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US 3,980,634 AGranted
Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith
AssigneeEastman Kodak Company
InventorMax Allen Weaver
Life of this patent
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Abstract
Monoazo compounds containing a phthalimidyl diazo component bearing on the aromatic ring thereof one or two substituents such as halogen or cyano and an aniline disperse azo dye coupling component which may have a substituent such as acetamido, are useful for dyeing polyester fibers on which the compounds exhibit good fastness and dyeability properties.
Claims8
A compound having the formula ##SPC7## ##SPC8##
- wherein
- R.sup.1 is hydrogen;
- lower alkyl;
- arylmethy;
- cyclohexylmethyl;
- 2-cyanoethyl;
- 2-carbamoylethyl;
- aryl;
- cyclohexyl;
- or --Z--R.sup.17 in which Z is ethylene, propylene, or trimethylene and R.sup.17 is succinimido, glutarimido, phthalimido, hydroxy, lower alkanoyloxy, 2-pyrrolidinone, or lower alkoxy;
- R.sup.2 is lower alkyl, chlorine, bromine, nitro, lower alkylsulfonyl, arylsulfonyl, arylthio, aryl-lower-alkylthio, cyclohexylthio, lower alkoxy, aryloxy, 2-benzothiazolythio, 2-thiazolylthio, 2-thiadiazolythio, 2-oxadiazolythio, 1,2,4-triazol-3-ylthio, or 2-pyrimidinylthio;
- R.sup.3 is chlorine, bromine or nitro;
- R.sup.4 is hydrogen, halogen, cyano, nitro, lower alkylsulfonyl, arylsulfonyl, arylthio, cyclohexylthio, lower alkoxy, aryloxy, 2-benzothiazolylthio, 2-thiazolythio, 2-thiadiazolylthio, 2-oxadiazolylthio, 1,2,4-triazol-3-ylthio, or 2-pyrimidinylthio;
- R.sup.5 is hydrogen, lower alkyl, lower alkoxyl, halogen or -NH-R.sup.9 in which R.sup.9 is formyl, lower alkanoyl, lower alkylsulfonyl, aroyl, lower alkoxycarbonyl, carbamoyl, lower alkylcarbamoyl, or lower alkanoyl substituted with halogen, aryl, cyano, lower alkoxy, aryloxy, benzyloxy, lower alkylthio, lower alkylsulfonyl or lower alkanoyloxy;
- R.sup.6 is hydrogen, lower alkyl or lower alkoxy;
- R.sup.7 individually is alkyl containing one to eight carbon atoms;
- cyclohexyl;
- cyclohexyl substituted with lower alkyl;
- or lower alkyl substituted with lower alkoxy, aryl, aryloxy, cyclohexyl, cyano, lower alkanoyloxy, lower alkoxycarbonyl, lower alkoxycarbonyloxy, aroyloxy, lower alkylcarbamoyloxy, arylcarbamoyloxy, or ##EQU2## wherein R.sup.10 individually is hydrogen, lower alkyl or aryl;
- R.sup.11 individually is hydrogen or lower alkyl;
- R.sup.10 and R.sup.11 taken together are --(CH.sub.2).sub.5 or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sup.9 is defined above;
- R.sup.12 is hydrogen, lower alkyl, aryl, or cyclohexyl;
- R.sup.13 is ethylene, propylene, trimethylene o-cyclohexylene, or o-arylene, or when X is --CO--, R.sup.13 also can be --NHCH.sub.2 --, --N(lower alkyl)CH.sub.2 --, --SCH.sub.2 --, --OCH.sub.2 --, or --CH.sub.2 OCH.sub.2 --;
- Y is --CH.sub.2, --CO--, or --SO.sub.2 --;
- and
- R.sup.14 is aryl, benzyl, cyclohexyl, 1,2,4-triazol-3-yl, or 2-benzothiazolyl;
- R.sup.8 individually is hydrogen;
- lower alkyl;
- lower alkyl substituted with lower alkoxy, aryl, aryloxy, cyclohexyl, lower alkanoyloxy, lower alkoxycarbonyl or lower alkoxycarbonyloxy;
- allyl;
- or aryl;
- R.sup.7 and R.sup.8 taken together is --CH.sub.2 CH.sub.2 --Y--CH.sub.2 CH.sub.2 -- in which Y is --CH.sub.2 --, --N(R.sup.9), --O--, --S--, --SO--, or --SO.sub.2 --;
- in which each aryl moiety is phenyl, tolyl, anisyl, ethoxyphenyl, or chlorophenyl.
31 more elements
Dependencies are inferred from the claim text.