CA1045121A - Preparation de pigments diazoiques - Google Patents

Preparation de pigments diazoiques

Info

Publication number: CA1045121A
Authority: CA; Canada
Prior art keywords: parts; coupling; acid; pigment; solution
Prior art date: 1974-04-29
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

Application number

CA225,502A

Other languages

English (en)

Other versions

CA225502S (en

Inventor

Paul Muller

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1974-04-29

Filing date

1975-04-25

Publication date

1978-12-26

1975-04-25 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1978-12-26 Application granted granted Critical

1978-12-26 Publication of CA1045121A publication Critical patent/CA1045121A/fr

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title claims abstract description 20
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title abstract description 7
230000008569 process Effects 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title abstract description 5
239000004922 lacquer Substances 0.000 abstract description 3
229920003023 plastic Polymers 0.000 abstract description 2
239000004033 plastic Substances 0.000 abstract description 2
GTRGJJDVSJFNTE-UHFFFAOYSA-N chembl2009633 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 GTRGJJDVSJFNTE-UHFFFAOYSA-N 0.000 abstract 1
238000004040 coloring Methods 0.000 abstract 1
238000010168 coupling process Methods 0.000 description 26
230000008878 coupling Effects 0.000 description 25
238000005859 coupling reaction Methods 0.000 description 25
239000000243 solution Substances 0.000 description 23
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000003086 colorant Substances 0.000 description 11
-1 phosphorus halides Chemical class 0.000 description 11
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012860 organic pigment Substances 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000002156 mixing Methods 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 6
ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
238000009833 condensation Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
230000005012 migration Effects 0.000 description 4
238000013508 migration Methods 0.000 description 4
229920000915 polyvinyl chloride Polymers 0.000 description 4
239000004800 polyvinyl chloride Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
229940117389 dichlorobenzene Drugs 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000001053 orange pigment Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
229920000180 alkyd Polymers 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ZJWAGKRIOBSJHQ-NTSYASGDSA-N (z,12r)-1-butoxy-12-hydroxy-1-oxooctadec-9-ene-2-sulfonic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCC(S(O)(=O)=O)C(=O)OCCCC ZJWAGKRIOBSJHQ-NTSYASGDSA-N 0.000 description 1
MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
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
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000005030 aluminium foil Substances 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
229920003180 amino resin Polymers 0.000 description 1
229960003116 amyl nitrite Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920001727 cellulose butyrate Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
IIGAELMXVLEZPM-GRVYQHKQSA-L cobalt(2+);(9z,12z)-octadeca-9,12-dienoate Chemical compound [Co+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O IIGAELMXVLEZPM-GRVYQHKQSA-L 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000012505 colouration Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
238000001914 filtration Methods 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000000976 ink Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000004988 m-phenylenediamines Chemical class 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
239000000155 melt Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000000485 pigmenting effect Effects 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000007639 printing Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000000080 wetting agent 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
- C09B43/38—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines by reacting two or more ortho-hydroxy naphthoic acid dyes with polyamines
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/147—Disazo dyes in which the coupling component is a bis -(-o-hydroxy-carboxylic- acid amide)

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Compositions Of Macromolecular Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paints Or Removers (AREA)

CA225,502A 1974-04-29 1975-04-25 Preparation de pigments diazoiques Expired CA1045121A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH587474A CH598330A5 (fr)	1974-04-29	1974-04-29

Publications (1)

Publication Number	Publication Date
CA1045121A true CA1045121A (fr)	1978-12-26

Family

ID=4300761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA225,502A Expired CA1045121A (fr)	1974-04-29	1975-04-25	Preparation de pigments diazoiques

Country Status (11)

Country	Link
JP (1)	JPS50149722A (fr)
AR (1)	AR206343A1 (fr)
BE (1)	BE828465A (fr)
BR (1)	BR7502572A (fr)
CA (1)	CA1045121A (fr)
CH (1)	CH598330A5 (fr)
DE (1)	DE2518560A1 (fr)
ES (1)	ES437096A1 (fr)
FR (1)	FR2268845B1 (fr)
GB (1)	GB1450026A (fr)
NL (1)	NL7505098A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0090777A1 (fr) *	1982-03-31	1983-10-05	Ciba-Geigy Ag	Pigments disazoiques, procédés pour leur préparation et leur utilisation
JP6368844B1 (ja) *	2017-08-25	2018-08-01	東洋インキＳｃホールディングス株式会社	アゾ顔料、カラーフィルタ用着色剤、着組成物およびカラーフィルタ

