JP5175038B2 - ジスアゾ顔料組成物 - Google Patents
ジスアゾ顔料組成物 Download PDFInfo
- Publication number
- JP5175038B2 JP5175038B2 JP2006199730A JP2006199730A JP5175038B2 JP 5175038 B2 JP5175038 B2 JP 5175038B2 JP 2006199730 A JP2006199730 A JP 2006199730A JP 2006199730 A JP2006199730 A JP 2006199730A JP 5175038 B2 JP5175038 B2 JP 5175038B2
- Authority
- JP
- Japan
- Prior art keywords
- coupling component
- group
- mol
- coupling
- component
- 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.)
- Expired - Fee Related
Links
- 239000000049 pigment Substances 0.000 title claims description 99
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 86
- 239000000203 mixture Substances 0.000 title claims description 45
- 238000005859 coupling reaction Methods 0.000 claims description 254
- 238000010168 coupling process Methods 0.000 claims description 228
- 230000008878 coupling Effects 0.000 claims description 222
- 239000007795 chemical reaction product Substances 0.000 claims description 34
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- -1 acetoacetoxyethyl Chemical group 0.000 claims description 14
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 14
- 229940035893 uracil Drugs 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005543 phthalimide group Chemical group 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical group O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 1
- 239000000976 ink Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 19
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 17
- 238000004040 coloring Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 6
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- QINYBRXZAIWZBM-UHFFFAOYSA-N 2-(3-oxobutanoylamino)benzoic acid Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(O)=O QINYBRXZAIWZBM-UHFFFAOYSA-N 0.000 description 4
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UWLNKHDLVZEYKQ-UHFFFAOYSA-N 4-chloro-3-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(S(O)(=O)=O)=CC=C1Cl UWLNKHDLVZEYKQ-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 238000003916 acid precipitation Methods 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229940075420 xanthine Drugs 0.000 description 2
- UXOXUHMFQZEAFR-UHFFFAOYSA-N 2,2',5,5'-Tetrachlorobenzidine Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1C1=CC(Cl)=C(N)C=C1Cl UXOXUHMFQZEAFR-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- HXFNXEIKMAEASE-UHFFFAOYSA-N 4-(4-amino-3-chlorophenyl)-2-chloroaniline;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HXFNXEIKMAEASE-UHFFFAOYSA-N 0.000 description 1
- VFMNIJOKAXPZLE-UHFFFAOYSA-N 4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1 VFMNIJOKAXPZLE-UHFFFAOYSA-N 0.000 description 1
- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 description 1
- LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 description 1
- ZFTBZKVVGZNMJR-UHFFFAOYSA-N 5-chlorouracil Chemical compound ClC1=CNC(=O)NC1=O ZFTBZKVVGZNMJR-UHFFFAOYSA-N 0.000 description 1
- TUARVSWVPPVUGS-UHFFFAOYSA-N 5-nitrouracil Chemical compound [O-][N+](=O)C1=CNC(=O)NC1=O TUARVSWVPPVUGS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical group C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000001052 yellow pigment Substances 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/037—Disazo dyes characterised by two coupling components of different types
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006199730A JP5175038B2 (ja) | 2006-07-21 | 2006-07-21 | ジスアゾ顔料組成物 |
| PCT/JP2007/064064 WO2008010477A1 (fr) | 2006-07-21 | 2007-07-17 | Composition de pigment diazo |
| CN2007800270598A CN101490179B (zh) | 2006-07-21 | 2007-07-17 | 双偶氮颜料组合物 |
| TW96126577A TWI404765B (zh) | 2006-07-21 | 2007-07-20 | Disazo pigment composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006199730A JP5175038B2 (ja) | 2006-07-21 | 2006-07-21 | ジスアゾ顔料組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008024844A JP2008024844A (ja) | 2008-02-07 |
| JP5175038B2 true JP5175038B2 (ja) | 2013-04-03 |
Family
ID=38956808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006199730A Expired - Fee Related JP5175038B2 (ja) | 2006-07-21 | 2006-07-21 | ジスアゾ顔料組成物 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5175038B2 (fr) |
| CN (1) | CN101490179B (fr) |
| TW (1) | TWI404765B (fr) |
| WO (1) | WO2008010477A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5764890B2 (ja) * | 2010-09-15 | 2015-08-19 | 東洋インキＳｃホールディングス株式会社 | ジスアゾ顔料組成物の製造方法および印刷インキ組成物 |
| JP5232973B2 (ja) * | 2011-11-02 | 2013-07-10 | 東洋インキＳｃホールディングス株式会社 | ジスアゾ顔料組成物およびその製造方法、印刷インキ組成物 |
| CN103087544A (zh) * | 2011-11-07 | 2013-05-08 | 南京工业大学 | 一种对苯二胺系双偶氮有机颜料及其制备方法 |
| CN105143353B (zh) * | 2013-04-26 | 2017-03-15 | 东洋油墨Sc控股株式会社 | 双偶氮颜料组合物及其制造方法 |
| CN104263002A (zh) * | 2014-08-19 | 2015-01-07 | 上虞市东海化工有限公司 | 一种黄色颜料的制备方法 |
| CN106349735B (zh) * | 2016-08-30 | 2017-09-05 | 上虞市东海化工有限公司 | 一种黄色颜料的制备方法 |
| CN106590016A (zh) * | 2016-12-06 | 2017-04-26 | 杭州荣彩实业有限公司 | 一种混晶型c.i.颜料黄12的生产方法 |
| CN107686686B (zh) * | 2017-08-15 | 2019-07-12 | 龙口联合化学有限公司 | 糖分子偶联二酮吡咯并吡咯化合物在制备喷墨记录用水性分散体的应用 |
| CN107603272B (zh) * | 2017-10-14 | 2019-04-26 | 龙口联合化学有限公司 | 糖分子偶联二酮吡咯并吡咯化合物在黄颜料制备中的应用、黄颜料及黄颜料的制备方法 |
| CN109627803B (zh) * | 2018-12-19 | 2020-05-19 | 山东世纪阳光科技有限公司 | 环保型有机颜料联苯胺黄g的生产方法 |
| CN110003682A (zh) * | 2019-03-13 | 2019-07-12 | 龙口祥耀化学科技有限公司 | 一种油墨用永固黄颜料的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3173103B2 (ja) * | 1992-03-18 | 2001-06-04 | 大日本インキ化学工業株式会社 | ジスアゾ顔料 |
| JPH07304985A (ja) * | 1994-05-10 | 1995-11-21 | Dainippon Ink & Chem Inc | 黄色顔料組成物 |
| JP4536912B2 (ja) * | 2000-12-08 | 2010-09-01 | 大日精化工業株式会社 | ジスアゾ顔料組成物及び印刷インキ組成物 |
-
2006
- 2006-07-21 JP JP2006199730A patent/JP5175038B2/ja not_active Expired - Fee Related
-
2007
- 2007-07-17 CN CN2007800270598A patent/CN101490179B/zh active Active
- 2007-07-17 WO PCT/JP2007/064064 patent/WO2008010477A1/fr active Application Filing
- 2007-07-20 TW TW96126577A patent/TWI404765B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101490179A (zh) | 2009-07-22 |
| CN101490179B (zh) | 2013-05-08 |
| TWI404765B (zh) | 2013-08-11 |
| TW200813164A (en) | 2008-03-16 |
| JP2008024844A (ja) | 2008-02-07 |
| WO2008010477A1 (fr) | 2008-01-24 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| LAPS | Cancellation because of no payment of annual fees |