DE2202143C3 - Verfahren zur Herstellung leicht verteilbarer Azopigmente - Google Patents
Verfahren zur Herstellung leicht verteilbarer AzopigmenteInfo
- Publication number
- DE2202143C3 DE2202143C3 DE2202143A DE2202143A DE2202143C3 DE 2202143 C3 DE2202143 C3 DE 2202143C3 DE 2202143 A DE2202143 A DE 2202143A DE 2202143 A DE2202143 A DE 2202143A DE 2202143 C3 DE2202143 C3 DE 2202143C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- solution
- minutes
- stirred
- acid
- 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 33
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 230000008878 coupling Effects 0.000 claims description 21
- 238000010168 coupling process Methods 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 17
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 14
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 12
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 19
- 238000007639 printing Methods 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000012670 alkaline solution Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 9
- 239000001054 red pigment Substances 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000006193 diazotization reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 239000001110 calcium chloride Substances 0.000 description 7
- 229910001628 calcium chloride Inorganic materials 0.000 description 7
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 229960000878 docusate sodium Drugs 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 aliphatic Amines Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- SOSQXPIKTBUEKF-UHFFFAOYSA-N 1,4-dihexoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCC SOSQXPIKTBUEKF-UHFFFAOYSA-N 0.000 description 1
- OXLXSOPFNVKUMU-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC OXLXSOPFNVKUMU-UHFFFAOYSA-N 0.000 description 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
- GLKSLQGFGAMTOV-UHFFFAOYSA-N 4-decoxy-4-oxo-3-sulfobutanoic acid Chemical compound CCCCCCCCCCOC(=O)C(S(O)(=O)=O)CC(O)=O GLKSLQGFGAMTOV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCUJUFDOQOJLBE-UHFFFAOYSA-N [Cl].[Ca] Chemical compound [Cl].[Ca] UCUJUFDOQOJLBE-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2202143A DE2202143C3 (de) | 1972-01-18 | 1972-01-18 | Verfahren zur Herstellung leicht verteilbarer Azopigmente |
| GB673A GB1411711A (en) | 1972-01-18 | 1973-01-01 | Process for the production of easily dispersible laked azo pigments |
| US00322204A US3841889A (en) | 1972-01-18 | 1973-01-09 | Process for the production of easily laked azo pigments |
| AU50882/73A AU483573B2 (en) | 1972-01-18 | 1973-01-09 | Process forthe production of easily dispersible laked azo pigments |
| NL7300510A NL7300510A (OSRAM) | 1972-01-18 | 1973-01-12 | |
| CH51673A CH569067A5 (OSRAM) | 1972-01-18 | 1973-01-15 | |
| IT47697/73A IT976893B (it) | 1972-01-18 | 1973-01-15 | Procedimento per la produzione di pigmenti azoici facilmente suddivisibili |
| DK25473A DK140105C (da) | 1972-01-18 | 1973-01-17 | Fremgangsmaade til fremstilling af let fordelelige,forlakkede azopigmenter |
| JP48007115A JPS4879832A (OSRAM) | 1972-01-18 | 1973-01-17 | |
| ES410700A ES410700A1 (es) | 1972-01-18 | 1973-01-17 | Procedimiento para la obtencion de pigmentos azoicos enla- cados, facilmente distribuibles. |
| BR73384A BR7300384D0 (pt) | 1972-01-18 | 1973-01-17 | Processo para fabricacao de azo-pigmentos em forma de lacas facilmente dispersiveis ao estado de fina dispensao |
