US4981516A
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Methine colorants and washable ink compositions containing methine colorants
Assignee: MILLIKEN RESEARCH Corp A CORP OF
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Filing: 1989-09-21
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Granted: 1991-01-01
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Expires: 2009-09-21
Abstract
Abstract A washable ink composition is provided which is an aqueous mixture containing water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR1## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R 1 is H or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR2## wherein: R 3 is H or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R 2 is hydrogen or alkyl of one to about five carbons; a and b are each an integer independently selected from one to about forty wherein a+b is an integer of from about 6 to about 80; and Z is a divalent vinylic carbon atom which is covalently bonded to a group or moiety including any of cyano, vinyl carbon, sulfide, sulfoxide, sulfone, allylic oxygen, thiocyano, or carbonyl which is not part of an amide, carboxylic acid or carboxylic acid salt moiety.
Inventors
- 👤 Edward W. Kluger
- 👤 John W. Rekers
- 👤 Judy A. Wagner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 01:50
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/16; C09D11/17; C09B; C09B69/00
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
180 words
A water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR34## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is selected from nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R 1 is selected from or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR35## wherein R 3 is or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R 2 is hydrogen or alkyl of one to about five carbons; a and b are each an integer independently selected from one to about forty wherein a+b is an integer of from about 6 to about 80, and z is a divalent vinylic carbon atom which is covalently bonded to a group or moiety selected from cyano, vinyl carbon, sulfide, sulfoxide, sulfone, allylic oxygen, thiocyano, or carbonyl which is not part of an amide, carboxylic acid or carboxylic acid salt moiety.
Claim 2
Dependent Claim
180 words
A water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR34## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is selected from nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R 1 is selected from or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR35## wherein R 3 is or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R 2 is hydrogen or alkyl of one to about five carbons; a and b are each an integer independently selected from one to about forty wherein a+b is an integer of from about 6 to about 80, and z is a divalent vinylic carbon atom which is covalently bonded to a group or moiety selected from cyano, vinyl carbon, sulfide, sulfoxide, sulfone, allylic oxygen, thiocyano, or carbonyl which is not part of an amide, carboxylic acid or carboxylic acid salt moiety.
Claim 3
Dependent Claim
10 words
A methine colorant of claim 1 wherein X is nitrogen.
Claim 4
Dependent Claim
10 words
A methine colorant of claim 1 wherein X is oxygen.
Claim 5
Dependent Claim
62 words
A methine colorant as defined in claim 1 having the formula: ##STR36## wherein: R 5 and R 6 are each selected from hydrogen, alkyl, alkoxy, halogen or trifluoromethyl; R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing one to about ten carbons, acetyl or benzoyl; and R 7 is selected from alkyl, cycloalkyl or unsubstituted or substituted phenyl.
Claim 6
Dependent Claim
62 words
A methine colorant as defined in claim 1 having the formula: ##STR37## wherein: R 5 and R 6 are each selected from hydrogen, alkyl, alkoxy, halogen or trifluoromethyl; R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing one to about ten carbons, acetyl or benzoyl; and R 7 is selected from alkyl, cycloalkyl or unsubstituted or substituted phenyl.
Claim 7
Dependent Claim
73 words
A methine colorant as defined in claim 1 having the formula: ##STR38## wherein: R 5 is selected from alkyl, alkoxy, halogen or trifluoromethyl; R 7 is selected from alkyl, cycloalkyl or unsubstituted or substituted phenyl; R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl; and R 11 , R 13 and R 14 are each selected from or lower alkyl.
Claim 8
Dependent Claim
48 words
A methine colorant as defined in claim 1 having the formula: ##STR39## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen or trifluoromethyl; and R 15 is selected from H, lower alkyl, phenyl or phenyl substituted with lower alkyl, lower alkoxy or halogen.
Claim 9
Dependent Claim
49 words
A methine colorant as defined in claim 1 having the formula: ##STR40## wherein; R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen or trifluoromethyl; and R 15 is selected from H, lower alkyl, phenyl or phenyl substituted with lower alkyl lower alkoxy or halogen. ##STR41##
Claim 10
Dependent Claim
47 words
A methine colorant as defined in claim 1 having the formula: wherein: R 11 , R 13 and R 14 are each selected from or lower alkyl; and R 15 is selected from H, lower alkyl, phenyl or phenyl substituted with lower alkyl, lower alkoxy or halogen.
Claim 11
Dependent Claim
68 words
A methine colorant as defined in claim 1 having the formula: ##STR42## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 16 and R 17 are each selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 12
Dependent Claim
70 words
A methine colorant as defined in claim 1 having the formula: ##STR43## wherein: e is zero, one or two; each R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 16 is selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 13
Dependent Claim
85 words
A methine colorant as defined in claim 1 having the formula: ##STR44## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; R 11 , R 13 and R 14 are each selected from or lower alkyl; e is 0, 1 or 2; and R 16 is selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 14
Dependent Claim
70 words
A methine colorant as defined in claim 1 having the formula: ##STR45## wherein: each R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; e is 1, 2 or 3; and R 16 is selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkyl-sulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 15
Dependent Claim
39 words
A methine colorant as defined in claim 1 having the formula: ##STR46## wherein: each of R 5 and R 6 is selected from H, alkyl alkoxy, halogen, or trifluoromethyl; and R 18 is phenyl, beta-naphthyl, alpha-naphthyl, thiophenyl, or halothiophenyl.
Claim 16
Dependent Claim
39 words
A methine colorant as defined in claim 1 having the formula: ##STR47## wherein: each of R 5 and R 6 is selected from H, alkyl, alkoxy, halogen or trifluoromethyl; and R 18 is phenyl, beta-naphthyl, alpha-naphthyl, thiophenyl, or halothiophenyl.
Claim 17
Dependent Claim
43 words
A methine colorant as defined in claim 1 having the formula ##STR48## wherein: each of R 5 and R 6 is selected from H, alkyl, alkoxy. halogen, or trifluoromethyl; and R 19 is cyano, or lower carbalkoxy containing one to about 10 carbons.
Claim 18
Dependent Claim
52 words
A methine colorant as defined in claim 1 having the formula: ##STR49## wherein: R 5 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; R 11 R 13 and R 14 are each selected from or lower alkyl; and R 19 is cyano or lower carbalkoxy containing one to about ten carbons.
Claim 19
Dependent Claim
43 words
A methine colorant as defined in claim 1 having the formula: ##STR50## wherein; each of R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 19 is cyano or lower carbalkoxy containing one to about ten carbons.
Claim 20
Dependent Claim
191 words
A washable ink composition which comprises an aqueous mixture of water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR51## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is selected from nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R 1 is selected from or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR52## wherein R 3 is H or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R 2 is hydrogen or alkyl of one to about five carbons; a and b are each an integer independently selected from one to about forty wherein a+b is an integer of from about 6 to about 80; and Z is a divalent vinylic carbon atom which is covalently bonded to a # group or moiety selected from cyano, vinyl carbon, sulfide, sulfoxide, sulfone, allylic oxygen, thiocyano, or carbonyl which is not part of an amide, carboxylic acid or carboxylic acid salt moiety.
Claim 21
Dependent Claim
191 words
A washable ink composition which comprises an aqueous mixture of water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR51## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is selected from nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R 1 is selected from or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR52## wherein R 3 is H or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R 2 is hydrogen or alkyl of one to about five carbons; a and b are each an integer independently selected from one to about forty wherein a+b is an integer of from about 6 to about 80; and Z is a divalent vinylic carbon atom which is covalently bonded to a # group or moiety selected from cyano, vinyl carbon, sulfide, sulfoxide, sulfone, allylic oxygen, thiocyano, or carbonyl which is not part of an amide, carboxylic acid or carboxylic acid salt moiety.
Claim 22
Dependent Claim
11 words
A composition as defined in claim 19 wherein X is nitrogen.
Claim 23
Dependent Claim
11 words
A composition as defined in claim 1 wherein X is oxygen.
Claim 24
Dependent Claim
64 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR53## wherein: R 5 and R 6 are each selected from hydrogen, alkyl, alkoxy, halogen, or trifluoromethyl; R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing one to about ten carbons, acetyl or benzoyl; and R 7 is selected from alkyl, cycloalkyl or unsubstituted or substituted phenyl.
Claim 25
Dependent Claim
64 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR54## wherein: R 5 and R 6 are each selected from hydrogen, alkyl, alkoxy, halogen or trifluoromethyl; R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing one to about ten carbons, acetyl or benzoyl; and R 7 is selected from alkyl, cycloalkyl or unsubstituted or substituted phenyl.
Claim 26
Dependent Claim
76 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR55## wherein: R 5 is selected from H, alkyl, alkoxy, halogen or trifluoromethyl; R 7 is selected from alkyl, cycloalkyl or unsubstituted or substituted pheny; R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl; and R 11 R 13 and R 14 are each selected from H or lower, alkyl.
Claim 27
Dependent Claim
50 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR56## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen or trifluoromethyl; and R 15 is selected from H, lower alkyl, phenyl or phenyl substituted with lower alkyl, lower alkoxy or halogen.
Claim 28
Dependent Claim
50 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR57## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen or trifluoromethyl; and R 15 is selected from H, lower alkyl, phenyl or phenyl substituted with lower alkyl, lower alkoxy or halogen.
Claim 29
Dependent Claim
51 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR58## to wherein: R 11 , R 13 and R 14 are each selected from or lower alkyl; and R 15 is selected from H, lower alkyl, phenyl or phenyl substituted with lower alkyl, lower alkoxy or halogen.
Claim 30
Dependent Claim
70 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR59## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 16 and R 17 are each selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons acetyl or benzoyl.
Claim 31
Dependent Claim
71 words
A composition defined in claim 19 wherein the colorant has the formula: ##STR60## wherein: e is zero, one or two; each R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 16 is selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 32
Dependent Claim
87 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR61## wherein: R 5 and R 6 are each selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; R 11 , R 13 and R 14 are each selected from or lower alkyl; e is 0, 1 or 2; and R 16 is selected from oxygen or CR 8 R 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 33
Dependent Claim
72 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR62## wherein: each R 5 and R 6 is selected form H, alkyl, alkoxy, halogen, or trifluoromethyl; e is 1, 2 or 3; and R 16 is selected from oxygen or Cr 8 r 8 wherein each R 8 is selected from cyano, alkylsulfonyl, cycloalkyl-sulfonyl arylsulfonyl, or lower carbalkoxy containing from one to about ten carbons, acetyl or benzoyl.
Claim 34
Dependent Claim
41 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR63## wherein: each of R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl, and R 18 is phenyl, beta-naphthyl, alpha-naphthyl, thiophenyl, or halothiophenyl.
Claim 35
Dependent Claim
40 words
A composition defined in claim 19 wherein the colorant has the formula: ##STR64## wherein: each of R 5 and R 6 is selected from H, alkyl, alkoxy, halogen or trifluoromethyl; and R 18 is phenyl, beta-naphthyl, alpha-naphthyl, thiophenyl, or halothiophenyl.
Claim 36
Dependent Claim
45 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR65## wherein: each of R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 19 is cyano, or lower carbalkoxy containing one to about ten carbons.
Claim 37
Dependent Claim
56 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR66## wherein: R 5 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; R 11 , R 13 and R 14 are each selected from H or lower alkyl; and R 19 is cyano or lower carbalkoxy containing one to about ten carbons.
Claim 38
Dependent Claim
45 words
A composition as defined in claim 19 wherein the colorant has the formula: ##STR67## wherein: each of R 5 and R 6 is selected from H, alkyl, alkoxy, halogen, or trifluoromethyl; and R 19 is cyano or lower carbalkoxy containing one to about ten carbons.
References Cited (Backward Citations)
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