Patent US3897450A successfully refreshed from Google Patents.
US3897450A
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Metal phthalocyanine type pigment
Assignee: Dainichiseika Color and Chemicals Mfg Co Ltd
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Filing: 1970-02-10
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Granted: 1975-07-29
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Expires: 1990-02-10
Abstract
Abstract Method for producing a metal phthalocyanine type pigment which comprises subjecting an O-dinitrile type compound and a metallic substance capable of forming a central nucleus of the phthalocyanine type pigment to condensation reaction at a low temperature in the presence of an alkaline substance selected from the group consisting of hydroxide, oxide, peroxide and carbonate of alkali metal and of alkaline earth metal and a hydrophilic organic solvent having hydroxyl radical. By this method, products having clear color tone, fine crystal state, large coloring power, soft texture and superior resistance to heat can be obtained easily with a high yield without the necessity of after treatment of pigmentation.
Inventors
- 👤 Shojiro Horiguchi
- 👤 Yoshio Abe
- 👤 Tohoru Hosoda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 23:41
CPC Classifications
C; C09; C09B; C09B67/00; C09B67/0025; C09B67/0026; C09B47/00; C09B47/04; C09B47/06; C09B47/067
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
227 words
A METHOD FOR PRODUCING A COPPER PHTHALOCYANINE PIGMENT WHICH COMPRISES SUBJECTING AN O-DINITRILE TYPE COMPOUND HAVING A FORMULA OF A (-C=C(-CN)-C(-CN)=C-)(-(X)N) WHEREIN A IS AN ARYL RADICAL OR PYRIDINYL RADICAL, X IS HYDROGEN OR HALOGEN ATOM, NITRO, AMINO, SULFONIC ACID, CARBOXYLIC ACID, ALKYL, METHOXY OR ETHOXY RADICAL, AND N IS AN INTEGER OF 1-4 WHEN X IS HYDROGEN OR HALOGEN ATOM, AND N IS AN INTEGER OF 1-2 WHEN X IS NITRO, AMINO, SULFONIC ACID, CARBOXYLIC ACID, ALKYL, METHOXY OR ETHOXY RADICAL AND 0.25 MOL OR MORE PER MOLE OF O-DINITRILE TYPE COMPOUND OF A METALLIC SUBSTANCE CAPABLE OF FORMING A CENTRAL NUCLEUS OF THE PHTHALOCYAMINE PIGMENT SELECTED FROM THE GROUP CONSISTING OF COPPER POWDER, CUPROUS OXIDE, CUPRIC OXIDE, CUPROUS CHLORIDE, CUPRIC CHLORIDE, COUPROUS BROMIDE, CUPRIC BROMIDE, COPPER SULFATE, COPPER NITRATE, COPPER PHOSPHIDE, AND COPPER ACETATE, TO CONDENSTATION REACTION AT A TEMPERATURE RANGING FROM 100*C TO ROOM TEMPERATURE IN THE PRESENCE OF 0.1 - 2 MOLS PER MOL OF THE O-DINITRILE TYPE COMPOUND OF AN ALKALINE SUBSTANCE SELECTED FROM THE GROUP CONSISTING OF HYDROXIDE, OXIDE, PEROXIDE, AND CARBONATE OF ALKALI METAL AND OF ALKALINE EARTH METAL AND A HYDROPHILIC ORGANIC SOLVENT HAVING HYDROXY RADICAL SELECTED FROM THE GROUP CONSISTING OF METHANOL, ETHANOL, PROPANOL, ISOPROPANOL, BUTANOL, ISOBUTANOL, SECONDARY BUTANOL, ETHYLENE GLYCOL, PROPYLENE GLYCOL, POLYETHYLENE GLYCOL, METHYL, CELLOSOLVE, ETHYL CELLOSOLVE, DIETHYLENE GLYCOL ETHYL ETHER, PHENOL, O, -M-, AND P-CRESOL.
