JPH0546869B2 - - Google Patents
Info
- Publication number
- JPH0546869B2 JPH0546869B2 JP27913685A JP27913685A JPH0546869B2 JP H0546869 B2 JPH0546869 B2 JP H0546869B2 JP 27913685 A JP27913685 A JP 27913685A JP 27913685 A JP27913685 A JP 27913685A JP H0546869 B2 JPH0546869 B2 JP H0546869B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- dinaphthylmethane
- dihydroxy
- hydroxy
- amino
- 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 claims description 41
- 230000008878 coupling Effects 0.000 claims description 25
- 238000010168 coupling process Methods 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 25
- -1 aromatic diazonium compound Chemical class 0.000 claims description 22
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical class CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000000976 ink Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical class CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000010187 litholrubine BK Nutrition 0.000 description 3
- 229940099800 pigment red 48 Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 2
- VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RQCHLUZDNJBPHV-UHFFFAOYSA-N 3-(aminomethyl)benzenesulfonic acid Chemical compound NCC1=CC=CC(S(O)(=O)=O)=C1 RQCHLUZDNJBPHV-UHFFFAOYSA-N 0.000 description 2
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 2
- NZTPZUIIYNYZKT-UHFFFAOYSA-N 6-aminonaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(N)=CC=C21 NZTPZUIIYNYZKT-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- PMJACRPIWSINFF-UHFFFAOYSA-N 1-methoxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(OC)=C(C(O)=O)C=CC2=C1 PMJACRPIWSINFF-UHFFFAOYSA-N 0.000 description 1
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- OSTYZAHQVPMQHI-UHFFFAOYSA-N 2-methoxynaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(OC)=CC=C21 OSTYZAHQVPMQHI-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- RTBQQRFTCVDODF-UHFFFAOYSA-N 3-methoxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(OC)=CC2=C1 RTBQQRFTCVDODF-UHFFFAOYSA-N 0.000 description 1
- JDQDSEVNMTYMOC-UHFFFAOYSA-N 3-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1 JDQDSEVNMTYMOC-UHFFFAOYSA-N 0.000 description 1
- HKCFHDMLRDLQSN-UHFFFAOYSA-N 4-chloro-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1Cl HKCFHDMLRDLQSN-UHFFFAOYSA-N 0.000 description 1
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
- YZBILXXOZFORFE-UHFFFAOYSA-N 6-Methoxy-2-naphthoic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OC)=CC=C21 YZBILXXOZFORFE-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60279136A JPS62138560A (ja) | 1985-12-13 | 1985-12-13 | アゾ顔料の製造法 |
| CA000501166A CA1236093A (en) | 1985-02-08 | 1986-02-05 | Process for producing azo pigments |
| DE8686300863T DE3668639D1 (de) | 1985-02-08 | 1986-02-07 | Verfahren zur herstellung von azopigmenten. |
| ES551740A ES8801176A1 (es) | 1985-02-08 | 1986-02-07 | Un procedimiento para producir un pigmento azoico |
| EP86300863A EP0190947B1 (en) | 1985-02-08 | 1986-02-07 | Process for producing azo pigments |
| KR1019860000884A KR910007083B1 (ko) | 1985-02-08 | 1986-02-08 | 아조 안료 제조방법 |
| US06/827,447 US4655844A (en) | 1985-02-08 | 1986-02-10 | Process for producing azo pigments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60279136A JPS62138560A (ja) | 1985-12-13 | 1985-12-13 | アゾ顔料の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62138560A JPS62138560A (ja) | 1987-06-22 |
| JPH0546869B2 true JPH0546869B2 (ko) | 1993-07-15 |
Family
ID=17606932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60279136A Granted JPS62138560A (ja) | 1985-02-08 | 1985-12-13 | アゾ顔料の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62138560A (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010033054A (ko) | 1998-10-16 | 2001-04-25 | 우에노 류조 | 조색제 |
-
1985
- 1985-12-13 JP JP60279136A patent/JPS62138560A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62138560A (ja) | 1987-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5176750A (en) | Azo pigment compositions and process for their preparation | |
| JPH06220351A (ja) | 溶剤系および水性インキシステム用顔料組成物ならびにその製造方法 | |
| JPH0459348B2 (ko) | ||
| EP0190947B1 (en) | Process for producing azo pigments | |
| JPH0546869B2 (ko) | ||
| KR20000062997A (ko) | 아조 레이크 안료 조성물 | |
| KR930010509B1 (ko) | 아조안료의 제조방법 | |
| JPH0546867B2 (ko) | ||
| EP0074117B1 (en) | Process for producing azo pigments | |
| US2237768A (en) | Production of azo colors | |
| JP2931115B2 (ja) | 顔料の製造方法 | |
| JPH0546868B2 (ko) | ||
| US4711674A (en) | Non-bronzing reddish lake pigment | |
| JPS6036224B2 (ja) | アゾ顔料の製造方法 | |
| JP4536912B2 (ja) | ジスアゾ顔料組成物及び印刷インキ組成物 | |
| JPS5929623B2 (ja) | アゾ顔料の製造方法 | |
| JPH0526832B2 (ko) | ||
| US2013084A (en) | Organic coloring materials comprising azo compounds and sulphonated derivatives of pyrogenic decomposition products of rosin | |
| JP3272949B2 (ja) | アゾレーキ顔料組成物及びその製造方法 | |
| JPH1088016A (ja) | アゾレーキ顔料組成物、その製造方法および顔料分散体 | |
| JPS62197460A (ja) | ジスアゾ黄色顔料の製造法 | |
| SU804674A1 (ru) | Способ получени моноазопигментовАцЕТОАцЕТАНилидНОгО Р дА | |
| JP3277122B2 (ja) | アゾレーキ顔料組成物及びその製造方法 | |
| SU604862A1 (ru) | Способ получени моноазопигмена-2окси-3-карбокси-(2-метокси-5-метиланилин)-нафталин-1-азо-1-(2-метокси-5бензамида) | |
| JPH1088020A (ja) | アゾレーキ顔料組成物、その製造方法および顔料分散体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |