US4198205A — Triazinyl-anthraquinone dye formulations for cell…

Claim 1

Independent Claim 446 words

Dyed, water-swellable cellulosic fibers having a dyeing which is fast to washing, dry-cleaning and light, said fibers having been dyed by applying thereto simultaneously or successively water; one of ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol serving as a water retention agent; polyethylene oxide or a reaction product of polyethylene oxide with boric acid in a molar ratio of 3:1; and an essentially water insoluble dye of the formula ##STR420## in which A is unsubstituted or substituted anthraquinonyl, anthrapyridone or anthrapyrimidine group of the formulae ##STR421## in which hal is chloro or bromo; m is zero, 1 or 2; R 1 is hydrogen, chloro, bromo, methyl, ethyl, C 1 to C 6 alkoxy, phenoxy, alkylphenoxy of one to six carbon atoms in the alkyl, chlorophenoxy, bromophenoxy, C 1 to C 6 alkylthio, phenylthio, alkylphenylthio of one to six carbon atoms in the alkyl, acetyl, propionyl, benzoyl, monomethylbenzoyl, dimethylbenzoyl, trimethylbenzoyl, phenoxybenzoyl, C 1 to C 6 alkoxycarbonyl, N-alkylaminocarbonyl or N,N-dialkylaminocarbonyl of one to six carbon atoms per and/or N-alkylsulfamoyl of one to four carbon atoms per alkyl; C 1 to C 5 alkylthio; C 7 to C 10 phenylalkylthio; phenylthio; phenylthio substituted by chloro, bromo, C 1 to C 4 alkyl, methoxy or ethoxy; R 10 is phenyl; C 1 to C 5 alkyl; C 1 to C 8 alkylthio; C 3 to C 8 alkoxyalkyl; C 1 to C 5 alkylamino; methoxy; ethoxy; phenalkylthio of one to five carbon atoms in the alkyl; R 11 is amino or C 1 to C 5 alkylamino; R 13 is hydrogen; C 1 to C 6 alkoxycarbonyl; C 1 to C 4 alkylcarbonyl; benzoyl or cyano; R 15 is hydrogen; C 1 to C 5 alkyl; or phenyl; R 14 is hydrogen; C 1 to C 5 alkyl; phenyl; or C 1 to C 5 alkylphenyl; X is 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 3,N,N-diethylsulfamoylphenyl, 4-methylphenyl, 4-isopropylphenyl or phenyl; B is hydrogen; B 1 is C 1 to C 8 alkyl, 2-hydroxyethyl, alkoxyalkyl of a total of three to seven carbon atoms, phenalkyl of a total of seven to ten carbon atoms, phenoxyalkyl of two to four carbon atoms in the alkyl, phenoxyalkoxyalkyl of four to six carbon atoms in the alkoxyalkyl, cyclohexyl, phenyl or phenyl in which one hydrogen atom is replaced by fluoro, trifluoromethyl, phenalkoxy of seven to eight carbon atoms, carbonylalkoxy of a total of two to five carbon atoms, alkylaminocarbonyl or dialkylsulfamoyl of one to four carbon atoms per alkyl or phenoxy and one to three hydrogen atoms are optionally replaced by methyl, methoxy, ethoxy, chloro or bromo and the substituents may be identical or different; and n is one of the integers 1 and 2.

