US5364462A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Waterfast inks
Assignee: Graphic Utilities Inc
•
Filing: 1993-11-12
•
Granted: 1994-11-15
•
Expires: 2013-11-12
Abstract
Abstract The present invention provides improved dye based ink solutions for use in ink jet printing. In one embodiment of the invention, an aqueous ink with improved water solubility and waterfastness is provided that includes a dye component and a hydroxyethylated polyethylene imine polymer, wherein the hydroxyethylated polyethylene imine polymer has incorporated therein approximately 10 to 55 percent hydroxyethyl groups by weight. Alternative embodiments of the invention include the use of hydroxypropylated polyethylene imine polymers or epichlorohydrin-modified polyethylene imine polymers. In addition, aprotic solvents such as dimethyl sulfoxide and tetramethylene sulfone may be added to improve the solubility and stability of the dye solution, and humectants such as 2-pyrrolidone may be added. According to the methods of the invention, an ink with improved stability, jetting characteristics, solubility and waterfastness may be provided.
Inventors
- 👤 Richard Crystal
- 👤 Raymond Geffre
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 16:21
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/30
Claims Analysis
Total Claims: 65
Claim 1
Independent Claim
87 words
A dye solution suitable for ink let printing comprising: a dye component; and a polyethylene imine polymer having an average molecular weight of less than approximately 3000 selected from the group consisting of (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight, (b) a hydroxypropylated polyethylene imine polymer formed from an polyethylene imine polymer having an average molecular weight less then 1000, (c) an epichlorohydrin-modified polyethylene imine polymer, (d) a hydroxybutylated polyethylene imine polymer and (e) a glycidol-modified polyethylene imine polymer.
Claim 2
Dependent Claim
87 words
A dye solution suitable for ink let printing comprising: a dye component; and a polyethylene imine polymer having an average molecular weight of less than approximately 3000 selected from the group consisting of (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight, (b) a hydroxypropylated polyethylene imine polymer formed from an polyethylene imine polymer having an average molecular weight less then 1000, (c) an epichlorohydrin-modified polyethylene imine polymer, (d) a hydroxybutylated polyethylene imine polymer and (e) a glycidol-modified polyethylene imine polymer.
Claim 3
Dependent Claim
23 words
A dye solution according to claim 1, wherein the dye component is selected from the group consisting of acid, direct and reactive dyes.
Claim 4
Dependent Claim
41 words
A dye solution according to claim 2, wherein the dye component is selected from the group consisting of Direct Black 17, Direct Black 19, Direct Black 154, Direct Black 163, Direct Black 168, Black SP liquid and Basacid Black X-34 liquid.
Claim 5
Dependent Claim
34 words
A dye solution according to claim 3, wherein the solution is aqueous and buffered with a base selected from the group consisting of triethanolamine, aqueous sodium hydroxide, aqueous lithium hydroxide and aqueous potassium hydroxide.
Claim 6
Dependent Claim
27 words
A dye solution according to claim 4, wherein the buffer is aqueous sodium hydroxide, and wherein the pH of the solution is adjusted to approximately pH 10.
Claim 7
Dependent Claim
27 words
A dye solution according to claim 4, wherein the buffer is aqueous sodium hydroxide, and wherein the pH of the solution is adjusted to approximately pH 12.
Claim 8
Dependent Claim
11 words
A dye solution according to claim 2, further comprising a humectant.
Claim 9
Dependent Claim
11 words
A dye solution according to claim 4, further comprising a humectant.
Claim 10
Dependent Claim
20 words
A dye solution according to claim 7, wherein the humectant is selected from the group consisting of n-methyl-pyrrolidone and 2-pyrrolidone.
Claim 11
Dependent Claim
20 words
A dye solution according to claim 8, wherein the humectant is selected from the group consisting of n-methyl-pyrrolidone and 2-pyrrolidone.
Claim 12
Dependent Claim
26 words
A dye solution according to claim 9, wherein the humectant is 2-pyrrolidone and wherein the concentration of 2-pyrrolidone is approximately 1 to 10 percent by weight.
Claim 13
Dependent Claim
26 words
A dye solution according to claim 10, wherein the humectant is 2-pyrrolidone and wherein the concentration of 2-pyrrolidone is approximately 1 to 10 percent by weight.
Claim 14
Dependent Claim
12 words
A dye solution according to claim 2, further comprising an aprotic solvent.
Claim 15
Dependent Claim
23 words
A dye solution according to claim 13, wherein the aprotic solvent is selected from the group consisting of dimethyl formamide and hexamethyl phosphorotriamide.
Claim 16
Dependent Claim
32 words
A dye solution according to claim 13, wherein the aprotic solvent is a sulfur containing composition selected from the group consisting of tetramethylene sulfone, dimethyl sulfoxide, sulfoxamide, butadiene sulfone and dimethyl thiophene.
Claim 17
Dependent Claim
12 words
A dye solution according to claim 4, further comprising an aprotic solvent.
Claim 18
Dependent Claim
23 words
A dye solution according to claim 16, wherein the aprotic solvent is selected from the group consisting of dimethyl formamide and hexamethyl phosphorotriamide.
Claim 19
Dependent Claim
32 words
A dye solution according to claim 16, wherein the aprotic solvent is a sulfur containing composition selected from the group consisting of tetramethylene sulfone, dimethyl sulfoxide, sulfoxamide, butadiene sulfone and dimethyl thiophene.
Claim 20
Dependent Claim
12 words
A dye solution according to claim 9, further comprising an aprotic solvent.
Claim 21
Dependent Claim
22 words
A dye solution according to claim 19, wherein the aprotic solvent is selected from the group consisting dimethyl formamide and hexamethyl phosphorotriamide.
Claim 22
Dependent Claim
32 words
A dye solution according to claim 19, wherein the aprotic solvent is a sulfur containing composition selected from the group consisting of tetramethylene sulfone, dimethyl sulfoxide, sulfoxamide, butadiene sulfone and dimethyl thiophene.
Claim 23
Dependent Claim
36 words
A dye solution according to claim 15, wherein the sulfur containing composition is tetramethylene sulfone; and wherein the tetramethylene sulfone is included in the solution at a concentration of approximately 1 to 15 percent by weight.
Claim 24
Dependent Claim
36 words
A dye solution according to claim 18, wherein the sulfur containing composition is tetramethylene sulfone; and wherein the tetramethylene sulfone is included in the solution at a concentration of approximately 1 to 15 percent by weight.
Claim 25
Dependent Claim
36 words
A dye solution according to claim 21, wherein the sulfur containing composition is tetramethylene sulfone; and wherein the tetramethylene sulfone is included in the solution at a concentration of approximately 1 to 15 percent by weight.
Claim 26
Dependent Claim
11 words
A dye solution according to claim 1, further comprising a biocide.
Claim 27
Dependent Claim
11 words
A dye solution according to claim 1, further comprising a glycol.
Claim 28
Dependent Claim
13 words
A dye solution according to claim 26, wherein the glycol is neopentyl glycol.
Claim 29
Dependent Claim
22 words
A dye solution according to claim 4, wherein the base is added to the solution prior to the addition of the dye.
Claim 30
Independent Claim
96 words
A method for the production of a dye solution suitable for ink jet printing comprising: (i) obtaining a dye component and a polyethylene imine polymer having an average molecular weight of less than approximately 3000 selected from the group consisting of (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight, (b) a hydroxypropylated polyethylene imine polymer formed from an polyethylene imine polymer having an average molecular weight less then 1000, (c) an epichlorohydrin -modified polyethylene imine polymer, (d) a hydroxybutylated polyethylene imine polymer and (e) a glycidol-modified polyethylene imine polymer.
Claim 31
Independent Claim
96 words
A method for the production of a dye solution suitable for ink jet printing comprising: (i) obtaining a dye component and a polyethylene imine polymer having an average molecular weight of less than approximately 3000 selected from the group consisting of (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight, (b) a hydroxypropylated polyethylene imine polymer formed from an polyethylene imine polymer having an average molecular weight less then 1000, (c) an epichlorohydrin -modified polyethylene imine polymer, (d) a hydroxybutylated polyethylene imine polymer and (e) a glycidol-modified polyethylene imine polymer.
Claim 32
Dependent Claim
22 words
A method according to claim 29, wherein the dye component is selected from the group consisting of acid, direct and reactive dyes.
Claim 33
Dependent Claim
40 words
A method according to claim 30, wherein the dye component is selected from the group consisting of Direct Black 17, Direct Black 19, Direct Black 154, Direct Black 163, Direct Black 168, Black SP liquid and Basacid Black X-34 liquid.
Claim 34
Dependent Claim
37 words
A method according to claim 30, further comprising, adding water to the solution and buffering the solution with a base selected from the group consisting of triethanolamine, aqueous sodium hydroxide, aqueous lithium hydroxide and aqueous potassium hydroxide.
Claim 35
Dependent Claim
26 words
A method according to claim 32, wherein the buffer is aqueous sodium hydroxide, and wherein the pH of the solution is adjusted to approximately pH 10.
Claim 36
Dependent Claim
26 words
A method according to claim 32, wherein the buffer is aqueous sodium hydroxide, and wherein the pH of the solution is adjusted to approximately pH 12.
Claim 37
Dependent Claim
11 words
A method according to claim 30, further comprising adding a humectant.
Claim 38
Dependent Claim
11 words
A method according to claim 32, further comprising adding a humectant.
Claim 39
Dependent Claim
19 words
A method according to claim 35, wherein the humectant is selected from the group consisting of n-methyl-pyrrolidone and 2-pyrrolidone.
Claim 40
Dependent Claim
19 words
A method according to claim 36, wherein the humectant is selected from the group consisting of n-methyl-pyrrolidone and 2-pyrrolidone.
Claim 41
Dependent Claim
25 words
A method according to claim 37, wherein the humectant is 2-pyrrolidone and wherein the concentration of 2-pyrrolidone is approximately 1 to 10 percent by weight.
Claim 42
Dependent Claim
25 words
A method according to claim 38, wherein the humectant is 2-pyrrolidone and wherein the concentration of 2-pyrrolidone is approximately 1 to 10 percent by weight.
Claim 43
Dependent Claim
12 words
A method according to claim 30, further comprising adding an aprotic solvent.
Claim 44
Dependent Claim
22 words
A method according to claim 41, wherein the aprotic solvent is selected from the group consisting of dimethyl formamide and hexamethyl phosphorotriamide.
Claim 45
Dependent Claim
31 words
A method according to claim 41, wherein the aprotic solvent is a sulfur containing composition selected from the group consisting of tetramethylene sulfone, dimethyl sulfoxide, sulfoxamide, butadiene sulfone and dimethyl thiophene.
Claim 46
Dependent Claim
12 words
A method according to claim 32, further comprising adding an aprotic solvent.
Claim 47
Dependent Claim
22 words
A method according to claim 44, wherein the aprotic solvent is selected from the group consisting of dimethyl formamide and hexamethyl phosphorotriamide.
Claim 48
Dependent Claim
31 words
A method according to claim 44, wherein the aprotic solvent is a sulfur containing composition selected from the group consisting of tetramethylene sulfone, dimethyl sulfoxide, sulfoxamide, butadiene sulfone and dimethyl thiophene.
Claim 49
Dependent Claim
12 words
A method according to claim 37, further comprising adding an aprotic solvent.
Claim 50
Dependent Claim
22 words
A method according to claim 37, wherein the aprotic solvent is selected from the group consisting of dimethyl formamide and hexamethyl phosphorotriamide.
Claim 51
Dependent Claim
31 words
A method according to claim 47, wherein the aprotic solvent is a sulfur containing composition selected from the group consisting of tetramethylene sulfone, dimethyl sulfoxide, sulfoxamide, butadiene sulfone and dimethyl thiophene.
Claim 52
Dependent Claim
35 words
A method according to claim 43, wherein the sulfur containing composition is tetramethylene sulfone; and wherein the tetramethylene sulfone is included in the solution at a concentration of approximately 1 to 15 percent by weight.
