CA2411024A1 - Phase change inks containing borate esters - Google Patents
Phase change inks containing borate esters Download PDFInfo
- Publication number
- CA2411024A1 CA2411024A1 CA002411024A CA2411024A CA2411024A1 CA 2411024 A1 CA2411024 A1 CA 2411024A1 CA 002411024 A CA002411024 A CA 002411024A CA 2411024 A CA2411024 A CA 2411024A CA 2411024 A1 CA2411024 A1 CA 2411024A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- ink
- borate
- ester
- borate ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
Abstract
Disclosed is a phase change ink composition comprising a colorant and an ink vehicle, said ink being a solid at temperatures less than about 50°C, wherein the ink vehicle comprises a borate ester.
Claims (20)
1. A phase change ink composition comprising a colorant and an ink vehicle, said ink being a solid at temperatures less than about 50°C, wherein the ink vehicle comprises a borate ester.
2. An ink according to claim 1 wherein the borate ester is monomeric.
3. An ink according to claim 1 wherein the borate ester is a polymer having at least some repeat monomer units derived from one or more monomeric borate esters.
4. An ink according to claim 1 wherein the borate ester is of the general formula wherein R1, R2, and R3 each, independently of the others, is an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, or a polyalkyleneoxy group.
5. An ink according to claim 1 wherein the borate ester is of one of the general formulae wherein R4 and R5 each, independently of the other, is an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, a polyalkyleneoxy group, wherein R4 and R5 can be joined together to form a ring, R6, R7, R8, R9, R10, and R11 each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, a polyalkyleneoxy group, a hydroxy group, an amine group, an ammonium group, a cyano group, a pyridine group, a pyridinium group, an ether group, an aldehyde group, a ketone group, an ester group, an amide group, a carbonyl group, a sulfide group, a sulfoxide group, a phosphine group, a phosphonium group, a nitrite group, a mercapto group, a nitroso group, a halogen atom, a nitro group, a sulfone group, or an acyl group, wherein one or more of R6, R7, R8, R9, R10, and R11 can be absent if a ring carbon atom has a double bond or a triple bond to another R group or to another ring carbon atom, and R12 and R13 each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, or a polyalkyleneoxy group, wherein R6, R7, R8, R9, R10, R11, R12, and/or R13 can be joined together to form a ring.
6. An ink according to claim 1 wherein the borate ester is disorbitan borate, disorbitol borate, a borate ester of glycerin monoethoxylate, diglycerol borate, N,N-dibutylethanolamine glycerol borate, a glycerol borate monoester, sorbitol glycerol borate, bis-neopentylglycol borate, trimethylene borate, glycerol salicylamide borate, a borate ester of polyethylene glycol methyl ether, triethylene glycol monomethyl ether borate, salicylamide borate, N,N-dibutylethanolamine sorbitol borate, salicylamide sorbitol borate, N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate, N,N-dibutylethanolamine/poly(propylene glycol) monobutyl ether borate, glycerol borate laurate, sorbitan glycerol borate, or a mixture thereof.
7. An ink according to claim 1 wherein the borate ester is present in the ink in an amount of at least about 20 percent by weight of the ink.
8. An ink according to claim 1 wherein the borate ester is present in the ink in an amount of at least about 50 percent by weight of the ink.
9. An ink according to claim 1 wherein the borate ester is present in the ink in an amount of at least about 70 percent by weight of the ink.
10. An ink according to claim 1 wherein the colorant is present in the ink in an amount of at least about 0.5 percent by weight of the ink.
11. An ink according to claim 1 wherein the ink is solid at temperatures of about 70°C and lower.
12. An ink according to claim 1 wherein the ink is solid at temperatures of about 80°C and lower.
13. A process which comprises incorporating into an ink jet printing apparatus a phase change ink composition comprising a colorant and an ink vehicle, said ink being a solid at temperatures less than about 50°C, wherein the ink vehicle comprises a borate ester, melting the ink, and causing droplets of the melted ink to be ejected in an imagewise pattern onto a substrate.
14. A process according to claim 13 wherein the printing apparatus employs a piezoelectric printing process wherein droplets of the ink are caused to be ejected in imagewise pattern by oscillations of piezoelectric vibrating elements.
15. A process according to claim 13 wherein the ink has a viscosity of no more than about 30 centipoise at jetting temperatures.
