CN102675915A - Water-soluble dye composition containing benzoyl H acid and preparation method thereof - Google Patents
Water-soluble dye composition containing benzoyl H acid and preparation method thereof Download PDFInfo
- Publication number
- CN102675915A CN102675915A CN2012100975854A CN201210097585A CN102675915A CN 102675915 A CN102675915 A CN 102675915A CN 2012100975854 A CN2012100975854 A CN 2012100975854A CN 201210097585 A CN201210097585 A CN 201210097585A CN 102675915 A CN102675915 A CN 102675915A
- Authority
- CN
- China
- Prior art keywords
- component
- acid
- water
- benzoyl
- soluble dye
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- -1 benzoyl H acid Chemical compound 0.000 title abstract description 7
- 150000003839 salts Chemical group 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000243 solution Substances 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 21
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 20
- 239000012954 diazonium Substances 0.000 claims description 14
- 150000001989 diazonium salts Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 235000010288 sodium nitrite Nutrition 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 238000010612 desalination reaction Methods 0.000 claims description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000009413 insulation Methods 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 6
- 238000007641 inkjet printing Methods 0.000 abstract description 4
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 230000007774 longterm Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 38
- 238000007639 printing Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000007921 spray Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- GCFAQSYBSUQUPL-UHFFFAOYSA-I pentasodium 5-[[4-chloro-6-[3-(2-sulfonatooxyethylsulfonyl)anilino]-1,3,5-triazin-2-yl]amino]-3-[(1,5-disulfonatonaphthalen-2-yl)diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].Oc1c(N=Nc2ccc3c(cccc3c2S([O-])(=O)=O)S([O-])(=O)=O)c(cc2cc(cc(Nc3nc(Cl)nc(Nc4cccc(c4)S(=O)(=O)CCOS([O-])(=O)=O)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O GCFAQSYBSUQUPL-UHFFFAOYSA-I 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 238000001223 reverse osmosis Methods 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000003245 working effect Effects 0.000 description 3
- 0 *c1cc(NC(c2ccccc2)=O)c(C([C@@](C(S(O)(=O)=O)=C2)N=Nc3c(*)c(cccc4)c4cc3)O)c2c1 Chemical compound *c1cc(NC(c2ccccc2)=O)c(C([C@@](C(S(O)(=O)=O)=C2)N=Nc3c(*)c(cccc4)c4cc3)O)c2c1 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- CFQPVBJOKYSPKG-UHFFFAOYSA-N 1,3-dimethylimidazol-2-one Chemical compound CN1C=CN(C)C1=O CFQPVBJOKYSPKG-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Images
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210097585.4A CN102675915B (en) | 2012-04-05 | 2012-04-05 | Water-soluble dye composition containing benzoyl H acid and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210097585.4A CN102675915B (en) | 2012-04-05 | 2012-04-05 | Water-soluble dye composition containing benzoyl H acid and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102675915A true CN102675915A (en) | 2012-09-19 |
CN102675915B CN102675915B (en) | 2014-03-26 |
Family
ID=46808495
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201210097585.4A Expired - Fee Related CN102675915B (en) | 2012-04-05 | 2012-04-05 | Water-soluble dye composition containing benzoyl H acid and preparation method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102675915B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111936586A (en) * | 2018-03-28 | 2020-11-13 | 精工爱普生株式会社 | Aqueous inkjet composition |
CN115449233A (en) * | 2022-10-12 | 2022-12-09 | 浙江亿得新材料股份有限公司 | Red dye for ink-jet printing, composition and preparation method thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6231653B1 (en) * | 1997-12-19 | 2001-05-15 | Zeneca Limited | Dye compositions |
US6395885B1 (en) * | 1998-06-05 | 2002-05-28 | Avecia Limited | Use of lithium salts of anionic dyes to enhance their light-fastness |
JP2004051750A (en) * | 2002-07-18 | 2004-02-19 | Mitsubishi Chemicals Corp | Inkjet recording method |
CN101704770A (en) * | 2009-11-16 | 2010-05-12 | 天津德凯化工股份有限公司 | Method for preparing purple reactive dye |
US20110014375A1 (en) * | 2009-07-15 | 2011-01-20 | Holloway Ann P | Magenta inkjet ink having improved print quality with porous photo media |
-
2012
- 2012-04-05 CN CN201210097585.4A patent/CN102675915B/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6231653B1 (en) * | 1997-12-19 | 2001-05-15 | Zeneca Limited | Dye compositions |
US6395885B1 (en) * | 1998-06-05 | 2002-05-28 | Avecia Limited | Use of lithium salts of anionic dyes to enhance their light-fastness |
JP2004051750A (en) * | 2002-07-18 | 2004-02-19 | Mitsubishi Chemicals Corp | Inkjet recording method |
US20110014375A1 (en) * | 2009-07-15 | 2011-01-20 | Holloway Ann P | Magenta inkjet ink having improved print quality with porous photo media |
CN101704770A (en) * | 2009-11-16 | 2010-05-12 | 天津德凯化工股份有限公司 | Method for preparing purple reactive dye |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111936586A (en) * | 2018-03-28 | 2020-11-13 | 精工爱普生株式会社 | Aqueous inkjet composition |
CN111936586B (en) * | 2018-03-28 | 2022-04-15 | 精工爱普生株式会社 | Aqueous inkjet composition |
CN115449233A (en) * | 2022-10-12 | 2022-12-09 | 浙江亿得新材料股份有限公司 | Red dye for ink-jet printing, composition and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CN102675915B (en) | 2014-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101448905B (en) | Black ink composition, ink set, ink cartridge, ink jet recording method and recorded matter | |
CN100334159C (en) | Coloring agent mixture | |
CN102079897B (en) | Water-based ink for ink-jet recording, ink cartridge, and ink-jet recording apparatus | |
CN101978000A (en) | Method of preparing modified colored pigments | |
CA2523256A1 (en) | Water-based coloring agent preparations for inkjet printing | |
CN102471622A (en) | Inkjet recording ink, ink cartridge and inkjet recording apparatus | |
US7097702B2 (en) | Acidic mono azo dyestuffs | |
CN100413927C (en) | Disazo dyes compounds and application thereof | |
TW201026785A (en) | Disazo compounds and their use in ink-jet printing | |
EP0602816A1 (en) | Magenta dye, jet ink, and color set | |
CN102675915B (en) | Water-soluble dye composition containing benzoyl H acid and preparation method thereof | |
JPH0254865B2 (en) | ||
MXPA05004562A (en) | Mono azo dyes. | |
CN1957043B (en) | Method for producing a liquid formulation of salts of sulphonic-acid azo dyes | |
CN102766348B (en) | Monoazo orange dye compound, preparation method thereof and ink-jet ink | |
CN1643076A (en) | Water-soluble yellow azo dyes | |
CN101248141A (en) | Azo compound, ink composition, recording method, and colored object | |
EP1694785A1 (en) | Inkjet inks and methods of preparing the same | |
CN102153884B (en) | Ink-type dye, and preparation method and application thereof | |
CN102504588A (en) | Turquoise blue active dye, as well as preparation method and application thereof | |
CN102558897B (en) | Flexible-chain-contained dikaryotic anthracene pyridine sulfoacid compound or salt thereof, and preparation method and application thereof | |
JP2005255952A (en) | Water-based ink composition | |
CN102719113B (en) | Ink-jet ink with light resistance and preparation method thereof | |
CN102924974B (en) | Ink jet dye composition, and preparation method and application thereof | |
CN102766347B (en) | Diazo dye and its black ink composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
C53 | Correction of patent of invention or patent application | ||
C56 | Change in the name or address of the patentee |
Owner name: SHANGHAI BESTON COLOR TECHNOLOGY CO., LTD. Free format text: FORMER NAME: SHANGHAI BESTON CHEMICAL TECHNOLOGY CO., LTD. |
|
CB03 | Change of inventor or designer information |
Inventor after: Li Jianfeng Inventor after: Li Chao Inventor after: XianYu Gongxuan Inventor before: Xianyu Gongxuan Inventor before: Li Jianfeng Inventor before: Li Chao |
|
COR | Change of bibliographic data |
Free format text: CORRECT: INVENTOR; FROM: GONGXUAN XIANYU LI JIANFENG LI CHAO TO: LI JIANFENG LI CHAO GONGXUAN XIANYU |
|
CP03 | Change of name, title or address |
Address after: Jiading District Waigang town 201806 Department of Shanghai City, No. 655 Po Patentee after: SHANGHAI BESTON CHEMICAL CO.,LTD. Address before: Jiading District Waigang town 200000 Department of Shanghai City, No. 655 Po Patentee before: SHANGHAI BESTON CHEMICAL Co.,Ltd. |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140326 |
|
CF01 | Termination of patent right due to non-payment of annual fee |