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US4169091A Expired / Lapsed US ⏱️ 0.0 years remaining

Symmetrical and asymmetrical disazo compounds containing a bis-(nitro-aryloxy)alkane middle component

Assignee: Hoechst AG
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Filing: 1977-12-21
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Granted: 1979-09-25
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Expires: 1997-12-21
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Abstract

Abstract Symmetrical and asymmetrical disazo compounds of the formula ##STR1## wherein K is the radical of an enolized or enolizable coupling component, Z is hydrogen, halogen, lower alkyl, lower alkoxy or nitro and N is 1 to 10 and Wherein an asymmetry can be caused by a different position of the substituents on the benzene rings A and B and/or by different substituents Z and/or different coupling component radicals K, and mixtures of such compounds are colorants, especially pigments, of a high tinctorial strength and purity of shade, good rheological properties in lacquers and printing inks, high luster of colorations, good fastness to light, solvents, alkali, acids and migration, combined with a good covering power. Especially the combination of good covering power and high tinctorial strength is advantageous for lacquers and printing inks.

Inventors

  • 👤 Rudolf Kuhne
  • 👤 Heinrich Hamal

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 11:37
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/22; C08K5/23; C08K5/235; C09; C09B; C09B35/00; C09B35/02; C09B35/039; C09B35/22

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 280 words
A disazo compound of the formula ##STR14## or a mixture thereof, in which n is a number from 1 to 10; Z is hydrogen or halogen, alkyl or alkoxy of up to 4 carbon atoms, or nitro; and K represents identical or different radicals of the formula ##STR15## in which x 1 and x 2 are hydrogen, fluorine, chlorine or bromine, or alkyl or alkoxy of 1 to 6 carbon atoms, or x 1 and x 2 , together with the phenyl moiety to which they are attached, form a naphthalene, benzimidazolone or benzoxazolone ring; y 1 is hydrogen, fluorine, chlorine, bromine, or alkyl, alkoxy or carbalkoxy of 1 to 6 carbon atoms in the alkyl moiety, cyano, trifluoromethyl, alkanoylamino with up to 5 carbon atoms, benzoylamino, benzoylamino substituted by chlorine or alkyl or alkoxy of up to 4 carbon atoms, or a group of the formula --X--NR'--R", in which X is CO or SO 2 , R' is hydrogen or alkyl of 1 to 4 carbon atoms and R" is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl; R 1 is alkyl of 1 to 6 carbon atoms, carboxyl or carbalkoxy with 1 to 6 carbon atoms in the alkyl moiety; z 1 and z 2 are hydrogen, fluorine, chlorine or bromine or alkyl or alkoxy of 1 to 6 carbon atoms, or z 1 and z 2 together with the phenyl moiety to which they are attached from a naphthyl moiety; and z 3 is hydrogen, fluorine, chlorine or bromine, alkyl or alkoxy of 1 to 6 carbon atoms or a group of the formula --N--NR'--R", in which X, R' and R" are as defined above.
Claim 2
Dependent Claim 280 words
A disazo compound of the formula ##STR14## or a mixture thereof, in which n is a number from 1 to 10; Z is hydrogen or halogen, alkyl or alkoxy of up to 4 carbon atoms, or nitro; and K represents identical or different radicals of the formula ##STR15## in which x 1 and x 2 are hydrogen, fluorine, chlorine or bromine, or alkyl or alkoxy of 1 to 6 carbon atoms, or x 1 and x 2 , together with the phenyl moiety to which they are attached, form a naphthalene, benzimidazolone or benzoxazolone ring; y 1 is hydrogen, fluorine, chlorine, bromine, or alkyl, alkoxy or carbalkoxy of 1 to 6 carbon atoms in the alkyl moiety, cyano, trifluoromethyl, alkanoylamino with up to 5 carbon atoms, benzoylamino, benzoylamino substituted by chlorine or alkyl or alkoxy of up to 4 carbon atoms, or a group of the formula --X--NR'--R", in which X is CO or SO 2 , R' is hydrogen or alkyl of 1 to 4 carbon atoms and R" is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl; R 1 is alkyl of 1 to 6 carbon atoms, carboxyl or carbalkoxy with 1 to 6 carbon atoms in the alkyl moiety; z 1 and z 2 are hydrogen, fluorine, chlorine or bromine or alkyl or alkoxy of 1 to 6 carbon atoms, or z 1 and z 2 together with the phenyl moiety to which they are attached from a naphthyl moiety; and z 3 is hydrogen, fluorine, chlorine or bromine, alkyl or alkoxy of 1 to 6 carbon atoms or a group of the formula --N--NR'--R", in which X, R' and R" are as defined above.
Claim 3
Dependent Claim 9 words
A symmetric disazo compound as defined in claim 1.
Claim 4
Dependent Claim 9 words
An asymmetric disazo compound as defined in claim 1.
Claim 5
Dependent Claim 9 words
A mixture of compounds as defined in claim 1.
Claim 6
Dependent Claim 13 words
A mixture of symmetric and asymmetric disazo compounds as defined in claim 1.
Claim 7
Dependent Claim 152 words
Disazo compound according to claim 1, wherein K represents identical or different radicals of the formula ##STR16## where x 1 and x 2 denote hydrogen, fluorine, chlorine or bromine, or alkyl or alkoxy with 1 to 6 carbon atoms in each case and y 1 denotes hydrogen, fluorine, chlorine or bromine, alkyl, alkoxy or carbalkoxy with 1 to 6 carbon atoms in the alkyl radical in each case, cyano, trifluoromethyl, alkanoylamino with up to 5 C atoms, benzoylamino which is optionally substituted by chlorine or alkyl or alkoxy with up to 4 C atoms in each case, or a group of the formula --X--NR'--R", in which X denotes CO or SO 2 , R' denotes hydrogen or alkyl with 1 to 4 C atoms and R" denotes hydrogen, alkyl with 1 to 4 C atoms or phenyl or x 1 and x 2 together form a fused benzene, imidazolone or oxazolone ring.
Claim 8
Dependent Claim 139 words
Disazo compound according to claim 1, wherein K represents identical or different radicals of the formula ##STR17## where R 1 is alkyl with 1 to 6 carbon atoms, carboxyl or carbalkoxy with 1 to 6 carbon atoms in the alkyl radical, z 1 and z 2 denote hydrogen, fluorine, chlorine or bromine, or alkyl or alkoxy with 1 to 6 carbon atoms in each case and z 3 denotes hydrogen, fluorine, chlorine or bromine, alkyl or alkoxy with 1 to 6 carbon atoms in each case or a group of the formula --N--NR'--R", in which X denotes CO or SO 2 , R' denotes hydrogen or alkyl with 1 to 4 C atoms and R" denotes hydrogen or alkyl with 1 to 4 C atoms or phenyl or z 1 and z 2 together form a fused benzene ring.
Claim 9
Dependent Claim 62 words
A symmetric disazo compound according to claim 3, wherein n is 1 or 2, Z is hydrogen, x 1 is hydrogen, methyl or carbamoyl, x 2 is hydrogen or methyl and y 1 is hydrogen, the azo groups being in 2- or 4-position and the nitro groups being in 3-, 5- or 6-position, the position of the ether oxygen defining the 1-position.
Claim 10
Dependent Claim 31 words
The compound as claimed in claim 8, wherein n is 1, x 1 and x 2 are hydrogen, the azo groups being in 2-position and the nitro groups being in 5-position.
Claim 11
Dependent Claim 31 words
The compound as claimed in claim 8, wherein n is 1, x 1 is o-methyl, x 2 is hydrogen, the azo groups being in 2-position and the nitro groups in 5-position.
Claim 12
Dependent Claim 31 words
The compound as claimed in claim 8, wherein n is 1, x 1 is o-methyl, x 2 is p-methyl, the azo groups being in 4-position and the nitro groups in 3-position.
Claim 13
Dependent Claim 31 words
The compound as claimed in claim 8, wherein n is 1, x 1 is p-carbamoyl, x 2 is hydrogen, the azo groups being in 2-position and the nitro groups in 5-position.
Claim 14
Dependent Claim 31 words
The compound as claimed in claim 8, wherein n is 2, x 1 is o-methyl, x 2 is hydrogen, the azo groups being in 2-position and the nitro groups in 5-position.

References Cited (Backward Citations)

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US3124556A Cited
US3218311A Cited
US3759894A Cited
US3954398A Cited
US3910875A Cited
DE2434432A1 Cited
GB1438900A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-09-24 1983-03-26 1983-09-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-09-24 1987-03-26 1987-09-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-09-24 1991-03-26 1991-09-25 $7700.00 Window Closed / Lapsed

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