USRE35009E - Diketopyrrolopyrrole pigments in platelet form - Google Patents
Diketopyrrolopyrrole pigments in platelet form Download PDFInfo
- Publication number
- USRE35009E USRE35009E US08/145,706 US14570693A USRE35009E US RE35009 E USRE35009 E US RE35009E US 14570693 A US14570693 A US 14570693A US RE35009 E USRE35009 E US RE35009E
- Authority
- US
- United States
- Prior art keywords
- pigments
- pigment
- platelet form
- thickness
- platelet
- 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 - Lifetime
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
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/003—Crystal modifications; Special X-ray patterns of diketopyrrolopyrrole
-
- 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
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
Definitions
- the present invention relates to organic effect pigments in platelet form of specific pigment classes and to the use thereof for producing effect finishes.
- the pearl lustre pigments normally consist of inorganic particles in platelet form which may be coated with coloured oxide layers (q.v. K. Dorfner, E. Merck, "Pearl Lustre Pigments", Speciality Chemicals 2 and 3, February and May 1982). These pigments, however, do not meet present-day colouristic standards in all respects.
- the sole exception so far is an organic pigment in platelet form disclosed as pearl lustre pigment in U.S. Pat. No. 4,370,270.
- This pigment is a copper phthalocyanine of the ⁇ -modification which is synthesised in the form of flakes of at least 10 ⁇ m in length and 3 ⁇ m in width. When incorporated in stoving varnishes, this pigment gives metal effect finishes.
- the present invention relates to organic pigments selected from the diketopyrrolopyrrole, azo, isoindolinone and isoindoline series, which pigments consist of .Iadd.at least .Iaddend.50% by weight of platelets which are from 5 to 50 ⁇ m long, 2 to 50 ⁇ m wide and 0.01 to 5 ⁇ m thick, with the proviso that the ratios of length:thickness and width:thickness must be at least 3, preferably at least 5.
- the pigments preferably consist at least of 70% by weight of platelets of the order of magnitude specified above.
- Preferred pigments in the platelet form of this invention are 1,4-diketopyrrolo-[3,4-c]pyrrole pigments, most preferably 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole.
- the pigments in platelet form of this invention are obtained from the crude pigments or the appropriate pigment forms by recrystallisation in an organic solvent or mixture of solvents, with or without water, in which 0.5 to 10% by weight, preferably 0.1 to 5% by weight, of the pigment is soluble under the conditions of recrystallisation, i.e. normally in the temperature range from 50° C. to the boiling point of the solvent, or also above the boiling point of the solvent, under pressure, in the absence or presence of a solubiliser, for example an organic or, preferably, inorganic base such as aqueous sodium hydroxide, aqueous potassium hydroxide or pyridine, or also an acid such as sulfuric acid.
- a solubiliser for example an organic or, preferably, inorganic base such as aqueous sodium hydroxide, aqueous potassium hydroxide or pyridine, or also an acid such as sulfuric acid.
- suitable solvents are aromatic solvents such as toluene, xylene, o-dichlorobenzene, nitrobenzene and, more particularly, polar solvents such as dimethyl formamide, N-methylpyrrolidone, hexamethylphosphoric triamide, sulfolane, dimethyl sulfoxide and dimethyl sulfone, or mixtures thereof.
- aromatic solvents such as toluene, xylene, o-dichlorobenzene, nitrobenzene
- polar solvents such as dimethyl formamide, N-methylpyrrolidone, hexamethylphosphoric triamide, sulfolane, dimethyl sulfoxide and dimethyl sulfone, or mixtures thereof.
- the pigments which afford the pigments in platelet form by the above described recrystallisation process are those generally known to persons skilled in the art.
- the pigments in platelet form of this invention are preeminently suitable for producing effect finishes, for example pearl lustre or metal lustre finishes, in organic material of high molecular weight and in cosmetic products.
- effect finishes for example pearl lustre or metal lustre finishes
- organic material of high molecular weight and in cosmetic products for example they may be used by themselves or in conjunction with other organic or inorganic, opaque or transparent pigments and/or with other effect pigments. They make it possible to produce novel colouristic and hitherto non-adjustable effect finishes of excellent fastness properties.
- Examples of high molecular weight organic materials which may be coloured or pigmented with the pigments in platelet form of this invention are cellulose ethers and estes such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins such as polymerisation resins or condensation resins, for example aminoplasts, in particular urea/formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, polyesters, ABS, polyphenylene oxides, rubbers, casein, silicone and silicone resins, singly or in admixture.
- cellulose ethers and estes such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate
- natural resins or synthetic resins such as polymerisation resins or condensation resins, for example amino
- the above high molecular weight materials may be singly or as mixtures in the form of plastics, melts or of spinning solutions, paints, coating compositions or printing inks.
- the pigments in platelet form of this invention are preferably used in lacquers, especially in automotive lacquers, in the 1- 2- or 3-layer systems applied at the present time for producing metal effect finishes, for example polyester/melamine or acrylate/melamine basic lacquers which are oversprayed with acrylate/melamine clear lacquers.
- lacquers especially in automotive lacquers
- acrylate/melamine basic lacquers which are oversprayed with acrylate/melamine clear lacquers.
- suitable binders are, typically, alkyd resins (non-baking and baking) as well as 2-K lacquers derived from hydroxyl-containing polyesters or acrylates and isocyanates.
- the bottom-most layer may also contain opaque organic or inorganic pigments.
- the pigments in platelet form of this invention may be used in accordance with the methods described in U.S. Pat. No. 4,539,258.
- the modifiers conventionally employed in all the fields of use referred to above for example plasticisers, waxes and the like, are used.
- lacquers, printing inks, plastics materials and the like are conveniently coloured with the pigments of this invention by cautiously stirring and homogenising the pigments in platelet form in the appropriate media with the aid of dissolvers, impellers or similar apparatus. Intensive dispersion or grinding with balls or other dispersion aggregates must be avoided, as there is otherwise the danger that the platelets will be destroyed by such methods and the colouristic effects lost.
- the pigments in platelet form can be added to the high molecular weight organic material in an amount of 0.01 to 30% by weight, preferably of 0.1 to 10% by weight, based on said material.
- Cosmetic products which can be coloured with the pigments in platelet form of this invention for achieving effect colourations are, for example, eye make-up products such as compact powder, eye-shadow emulsions, mascara products and, in particular, nail varnishes.
- the pigments in platelet form of this invention can be added to the cosmetic product in an amount of 0.5 to 2% by weight, based on said product.
- 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole is recrystallised in 50 ml of N-methylpyrrolidone for 6 hours at 180° C. After 1 hour, the formation of fine platelets can be observed in the suspension. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with N-methylpyrrolidone, ethanol and water, and dried in a vacuum drier.
- a red pigment in platelet form is obtained. At least 50% of the platelets are 5 to 50 ⁇ m long, 2 to 50 ⁇ m wide, and 0.1 to 5 ⁇ m thick.
- 500 g of the pigment obtained according to Example 2 are stirred for 30 minutes with a toothed disc stirrer at 250 rpm into 15 g of a nail varnish comprising 71.7 g of alkyd resin, Alkydal F681®, 21.7 g of sanga oil (petroleum fraction 140°-190° C.), 1.08 g of binder Exkin 2®, 1.08 g of Silicone oil A® (1% in xylene) and 4.36 g of a drying agent solution (6.4 g of Co naphthenate 8%, 37.2 g of Pb naphthenate 24% and 56.4 g of Ca naphthenate 4%).
- the mill base is applied with an automatic coater to Mylar PR Film® (200 ⁇ m wet film thickness). After drying, a red finish with a marked pearlescent effect is obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Organic pigments selected from the diketopyrrolopyrrole, azo, isoindolinone and isoindoline series, which pigments consist of .Iadd.at least .Iaddend.50% by weight of platelets which are from 5 to 50 μm long, 2 to 50 μm wide and 0.01 to 5 μm thick, with the proviso that the ratios of length:thickness and width:thickness must be at least 3.
The pigments in platelet form are excellently suited to producing effect colorations in high molecular weight organic material and in cosmetic products.
Description
The present invention relates to organic effect pigments in platelet form of specific pigment classes and to the use thereof for producing effect finishes.
It is common knowledge in the art of pigments and has often been reported in the relevant literature that the particle size of a pigment must be below a certain limit in order that the pigment may meet the colouristic requirements made of it. The usual particle size is in the range from ca. 0.1 to 1.0 μm (q.v. Ullmanns Encyclopadie der technischen Chemie, Vol. 13, page 742, 3rd edition, 1962). It is, however, also known that the so-called effect or pearl lustre pigments consist of quite large platelet-shaped particles. Formerly, the pearl lustre effect was obtained with natural fish-silver, i.e. with guanin dispersions obtainable from fish scales. At the present time, the pearl lustre pigments normally consist of inorganic particles in platelet form which may be coated with coloured oxide layers (q.v. K. Dorfner, E. Merck, "Pearl Lustre Pigments", Speciality Chemicals 2 and 3, February and May 1982). These pigments, however, do not meet present-day colouristic standards in all respects. The sole exception so far is an organic pigment in platelet form disclosed as pearl lustre pigment in U.S. Pat. No. 4,370,270. This pigment is a copper phthalocyanine of the β-modification which is synthesised in the form of flakes of at least 10 μm in length and 3 μm in width. When incorporated in stoving varnishes, this pigment gives metal effect finishes.
