Source: http://www.google.com/patents/US5127946?dq=U.S.+patent+number+7,325,728&ei=Y93TTteOAe702wW6uqi1BQ
Timestamp: 2016-09-26 02:07:21
Document Index: 59037380

Matched Legal Cases: ['arts2', 'arts3', 'arts4', 'arts5', 'arts6', 'arts7', 'arts8', 'arts9', 'arts10', 'arts11', 'arts12', 'arts14', 'arts15', 'arts16', 'arts17']

Patent US5127946 - Ink, and ink-jet recording method and apparatus employing the ink - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsProvided is an ink containing a recording agent and a liquid medium for dissolution or dispersion thereof, said ink comprising, as the recording agent, a compound represented by the general formula (A) ##STR1## where n is 0 or 1; R1, R2, and R3 are respectively a substituent selected from the group consisting...http://www.google.com/patents/US5127946?utm_source=gb-gplus-sharePatent US5127946 - Ink, and ink-jet recording method and apparatus employing the inkAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS5127946 APublication typeGrantApplication numberUS 07/644,605Publication dateJul 7, 1992Filing dateJan 23, 1991Priority dateJan 30, 1990Fee statusPaidAlso published asDE69102441D1, DE69102441T2, EP0440084A1, EP0440084B1Publication number07644605, 644605, US 5127946 A, US 5127946A, US-A-5127946, US5127946 A, US5127946AInventorsTsuyoshi Eida, Takao Yamamoto, Mayumi YamamotoOriginal AssigneeCanon Kabushiki KaishaExport CitationBiBTeX, EndNote, RefManPatent Citations (26), Referenced by (24), Classifications (13), Legal Events (5) External Links: USPTO, USPTO Assignment, EspacenetInk, and ink-jet recording method and apparatus employing the ink
US 5127946 AAbstract
1. An ink containing a recording agent and a liquid medium for dissolution or dispersion thereof, said ink comprising, as the recording agent, a compound represented by the general formula (A) ##STR6## where n is 0 or 1; R1, R2, and R3 are respectively a substituent selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, amino, acetylamino, and sulfonic acid; and M is an alkali metal, ammonium, or an organic ammonium.
2. The ink of claim 1, wherein the compound represented by the general formula (A) is at least one selected from the following compounds of from No. 1 to No. 12: ##STR7##
3. The ink of claim 1, wherein pH of the ink is within the range of from 4 to 10.
4. The ink of claim 1, wherein said recording agent is contained in an amount within the range of from 0.1 to 15% by weight of the total weight of the ink.
5. The ink of claim 1, wherein the liquid medium comprises a mixed solvent of water and a water-soluble organic solvent.
6. The ink of claim 5, wherein the water is contained in an amount within the range of from 10 to 97.5% by weight of the total weight of the ink.
7. The ink of claim 5, wherein the water-soluble organic solvent is contained in an amount within the range of from 2 to 80% by weight of the total weight of the ink.
8. In an ink-jet recording method for recording on a recording medium with droplets of ink, the improvement comprising employing a liquid ink composition containing at least one compound represented by the general formula (A) ##STR8## where n is 0 or 1; R1, R2, and R3 are respectively a substituent selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, amino, acetylamino, and sulfonic acid; and M is an alkali metal, ammonium, or an organic ammonium.
9. In the ink-jet recording method of claim 8, wherein the compound represented by the general formula (A) is at least one selected from the following compounds of from No. 1 to No. 12: ##STR9##
10. In the ink-jet recording method of claim 8, wherein pH of the ink is within the range of from 4 to 10.
11. In the ink-jet recording method of claim 8, wherein the compound represented by the general formula (A) is contained in an amount within the range of from 0.1 to 15% by weight of the total weight of the ink.
12. In the ink-jet recording method of claim 8, wherein the ink further comprises a mixed solvent of water and a water-soluble organic solvent.
13. In the ink-jet recording method of claim 12, wherein the water is contained in an amount within the range of from 10 to 97.5% by weight of the total weight of the ink.
14. In the ink-jet recording method of claim 12, wherein the water-soluble organic solvent is contained in an amount within the range of from 2 to 80% of the total weight of the ink.
15. In the ink-jet recording method of claim 8, wherein the recording medium is non-coated paper or coated paper.
16. In the ink-jet recording method of claim 8, wherein the ink is ejected by action of thermal energy on the ink.
17. A recording unit having an ink container portion for holding an ink and a head for ejecting the ink in droplets, said ink being a liquid composition containing at least one compound represented by the general formula (A) ##STR10## where n is 0 or 1; R1, R2, and R3 are respectively a substituent selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, amino, acetylamino, and sulfonic acid; and M is an alkali metal, ammonium, or an organic ammonium.
