JP4593058B2 - 強塩基での処理及び置換による顔料の可溶化 - Google Patents
強塩基での処理及び置換による顔料の可溶化 Download PDFInfo
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- JP4593058B2 JP4593058B2 JP2002133054A JP2002133054A JP4593058B2 JP 4593058 B2 JP4593058 B2 JP 4593058B2 JP 2002133054 A JP2002133054 A JP 2002133054A JP 2002133054 A JP2002133054 A JP 2002133054A JP 4593058 B2 JP4593058 B2 JP 4593058B2
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- Prior art keywords
- pigment
- phenyl
- group
- salt
- carbon atoms
- Prior art date
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- 238000006467 substitution reaction Methods 0.000 title description 9
- 230000007928 solubilization Effects 0.000 title description 3
- 238000005063 solubilization Methods 0.000 title description 3
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- 239000000976 ink Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
- 150000005215 alkyl ethers Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000006184 cosolvent Substances 0.000 claims description 11
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 10
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 150000003869 acetamides Chemical class 0.000 claims description 8
- 239000003086 colorant Substances 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 5
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 4
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- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 3
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- SOFRHZUTPGJWAM-UHFFFAOYSA-N 3-hydroxy-4-[(2-methoxy-5-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound COc1ccc(cc1N=Nc1c(O)c(cc2ccccc12)C(=O)Nc1cccc(c1)[N+]([O-])=O)[N+]([O-])=O SOFRHZUTPGJWAM-UHFFFAOYSA-N 0.000 claims description 3
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- 150000004820 halides Chemical class 0.000 claims description 3
- KTDILAZSFSAPMD-UHFFFAOYSA-N n-(2-chloroethyl)aniline Chemical compound ClCCNC1=CC=CC=C1 KTDILAZSFSAPMD-UHFFFAOYSA-N 0.000 claims description 3
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003352 sequestering agent Substances 0.000 claims description 3
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 3
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical class C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 claims description 2
- NUJGORANFDSMOL-UHFFFAOYSA-N 2-chloroethylsulfonylbenzene Chemical compound ClCCS(=O)(=O)C1=CC=CC=C1 NUJGORANFDSMOL-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
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- 230000000996 additive effect Effects 0.000 claims description 2
- NXAIQSVCXQZNRY-UHFFFAOYSA-N chloromethylsulfonylbenzene Chemical compound ClCS(=O)(=O)C1=CC=CC=C1 NXAIQSVCXQZNRY-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000002424 x-ray crystallography Methods 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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
-
- 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
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/851,659 US6602335B2 (en) | 2001-05-08 | 2001-05-08 | Pigment solubilization via treatment with strong base and substitution |
| US09/851659 | 2001-05-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002338843A JP2002338843A (ja) | 2002-11-27 |
| JP2002338843A5 JP2002338843A5 (US06602335-20030805-C00020.png) | 2005-04-07 |
| JP4593058B2 true JP4593058B2 (ja) | 2010-12-08 |
Family
ID=25311326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002133054A Expired - Fee Related JP4593058B2 (ja) | 2001-05-08 | 2002-05-08 | 強塩基での処理及び置換による顔料の可溶化 |
Country Status (6)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE440124T1 (de) * | 2002-01-07 | 2009-09-15 | Cabot Corp | Modifizierte pigmentprodukte und solche enthaltende schwarzmatrizen |
| US6786957B2 (en) * | 2002-01-22 | 2004-09-07 | Hewlett-Packard Development Company, L.P. | Aqueous ink-jet inks for printing on commercial offset coated media |
| US7173078B2 (en) | 2002-04-12 | 2007-02-06 | Cabot Corporation | Process for preparing modified pigments |
| EP1594923B1 (en) * | 2003-01-17 | 2011-06-15 | Cabot Corporation | Methods for preparing aqueous colored pigment dispersions, and inkjet ink compositions |
| US6936097B2 (en) * | 2003-04-16 | 2005-08-30 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| US6942724B2 (en) * | 2003-04-16 | 2005-09-13 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| KR100540660B1 (ko) * | 2003-09-26 | 2006-01-10 | 삼성전자주식회사 | 루이스 산을 이용한 자가분산형 착색제의 제조 방법 및상기 착색제를 포함하는 잉크 조성물 |
| US7163577B2 (en) * | 2004-03-01 | 2007-01-16 | Hewlett-Packard Development Company, L.P. | Black pigmented ink-jet inks with improved frequency response |
| US20050256225A1 (en) * | 2004-05-11 | 2005-11-17 | Viola Michael S | Aqueous inkjet ink compositions comprising comb-branched copolymers |
| US7927416B2 (en) | 2006-10-31 | 2011-04-19 | Sensient Colors Inc. | Modified pigments and methods for making and using the same |
| EP2111430A2 (en) * | 2007-01-24 | 2009-10-28 | Cabot Corporation | Process to form modified pigments |
| JP2010519366A (ja) * | 2007-02-27 | 2010-06-03 | キャボット コーポレイション | 複数の改質された顔料を含むインクジェットインク組成物 |
| US7553358B2 (en) | 2007-05-01 | 2009-06-30 | Canon Kabushiki Kaisha | Ink jet ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus |
| CN101855302B (zh) | 2007-08-23 | 2014-10-01 | 森馨颜色公司 | 自分散颜料及制造和使用该自分散颜料的方法 |
| AU2010234392A1 (en) | 2009-04-07 | 2011-10-27 | Sensient Colors Inc. | Self-dispersing particles and methods for making and using the same |
| JP2015067741A (ja) * | 2013-09-30 | 2015-04-13 | Dic株式会社 | 着色剤及びその製造方法 |
| JP2015113435A (ja) * | 2013-12-13 | 2015-06-22 | Dic株式会社 | 活性エネルギー線硬化型組成物及び活性エネルギー線硬化型インクジェットインク |
| JP2016079241A (ja) * | 2014-10-14 | 2016-05-16 | Dic株式会社 | インクジェットプリンタ用インク |
| KR102484706B1 (ko) * | 2016-05-30 | 2023-01-03 | 경희대학교 산학협력단 | 안료변형 시너지스트, 이를 포함하는 안료 분산액 및 잉크 조성물 |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04224870A (ja) * | 1990-03-31 | 1992-08-14 | Ciba Geigy Ag | 顔料の製造方法 |
| JPH10110111A (ja) * | 1996-10-07 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JPH10110129A (ja) * | 1996-10-07 | 1998-04-28 | Toyo Ink Mfg Co Ltd | インクジェット用記録液 |
| JPH10110114A (ja) * | 1996-10-09 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JPH10110110A (ja) * | 1996-10-07 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JP2000053902A (ja) * | 1998-07-31 | 2000-02-22 | Hewlett Packard Co <Hp> | インクジェット印刷のための求核置換反応による巨大分子発色団へのポリマ―類の共有結合形付着 |
| JP2000095987A (ja) * | 1998-07-31 | 2000-04-04 | Hewlett Packard Co <Hp> | 共有結合で付着されたポリマ―をもつ変性巨大分子発色団を含むインクジェット用インク組成物 |
| JP2000513396A (ja) * | 1996-06-17 | 2000-10-10 | キャボット コーポレイション | 着色顔料およびそれを含む水性組成物 |
| WO2001062862A1 (fr) * | 2000-02-23 | 2001-08-30 | Seiko Epson Corporation | Procede servant a preparer une dispersion de pigment, dispersion de pigments obtenue au moyen de ce procede et encre d'imprimante a jet d'encre contenant cette dispersion |
| JP2002020673A (ja) * | 2000-04-10 | 2002-01-23 | Seiko Epson Corp | 顔料分散液の製造方法、その方法により得られた顔料分散液、その顔料分散液を用いたインクジェット記録用インク、並びに、そのインクを用いた記録方法および記録物 |
| JP2002275387A (ja) * | 2001-03-21 | 2002-09-25 | Ricoh Co Ltd | 有機顔料及びその製造方法、記録液、記録液カートリッジ、記録装置ならびに記録方法 |
| JP2002327144A (ja) * | 2000-06-28 | 2002-11-15 | Seiko Epson Corp | 顔料分散液の製造方法と顔料分散液、及びこれを用いたインクジェット記録用インク |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1356254A (en) * | 1970-07-16 | 1974-06-12 | Ciba Geigy Uk Ltd | Pigment compositions |
| US4468255A (en) * | 1983-08-10 | 1984-08-28 | Sun Chemical Corporation | Rheology modifiers for arylide yellow pigment dispersions and pigment dispersions containing same |
| JPS61255964A (ja) * | 1985-05-10 | 1986-11-13 | Toyo Soda Mfg Co Ltd | 有機顔料の製造法 |
| US5062894A (en) * | 1991-02-12 | 1991-11-05 | Sun Chemical Corporation | Poly (alkylene oxide)-modified diarylide pigment composition |
| GB9112155D0 (en) * | 1991-06-06 | 1991-07-24 | Ciba Geigy Ag | Production of pigments |
| US5246494A (en) * | 1991-07-23 | 1993-09-21 | Engelhard Corporation | Mixed coupled azo pigments |
| NL9101286A (nl) * | 1991-07-23 | 1993-02-16 | Oce Nederland Bv | Werkwijze voor het verbuigen van woorden, alsmede een data-verwerkings-eenheid voor het uitvoeren van een dergelijke werkwijze. |
| JP2879623B2 (ja) * | 1991-07-26 | 1999-04-05 | 富士写真フイルム株式会社 | カラー感光材料 |
| IL116379A (en) | 1994-12-15 | 2003-12-10 | Cabot Corp | Aqueous inks and coatings containing modified carbon products |
| US5571311A (en) | 1994-12-15 | 1996-11-05 | Cabot Corporation | Ink jet ink formulations containing carbon black products |
| IL116376A (en) | 1994-12-15 | 2001-03-19 | Cabot Corp | Aqueous ink jet ink compositions containing modified carbon products |
| US5554739A (en) | 1994-12-15 | 1996-09-10 | Cabot Corporation | Process for preparing carbon materials with diazonium salts and resultant carbon products |
| JP4697757B2 (ja) | 1996-06-14 | 2011-06-08 | キャボット コーポレイション | 変性された有色顔料類及びそれらを含むインキジェットインキ類 |
| US5928419A (en) * | 1996-10-07 | 1999-07-27 | Toyo Ink Manufacturing Co., Ltd. | Surface-treated organic pigment and process for the production thereof |
| EP1066352B2 (en) * | 1998-04-03 | 2008-10-01 | Cabot Corporation | Modified pigments having improved dispersing properties |
| CA2246156C (en) * | 1998-08-31 | 2008-07-08 | Sun Chemical Corporation | Energy curable inks incorporating grafted pigments |
| US6599356B2 (en) * | 2000-06-28 | 2003-07-29 | Seiko Epson Corporation | Method for manufacturing pigment dispersed liquid, and pigment dispersed liquid, and ink for ink-jet printer recording using said pigment dispersed liquid |
-
2001
- 2001-05-08 US US09/851,659 patent/US6602335B2/en not_active Expired - Fee Related
- 2001-10-31 TW TW090127044A patent/TWI230184B/zh not_active IP Right Cessation
-
2002
- 2002-02-05 KR KR1020020006388A patent/KR100812904B1/ko not_active IP Right Cessation
- 2002-05-07 DE DE60207631T patent/DE60207631T2/de not_active Expired - Lifetime
- 2002-05-07 EP EP02253169A patent/EP1256608B1/en not_active Expired - Fee Related
- 2002-05-08 JP JP2002133054A patent/JP4593058B2/ja not_active Expired - Fee Related
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04224870A (ja) * | 1990-03-31 | 1992-08-14 | Ciba Geigy Ag | 顔料の製造方法 |
| JP2000513396A (ja) * | 1996-06-17 | 2000-10-10 | キャボット コーポレイション | 着色顔料およびそれを含む水性組成物 |
| JPH10110111A (ja) * | 1996-10-07 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JPH10110129A (ja) * | 1996-10-07 | 1998-04-28 | Toyo Ink Mfg Co Ltd | インクジェット用記録液 |
| JPH10110110A (ja) * | 1996-10-07 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JPH10110114A (ja) * | 1996-10-09 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JP2000053902A (ja) * | 1998-07-31 | 2000-02-22 | Hewlett Packard Co <Hp> | インクジェット印刷のための求核置換反応による巨大分子発色団へのポリマ―類の共有結合形付着 |
| JP2000095987A (ja) * | 1998-07-31 | 2000-04-04 | Hewlett Packard Co <Hp> | 共有結合で付着されたポリマ―をもつ変性巨大分子発色団を含むインクジェット用インク組成物 |
| WO2001062862A1 (fr) * | 2000-02-23 | 2001-08-30 | Seiko Epson Corporation | Procede servant a preparer une dispersion de pigment, dispersion de pigments obtenue au moyen de ce procede et encre d'imprimante a jet d'encre contenant cette dispersion |
| JP2002020673A (ja) * | 2000-04-10 | 2002-01-23 | Seiko Epson Corp | 顔料分散液の製造方法、その方法により得られた顔料分散液、その顔料分散液を用いたインクジェット記録用インク、並びに、そのインクを用いた記録方法および記録物 |
| JP2002327144A (ja) * | 2000-06-28 | 2002-11-15 | Seiko Epson Corp | 顔料分散液の製造方法と顔料分散液、及びこれを用いたインクジェット記録用インク |
| JP2002275387A (ja) * | 2001-03-21 | 2002-09-25 | Ricoh Co Ltd | 有機顔料及びその製造方法、記録液、記録液カートリッジ、記録装置ならびに記録方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60207631T2 (de) | 2006-07-20 |
| TWI230184B (en) | 2005-04-01 |
| KR100812904B1 (ko) | 2008-03-11 |
| EP1256608A2 (en) | 2002-11-13 |
| EP1256608B1 (en) | 2005-11-30 |
| DE60207631D1 (de) | 2006-01-05 |
| US20020195022A1 (en) | 2002-12-26 |
| KR20020085783A (ko) | 2002-11-16 |
| US6602335B2 (en) | 2003-08-05 |
| JP2002338843A (ja) | 2002-11-27 |
| EP1256608A3 (en) | 2003-08-27 |
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