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Cationic dyes containing an aryloxy group linked through a bridging radical to a quaternized nitrogen atom

Assignee: Sandoz AG
•
Filing: 1975-11-28
•
Granted: 1978-02-07
•
Expires: 1995-11-28
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Abstract

Abstract Disclosed are basic dyes, e.g., azo dyes and anthraquinone dyes free from sulphonic acid groups and which contain, as characteristic group, a group of the formula <IMAGE> in which R and R1, independently, are substituted or unsubstituted C1-4 alkyl or are linked to form a ring, or ONE OF R and R1 is -NH2 or C1-4 alkoxy, the other substituted or unsubstituted alkyl, R2 and R3, independently, are hydrogen or C1-4 alkyl, Y is a bridging group, Q is unsubstituted or substituted phenyl, biphenylyl, naphthyl or <IMAGE> in which R7 is <IMAGE> <IMAGE> where R8 ic C1-4 alkyl, and A- is an anion. These dyes are useful for the dyeing and printing of polymers and copolymers of acrylonitrile and asymmetrical dicyanoethylene as well as polyesters and polyamides modified to contain acid groups. The dyes build-up well and exhibit good pH stability and stability to boiling. The obtained dyeings are level and possess good fastness to light, wet treatments, solvents, heat treatments and cross-dyeing.

Inventors

  • 👤 Beat Henzi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 12:55
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/91; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14; C07D249/00; C07D249/02; C07D249/08; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/82; C09; C09B; C09B1/00; C09B1/16; C09B1/20; C09B1/50; C09B1/503; C09B1/54; C09B1/545; C09B23/00; C09B23/10; C09B23/105; C09B23/14; C09B23/145; C09B23/16; C09B23/162; C09B23/164; C09B62/00; C09B62/44; C09B62/78; C09B69/00

Claims Analysis

Total Claims: 64
Claim 1
Independent Claim 393 words
A dye of the formula wherein G is the residue of a carbocylic monoazodye R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, amino or alkoxy of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, R 2 is hydrogen or alkyl of 1 to 4 carbon atoms, R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, Q is ##STR190## wherein n R 7 is ##STR191## wherein each R 8 is independently alkyl of 1 to 4 carbon atoms, each R 9 is independently hydroxy, halo, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy, alkoxy of 1to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy, cycloalkyl of 5 or 6 carbon atoms, cycloalkyl of 5 or 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, nitro, phenoxy, naphthyloxy, -CO-Ro, --CO-O-Ro, --O-CO-Ro, --CO-NH-Ro, --CO-N(Ro) 2 , --O-CO-N(Ro) 2 , -NH-CO-Ro, --SO 2 -Ro, -SO 2 -NH-Ro or -O-SO 2 -N(Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, R 10 is hydrogen, halo or alkyl of 1to 4 carbon atoms, R 11 is hydrogen alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, halo, trifluoromethyl, nitro, cyano, -CO-Ro, --CO-O-Ro, --O-CO-Ro, --CO-NH-Ro, --NH-CO-Ro, -SO 2 -Ro --SO 2 --NH-Ro or -SO 2 -N)Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, and a is 0, 1, 2, 3, 4, or 5, with the proviso that when a is 4 or 5 each R 9 must be halo, Y is ##STR192## wherein each R 4 is independently hydrogen or alkyl of 1 to 4 carbon atoms, R 5 is ##STR193## --SO--, --SO 2 --or --CO--, wherein R 6 is hydrogen or alkyl of 1 to 4 carbon atoms, and x is 1 to 6, and A - is an anion, wherein each halo is independently chloro, bromo or iodo, with the proviso that the molecule is free of sulfo groups.
Claim 2
Dependent Claim 393 words
A dye of the formula wherein G is the residue of a carbocylic monoazodye R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, amino or alkoxy of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, R 2 is hydrogen or alkyl of 1 to 4 carbon atoms, R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, Q is ##STR190## wherein n R 7 is ##STR191## wherein each R 8 is independently alkyl of 1 to 4 carbon atoms, each R 9 is independently hydroxy, halo, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy, alkoxy of 1to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy, cycloalkyl of 5 or 6 carbon atoms, cycloalkyl of 5 or 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, nitro, phenoxy, naphthyloxy, -CO-Ro, --CO-O-Ro, --O-CO-Ro, --CO-NH-Ro, --CO-N(Ro) 2 , --O-CO-N(Ro) 2 , -NH-CO-Ro, --SO 2 -Ro, -SO 2 -NH-Ro or -O-SO 2 -N(Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, R 10 is hydrogen, halo or alkyl of 1to 4 carbon atoms, R 11 is hydrogen alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, halo, trifluoromethyl, nitro, cyano, -CO-Ro, --CO-O-Ro, --O-CO-Ro, --CO-NH-Ro, --NH-CO-Ro, -SO 2 -Ro --SO 2 --NH-Ro or -SO 2 -N)Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, and a is 0, 1, 2, 3, 4, or 5, with the proviso that when a is 4 or 5 each R 9 must be halo, Y is ##STR192## wherein each R 4 is independently hydrogen or alkyl of 1 to 4 carbon atoms, R 5 is ##STR193## --SO--, --SO 2 --or --CO--, wherein R 6 is hydrogen or alkyl of 1 to 4 carbon atoms, and x is 1 to 6, and A - is an anion, wherein each halo is independently chloro, bromo or iodo, with the proviso that the molecule is free of sulfo groups.
Claim 3
Dependent Claim 27 words
A dye according to claim 1 wherein R is alkyl of 1 to 4 carbon atoms, and R 1 is alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim 20 words
A dye according to claim 2 wherein R 2 is hydrogen or methyl, and R 3 is hydrogen or methyl.
Claim 5
Dependent Claim 37 words
A dye according to claim 3 wherein Y is ##STR194## --CH 2 O-CH 2 CH 2 --, wherein R 4 is hydrogen or alkyl of 1 to 4 carbon atoms, and x' is 1, 2 or 3.
Claim 6
Dependent Claim 43 words
A dye according to claim 4 wherein Q is phenyl, naphthyl, biphenylyl, phenyl substituted by halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, cyano or nitro or phenyl substituted by 2 to 5 chloro substituents.
Claim 7
Dependent Claim 57 words
A dye according to claim 1 having the formula ##STR195## wherein D is a diazo component radical, K is a coupling component radical, each T" is independently ##STR196## W is a bridging group, q is 0 or 1, and t is 1 or 2, with the proviso that each --Wa-T" independently is bound to D or K.
Claim 8
Dependent Claim 33 words
A dye according to claim 6 having the formula ##STR197## wherein Ka' is a coupling component radical, Z is -CO- or SO 2 , T" is ##STR198## and t is 1 or 2.
Claim 9
Dependent Claim 1012 words
A compound of the formula ##STR199## wherein R 16 is hydrogen, phenyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl, phenoxy, alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzoyloxy, --CO-N-(Ra) 2 or --O-CO-N(Ra) 2 , wherein each Ra is independently hydrogen or alkyl of 1 to 4 carbon atoms, R 17 is ##STR200## wherein R 25 is hydrogen or alkyl of 1 to 4 carbon atoms, R 19 is hydrogen, nitro, halo, cyano, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, -CO-Ro, --COORo, --CO--NHRo or -SO 2 -N(R 21 ) 2 , wherein each R 21 is independently alkyl of 1 to 4 carbon atoms, and Ro is alkyl of 1 to 4 carbon atoms or phenyl, each of R 119 and R' 119 is independently hydrogen, nitro, halo, cyano, alkyl of 1 to 4 carbon atoms, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, R 219 is hydrogen, halo, nitro or cyano, with the proviso that at least one of R 19 , R 119 , R' 119 and R 219 is hydrogen or halo K' is ##STR201## wherein R 18 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, Ka' is ##STR202## wherein each of R 18 ' and R 19 ' is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R 18 ' and R 19 ' is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, R 21 ' is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, R 24 ' is hydroxy, amino or anilino, and each of R 181 and R 191 is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that at least one of R 181 and R 191 is hydrogen or alkyl of 1 to 4 carbon atoms, Ka" is ##STR203## wherein each of R 18 ' and R 19 ' is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R 18 ' and R 19 ' is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, and R 21 ' is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, Z is --CO- or --SO 2 , t is 1 or 2, Hal is halo, and T" is ##STR204## wherein R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, amino or alkoxy of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, R 2 is hydrogen