GB803525A - Basic dyestuffs - Google Patents
Basic dyestuffsInfo
- Publication number
- GB803525A GB803525A GB21841/55A GB2184155A GB803525A GB 803525 A GB803525 A GB 803525A GB 21841/55 A GB21841/55 A GB 21841/55A GB 2184155 A GB2184155 A GB 2184155A GB 803525 A GB803525 A GB 803525A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- amino
- give
- ink
- phthalic 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
- 239000000975 dye Substances 0.000 abstract 9
- 239000000976 ink Substances 0.000 abstract 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000005642 Oleic acid Substances 0.000 abstract 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 abstract 3
- 235000019441 ethanol Nutrition 0.000 abstract 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- 239000004375 Dextrin Substances 0.000 abstract 2
- 229920001353 Dextrin Polymers 0.000 abstract 2
- YZBOVSFWWNVKRJ-UHFFFAOYSA-N Monobutylphthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(O)=O YZBOVSFWWNVKRJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 235000019425 dextrin Nutrition 0.000 abstract 2
- 235000011187 glycerol Nutrition 0.000 abstract 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 2
- 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 abstract 2
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 abstract 2
- XIKIUQUXDNHBFR-UHFFFAOYSA-N monobenzyl phthalate Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 XIKIUQUXDNHBFR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 abstract 1
- JTOSHSWKQMEPKA-UHFFFAOYSA-N 1-n,1-n-dimethylpentane-1,4-diamine Chemical compound CC(N)CCCN(C)C JTOSHSWKQMEPKA-UHFFFAOYSA-N 0.000 abstract 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract 1
- 244000215068 Acacia senegal Species 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- 241000416162 Astragalus gummifer Species 0.000 abstract 1
- RISUMPVKPHEEJG-UHFFFAOYSA-N C1=CC=CC=C1[Cu](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1[Cu](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RISUMPVKPHEEJG-UHFFFAOYSA-N 0.000 abstract 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 abstract 1
- 229920000084 Gum arabic Polymers 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 229920001615 Tragacanth Polymers 0.000 abstract 1
- 235000010489 acacia gum Nutrition 0.000 abstract 1
- 239000000205 acacia gum Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004056 anthraquinones Chemical class 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 abstract 1
- 125000005521 carbonamide group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004898 kneading Methods 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000012170 montan wax Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000007519 polyprotic acids Polymers 0.000 abstract 1
- 239000008159 sesame oil Substances 0.000 abstract 1
- 235000011803 sesame oil Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
- 235000010487 tragacanth Nutrition 0.000 abstract 1
- 239000000196 tragacanth Substances 0.000 abstract 1
- 229940116362 tragacanth Drugs 0.000 abstract 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/02—Disposition of insulation
-
- 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
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention comprises salts of (a) azo, anthraquinone, phthalocyanine and dioxazine dyes which contain at least one sulphonamide, carbonamide or aminoalkyl group and are substituted at one or more nitrogen atoms of the amide or aminoalkyl groups by an aliphatic radicle which contains a tertiary nitrogen atom; with (b) inorganic acids, carboxylic acids, organic sulphonic acids or such esters of organic dibasic and polybasic acids as contain at least one free carboxylic group. These salts may be made simply by reacting the acid and the basic dyestuff, e.g. in aqueous suspension, in an organic solvent in which the salt is insoluble, or by mixing or kneading without solvents. The products may be used in printing inks, stamp inks, typewriter inks, and in ballpoint pen pastes. In examples: (1) a dye base prepared from a mixture of copper phthalocyanine di- and tri-sulphochlorides and 1-amino - 3 - dimethylamino - propane according to Example (1) of Specification 784,843 is reacted with (a) phthalic acid mono-octyl ester, (b) oleic acid, (c) phthalic acid monobutyl ester, (d) Gersthofen wax S (a montan wax in which 15 per cent of the fatty acids are esterified with higher alcohols), (e) phthalic acid monobenzyl ester, (f) acetic acid; (2) a dye base prepared from tri- or tetra-chlormethyl copper phthalocyanine and 1-diethylamino-4-amino-n-pentane (Example (7) of Specification 784,843) is reacted with oleic acid; (3) the dye base from tetraphenyl copper phthalocyanine tetrasulphochloride and 1-amino-3-dimethylamino-propane is reacted with phthalic acid mono-octyl ester. In examples of ink compositions, (4) the product of 1(f) above is mixed with glycerine, dextrin, gum arabic and water to give a document ink; (5) the phthalocyanine dyestuff of Example (10) of Specification 784,843 is converted to acetate and this is kneaded with diamond green, kaolin and tragacanth to give a pencil lead; (6) the product of (2) above is mixed with Victoria blue, oleic acid, stearin, castor oil, sesame oil and mineral oil to form a typewriter ribbon ink; (7) the product of 1(b) above is dissolved in castor oil and colophony or an alkyd resin added to give a ball-point pen paste; (8) the acetate, oxalate, or malonate of a mixture of the dye base under (1) above and a basic oxazine dye prepared by condensation of chloranil and naphthylamine, sulphochlorination and reaction with 1 - diethylamino - 4 - amino - n - pentane is mixed with glycerine, dextrin and alcohol or ox gall to give an ink; (9) the dye base prepared from a sulphochloride of 4-p-toluido-N-methyl-anthrapyrimidone and 1 - amino - 3 - dimethylamino-propane is reacted with phthalic acid monobenzyl ester in benzyl alcohol; (10) the azo dye of the formula <FORM:0803525/IV (c)/1> is converted to its sulphochloride, this is reacted with 1 - dimethylamino - 4 - amino - n - pentane and the product is reacted with acetic acid in ethyl alcohol to give an ink for stamp pads.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE803525X | 1954-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB803525A true GB803525A (en) | 1958-10-29 |
Family
ID=6721913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21841/55A Expired GB803525A (en) | 1954-07-29 | 1955-07-28 | Basic dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB803525A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571898A (en) * | 1992-10-19 | 1996-11-05 | Basf Aktiengesellschaft | Basic dyes based on amides of j-acid (1-hydroxy-6-aminonaphthalene-3-sulfonic acid) and amides of j-acid |
| EP1676889A1 (en) * | 2004-12-03 | 2006-07-05 | Toyo Ink Mfg. Co., Ltd. | Colored composition |
| WO2007042753A3 (en) * | 2005-10-13 | 2007-07-12 | Fujifilm Imaging Colorants Ltd | Phthalocyanine inks and their use in ink-jet printing |
-
1955
- 1955-07-28 GB GB21841/55A patent/GB803525A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571898A (en) * | 1992-10-19 | 1996-11-05 | Basf Aktiengesellschaft | Basic dyes based on amides of j-acid (1-hydroxy-6-aminonaphthalene-3-sulfonic acid) and amides of j-acid |
| EP1676889A1 (en) * | 2004-12-03 | 2006-07-05 | Toyo Ink Mfg. Co., Ltd. | Colored composition |
| US7156912B2 (en) | 2004-12-03 | 2007-01-02 | Toyo Ink Mfg. Co., Ltd. | Colored composition |
| WO2007042753A3 (en) * | 2005-10-13 | 2007-07-12 | Fujifilm Imaging Colorants Ltd | Phthalocyanine inks and their use in ink-jet printing |
| GB2444204A (en) * | 2005-10-13 | 2008-05-28 | Fujifilm Imaging Colorants Ltd | Phthalocyanine inks and their use in ink-jet printing |
| GB2444204B (en) * | 2005-10-13 | 2009-01-28 | Fujifilm Imaging Colorants Ltd | Phthalocyanine inks and their use in ink-jet printing |
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