Claim 2

Dependent Claim 446 words

Dyed, water-swellable cellulosic fibers having a dyeing which is fast to washing, dry-cleaning and light, said fibers having been dyed by applying thereto simultaneously or successively water; one of ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol serving as a water retention agent; polyethylene oxide or a reaction product of polyethylene oxide with boric acid in a molar ratio of 3:1; and an essentially water insoluble dye of the formula ##STR420## in which A is unsubstituted or substituted anthraquinonyl, anthrapyridone or anthrapyrimidine group of the formulae ##STR421## in which hal is chloro or bromo; m is zero, 1 or 2; R 1 is hydrogen, chloro, bromo, methyl, ethyl, C 1 to C 6 alkoxy, phenoxy, alkylphenoxy of one to six carbon atoms in the alkyl, chlorophenoxy, bromophenoxy, C 1 to C 6 alkylthio, phenylthio, alkylphenylthio of one to six carbon atoms in the alkyl, acetyl, propionyl, benzoyl, monomethylbenzoyl, dimethylbenzoyl, trimethylbenzoyl, phenoxybenzoyl, C 1 to C 6 alkoxycarbonyl, N-alkylaminocarbonyl or N,N-dialkylaminocarbonyl of one to six carbon atoms per and/or N-alkylsulfamoyl of one to four carbon atoms per alkyl; C 1 to C 5 alkylthio; C 7 to C 10 phenylalkylthio; phenylthio; phenylthio substituted by chloro, bromo, C 1 to C 4 alkyl, methoxy or ethoxy; R 10 is phenyl; C 1 to C 5 alkyl; C 1 to C 8 alkylthio; C 3 to C 8 alkoxyalkyl; C 1 to C 5 alkylamino; methoxy; ethoxy; phenalkylthio of one to five carbon atoms in the alkyl; R 11 is amino or C 1 to C 5 alkylamino; R 13 is hydrogen; C 1 to C 6 alkoxycarbonyl; C 1 to C 4 alkylcarbonyl; benzoyl or cyano; R 15 is hydrogen; C 1 to C 5 alkyl; or phenyl; R 14 is hydrogen; C 1 to C 5 alkyl; phenyl; or C 1 to C 5 alkylphenyl; X is 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 3,N,N-diethylsulfamoylphenyl, 4-methylphenyl, 4-isopropylphenyl or phenyl; B is hydrogen; B 1 is C 1 to C 8 alkyl, 2-hydroxyethyl, alkoxyalkyl of a total of three to seven carbon atoms, phenalkyl of a total of seven to ten carbon atoms, phenoxyalkyl of two to four carbon atoms in the alkyl, phenoxyalkoxyalkyl of four to six carbon atoms in the alkoxyalkyl, cyclohexyl, phenyl or phenyl in which one hydrogen atom is replaced by fluoro, trifluoromethyl, phenalkoxy of seven to eight carbon atoms, carbonylalkoxy of a total of two to five carbon atoms, alkylaminocarbonyl or dialkylsulfamoyl of one to four carbon atoms per alkyl or phenoxy and one to three hydrogen atoms are optionally replaced by methyl, methoxy, ethoxy, chloro or bromo and the substituents may be identical or different; and n is one of the integers 1 and 2.

Claim 3

Dependent Claim 218 words

Dyed fibers as claimed in claim 1 wherein R 1 is hydrogen, bromo, chloro, acetyl, carbonylalkoxy of one to five carbon atoms in the alkyl, benzoyl, monomethylbenzoyl, dimethylbenzoyl, trimethylbenzoyl, methoxybenzoyl, ethoxybenzoyl, phenoxybenzoyl, N-alkylaminocarbonyl of one to four carbon atoms in the alkyl, nitro, cyano, C 1 to C 4 alkylsulfonyl, phenylsulfonyl, methylphenylsulfonyl or C 1 to C 4 alkoxy; R 2 is hydrogen, hydroxy, amino, C 1 to C 4 alkylamino; phenylamino, phenylamino substituted by C 1 to C 5 alkyl, methoxy, ethoxy or C 2 to C 4 C-acyloxy; or C 1 to C 4 alkoxy; R 3 and R 4 are hydrogen, hydroxy, amino and may be identical or different; R 5 , R 6 , R 7 , R 13 and R 15 are all hydrogen; R 8 and R 11 are both amino; R 9 is phenoxyalkyl or phenalkyl of one to six carbon atoms in the alkyl, or C 1 to C 5 alkyl; R 10 is C 1 to C 5 alkyl, C 1 to C 8 alkylthio or phenalkylthio of two to four carbon atoms in the alkyl; R 14 is hydrogen, hydroxy, phenyl, C 1 to C 3 alkylphenyl or chlorophenyl; and R 15 is hydrogen and X, B, B 1 and n have the meanings given in claim 1.