or alkyl of 1 to 4 carbon atoms, R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, Q is ##STR205## wherein R 7 is ##STR206## wherein each R 8 is independently alkyl of 1 to 4 carbon atoms, each R 9 is independently hydroxy; halo; alkyl of 1 to 4 carbon atoms; alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy; alkoxy of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy; cycloalkyl of 5 or 6 carbon atoms; cycloalkyl of 5 or 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms; trifluoromethyl; cyano; nitro; phenoxy; naphthyloxy; --CO--Ro; --CO--O--Ro; --O--CO--Ro; --CO--NH--Ro; --CO--N(Ro) 2 ; --O--CO--N(Ro) 2 ; --NH--CO--Ro; --SO 2 --Ro; --SO 2 --NH--Ro or --O--SO 2 --N(Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, R 10 is hydrogen, halo or alkyl of 1 to 4 carbon atoms, R 11 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, halo, trifluoromethyl, nitro, cyano, --CO--Ro, --CO--O--Ro, --O--CO--Ro, --CO--NH--Ro, --NH--CO--Ro, --SO 2 --Ro, --SO 2 --NH--Ro or --SO 2 --N(Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, and a is 0, 1. 2, 3, 4, or 5, with the proviso that when a is 4 or 5 each R 9 must be halo, Y is ##STR207## wherein each R 4 is independently hydrogen or alkyl of 1 to 4 carbon atoms, R 5 is ##STR208## --SO--, --SO 2 -- or --CO--, wherein R 6 is hydrogen or alkyl of 1 to 4 carbon atoms, and x is 1 to 6, and A - is an anion, wherein each halo is independently chloro, bromo or iodo.
Claim 10
Dependent Claim 1012 words
A compound of the formula ##STR199## wherein R 16 is hydrogen, phenyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl, phenoxy, alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzoyloxy, --CO-N-(Ra) 2 or --O-CO-N(Ra) 2 , wherein each Ra is independently hydrogen or alkyl of 1 to 4 carbon atoms, R 17 is ##STR200## wherein R 25 is hydrogen or alkyl of 1 to 4 carbon atoms, R 19 is hydrogen, nitro, halo, cyano, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, -CO-Ro, --COORo, --CO--NHRo or -SO 2 -N(R 21 ) 2 , wherein each R 21 is independently alkyl of 1 to 4 carbon atoms, and Ro is alkyl of 1 to 4 carbon atoms or phenyl, each of R 119 and R' 119 is independently hydrogen, nitro, halo, cyano, alkyl of 1 to 4 carbon atoms, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, R 219 is hydrogen, halo, nitro or cyano, with the proviso that at least one of R 19 , R 119 , R' 119 and R 219 is hydrogen or halo K' is ##STR201## wherein R 18 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, Ka' is ##STR202## wherein each of R 18 ' and R 19 ' is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R 18 ' and R 19 ' is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, R 21 ' is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, R 24 ' is hydroxy, amino or anilino, and each of R 181 and R 191 is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that at least one of R 181 and R 191 is hydrogen or alkyl of 1 to 4 carbon atoms, Ka" is ##STR203## wherein each of R 18 ' and R 19 ' is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R 18 ' and R 19 ' is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, and R 21 ' is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, Z is --CO- or --SO 2 , t is 1 or 2, Hal is halo, and T" is ##STR204## wherein R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, amino or alkoxy of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, R 2 is hydrogen or alkyl of 1 to 4 carbon atoms, R 3 is hydrogen or alkyl of 1 to 4 carbon atoms, Q is ##STR205## wherein R 7 is ##STR206## wherein each R 8 is independently alkyl of 1 to 4 carbon atoms, each R 9 is independently hydroxy; halo; alkyl of 1 to 4 carbon atoms; alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy; alkoxy of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy; cycloalkyl of 5 or 6 carbon atoms; cycloalkyl of 5 or 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms; trifluoromethyl; cyano; nitro; phenoxy; naphthyloxy; --CO--Ro; --CO--O--Ro; --O--CO--Ro; --CO--NH--Ro; --CO--N(Ro) 2 ; --O--CO--N(Ro) 2 ; --NH--CO--Ro; --SO 2 --Ro; --SO 2 --NH--Ro or --O--SO 2 --N(Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, R 10 is hydrogen, halo or alkyl of 1 to 4 carbon atoms, R 11 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, halo, trifluoromethyl, nitro, cyano, --CO--Ro, --CO--O--Ro, --O--CO--Ro, --CO--NH--Ro, --NH--CO--Ro, --SO 2 --Ro, --SO 2 --NH--Ro or --SO 2 --N(Ro) 2 , wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, and a is 0, 1. 2, 3, 4, or 5, with the proviso that when a is 4 or 5 each R 9 must be halo, Y is ##STR207## wherein each R 4 is independently hydrogen or alkyl of 1 to 4 carbon atoms, R 5 is ##STR208## --SO--, --SO 2 -- or --CO--, wherein R 6 is hydrogen or alkyl of 1 to 4 carbon atoms, and x is 1 to 6, and A - is an anion, wherein each halo is independently chloro, bromo or iodo.
