DE1235855B - Dyeing of polyester materials - Google Patents
Dyeing of polyester materialsInfo
- Publication number
- DE1235855B DE1235855B DEC30608A DEC0030608A DE1235855B DE 1235855 B DE1235855 B DE 1235855B DE C30608 A DEC30608 A DE C30608A DE C0030608 A DEC0030608 A DE C0030608A DE 1235855 B DE1235855 B DE 1235855B
- Authority
- DE
- Germany
- Prior art keywords
- dyeing
- dyes
- dihydroisoindolone
- polyester materials
- printing
- 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
- 238000004043 dyeing Methods 0.000 title claims description 17
- 229920000728 polyester Polymers 0.000 title claims description 10
- 239000000463 material Substances 0.000 title claims description 6
- 239000000975 dye Substances 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 10
- 239000004744 fabric Substances 0.000 claims description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 4
- 230000008719 thickening Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- -1 carbonamido Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims 1
- 235000019438 castor oil Nutrition 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004792 aryl magnesium halides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/50—Iso-indoles; Hydrogenated iso-indoles with oxygen and nitrogen atoms in positions 1 and 3
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Int. Cl.:Int. Cl .:
D 06 ρD 06 ρ
Deutsche Kl.: 8m-1/01 German class: 8m -1/01
β Nummer: 1 235 855β number: 1 235 855
Aktenzeichen: C 30608 IV c/8 mFile number: C 30608 IV c / 8 m
Anmeldetag: 2. August 1963Filing date: August 2, 1963
Auslegetag: 9. März 1967Opened on: March 9, 1967
Gegenstand der Erfindung ist die Verwendung von Farbstoffen der allgemeinen FormelThe invention relates to the use of dyes of the general formula
Aryl — CAryl - C
ortho-Arylenortho-arylene
worin Aryl und Arylen sich von gleichen oder verschiedenen ein- oder mehrkernigen aromatischen Ringsystemen, die noch weitere Substituenten enthalten können, ableiten, zum Färben von Polyestermaterialien, insbesondere solchen auf Basis von Polyterephthalaten.wherein aryl and arylene are identical or different mononuclear or polynuclear aromatic Ring systems, which may contain further substituents, for dyeing polyester materials, especially those based on polyterephthalates.
Die erfindungsgemäß zu verwendenden Farbstoffe können unter anderem durch Einwirkung von Aryl-magnesiumhalogeniden auf /Msoindigo oder seine Derivate hergestellt werden.The dyes to be used according to the invention can, inter alia, by the action of Aryl magnesium halides on / Msoindigo or its derivatives are produced.
Geeignete Ausgangsprodukte, aus denen die erfindungsgemäß zu verwendenden Farbstoffe durch Kondensation mit einem Phosphoroxyhalogenid und/oder Phosphorpentahalogenid, gegebenenfalls in Gegenwart eines Reduktionsmittels, erhältlich sind, sind Dihydroisoindolonderivate der allgemeinen FormelSuitable starting materials from which the dyes to be used according to the invention are carried out Condensation with a phosphorus oxyhalide and / or phosphorus pentahalide, optionally in the presence of a reducing agent, are available, are dihydroisoindolone derivatives of the general formula
NHNH
Färben von PolyestermaterialienDyeing of polyester materials
Anmelder:Applicant:
Cassella Farbwerke Mainkur Aktiengesellschaft,Cassella Farbwerke Mainkur Aktiengesellschaft,
Frankfurt/M.- FechenheimFrankfurt / M.- Fechenheim
Als Erfinder benannt:Named as inventor:
Dr. Hansjörg Vollmann, Frankfurt/M.Dr. Hansjörg Vollmann, Frankfurt / M.
3-(4'-Methoxyphenyl)-dihydroisoindolon-(l),3- (4'-methoxyphenyl) -dihydroisoindolone- (l),
3-(4'-Phenoxyphenyl)-dihydroisoindolon-(l),3- (4'-phenoxyphenyl) -dihydroisoindolone- (l),
3-[Dibenzofuranyl-(3')]-dihydroisoindolon-(l),3- [dibenzofuranyl- (3 ')] -dihydroisoindolone- (l),
3-[Fluorenyl-(7')]-dihydroisoindolon-(l),3- [fluorenyl- (7 ')] -dihydroisoindolone- (l),
3-Phenyl-3-hydroxy-dihydroisoindolon-(l),3-phenyl-3-hydroxy-dihydroisoindolone- (l),
3-(4'-Chlorphenyl)-3-hydroxy-dihydroiso-3- (4'-chlorophenyl) -3-hydroxy-dihydroiso-
indolon-(l),
3-[Diphenylyl-(l')]-3-hydroxy-dihydroiso-indolone- (l),
3- [Diphenylyl- (l ')] - 3-hydroxy-dihydroiso-
indolon-(l),
3-[4"-Chlor-diphenylyl-(l')]-3-hydroxy-indolone- (l),
3- [4 "-chloro-diphenylyl- (l ')] - 3-hydroxy-
dihydroisoindolon-(l),dihydroisoindolone- (l),
3-Phenyl-3-formamido-dihydroisoindolon-(l),
3-(4'-Chlorphenyl)-3-ureido-dihydroiso-3-phenyl-3-formamido-dihydroisoindolone- (l),
3- (4'-chlorophenyl) -3-ureido-dihydroiso-
indolon-(l),
3-Phenyl-3-(carbmethoxy-amido)-dihydroiso-indolone- (l),
3-phenyl-3- (carbmethoxy-amido) -dihydroiso-
indolon-(l),
3-(4'-Chlorphenyl)-3-(carbäthoxy-amido)-indolone- (l),
3- (4'-chlorophenyl) -3- (carbethoxy-amido) -
dihydroisoindolon-(l),
3-Phenyl-3-methoxy-dihydroisoindolon-(l),
3-ci-Naphthyl-3-hydroxy-dihydroisoindolon-(l),dihydroisoindolone- (l),
3-phenyl-3-methoxy-dihydroisoindolone- (l),
3-ci-naphthyl-3-hydroxy-dihydroisoindolone- (l),
worin die Ringe A und B Substituenten und/oder anneliierte carbo- oder heterocyclische Ringe enthalten können, X Wasserstoff, eine Hydroxylgruppe, einen Alkoxy-, Aryloxy-, Carbonamido-, Ureido-, Carbalkoxyamido-, einen primären, sekundären oder tertiären Aminorest oder ein Halogenatom bedeutet, wie insbesonderewherein the rings A and B contain substituents and / or fused carbo- or heterocyclic rings can, X hydrogen, a hydroxyl group, an alkoxy, aryloxy, carbonamido, ureido, Carbalkoxyamido, a primary, secondary or tertiary amino radical or a halogen atom, like in particular
3-Phenyl-dihydroisoindolon-(l), 3-(4'-Chlorphenyl)-dihydroisoindolon-(l), 3-(4'-Bromphenyl)-dihydroisoindolon-(l), 4,5,6,7-Tetrachlor-3-phenyl-dihydroiso-3-phenyl-dihydroisoindolone- (l), 3- (4'-chlorophenyl) -dihydroisoindolone- (l), 3- (4'-bromophenyl) -dihydroisoindolone- (l), 4,5,6,7-tetrachloro-3-phenyl-dihydroiso-
indolon-(l),
4,5,6,7-Tetrachlor-3-(4'-chlorphenyl)-dihydroisoindolon-(l), indolone- (l),
4,5,6,7-tetrachloro-3- (4'-chlorophenyl) -dihydroisoindolone- (l),
indolon-(l).indolone- (l).
Angesichts der hohen Temperaturbeständigkeit der erfindungsgemäß zu verwendenden Farbstoffe eignen sich diese insbesondere auch zum SpinnfärBen von Polyestermaterialien, wobei sie in üblicher Weise der Spinnmasse einverleibt werden.In view of the high temperature resistance of the dyes to be used according to the invention these are particularly suitable for spin-dyeing polyester materials, although they are more commonly used Way to be incorporated into the spinning mass.
Verwendet man die Farbstoffe zum Färben bzw. Bedrucken von Geweben bzw. Fasermaterialien auf Basis von Polyestern, so können alle für derartige Fasermaterialien bekannten Färbe- bzw. Druckverfahren, z. B. das Thermosolverfahren, das Färben mit Carriern, nach dem HT-Färbeverfahren, eine Fixierung durch Dämpfen bei Normal- bzw. überdruck, das Ausziehverfahren usw., angewendet werden. Beim Färben bzw. Drucken nach dem sogenannten Thermofixierverfahren setzt man die Farbstoffe in Form von wäßrigen Suspensionen oderIf the dyes are used for dyeing or printing fabrics or fiber materials Based on polyesters, all dyeing or printing processes known for such fiber materials can be used, z. B. the thermosol process, dyeing with carriers, after the HT dyeing process, a Fixation by steaming at normal or overpressure, the exhaust process, etc., applied will. When dyeing or printing according to the so-called thermosetting process, the dyes are used in the form of aqueous suspensions or
709 518/441709 518/441
Druckpasten ein, denen auch Carrier oder Netzmittel zugesetzt werden können.Printing pastes to which carriers or wetting agents can also be added.
Im allgemeinen werden die Gewebe bedruckt bzw. geklotzt und nach einer Zwischentrocknung in Abwesenheit von Carriern auf Temperaturen zwischen 160 und 22O0C bzw. in Gegenwart von Carriern auf etwas geringere Temperaturen zur Fixierung erhitzt. Die auf diese Weise erhaltenen Färbungen bzw. Drucke zeichnen sich durch hervorragende Brillanz, gute Heißluftfixierechttieit und gute Lichtechtheit bei hoher Farbausbeute aus.In general, the fabric to be printed or padded and, after an intermediate drying in the absence of carriers at temperatures between 160 and 22O 0 C or in the presence of carriers at slightly lower temperatures for fixation. The dyeings or prints obtained in this way are distinguished by excellent brilliance, good hot air fixation properties and good light fastness with a high color yield.
Da die erfindungsgemäß zu verwendenden Farbstoffe auch auf Baumwolle aufziehen, eignen sie sich vorteilhaft auch zum Färben und Bedrucken von Baumwolle- bzw. Zellwolle-Polyester-Mischgeweben.Since the dyes to be used according to the invention are also absorbed on cotton, they are suitable also advantageous for dyeing and printing cotton or viscose-polyester blended fabrics.
Polyäthylenglykolterephthalatgewebe wird mit einer Klotzlösung, die pro Liter 50 g eines 10%igen wäßrigen Teiges des Farbstoffs, der entweder durch Kondensation von 3-Phenyl-dihydroisoindolon-(l) mit Phosphoroxychlorid oder durch Einwirkung von Phenylmagnesiumbromid auf /Msoindigo erhalten wird, und 30 g Alginatverdickung (4%ig) enthält, geklotzt und getrocknet. Anschließend wird 40 Sekünden bei 2100C thermosoliert. Hierauf wird gut gespült, dann in einer Lösung, die 2 g/l Natriumdithionit, 3 ccm/1 Natronlauge (38° Be) und 1 g/l eines nichtionogenen Waschmittels enthält, während 15 Minuten bei 60 bis 700C behandelt. Anschließend wird gut gespült, mit etwa 2 g/l eines nichtionogenen Waschmittels heiß geseift, gespült und getrocknet. Man erhält so bei sehr' guter Farbstoffausbeute leuchtendgelbe Färbungen mit guten Echtheitseigenschaften. Polyethylene glycol terephthalate fabric is treated with a pad solution containing 50 g per liter of a 10% strength aqueous paste of the dye, which is obtained either by condensation of 3-phenyl-dihydroisoindolone- (l) with phosphorus oxychloride or by the action of phenylmagnesium bromide on / Msoindigo, and 30 g Contains alginate thickening (4%), padded and dried. Subsequently, 40 Sekünden is thermosol treatment at 210 0 C. This will be thoroughly rinsed, then in a solution containing 2 g / l sodium dithionite, 3 cc / 1 sodium hydroxide solution (38 ° Be) and 1 g / l of a nonionic detergent, while treated for 15 minutes at 60 to 70 0 C. Then it is rinsed well, soaped with hot soap with about 2 g / l of a non-ionic detergent, rinsed and dried. In this way, with a very good dye yield, bright yellow dyeings with good fastness properties are obtained.
Polyäthylenglykolterephthalatgewebe wird mit einer Druckpaste, die pro Kilogramm 200 g eines 10%igen wäßrigen Teiges des Farbstoffs, der durch Kondensation von 3 - [Fluorenyl - (7')] - dihydroisoindolon-(l) mit Phosphoroxychlorid erhalten wurde, und 600 g Kristallgummiverdickung (1 : 3) enthält, bedruckt und getrocknet. Anschließend wird, wie unter Beispiel 1 beschrieben, weiter behandelt. Man erhält so einen Scharlachdruck von hervorragender Brillanz und mit guten Echtheitseigenschaften bei hoher Farbstoffausbeute. Polyethylene glycol terephthalate fabric is made with a printing paste containing 200 g of one per kilogram 10% aqueous paste of the dye, which is produced by condensation of 3 - [fluorenyl - (7 ')] - dihydroisoindolone- (l) with phosphorus oxychloride, and 600 g crystal rubber thickening (1: 3) contains, printed and dried. Then, as described in Example 1, further treatment. A scarlet print of outstanding brilliance and good fastness properties with a high dye yield is obtained in this way.
das bedruckte Gewebe und dämpft es anschließend Minuten bei 1050C, so erhält man nach der im Beispiel 1 beschriebenen reduktiven Nachbehandlung scharlachrote Drucke von guten Echtheitseigenschaften. the printed fabric and then steams it for minutes at 105 ° C., scarlet-red prints with good fastness properties are obtained after the reductive aftertreatment described in Example 1.
