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US5043013A Expired / Lapsed US ⏱️ 0.0 years remaining

Washable ink compositions

Assignee: Milliken Research Corp
•
Filing: 1989-08-15
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Granted: 1991-08-27
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Expires: 2009-08-15
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Abstract

Abstract A washable aqueous ink composition having a viscosity of from about 1.0 to about 6.0 centipoises and containing from about 10 to about 50% by weight of one or more polymeric colorants of the formula: ##STR1## wherein: X is a polar group such as sulfonic acids, sulfonic acid salts, sulfonamides, sulfonates or the like; R is alkylene; Y is H, alkanoyl, carbamoyl, or the like; R 1 is nitrogen, oxygen, sulfur, or a sulfur-containing divalent linking group; a is an integer of from six to about forty; b and c are each independently selected from one or two; d is an integer of from one to four; the product of (a) (b) (c) is an integer of from 6 to about 40; and CHROM is a chromophore such as nitro, nitroso, monoaxo, disazo and trisazo, diarylmethane, triarylmethane, xanthane, acridine, methine, thiazole, indamine, azine, oxazine, or anthraquinone, wherein the (RO) a moiety is bonded to a carbocyclic aromatic ring of the (CHROM) through R 1 .

Inventors

  • 👤 Edward W. Kluger
  • 👤 Patrick D. Moore
  • 👤 Judy A. Wagner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 19:41
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/16; C09D11/17; C09B; C09B69/00

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 241 words
A washable, aqueous ink composition for a color marking pen which comprises an ink composition having a viscosity of from about 1.0 to about 6.0 centipoises and from about 10% to about 50% by weight of one or more polymeric colorants of the formula: [(X).sub.d --(CHROM)--{[R.sub.1 (RO).sub.a Y].sub.b }.sub.c ]X.sub.d --(CHROM)--{R.sub.1 [(RO).sub.a --Y].sub.b }.sub.c wherein: X is a polar group selected from sulfonic acids, sulfonic acid salts, sulfonamides, sulfonates, carboxylic acids, carboxylic acid salts, carboxylic acid amides, carboxylic aldehydes, ureas, thioureas, nitro groups, hydroxy groups, polyethers, and hydroxyalkylethers; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons, or mixtures thereof; Y is selected from H, alkanoyl, aroyl, alkoxycarbonyl, unsubstituted or substituted carbamoyl, diacetate, methyl or --CH 2 CH(R 2 )--X; R 1 is selected from nitrogen, oxygen, sulfur, or a sulfurcontaining divalent linking group; R 2 is hydrogen or a lower alkyl group containing one to about five carbon atoms; a is an integer of from 6 to about 40; b and c are each independently selected from one or two; d is an integer of from one to four; the product of (a) (b) (c) is an integer of from 6 to about 40; and CHROM is a chromophore selected from nitro, nitroso, monoazo, disazo and trisazo, diarylmethane, triarylmethane, xanthane, acridine, methine, thiazole, indamine, azine, oxazine, or anthraquinone, wherein the (RO) a moiety is bonded to a carbocyclic aromatic ring of the (CHROM) through R 1 .
Claim 2
Dependent Claim 241 words
A washable, aqueous ink composition for a color marking pen which comprises an ink composition having a viscosity of from about 1.0 to about 6.0 centipoises and from about 10% to about 50% by weight of one or more polymeric colorants of the formula: [(X).sub.d --(CHROM)--{[R.sub.1 (RO).sub.a Y].sub.b }.sub.c ]X.sub.d --(CHROM)--{R.sub.1 [(RO).sub.a --Y].sub.b }.sub.c wherein: X is a polar group selected from sulfonic acids, sulfonic acid salts, sulfonamides, sulfonates, carboxylic acids, carboxylic acid salts, carboxylic acid amides, carboxylic aldehydes, ureas, thioureas, nitro groups, hydroxy groups, polyethers, and hydroxyalkylethers; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons, or mixtures thereof; Y is selected from H, alkanoyl, aroyl, alkoxycarbonyl, unsubstituted or substituted carbamoyl, diacetate, methyl or --CH 2 CH(R 2 )--X; R 1 is selected from nitrogen, oxygen, sulfur, or a sulfurcontaining divalent linking group; R 2 is hydrogen or a lower alkyl group containing one to about five carbon atoms; a is an integer of from 6 to about 40; b and c are each independently selected from one or two; d is an integer of from one to four; the product of (a) (b) (c) is an integer of from 6 to about 40; and CHROM is a chromophore selected from nitro, nitroso, monoazo, disazo and trisazo, diarylmethane, triarylmethane, xanthane, acridine, methine, thiazole, indamine, azine, oxazine, or anthraquinone, wherein the (RO) a moiety is bonded to a carbocyclic aromatic ring of the (CHROM) through R 1 .
Claim 3
Dependent Claim 79 words
The composition as defined in claim 1 of the formula: ##STR18## wherein R 3 , R 4 or R 5 are selected from hydrogen, lower alkyl, lower alkoxy, halogen, trifluoroalkyl, SO 3 Z, SO 2 N(R 6 )R 7 , and CON(R 6 )R 7 ; R 6 and R 7 are hydrogen, or alkyl; Z is hydrogen or a cation selected from sodium, potassium, or ammonium, and (a) is an integer of from about 5 to about 15.
Claim 4
Dependent Claim 64 words
The composition as defined in claim 1 of the formula: ##STR19## wherein R 8 is selected from H, lower alkyl, lower alkoxy, halogen, or trifluoroalkyl; R 9 is selected from alkyl, alkoxy, or halogen, and f is zero or one; Z is H or a cation selected from Na, K, or ammonium; and (a) is an integer of from about 3 to about 10.
Claim 5
Dependent Claim 93 words
The composition as defined in claim 1 of the formula: ##STR20## wherein R 3 , R 4 and R 5 are selected from H. lower alkyl, lower alkoxy, halogen, trifluoroalkyl, SO 3 Z, SO 2 N(R 6 )R 7 , CON(R 6 )R 7 wherein R 6 and R 7 are H or alkyl, and Z is H or a cation selected from Na, K, or ammonium; R 10 and R 11 are selected from hydroxyalkoxy, hydroxypolyalkyleneoxy, alkoxyalkylene, alkoxypolyalkyleneoxy or alkyl; and (a) in an integer of from about 10 to about 20.
Claim 6
Dependent Claim 88 words
The composition as defined in claim 1 of the formula: ##STR21## wherein R 3 , R 4 and R 5 are selected from H, lower alkyl, lower alkoxy, halogen, trifluoroalkyl, SO 3 Z, SO 2 N(R 6 )R 7 , CON(R 6 )R 7 wherein R 6 and R 7 are H or alkyl, and Z is H or a cation selected from Na, K or ammonium; g is an integer equal to one or two, and (a) is an integer of from about 5 to about 10.
Claim 7
Dependent Claim 92 words
The composition as defined in claim 1 of the formula: ##STR22## wherein R 3 , R 4 and R 5 are selected from H, lower alkyl, lower alkoxy, halogen, trifluoroalkyl, SO 3 Z, SO 2 N(R 6 )R 7 , CON(R 6 )R 7 wherein R 6 and R 7 are H or alkyl, and Z is H or a cation selected from Na, K, or ammonium; R 12 is an alkylene group containing from one to about five carbons, and (a) is an integer of from about 5 to about 10.
Claim 8
Dependent Claim 90 words
The composition as defined in claim 1 of the formula: ##STR23## wherein R 3 is selected from H, lower alkyl, lower alkoxy, halogen, trifluoroalkyl, SO 3 Z, SO 2 N(R 6 )R 7 , CON(R 6 )R 7 wherein R 6 and R 7 are H or alkyl, and Z is H or a cation selected from Na, K, or ammonium; and R 13 is cyano, R 14 NHCO, or COOZ, and R 14 is selected from hydrogen, lower alkyl containing one to five carbons, hydroxyalkylene, hydroxyl-polyalkyleneoxy, alkoxyalkylene, or alkoxypolyalkyleneoxy.
Claim 9
Dependent Claim 80 words
The composition as defined in claim 1 wherein CHROM is: ##STR24## wherein R 15 is COOZ; R 3 and R 4 are selected from H, lower alkyl, lower alkoxy, halogen, trifluoroalkyl, SO 3 Z, SO 2 N(R 6 )R 7 , CON(R 6 )R 7 wherein R 6 and R 7 are H or alkyl, and Z is H or a cation selected from Na, K, or ammonium; and (a) is an integer of from about 5 to about 10.
Claim 10
Dependent Claim 42 words
The composition as defined in claim 1 of the formula: ##STR25## wherein Z is H or a cation selected from Na, K, or ammonium; (a) is an integer of from about 5 to about 10. and R 16 is H or OH.
Claim 11
Dependent Claim 31 words
The washable ink composition of claim 1 wherein the polymeric colorant containing a polar chromophore has incorporated therein from about 40 percent to about 85 percent by weight of poly(alkylene oxide).
Claim 12
Dependent Claim 34 words
The washable ink composition of claim 1 wherein the polymeric colorant in the ink composition has incorporated therein from about 5 percent by weight to about 40 percent by weight of poly(alkylene oxide) units.
Claim 13
Dependent Claim 16 words
The washable ink composition of claim 1 wherein the poly(alkylene oxide) is derived from ethylene oxide.
Claim 14
Dependent Claim 21 words
The washable, aqueous ink composition for a color pen of claim 1 which comprises nib, felt, wick, and recording type markers.
Claim 15
Dependent Claim 20 words
The washable ink composition of claim 1 containing from about 5 percent to about 20 percent by weight of humectant.
Claim 16
Dependent Claim 20 words
The washable ink composition of claim 1 containing from about 0.02 percent to about 0.5 percent by weight of biocide.
Claim 17
Dependent Claim 21 words
The washable ink composition of claim 1 containing from about 0.1 percent to about 0.5 percent by weight of chelating agent.
Claim 18
Dependent Claim 17 words
The washable ink composition of claim 1 wherein the pH is maintained from 6.0 to about 7.5.
Claim 19
Dependent Claim 26 words
The washable ink composition of claim 1 wherein the residual colorant fabric staining is rated at a numerical value of zero to ten delta E*ab units.
Claim 20
Dependent Claim 21 words
The washable ink composition of claim 1 wherein the residual colorant skin staining is rated at zero to about 1.5 units.
Claim 21
Dependent Claim 16 words
The washable ink composition of claim 1 wherein Y is selected from H, diacetate and methyl.

References Cited (Backward Citations)

US3157633A Cited
US4167510A Cited
US4284729A Cited
US4508570A Cited
US4703113A Cited
US4738721A Cited
US4908062A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-08-26 1995-02-25 1995-08-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-08-26 1999-02-25 1999-08-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-08-26 2003-02-25 2003-08-27 $7700.00 Window Closed / Lapsed

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