Claim 11
Dependent Claim 266 words
A compound according to claim 8 having the formula ##STR209## wherein R 16 is hydrogen, phenyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl, phenoxy, alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzoyloxy, --CO--N(Ra) 2 or --O--CO--2, R 17 is ##STR210## wherein R 25 is hydrogen or alkyl of 1 to 4 carbon atoms, R 19 is hydrogen, nitro, halo, cyano, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CO--Ro, --COORo, --CO--NHRo or --SO 2 --N(R 21 ) 2 , wherein each R 21 is independently alkyl of 1 to 4 carbon atoms. each of R 119 and R' 119 is independently hydrogen, nitro, halo, cyano, alkyl of 1 to 4 carbon atoms, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, R 219 is hydrogen, halo, nitro or cyano, with the proviso that at least one of R 19 , R 119 , R' 119 and R 219 is hydrogen, K' is ##STR211## wherein R 18 is hydrogen or halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, and T" is ##STR212## wherein each Ra is independently hydrogen or alkyl of 1 to 4 carbon atoms, and each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl.
Claim 12
Dependent Claim 45 words
A compound according to claim 9 wherein ##STR213## wherein Ra' is hydrogen, halo, nitro or cyano, Ra" is hydrogen or halo, each Ra'" is independently hydrogen or halo, and each of R 1a and R 2a is independently alkyl of 1 to 4 carbon atoms.
Claim 13
Dependent Claim 27 words
A compound according to claim 10 wherein R 16 is alkyl of 1 to 4 carbon atoms, R 25 is hydrogen or methyl, and K' is ##STR214##
Claim 14
Dependent Claim 24 words
A compound according to claim 11 wherein R 16 is methyl or ethyl, R 18 is hydrogen or methyl, and R 25 is hydrogen.
Claim 15
Dependent Claim 39 words
A compound according to claim 9 wherein R is alkyl of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms, R 2 is hydrogen or methyl, and R 3 is hydrogen or methyl.
Claim 16
Dependent Claim 44 words
A compound according to claim 13 wherein Y is ##STR215## --CH═CH--CH 2 --, --C|C--CH 2 -- or --CH 2 --O--CH 2 --CH 2 --, wherein R 4 is hydrogen or alkyl of 1 to 4 carbon atoms, and x' is 1, 2 or 3.
Claim 17
Dependent Claim 43 words
A compound according to claim 14 wherein Q is phenyl, naphthyl, biphenylyl, phenyl substituted by halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, cyano or nitro or phenyl substituted by 2 to 5 chloro substituents.
Claim 18
Dependent Claim 36 words
A compound according to claim 15 wherein R is methyl or ethyl, R 1 is methyl or ethyl, R 2 is hydrogen, R 3 is hydrogen, R 4 is hydrogen or methyl, and x' is 1.
Claim 19
Dependent Claim 26 words
A compound according to claim 16 wherein Q is phenyl, 2-naphthyl or phenyl substituted by 1 to 5 chloro substituents, and Y is --CH 2 --.
Claim 20
Dependent Claim 255 words
A compound according to claim 8 having the formula ##STR216## wherein Ka' is ##STR217## wherein each of R' 18 and R' 19 is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R' 18 and R' 19 is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, R' 21 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, R' 24 is hydroxy, amino or anilino, and each of R 181 and R 191 is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that at least one of R 181 and R 191 is hydrogen or alkyl of 1 to 4 carbon atoms, Z is --CO-- or --SO 2 t is 1 or 2, and T" is ##STR218##
Claim 21
Dependent Claim 39 words
A compound according to claim 18 wherein R is alkyl of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms, R 2 is hydrogen or methyl, and R 3 is hydrogen or methyl.
Claim 22
Dependent Claim 44 words
A compound according to claim 19 wherein Y is ##STR219## --CH═--CH 2 --, --C|C--CH 2 -- or --CH 2 --O--CH 2 --CH 2 --, wherein R 4 is hydrogen or alkyl of 1 to 4 carbon atoms, and x' is 1, 2 or 3.
