DE2122521C3 - Modifiziertes Diarylidpigment und Verfahren zu seiner Herstellung - Google Patents
Modifiziertes Diarylidpigment und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2122521C3 DE2122521C3 DE19712122521 DE2122521A DE2122521C3 DE 2122521 C3 DE2122521 C3 DE 2122521C3 DE 19712122521 DE19712122521 DE 19712122521 DE 2122521 A DE2122521 A DE 2122521A DE 2122521 C3 DE2122521 C3 DE 2122521C3
- Authority
- DE
- Germany
- Prior art keywords
- pigment
- parts
- water
- coupling
- dye
- 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
- 239000000049 pigment Substances 0.000 title claims description 82
- 238000000034 method Methods 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 9
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- JCUYNPHEESTECG-UHFFFAOYSA-N 3-amino-6-(4-aminophenyl)benzene-1,2-disulfonic acid Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(S(O)(=O)=O)=C1S(O)(=O)=O JCUYNPHEESTECG-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 238000005859 coupling reaction Methods 0.000 description 40
- 230000008878 coupling Effects 0.000 description 39
- 238000010168 coupling process Methods 0.000 description 39
- 239000000975 dye Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 24
- 239000002002 slurry Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000976 ink Substances 0.000 description 16
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000000725 suspension Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 238000007639 printing Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- -1 fatty acid ester Chemical class 0.000 description 9
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 8
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 3
- 239000012260 resinous material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical class CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- 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 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SCJGEQJKHIPEPC-UHFFFAOYSA-N N,N-dichloro-4-[4-(dichloroamino)phenyl]aniline Chemical class ClN(C1=CC=C(C2=CC=C(N(Cl)Cl)C=C2)C=C1)Cl SCJGEQJKHIPEPC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- XNASJHUIUYZLKX-UHFFFAOYSA-N dodecanoic acid;2-(2-hydroxypropoxy)propan-1-ol Chemical compound CC(O)COC(C)CO.CCCCCCCCCCCC(O)=O XNASJHUIUYZLKX-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
-
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H71/00—Details of the protective switches or relays covered by groups H01H73/00 - H01H83/00
- H01H71/10—Operating or release mechanisms
- H01H71/50—Manual reset mechanisms which may be also used for manual release
- H01H71/52—Manual reset mechanisms which may be also used for manual release actuated by lever
- H01H71/529—Manual reset mechanisms which may be also used for manual release actuated by lever comprising an electroresponsive element forming part of the transmission chain between handle and contact arm
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H71/00—Details of the protective switches or relays covered by groups H01H73/00 - H01H83/00
- H01H71/10—Operating or release mechanisms
- H01H71/12—Automatic release mechanisms with or without manual release
- H01H71/40—Combined electrothermal and electromagnetic mechanisms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Coloring (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2175470A GB1356253A (en) | 1970-05-06 | 1970-05-06 | Azo pigment compositions |
| GB3442970 | 1970-07-16 | ||
| GB3442870 | 1970-07-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2122521A1 DE2122521A1 (de) | 1971-12-02 |
| DE2122521B2 DE2122521B2 (de) | 1981-01-08 |
| DE2122521C3 true DE2122521C3 (de) | 1988-02-11 |
Family
ID=27258033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712122521 Expired DE2122521C3 (de) | 1970-05-06 | 1971-05-06 | Modifiziertes Diarylidpigment und Verfahren zu seiner Herstellung |
Country Status (10)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1425522A (en) * | 1973-01-17 | 1976-02-18 | Ciba Geigy Ag | Pigments compositions containing azoarylamides |
| US4057436A (en) * | 1974-09-17 | 1977-11-08 | Imperial Chemical Industries Limited | Dispersion of solids in organic solvents |
| AT355692B (de) * | 1978-01-24 | 1980-03-10 | Basf Farben & Fasern | Verfahren zur herstellung von im glanz bzw. deckvermoegen verbesserten pigmentzusammen- setzungen |
| US4341701A (en) | 1979-11-07 | 1982-07-27 | Ciba-Geigy Corporation | Production of pigments |
| NZ201300A (en) * | 1981-08-11 | 1985-12-13 | Ici Plc | Pigment:fluidising compositions containing disazo compounds |
| US4468255A (en) * | 1983-08-10 | 1984-08-28 | Sun Chemical Corporation | Rheology modifiers for arylide yellow pigment dispersions and pigment dispersions containing same |
| DE3329846A1 (de) * | 1983-08-18 | 1985-02-28 | Basf Farben + Fasern Ag, 2000 Hamburg | Modifizierte diarylidpigmente und verfahren zu ihrer herstellung |
| DE3434379A1 (de) * | 1984-09-19 | 1986-03-20 | Basf Farben + Fasern Ag, 2000 Hamburg | Pigmentzubereitungen |
| DE3506474A1 (de) * | 1985-02-23 | 1986-08-28 | Bayer Ag, 5090 Leverkusen | Mischungen aus disazopigmenten und loeslichen farbstoffen |
| US4680057A (en) * | 1985-04-12 | 1987-07-14 | Basf Corporation, Inmont Division | Easily flushable transparent, strong diarylide yellow pigment compositions |
| EP0278913A3 (de) * | 1987-02-12 | 1991-06-05 | Ciba-Geigy Ag | Neue Stoffzusammensetzungen auf der Basis von Metallkomplexpigmenten sowie neue Verbindungen |
| US4885033A (en) * | 1987-10-03 | 1989-12-05 | Ciba-Geigy Corporation | Pigment compositions based on acetoacetarylide derivatives |
| US4968352A (en) * | 1988-04-28 | 1990-11-06 | Hoechst Celanese Corporation | Diaryl pigments with improved heat stability and transparency containing coupled mixed bis-diazotized diamines and acid-substituted aromatic amines |
| US5034063A (en) * | 1988-10-21 | 1991-07-23 | Toyo Ink Manufacturing Co., Ltd. | Dispersant-containing disazo pigment composition |
| GB9007284D0 (en) * | 1990-03-31 | 1990-05-30 | Ciba Geigy Ag | Production of pigments |
| US5306342A (en) * | 1991-06-06 | 1994-04-26 | Ciba-Geigy Corporation | Production of pigments |
| GB9112155D0 (en) * | 1991-06-06 | 1991-07-24 | Ciba Geigy Ag | Production of pigments |
| US5246494A (en) * | 1991-07-23 | 1993-09-21 | Engelhard Corporation | Mixed coupled azo pigments |
| GB9117292D0 (en) * | 1991-08-09 | 1991-09-25 | Ciba Geigy Ag | Coupling process |
| DE4440928A1 (de) * | 1994-11-17 | 1996-05-23 | Hoechst Ag | Pigmentzubereitungen auf Basis von Monoazopigmenten |
| IN192574B (enrdf_load_stackoverflow) * | 1996-08-08 | 2004-05-01 | Dainippon Ink & Chemicals | |
| US5972099A (en) * | 1997-12-17 | 1999-10-26 | Bayer Corporation | Process for preparing organic pigment compositions |
| US5922123A (en) * | 1997-12-17 | 1999-07-13 | Bayer Corporation | Method for conditioning organic pigments |
| GB9920107D0 (en) * | 1999-08-26 | 1999-10-27 | Avecia Ltd | Fluidising agents |
| JP2005523985A (ja) * | 2002-04-29 | 2005-08-11 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | インク及び塗料のベースとなる顔料に対して、改良された流動性（レオロジー）を付与するための組成物及び方法 |
| US7223302B2 (en) * | 2003-01-17 | 2007-05-29 | Cabot Corporation | Methods of preparing aqueous colored pigment dispersions, and inkjet ink compositions |
| US7300504B2 (en) | 2003-10-20 | 2007-11-27 | Cabot Corporation | Inkjet inks and methods of preparing the same |
| US20080282931A1 (en) * | 2003-11-11 | 2008-11-20 | Stuart Cook Niven | Pigment Compositions for Oil-Based Lithographic Printing Ink System |
| JP6720182B2 (ja) | 2014-12-17 | 2020-07-08 | ピルキントン グループ リミテッド | 炉 |
| WO2022000131A1 (en) * | 2020-06-28 | 2022-01-06 | Dic Corporation | Disazo pigment, pigment composition, and printing ink |
| CN118909458A (zh) * | 2024-07-04 | 2024-11-08 | 瑞安宝源化工有限公司 | 一种3d酸改性联苯胺类有机颜料及其制备方法与应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526345A (en) * | 1946-02-23 | 1950-10-17 | Interchem Corp | Phthalocyanine pigment compositions |
| DE1155755B (de) * | 1960-05-28 | 1963-10-17 | Hoechst Ag | Verfahren zur Herstellung von Azopigmenten mit verbesserter Fliessbarkeit |
| DE1179908B (de) * | 1960-12-02 | 1964-10-22 | Hoechst Ag | Verfahren zur Herstellung von Azopigmenten mit verbesserter Fliessarbeit |
| US3336147A (en) * | 1963-08-12 | 1967-08-15 | Ici Ltd | Manufacture of pigment compositions |
| GB1096362A (en) * | 1965-06-01 | 1967-12-29 | Ici Ltd | Azoacylacetarylamide/amine condensation products |
| FR90694E (enrdf_load_stackoverflow) * | 1965-08-14 | 1968-04-05 | ||
| GB1138465A (en) * | 1965-08-16 | 1969-01-01 | Ici Ltd | Pigment compositions |