16. A process according to claim 13 wherein the ink has a viscosity of no more than about 20 centipoise at jetting temperatures.
17. A process according to claim 13 wherein the ink has a viscosity of no more than about 15 centipoise at jetting temperatures.
18. A process according to claim 13 wherein the substrate is a final recording sheet and droplets of the melted ink are ejected in an imagewise pattern directly onto the final recording sheet.
19. A process according to claim 13 wherein the substrate is an intermediate transfer member and droplets of the melted ink are ejected in an imagewise pattern onto the intermediate transfer member followed by transfer of the imagewise pattern from the intermediate transfer member to a final recording sheet.
20. A process according to claim 19 wherein the intermediate transfer member is heated to a temperature above that of the final recording sheet and below that of the melted ink in the printing apparatus.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/040,464 US6585816B1 (en) | 2001-11-09 | 2001-11-09 | Phase change inks containing borate esters |
US10/040,464 | 2001-11-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2411024A1 true CA2411024A1 (en) | 2003-05-09 |
CA2411024C CA2411024C (en) | 2010-01-12 |
Family
ID=21911113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002411024A Expired - Fee Related CA2411024C (en) | 2001-11-09 | 2002-11-01 | Phase change inks containing borate esters |
Country Status (5)
Country | Link |
---|---|
US (1) | US6585816B1 (en) |
EP (1) | EP1310532B1 (en) |
JP (1) | JP2003206427A (en) |
CA (1) | CA2411024C (en) |
DE (1) | DE60211451T2 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7578875B2 (en) * | 2005-11-30 | 2009-08-25 | Xerox Corporation | Black inks and method for making same |
US20090119914A1 (en) * | 2005-12-27 | 2009-05-14 | Clark Roger F | Process for Forming Electrical Contacts on a Semiconductor Wafer Using a Phase Changing Ink |
US20090134369A1 (en) * | 2007-11-26 | 2009-05-28 | Applied Nanoworks, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
JP4816979B2 (en) * | 2008-10-29 | 2011-11-16 | ブラザー工業株式会社 | Water-based ink for ink jet recording, ink jet recording method and color change inhibitor |
JP5778438B2 (en) * | 2011-02-14 | 2015-09-16 | 理想科学工業株式会社 | Non-aqueous ink |
US8961673B2 (en) * | 2012-04-26 | 2015-02-24 | Xerox Corporation | Phase change ink compositions comprising diurethanes as amorphous materials |
US8784547B2 (en) * | 2012-06-18 | 2014-07-22 | Xerox Corporation | Lightfast solid ink compositions |
CN113755228A (en) * | 2021-09-27 | 2021-12-07 | 浙江嘉富力环保科技有限公司 | Class7 boric acid ester type brake fluid and preparation method thereof |
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US3637794A (en) | 1967-04-13 | 1972-01-25 | Olin Mathieson | Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols |
BE755392A (en) | 1969-08-28 | 1971-02-01 | Teletype Corp | INK AND ELECTROSTATIC PRINTING APPARATUS |
US4192759A (en) | 1978-07-17 | 1980-03-11 | Toho Chemical Industry Co., Ltd. | Automotive brake fluid compositions including semipolar borates and heteroborates |
US4303445A (en) | 1980-07-18 | 1981-12-01 | Exxon Research & Engineering Co. | Ink jet printing formulations |
JPS5787480A (en) | 1980-11-21 | 1982-05-31 | Mitsubishi Pencil Co Ltd | Aqueous ink composition for ball-point pen |
US4390369A (en) | 1981-12-17 | 1983-06-28 | Exxon Research And Engineering Co. | Natural wax-containing ink jet inks |
JPS5823867A (en) * | 1981-08-04 | 1983-02-12 | Unitika Chem Kk | Remoistening hot-melt adhesive composition |
US4659383A (en) | 1981-12-17 | 1987-04-21 | Exxon Printing Systems, Inc. | High molecular weight, hot melt impulse ink jet ink |
US4820346A (en) | 1985-06-25 | 1989-04-11 | Howtek, Inc. | Ink jet printer ink |