Claim 2
Independent Claim
227 words
A METHOD FOR PRODUCING A COPPER PHTHALOCYANINE PIGMENT WHICH COMPRISES SUBJECTING AN O-DINITRILE TYPE COMPOUND HAVING A FORMULA OF A (-C=C(-CN)-C(-CN)=C-)(-(X)N) WHEREIN A IS AN ARYL RADICAL OR PYRIDINYL RADICAL, X IS HYDROGEN OR HALOGEN ATOM, NITRO, AMINO, SULFONIC ACID, CARBOXYLIC ACID, ALKYL, METHOXY OR ETHOXY RADICAL, AND N IS AN INTEGER OF 1-4 WHEN X IS HYDROGEN OR HALOGEN ATOM, AND N IS AN INTEGER OF 1-2 WHEN X IS NITRO, AMINO, SULFONIC ACID, CARBOXYLIC ACID, ALKYL, METHOXY OR ETHOXY RADICAL AND 0.25 MOL OR MORE PER MOLE OF O-DINITRILE TYPE COMPOUND OF A METALLIC SUBSTANCE CAPABLE OF FORMING A CENTRAL NUCLEUS OF THE PHTHALOCYAMINE PIGMENT SELECTED FROM THE GROUP CONSISTING OF COPPER POWDER, CUPROUS OXIDE, CUPRIC OXIDE, CUPROUS CHLORIDE, CUPRIC CHLORIDE, COUPROUS BROMIDE, CUPRIC BROMIDE, COPPER SULFATE, COPPER NITRATE, COPPER PHOSPHIDE, AND COPPER ACETATE, TO CONDENSTATION REACTION AT A TEMPERATURE RANGING FROM 100*C TO ROOM TEMPERATURE IN THE PRESENCE OF 0.1 - 2 MOLS PER MOL OF THE O-DINITRILE TYPE COMPOUND OF AN ALKALINE SUBSTANCE SELECTED FROM THE GROUP CONSISTING OF HYDROXIDE, OXIDE, PEROXIDE, AND CARBONATE OF ALKALI METAL AND OF ALKALINE EARTH METAL AND A HYDROPHILIC ORGANIC SOLVENT HAVING HYDROXY RADICAL SELECTED FROM THE GROUP CONSISTING OF METHANOL, ETHANOL, PROPANOL, ISOPROPANOL, BUTANOL, ISOBUTANOL, SECONDARY BUTANOL, ETHYLENE GLYCOL, PROPYLENE GLYCOL, POLYETHYLENE GLYCOL, METHYL, CELLOSOLVE, ETHYL CELLOSOLVE, DIETHYLENE GLYCOL ETHYL ETHER, PHENOL, O, -M-, AND P-CRESOL.
Claim 3
Independent Claim
18 words
A method for producing a copper phthalocyanine pigment which comprises subjecting an odinitrile type compound having formula of
Claim 4
Independent Claim
18 words
A method for producing a copper phthalocyanine pigment which comprises subjecting an odinitrile type compound having formula of
Claim 5
Dependent Claim
63 words
A method of claim 2 wherein the odinitrile type compound is a member selected from the group consisting of phthalodinitrile, 3, 4-dinitrile diphenyl, 1,2-dinitrile naphthalene, 2,3-dinitrile napthalene, 2,3-dinitrile anthracene, 2,3-dinitrile phenanthrene, mono-, di-, tri or tetra-chlorophthalodinitrile, mono-, di-, tri-or tetra-bromophthalodinitrile, mono-, di-, tri- or tetra-iodophthalodinitrile, sulfonic acid-substituted phthalodinitrile, carboxylic acid substituted pthalodinitrile, nitro-substituted phthalodinitrile, amino-substituted phthalodinitrile, alkyl-substituted phthalodinitrile, methoxy phthalodinitrile, and ethoxy phthalodinitrile.
Claim 6
Dependent Claim
51 words
A method of claim 2 wherein the metallic substance capable of forming a central nucleus of the phthalocyanine pigment is a member selected from the group consisting of copper powder, cuprous oxide, cupric oxide, cuprous chloride, cupric chloride, cuprous bromide, cupric bromide, copper sulfate, copper nitrate, copper phosphide, and copper acetate.