Surprisingly, it has now been found that it is also possible to obtain a platelet-shaped form of compounds of other specific organic pigment classes for producing effect finishes by subjecting them to recrystallisation in solvents in which they are to a certain degree soluble.
Accordingly, the present invention relates to organic pigments selected from the diketopyrrolopyrrole, azo, isoindolinone and isoindoline series, which pigments consist of .Iadd.at least .Iaddend.50% by weight of platelets which are from 5 to 50 μm long, 2 to 50 μm wide and 0.01 to 5 μm thick, with the proviso that the ratios of length:thickness and width:thickness must be at least 3, preferably at least 5.
The pigments preferably consist at least of 70% by weight of platelets of the order of magnitude specified above.
Preferred pigments in the platelet form of this invention are 1,4-diketopyrrolo-[3,4-c]pyrrole pigments, most preferably 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole.
The pigments in platelet form of this invention are obtained from the crude pigments or the appropriate pigment forms by recrystallisation in an organic solvent or mixture of solvents, with or without water, in which 0.5 to 10% by weight, preferably 0.1 to 5% by weight, of the pigment is soluble under the conditions of recrystallisation, i.e. normally in the temperature range from 50° C. to the boiling point of the solvent, or also above the boiling point of the solvent, under pressure, in the absence or presence of a solubiliser, for example an organic or, preferably, inorganic base such as aqueous sodium hydroxide, aqueous potassium hydroxide or pyridine, or also an acid such as sulfuric acid.
Examples of suitable solvents are aromatic solvents such as toluene, xylene, o-dichlorobenzene, nitrobenzene and, more particularly, polar solvents such as dimethyl formamide, N-methylpyrrolidone, hexamethylphosphoric triamide, sulfolane, dimethyl sulfoxide and dimethyl sulfone, or mixtures thereof.
Conveniently 1 to 20% by weight, preferably 3 to 15% by weight, of the pigment, based on the solvent or solvent mixture, is recrystallised for at least 30 minutes, with cautious stirring, in said solvent or solvent mixture. The duration of the recrystallisation will depend on the desired size of the platelets.
The pigments which afford the pigments in platelet form by the above described recrystallisation process are those generally known to persons skilled in the art.
The pigments in platelet form of this invention are preeminently suitable for producing effect finishes, for example pearl lustre or metal lustre finishes, in organic material of high molecular weight and in cosmetic products. For this utility they may be used by themselves or in conjunction with other organic or inorganic, opaque or transparent pigments and/or with other effect pigments. They make it possible to produce novel colouristic and hitherto non-adjustable effect finishes of excellent fastness properties.
Examples of high molecular weight organic materials which may be coloured or pigmented with the pigments in platelet form of this invention are cellulose ethers and estes such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins such as polymerisation resins or condensation resins, for example aminoplasts, in particular urea/formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, polyesters, ABS, polyphenylene oxides, rubbers, casein, silicone and silicone resins, singly or in admixture.
The above high molecular weight materials may be singly or as mixtures in the form of plastics, melts or of spinning solutions, paints, coating compositions or printing inks.
The pigments in platelet form of this invention are preferably used in lacquers, especially in automotive lacquers, in the 1- 2- or 3-layer systems applied at the present time for producing metal effect finishes, for example polyester/melamine or acrylate/melamine basic lacquers which are oversprayed with acrylate/melamine clear lacquers. For this utility it is also possible to use in place of solvent-based basic lacquers those containing water as solvent. Further suitable binders are, typically, alkyd resins (non-baking and baking) as well as 2-K lacquers derived from hydroxyl-containing polyesters or acrylates and isocyanates. For use in 3-layer systems, the bottom-most layer may also contain opaque organic or inorganic pigments. In such systems, the pigments in platelet form of this invention may be used in accordance with the methods described in U.S. Pat. No. 4,539,258. In other respects, the modifiers conventionally employed in all the fields of use referred to above, for example plasticisers, waxes and the like, are used.
The lacquers, printing inks, plastics materials and the like are conveniently coloured with the pigments of this invention by cautiously stirring and homogenising the pigments in platelet form in the appropriate media with the aid of dissolvers, impellers or similar apparatus. Intensive dispersion or grinding with balls or other dispersion aggregates must be avoided, as there is otherwise the danger that the platelets will be destroyed by such methods and the colouristic effects lost.
The pigments in platelet form can be added to the high molecular weight organic material in an amount of 0.01 to 30% by weight, preferably of 0.1 to 10% by weight, based on said material.
Cosmetic products which can be coloured with the pigments in platelet form of this invention for achieving effect colourations are, for example, eye make-up products such as compact powder, eye-shadow emulsions, mascara products and, in particular, nail varnishes. The pigments in platelet form of this invention can be added to the cosmetic product in an amount of 0.5 to 2% by weight, based on said product.
The invention is illustrated by the following Examples.
With cautious stirring, 1 g of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole is recrystallised in 50 ml of N-methylpyrrolidone for 6 hours at 180° C. After 1 hour, the formation of fine platelets can be observed in the suspension. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with N-methylpyrrolidone, ethanol and water, and dried in a vacuum drier.
A red pigment in platelet form is obtained. At least 50% of the platelets are 5 to 50 μm long, 2 to 50 μm wide, and 0.1 to 5 μm thick.
With cautious stirring, 20 g of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole are recrystallised in 600 ml of dimethyl formamide for 4 hours at 150° C. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with dimethyl formamide and water, and dried in a vacuum drier. A red pigment in platelet form is obtained. At least 70% of the platelets are 10 to 30 μm long, 3 to 30 μm wide, and 0.1 to 4 μm thick.
4 g of the azo pigment, C.I. Pigment Yellow 154, are recrystallised in 100 ml of dimethyl formamide for 4 hours at 110° C. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with dimethyl formamide and water, and dried in a vacuum drier. A yellow pigment in platelet form is obtained.
2 g of the azo pigment, C.I. Pigment Yellow 74, are recrystallised in 100 ml of dimethyl formamide for 2 hours at 60° C. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with dimethyl formamide and water, and the filter product is dried in a vacuum drier. A yellow pigment in platelet form is obtained.
With cautious stirring, 2 g of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole is recrystallised in 100 ml of N-methylpyrrolidone for 24 hours at 120° C. Afterwards the suspension is cooled to 50° C. and 150 g of water are added. The suspension is stirred for a few minutes, then cooled and filtered. The filter product is washed with water and dried in a vacuum drier. A red pigment in platelet form is obtained.
2 g of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole is recrystallised in 100 ml of dimethyl formamide for 23 hours at 180° C. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with 50 ml of dimethyl formamide, 50 ml of isopropanol and copiously with water, and dried in a vacuum drier. A red pigment in platelet form is obtained.
6 g of an orange isoindoline pigment of formula ##STR1## (Example 51 of U.S. Pat. No. 4,262,120) are recrystallised in 100 ml of dimethyl formamide for 19 hours at 180° C. in the presence of 0.22 g of a 30% solution of NaOH. An orange pigment in platelet form is obtained.
With cautious stirring, 15 g of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole is recrystallised in 100 ml of dimethyl formamide for 4 hours at 150° C. Afterwards the suspension is cooled to 50° C. and 150 g of water are added. The suspension is stirred for a few minutes, then cooled and filtered. The filter product is washed with water and dried in a vacuum drier. A red pigment in platelet form is obtained.
2 g of an orange isoindoline pigment according to Example 7 are recrystallised in 100 ml of o-dichlorobenzene for 24 hours at 175° C. in the presence of 0.2 g of a 30% solution of NaOH. Afterwards the suspension is cooled and filtered. The filter product is washed in succession with methanol and water, and dried in a vacuum drier. An orange pigment in platelet form is obtained. At least 50% of the platelets are 2 to 20 μm long, 2 to 12 μm wide, and 0.1 to 1 μm thick.
32 g of the pigment obtained according to Example 2 are stirred for 1 hour with a toothed disc stirrer at 200 rpm into a 8.2% solution of 86 g of cellulose acetobutyrate (25% in butyl acetate), 4 g of zirconium octoate, 48 g of Solvesso 150® (aromatic solvent), 70 g of butyl acetate and 52 g of xylene.
Then 96 g of polyester resin Dynapol H700® (60%) and 12 g of melamine resin Maprenal MF650® (55%) are mixed with the above pigment dispersion to form a lacquer, which is applied with a spray gun. After the coating has dried briefly in the air, a clear lacquer based on a heat-curable acrylic lacquer is applied and baked for 30 minutes at 130° C. A red finish with a pronounced metallic effect is obtained.
500 g of the pigment obtained according to Example 2 are stirred for 30 minutes with a toothed disc stirrer at 250 rpm into 15 g of a nail varnish comprising 71.7 g of alkyd resin, Alkydal F681®, 21.7 g of sanga oil (petroleum fraction 140°-190° C.), 1.08 g of binder Exkin 2®, 1.08 g of Silicone oil A® (1% in xylene) and 4.36 g of a drying agent solution (6.4 g of Co naphthenate 8%, 37.2 g of Pb naphthenate 24% and 56.4 g of Ca naphthenate 4%). The mill base is applied with an automatic coater to Mylar PR Film® (200 μm wet film thickness). After drying, a red finish with a marked pearlescent effect is obtained.
200 g of the pigment obtained according to Example 2 are blended with 13.3 g of polyvinyl chloride and 7.3 g of dioctyl phthalate, and the mixture is processed for 5 minutes at 145° C. to a thin film on a roll mill. The colouration so obtained has a marked metallic effect.
Claims (4)
1. A diketopyrrolopyrrole organic pigment, which consists of .Iadd.at least .Iaddend.50% by weight of platelets which are from 5 to 50 μm long, 2 to 50 μm wide and 0.01 to 5 μm thick, with the proviso that the ratios of length:thickness and width:thickness must be at least 3.
2. An organic pigment according to claim 1, wherein the ratios of length:thickness and width:thickness must be at least 5.
3. An organic pigment according to claim 1 which is a 1,4-diketopyrrolo[3,4-c]pyrrole pigment.
4. An organic pigment according to claim 1 which is 1,4-diketo-3,6-diphenylpyrrolo-[3,4-c]pyrrole.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/145,706 USRE35009E (en) | 1989-07-13 | 1993-10-28 | Diketopyrrolopyrrole pigments in platelet form |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH263089 | 1989-07-13 | ||
CH2630/89 | 1989-07-13 | ||
US07/552,626 US5095122A (en) | 1989-07-13 | 1990-07-13 | Diketopyrrolopyrrole pigments in platelet form |
US08/145,706 USRE35009E (en) | 1989-07-13 | 1993-10-28 | Diketopyrrolopyrrole pigments in platelet form |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/552,626 Reissue US5095122A (en) | 1989-07-13 | 1990-07-13 | Diketopyrrolopyrrole pigments in platelet form |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE35009E true USRE35009E (en) | 1995-08-01 |
Family
ID=4238080
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/552,626 Ceased US5095122A (en) | 1989-07-13 | 1990-07-13 | Diketopyrrolopyrrole pigments in platelet form |
US08/145,706 Expired - Lifetime USRE35009E (en) | 1989-07-13 | 1993-10-28 | Diketopyrrolopyrrole pigments in platelet form |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/552,626 Ceased US5095122A (en) | 1989-07-13 | 1990-07-13 | Diketopyrrolopyrrole pigments in platelet form |
Country Status (4)
Country | Link |
---|---|
US (2) | US5095122A (en) |
EP (1) | EP0408498B1 (en) |
JP (1) | JP2842935B2 (en) |
DE (1) | DE59007114D1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5618343A (en) * | 1994-12-27 | 1997-04-08 | Ciba-Geigy Corporation | Pigment compositions for coatings |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2504649B2 (en) * | 1991-11-26 | 1996-06-05 | 東芝シリコーン株式会社 | Colorant and colored silicone rubber composition |
US5347014A (en) * | 1992-12-23 | 1994-09-13 | Ciba-Geigy Corporation | Process for preparing 1,4-diketo-3,6-diphenylpyrrolo-[3,4-C]-pyrrole |
ES2152375T3 (en) * | 1994-09-14 | 2001-02-01 | Ciba Sc Holding Ag | ORGANIC PIGMENTS READY TO MIX. |
DE69526472T2 (en) | 1994-09-14 | 2002-11-28 | Ciba Speciality Chemicals Holding Inc., Basel | Mixable organic pigments |
US5584922A (en) * | 1994-09-14 | 1996-12-17 | Ciba-Geigy Corporation | Stir-in organic pigments |
US5648408A (en) * | 1995-06-07 | 1997-07-15 | Ciba-Geigy Corporation | Organic stir-in pigments |
ATE201710T1 (en) * | 1996-08-22 | 2001-06-15 | Ciba Sc Holding Ag | CRYSTAL MODIFICATION OF A DIKETOPYRROLOPYRROLE PIGMENT |
EP1137390A1 (en) * | 1998-12-08 | 2001-10-04 | Ciba SC Holding AG | Cosmetic preparations containing organic pigments from the class of pyrrolo- 3,4-c]-pyrroles |
US7563835B2 (en) * | 2001-12-28 | 2009-07-21 | Sun Chemical Corporation | Solventless universal colorants |
US20070031353A1 (en) * | 2003-10-17 | 2007-02-08 | Olof Wallquist | Cosmetic formulations comprising diketo diphenyl pyrrolo-pyrrole pigments |
WO2005039515A1 (en) * | 2003-10-17 | 2005-05-06 | Ciba Specialty Chemicals Holding Inc. | Cosmetic formulations comprising diketo diphenyl pyrrolo-pyrrole pigments |
DE102006007621A1 (en) * | 2006-02-18 | 2007-08-23 | Clariant International Limited | Diketopyrrolopyrrole pigments with increased fastnesses and process for their preparation |
Citations (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH142746A (en) * | 1928-04-07 | 1930-10-15 | Ig Farbenindustrie Ag | Process for the preparation of a new anthraquinone derivative. |
US1891891A (en) * | 1931-11-10 | 1932-12-20 | Oscar V D Luft | Granular organic material |