Claim 23
Dependent Claim 43 words
A compound according to claim 20 wherein Q is phenyl, naphthyl, biphenylyl, phenyl substituted by halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, cyano or nitro or phenyl substituted by 2 to 5 chloro substituents.
Claim 24
Dependent Claim 36 words
A compound according to claim 21 wherein R is methyl or ethyl, R 1 is methyl or ethyl, R 2 is hydrogen, R 3 is hydrogen, R 4 is hydrogen or methyl, and x' is 1.
Claim 25
Dependent Claim 26 words
A compound according to claim 22 wherein Q is phenyl, 2-naphthyl or phenyl substituted by 1 to 5 chloro substituents, and Y is --CH 2 --.
Claim 26
Dependent Claim 142 words
A compound according to claim 8 having the formula ##STR220## wherein Ka" is ##STR221## wherein each of R' 18 and R' 19 is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R' 18 and R' 19 is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, and R' 21 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, Hal is halo, and T" is ##STR222##
Claim 27
Dependent Claim 39 words
A compound according to claim 24 wherein R is alkyl of 1 to 4 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms, R 2 is hydrogen or methyl, and R 3 is hydrogen or methyl.
Claim 28
Dependent Claim 44 words
A compound according to claim 25 wherein Y is ##STR223## --CH═CH--CH 2 --, --C|C--CH 2 -- or --CH 2 --O--CH 2 --CH 2 --, wherein R 4 is hydrogen or alkyl of 1 to 4 carbon atoms, and x' is 1, 2 or 3.
Claim 29
Dependent Claim 43 words
A compound according to claim 26 wherein Q is phenyl, naphthyl, biphenylyl, phenyl substituted by halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, cyano or nitro or phenyl substituted by 2 to 5 chloro substituents.
Claim 30
Dependent Claim 36 words
A compound according to claim 27 wherein R is methyl or ethyl, R 1 is methyl or ethyl, R 2 is hydrogen, R 3 is hydrogen, R 4 is hydrogen or methyl, and x' is 1.
Claim 31
Dependent Claim 26 words
A compound according to claim 28 wherein Q is phenyl, 2-naphthyl or phenyl substituted by 1 to 5 chloro substituents, and Y is --CH 2 --.
Claim 32
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR224##
Claim 33
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR225##
Claim 34
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR226##
Claim 35
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR227##
Claim 36
Dependent Claim 13 words
The compound according to claim 33 wherein A - is Cl - .
Claim 37
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR228##
Claim 38
Dependent Claim 13 words
The compound according to claim 35 wherein A - is Cl - .
Claim 39
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR229##
Claim 40
Dependent Claim 13 words
The compound according to claim 37 wherein A - is Cl - .
Claim 41
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR230##
Claim 42
Dependent Claim 13 words
The compound according to claim 39 wherein A - is Cl - .
Claim 43
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR231##
Claim 44
Dependent Claim 13 words
The compound according to claim 41 wherein A - is Cl - .
Claim 45
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR232##
Claim 46
Dependent Claim 13 words
The compound according to claim 43 wherein A - is Cl - .
Claim 47
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR233##
Claim 48
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR234##
Claim 49
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR235##
Claim 50
Dependent Claim 13 words
The compound according to claim 47 wherein A - is Cl - .
Claim 51
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR236##
Claim 52
Dependent Claim 13 words
The compound according to claim 49 wherein A - is Cl - .
Claim 53
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR237##
Claim 54
Dependent Claim 13 words
The compound according to claim 51 wherein A - is Cl - .
Claim 55
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR238##
Claim 56
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR239##
Claim 57
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR240##
Claim 58
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR241##
Claim 59
Dependent Claim 10 words
A compound according to claim 11 having the formula ##STR242##
Claim 60
Dependent Claim 10 words
A compound according to claim 22 having the formula ##STR243##
Claim 61
Dependent Claim 10 words
A compound according to claim 22 having the formula ##STR244##
Claim 62
Dependent Claim 10 words
A compound according to claim 22 having the formula ##STR245##
Claim 63
Dependent Claim 10 words
A compound according to claim 29 having the formula ##STR246##
Claim 64
Dependent Claim 10 words
A compound according to claim 29 having the formula ##STR247##

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11.5 Years (Year 12) 1989-02-06 1989-08-08 1990-02-07 $7700.00 Window Closed / Lapsed

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