18. The recording unit of claim 17, wherein the compound represented by the general formula (A) is at least one selected from the following compounds of from No. 1 to No. 12: ##STR11##
19. The recording unit of claim 17, wherein pH of the ink is within the range of from 4 to 10.
20. The recording unit of claim 17, wherein the compound represented by the general formula (A) is contained in an amount within the range of from 0.1 to 15% by weight of the total weight of the ink.
21. The recording unit of claim 17, wherein the ink further comprises a mixed solvent of water and a water-soluble organic solvent.
22. The recording unit of claim 21, wherein the water is contained in an amount within the range of from 10 to 97.5% by weight of the total weight of the ink.
23. The recording unit of claim 21, wherein the water-soluble organic solvent is contained in an amount within the range of from 2 to 80% of the total weight of the ink.
24. The recording unit of claim 17, wherein the head ejects ink droplets by action of thermal energy on the ink.
25. The recording unit of claim 17, wherein the ink container portion comprises an ink absorption member.
26. The recording unit of claim 25, wherein the ink absorption member is formed from polyurethane.
27. An ink cartridge having an ink container portion for holding an ink, said ink being a liquid composition containing at least one compound represented by the general formula (A) ##STR12## where n is 0 or 1; R1, R2, and R3 are respectively a substituent selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, amino, acetylamino, and sulfonic acid; and M is an alkali metal, ammonium, or an organic ammonium.
28. The ink cartridge of claim 27, wherein the compound represented by the general formula (A) is at least one selected from the following compounds of from No. 1 to No. 12: ##STR13##
29. The ink cartridge of claim 27, wherein pH of the ink is within the range of from 4 to 10.
30. The ink cartridge of claim 27, wherein the compound represented by the general formula (A) is contained in an amount within the range of from 0.1 to 15% by weight of the total weight of the ink.
31. The ink cartridge of claim 27, wherein the ink further comprises a mixed solvent of water and a water-soluble organic solvent.
32. The ink cartridge of claim 31, wherein the water is contained in an amount within the range of from 10 to 97.5% by weight of the total weight of the ink.
33. The ink cartridge of claim 31, wherein the water-soluble organic solvent is contained in an amount within the range of from 2 to 80% of the total weight of the ink.
34. The ink cartridge of claim 27, wherein the ink container portion is of a bag structure.
35. The ink cartridge of claim 27, wherein the ink container portion has a liquid-contact face formed of polyolefin.
and so forth. Furthermore, in an ink-jet recording system, utilizing thermal energy, the property below is required in addition to the above requirements:
3'-amino-4'-methoxyacetanilide is diazotized in a conventional manner, and is coupled with 2,5-dimethoxyaniline. The product is further diazotized by sodium nitrite and coupled with 2R acid. Still further, the product is diazotized by sodium nitrite and is added to a solution of m-phenylenediamine-4-sulfonic acid to be coupled at a range of from 4 to 5. The resulting dye is salted out by addition of sodium chloride and is collected by filtration. Impurities are eliminated from the product by repetition of dissolution in water, salting-out by sodium chloride, and collection by filtration. Thereafter, the product is purified by means of ultrafiltration apparatus (made by Sartorius GmbH). Thus the exemplified Dye No. 2 is synthesized.
Suitable water-soluble organic solvents to be mixed with water include alcohols having 1 to 5 carbons such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, isobutyl alcohol, n-pentanol, etc.; amides such as dimethylformamide, dimethylacetamide, etc.; ketones and ketoalcohols such as acetone, diacetone alcohol, etc.; cyclic ethers such as dioxane, etc.; polyalkylene glycols such as polyethylene glycol, polypropylene glycol, etc.; alkylene glycols having an alkylene group of 2 to 6 carbons such as ethylene glycol, propylene glycol, butylene glycol, triethylene glycol, 1,2,6-hexane triol, thiodiglycol, hexylene glycol, diethylene glycol, etc.; glycerin; lower alkyl ethers of a polyhydric alcohol such as ethylene glycol monomethyl (or monoethyl) ether, diethylene glycol monomethyl (or monoethyl) ether, triethylene glycol monomethyl (or monoethyl) ether, etc.; lower alkyl diethers of a polyhydric alcohol such as triethylene glycol dimethyl (or diethyl) ether, tetraethylene glycol dimethyl (or diethyl) ether, etc.; sulfolane, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, and the like.