US2176011A (en) * | 1938-09-15 | 1939-10-10 | Dow Chemical Co | Vat dyestuffs in finely divided form |
US2278973A (en) * | 1942-04-07 | Vat dte preparations | ||
US2402167A (en) * | 1942-12-24 | 1946-06-18 | Du Pont | Physical form of organic pigment |
US2441800A (en) * | 1942-10-02 | 1948-05-18 | Purdue Research Foundation | Process of preparing nitro azo compounds |
US2564225A (en) * | 1946-08-07 | 1951-08-14 | Chadeloid Corp | Dyestuff purification |
US2574597A (en) * | 1949-03-03 | 1951-11-13 | Celanese Corp | Spray-dried dyestuff powders comprising lignin sulfonate |
US2611771A (en) * | 1948-04-28 | 1952-09-23 | Gen Aniline & Film Corp | Preparing organic pigments in finely divided form |
US2755195A (en) * | 1952-07-04 | 1956-07-17 | Ciba Ltd | Process for preparing pigment preparations |
US2816114A (en) * | 1953-08-31 | 1957-12-10 | Du Pont | Production of improved organic pigments |
US2849329A (en) * | 1952-12-12 | 1958-08-26 | Hoechst Ag | Process of preparing water-insoluble coloring matters |
US2893994A (en) * | 1956-07-30 | 1959-07-07 | Allied Chem | Process for producing finely divided vat dye pigments |
US2912428A (en) * | 1956-03-07 | 1959-11-10 | Ciba Ltd | Process for the manufacture of azo pigments |
US2930792A (en) * | 1957-07-31 | 1960-03-29 | Allied Chem | Method for conditioning vat dye filter cakes |
US3016384A (en) * | 1956-07-20 | 1962-01-09 | Ciba Ltd | Process for the manufacture of color pigments in finely divided form |
US3071815A (en) * | 1958-09-09 | 1963-01-08 | Allied Chem | Process for producing free flowing oil soluble fusible organic dyestuffs |
US3127412A (en) * | 1959-09-29 | 1964-03-31 | Ciba Ltd | Process for conditioning pigments |
US3137686A (en) * | 1962-04-10 | 1964-06-16 | Hoechst Ag | Water-insoluble benzimidazolone monoazo-dyestuffs |
US3356443A (en) * | 1964-04-01 | 1967-12-05 | American Cyanamid Co | Mixture of naphtholazobenzene and naphtholazotoluene and its production in granular form |
US3681374A (en) * | 1970-08-11 | 1972-08-01 | Asahi Chemical Ind | Synthetic nacreous triazole crystals and method for production thereof |
US3804824A (en) * | 1970-01-26 | 1974-04-16 | Baker Perkins Inc | Process for purifying organic azo pigments by centrifugation of an agglomerate of the pigment and an organic liquid from an aqueous slurry |
US4117066A (en) * | 1974-05-10 | 1978-09-26 | Ciba-Geigy Ag | Novel process for the complete isolation and rapid drying of solids from suspensions |
US4195020A (en) * | 1973-09-21 | 1980-03-25 | Hoechst Aktiengesellschaft | Dichloro-phenyl-azo-acetoacetylamino-benzimidazolone pigments |
US4206114A (en) * | 1977-07-27 | 1980-06-03 | Ciba-Geigy Corporation | Monoazo pigments from diazotized 5-acylaminoanthranilic acid derivatives and acetoacetylaminobenzimidazolones |
US4341701A (en) * | 1979-11-07 | 1982-07-27 | Ciba-Geigy Corporation | Production of pigments |
US4370270A (en) * | 1980-06-25 | 1983-01-25 | Basf Aktiengesellschaft | Novel pigmentary form of β-copper phthalocyanine |
US4451654A (en) * | 1981-03-05 | 1984-05-29 | Basf Aktiengesellschaft | Conditioning of finely divided crude organic pigments |
CA1169053A (en) * | 1981-01-28 | 1984-06-12 | E. I. Du Pont De Nemours And Company | Azo pigments |
US4560747A (en) * | 1979-10-30 | 1985-12-24 | Ciba Geigy Corporation | Process for producing granulates of water-soluble dyes by fluidized bed granulation |
US4801702A (en) * | 1985-11-06 | 1989-01-31 | Ciba-Geigy Corporation | Process for the preparation and conditioning or organic pigments |
US4876333A (en) * | 1985-10-15 | 1989-10-24 | Ciba-Geigy Corporation | β-crystalline modification of diasazo acid dyestuff |
US4916216A (en) * | 1986-05-13 | 1990-04-10 | Wako Pure Chemical Industries, Ltd. | Process for granulating azobisamidine salts using an aqueous binder |
US5084573A (en) * | 1990-07-13 | 1992-01-28 | Ciba-Geigy Corporation | 2,9-dichloroquinacridone in platelet form |
US5374014A (en) * | 1992-01-20 | 1994-12-20 | Aerospatiale Societe Nationale Industrielle | System for control of an aerodynamic surface of an aircraft |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3137886A (en) * | 1963-04-15 | 1964-06-23 | Sanford Res Company | Cap device for ball-type fluid dispenser |
-
1990
- 1990-07-04 DE DE59007114T patent/DE59007114D1/en not_active Expired - Fee Related
- 1990-07-04 EP EP90810501A patent/EP0408498B1/en not_active Expired - Lifetime
- 1990-07-13 US US07/552,626 patent/US5095122A/en not_active Ceased
- 1990-07-13 JP JP2184383A patent/JP2842935B2/en not_active Expired - Fee Related
-
1993
- 1993-10-28 US US08/145,706 patent/USRE35009E/en not_active Expired - Lifetime
Patent Citations (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2278973A (en) * | 1942-04-07 | Vat dte preparations | ||
CH142746A (en) * | 1928-04-07 | 1930-10-15 | Ig Farbenindustrie Ag | Process for the preparation of a new anthraquinone derivative. |
US1891891A (en) * | 1931-11-10 | 1932-12-20 | Oscar V D Luft | Granular organic material |
US2176011A (en) * | 1938-09-15 | 1939-10-10 | Dow Chemical Co | Vat dyestuffs in finely divided form |
US2441800A (en) * | 1942-10-02 | 1948-05-18 | Purdue Research Foundation | Process of preparing nitro azo compounds |
US2402167A (en) * | 1942-12-24 | 1946-06-18 | Du Pont | Physical form of organic pigment |
US2564225A (en) * | 1946-08-07 | 1951-08-14 | Chadeloid Corp | Dyestuff purification |
US2611771A (en) * | 1948-04-28 | 1952-09-23 | Gen Aniline & Film Corp | Preparing organic pigments in finely divided form |
US2574597A (en) * | 1949-03-03 | 1951-11-13 | Celanese Corp | Spray-dried dyestuff powders comprising lignin sulfonate |
US2755195A (en) * | 1952-07-04 | 1956-07-17 | Ciba Ltd | Process for preparing pigment preparations |
US2849329A (en) * | 1952-12-12 | 1958-08-26 | Hoechst Ag | Process of preparing water-insoluble coloring matters |
US2816114A (en) * | 1953-08-31 | 1957-12-10 | Du Pont | Production of improved organic pigments |
US2912428A (en) * | 1956-03-07 | 1959-11-10 | Ciba Ltd | Process for the manufacture of azo pigments |
US3016384A (en) * | 1956-07-20 | 1962-01-09 | Ciba Ltd | Process for the manufacture of color pigments in finely divided form |
US2893994A (en) * | 1956-07-30 | 1959-07-07 | Allied Chem | Process for producing finely divided vat dye pigments |
US2930792A (en) * | 1957-07-31 | 1960-03-29 | Allied Chem | Method for conditioning vat dye filter cakes |
US3071815A (en) * | 1958-09-09 | 1963-01-08 | Allied Chem | Process for producing free flowing oil soluble fusible organic dyestuffs |
US3127412A (en) * | 1959-09-29 | 1964-03-31 | Ciba Ltd | Process for conditioning pigments |
US3137686A (en) * | 1962-04-10 | 1964-06-16 | Hoechst Ag | Water-insoluble benzimidazolone monoazo-dyestuffs |
US3356443A (en) * | 1964-04-01 | 1967-12-05 | American Cyanamid Co | Mixture of naphtholazobenzene and naphtholazotoluene and its production in granular form |
US3804824A (en) * | 1970-01-26 | 1974-04-16 | Baker Perkins Inc | Process for purifying organic azo pigments by centrifugation of an agglomerate of the pigment and an organic liquid from an aqueous slurry |
US3681374A (en) * | 1970-08-11 | 1972-08-01 | Asahi Chemical Ind | Synthetic nacreous triazole crystals and method for production thereof |
US4195020A (en) * | 1973-09-21 | 1980-03-25 | Hoechst Aktiengesellschaft | Dichloro-phenyl-azo-acetoacetylamino-benzimidazolone pigments |
US4117066A (en) * | 1974-05-10 | 1978-09-26 | Ciba-Geigy Ag | Novel process for the complete isolation and rapid drying of solids from suspensions |
US4206114A (en) * | 1977-07-27 | 1980-06-03 | Ciba-Geigy Corporation | Monoazo pigments from diazotized 5-acylaminoanthranilic acid derivatives and acetoacetylaminobenzimidazolones |
US4560747A (en) * | 1979-10-30 | 1985-12-24 | Ciba Geigy Corporation | Process for producing granulates of water-soluble dyes by fluidized bed granulation |
US4341701A (en) * | 1979-11-07 | 1982-07-27 | Ciba-Geigy Corporation | Production of pigments |
US4370270A (en) * | 1980-06-25 | 1983-01-25 | Basf Aktiengesellschaft | Novel pigmentary form of β-copper phthalocyanine |
CA1169053A (en) * | 1981-01-28 | 1984-06-12 | E. I. Du Pont De Nemours And Company | Azo pigments |
US4451654A (en) * | 1981-03-05 | 1984-05-29 | Basf Aktiengesellschaft | Conditioning of finely divided crude organic pigments |
US4876333A (en) * | 1985-10-15 | 1989-10-24 | Ciba-Geigy Corporation | β-crystalline modification of diasazo acid dyestuff |
US4801702A (en) * | 1985-11-06 | 1989-01-31 | Ciba-Geigy Corporation | Process for the preparation and conditioning or organic pigments |
US4916216A (en) * | 1986-05-13 | 1990-04-10 | Wako Pure Chemical Industries, Ltd. | Process for granulating azobisamidine salts using an aqueous binder |
US5084573A (en) * | 1990-07-13 | 1992-01-28 | Ciba-Geigy Corporation | 2,9-dichloroquinacridone in platelet form |
US5374014A (en) * | 1992-01-20 | 1994-12-20 | Aerospatiale Societe Nationale Industrielle | System for control of an aerodynamic surface of an aircraft |
Non-Patent Citations (5)
Title |
---|
K. Dorfner E. Merck, "Pearl Lustre Pigments", Specialty Chemicals 2 & 3, Feb. & May 1982. |
K. Dorfner E. Merck, Pearl Lustre Pigments , Specialty Chemicals 2 & 3, Feb. & May 1982. * |
Patent Abstracts of Japan, Abstract of JP 57 51733, Jul. 1982. * |
Patent Abstracts of Japan, Abstract of JP 57-51733, Jul. 1982. |
Ullmans Encyclopedia der Techn. Chemie 13, p. 742, Third Ed., 1962. * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5618343A (en) * | 1994-12-27 | 1997-04-08 | Ciba-Geigy Corporation | Pigment compositions for coatings |
Also Published As
Publication number | Publication date |
---|---|
JP2842935B2 (en) | 1999-01-06 |
JPH0352966A (en) | 1991-03-07 |
EP0408498A2 (en) | 1991-01-16 |
US5095122A (en) | 1992-03-10 |
EP0408498A3 (en) | 1992-08-19 |
DE59007114D1 (en) | 1994-10-20 |
EP0408498B1 (en) | 1994-09-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
USRE35009E (en) | Diketopyrrolopyrrole pigments in platelet form | |
US5584922A (en) | Stir-in organic pigments | |
US3157659A (en) | Process for preparing 2, 9-dichloro-quinacridone | |
US3074950A (en) | Process for producing a modification of gamma 7,14-dioxo-5,7,12,14-tetrahydroquinolino-(2,3-b) acridine | |
CA2073196A1 (en) | Process for conditioning organic pigments | |
CA2076281A1 (en) | Oxidation process for preparing quinacridone pigments | |
US5236498A (en) | Quinacridone solid solutions having unique styling applications | |
US6436538B1 (en) | Nitrogen doped carbon-coated effect pigments and their manufacture | |
EP0296107A2 (en) | Organic pigments coated with reticulated ethyl cellulose | |
EP0362129B1 (en) | Paint containing molybdenum disulfide | |
US5084573A (en) | 2,9-dichloroquinacridone in platelet form | |
CA1140130A (en) | Isoindoline pigments, production and use thereof | |
DE69526472T2 (en) | Mixable organic pigments | |
EP1487925A1 (en) | Black pigment compositions | |
DE69217295T2 (en) | Modified gamma quinacridone pigment | |
EP0659840B1 (en) | Organic pigments coated with zirconium or titanium phosphate complexes | |
US5095056A (en) | 2,9-dichloroquinacridone-pigmented engineering plastics and coatings | |
EP1658336A1 (en) | Mixed crystals comprising ci pigment red 170 derivatives | |
EP0982376B1 (en) | Nitrogen doped carbon-coated effect pigments and their manufacture | |
US5491235A (en) | Process for the preparation of organic pigments | |
DE69709687T2 (en) | DYE MIXTURES CONTAINING A SALT-FORMING AZOPIGMENT AND A 1,4-DIKETO-3,6-DIARYLPYRROLO (3,4-C) PYRROL | |
US4143058A (en) | Process for production of an azomethine pigment | |
US5243031A (en) | Process for the production of monoazo lake pigment coated with water-insoluble rosin and improved in lipophilic nature and water resistance | |
US4115377A (en) | Rubine mixed strontium-cadmium salts of 3-chloro-4-methyl-6-sulfophenylazo-hydroxynaphthoic acid | |
US3532665A (en) | Sulfurized decacyclene pigment |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
FPAY | Fee payment |
Year of fee payment: 12 |