| FR7301717A FR2168484B3 (OSRAM) | 1972-01-18 | 1973-01-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2202143A DE2202143C3 (de) | 1972-01-18 | 1972-01-18 | Verfahren zur Herstellung leicht verteilbarer Azopigmente |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2202143A1 DE2202143A1 (de) | 1973-07-26 |
| DE2202143B2 DE2202143B2 (de) | 1979-07-19 |
| DE2202143C3 true DE2202143C3 (de) | 1980-03-27 |
Family
ID=5833264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2202143A Expired DE2202143C3 (de) | 1972-01-18 | 1972-01-18 | Verfahren zur Herstellung leicht verteilbarer Azopigmente |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3841889A (OSRAM) |
| JP (1) | JPS4879832A (OSRAM) |
| BR (1) | BR7300384D0 (OSRAM) |
| CH (1) | CH569067A5 (OSRAM) |
| DE (1) | DE2202143C3 (OSRAM) |
| DK (1) | DK140105C (OSRAM) |
| ES (1) | ES410700A1 (OSRAM) |
| FR (1) | FR2168484B3 (OSRAM) |
| GB (1) | GB1411711A (OSRAM) |
| IT (1) | IT976893B (OSRAM) |
| NL (1) | NL7300510A (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2340357A1 (fr) * | 1976-02-04 | 1977-09-02 | Ugine Kuhlmann | Compositions pigmentaires a base d'esters d'acides resiniques et d'amino-alcools |
| DE69519411T2 (de) * | 1994-09-14 | 2001-03-29 | Ciba Specialty Chemicals Holding Inc., Basel | Vermischbare organische Pigmente |
| DE69526472T2 (de) * | 1994-09-14 | 2002-11-28 | Ciba Speciality Chemicals Holding Inc., Basel | Vermischbare organische Pigmente |
| US5762757A (en) * | 1996-12-05 | 1998-06-09 | Betzdearborn Inc. | Methods for inhibiting organic contaminant deposition in pulp and papermaking systems |
| US7465348B1 (en) * | 2007-06-07 | 2008-12-16 | Xerox Corporation | Nanosized particles of monoazo laked pigment |
| US7563318B1 (en) * | 2008-07-02 | 2009-07-21 | Xerox Corporation | Method of making nanoscale particles of AZO pigments in a microreactor or micromixer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2455898A (en) * | 1943-12-10 | 1948-12-07 | American Cyanamid Co | Lakes of basic dyestuffs |
| US2772983A (en) * | 1952-10-20 | 1956-12-04 | Du Pont | Organic pigment production |
| US2811515A (en) * | 1955-02-02 | 1957-10-29 | Geigy Ag J R | Lakes and the production thereof |
| US3444157A (en) * | 1964-03-16 | 1969-05-13 | Dainichiseika Color Chem | Process for the manufacture of aqueous azo and basic lake pigments |
-
1972
- 1972-01-18 DE DE2202143A patent/DE2202143C3/de not_active Expired
-
1973
- 1973-01-01 GB GB673A patent/GB1411711A/en not_active Expired
- 1973-01-09 US US00322204A patent/US3841889A/en not_active Expired - Lifetime
- 1973-01-12 NL NL7300510A patent/NL7300510A/xx not_active Application Discontinuation
- 1973-01-15 IT IT47697/73A patent/IT976893B/it active
- 1973-01-15 CH CH51673A patent/CH569067A5/xx not_active IP Right Cessation
- 1973-01-17 ES ES410700A patent/ES410700A1/es not_active Expired
- 1973-01-17 JP JP48007115A patent/JPS4879832A/ja active Pending
- 1973-01-17 BR BR73384A patent/BR7300384D0/pt unknown
- 1973-01-17 DK DK25473A patent/DK140105C/da not_active IP Right Cessation
- 1973-01-18 FR FR7301717A patent/FR2168484B3/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK140105B (da) | 1979-06-18 |
| ES410700A1 (es) | 1976-01-01 |
| US3841889A (en) | 1974-10-15 |
| CH569067A5 (OSRAM) | 1975-11-14 |
| NL7300510A (OSRAM) | 1973-07-20 |
| FR2168484B3 (OSRAM) | 1976-01-23 |
| AU5088273A (en) | 1974-07-11 |
| DK140105C (da) | 1979-11-12 |
| DE2202143A1 (de) | 1973-07-26 |
| BR7300384D0 (pt) | 1973-09-20 |
| GB1411711A (en) | 1975-10-29 |
| FR2168484A1 (OSRAM) | 1973-08-31 |
| DE2202143B2 (de) | 1979-07-19 |
| IT976893B (it) | 1974-09-10 |
| JPS4879832A (OSRAM) | 1973-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |