US5951749A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Water-based pigmented inks
Assignee: 3M Innovative Properties Co
•
Filing: 1996-05-16
•
Granted: 1999-09-14
•
Expires: 2016-05-16
Abstract
Abstract Water-based pigmented inks are disclosed. Such inks are formed from water-based dispersions of pigment particles having novel dispersants therein. The dispersions are formed from the reaction product of an amino acid compound with a nitrogen reactive compound with subsequent hydrolysis providing the capability of the dispersant to hydrophobically interact with the pigment particles. The resultinginks are well-suited for use in ink jet and other printing applications.
Inventors
- 👤 Larry R. Krepski
- 👤 Prabhakara S. Rao
- 👤 Terrance P. Smith
- 👤 Kenneth D. Wilson
- 👤 Richard J. Kuo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:35
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/30; C09D11/32; C09D11/324; C09D11/326
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
118 words
A water-based pigmented ink which comprises a suspension of: a) pigment particles, and b) a dispersant of a formula of ##STR7## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 2
Dependent Claim
118 words
A water-based pigmented ink which comprises a suspension of: a) pigment particles, and b) a dispersant of a formula of ##STR7## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 3
Dependent Claim
43 words
The water-based pigmented ink of claim 1, wherein the dispersant is a reaction product of an amino acid compound and a nitrogen reactive compound, according to an equation of ##STR8## wherein R 1 and R 2 are independently, alkyl, aryl, or aralkyl groups.
Claim 4
Dependent Claim
16 words
The water-based pigmented ink of claim 2, wherein the amino acid compound comprises an aspartic ester.
Claim 5
Dependent Claim
18 words
The water-based pigmented ink of claim 3, wherein the aspartic ester comprises a mono- or bis- aspartic ester.
Claim 6
Dependent Claim
131 words
The water-based pigmented ink of claim 1, wherein R 5 is selected from the group consisting of R 6 CO, wherein R 6 is an alkyl, aryl, or aralkyl group; R 7 R 8 NCO, wherein R 7 or R 8 independently is an alkyl, aryl, or aralkyl group; R 9 R 10 NSO 2 where R 9 or R 10 independently is an alkyl, aryl, or aralkyl group; R 11 , which is an alkyl or aralkyl group; R 12 CH(OH)CH 2 wherein R 12 is an alkyl, aryl, or aralkyl group; R 13 NHCY, wherein Y is O or S, respectively, and wherein R 13 can be an alkyl, aryl, or aralkyl group; and R 14 SO 2 , wherein R 14 is an alkyl, aryl, or aralkyl group.
Claim 7
Dependent Claim
36 words
The water-based pigmented ink of claim 5, wherein, when R 5 is R 13 NHCY, and when Y is S or O, a cyclization reaction according to a equation of ##STR9## results in a hydantoin-based dispertant.
Claim 8
Dependent Claim
63 words
The water-based pigmented ink of claim 2, wherein the reaction product of the equation is reacted with a hydroxide selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, a tetrasubstituted ammonium hydroxide, and combinations thereof, in order to cause hydrolysis of one or more of the ester groups CO 2 R 1 and CO 2 R 2 .
Claim 9
Dependent Claim
12 words
The water-based pigmented ink of claim 1, which further comprises a surfactant.
Claim 10
Dependent Claim
13 words
The water-based pigmented ink of claim 1, which further comprises an alcoholic polyol.
Claim 11
Dependent Claim
15 words
The water-based pigmented ink of claim 9, wherein the alcoholic polyol comprises an ethylene glycol.
Claim 12
Dependent Claim
23 words
The water-based pigmented ink of claim 1, wherein the pigment is selected from the group consisting of black, yellow, magenta, and cyan pigments.
Claim 13
Dependent Claim
16 words
The water-based pigmented ink of claim 11, wherein the black pigment comprises a carbon black pigment.
Claim 14
Dependent Claim
17 words
The water-based pigmented ink of claim 11, wherein the yellow pigment comprises a nickel azo yellow pigment.
Claim 15
Dependent Claim
16 words
The water-based pigmented ink of claim 11, wherein the magenta pigment comprises a quinacridone magenta pigment.
Claim 16
Dependent Claim
16 words
The water-based pigmented ink of claim 11, wherein the cyan pigment comprises a copper phthalocyanine pigment.
Claim 17
Dependent Claim
21 words
The water-based pigmented ink of claim 1 wherein the dispersant interacts hydrophobically with the pigment particles and interacts hydrophilically with water.
Claim 18
Independent Claim
127 words
A method of using a dispersant of a formula of ##STR10## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium, comprising the steps of: (a) mixing the dispersant with an ink; and (b) depositing the ink on a substrate.
Claim 19
Independent Claim
127 words
A method of using a dispersant of a formula of ##STR10## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium, comprising the steps of: (a) mixing the dispersant with an ink; and (b) depositing the ink on a substrate.
Claim 20
Independent Claim
133 words
A method of preparing a water-based pigmented ink, comprising the step of mixing pigment particles with dispersant of a formula of ##STR11## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium; wherein the dispersant interacts hydrophobically with the pigment particles and interacts hydrophilically with water.
Claim 21
Independent Claim
133 words
A method of preparing a water-based pigmented ink, comprising the step of mixing pigment particles with dispersant of a formula of ##STR11## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium; wherein the dispersant interacts hydrophobically with the pigment particles and interacts hydrophilically with water.
Claim 22
Independent Claim
129 words
A method of using a water-based pigmented ink, comprising the step of depositing the ink on a substrate, wherein in the ink comprises pigment particles and dispersant of a formula of ##STR12## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 23
Independent Claim
129 words
A method of using a water-based pigmented ink, comprising the step of depositing the ink on a substrate, wherein in the ink comprises pigment particles and dispersant of a formula of ##STR12## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 24
Dependent Claim
109 words
An ink comprising: pigment particles and dispersant of a formula of ##STR13## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 25
Dependent Claim
109 words
An ink comprising: pigment particles and dispersant of a formula of ##STR13## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagents, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 26
Dependent Claim
127 words
A combination of pigment and dispersant in hydrophobic interaction, comprising: pigment particles and dispersant hydrophobically interacting with pigment particles, wherein the dispersant comprises a compound of a formula of ##STR14## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagants, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 27
Dependent Claim
127 words
A combination of pigment and dispersant in hydrophobic interaction, comprising: pigment particles and dispersant hydrophobically interacting with pigment particles, wherein the dispersant comprises a compound of a formula of ##STR14## wherein R is an alkyl, aryl, or aralkyl group obtained by the removal of primary amino groups from alkyl, aryl, or aralkyl amines; m=1 to 6; R 3 and R 4 are hydrogen or lower alkyl; R 5 is the residue of the nitrogen reactive compound selected from the group consisting of acylating reagents, carbamoyl halides, sulfamoyl halides, alkylating reagents, alkylating (epoxide) reagants, iso(thio)cyanates, sulfonating reagents; wherein R 20 and R 21 are independently, alkyl, aryl, or aralkyl groups, or a cation selected from the group consisting of a proton, lithium, sodium, potassium, ammonium, or tetraalkyl ammonium.
Claim 28
Dependent Claim
21 words
The combination of claim 21, wherein pigment particles are selected from the group consisting of black, yellow, magenta, and cyan pigments.
References Cited (Backward Citations)
US4597794A
Cited
US4639286A
Cited
EP0105665B1
Cited
US4485236A
Cited
US4705889A
Cited
EP0195328B1
Cited
US5236741A
Cited
US5125968A
Cited
US5085698A
Cited
US5284512A
Cited
US5243012A
Cited
US5840106A
Cited
US5854308A
Cited
US5725647A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2002-09-13 | 2003-03-15 | 2003-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-09-13 | 2007-03-15 | 2007-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-09-13 | 2011-03-15 | 2011-09-14 | $7700.00 | Window Closed / Lapsed |