1974
- 1974-04-29 CH CH587474A patent/CH598330A5/xx not_active IP Right Cessation
1975
- 1975-01-01 AR AR25852775A patent/AR206343A1/es active
- 1975-04-25 DE DE19752518560 patent/DE2518560A1/de active Pending
- 1975-04-25 CA CA225,502A patent/CA1045121A/fr not_active Expired
- 1975-04-28 BE BE155840A patent/BE828465A/fr unknown
- 1975-04-28 GB GB1750775A patent/GB1450026A/en not_active Expired
- 1975-04-28 FR FR7513177A patent/FR2268845B1/fr not_active Expired
- 1975-04-28 ES ES437096A patent/ES437096A1/es not_active Expired
- 1975-04-28 BR BR7503262A patent/BR7502572A/pt unknown
- 1975-04-29 NL NL7505098A patent/NL7505098A/xx not_active Application Discontinuation
- 1975-04-30 JP JP5243875A patent/JPS50149722A/ja active Pending

Also Published As

Publication number	Publication date
ES437096A1 (es)	1977-02-01
CH598330A5 (fr)	1978-04-28
GB1450026A (en)	1976-09-22
FR2268845B1 (fr)	1977-04-15
BE828465A (fr)	1975-10-28
JPS50149722A (fr)	1975-12-01
FR2268845A1 (fr)	1975-11-21
NL7505098A (nl)	1975-10-31
AU8054875A (en)	1976-10-28
BR7502572A (pt)	1976-03-09
AR206343A1 (es)	1976-07-15
DE2518560A1 (de)	1975-11-13

Publication	Publication Date	Title
JP2637731B2 (ja)	1997-08-06	有機顔料及びその製造方法
CA1040626A (fr)	1978-10-17	Pigments bisazoiques
US4003886A (en)	1977-01-18	Tetracarboxylic acid ester substituted disazo pigments
US3872078A (en)	1975-03-18	Disazo pigments, processes for their manufacture and use
US4220586A (en)	1980-09-02	Hetero-aryl azo acylamino substituted aceto-acetarylide pigments
US3963694A (en)	1976-06-15	Hydroxyquinolyl- and quinazolonylazoacetoacetylbenzimidazolone pigments
CA1108605A (fr)	1981-09-08	Procede d'obtention de pigments monoazoiques
USRE27575E (en)	1973-02-06	Water-insoluble benzimidazolone containing monoazo dyestuffs
US3923774A (en)	1975-12-02	Quinazolone containing phenyl-azo-pyridine compounds
US4024124A (en)	1977-05-17	Monoazo acetoacetylaminobenzimidazolone pigments containing carboxy group
US4400319A (en)	1983-08-23	Monoazo pigments containing heterocycles, and high-molecular organic materials dyed therewith
US3555002A (en)	1971-01-12	Water-insoluble benzimidazolone containing monoazo dyestuffs
US4100156A (en)	1978-07-11	Chlorine-containing disaza pigments
US4055559A (en)	1977-10-25	Disazo pigment containing at least 2 chlorine atoms and process for their manufacture
US4206114A (en)	1980-06-03	Monoazo pigments from diazotized 5-acylaminoanthranilic acid derivatives and acetoacetylaminobenzimidazolones
US4065449A (en)	1977-12-27	Tetrachloro substituted disazo pigments
US4062838A (en)	1977-12-13	Disazo pigments containing acylamino groups
CA1227791A (fr)	1987-10-06	Pigmentation de matiere organique de forte masse moleculaire
US3963693A (en)	1976-06-15	Quinolone azo barbituric acid pigments
US3496190A (en)	1970-02-17	Bis-tetrachloro-isoindolin-1-on-3-ylidene-imino pigment
US4088641A (en)	1978-05-09	4-Methyl-5-(benzimidazolonylazo)-6-hydroxypyridone-2 pigment
CA1149800A (fr)	1983-07-12	Pigments diazoiques, procede de fabrication et applications
US4053464A (en)	1977-10-11	Disazo pigments containing ether substituted alkoxy carbonyl groups
US4005068A (en)	1977-01-25	Disazo compounds from diphenylene sulfones and acetoacetylbenzimidazolones
JPH06220341A (ja)	1994-08-09	新規なビスアゾ、ビスアゾメチンおよびアゾ−アゾメチン化合物