US4051084A
Expired / Lapsed
US
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Cationic dyestuffs
Assignee: Bayer AG
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Filing: 1975-01-09
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Granted: 1977-09-27
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Expires: 1995-01-09
Abstract
Abstract Cationic dyestuffs of the formula ##STR1## wherein R represents alkyl, alkenyl, cycloalkyl or aralkyl, R 1 represents hydrogen, alkyl, alkenyl, cycloalkyl or aralkyl, R 2 represents alkylene, Y represents oxygen or sulphur, R 3 represents a direct bond or -CO-, A represents a carbocyclic six-membered ring or a heterocyclic ring, X - represents an anion and m represents the numbers 0 or 1, With the proviso that m can only be 1 if R 3 denotes an alkylene group, are suitable for dyeing and printing of natural and synthetic materials.
Inventors
- 👤 Hans-Peter Kuhlthau
- 👤 Hermann Beecken
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 23:44
CPC Classifications
C; C09; C09B; C09B44/00; C09B44/10; C09B44/20; C09B44/02; C09B44/04
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
589 words
Dyestuff of the formula: ##STR25## wherein R' represents C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, acetoxy-C 1 -C 6 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 6 -alkyl, carbonyl-C 1 -C 6 -alkyl, aminocarbonyl-C 1 -C 6 -alkyl, C 2 -C 7 -alkenyl, benzyl, phenylethyl, or ##STR26## wherein R 17 denotes hydrogen or methyl and R 18 denotes methyl, ethyl, chloromethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenoxymethyl, or phenyl; R 1 ' represents C 1 -C 6 -alkyl, C 2 -C 7 -alkenyl, cyclopentyl, cyclohexyl, benzyl, β-phenylethyl, C 1 -C 6 -alkylcyclopentyl, C 1 -C 6 -alkylcyclohexyl, C 1 -C 6 -alkylbenzyl, C 1 -C 6 -alkyl-β-phenylethyl or C 1 -C 6 -alkyl substituted by halogen, hydroxyl, C 1 -C 4 -alkoxy, phenoxy, cyano, acetoxy, hydroxycarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyloxy, aminocarbonyl, C 1 -C 4 -alkylsulphonylamino, or C 1 -C 4 -alkylsulphonyl-C 1 -C 4 -alkylamino; R 2 represents ##STR27## R 6 denotes hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenyl, or phenoxymethyl; R 7 denotes hydrogen, methyl, ethyl, butoxymethyl, methoxymethyl, ethoxymethyl, propoxymethyl, allyloxymethyl, phenyl, phenoxymethyl, or --Y--A'; R 8 denotes hydrogen or methyl; p denotes the numbers 1 - 6; Y represents oxygen or sulphur; R 4 represents hydrogen, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, C 1 -C 4 -alkylcarbonyloxy, phenylcarbonyloxy, benzyloxy, β-phenylethyloxy, or either of the last two mentioned radicals substituted in the phenyl ring by C 1 -C 6 -alkyl, cyano, phenyloxy, naphthyloxy, C 1 -C 6 -alkylphenyloxy, C 1 -C 6 -alkylnaphthyloxy, halophenyloxy, or halonaphthyloxy; R 4 , in addition, when joined together with B represents a fused naphthalene ring or a fused tetralin ring; R 5 represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonylamino or C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, C 1 -C 4 -alkylcarbonyloxy, phenylcarbonyloxy, benzyloxy, β-phenylethyloxy, or either of the last two mentioned radicals substituted in the phenyl ring by C 1 -C 6 -alkyl, phenyloxy, naphthyloxy, C 1 -C 6 -alkylphenyloxy, C 1 -C 6 -alkylnaphthyloxy, halophenoxy, or halonaphthyloxy; R 5 , in addition, when joined together with B represent a fused naphthalene ring or a fused tetralin ring; R 13 ' represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, cyclopentyl, cyclohexyl, benzyl, β-phenylethyl, C 1 -C 6 -alkylcyclopentyl, C 1 -C 6 -alkylcyclohexyl, C 1 -C 6 -alkylbenzyl, C 1 -C 6 -alkyl-β-phenylethyl, phenyloxy, naphthyloxy, C 1 -C 6 -alkylphenyloxy, C 1 -C 6 -alkylnaphthyloxy, halophenyloxy, halonapthyloxy, benzyloxy, β-phenylethyl, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, a fused benzene ring, or a fused tetrahydrobenzene ring, either of which is fused in the 4,5-position or 5,6-position of D; R 14 represents C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, phenoxy, benzyloxy, benzyl, trifluoromethyl, halogen, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, a fused benzene ring or a fused tetrahydrobenzene ring either of which is fused in the 6,7-position of D; A' is a member of a group consisting of cyclohexyl, naphthyl, phenyl, or phenyl substituted by chloro, methyl, ethyl, isopropyl, sec. butyl, tert. butyl, tetramethylbutyl, nonyl, dodecyl, phenyl, benzyl, cyclohexyl, phenyl-isopropyl, methoxy, ethoxy, isopropoxy, phenylsulfonyl or methylthio; n represents the numbers 0, 1, 2, or 3; and X.sup.(-) represents an anion.
Claim 2
Dependent Claim
589 words
Dyestuff of the formula: ##STR25## wherein R' represents C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, acetoxy-C 1 -C 6 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 6 -alkyl, carbonyl-C 1 -C 6 -alkyl, aminocarbonyl-C 1 -C 6 -alkyl, C 2 -C 7 -alkenyl, benzyl, phenylethyl, or ##STR26## wherein R 17 denotes hydrogen or methyl and R 18 denotes methyl, ethyl, chloromethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenoxymethyl, or phenyl; R 1 ' represents C 1 -C 6 -alkyl, C 2 -C 7 -alkenyl, cyclopentyl, cyclohexyl, benzyl, β-phenylethyl, C 1 -C 6 -alkylcyclopentyl, C 1 -C 6 -alkylcyclohexyl, C 1 -C 6 -alkylbenzyl, C 1 -C 6 -alkyl-β-phenylethyl or C 1 -C 6 -alkyl substituted by halogen, hydroxyl, C 1 -C 4 -alkoxy, phenoxy, cyano, acetoxy, hydroxycarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyloxy, aminocarbonyl, C 1 -C 4 -alkylsulphonylamino, or C 1 -C 4 -alkylsulphonyl-C 1 -C 4 -alkylamino; R 2 represents ##STR27## R 6 denotes hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenyl, or phenoxymethyl; R 7 denotes hydrogen, methyl, ethyl, butoxymethyl, methoxymethyl, ethoxymethyl, propoxymethyl, allyloxymethyl, phenyl, phenoxymethyl, or --Y--A'; R 8 denotes hydrogen or methyl; p denotes the numbers 1 - 6; Y represents oxygen or sulphur; R 4 represents hydrogen, halogen, C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, C 1 -C 4 -alkylcarbonyloxy, phenylcarbonyloxy, benzyloxy, β-phenylethyloxy, or either of the last two mentioned radicals substituted in the phenyl ring by C 1 -C 6 -alkyl, cyano, phenyloxy, naphthyloxy, C 1 -C 6 -alkylphenyloxy, C 1 -C 6 -alkylnaphthyloxy, halophenyloxy, or halonaphthyloxy; R 4 , in addition, when joined together with B represents a fused naphthalene ring or a fused tetralin ring; R 5 represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonylamino or C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, C 1 -C 4 -alkylcarbonyloxy, phenylcarbonyloxy, benzyloxy, β-phenylethyloxy, or either of the last two mentioned radicals substituted in the phenyl ring by C 1 -C 6 -alkyl, phenyloxy, naphthyloxy, C 1 -C 6 -alkylphenyloxy, C 1 -C 6 -alkylnaphthyloxy, halophenoxy, or halonaphthyloxy; R 5 , in addition, when joined together with B represent a fused naphthalene ring or a fused tetralin ring; R 13 ' represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, cyclopentyl, cyclohexyl, benzyl, β-phenylethyl, C 1 -C 6 -alkylcyclopentyl, C 1 -C 6 -alkylcyclohexyl, C 1 -C 6 -alkylbenzyl, C 1 -C 6 -alkyl-β-phenylethyl, phenyloxy, naphthyloxy, C 1 -C 6 -alkylphenyloxy, C 1 -C 6 -alkylnaphthyloxy, halophenyloxy, halonapthyloxy, benzyloxy, β-phenylethyl, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, a fused benzene ring, or a fused tetrahydrobenzene ring, either of which is fused in the 4,5-position or 5,6-position of D; R 14 represents C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, phenoxy, benzyloxy, benzyl, trifluoromethyl, halogen, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulphonylamino, phenylcarbonylamino, phenylsulphonylamino, a fused benzene ring or a fused tetrahydrobenzene ring either of which is fused in the 6,7-position of D; A' is a member of a group consisting of cyclohexyl, naphthyl, phenyl, or phenyl substituted by chloro, methyl, ethyl, isopropyl, sec. butyl, tert. butyl, tetramethylbutyl, nonyl, dodecyl, phenyl, benzyl, cyclohexyl, phenyl-isopropyl, methoxy, ethoxy, isopropoxy, phenylsulfonyl or methylthio; n represents the numbers 0, 1, 2, or 3; and X.sup.(-) represents an anion.
Claim 3
Dependent Claim
90 words
Dyestuff of the formula ##STR28## wherein R', R 1 ', R 4 , R 5 , R 6 , R 8 , R 13 ', R 14 , n, p, and X - have the same meaning as in claim 1; R 2 " represents ##STR29## R 9 represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, allyloxymethyl, phenyl, phenoxymethyl, or --O--(CH 2 ) q --(O) m --A'; q represents the numbers 1-4; m represents the numbers 0 or 1; and A' represents phenyl or phenyl substituted by chloro or methyl.
Claim 4
Dependent Claim
31 words
Dyestuff according to claim 1, in which R 13 ' represents C 1 -C 4 -alkoxy and R 14 represents methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine, trifluoromethyl, phenoxy or benzyloxy.
Claim 5
Dependent Claim
44 words
Dyestuff according to claim 1 in which R 13 ' represents methoxy or ethoxy, R' represents methyl or ethyl, R 5 represents hydrogen, R 4 represents hydrogen, methoxy, chlorine or methyl, p represents the number 2, n represents the number 0, y represents oxygen.
Claim 6
Dependent Claim
31 words
Dyestuff according to claim 2, in which R 13 ' represents C 1 -C 4 -alkoxy and R 14 represents methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine, trifluoromethyl, phenoxy or benzyloxy.
Claim 7
Dependent Claim
52 words
Dyestuff according to claim 2 in which R 13 ' represents methoxy or ethoxy, R' represents methyl or ethyl, R 5 represents hydrogen, R 4 represents hydrogen, methoxy, chlorine or methyl, q represents the numbers from 1-3, n represents the number 0, p represents the number 2, m represents the number 0.
Claim 8
Dependent Claim
41 words
Dyestuff according to claim 2 in which R 13 ' represents methoxy or ethoxy, R' represents methyl or ethyl, R 5 represents hydrogen, R 4 represents hydrogen, methoxy, chlorine or methyl, q represents the number 2, m represents the number 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-26 | 1981-03-28 | 1981-09-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-26 | 1985-03-28 | 1985-09-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-26 | 1989-03-28 | 1989-09-27 | $7700.00 | Window Closed / Lapsed |