DE1147192B - Dry pigment preparations for coloring plastics - Google Patents
Dry pigment preparations for coloring plasticsInfo
- Publication number
- DE1147192B DE1147192B DEF31651A DEF0031651A DE1147192B DE 1147192 B DE1147192 B DE 1147192B DE F31651 A DEF31651 A DE F31651A DE F0031651 A DEF0031651 A DE F0031651A DE 1147192 B DE1147192 B DE 1147192B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- pigment preparations
- dry pigment
- coloring plastics
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims description 16
- 229920003023 plastic Polymers 0.000 title claims description 10
- 239000004033 plastic Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000004040 coloring Methods 0.000 title claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 238000010410 dusting Methods 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [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 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 2
- LORSVOJSXMHDHF-UHFFFAOYSA-N tris(4-tert-butylphenyl) phosphate Chemical compound C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C=CC(=CC=1)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1 LORSVOJSXMHDHF-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YQHVEGTZGGQQMV-UHFFFAOYSA-N dicyclohexyl hydrogen phosphate Chemical compound C1CCCCC1OP(=O)(O)OC1CCCCC1 YQHVEGTZGGQQMV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
-
- 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
- C09B67/006—Preparation of organic pigments
-
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0092—Dyes in solid form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
Trockene Pigmentzubereitungen zum Färben von Kunststoffen Die zur Färbung von Kunststoffen verwendeten Pigmente sind auf Grund ihrer oft harten Textur in Kunststoffen und Lacken vielfach nur schlecht und ungenügend verteilbar. Die Kunststoffteile zeigen in solchen Fällen bei den üblichen Verarbeitungsmethoden auf der Walze oder im Extruder ungleichmäßige Färbungen, Farbstippen oder Farbschlieren. Beispiele von Pigmenten mit harter Textur sind Phthalocyanine und Anthrachinonpigmente, Chinacridone und einige Azopigmente.Dry pigment preparations for coloring plastics Die zur The pigments used to color plastics are often tough because of their texture in plastics and paints can often only be distributed poorly and inadequately. the Plastic parts show in such cases with the usual processing methods Uneven colors, specks or streaks of color on the roller or in the extruder. Examples of pigments with a hard texture are phthalocyanines and anthraquinone pigments, Quinacridones and some azo pigments.
Es sind verschiedene Methoden bekanntgeworden, die diese Nachteile beheben sollen. So wurde bereits vorgeschlagen, Pigmente durch Anreiben auf Dreiwalzenstühlen mit Weichmachern anzupasten. Auf diese Weise wird eine bessere Feinverteilung erzielt; das damit gefärbte Medium zeigt im allgemeinen eine gleichmäßige stippenfreie Färbung.Various methods have become known that address these disadvantages should fix. It has already been proposed to rub pigments on three-roll mills paste with plasticizers. In this way a better fine distribution is achieved; the medium stained with it generally shows a uniform, speck-free coloration.
Allerdings lassen sich derartige Pasten insbesondere bei Verwendung organischer Pigmente nur mit einem verhältnismäßig niedrigen Pigmentgehalt (üblicherweise etwa 40%) herstellen. Bei maximaler Konzentration an Pigment sind die Pasten im übrigen nicht mehr gießbar, im technischen Betrieb nur unbequem dosierbar und mit trockenen Kunststoffgranulaten und -pulvern schlecht mischbar.However, such pastes can be used in particular organic pigments only with a relatively low pigment content (usually about 40%). At the maximum concentration of pigment, the pastes are im the rest no longer pourable, in technical operation only inconveniently metered and with Dry plastic granulates and powders are difficult to mix.
Wesentlich angenehmer im Gebrauch sind trockene Zubereitungen. So wurde vorgeschlagen, Pigmente mit Harz- und Celluloseestern oder Polymerisaten zu vermischen. Derartige Produkte haben aber nur eine geringe Einsatzbreite. Sie sind meistens nur mit einem oder wenigen Kunstharzen verträglich.Dry preparations are much more pleasant to use. So it was proposed to add pigments with resin and cellulose esters or polymers mix. However, such products have only a limited range of uses. they are mostly only compatible with one or a few synthetic resins.
Es wurde nun gefunden, daß sich Mischungen von Pigmenten mit solchen Phosphorsäureestern, die einen Schmelzpunkt von etwa 50° C oder darüber aufweisen, in vorzüglicher Weise als trockene und mahlbare Zubereitungen zum Färben von Kunststoffen eignen. Diese Zubereitungen sind in verschiedensten Medien, die bei der Herstellung von Kunststoffen in Betracht kommen. gut verteilbar. Wegen ihrer guten Verträglichkeit mit vielen Kunstharzen sind solche Formierungen fast universell einsetzbar. Im Vergleich zu Pigmentpasten ist außerdem ein höherer Pigmentgehalt erreichbar.It has now been found that mixtures of pigments with such Phosphoric acid esters that have a melting point of about 50 ° C or above, excellently as dry and grindable preparations for coloring plastics suitable. These preparations are in various media that are used in the manufacture of plastics come into consideration. easy to distribute. Because of their good tolerance With many synthetic resins, such formations can be used almost universally. In comparison A higher pigment content can also be achieved with pigment pastes.
Als Phosphorsäureester lassen sich unter anderem verwenden Triphenylphosphat bzw. Mono-, Di- oder Tri-p-chlortriphenylphosphat, Tri-(p-tertiär-butylphenyl)-phosphat, Tri-p-kresylphosphat.Triphenyl phosphate, inter alia, can be used as the phosphoric acid ester or mono-, di- or tri-p-chlorotriphenyl phosphate, tri- (p-tert-butylphenyl) phosphate, Tri-p-cresyl phosphate.
Die Zubereitungen werden im allgemeinen derart hergestellt, daß man den Phosphorsäureester in geschmolzenem Zustand zusammen mit dem Pigment in geeigneten Mahl-, Rühr- oder vorzugsweise Knetvorrichtungen innig vermischt oder knetet und anschließend nach Abkühlung gegebenenfalls zu einem feinkörnigen Pulver vermahlt. Diese Zubereitungen können in üblicher Weise zum Färben verschiedenster Kunststoffe, wie Polyvinylchlorid, Polyäthylen, Polypropylen oder Polystyrol, eingesetzt werden.The preparations are generally prepared in such a way that one the phosphoric ester in the molten state together with the pigment in suitable Milling, stirring or, preferably, kneading devices are intimately mixed or kneaded and then, after cooling, optionally ground to a fine-grain powder. These preparations can be used in the usual way for dyeing a wide variety of plastics, such as polyvinyl chloride, polyethylene, polypropylene or polystyrene can be used.
Beispiel 1 50 Gewichtsteile Triphenylphosphat werden geschmolzen und in einen Kneter gegeben. Hierzu gibt man nach und nach bei 60 bis 70° C unter dauerndem Kneten 50 Gewichtsteile lin-para-N,N'-Chinacridon. Nach 4stündigem Verkneten entleert man den Kneter und erhält ein trocken mahlbares Produkt, mit dem sich Polyäthylen gleichmäßig und ohne Farbstippen färben läßt.Example 1 50 parts by weight of triphenyl phosphate are melted and put in a kneader. This is done gradually at 60 to 70 ° C under constant Knead 50 parts by weight of lin-para-N, N'-quinacridone. Emptied after kneading for 4 hours you the kneader and get a dry grindable product with which polyethylene can be colored evenly and without spots of color.
Beispiel 2 100 Gewichtsteile wäßriger Preßkuchen, der 26 Gewichtsteile eines chlorierten Kupferphthalocyanins enthält, werden mit 400 Gewichtsteilen Wasser verdünnt. Zu dieser Dispersion wird eine Lösung von 26 Gewichtsteilen Tri-p-kresylphosphat in Äthanol am Schnellrührer eingerührt. Diese Mischung wird 24 Stunden in einer Kugelmühle gemahlen, dann filtriert und der Rückstand bei 50° C getrocknet und gemahlen. Man erhält ein feinkörniges, nicht staubendes Produkt, mit dem man Celluloseacetat gleichmäßig und stippenfrei färben kann.Example 2 100 parts by weight of aqueous press cake containing 26 parts by weight of a chlorinated copper phthalocyanine are diluted with 400 parts by weight of water. A solution of 26 parts by weight of tri-p-cresyl phosphate in ethanol is stirred into this dispersion on a high-speed stirrer. This mixture is ground in a ball mill for 24 hours, then filtered, and the residue is dried at 50 ° C. and ground. A fine-grained, non-dusting product is obtained with which cellulose acetate can be dyed evenly and without specks.
Beispiel 3 100 Gewichtsteile eines wäßrigen Preßkuchens, der 36 Gewichtsteile eines Kupferphthalocyanins enthält, werden mit 300 Gewichtsteilen Wasser verdünnt. Zu dieser Dispersion wird eine Lösung von 36 Gewichtsteilen Dicyclohexylphosphat in Äthanol am Schnellrührer eingerührt. Diese Mischung wird 24 Stunden in einer Kugelmühle gemahlen, dann filtriert und der Rückstand bei 50° C getrocknet und gemahlen. Man erhält ein farbstarkes, feinkörniges, nicht staubendes Produkt, mit dem man Polyäthylen gleichmäßig und stippenfrei einfärben kann.Example 3 100 parts by weight of an aqueous press cake containing 36 parts by weight of a copper phthalocyanine are diluted with 300 parts by weight of water. A solution of 36 parts by weight is added to this dispersion Dicyclohexyl phosphate stirred into ethanol on a high-speed stirrer. This mixture is used in a 24 hour Ground ball mill, then filtered and the residue dried at 50 ° C and ground. A strongly colored, fine-grained, non-dusting product is obtained with which one Can color polyethylene evenly and without specks.
