Eastman-Kodak Company

Ralph R Giles

Max Allen Weaver

Thomas G Davis

Disclosed are azo dyes in which the diazo component is a diazotized 3-amino-2,1-benzisothiazole compound bearing one or two sulfo groups, and the coupler is either a 1,2,3,4-tetrahydroquinoline or a 2,3-dihydro-1,4-benzoxazine compound. These dyes exhibit excellent dyeing and fastness properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the general formula: ##STR1## wherein R.sup.5 is 0-3 substituents independently selected from halogen, cyano, alkyl, alkoxy, sulfo, and the like; M is H.sup.+, Na.sup.+, K.sup.+ or the like; and C is the coupler which may be substituted with groups known to the art.

Azo dyes from sulfonated 3-sulfonated 3-amino-2,1-benzisothiazoles with

Disclosed are colored polyesters having copolymerized therein anthraquinone derivative colorants containing one or more sulfonamido groups. The colored polymers are fast to light and the colorant moieties are not extractable therefrom, rendering from the colored polymers particularly suitable for use in food containers such as molded beverage bottles. The inherent viscosities of these polymers can be varied widely as is well known in the art for different applications. The copolymerizable colorants have the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or 1-3 substituents independently selected from alkyl, alkoxy, and the like; and T represents 1-4 independently selected radicals of the formula ##STR2## wherein R.sub.3 is hydrogen or 1-3 substituents such as alkyl, alkoxy and the like; Z is a divalent linking group such as --NH--, --S--, --O--, and alkoxycarbonyl; and Q is hydroxy, carboxy or alkoxycarbonyl.

Polyesters containing copolymerized, anthraquinone colorant compounds

Disclosed are tris phenyl bisazo dyes bearing one or two sulfated alkoxycarbonyl or sulfated alkylcarbamyl groups. These dyes impart yellow to red shades to fibers, particularly polyamides, and are especially useful for dyeing polyamide (nylon) carpets, generally giving good fastness to light, ozone, oxides of nitrogen, washing, sublimation, crocking, and the like, and having good leveling, exhaustion, build properties, and stability to variations in dyeing condition such as pH and temperature. The present dyes have the general formula: ##STR1## wherein X is --O--, --NH--, --N(alkyl)--, or --N(aryl)--; Z is selected from straight or branched-chain alkylene, and such alkylene containing one or two internal linkages independently selected from ether, amine and amide; M is H, Na, K, or NH.sub.4 ; n is 1 or 2; R.sub.3 is --OH, alkoxy or --NR.sub.8 R.sub.9, wherein R.sub.8 and R.sub.9 are independently selected from H and alkyl and when either R.sub.4 or R.sub.5 is hydroxy or alkoxy ortho to the azo radical, R.sub.3 is further selected from hydrogen, halogen, alkyl, aryl and acylamido; and R, R.sub.1, R.sub.2, R.sub.4, and R.sub.5 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, alkoxy, and acylamido, with the proviso that when R.sub.3 is neither --OH, alkoxy, nor --NR.sub.8 R.sub.9, one of R.sub.4 and R.sub.5 is either hydroxy or alkoxy ortho to the azo radical. These alkyl, alkylene, alkoxy and aryl moieties may be substituted with a wide variety of substituents known to the art.

Water-soluble tris phenyl bisazo dyes for polyamide fibers

Disclosed are novel dyes which comprise aniline diazo moieties and certain aromatic amine couplers having sulfate groups. These dyes are substantially water soluble and are particularly useful for dyeing polyamide, wool and the like and exhibit, for example, excellent dyeability properties and fastness to light and gas. The dyes correspond to the general formula: ##STR1## wherein ring A may be unsubstituted or substituted with 1-3 of a variety of groups which themselves may be substituted such as alkyl, alkoxy, chloro, bromo, iodo, trifluoromethyl, thiocyano, cyano, phenylazo, acyl, and the like; R.sub.1 is a group such as alkyl, alkoxy, halogen, acylamido, alkylthio, and aryloxy; m is 0, 1, or 2; R.sub.2 represents the linking groups necessary to form a 1,2,3,4-tetrahydroquinoline or a 2,3-dihydro-1,4-benzoxazine structure, which may be substituted, in combination with the phenylene ring; Z is a linking group such as alkylene; and M is H.sup.+, Na.sup.+, K.sup.+, or NH.sub.4.sup.+.

Aniline azo dyes from 1,2,3,4-tetrahydroquinoline and

This invention relates to azo dyes in which the diazotized amino component bears sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the general formulae: ##STR1## wherein X' is O, NH, N(alkyl)-- or N(aryl)--; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy, aryloxy and the like; M is H, Na, K or NH.sub.4 ; and the coupler C is selected from those of the formulae ##STR2## wherein the R substituents are selected from a wide variety of groups known to the art.

Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties

This invention relates to azo dyes particularly useful for dyeing polyamide fiber, wool and the like, in which the diazotized amino component bears sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the formula: ##STR1## wherein R.sup.1 and R represent a large variety of groups; X' is O, NH, N(alkyl)- or N(aryl)-; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy, aryloxy and the like; M is H, Na, K or NH.sub.4 ; n is 1 or 2; and the coupler C is selected from a variety of couplers including anilines, tetrahydroquinolines, phenols and the like.

Azo dyes with sulfate groups on the diazotized 2-amino thiazol and

This invention relates to azo dyes in which the diazotized 2-aminothiophene bears 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing and fastness properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the general formula: ##STR1## wherein R.sup.1 is selected from hydrogen, alkyl, aryl, alkoxy, thiocyano, formyl, alkylthio, carbamoyl, alkoxycarbonyl, alkylcarbamoyl, acyl, aroyl, arylsulfonyl, alkylsulfonyl, sulfamoyl, SO.sub.2 NH(alkyl), SO.sub.2 N(dialkyl),alkylsulfonamido, acylamido, halogen, trifluoromethyl, SO.sub.3 (aryl) and arylazo; X' is O, NH, N(alkyl)-- or N(aryl)--; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy, aryloxy and the like; M is H, Na, K or NH.sub.4 ; n is 1 or 2; and the coupler C is selected from a variety of couplers including anilines, tetrahydroquinolines, phenols and the like.

Azo dyes from a 2-aminothiophene having 1 or 2 sulfated

This invention relates to azo dyes in which the diazotized amino component bears 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the formula: ##STR1## wherein when n is 1, R.sup.1 is selected from hydrogen, alkyl, aryl, alkylthio, carbamoyl, alkylcarbamoyl, acyl, cyanoalkyl, and halogen; R is selected from hydrogen, alkyl, aryl, acyl, alkylsulfonyl, arylsulfonyl alkylsulfamoyl, arylsulfamoyl, alkyl substituted with alkoxy, cyano, or halogen, and aryl substituted with alkoxy, halogen, or cyano; X' is O, NH, N(alkyl)--or N(aryl)--; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy, aryloxy and the like; M is H, Na, K or NH.sub.4 ; n is 1 or 2; and the coupler C is selected from a variety of couplers including anilines, tetrahydroquinolines, phenols and the like.

Azo dyes from a 5-aminopyrazole bearing 1 to 2 sulfated

This invention relates to azo dyes in which the diazotized amino component bears 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing and fastness properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the general formula: ##STR1## wherein R.sup.1 represents up to three of a large variety of groups such as alkyl, alkoxy, acyl, arylthio, and the like; X' is O, NH, N(alkyl)- or N(aryl)-; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy, aryloxy and the like; M is H, Na, K or NH.sub.4 ; n is 1 or 2; and the coupler C is selected from a variety of couplers including anilines, tetrahydroquinolines, phenols and the like.

Azo dyes from aniline having 1 or 2 sulfated hydroxyalkoxycarbonyl or

Disclosed are new azo dyes prepared by diazotizing selected substituted anilines and coupling with aniline couplers containing sulfate ester groups. These dyes impart fast yellow to reddish-orange shades on polyamide fibers and also color cellulose acetate and wool. The dyes have the following general formula: ##STR1## wherein R is selected from a variety of groups such as alkyl, alkoxy, aryl, cycloalkyl, aryloxy, NH.sub.2, and NH alkyl; X is hydrogen, halogen, alkyl, or the like; Y is hydrogen or halogen; R.sub.1 is selected from groups such as hydrogen, alkyl, alkoxy, halogen, acylamido, alkylthio, and aryloxy; R.sub.2 is selected from such groups as hydrogen, alkyl, aryl and cycloalkyl; Z is a linking group such as alkylene; M is H.sup.+, Na.sup.+, K.sup.+, or NH.sub.4.sup.+ ; and m is 0, 1, or 2.

Dyes from selected substituted aniline diazo components and aniline

Disclosed are azo dyes prepared by diazotizing heterocyclic amines such as 2-aminobenzothiazole, 3-amino-2,1-benzisothiazole, 5-amino-1,2,4-thiadiazole, 5-aminoisothiazole, 5-aminopyrazole, 2-aminothiophene and 2-amino-1,3,4-thiadiazole, followed by coupling with certain aniline, tetrahydroquinoline, or benzomorpholine compounds containing sulfate groups. These amines may be substituted with a large variety of groups including lower alkyl, lower alkoxy, cyano, carbamoyl, sulfamoyl, and halogen. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool.

Growing community of inventors

Kingsport, TN, United States of America

Ralph R Giles