Claim 7
Dependent Claim
69 words
A method of claIm 2 wherein the alkaline substance is a member selected from the group consisting of lithium oxide, lithium peroxide, lithium hyroxide, lithium carbonate, sodium oxide, sodium peroxide, sodium hydroxide, sodium carbonate, potassium oxide, potassium peroxide, potassium hyddroxide, potassium carbonate, beryllium oxide, beryllium hydroxide, magnesium oxide, magnesium hydroxide, clacium oxide, calcium peroxide, calcium hydroxide, strontium oxide, strontium peroxide, strontium hydroxide, barium oxide, barium peroxide and barium hydroxide.
Claim 8
Dependent Claim
38 words
The method of claim 2 wherein 0.25 mol or more per mol of o-dinitrile type compound of said metallic substance are employed; and wherein 0.1-2 mols of said alkaline substance per mol of said o-dinitrile compound are employed.
Claim 9
Dependent Claim
51 words
The method of claim 2 which is carried out in the presence of an ammonium salt selected from the group consisting of ammonium chloride, ammonium nitrate, ammonium sulfate, ammonium persulfate, ammonium orthophosphate, ammonium metaphosphate, ammonium pyrophosphate, ammonium carbonate, ammonium bicarbonate, ammonium formate, ammonium acetate, ammonium propionate, ammonium citrate and ammonium oxalate.
Claim 10
Dependent Claim
40 words
The method of claim 7 wherein the reaction is carried out in the presennce of 0.1-2 mols per mole of the o-dinitrile type compound of said alkaline substance; and 0.1-10% by weight of the o-dinitrile compound of said ammonium salt
Claim 11
Dependent Claim
49 words
The method of claim 2 wherein the reaction is carried out in the presence of a solvent mixture of said hydrophilic organic solvent having hydroxyl radical and a hydrophobic aromatic solvent selected from the group consisting of benzene, toluene, xylene, naphthalene, monochlorobenzene, dichlorobenzene, trichlorobenzene, chloronaphthalene, nitrobenzene, chloronitrobenzene and nitrotoluene.
Claim 12
Dependent Claim
28 words
The method of claim 2 which further comprises adding an acid to the reaction mixture, mixing the total mixture with stirring and removing the acid from the mixture.
Claim 13
Dependent Claim
37 words
The method of claim 2 wherein which further comprises adding an acid and a surfactant to the reaction mixture, mixing the total mixture with stirring and removing said hydrophilic organic solvent and acid form the total mixture.
Claim 14
Dependent Claim
28 words
The method of claim 2 which further comprises adding a sulfuric acid to the reaction mixture, mixing the total mixture with stirring and removing the excess sulfuric acid.
Claim 15
Dependent Claim
17 words
The method of claim 2 wherein the reaction is carried out at a temperature of about 70*C.
Claim 16
Dependent Claim
34 words
A method of claim 10 wherein the acid is a member selected from the group consisting of hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, citric acid, and oxalic acid.
Claim 17
Dependent Claim
21 words
A method of claim 10 wherein the metallic substance capable of forming a central nucleus of the phthalocyanine pigment is copper.
Claim 18
Dependent Claim
81 words
A method of claim 11 wherein the surfactant is a member selected from the group consisting of alkyl arylsulfonate, alkyl naphthalenesulfonate, alkyl sulfosuccinate, lignin sulfonate, sulfuric ester of aliphatic alcohol, sulfuric ester of castor oil, rosin soap, fatty acid ester or ether of polyoxyethylene, polyoxyethylene alky ether, sorbitane ester, mono higher fatty acid salt of sorbitane, polyoxyethylene alkylphenol or ether, alkyl amide of fatty acid, alkyl-triethyl ammonium chloride, alkyl pyridinium halide, fatty acid amine salt of alkyl benzimidazole and cyclohexylamine salt.
Claim 19
Dependent Claim
12 words
The method of claim 1 wherein the temperature is about 70* C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-07-28 | 1979-01-27 | 1979-07-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-07-28 | 1983-01-27 | 1983-07-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-07-28 | 1987-01-27 | 1987-07-29 | $7700.00 | Window Closed / Lapsed |