Beispiel 4 40 Gewichtsteile Ruß werden in 800 Gewichtsteilen Wasser angerührt und am Schnellrührer mit einer Lösung von 60 Gewichtsteilen Tri-(p-tertiärbutylphenyl)-phosphat in 60 Gewichtsteilen Äthanol versetzt. Diese Mischung wird 24 Stunden in einer Kugelmühle gemahlen, dann filtriert und der Rückstand bei 50° C getrocknet und gemahlen. Man erhält ein feinkörniges, nicht staubendes Produkt, mit dem man weichmacherfreies Polyvinylchlorid gleichmäßig und stippenfrei anfärben kann.Example 4 40 parts by weight of carbon black are dissolved in 800 parts by weight of water stirred and on a high-speed stirrer with a solution of 60 parts by weight of tri- (p-tertiary butylphenyl) phosphate added in 60 parts by weight of ethanol. This mixture is in a ball mill for 24 hours ground, then filtered and the residue dried at 50 ° C and ground. Man receives a fine-grained, non-dusting product, with which one can produce plasticizer-free Can stain polyvinyl chloride evenly and without specks.
Beispiel s 100 Gewichtsteile wäßriger Preßkuchen, der 26 Gewichtsteile eines chlorierten Kupferphthalocyanins enthält, werden mit 400 Gewichtsteilen Wasser verdünnt. In diese Dispersion wird eine Lösung von 26 Gewichtsteilen Tri-o-oxydiphenylphosphat in Athanol am Schnellrührer eingerührt. Diese Mischung wird 24 Stunden in einer Kugelmühle gemahlen, dann filtriert und der Rückstand bei 50° C getrocknet und gemahlen; man erhält ein feinkörniges, nicht staubendes Produkt, mit dem man weichgemachtes Polyvinylchlorid in einem klaren grünen Farbton einfärben kann.Example s 100 parts by weight of aqueous press cake, the 26 parts by weight contains a chlorinated copper phthalocyanine, 400 parts by weight of water diluted. A solution of 26 parts by weight of tri-o-oxydiphenyl phosphate is added to this dispersion stirred into ethanol on a high-speed stirrer. This mixture is used in a 24 hour Ball mill ground, then filtered and the residue dried at 50 ° C and ground; a fine-grained, non-dusting product is obtained, with which one is plasticized Can color polyvinyl chloride in a clear green shade.
Claims (1)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31651A DE1147192B (en) | 1960-07-13 | 1960-07-13 | Dry pigment preparations for coloring plastics |
| GB24164/61A GB924584A (en) | 1960-07-13 | 1961-07-04 | Pigment preparations and process for dyeing plastics |
| FR867657A FR1298021A (en) | 1960-07-13 | 1961-07-11 | Preparation of pigments and process for dyeing synthetic materials |
| BE606037A BE606037A (en) | 1960-07-13 | 1961-07-12 | Preparation of pigments and process for dyeing synthetic materials. |
| NL267047A NL267047A (en) | 1960-07-13 | 1961-07-13 | Method for preparing pigment preparations as well as for dyeing plastics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31651A DE1147192B (en) | 1960-07-13 | 1960-07-13 | Dry pigment preparations for coloring plastics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1147192B true DE1147192B (en) | 1963-04-18 |
Family
ID=7094294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31651A Pending DE1147192B (en) | 1960-07-13 | 1960-07-13 | Dry pigment preparations for coloring plastics |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE606037A (en) |
| DE (1) | DE1147192B (en) |
| FR (1) | FR1298021A (en) |
| GB (1) | GB924584A (en) |
| NL (1) | NL267047A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0225948A1 (en) * | 1985-12-09 | 1987-06-24 | CROMPTON & KNOWLES CORPORATION | Dry pigment system |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL180226C (en) * | 1979-06-14 | 1987-01-16 | Wavin Bv | METHOD FOR PREPARING A DYE MIXTURE AND METHOD FOR DYEING THERMOPLASTIC PLASTICS USING THE DYE MIXTURE SO OBTAINED. |
| ES2156195T3 (en) * | 1994-10-14 | 2001-06-16 | Tioxide Group Services Ltd | INORGANIC PARTICLES COVERED WITH AN ALKYL PHOSPHONIC ACID OR AN ESTER OF THE SAME, ITS PREPARATION AND ITS USE. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE568135A (en) * | 1957-05-29 |
-
1960
- 1960-07-13 DE DEF31651A patent/DE1147192B/en active Pending
-
1961
- 1961-07-04 GB GB24164/61A patent/GB924584A/en not_active Expired
- 1961-07-11 FR FR867657A patent/FR1298021A/en not_active Expired
- 1961-07-12 BE BE606037A patent/BE606037A/en unknown
- 1961-07-13 NL NL267047A patent/NL267047A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE568135A (en) * | 1957-05-29 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0225948A1 (en) * | 1985-12-09 | 1987-06-24 | CROMPTON & KNOWLES CORPORATION | Dry pigment system |
Also Published As
| Publication number | Publication date |
|---|---|
| GB924584A (en) | 1963-04-24 |
| NL267047A (en) | 1964-08-10 |
| BE606037A (en) | 1961-11-03 |
| FR1298021A (en) | 1962-07-06 |
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