DE1259833B - Use of naphthazarin for dyeing and printing synthetic textile material - Google Patents
Use of naphthazarin for dyeing and printing synthetic textile materialInfo
- Publication number
- DE1259833B DE1259833B DEB74717A DEB0074717A DE1259833B DE 1259833 B DE1259833 B DE 1259833B DE B74717 A DEB74717 A DE B74717A DE B0074717 A DEB0074717 A DE B0074717A DE 1259833 B DE1259833 B DE 1259833B
- Authority
- DE
- Germany
- Prior art keywords
- naphthazarin
- textile material
- dyeing
- parts
- synthetic textile
- 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
- RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 title claims description 22
- 239000000463 material Substances 0.000 title claims description 11
- 229920002994 synthetic fiber Polymers 0.000 title claims description 10
- 238000004043 dyeing Methods 0.000 title claims description 9
- 239000004758 synthetic textile Substances 0.000 title claims description 9
- 238000010186 staining Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 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 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- -1 polypropylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ALEBYBVYXQTORU-UHFFFAOYSA-N 6-hydrazinyl-6-oxohexanoic acid Chemical compound NNC(=O)CCCCC(O)=O ALEBYBVYXQTORU-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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
- C09B13/00—Oxyketone dyes
- C09B13/02—Oxyketone dyes of the naphthalene series, e.g. naphthazarin
-
- 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
- D06P1/0048—Converting dyes in situ in a non-appropriate form by hydrolysis, saponification, reduction with split-off of a substituent
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/907—Nonionic emulsifiers for dyeing
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES ^VRrSS PATENTAMTFEDERAL REPUBLIC OF GERMANY GERMAN ^ VRrSS PATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
D 06p D 06p
Deutsche Kl.: 8m-1/01 German class: 8m- 1/01
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
1259 833
B 74717 IV c/8 m
18. Dezember 1963
1. Februar 19681259 833
B 74717 IV c / 8 m
18th December 1963
1st February 1968
Das Färben von synthetischem Textilmaterial in echten schwarzen Tönen bereitet meist Schwierigkeiten, da hierfür kaum einheitliche Farbstoffe zur Verfügung stehen. Man ist in der Regel auf Farbstoffmischungen angewiesen, die aber oft den Nachteil des ungleichen Aufziehvermögens der Einzelkomponenten aufweisen und die in vielen Fällen nur unbefriedigende Echtheitseigenschaften haben.The dyeing of synthetic textile material in real black tones usually causes difficulties, since there are hardly any uniform dyes available for this. One is usually on dye mixtures instructed, but this often has the disadvantage of the unequal absorption capacity of the individual components and which in many cases only have unsatisfactory fastness properties.
Es wurde nun gefunden, daß man auf metallfreiem synthetischem Textilmaterial sehr echte graue bis schwarze Färbungen oder Drucke erhält, wenn man als Farbstoff Naphthazarin verwendet.It has now been found that very real gray to black dyeings or prints are obtained if naphthazarin is used as the dye.
Als metallfreie synthetische Textilmaterialien kommen z. B. Fasern, Fäden, Flocken, Gewebe und Gewirke aus metallfreien synthetischen Stoffen, wie Polyamiden, Polyurethanen oder Polyolefinen, in Betracht. Polyamide sind z. B. solche, die durch Polymerisation von e-Caprolactam, co-Aminoundecansäure oder von Hexamethylendiamin mit Adipinsäure erhalten werden oder derartige Polymerisate enthalten. Als Polyurethane seien z. B. aus Glykolen und Diisocyanaten erhältliche Polymerisate genannt, die sich für die Faserherstellung eignen. Das sind z. B. aus 1,6-Hexandiisocyanat und 1,4-Butandiol oder aus Polytetrahydrofuran, 4,4'-Diphenylmethandiisocyanat und Adipinsäurehydrazid erhältliche Polymerisate. Textilmaterialien aus Polyolefinen sind z. B. solche aus Polypropylen. Die Verwendung von synthetischem Textilmaterial aus Polyamiden ist von besonderem technischem Interesse.As metal-free synthetic textile materials come z. B. fibers, threads, flakes, woven and knitted fabrics made of metal-free synthetic materials, such as Polyamides, polyurethanes or polyolefins into consideration. Polyamides are e.g. B. those through Polymerization of e-caprolactam, co-aminoundecanoic acid or are obtained from hexamethylenediamine with adipic acid or contain such polymers. As polyurethanes are z. B. obtainable from glycols and diisocyanates called polymers that are suitable for fiber production. These are z. B. from 1,6-hexane diisocyanate and 1,4-butanediol or from Polytetrahydrofuran, 4,4'-diphenylmethane diisocyanate and adipic acid hydrazide available polymers. Textile materials made from polyolefins are z. B. those made of polypropylene. The use of synthetic Textile material made from polyamides is of particular technical interest.
Auf synthetischem Textilmaterial erhält man nach dem neuen Verfahren Färbungen oder Drucke in grauen bis schwarzen Farbtönen mit guten Echtheiten. Hierbei wird Textilmaterial aus Polypropylen in grauen Tönen angefärbt. Die auf Polyamiden und Polyurethanen erhältlichen Schwarzfärbungen zeichnen sich durch gute Licht-, Reib- und sehr gute Naßechtheitseigenschaften aus.The new process produces dyeings or prints on synthetic textile material gray to black shades with good fastness properties. Textile material made of polypropylene is used in stained gray tones. Draw the black colors available on polyamides and polyurethanes are characterized by good light, rub and very good wet fastness properties.
Man hat das Naphthazarin (5,8-Dihydroxy-l,4-naphthochinon) bereits als sogenannten »Beizenfarbstoff« für vegetabilische Fasern vorgeschlagen. Da der Farbstoff nach den bekannten Verfahren nur auf solche Cellulosefasern aufzieht, die mit Metallsalzen, wie Aluminium- oder Calciumsalzen, gebeizt wurden, konnte nicht erwartet werden, daß man mit Naphthazarin auf synthetischem Textilmaterial ohne Metallbeize so gute und echte Färbungen erhält.Naphthazarine (5,8-dihydroxy-1,4-naphthoquinone) is already used as a so-called "stain dye" suggested for vegetable fibers. Since the dye according to the known method only on such Picks up cellulose fibers that have been stained with metal salts such as aluminum or calcium salts, could not be expected to work with naphthazarin on synthetic textile material without a metal stain so good and real coloring gets.
Das Naphthazarin verwendet man in, z. B. durch Natriumbisulfit, löslich gemachter Form oder vorzugsweise in feinverteilter Form.The naphthazarin is used in, for. B. by sodium bisulfite, solubilized form or preferably in finely divided form.
Das Färben des metallfreien synthetischen Textilmaterials wird im allgemeinen in schwach alkalischen
Verwendung von Naphthazarin zum Färben und
Bedrucken von synthetischem TextilmaterialThe dyeing of the metal-free synthetic textile material is generally in weakly alkaline use of naphthazarin for dyeing and
Printing on synthetic textile material
Anmelder:Applicant:
Badische Anilin- & Soda-Fabrik
t0 Aktiengesellschaft,
6700 LudwigshafenAniline & Soda Factory in Baden
t0 stock corporation,
6700 Ludwigshafen
Als Erfinder benannt:
. Reinhold Krallmann, 6700 LudwigshafenNamed as inventor:
. Reinhold Krallmann, 6700 Ludwigshafen
ao bis stark sauren Bädern vorgenommen, vorzugsweise jedoch in neutralen bis sauren Bädern und vorteilhaft bei Temperaturen von 90 bis 1000C oder unter erhöhtem Druck bei Temperaturen über 100° C. Dem Färbebad können die üblichen Färbereihilfsmittel, z. B. das Umsetzungsprodukt aus 1 Mol Rizinusöl mit 40 Mol Äthylenoxyd, zugesetzt werden.ao to strongly acidic baths made, but preferably in neutral to acidic baths and advantageously at temperatures of 90 to 100 0 C or under increased pressure at temperatures above 100 ° C. The dyebath can use the usual dyeing auxiliaries, eg. B. the reaction product of 1 mole of castor oil with 40 moles of ethylene oxide, are added.
Beispielsweise verwendet man Färbebäder, die auf 1000 Teile 0,1 bis 50 Teile feinverteilten oder löslich
gemachten Farbstoff 0,05 bis 10 Teile eines üblichen Färbereihilf smittels, z. B. das Umsetzungsprodukt aus
1 Mol Spermölalkohol und 80 Mol Äthylenoxyd, 0,5 bis 5 Teile einer Säure, wie Ameisensäure oder Essigsäure,
und 900 bis 995 Teils Wasser enthalten.
Für das Drucken verwendet man z. B. Druckpasten, die in der Regel auf 1000 Teile 1 bis 150 Teile Naphthazarin
in feinverteilter oder löslich gemachter Form, 200 bis 650 Teile der üblichen Verdickungsmittel, ζ. Β.
Kristallgummi, erforderlichenfalls 1 bis 50 Teile der üblichen Druckereihilfsmittel, z. B. Resorcin, und 250
bis 800 Teile Wasser enthalten. Nach dem Bedrucken wird das Gut wie üblich gedämpft oder einer Wärmebehandlung
unterworfen.For example, dyebaths are used which contain 0.1 to 50 parts of finely divided or solubilized dye 0.05 to 10 parts of a conventional dyeing aid, e.g. B. contain the reaction product of 1 mole of sperm oil alcohol and 80 moles of ethylene oxide, 0.5 to 5 parts of an acid such as formic acid or acetic acid, and 900 to 995 parts of water.
For printing one uses z. B. printing pastes, which are usually 1 to 150 parts of naphthazarine in finely divided or solubilized form, 200 to 650 parts of the usual thickeners, ζ. Β. Crystal rubber, if necessary 1 to 50 parts of the usual printing auxiliaries, e.g. B. resorcinol, and 250 to 800 parts of water. After printing, the item is steamed as usual or subjected to a heat treatment.
Die in den Beispielen genannten Teile und Prozente sind Gewichtseinheiten.The parts and percentages given in the examples are weight units.
B e i s ρ i e 1 1B e i s ρ i e 1 1
Ein Gewebe aus Polyhexamethylendiaminadipat bedruckt man mit einer Paste, die aus 70 Teilen feinverteiltem Naphthazarin, 600 Teilen einer Kristallgummiverdickung (1:1) und 330 Teilen Wasser besteht. Das bedruckte Gewebe wird getrocknet und 30 Minuten gedämpft. Der erhaltene schwarze DruckA fabric made of polyhexamethylenediamine adipate is printed with a paste consisting of 70 parts finely divided Naphthazarin, 600 parts of a crystal rubber thickener (1: 1) and 330 parts of water. The printed fabric is dried and steamed for 30 minutes. The black print obtained
709 747/514709 747/514
ist gut lichtecht
eigenschaften.is good lightfast
properties.
und hat ,sehr gute Naßechtheits-Beisp iel 2and has very good wet fastness example 2
100 Teile Polycaprolactamflocken werden in einem Bad aus 3000 Teilen Wasser, 5 Teilen feinverteiltem Naphthazarin, 2,5 Teilen des Umsetzungsproduktes aus 1 Mol Rizinusöl und 40 Teilen Äthylenoxyd und 2 Teilen 30%iger wäßriger Essigsäure 90 Minuten bei 95 bis 100° C gefärbt. Die erhaltene schwarze Färbung ist gut licht- und sehr gut naßecht.100 parts of polycaprolactam flakes are finely divided in a bath of 3000 parts of water and 5 parts Naphthazarin, 2.5 parts of the reaction product of 1 mole of castor oil and 40 parts of ethylene oxide and 2 parts of 30% aqueous acetic acid colored at 95 to 100 ° C. for 90 minutes. The black coloration obtained is good lightfast and very good wetfast.
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB74717A DE1259833B (en) | 1963-12-18 | 1963-12-18 | Use of naphthazarin for dyeing and printing synthetic textile material |
| CH1561864A CH417525A (en) | 1963-12-18 | 1964-12-03 | Process for dyeing or printing textile material made of synthetic polyamides |
| NL6414594A NL6414594A (en) | 1963-12-18 | 1964-12-15 | |
| US418907A US3311444A (en) | 1963-12-18 | 1964-12-16 | Dyeing or printing synthetic polyamide textile material |
| DK617964AA DK112725B (en) | 1963-12-18 | 1964-12-16 | Process for the production of gray or black dyes or printing on synthetic textile material. |
| BE657248D BE657248A (en) | 1963-12-18 | 1964-12-17 | |
| GB51329/64A GB1081438A (en) | 1963-12-18 | 1964-12-17 | Dyeing and printing fully synthetic textile material |
| FR999175A FR1417802A (en) | 1963-12-18 | 1964-12-18 | Process for dyeing and printing synthetic textiles |
| AT1074464A AT250286B (en) | 1963-12-18 | 1964-12-18 | Process for dyeing or printing textile material made of synthetic polyamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB74717A DE1259833B (en) | 1963-12-18 | 1963-12-18 | Use of naphthazarin for dyeing and printing synthetic textile material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1259833B true DE1259833B (en) | 1968-02-01 |
Family
ID=6978365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB74717A Pending DE1259833B (en) | 1963-12-18 | 1963-12-18 | Use of naphthazarin for dyeing and printing synthetic textile material |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3311444A (en) |
| AT (1) | AT250286B (en) |
| BE (1) | BE657248A (en) |
| CH (1) | CH417525A (en) |
| DE (1) | DE1259833B (en) |
| DK (1) | DK112725B (en) |
| FR (1) | FR1417802A (en) |
| GB (1) | GB1081438A (en) |
| NL (1) | NL6414594A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3020259B2 (en) * | 1990-07-11 | 2000-03-15 | イハラケミカル工業株式会社 | Method for producing black coloring material, cosmetic containing black coloring material, and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2365809A (en) * | 1940-06-29 | 1944-12-26 | Celanese Corp | Mordant dyeing of cellulose derivatives |
| CH323364A (en) * | 1953-10-30 | 1957-07-31 | Siemens Ag | A converter made up of a current and voltage converter. |
| GB935125A (en) * | 1962-05-24 | 1963-08-28 | Ici Ltd | Coloured articles of poly-ªá-olefins |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2687939A (en) * | 1954-08-31 | Organic compounds useful as dye |
-
1963
- 1963-12-18 DE DEB74717A patent/DE1259833B/en active Pending
-
1964
- 1964-12-03 CH CH1561864A patent/CH417525A/en unknown
- 1964-12-15 NL NL6414594A patent/NL6414594A/xx unknown
- 1964-12-16 DK DK617964AA patent/DK112725B/en unknown
- 1964-12-16 US US418907A patent/US3311444A/en not_active Expired - Lifetime
- 1964-12-17 BE BE657248D patent/BE657248A/xx unknown
- 1964-12-17 GB GB51329/64A patent/GB1081438A/en not_active Expired
- 1964-12-18 FR FR999175A patent/FR1417802A/en not_active Expired
- 1964-12-18 AT AT1074464A patent/AT250286B/en active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2365809A (en) * | 1940-06-29 | 1944-12-26 | Celanese Corp | Mordant dyeing of cellulose derivatives |
| CH323364A (en) * | 1953-10-30 | 1957-07-31 | Siemens Ag | A converter made up of a current and voltage converter. |
| GB935125A (en) * | 1962-05-24 | 1963-08-28 | Ici Ltd | Coloured articles of poly-ªá-olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1081438A (en) | 1967-08-31 |
| NL6414594A (en) | 1965-06-21 |
| FR1417802A (en) | 1965-11-12 |
| CH417525A (en) | 1967-02-15 |
| DK112725B (en) | 1969-01-13 |
| US3311444A (en) | 1967-03-28 |
| BE657248A (en) | 1965-06-17 |
| CH1561864A4 (en) | 1966-03-31 |
| AT250286B (en) | 1966-11-10 |
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