JPH01279978A - 染料の精製法 - Google Patents
染料の精製法Info
- Publication number
- JPH01279978A JPH01279978A JP63110978A JP11097888A JPH01279978A JP H01279978 A JPH01279978 A JP H01279978A JP 63110978 A JP63110978 A JP 63110978A JP 11097888 A JP11097888 A JP 11097888A JP H01279978 A JPH01279978 A JP H01279978A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- dye
- black
- purification
- insoluble matter
- 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
- 238000000746 purification Methods 0.000 title claims abstract description 19
- YCUVUDODLRLVIC-UHFFFAOYSA-N Sudan black B Chemical compound C1=CC(=C23)NC(C)(C)NC2=CC=CC3=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 YCUVUDODLRLVIC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003463 adsorbent Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 11
- 239000008096 xylene Substances 0.000 abstract description 11
- 238000001914 filtration Methods 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000012264 purified product Substances 0.000 abstract description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 6
- 239000012535 impurity Substances 0.000 abstract description 6
- 231100000419 toxicity Toxicity 0.000 abstract description 5
- 230000001988 toxicity Effects 0.000 abstract description 5
- 231100000053 low toxicity Toxicity 0.000 abstract description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005292 vacuum distillation Methods 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 28
- 238000010953 Ames test Methods 0.000 description 6
- 231100000039 Ames test Toxicity 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000007670 refining Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- -1 1,8-diaminonaphthalene - Dihydroperimidine Chemical compound 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 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
- 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
- C09B67/0096—Purification; Precipitation; Filtration
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63110978A JPH01279978A (ja) | 1988-05-06 | 1988-05-06 | 染料の精製法 |
| US07/344,372 US4927538A (en) | 1988-05-06 | 1989-04-28 | Purification of C.I. solvent black 3 |
| DE68917508T DE68917508T2 (de) | 1988-05-06 | 1989-05-05 | Reinigung des Farbstoffs C.I. solvent black 3. |
| EP89108160A EP0340792B1 (en) | 1988-05-06 | 1989-05-05 | Purification of C.I. solvent black 3 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63110978A JPH01279978A (ja) | 1988-05-06 | 1988-05-06 | 染料の精製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01279978A true JPH01279978A (ja) | 1989-11-10 |
| JPH0521148B2 JPH0521148B2 (enExample) | 1993-03-23 |
Family
ID=14549303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63110978A Granted JPH01279978A (ja) | 1988-05-06 | 1988-05-06 | 染料の精製法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4927538A (enExample) |
| EP (1) | EP0340792B1 (enExample) |
| JP (1) | JPH01279978A (enExample) |
| DE (1) | DE68917508T2 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008221624A (ja) * | 2007-03-13 | 2008-09-25 | Sumitomo Bakelite Co Ltd | 積層板、積層板の製造方法、および半導体装置 |
| JP2010132874A (ja) * | 2008-10-28 | 2010-06-17 | Sumitomo Chemical Co Ltd | 着色組成物の製造方法 |
| JP2011046921A (ja) * | 2009-07-30 | 2011-03-10 | Canon Inc | 着色粒子 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2798487B2 (ja) * | 1990-07-31 | 1998-09-17 | オリヱント化学工業株式会社 | 耐熱性および耐光性に優れたアジン系染料の製法 |
| US5393527A (en) * | 1993-01-04 | 1995-02-28 | Becton, Dickinson And Company | Stabilized microspheres and methods of preparation |
| US20080067124A1 (en) * | 2006-09-19 | 2008-03-20 | Kaczkowski Edward F | Solvent recovery system for plastic dying operation |
| JP2011084645A (ja) * | 2009-10-15 | 2011-04-28 | Seiko Epson Corp | インク組成物およびその製造方法 |
| TWI428402B (zh) * | 2010-10-15 | 2014-03-01 | Jinex Corp Ltd | 雙偶氮化合物及包含其之油墨及電溼潤顯示器 |
| RU2547741C2 (ru) * | 2012-11-07 | 2015-04-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Тамбовский государственный технический университет" ФГБОУ ВПО ТГТУ | Способ отмывки тонкодисперсных осадков на фильтрующей перегородке |
| CN105348848B (zh) * | 2015-11-20 | 2017-07-18 | 深圳市国华光电科技有限公司 | 一种双偶氮紫色染料及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1965842A (en) * | 1931-11-21 | 1934-07-10 | Nat Aniline & Chem Co Inc | Production of hydroxybenzenephthaleins |
| US2055685A (en) * | 1934-03-07 | 1936-09-29 | Nat Aniline & Chem Co Inc | Purification of dyestuffs |
| US4224071A (en) * | 1979-04-16 | 1980-09-23 | American Cyanamid Company | Black dyes for ball-point pen inks |
-
1988
- 1988-05-06 JP JP63110978A patent/JPH01279978A/ja active Granted
-
1989
- 1989-04-28 US US07/344,372 patent/US4927538A/en not_active Expired - Lifetime
- 1989-05-05 EP EP89108160A patent/EP0340792B1/en not_active Expired - Lifetime
- 1989-05-05 DE DE68917508T patent/DE68917508T2/de not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008221624A (ja) * | 2007-03-13 | 2008-09-25 | Sumitomo Bakelite Co Ltd | 積層板、積層板の製造方法、および半導体装置 |
| JP2010132874A (ja) * | 2008-10-28 | 2010-06-17 | Sumitomo Chemical Co Ltd | 着色組成物の製造方法 |
| JP2011046921A (ja) * | 2009-07-30 | 2011-03-10 | Canon Inc | 着色粒子 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0340792B1 (en) | 1994-08-17 |
| JPH0521148B2 (enExample) | 1993-03-23 |
| DE68917508D1 (de) | 1994-09-22 |
| EP0340792A2 (en) | 1989-11-08 |
| EP0340792A3 (en) | 1991-11-06 |
| DE68917508T2 (de) | 1995-02-02 |
| US4927538A (en) | 1990-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |