DE904348C - Process for coloring plastics - Google Patents
Process for coloring plasticsInfo
- Publication number
- DE904348C DE904348C DEC2327D DEC0002327D DE904348C DE 904348 C DE904348 C DE 904348C DE C2327 D DEC2327 D DE C2327D DE C0002327 D DEC0002327 D DE C0002327D DE 904348 C DE904348 C DE 904348C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- soluble
- condensation product
- 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.)
- Expired
Links
Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6497—Amides of di- or polyamines; Acylated polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
- C08L33/20—Homopolymers or copolymers of acrylonitrile
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Patent 889 977 bezieht sidh auf ein Verfahren zum Färben von Kunststoffen, dadurch gekennzeichnet, daß man den Kunststoffen in Wiasser unlösliche bzw. schwer lösliche, aber in organischen Lösungsmitteln lösliche Acylabkömmlinge von Polyalkylenpolyaminen einverleibt und daß man die so animalisierten Kunststoffe dann mit sauren Farbstoffen färbt.Patent 889 977 relates to a process for coloring plastics, characterized in that the plastics are insoluble or sparingly soluble in water, but in organic Solvent-soluble acyl derivatives of polyalkylenepolyamines incorporated and that the animalized plastics in this way are then colored with acidic dyes.
Bei Weiterbearbeitung des Verfahrens wurde nun gefunden, daß es nicht nötigt ist, für das obige Verfahren lediglich in Wasser unlösliche bzw. schwer lösliche Acylabkömmlinge von Polyalkylenpolyaminen zu verwenden, daß man vielmehr mitIn further processing the procedure it has now been found that it is not necessary for the above Process only acyl derivatives of polyalkylenepolyamines which are insoluble or sparingly soluble in water to use that one rather with
gleichem Erfolge auch solche Acylabkömmlinge verwenden kann, die sowohl in organischen Lösungsmitteln als auch in Wasser löslich sind.Such acyl derivatives can also be used with the same success, which are both organic Solvents as well as are soluble in water.
Diese Tatsache ist überraschend, da anzunehmen war, daß die wasserlöslichen Kondensationsprodukte bei der Nachbehandlung der Kunststoffe oder bei dem Färbeprozeß ausgewaschen würden.This fact is surprising since it was to be assumed that the water-soluble condensation products in the aftertreatment of the plastics or washed out in the dyeing process.
Zu 45 Teilen eines Polyäthylenpolyamingemisches, bei dem die bei 10 mm Druck bis 2200 übergehenden Anteile vorher entfernt wurden, läßt man ohne zu kühlen langsam 60 Teile Eseisgsäure-To 45 parts of a polyethylene polyamine mixture, from which the portions passing over at 10 mm pressure to 220 0 have been removed beforehand, 60 parts of icesic acid are slowly added without cooling
arihydrid in dem Maße zufließen, daß die Temperatur 8o° nidht übersteigt. Nach etwa dreistündigem Nachrühren wird die Schmelze im Vakuum allmählich ansteigend bis auf 1500 erhitzt, wobei Essigsäure und überschüssiges Essigsäureanhydrid abdestillieren. Als Rückstand bleiben 80 Teile eines zähen wasserlöslichen Harzes, das sich in organischen Lösungsmitteln (Alkohol, Aceton, Chloroform usw.) löst.arihydride to the extent that the temperature does not exceed 80 °. After about three hours of stirring the melt in the vacuum is gradually heated to 150 increasing to 0, with acetic acid and excess acetic anhydride are distilled off. The residue left is 80 parts of a viscous water-soluble resin that dissolves in organic solvents (alcohol, acetone, chloroform, etc.).
ίο Filme oder Garne aus Polyacrylnitril, denen etwa 5 bis 10% des obigen Kondensationsproduktes zugesetzt sind, lassen sich mit sauren Wollfarbstoffen färben. So ergibt z. B. Supranolbrillantblau G (Schultz, Farbstofftabellen. 7, Aufl., Bd. II, S. 265) aus saurer Flotte im Verhältnis von 2 Teilen auf 100 Teile Färbegut gefärbt, eine starke blaue Färbung.ίο films or yarns made from polyacrylonitrile, which about 5 to 10% of the above condensation product are added, can be acidic Dyeing wool dyes. So z. B. Supranol brilliant blue G (Schultz, color tables. 7, ed., Vol. II, p. 265) dyed from acidic liquor in a ratio of 2 parts to 100 parts of the material to be dyed, a strong blue color.
Filme oder Garne aus Acetatseide, denen 5% des obigen Harzes einverleibt sind, werden beispielsweise durch Walkrot6BA (Schultz, Farbstofftabellen, Bd. II, S. 275), in 3fl/oiger Stänke aus saurer Flotte gefärbt, stark rot gefärbt.Films or yarns made of acetate rayon, which 5% of the above resin are incorporated, are dyed fl example, by Walkrot6BA (Schultz, dye Tables, Vol. II, p 275), in 3 / stank cent of acid liquor, strong red.
45 Teile Polyäthylenpolyamingemisch der oben angegebenen Art werden mit 60 Teilen Bernsteinsäureanhydrid auf 120° erhitzt. Sobald die ziemlich heftige Reaktion abgeklungen ist, erwärmt man die Schmelze noch etwa 2 bis 3 Stunden auf I2O bis 1500 und läßt dann erkalten, wobei ein splitterhartes Harz zurückbleibt, das bei etwa 1140 in eine stark fadenziehende Schmelze übergeht. Das Kondensationsproduikt ist in Wasser und in organischen Lösungsmitteln löslich.45 parts of a polyethylene polyamine mixture of the type indicated above are heated to 120 ° with 60 parts of succinic anhydride. Once the rather violent reaction has subsided, heating the melt for about 2 to 3 hours to I2O to 150 0 and then allowed to cool, whereby a splitter hard resin remains, which passes at about 114 0 in a highly stringy melt. The condensation product is soluble in water and in organic solvents.
Saure Wollfarbstoffe haben zu Filmen oder Fasern aus Polyacrylnitril, denen 6°/o des obigen Kondensationsproduktes einverleibt sind, starke Affinität. So ergibt z. B. Alizarincyaningrün 5 G (Schultz, Farbstofftabellen, Bd. if, S. iii)/in saurer Flotte in 2,5%iger Stärke gefärbt, eine kräftige grüne Färbung.Acid wool dyes have resulted in films or fibers of polyacrylonitrile containing 6% of the above Condensation product are incorporated, strong affinity. So z. B. Alizarin Cyanine Green 5 G (Schultz, color tables, vol. If, p. Iii) / in acid liquor colored in 2.5% strength, a strong green color.
Garne oder Filme aus nachchloriertem Polyvinylchlorid, die io°/o des obigen Kondensationsproduktes enthalten, werden beispielsweise durch Walkgelb A51G (Schultz, Färbstofftabellen, Bd. II, S. 275) kräftig gelb gefärbt,Yarns or films made of post-chlorinated polyvinyl chloride which contain 100% of the above condensation product are, for example, made by Walk yellow A51G (Schultz, Dye Tables, Vol. II, p. 275) colored bright yellow,
Zu einer Lösung von 45 Teilen Polyäthylenpolyamingemisch in etwa 250 Teilen Chloroform läßt man unter Kühlung langsam 45 Teile Äthylisocyanat, gelöst in etwa 100 Teilen Chloroform, zufließen. Nach mehrstündigem Stehen bei 20 bis 300 erwärmt man die Lösung noch 2 Stunden unter Rückfluß und destilliert das Lösungsmittel im Vakuum ab. Es hinterbleibt ein zähes, wasserlösliches Harz, das sich in organischen Lösungsmitteln leicht löst.45 parts of ethyl isocyanate, dissolved in about 100 parts of chloroform, are slowly added to a solution of 45 parts of a polyethylene polyamine mixture in about 250 parts of chloroform, with cooling. After standing for several hours at 20 to 30 0 , the solution is heated under reflux for a further 2 hours and the solvent is distilled off in vacuo. What remains is a tough, water-soluble resin that dissolves easily in organic solvents.
Filme oder Fasern aus Polyacrylnitril oder aus Acetatseide, denen 5 bis iofl/o des obigen Kondensationsproduktes zugesetzt sind, lassen sich mit sauren Wollfarbstoffen färben. So ergibt beispielsweise Walkrot 6BA, in 3%iger Stärke aus saurer Flotte gefärbt, eine kräftige rote Färbung.Films or fibers made of polyacrylonitrile or acetate rayon, which are added to 5 io fl / o of the above condensation product, can be dyed with acid wool dyes. For example, millet red 6BA, dyed in 3% strength from acidic liquor, gives a strong red color.
Zu einer Lösung von 45 Teilen Polyäthylenpolyamingemisch in etwa 250 Teilen Chloroform läßt man langsam unter Kühlen eine Lösung von 85 Teilen Propansulfochlorid zufließen. Nach mehrstündigem Stehen bei 20 bis 300 wird die Lösung in überschüssige io°/oige Natronlauge eingetragen und noch 3 bis 4 Stunden bei etwa 60 bis 8o° gerührt. Nach Erkalten wird das Kondensationsprodukt mit Methylenchlorid ausgeschüttelt und mit Glaubersalz getrocknet. Nach Entfernung des Lösungsmittels hinterbleibt ein zähes Harz, das sich sowohl in Wasser als auch in organischen Lösungsmitteln löst.A solution of 85 parts of propanesulfonyl chloride is slowly added to a solution of 45 parts of a polyethylene polyamine mixture in about 250 parts of chloroform, while cooling. After standing for several hours at 20 to 30 0, the solution in excess io ° / o sodium hydroxide solution is added and stirring continued for 3 to 4 hours at about 60 to 8o °. After cooling, the condensation product is extracted with methylene chloride and dried with Glauber's salt. After the solvent has been removed, a tough resin remains that dissolves both in water and in organic solvents.
Ein Polyacrylmtrilfiim, der 6 bis 10% des obigen Kondensationsproduktes enthält, läßt sich beispielsweise mit Supranolbrillantblau G in saurer Flotte gut färben.A polyacrylic film containing 6 to 10% of the Contains the above condensation product, for example, with Supranol Brilliant Blue G in acidic Color liquor well.
Zu 90 Teilen einer 5o°/oigen Lösung von PoIyäthylenimin in Wasser gibt man 150 Teile Essigsäureanhydrid, wobei nach kurzer Zeit unter Selbsterwärmung eine starke Reaktion eintritt. Man erwärmt hierauf noch im Vakuum auf 90 bis ioo°, bis nichts mehr abdestilliert, und erhält dann eine zähe, stark klebrige, fast farblose Masse, die sich in Wasser und in organischen Lösungsmitteln löst. Ein Polyacrylnitril- oder ein Acetatseidefilm, dem 5 bis 10% des obigen Kondensationsproduktes einverleibt sind, läßt sich mit sauren Wollfarbstoffen kräftig färben.To 90 parts of a 50% solution of polyethylenimine 150 parts of acetic anhydride are added to water, and after a short time under Self-heating a strong reaction occurs. It is then heated to 90 bis in vacuo 100 °, until nothing more distills off, and then receives a tough, very sticky, almost colorless mass that dissolves in water and in organic solvents solves. A polyacrylonitrile or a silk acetate film containing 5 to 10% of the above condensation product are incorporated, can be dyed vigorously with acidic wool dyes.
75 Teile eines Polyalkylenpolyamins, hergestellt (beispielsweise nach Vorschrift der schweizerischen Patentschrift 170 085) durch Kondensation von Ammoniak mit Glycerindichlorhydrin, werden mit 150 Teilen 'Essigsäureanhydrid mehrere Stunden auf dem Wasserbad erwärmt. Im Vakuum wird hierauf bis auf 1400 erhitzt, bis nichts mehr abdestilliert. Es hinterbleibt ein zähes, stark klebriges Harz, das wasserlöslich ist. In Dimethylformamid gelöst, läßt es sich einem Pdlyacrylnitrilfilm einverleiben und bewirkt starke Animalisierung. Ein Film, der 10% des Kondensationsproduktes enthält, wird beispielsweise mit Supranolbrillantblau G stark blau gefärbt.75 parts of a polyalkylenepolyamine, prepared (for example according to the instructions in Swiss patent specification 170 085) by condensation of ammonia with glycerol dichlorohydrin, are heated with 150 parts of acetic anhydride for several hours on a water bath. In the vacuum, then heated to 140 0 to nothing more distilled. What remains is a tough, highly sticky resin that is water-soluble. Dissolved in dimethylformamide, it can be incorporated into a Pdlyacrylonitrilfilm and causes strong animalization. A film which contains 10% of the condensation product is colored strongly blue with Supranol Brilliant Blue G, for example.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEC2327D DE904348C (en) | 1943-11-05 | 1943-12-07 | Process for coloring plastics |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEC2498D DE889977C (en) | 1943-11-05 | 1943-11-05 | Process for coloring plastics that are soluble in organic solvents |
DEC2327D DE904348C (en) | 1943-11-05 | 1943-12-07 | Process for coloring plastics |
Publications (1)
Publication Number | Publication Date |
---|---|
DE904348C true DE904348C (en) | 1954-02-18 |
Family
ID=25969035
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEC2327D Expired DE904348C (en) | 1943-11-05 | 1943-12-07 | Process for coloring plastics |
Country Status (1)
Country | Link |
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DE (1) | DE904348C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3037835A (en) * | 1958-07-02 | 1962-06-05 | Montedison Spa | Processes for improving the dyeability of textile fibers, films, and moulded articles |
-
1943
- 1943-12-07 DE DEC2327D patent/DE904348C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3037835A (en) * | 1958-07-02 | 1962-06-05 | Montedison Spa | Processes for improving the dyeability of textile fibers, films, and moulded articles |
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