Claim 53
Dependent Claim
35 words
A method according to claim 46, wherein the sulfur containing composition is tetramethylene sulfone; and wherein the tetramethylene sulfone is included in the solution at a concentration of approximately 1 to 15 percent by weight.
Claim 54
Dependent Claim
35 words
A method according to claim 49, wherein the sulfur containing composition is tetramethylene sulfone; and wherein the tetramethylene sulfone is included in the solution at a concentration of approximately 1 to 15 percent by weight.
Claim 55
Dependent Claim
11 words
A method according to claim 29, further comprising adding a biocide.
Claim 56
Dependent Claim
11 words
A method according to claim 29, further comprising adding a glycol.
Claim 57
Dependent Claim
12 words
A method according to claim 54, wherein the glycol is neopentyl glycol.
Claim 58
Dependent Claim
30 words
A method according to claim 32, wherein the step of adding the base to the solution is carried out prior the step of adding the dye component to the solution.
Claim 59
Dependent Claim
13 words
A method according to claim 56 wherein the buffer is aqueous sodium hydroxide.
Claim 60
Dependent Claim
63 words
A dye solution suitable for ink jet printing comprising: a dye component; and a polyethylene imine polymer selected from the group consisting of (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight; (b) a hydroxypropylated polyethylene imine polymer; (c) an epichlorohydrin-modified polyethylene imine polymer; (d) a hydroxybutylated polyethylene imine polymer; and (e) a glycidol-modified polyethylene imine polymer.
Claim 61
Dependent Claim
63 words
A dye solution suitable for ink jet printing comprising: a dye component; and a polyethylene imine polymer selected from the group consisting of (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight; (b) a hydroxypropylated polyethylene imine polymer; (c) an epichlorohydrin-modified polyethylene imine polymer; (d) a hydroxybutylated polyethylene imine polymer; and (e) a glycidol-modified polyethylene imine polymer.
Claim 62
Independent Claim
71 words
A method for the production of a dye solution suitable for ink jet printing comprising: (i) obtaining a dye component and a polyethylene imine polymer selected from the group consisting of: (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight; (b) a hydroxypropylated polyethylene imine polymer; (c) an epichlorohydrin-modified polyethylene imine polymer; (d) a hydroxybutylated polyethylene imine polymer; and (e) a glycidol-modified polyethylene imine polymer.
Claim 63
Independent Claim
71 words
A method for the production of a dye solution suitable for ink jet printing comprising: (i) obtaining a dye component and a polyethylene imine polymer selected from the group consisting of: (a) a hydroxyethylated polyethylene imine polymer having incorporated therein approximately 10-55% hydroxyethyl groups by weight; (b) a hydroxypropylated polyethylene imine polymer; (c) an epichlorohydrin-modified polyethylene imine polymer; (d) a hydroxybutylated polyethylene imine polymer; and (e) a glycidol-modified polyethylene imine polymer.
Claim 64
Dependent Claim
31 words
A dye solution according to claim 58, wherein (b) the hydroxypropylated polyethylene imine polymer in (b) is formed from a polyethylene imine polymer having an average molecular weight less then 1000.
Claim 65
Dependent Claim
29 words
A method according to claim 59, wherein the hydroxypropylated polyethylene imine polymer in (b) is formed from a polyethylene imine polymer having an average molecular weight less then 1000.
References Cited (Backward Citations)
US3753931A
Cited
US4076497A
Cited
US4299630A
Cited
US4155768A
Cited
US4150997A
Cited
US4520143A
Cited
US4167393A
Cited
US4238234A
Cited
US4197135A
Cited
US4267088A
Cited
US4383859A
Cited
US4793264A
Cited
US4585484A
Cited
US4588413A
Cited
US4627875A
Cited
US4601756A
Cited
US4791165A
Cited
US4659382A
Cited
US4664708A
Cited
US4789400A
Cited
US4836851A
Cited
US5017224A
Cited
US5019164A
Cited
US5017644A
Cited
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