GB805562A - New phthalocyanine compounds - Google Patents
New phthalocyanine compoundsInfo
- Publication number
- GB805562A GB805562A GB795556A GB795556A GB805562A GB 805562 A GB805562 A GB 805562A GB 795556 A GB795556 A GB 795556A GB 795556 A GB795556 A GB 795556A GB 805562 A GB805562 A GB 805562A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phthalocyanine
- phenylene
- sulphonic acid
- amino
- copper
- 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
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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/082—Azo dyes dyes containing in the molecule at least one azo group and at least one other chromophore group
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/10—Porphines; Azaporphines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises phthalocyanines of the formula <FORM:0805562/IV (c)/1> wherein (Pc) is a phthalocyanine radical, Y is a direct link or a divalent bridging radical, the system (Pc)-Y contains at least one solubilizing group, R is hydrogen, alkyl, aralkyl, or cycloalkyl, X is halogen, A is halogen or -O-B-, where B is a hydrocarbon or substituted hydrocarbon radical, and n is a whole number. They are made by interacting an aminophthalocyanine of the formula (Pc)-(Y-NHR)n with a triazine of the formula <FORM:0805562/IV (c)/2> or, when Y is -SO2- or -CO-, by interacting a phthalocyanine sulphonic or carboxylic acid chloride of the formula (Pc)1-(Y11-Cl)n with an amino-triazine of the formula <FORM:0805562/IV (c)/3> where (Pc)1 is a phthalocyanine radical, Y11 is -SO2- or -CO-, and the system (Pc)1-Y11-contains a solubilizing group. The aminophthalocyanine compounds used as starting materials, wherein Y is phenylene, -CO-phenylene, -SO2- phenylene, -NH- phenylene, -S- phenylene, -O- phenylene, -CH2S- phenylene, -CH2O- phenylene, -CH2- phenylene, -SCH2- phenylene, and SO2CH2- phenylene are obtained by sulphonation of the corresponding products of Specifications 569,200 and 589,118, [both in Group IV], and these aminophthalocyanines as well as those wherein Y is -NRCO- phenylene, -SO2NR- phenylene, -NRSO2- phenylene, and -SO2O- phenylene may be obtained from sulphonated phthalic acid and appropriately substituted phthalic acids as mentioned in the said Specifications by the usual phthalocyanine-forming reactions. Those aminophthalocyanines where Y is CH2 may be obtained by sulphonating the amines of Specifications 717,137 and 724,212; those where Y is -CH2NR- phenylene by reacting a primary or secondary nitroaniline with a chlormethyl phthalocyanine containing SO3H or COOH, and reduction, or by reacting a chlormethyl phthalocyanine with a diaminobenzene sulphonic or carboxylic acid, those which contain the -SO2NR- alkylene linkage by reacting a chlorsulphonyl phthalocyanine with a monoacetyl alkylene diamine, followed by hydrolysis; those which contain the -SO2NR- phenylene -CH2- group by condensing a chlorsulphonyl phthalocyanine with an amino-N-benzylacetamide followed by hydrolysis; those containing a -CH2-NR- alkylene link by reacting a chlormethyl phthalocyanine containing a sulpho or carboxy group with a monoacetyl alkylene diamine and hydrolysing; those wherein amino is directly attached to the phthalocyanine nucleus by sulphonation of the aminophthalocyanines of Specification 529,847, [Group IV]; those containing the -CONR-or -SO2NR- phenylene link by reacting a phthalocyanine carboxylic or sulphonic acid chloride with a diaminobenzene sulphonic or carboxylic acid or with an aminobenzene sulphonic acid or aminobenzoic acid which contains a nitro group and reducing; those containing the -CONR- phenylene -CH2-link by reacting a phthalocyanine carboxylic chloride with an N-(aminobenzyl)-acetamide and hydrolysing. The process of the invention is preferably carried out in aqueous medium in presence of an acid binding agent at a temperature below 30 DEG C. to avoid hydrolysis of the halogen atoms attached to the triazine rings. The dyestuffs are preferably isolated at a pH of 6-8, and the pastes are dried at, e.g., 20-40 DEG C. in presence of buffering agents. The products are blue to green dyes for, e.g., wool, silk, cotton, linen, regenerated cellulose, nylon, superpolyurethanes. In examples, cyanuric chloride, as a suspension in a water-acetone mixture, is condensed with: (1) copper phthalocyanine-N-(41-amino-31-sulphophenyl) -sulphonamide sulphonic acid, prepared from copper phthalocyanine tetrasulphochloride and 2,5-diaminobenzene sulphonic acid; (2) copper phthalocyanine - N - (4 - b - hydroxyethylamino - 3 - sulphophenyl) - sulphonamide - sulphonic acid, prepared similarly; (3) copper phthalocyanine - 4 - N - (31 - amino - 41 - sulphophenyl)-sulphonamide sulphonic acid; (4) copper - (4 - amino) - phthalocyanine sulphonic acid; (5) copper - 4 - p - aminobenzoyl - phthalocyanine-3-sulphonic acid; (6) copper 4-p-aminobenzene sulphonylphthalocyanine; (7) 4-p-aminophenylmercaptophthalocyanine sulphonic acid; (8) nickel phthalocyanine-N-(31\h-amino-41 - sulphophenyl) - sulphonamide - sulphonic acid; (9) copper phthalocyanine - N - [b - [41 - amino - 21 - sulphophenylamino) - ethyl] - sulphonamide-sulphonic acid; (10) copper phthalocyanine - N - b - aminoethylsulphonamide - sulphonic acid; (11) copper phthalocyanine - N - sulphonpiperazide - sulphonic acid. Also in examples, copper phthalocyanine - 4 - N - (31 - amino - 41 - sulphophenyl) - sulphonamide - 4 - sulphonic acid is condensed with cyanuric bromide, 2,4 - dichloro - 6 - methoxy - s - triazine, and 2,4-dichloro-6-phenoxy-8-triazine. Specification 515,637, [Group IV], also is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB795556A GB805562A (en) | 1956-03-14 | 1956-03-14 | New phthalocyanine compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB795556A GB805562A (en) | 1956-03-14 | 1956-03-14 | New phthalocyanine compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB805562A true GB805562A (en) | 1958-12-10 |
Family
ID=9842993
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB795556A Expired GB805562A (en) | 1956-03-14 | 1956-03-14 | New phthalocyanine compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB805562A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3082201A (en) * | 1956-08-17 | 1963-03-19 | Ciba Ltd | New phthalocyanine dyestuffs containing halogenated triazine nuclei |
US3105070A (en) * | 1960-04-12 | 1963-09-24 | Sandoz Ltd | Phthalocyanine dyestuffs containing halo-pyrimidyl groups |
US3133059A (en) * | 1956-03-14 | 1964-05-12 | Ici Ltd | Copper and nickel phthalocyanine dyestuffs having a mono- and di-halosubstituted triazine ring |
DE1205639B (en) * | 1960-04-05 | 1965-11-25 | Ici Ltd | Process for the preparation of water-soluble phthalocyanine dyes |
US3232931A (en) * | 1962-11-28 | 1966-02-01 | Du Pont | Fiber-reactive metal phthalocyanine dyes |
DE1233517B (en) * | 1961-02-16 | 1967-02-02 | Basf Ag | Process for the production of dyes |
US3413074A (en) * | 1967-08-31 | 1968-11-26 | American Cyanamid Co | Union dyeing and printing of polyester/cellulose blends |
US3503953A (en) * | 1967-12-27 | 1970-03-31 | American Cyanamid Co | Fiber reactive dyes containing at least one methylolated,alkoxymethylolated or acyloxymethylolated iminobis propionamide group |
EP0718375A2 (en) * | 1994-12-21 | 1996-06-26 | Mitsui Toatsu Chemicals, Incorporated | Near infrared absorber, preparation process thereof and use thereof |
WO2008110748A2 (en) * | 2007-03-15 | 2008-09-18 | Fujifilm Imaging Colorants Limited | Phthalocyanines and their use in ink-jet printing |
CN104785296A (en) * | 2015-04-17 | 2015-07-22 | 中国石油大学(华东) | Liquid cobalt sulfonated phthalocyanine catalyst for liquefied petroleum gas mercaptan removal |
CN103553983B (en) * | 2013-10-31 | 2017-10-24 | 天津德凯化工股份有限公司 | A kind of novel dye intermediate and the reactive dye as made from the intermediate |
-
1956
- 1956-03-14 GB GB795556A patent/GB805562A/en not_active Expired
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133059A (en) * | 1956-03-14 | 1964-05-12 | Ici Ltd | Copper and nickel phthalocyanine dyestuffs having a mono- and di-halosubstituted triazine ring |
US3082201A (en) * | 1956-08-17 | 1963-03-19 | Ciba Ltd | New phthalocyanine dyestuffs containing halogenated triazine nuclei |
DE1205639B (en) * | 1960-04-05 | 1965-11-25 | Ici Ltd | Process for the preparation of water-soluble phthalocyanine dyes |
US3105070A (en) * | 1960-04-12 | 1963-09-24 | Sandoz Ltd | Phthalocyanine dyestuffs containing halo-pyrimidyl groups |
DE1233517B (en) * | 1961-02-16 | 1967-02-02 | Basf Ag | Process for the production of dyes |
US3232931A (en) * | 1962-11-28 | 1966-02-01 | Du Pont | Fiber-reactive metal phthalocyanine dyes |
US3413074A (en) * | 1967-08-31 | 1968-11-26 | American Cyanamid Co | Union dyeing and printing of polyester/cellulose blends |
US3503953A (en) * | 1967-12-27 | 1970-03-31 | American Cyanamid Co | Fiber reactive dyes containing at least one methylolated,alkoxymethylolated or acyloxymethylolated iminobis propionamide group |
EP0718375A2 (en) * | 1994-12-21 | 1996-06-26 | Mitsui Toatsu Chemicals, Incorporated | Near infrared absorber, preparation process thereof and use thereof |
EP0718375A3 (en) * | 1994-12-21 | 1997-03-05 | Mitsui Toatsu Chemicals | Near infrared absorber, preparation process thereof and use thereof |
US5705101A (en) * | 1994-12-21 | 1998-01-06 | Mitsui Toatsu Chemicals, Inc. | Near infrared absorber, preparation process therefor and use thereof |
WO2008110748A2 (en) * | 2007-03-15 | 2008-09-18 | Fujifilm Imaging Colorants Limited | Phthalocyanines and their use in ink-jet printing |
WO2008110748A3 (en) * | 2007-03-15 | 2009-01-08 | Fujifilm Imaging Colorants Ltd | Phthalocyanines and their use in ink-jet printing |
GB2459797A (en) * | 2007-03-15 | 2009-11-11 | Fujifilm Imaging Colorants Ltd | Phthalocyanines and their use in ink-jet printing |
CN103553983B (en) * | 2013-10-31 | 2017-10-24 | 天津德凯化工股份有限公司 | A kind of novel dye intermediate and the reactive dye as made from the intermediate |
CN104785296A (en) * | 2015-04-17 | 2015-07-22 | 中国石油大学(华东) | Liquid cobalt sulfonated phthalocyanine catalyst for liquefied petroleum gas mercaptan removal |
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