Claim 4

Dependent Claim 382 words

Dyed, water-swellable cellulosic fibers having a dyeing which is fast to washing, dry-cleaning and light, said fibers having been dyed by applying simultaneously or successively thereto water; one of ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol serving as a water retention agent; polyethylene oxide or a reaction product of polyethylene oxide with boric acid in a molar ratio fo 3:1; and an essentially water insoluble dye of the formula ##STR422## in which A in the formula is a radical of the formula: ##STR423## in which D is hydroxy, amino, C 1 to C 4 -alkylamino, phenylamino, phenylamino substituted by methyl, methoxy, chloro or bromo in the 4-position, alkylcarbonylamino of one to three carbon atoms in the alkyl or benzylamino; E is bromo, acetyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, benzoyl, 4-methylbenzoyl, 2,4,6-trimethylbenzoyl, 4-methoxybenzoyl, 4-phenoxybenzoyl, N-propylaminocarbonyl, nitro, cyano, methylsulfonyl, phenylsulfonyl, 4-methylsulfonyl, methoxy, or 2-oxadiazolyl or 2-thiodiazolyl which bear phenoxyalkyl or phenalkyl of one to six carbon atoms in the alkyl, C 1 to C 5 alkyl, C 1 to C 8 alkylthio or phenalkylthio of two to four carbon atoms in the alkyl as substituents in the 5-position; F is hydrogen, hydroxy, amino or C 1 to C 5 alkylamino; G is hydroxy, amino, phenylamino, benzoylamino or alkylcarbonylamino of one to three carbon atoms in the alkyl; H' is hydrogen, hydroxy or phenylamino and one of the substituents G and H' may be nitro; K is hydrogen, hydroxy, methyl, phenyl, 4-methylphenyl or 4-chlorophenyl; X is 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 3-N,N-diethylsulfamoylphenyl, 4-methylphenyl, methyl, ethyl, 4-isopropylphenyl or phenyl; B is hydrogen; B 1 is C 1 to C 8 alkyl, 2-hydroxyethyl, alkoxyalkyl of a total of three to seven carbon atoms, phenalkyl of a total of seven to ten carbon atoms, phenoxyalkyl of two to four carbon atoms in the alkyl, phenoxyalkoxyalkyl of four to six carbon atoms in the alkoxyalkyl, cyclohexyl, phenyl or phenyl in which one hydrogen atom is substituted by fluoro, trifluoromethyl, phenalkoxy of seven to eight carbon atoms, carbonylalkoxy of a total of two to five carbon atoms, alkylaminocarbonyl or dialkylsulfamoyl of one to four carbon atoms per alkyl or phenoxy and one to three hydrogen atoms may optionally be replaced by methyl, methoxy, ethoxy, chloro or bromo and the substituents may be identical or different; and n is 1 or 2.

Claim 5

Dependent Claim 382 words

Dyed, water-swellable cellulosic fibers having a dyeing which is fast to washing, dry-cleaning and light, said fibers having been dyed by applying simultaneously or successively thereto water; one of ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol serving as a water retention agent; polyethylene oxide or a reaction product of polyethylene oxide with boric acid in a molar ratio fo 3:1; and an essentially water insoluble dye of the formula ##STR422## in which A in the formula is a radical of the formula: ##STR423## in which D is hydroxy, amino, C 1 to C 4 -alkylamino, phenylamino, phenylamino substituted by methyl, methoxy, chloro or bromo in the 4-position, alkylcarbonylamino of one to three carbon atoms in the alkyl or benzylamino; E is bromo, acetyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, benzoyl, 4-methylbenzoyl, 2,4,6-trimethylbenzoyl, 4-methoxybenzoyl, 4-phenoxybenzoyl, N-propylaminocarbonyl, nitro, cyano, methylsulfonyl, phenylsulfonyl, 4-methylsulfonyl, methoxy, or 2-oxadiazolyl or 2-thiodiazolyl which bear phenoxyalkyl or phenalkyl of one to six carbon atoms in the alkyl, C 1 to C 5 alkyl, C 1 to C 8 alkylthio or phenalkylthio of two to four carbon atoms in the alkyl as substituents in the 5-position; F is hydrogen, hydroxy, amino or C 1 to C 5 alkylamino; G is hydroxy, amino, phenylamino, benzoylamino or alkylcarbonylamino of one to three carbon atoms in the alkyl; H' is hydrogen, hydroxy or phenylamino and one of the substituents G and H' may be nitro; K is hydrogen, hydroxy, methyl, phenyl, 4-methylphenyl or 4-chlorophenyl; X is 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 3-N,N-diethylsulfamoylphenyl, 4-methylphenyl, methyl, ethyl, 4-isopropylphenyl or phenyl; B is hydrogen; B 1 is C 1 to C 8 alkyl, 2-hydroxyethyl, alkoxyalkyl of a total of three to seven carbon atoms, phenalkyl of a total of seven to ten carbon atoms, phenoxyalkyl of two to four carbon atoms in the alkyl, phenoxyalkoxyalkyl of four to six carbon atoms in the alkoxyalkyl, cyclohexyl, phenyl or phenyl in which one hydrogen atom is substituted by fluoro, trifluoromethyl, phenalkoxy of seven to eight carbon atoms, carbonylalkoxy of a total of two to five carbon atoms, alkylaminocarbonyl or dialkylsulfamoyl of one to four carbon atoms per alkyl or phenoxy and one to three hydrogen atoms may optionally be replaced by methyl, methoxy, ethoxy, chloro or bromo and the substituents may be identical or different; and n is 1 or 2.

Claim 6

Dependent Claim 121 words

Dyed fibers as claimed in claim 3 in which A in the formula is a radical of the formula: ##STR424## in which D is amino; E is acetyl, benzoyl, methoxy, bromo, phenylsulfonyl or p-methylsulfonyl; F, G and H' each are hydroxy or amino, one or two of them being hydroxy; X is 4-chlorophenyl, 4-methoxyphenyl, 4-methylphenyl or phenyl; B is hydrogen; and B 1 is C 3 to C 8 alkyl, phenalkyl of a total of eight to ten carbon atoms, alkoxyalkyl of a total of five to eight carbon atoms or phenyl in which one or two hydrogen atoms are optionally replaced by C 1 to C 4 alkyl, phenoxy, chloro or trifluoromethyl and the substituents may be identical or different.

Claim 7

Dependent Claim 12 words

Dyed fibers as claimed in claim 3 in which X is phenyl.

Claim 8

Dependent Claim 81 words

Dyed fibers as claimed in claim 3 in which A in the formula is a radical of the formula: ##STR425## X is phenyl; B is hydrogen; K is acetyl; and B' is isopropyl, n-butyl, 2,4-dimethylpentyl-(2), 2-ethylhexyl, β-phenylethyl or 2-chloro-5-trifluoromethylphenyl; or K is methoxy; and B 1 is isopropyl, 2-methylbutyl-(2), n-hexyl or 2,4-dimethylpentyl-(3); or K is bromo; and B 1 is isopropyl; or K is phenylsulfonyl or 4-methylphenylsulfonyl; and B 1 is isopropyl, 2-ethylhexyl, 3-ethoxypropyl, n-pentyl, n-butyl, 4-phenylbutyl-(2), 4-benzyloxyphenyl, 4-isopropylphenyl or 4-phenoxyphenyl.

Claim 9

Dependent Claim 31 words

Dyed fibers as claimed in claim 3 in which A in the formula is a radical of the formula: ##STR426## X is phenyl; B is hydrogen; and B 1 is 4-benzyloxyphenyl.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1983-04-15	1983-10-15	1984-04-15	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1987-04-15	1987-10-15	1988-04-15	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1991-04-15	1991-10-15	1992-04-15	$7700.00	Window Closed / Lapsed

Triazinyl-anthraquinone dye formulations for cellulose or cellulosic fibrous material

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