JPH0480033B2 - - Google Patents
Info
- Publication number
- JPH0480033B2 JPH0480033B2 JP1863787A JP1863787A JPH0480033B2 JP H0480033 B2 JPH0480033 B2 JP H0480033B2 JP 1863787 A JP1863787 A JP 1863787A JP 1863787 A JP1863787 A JP 1863787A JP H0480033 B2 JPH0480033 B2 JP H0480033B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- aminobenzotriazole
- hydroxyphenyl
- coupler
- pigment
- 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
Links
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000049 pigment Substances 0.000 description 62
- 239000000203 mixture Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000987 azo dye Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000006866 deterioration Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- ZDWPBMJZDNXTPG-UHFFFAOYSA-N 2h-benzotriazol-4-amine Chemical compound NC1=CC=CC2=C1NN=N2 ZDWPBMJZDNXTPG-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 210000003298 dental enamel Anatomy 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000012954 diazonium Substances 0.000 description 8
- 150000001989 diazonium salts Chemical class 0.000 description 8
- -1 naphthol compound Chemical class 0.000 description 8
- 229920000180 alkyd Polymers 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000000576 coating method Methods 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- 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 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- XSFHICWNEBCMNN-UHFFFAOYSA-N 2h-benzotriazol-5-amine Chemical class NC1=CC=C2NN=NC2=C1 XSFHICWNEBCMNN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- NCEXYHBECQHGNR-UHFFFAOYSA-N chembl421 Chemical compound C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000008268 mayonnaise Substances 0.000 description 2
- 235000010746 mayonnaise Nutrition 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
- XDWATWCCUTYUDE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=O)C1=CC2=CC=CC=C2C=C1O XDWATWCCUTYUDE-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005028 tinplate Substances 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SSKINQAQOGIXSW-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-4,6-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C(C)(C)(CC(C)(C)C)C=1C(=C(C=C(C=1)C(C)(C)CC(C)(C)C)N1N=C2C(=N1)C=CC(=C2)N)O SSKINQAQOGIXSW-UHFFFAOYSA-N 0.000 description 1
- WHLJGNYEWXNEAX-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(N2N=C3C=C(N)C=CC3=N2)=C1 WHLJGNYEWXNEAX-UHFFFAOYSA-N 0.000 description 1
- FCQLCYLEEMWNMA-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(N)C=CC3=N2)=C1O FCQLCYLEEMWNMA-UHFFFAOYSA-N 0.000 description 1
- ATGNDUMNXCRUNJ-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-6-(1-phenylethyl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C1=CC=CC=C1)C=1C(=C(C=C(C=1)C(C)(C)CC(C)(C)C)N1N=C2C(=N1)C=CC(=C2)N)O ATGNDUMNXCRUNJ-UHFFFAOYSA-N 0.000 description 1
- VNHYBBLSNMDROZ-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-6-benzyl-4-tert-butylphenol Chemical compound C(C1=CC=CC=C1)C=1C(=C(C=C(C=1)C(C)(C)C)N1N=C2C(=N1)C=CC(=C2)N)O VNHYBBLSNMDROZ-UHFFFAOYSA-N 0.000 description 1
- FWXOUGIGPVRHCZ-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-6-tert-butyl-4-methylphenol Chemical compound C(C)(C)(C)C=1C(=C(C=C(C=1)C)N1N=C2C(=N1)C=CC(=C2)N)O FWXOUGIGPVRHCZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1863787A JPS63188669A (ja) | 1987-01-30 | 1987-01-30 | カップラ− |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1863787A JPS63188669A (ja) | 1987-01-30 | 1987-01-30 | カップラ− |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63188669A JPS63188669A (ja) | 1988-08-04 |
| JPH0480033B2 true JPH0480033B2 (enrdf_load_html_response) | 1992-12-17 |
Family
ID=11977121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1863787A Granted JPS63188669A (ja) | 1987-01-30 | 1987-01-30 | カップラ− |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63188669A (enrdf_load_html_response) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI453199B (zh) | 2008-11-04 | 2014-09-21 | Alcon Inc | 用於眼用鏡片材料之紫外光／可見光吸收劑 |
| CN104497619A (zh) * | 2014-12-25 | 2015-04-08 | 上虞舜联化工有限公司 | 一种c.i.颜料棕25的制备方法 |
-
1987
- 1987-01-30 JP JP1863787A patent/JPS63188669A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63188669A (ja) | 1988-08-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4334932A (en) | Pigment formulations, processes for their preparation and their use for pigmenting aqueous, alcoholic or aqueous-alcoholic printing ink systems and colored lacquer systems | |
| US4666526A (en) | Azine pigments, processes for their preparation, and their use | |
| JPH0234664A (ja) | 黒色熱硬化性樹脂組成物 | |
| US4229344A (en) | Monazo pigments containing hydroxynaphthoylaminobenzimidazalone radical | |
| JPH0480033B2 (enrdf_load_html_response) | ||
| US4371467A (en) | Process for producing isoindolinone pigments | |
| EP0051560B1 (de) | Heterocyclen enthaltende Monoazopigmente, Verfahren zu deren Herstellung und deren Verwendung | |
| US5650515A (en) | Salts of metal-free anionic dyes having cations containing sterically hindered amine groups | |
| US3923777A (en) | Azo dye from an ortho-oxydiazolylaniline diazo component | |
| JPH0541666B2 (enrdf_load_html_response) | ||
| US4052410A (en) | Iminoisoindoline pigments | |
| EP0190692A2 (de) | Bis-isoindolinpigmente und ihre Verwendung | |
| US4847365A (en) | Metal complexes of substituted 4-(2-carboxy-phenylazo-5-pyrazolones | |
| US6132894A (en) | 1:2 Iron azo-dyestuff complexes | |
| US5298609A (en) | Disazo compounds containing cycloalkyl ester or cycloalkylamide groups | |
| JPH0480032B2 (enrdf_load_html_response) | ||
| JPH0621233B2 (ja) | 顔料組成物及びその製造方法 | |
| US4065448A (en) | Tertiary alkyl substituted disazo pigments | |
| JPH10152622A (ja) | ジスアゾ化合物およびジスアゾ顔料 | |
| DE4409902A1 (de) | Isoindolinazopigmente | |
| DE2322892A1 (de) | Neue dioxazinfarbstoffe und verfahren zu deren herstellung | |
| JPH0621234B2 (ja) | 顔料組成物及びその製造方法 | |
| US5194626A (en) | Metal complex pigments of azines | |
| DE2659676C2 (de) | Azoanthrachinonpigmente, deren Herstellung und Verwendung | |
| JPH0211663A (ja) | 複素環式ピグメントおよび染料 |