CN102757689B - 相变油墨及其制备方法 - Google Patents
相变油墨及其制备方法 Download PDFInfo
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- CN102757689B CN102757689B CN201210127685.7A CN201210127685A CN102757689B CN 102757689 B CN102757689 B CN 102757689B CN 201210127685 A CN201210127685 A CN 201210127685A CN 102757689 B CN102757689 B CN 102757689B
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- 238000007645 offset printing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012782 phase change material Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
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
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Ink Jet (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/095770 | 2011-04-27 | ||
| US13/095,770 | 2011-04-27 | ||
| US13/095,770 US8328924B2 (en) | 2011-04-27 | 2011-04-27 | Phase change inks and methods of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102757689A CN102757689A (zh) | 2012-10-31 |
| CN102757689B true CN102757689B (zh) | 2016-03-23 |
Family
ID=47007860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210127685.7A Expired - Fee Related CN102757689B (zh) | 2011-04-27 | 2012-04-26 | 相变油墨及其制备方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8328924B2 (enExample) |
| JP (1) | JP5865764B2 (enExample) |
| CN (1) | CN102757689B (enExample) |
| CA (1) | CA2774656C (enExample) |
| DE (1) | DE102012205871B4 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8833917B2 (en) * | 2011-04-27 | 2014-09-16 | Xerox Corporation | Solid ink compositions comprising crystalline-amorphous mixtures |
| US8308859B1 (en) | 2011-04-27 | 2012-11-13 | Xerox Corporation | Phase change ink components and methods of making the same |
| US8814999B2 (en) * | 2012-04-26 | 2014-08-26 | Xerox Corporation | Phase change ink compositions comprising crystalline sulfone compounds and derivatives thereof |
| US8741040B2 (en) * | 2012-04-26 | 2014-06-03 | Xerox Corporation | Phase change ink compositions comprising aromatic ethers |
| US8888905B2 (en) | 2012-04-26 | 2014-11-18 | Xerox Corporation | Fast crystallizing crystalline-amorphous ink compositions and methods for making the same |
| US8647424B2 (en) * | 2012-04-26 | 2014-02-11 | Xerox Corporation | Phase change inks comprising inorganic nucleating agents |
| US9528016B2 (en) | 2012-04-26 | 2016-12-27 | Xerox Corporation | Phase change inks comprising crystalline amides |
| US9228101B2 (en) * | 2012-04-26 | 2016-01-05 | Xerox Corporation | Rapidly crystallizing phase change inks and methods for forming the same |
| US8784547B2 (en) * | 2012-06-18 | 2014-07-22 | Xerox Corporation | Lightfast solid ink compositions |
| US8808438B2 (en) * | 2013-01-14 | 2014-08-19 | Xerox Corporation | Amorphous materials for use in phase change inks |
| US9109131B2 (en) * | 2013-01-16 | 2015-08-18 | Xerox Corporation | Photochromic phase change ink compositions |
| US9139743B2 (en) | 2013-01-31 | 2015-09-22 | Xerox Corporation | Malic acid derivatives as amorphous materials for phase change ink |
| US8747536B1 (en) | 2013-01-31 | 2014-06-10 | Xerox Corporation | Phase change ink formulation including malic acid derivatives as amorphous materials |
| US8778070B1 (en) * | 2013-02-13 | 2014-07-15 | Xerox Corporation | Ink composition and method of jetting ink |
| US9187663B2 (en) | 2013-03-21 | 2015-11-17 | Xerox Corporation | Ink composition and method of jetting ink |
| US9139746B2 (en) * | 2013-06-04 | 2015-09-22 | Xerox Corporation | Phase change ink compositions comprising mixtures of ester of tartaric acid and ester of citric acid as amorphous materials |
| US9074104B2 (en) * | 2013-09-04 | 2015-07-07 | Xerox Corporation | Inks comprising amorphous ureas |
| US9447297B2 (en) * | 2013-10-14 | 2016-09-20 | Xerox Corporation | Phase change ink containing amorphous amides |
| US9303172B2 (en) * | 2013-10-31 | 2016-04-05 | Xerox Corporation | Spreadable ink composition and method of predicting whether ink composition will have acceptable spreading performance |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1029903A1 (en) * | 1999-02-19 | 2000-08-23 | Hewlett-Packard Company | Bleed control solvents for pigmented and dye-based inks |
| EP1221467A1 (en) * | 2001-01-08 | 2002-07-10 | Océ-Technologies B.V. | Ink composition for a meltable ink |
| CN1637085A (zh) * | 2003-11-25 | 2005-07-13 | 施乐公司 | 制备相变型油墨的方法 |
| CN101684216A (zh) * | 2008-09-23 | 2010-03-31 | 施乐公司 | 含低粘度官能化蜡的油墨载体,含该载体的相变油墨,及制备方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490731A (en) | 1982-11-22 | 1984-12-25 | Hewlett-Packard Company | Ink dispenser with "frozen" solid ink |
| US5195430A (en) | 1989-05-24 | 1993-03-23 | Tektronix, Inc. | Dual roller apparatus for pressure fixing sheet material |
| US5231135A (en) | 1989-09-05 | 1993-07-27 | Milliken Research Corporation | Lightfast colored polymeric coatings and process for making same |
| JP3045819B2 (ja) * | 1991-07-17 | 2000-05-29 | 株式会社リコー | インクジェット記録用インク組成物 |
| US5621022A (en) | 1992-11-25 | 1997-04-15 | Tektronix, Inc. | Use of polymeric dyes in hot melt ink jet inks |
| US5389958A (en) | 1992-11-25 | 1995-02-14 | Tektronix, Inc. | Imaging process |
| NL1005174C2 (nl) | 1997-02-04 | 1998-08-06 | Oce Tech Bv | Inktsamenstelling voor een smeltbare inkt. |
| NL1009791C2 (nl) * | 1998-08-03 | 2000-02-04 | Oce Tech Bv | Inktsamenstelling voor een smeltbare inkt. |
| US6221137B1 (en) | 1999-06-18 | 2001-04-24 | Xerox Corporation | Metal phthalocyanine colorants for phase change inks |
| NL1012549C2 (nl) | 1999-07-09 | 2001-01-10 | Ocu Technologies B V | Inktsamenstelling voor een smeltbare inkt en een werkwijze voor het bedrukken van een substraat met een dergelijke inktsamenstelling. |
| US6423376B1 (en) * | 2000-04-06 | 2002-07-23 | Air Products And Chemicals, Inc. | Tartaric acid diesters as biodegradable surfactants |
| US6476219B1 (en) | 2002-02-08 | 2002-11-05 | Xerox Corporation | Methods for preparing phthalocyanine compositions |
| US6726755B2 (en) | 2002-02-08 | 2004-04-27 | Xerox Corporation | Ink compositions containing phthalocyanines |
| US6472523B1 (en) | 2002-02-08 | 2002-10-29 | Xerox Corporation | Phthalocyanine compositions |
| NL1020682C2 (nl) | 2002-05-27 | 2003-11-28 | Oce Tech Bv | Smeltbare inktsamenstelling. |
| US6590082B1 (en) | 2002-06-27 | 2003-07-08 | Xerox Corporation | Azo pyridone colorants |
| US6576747B1 (en) | 2002-06-27 | 2003-06-10 | Xerox Corporation | Processes for preparing dianthranilate compounds and diazopyridone colorants |
| US6646111B1 (en) | 2002-06-27 | 2003-11-11 | Xerox Corporation | Dimeric azo pyridone colorants |
| US6713614B2 (en) | 2002-06-27 | 2004-03-30 | Xerox Corporation | Dimeric azo pyridone colorants |
| US6696552B2 (en) | 2002-06-27 | 2004-02-24 | Xerox Corporation | Process for preparing substituted pyridone compounds |
| US6576748B1 (en) | 2002-06-27 | 2003-06-10 | Xerox Corporation | Method for making dimeric azo pyridone colorants |
| US6755902B2 (en) | 2002-06-27 | 2004-06-29 | Xerox Corporation | Phase change inks containing azo pyridone colorants |
| US6663703B1 (en) | 2002-06-27 | 2003-12-16 | Xerox Corporation | Phase change inks containing dimeric azo pyridone colorants |
| US6673139B1 (en) | 2002-06-27 | 2004-01-06 | Xerox Corporation | Phase change inks containing dimeric azo pyridone colorants |
| US6958406B2 (en) | 2002-09-27 | 2005-10-25 | Xerox Corporation | Colorant compounds |
| US7053227B2 (en) | 2002-09-27 | 2006-05-30 | Xerox Corporation | Methods for making colorant compounds |
| US6821327B2 (en) | 2002-09-27 | 2004-11-23 | Xerox Corporation | Phase change inks |
| US7381831B1 (en) | 2007-04-04 | 2008-06-03 | Xerox Corporation | Colorant compounds |
| US7677713B2 (en) * | 2007-05-30 | 2010-03-16 | Xerox Corporation | Solid ink set incorporating naturally derived materials and processes thereof |
| US7427323B1 (en) | 2007-06-07 | 2008-09-23 | Xerox Corporation | Quinacridone nanoscale pigment particles |
| US20090223409A1 (en) * | 2008-03-07 | 2009-09-10 | Xerox Corporation | Compounds suitable for use in inks and inks having such compounds |
-
2011
- 2011-04-27 US US13/095,770 patent/US8328924B2/en not_active Expired - Fee Related
-
2012
- 2012-04-03 JP JP2012084602A patent/JP5865764B2/ja not_active Expired - Fee Related
- 2012-04-11 DE DE102012205871.0A patent/DE102012205871B4/de not_active Expired - Fee Related
- 2012-04-20 CA CA2774656A patent/CA2774656C/en not_active Expired - Fee Related
- 2012-04-26 CN CN201210127685.7A patent/CN102757689B/zh not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1029903A1 (en) * | 1999-02-19 | 2000-08-23 | Hewlett-Packard Company | Bleed control solvents for pigmented and dye-based inks |
| EP1221467A1 (en) * | 2001-01-08 | 2002-07-10 | Océ-Technologies B.V. | Ink composition for a meltable ink |
| CN1637085A (zh) * | 2003-11-25 | 2005-07-13 | 施乐公司 | 制备相变型油墨的方法 |
| CN101684216A (zh) * | 2008-09-23 | 2010-03-31 | 施乐公司 | 含低粘度官能化蜡的油墨载体,含该载体的相变油墨,及制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2774656A1 (en) | 2012-10-27 |
| JP2012233167A (ja) | 2012-11-29 |
| CN102757689A (zh) | 2012-10-31 |
| US8328924B2 (en) | 2012-12-11 |
| CA2774656C (en) | 2016-06-07 |
| DE102012205871A1 (de) | 2012-10-31 |
| DE102012205871B4 (de) | 2018-05-03 |
| JP5865764B2 (ja) | 2016-02-17 |
| US20120272864A1 (en) | 2012-11-01 |
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