The amount of water to be used is generally in the range of from 10 to 97.5% by weight, preferably not less than 35% by weight, still more preferably not less than 45% by weight of the total weight of the ink. At a less amount of the water, a low-volatile organic solvent remains in a formed image, which undesirably causes problems of migration of the dye and running or feathering of the formed image.
On application of an electric signal to the electrodes 17-1 and 17-2, the region designated by a symbol "n" on the heat-generation head 15 generates heat abruptly to form a bubble in the ink 21 at the position adjacent thereto. The pressure generated by the bubble pushes out the meniscus 23 and ejects the ink 21, as recording droplets 24, and the ink droplets fly to a recording medium 25. FIG. 2 illustrates an appearance of a multi-head constructed by juxtaposing a multiplicity of heads shown in FIG. 1A. The multi-head is prepared by bonding a glass plate having multi-grooves with a heat-generation head 28 similar to the one described in FIG. 1A.
TABLE 1______________________________________                       QuantityNo.     Ink components      used______________________________________1       Exemplified dye No. 1                        3 parts   Diethylene glycol   25 parts   Pure water          72 parts2       Exemplified dye No. 2                        3 parts   Diethylene glycol   20 parts   N-methyl-2-pyrrolidone                       15 parts   Pure water          62 parts3       Exemplified dye No. 3                        3 parts   Polyethylene glycol 300                       20 parts   Pure water          77 parts4       Exemplified dye No. 4                        3 parts   Ethylene glycol     25 parts   Pure water          72 parts5       Exemplified dye No. 5                        3 parts   Glycerin            15 parts   Pure water          82 parts6       Exemplified dye No. 6                        3 parts   Diethylene glycol   15 parts   Ethylene glycol monoethyl ether                       10 parts   Pure water          72 parts7       Exemplified dye No. 7                        3 parts   Ethylene glycol     20 parts   Isopropyl alcohol    5 parts   Pure water          72 parts8       Exemplified dye No. 8                        3 parts   Glycerin            15 parts   N-methyl-2-pyrrolidone                       10 parts   Pure water          72 parts9       Exemplified dye No. 9                        3 parts   Ethylene glycol     20 parts   Ethanol              5 parts   Pure water          72 parts10      Exemplified dye No. 10                        3 parts   Diethylene glycol   25 parts   Pure water          72 parts11      Exemplified dye No. 11                        3 parts   Polyethylene glycol 300                       20 parts   Isopropyl alcohol   10 parts   Pure water          67 parts12      Exemplified dye No. 12                        3 parts   Diethylene glycol   20 parts   n-Propyl alcohol     5 parts   Pure water          72 parts______________________________________
The inks shown in Table 1 above were respectively mounted on an ink-jet printer BJ-80A (made by Canon K.K., nozzle size: 50�40 μm, 24 nozzles) employing a heat-generating element as an ink-ejecting energy source. Printing was conducted on the recording mediums shown below for evaluation regarding the items of (a) clogging on re-start of printing after a short intermission of printing, (b) recoverability from clogging on re-start of printing after a long term of intermission of printing, and (c) resistance of printed image to discoloration.
(a) Clogging on re-start of printing after a short intermission of printing
(b) Recoverability from clogging after a long term of intermission of printing
(c) Resistance to discoloration
Solid printing was conducted on the recording mediums A, B, C, and D in a size of 10 mm�30 mm. The printed recording mediums were left standing for 30 minutes in a dark chamber containing ozone at a concentration of 0.3�0.05% by volume for accelerating discoloration. The color difference (ΔE* ab) caused by the 30 minute standing was measured (according to JIS Z8730). The results are shown in Table 2.
TABLE 2______________________________________      &#916;E*ab      Recording mediumInk No.      A     B           C   D______________________________________1            4.2   3.6         5.1 2.72            5.5   4.8         5.2 3.03            4.9   4.2         4.5 2.94            4.8   5.0         4.1 3.15            5.1   4.9         4.2 3.36            6.0   5.9         4.6 4.07            5.2   5.0         4.7 4.18            5.4   4.0         3.9 3.79            6.1   5.5         5.6 4.210           5.6   5.6         4.8 3.011           5.1   4.5         4.2 3.412           6.1   5.9         5.2 3.9______________________________________
The inks shown in Table 3 below were prepared by mixing the components in Table 3 and treating them in the same manner as in the Examples. Each ink was employed for solid printing on the recording mediums A, B, and C by means of the same recording apparatus as in Examples. The test specimens of the printed matters were subjected to the test in the aforementioned ozone-containing test chamber in the same manner as above. As the results, all of the values ΔE* ab were not less than 20. The color differences after exposure to indoor light for three months were not less than 12 for all of the samples.
