butadienylene radical; and R 6 ' represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, or together with R 5 ' in the ortho-position represents the butadienylene radical,

Claim 4

Benzoxazole compounds according to claim 2 of the formula ##STR74## wherein R 1 " represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, cyano, alkoxy of 1 to 4 carbon atoms, phenyl, the carboxyl group and the alkali metal salts thereof, carbalkoxy of 2 to 5 carbon atoms, or together with R 2 " in the ortho-position represents the butadienylene radical, R 2 " represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, alkoxy of 1 to 4 carbon atoms, or together with R 1 " in the ortho-position represents the butadienylene radical, and A 2 represents a group of the formula ##STR75## wherein R 3 " represents alkylsulphonyl of 1 to 4 carbon atoms, cyano, the carboxyl group and the alkali metal salts thereof, carbalkoxy of 2 to 5 carbon atoms, the sulpho group and the alkali metal salts thereof, R 4 " represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or the sulpho group and the alkali metal salts thereof, R 5 " represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxyalkyl having a total of 2 to 6 carbon atoms, cyanoalkyl containing 1 to 3 carbon atoms in the alkyl moiety, alkoxy of 1 to 4 carbon atoms, phenyl, halogen, cyano, alkylsulphonyl of 1 to 4 carbon atoms, the carboxyl group and the alkali metal salts thereof, carbalkoxy of 2 to 5 carbon atoms, the sulpho group and the alkali metal salts thereof; and R 6 " represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen.

Claim 5

Benzoxazole compounds according to claim 2 of the formula ##STR76## wherein R 1 ' and R 2 ' are as defined in claim 2 and A 1 ' represents a group of the formula ##STR77## wherein R 3 ', R 4 ', R 5 ' and R 6 ' are as defined in claim 2.

Claim 6

Benzoxazole compounds according to claim 3 of the formula ##STR78## wherein R 1 " and R 2 " are as defined in claim 3 and A 2 ' represents a group of the formula ##STR79## wherein R 3 ", R 4 ", R 5 " and R 6 " are as defined in claim 3.

Claim 7

Benzoxazole compounds according to claim 5 of the formula ##STR80## wherein R 1 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, cyano, alkoxy of 1 to 4 carbon atoms, or phenyl, R 2 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, or alkoxy of 1 to 4 carbon atoms, R 3 '" represents alkylsulphonyl of 1 to 4 carbon atoms, cyano, the carboxyl group and the alkali metal salts thereof, carbalkoxy of 2 to 5 carbon atoms, or the sulpho group and the alkali metal salts thereof; and R 4 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or the sulpho group and the alkali metal salts thereof.

Claim 8

Benzoxazole compounds according to claim 6 of the formula ##STR81## wherein R 1 ' v represents hydrogen, chlorine, phenyl, or alkoxy of 1 to 4 carbon atoms, R 3 ' v represents alkylsulphonyl of 1 to 4 carbon atoms, carbalkoxy of 2 to 5 carbon atoms, cyano, or the sulpho group and the alkali metal salts thereof, and R 4 ' v represents hydrogen or the sulpho group and the alkali metal salts thereof.

Claim 9

A benzoxazole compound according to claim 6 of the formula ##STR82##

Claim 10

Benzoxazole compounds according to claim 5 of the formula ##STR83## wherein R 1 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, R 2 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, or alkoxy of 1 to 4 carbon atoms, R 5 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl containing 1 to 3 carbon atoms in the alkyl moiety, alkoxy of 1 to 4 carbon atoms, phenyl, chlorine or cyano; and R 6 '" represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or chlorine.

Claim 11

Benzoxazole compounds according to claim 9 of the formula ##STR84## wherein R 1 ' v represents hydrogen, chlorine, alkoxy of 1 to 4 carbon atoms, or phenyl, R 5 ' v represents hydrogen, chlorine or alkyl of 1 to 4 carbon atoms, and R 6 ' v represents hydrogen or alkyl of 1 to 4 carbon atoms.

Claim 12

Benzoxazole compounds according to claim 3 of the formula ##STR85## wherein R 1 ' v represents hydrogen, chlorine, alkoxy of 1 to 4 carbon atoms or phenyl, and A 3 represents a group of the formula ##STR86## wherein R 5 v represents hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl having a total of 2 or 3 carbon atoms, or phenyl, and R 6 v represents hydrogen or alkyl of 1 to 4 carbon atoms.

Claim 13

A process for the manufacture of benzoxazole compounds of the formula ##STR87## wherein R 1 represents hydrogen, halogen, cyano, alkyl of 1 to 8 carbon atoms, cyclohexyl, alkyl of 1 to 4 carbon atoms which is substituted by halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, while the phenyl moiety of a phenylalkyl radical can contain in addition one or two substituents selected from the group consisting of halogen, methyl or methoxy; alkoxy of 1 to 4 carbon atoms which is unsubstituted or substituted by cyano or alkoxy of 1 to 4 carbon atoms; phenyl or phenoxy which is unsubstituted or substituted by one or two radicals selected from the group consisting of halogen, cyano, alkyl or alkoxy, each of 1 to 4 carbon atoms; the sulpho group and the derivatives thereof; the carboxyl group and the derivatives thereof; a sulphonyl group; or together with R 2 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, R 2 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4carbon atoms, halogen, or together with R 1 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, R 5 represents hydrogen, alkyl of 1 to 8 carbon atoms, alkyl of 1 to 4 carbon atoms which is substituted by halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, while the phenyl moiety of a phenylalkyl radical can contain in addition one or two substituents selected from the group consisting of halogen, methyl or methoxy; cyclohexyl, alkoxy of 1 to 4 carbon atoms which is unsubstituted or substituted by cyano or alkoxy of 1 to 4 carbon atoms; phenyl or phenoxy which is unsubstituted or substituted by one or two radicals selected from the group consisting of halogen, cyano, alkyl or alkoxy, each of 1 to 4 carbon atoms; halogen, cyano, sulphony, the carboxyl group or the derivatives thereof, the sulpho group or the derivatives thereof; or together with R 6 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical; and R 6 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, or together with R 5 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, which process comprises reacting an o-aminophenol of the formula ##STR88## wherein R 5 and R 6 have the given meanings, in an inert high-boiling solvent, with acetic anhydride and an aldehyde of the formula ##STR89## wherein R 1 and R 2 have the given meanings, using a catalyst which splits off water, and without isolation of an intermediate.

Claim 14

A process for the manufacture of benzoxazole compounds of the formula ##STR87## wherein R 1 represents hydrogen, halogen, cyano, alkyl of 1 to 8 carbon atoms, cyclohexyl, alkyl of 1 to 4 carbon atoms which is substituted by halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, while the phenyl moiety of a phenylalkyl radical can contain in addition one or two substituents selected from the group consisting of halogen, methyl or methoxy; alkoxy of 1 to 4 carbon atoms which is unsubstituted or substituted by cyano or alkoxy of 1 to 4 carbon atoms; phenyl or phenoxy which is unsubstituted or substituted by one or two radicals selected from the group consisting of halogen, cyano, alkyl or alkoxy, each of 1 to 4 carbon atoms; the sulpho group and the derivatives thereof; the carboxyl group and the derivatives thereof; a sulphonyl group; or together with R 2 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, R 2 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4carbon atoms, halogen, or together with R 1 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, R 5 represents hydrogen, alkyl of 1 to 8 carbon atoms, alkyl of 1 to 4 carbon atoms which is substituted by halogen, cyano, alkoxy of 1 to 4 carbon atoms or phenyl, while the phenyl moiety of a phenylalkyl radical can contain in addition one or two substituents selected from the group consisting of halogen, methyl or methoxy; cyclohexyl, alkoxy of 1 to 4 carbon atoms which is unsubstituted or substituted by cyano or alkoxy of 1 to 4 carbon atoms; phenyl or phenoxy which is unsubstituted or substituted by one or two radicals selected from the group consisting of halogen, cyano, alkyl or alkoxy, each of 1 to 4 carbon atoms; halogen, cyano, sulphony, the carboxyl group or the derivatives thereof, the sulpho group or the derivatives thereof; or together with R 6 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical; and R 6 represents hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, or together with R 5 in the ortho-position represents an alkylene radical of 3 or 4 carbon atoms or the butadienylene radical, which process comprises reacting an o-aminophenol of the formula ##STR88## wherein R 5 and R 6 have the given meanings, in an inert high-boiling solvent, with acetic anhydride and an aldehyde of the formula ##STR89## wherein R 1 and R 2 have the given meanings, using a catalyst which splits off water, and without isolation of an intermediate.

Claim 15

A process according to claim 12 for the manufacture of benzoxazole compounds of the formula ##STR90## wherein R 1 ' v represents hydrogen, chlorine, alkoxy of 1 to 4 carbon atoms or phenyl, R 5 v represents hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl having a total of 2 or 3 carbon atoms or phenyl, and R 6 v represents hydrogen or alkyl of 1 to 4 carbon atoms, which process comprises reacting an o-aminophenol of the formula ##STR91## in which R 5 v and R 6 v have the given meanings, with acetic anhydride and an aldehyde of the formula ##STR92## in which R 1 ' v has the given meaning.

Claim 16

A process according to claim 12 which is carried out in a high-boiling aromatic hydrocarbon using toluene-4-sulphonic acid as catalyst and the water of reaction is continuously removed.

Claim 17

A method of optically brightening organic material which comprises incorporating in said material or applying to the surface thereof a compound as defined in claim 1.

Claim 18

A method according to claim 15 wherein synthetic organic material of high molecular weight, preferably of polyester and polyamide, is brightened.

Claim 19

A method according to claim 16 wherein the fluorescent brightening agent is incorporated into spinning solutions/melts of polyester or polyamide and these latter are subsequently spun.

Claim 20

A method according to claim 16 wherein polyester or polyamide fabrics are brightened by the pad-heat process.

Claim 21

A method according to claim 15 wherein 0.001 to 2%, preferably 0.01 to 0.5%, of the fluorescent brightening agent, based on the weight of the material to be brightened, is applied to said material or incorporated thereinto.