| DE1469740A1 (de) * | 1965-10-08 | 1969-01-02 | Hoechst Ag | Verfahren zur Behandlung eines Azopigmentes |
| GB1229990A (enrdf_load_stackoverflow) * | 1968-06-05 | 1971-04-28 | ||
| DE1936311B1 (de) * | 1969-07-17 | 1970-12-23 | Siegle & Co Gmbh G | Verfahren zur Herstellung leicht dispergierbarer Pigmente fuer Druckfarbenfirnisse auf Aromatenbasis |
| DE2012152C3 (de) * | 1970-03-14 | 1974-03-21 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von Pigmentfarbstoffgemischen aus Disazofarbstoffen und deren Verwendung |
-
1970
- 1970-05-06 GB GB2175470A patent/GB1356253A/en not_active Expired
-
1971
- 1971-05-03 DK DK213871A patent/DK151971C/da not_active IP Right Cessation
- 1971-05-04 MX MX12704071A patent/MX147807A/es unknown
- 1971-05-05 ES ES390896A patent/ES390896A1/es not_active Expired
- 1971-05-05 NL NL7106167A patent/NL173973C/xx not_active IP Right Cessation
- 1971-05-05 AT AT391371A patent/AT312123B/de not_active IP Right Cessation
- 1971-05-05 CH CH666571A patent/CH579623A5/xx not_active IP Right Cessation
- 1971-05-06 JP JP3008471A patent/JPS5737623B1/ja active Pending
- 1971-05-06 FR FR7116408A patent/FR2091301A5/fr not_active Expired
- 1971-05-06 DE DE19712122521 patent/DE2122521C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7106167A (enrdf_load_stackoverflow) | 1971-11-09 |
| DK151971B (da) | 1988-01-18 |
| NL173973C (nl) | 1984-04-02 |
| MX147807A (es) | 1983-01-13 |
| DE2122521B2 (de) | 1981-01-08 |
| DE2122521A1 (de) | 1971-12-02 |
| FR2091301A5 (enrdf_load_stackoverflow) | 1972-01-14 |
| GB1356253A (en) | 1974-06-12 |
| DK151971C (da) | 1988-07-18 |
| CH579623A5 (enrdf_load_stackoverflow) | 1976-09-15 |
| AT312123B (de) | 1973-12-27 |
| ES390896A1 (es) | 1974-04-01 |
| JPS5737623B1 (enrdf_load_stackoverflow) | 1982-08-11 |
| NL173973B (nl) | 1983-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2122521C3 (de) | Modifiziertes Diarylidpigment und Verfahren zu seiner Herstellung | |
| EP0538784B1 (de) | Pigmentzubereitungen | |
| DE2135468B2 (de) | Pigmentzusammensetzung, Verfahren zu deren Herstellung und deren Verwendung | |
| DE2856222C3 (de) | Wäßrige Farbstoffpräparate von in Wasser schwerlöslichen Farbstoffen, deren Herstellung und Verwendung | |
| DE69107106T2 (de) | Verfahren zur Herstellung von Pigmenten. | |
| DE69127540T2 (de) | Monoazopigmentzusammensetzungen | |
| DE2855943C3 (de) | Verfahren zur Herstellung von Pigmentzusammensetzungen und deren Verwendung | |
| EP0311560A2 (de) | Pigmentzusammensetzungen auf Basis von Acetoacetaryliden | |
| EP0033913B1 (de) | Verfahren zur Herstellung von Pigmentpräparationen und ihre Verwendung | |
| DE2625335A1 (de) | Kristallines lineares chinacridon und verfahren zu dessen herstellung | |
| DE2006707B2 (enrdf_load_stackoverflow) | ||
| EP0033297A1 (de) | Färbestabiler Dispersionsfarbstoff und dessen Verwendung zum Färben und Bedrucken synthetischer und halbsynthetischer Fasermaterialien | |
| DE3873252T2 (de) | Pigment von hoher staerke zur verwendung in drucktinten. | |
| DE2913007C2 (enrdf_load_stackoverflow) | ||
| DE2302481A1 (de) | Disazopigment, verfahren zu seiner herstellung und seine verwendung | |
| EP0796900A2 (de) | Für wasserverdünnbare Druckfarben und Lacke geeignete Pigmentzubereitungen | |
| DE2704362A1 (de) | Pigmentzubereitungen auf der basis von estern von harzsaeuren und von aminoalkoholen und verfahren zu ihrer herstellung | |
| EP0139944B1 (de) | Modifizierte Diarylidpigmente und Verfahren zu ihrer Herstellung | |
| DE2705107C2 (enrdf_load_stackoverflow) | ||
| DE1619618C3 (de) | Chinacridon-Pigmentmasse | |
| DE1769443C3 (de) | Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Druckfarben | |
| DE2811539A1 (de) | Verfahren zur konditionierung eines phthalocyaninpigments | |
| DE2830154C2 (de) | Azofarbstoffe | |
| DE2312301C3 (de) | Leichtverteilbare Pigmentzubereitungen | |
| DE3023330A1 (de) | Farbstoffmischungen, verfahren zu deren herstellung und zum faerben von hydrophoben fasern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8263 | Opposition against grant of a patent | ||
| 8228 | New agent |
Free format text: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR.RER.NAT. ZUMSTEIN JUN., F., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| C3 | Grant after two publication steps (3rd publication) |