US4745419A (en) | 1987-06-02 | 1988-05-17 | Xerox Corporation | Hot melt ink acoustic printing |
US4830671A (en) | 1987-09-18 | 1989-05-16 | Union Camp Corporation | Ink compositions for ink jet printing |
US5151120A (en) | 1989-03-31 | 1992-09-29 | Hewlett-Packard Company | Solid ink compositions for thermal ink-jet printing having improved printing characteristics |
US5122187A (en) | 1989-06-22 | 1992-06-16 | Xerox Corporation | Hot melt ink compositions |
US5006170A (en) | 1989-06-22 | 1991-04-09 | Xerox Corporation | Hot melt ink compositions |
US4975211A (en) | 1989-07-05 | 1990-12-04 | Chevron Research Company | Diethylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same |
US5171875A (en) | 1991-01-11 | 1992-12-15 | Lce Partnership | Beta branched borate esters |
US5541627A (en) | 1991-12-17 | 1996-07-30 | Xerox Corporation | Method and apparatus for ejecting a droplet using an electric field |
US5354368A (en) | 1993-05-04 | 1994-10-11 | Markem Corporation | Hot melt jet ink composition |
US5747554A (en) | 1996-03-29 | 1998-05-05 | Xerox Corporation | Ink compositions |
US5667568A (en) | 1996-03-29 | 1997-09-16 | Xerox Corporation | Hot melt ink compositions |
US5700316A (en) | 1996-03-29 | 1997-12-23 | Xerox Corporation | Acoustic ink compositions |
US5688312A (en) | 1996-03-29 | 1997-11-18 | Xerox Corporation | Ink compositions |
US5932630A (en) | 1996-05-02 | 1999-08-03 | Xerox Corporation | Ink compositions |
US5948149A (en) | 1996-06-11 | 1999-09-07 | Sony Corporation | Water-based ink composition |
US5698017A (en) | 1996-09-27 | 1997-12-16 | Xerox Corporation | Oxazoline hot melt ink compositions |
US5777023A (en) | 1996-10-01 | 1998-07-07 | Union Camp Corporation | Diamidediurethanes and hot-melt printing therewith |
US5693128A (en) | 1997-01-21 | 1997-12-02 | Xerox Corporation | Phase change hot melt ink compositions |
US5844020A (en) | 1997-03-31 | 1998-12-01 | Xerox Corporation | Phase change ink compositions |
JPH1112524A (en) | 1997-06-27 | 1999-01-19 | Pentel Kk | Aqueous gloss ink composition |
US5902390A (en) | 1997-09-23 | 1999-05-11 | Xerox Corporation | Ink compositions containing ketones |
US5876492A (en) | 1997-09-23 | 1999-03-02 | Xerox Corporation | Ink compositions containing esters |
US5958119A (en) | 1997-09-23 | 1999-09-28 | Xerox Corporation | Hot melt ink compositions |
US5931995A (en) | 1997-09-23 | 1999-08-03 | Xerox Corporation | Ink compositions |
US5922117A (en) | 1997-09-23 | 1999-07-13 | Xerox Corporation | Ink compositions containing alcohols |
US5989325A (en) | 1998-03-05 | 1999-11-23 | Xerox Corporation | Ink compositions |
JP2000104000A (en) | 1998-09-29 | 2000-04-11 | Pentel Corp | Water-based gloss ink composition |
US6059871A (en) | 1998-11-30 | 2000-05-09 | Xerox Corporation | Ink compositions |
US6071333A (en) | 1999-04-27 | 2000-06-06 | Xerox Corporation | Ink compositions |
US6045607A (en) | 1999-03-30 | 2000-04-04 | Xerox Corporation | Ink compositions |
US6066200A (en) | 1999-04-27 | 2000-05-23 | Xerox Corporation | Ink compositions |
-
2001
- 2001-11-09 US US10/040,464 patent/US6585816B1/en not_active Expired - Lifetime
-
2002
- 2002-11-01 CA CA002411024A patent/CA2411024C/en not_active Expired - Fee Related
- 2002-11-01 JP JP2002319300A patent/JP2003206427A/en active Pending
- 2002-11-11 EP EP02025050A patent/EP1310532B1/en not_active Expired - Fee Related
- 2002-11-11 DE DE60211451T patent/DE60211451T2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JP2003206427A (en) | 2003-07-22 |
US6585816B1 (en) | 2003-07-01 |
DE60211451T2 (en) | 2006-09-21 |
EP1310532B1 (en) | 2006-05-17 |
EP1310532A1 (en) | 2003-05-14 |
CA2411024C (en) | 2010-01-12 |
DE60211451D1 (en) | 2006-06-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20181101 |