TABLE 3______________________________________                        QuantityNo.     Ink components       used______________________________________13      Undermentioned dye 13                         3 parts   Diethylene glycol    25 parts   Pure water           72 parts14      Undermentioned dye 14                         3 parts   Ethylene glycol      20 parts   Polyethylene glycol 300                        10 parts   Pure water           67 parts15      Undermentioned dye No. 15                         3 parts   Glycerin             15 parts   Diethylene glycol monoethyl ether                        10 parts   Pure water           72 parts16      Undermentioned dye No. 16                         3 parts   Diethylene glycol    20 parts   Isopropyl alcohol     5 parts   Pure water           72 parts17      Undermentioned dye No. 17                         3 parts   Ethylene glycol      20 parts   N-methyl-2-pyrrolidone                        10 parts   Pure water           67 parts______________________________________ ##STR5##
In the present invention, the use of the compound (or dye) represented by the general formula (A) as the dye in an ink gives a recording liquid which has the properties required for printed matters on ordinary paper and forms images of less discoloration on coated paper. Further the use thereof gives an image of high image quality, exhibiting high resolution and less discoloration, and having satisfactory fastness properties.
The ink of the present invention exhibits the aforementioned characteristics sufficiently at the neutral range of pH 4 to 10, which is satisfactory in view of safety because of no need of addition for strongly alkaline substances as described in Japanese Patent Application Laid-open No. 56-57862.
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS4255327 *Mar 27, 1979Mar 10, 1981Crompton & Knowles CorporationDirect black dyeUS4373954 *Apr 22, 1981Feb 15, 1983Canon Kabushiki KaishaRecording liquid and method for producing the sameUS4395288 *Apr 5, 1982Jul 26, 1983Canon Kabushiki KaishaLiquid recording mediumUS4426226 *Jun 22, 1982Jan 17, 1984Canon Kabushiki KaishaRecording liquidUS4435717 *Mar 22, 1982Mar 6, 1984Canon Kabushiki KaishaLiquid jet recording process and recording liquid thereforUS4557761 *Nov 17, 1983Dec 10, 1985Canon Kabushiki KaishaRecording liquidUS4620876 *Oct 24, 1985Nov 4, 1986Ricoh Company, Ltd.Aqueous ink for ink-jet printingUS4661158 *May 10, 1985Apr 28, 1987Canon Kabushiki KaishaRecording liquidUS4732613 *Nov 6, 1985Mar 22, 1988Canon Kabushiki KaishaRecording liquidUS4734489 *Mar 27, 1986Mar 29, 1988Taoka Chemical Company, LimitedTrisazo compounds useful in producing water-resistant ink compositionsUS4765838 *Aug 11, 1986Aug 23, 1988Mitsubishi Chemical Industries Ltd.Water-soluble dye composition and recording liquid containing the sameUS4778525 *Mar 23, 1987Oct 18, 1988Canon Kabushiki KaishaRecording liquidUS4804411 *Feb 13, 1987Feb 14, 1989Canon Kabushiki KaishaRecording liquidUS4841037 *Jun 10, 1986Jun 20, 1989Canon Kabushiki KaishaAmino sulfonaphtholtrisazo compounds and recording liquids containing the sameUS4864324 *Aug 11, 1987Sep 5, 1989Canon Kabushiki KaishaColor image forming method and ink used thereforUS5017227 *Jul 26, 1989May 21, 1991Canon Kabushiki KaishaRecording liquid and ink-jet recording process using sameDE3330379A1 *Aug 23, 1983Feb 23, 1984Ricoh KkWaessrige tinte fuer den tintenstrahldruckGB2108518A * Title not availableJPH01135880A * Title not availableJPH01193375A * Title not availableJPS5657862A * Title not availableJPS5993766A * Title not availableJPS5993768A * Title not availableJPS6210274A * Title not availableJPS6435880A * Title not availableJPS55151070A * Title not available* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS5258505 *Mar 27, 1992Nov 2, 1993Canon Kabushiki KaishaTrisazo compounds, and dye compositions containing sameUS5415686 *Apr 5, 1994May 16, 1995Canon Kabushiki KaishaInk, ink-jet recording method making use of the same and instrument provided with the inkUS5429671 *Mar 8, 1994Jul 4, 1995Canon Kabushiki KaishaInk, and ink-jet recording method and apparatus employing the inkUS5451251 *Feb 23, 1994Sep 19, 1995Canon Kabushiki KaishaInk, and ink-jet recording method and instrument using the sameUS5466282 *May 12, 1994Nov 14, 1995Canon Kabushiki KaishaAzo dye compound, ink containing the same, and recording method and instrument using the inkUS5482545 *Dec 23, 1994Jan 9, 1996Canon Kabushiki KaishaInk, and ink-jet recording method and instrument using the sameUS5482546 *Mar 28, 1995Jan 9, 1996Canon Kabushiki KaishaDye, ink containing the same, and ink-jet recording method and instrument using the inkUS5500023 *Apr 18, 1994Mar 19, 1996Canon Kabushiki KaishaInk-jet printing process, ink set for use in such process, and processed article obtained therebyUS5686951 *Oct 25, 1995Nov 11, 1997Canon Kabushiki KaishaInk jet printing method and printed articleUS5728201 *Sep 12, 1996Mar 17, 1998Canon Kabushiki KaishaInk, and ink-jet recording method and instruments using the sameUS6003987 *Dec 14, 1995Dec 21, 1999Canon Kabushiki KaishaInk set recording apparatus and method using ink set having a dye that becomes insoluble when mixed with another dyeUS6186615Jan 27, 1997Feb 13, 2001Canon Kabushiki KaishaApparatus and method for forming a black image in which black ink is overlaid on color inkUS7144452Dec 30, 2005Dec 5, 2006Canon Kabushiki KaishaInk jet black ink, ink set, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatusUS7198664Jan 26, 2006Apr 3, 2007Canon Kabushiki KaishaInk jet black ink, ink set, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatusUS7481525Feb 23, 2006Jan 27, 2009Canon Finetech Inc.Ink-jet water-based ink, ink-jet recording method, ink cartridge and ink-jet recording apparatusUS7771526Aug 10, 2010Canon Finetech Inc.Ink jet aqueous ink, ink jet recording method, ink cartridge and ink jet recording apparatusUS8043423Dec 16, 2008Oct 25, 2011Canon Finetech Inc.Pigment dispersion liquid, ink jet recording ink, ink jet recording method, ink cartridge and ink jet recording apparatusUS8876962Aug 13, 2012Nov 4, 2014Canon Kabushiki KaishaAqueous ink, ink cartridge, and ink jet recording methodUS9187662Feb 27, 2013Nov 17, 2015Canon Kabushiki KaishaInk, ink cartridge and ink jet recording methodUS20060156952 *Dec 30, 2005Jul 20, 2006Canon Kabushiki KaishaInk jet black ink, ink set, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatusUS20060192826 *Feb 23, 2006Aug 31, 2006Canon Finetech Inc.Ink-jet water-based ink, ink-jet recording method, ink cartridge and ink-jet recording apparatusUS20070032570 *Nov 10, 2004Feb 8, 2007Canon Kabushiki KaishaInk comprising a block copolymer dispersing agent having a hydrophilic and a hydrophobic segment and an ink-applying process and apparatus using the sameUS20070105980 *Nov 2, 2006May 10, 2007Canon Finetech Inc.Ink jet aqueous ink, ink jet recording method, ink cartridge and ink jet recording apparatusUS20090162552 *Dec 16, 2008Jun 25, 2009Canon Finetech Inc.Pigment dispersion liquid, ink jet recording ink, ink jet recording method, ink cartridge and ink jet recording apparatus* Cited by examinerClassifications U.S. Classification106/31.52, 534/809, 534/680, 347/100, 534/687, 534/810, 534/812, 534/811, 534/815, 534/685International ClassificationC09D11/00Cooperative ClassificationC09D11/328European ClassificationC09D11/328Legal EventsDateCodeEventDescriptionJan 23, 1991ASAssignmentOwner name: CANON KABUSHIKI KAISHA, 30-2, 3-CHOME, SHIMOMARUKOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:EIDA, TSUYOSHI;YAMAMOTO, TAKAO;YAMAMOTO, MAYUMI;REEL/FRAME:005586/0547Effective date: 19910117Oct 12, 1993CCCertificate of correctionNov 29, 1995FPAYFee paymentYear of fee payment: 4Dec 29, 1999FPAYFee paymentYear of fee payment: 8Dec 9, 2003FPAYFee paymentYear of fee payment: 12RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services