In nachfolgender Tabelle sind weitere Nuancen, wie sie auf Polyester mit Farbstoffen gemäß der Erfindung beim Spinnfarben bzw. beim nachträglichen Färben oder Bedrucken von Fasern oder Geweben erhalten werden, aufgeführt.In the following table are further nuances, as they are on polyester with dyes according to the Invention in spinning dyeing or in the subsequent dyeing or printing of fibers or fabrics are obtained.
Farbstoff, hergestellt durch Kondensation von Phosphoroxychlorid mitDye made by condensation of phosphorus oxychloride with
3-(4'-Chlorphenyl)-dihydroisoindolon-(l) 3- (4'-chlorophenyl) -dihydroisoindolone- (l)
3-(4'-Bromphenyl)-dihydroisoindolon-(l) 3- (4'-bromophenyl) -dihydroisoindolone- (l)
3-[Diphenylyl-(l')]-dihydroisoindolon-(l) : 3- [Diphenylyl- (l ')] - dihydroisoindolone- (l):
3-[4"-Chlor-diphenylyl-(l')]-dihydroisoindolon-(l) 3- [4 "-chloro-diphenylyl- (l ')] - dihydroisoindolone- (l)
3-(4'-Phenoxy-phenyl)-dihydroisoindolon-(l) 3- (4'-phenoxyphenyl) -dihydroisoindolone- (l)
3-[Dibenzofuranyl-(3')]-dihydroisoindolon-(l) 3- [dibenzofuranyl- (3 ')] -dihydroisoindolone- (l)
3-(4'-Dimethylamino-phenyl)-dihydroisoindolon-(l) 3- (4'-Dimethylaminophenyl) -dihydroisoindolone- (l)
Nuance auf Polyesternuance on polyester
GoldgelbGolden yellow
rotstichiges Gelbreddish yellow
Orangeorange
OrangerotOrange red
Orangeorange
RotorangeRed orange
MarineblauNavy blue
Claims (1)
1. Verwendung von Farbstoffen der allgemeinenPatent claims:
1. Use of dyes of general
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30608A DE1235855B (en) | 1963-08-02 | 1963-08-02 | Dyeing of polyester materials |
| DEC30609A DE1289217B (en) | 1963-08-02 | 1963-08-02 | Process for the preparation of isoindolone derivatives |
| CH1008264A CH441315A (en) | 1963-08-02 | 1964-07-31 | Process for the preparation of isoindolone derivatives |
| FR983738A FR1403436A (en) | 1963-08-02 | 1964-07-31 | Iso-indole derivatives and their preparation |
| GB3143464A GB1020305A (en) | 1963-08-02 | 1964-08-04 | New isoindole derivatives and process for their manufacture |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30608A DE1235855B (en) | 1963-08-02 | 1963-08-02 | Dyeing of polyester materials |
| DEC30609A DE1289217B (en) | 1963-08-02 | 1963-08-02 | Process for the preparation of isoindolone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1235855B true DE1235855B (en) | 1967-03-09 |
Family
ID=25969723
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC30608A Pending DE1235855B (en) | 1963-08-02 | 1963-08-02 | Dyeing of polyester materials |
| DEC30609A Pending DE1289217B (en) | 1963-08-02 | 1963-08-02 | Process for the preparation of isoindolone derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC30609A Pending DE1289217B (en) | 1963-08-02 | 1963-08-02 | Process for the preparation of isoindolone derivatives |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH441315A (en) |
| DE (2) | DE1235855B (en) |
| GB (1) | GB1020305A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757053B1 (en) * | 1996-12-12 | 1999-01-22 | Oreal | USE OF DERIVATIVES OF DI-IMINO-ISOINDOLINE OR 3-AMINO-ISOINDOLONE FOR DYING KERATINIC FIBERS AND DYE COMPOSITIONS CONTAINING THEM |
-
1963
- 1963-08-02 DE DEC30608A patent/DE1235855B/en active Pending
- 1963-08-02 DE DEC30609A patent/DE1289217B/en active Pending
-
1964
- 1964-07-31 CH CH1008264A patent/CH441315A/en unknown
- 1964-08-04 GB GB3143464A patent/GB1020305A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH441315A (en) | 1967-08-15 |
| DE1289217B (en) | 1969-02-13 |
| GB1020305A (en) | 1966-02-16 |
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