DE1144678B - Dyeing of polyamide, cellulose ester and polyterephthalic acid ester fibers from aqueous suspension - Google Patents
Dyeing of polyamide, cellulose ester and polyterephthalic acid ester fibers from aqueous suspensionInfo
- Publication number
- DE1144678B DE1144678B DES62204A DES0062204A DE1144678B DE 1144678 B DE1144678 B DE 1144678B DE S62204 A DES62204 A DE S62204A DE S0062204 A DES0062204 A DE S0062204A DE 1144678 B DE1144678 B DE 1144678B
- Authority
- DE
- Germany
- Prior art keywords
- blue
- dyeing
- hydroxy
- fibers
- parts
- 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
- 239000000835 fiber Substances 0.000 title claims description 26
- 238000004043 dyeing Methods 0.000 title claims description 20
- 239000004952 Polyamide Substances 0.000 title claims description 7
- 229920002647 polyamide Polymers 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title claims description 6
- 229920002678 cellulose Polymers 0.000 title claims description 5
- 150000002148 esters Chemical class 0.000 title claims description 5
- 239000007900 aqueous suspension Substances 0.000 title claims description 4
- -1 anthraquinone radical Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 6
- 239000001000 anthraquinone dye Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 2
- 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 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 21
- 229920000297 Rayon Polymers 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229920000139 polyethylene terephthalate Polymers 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 238000009998 heat setting Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000002964 rayon Substances 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- WAXMTENYNOYEBU-UHFFFAOYSA-N 1-phenylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C1=CC=CC=C1 WAXMTENYNOYEBU-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 1
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- PDFOKTWXKPUBED-UHFFFAOYSA-N acetic acid;2-methoxyphenol Chemical compound CC(O)=O.COC1=CC=CC=C1O PDFOKTWXKPUBED-UHFFFAOYSA-N 0.000 description 1
- QGOYCIVFRISVCU-UHFFFAOYSA-N acetic acid;3-methylphenol Chemical compound CC(O)=O.CC1=CC=CC(O)=C1 QGOYCIVFRISVCU-UHFFFAOYSA-N 0.000 description 1
- GZZSZTGDQJSEQK-UHFFFAOYSA-N acetic acid;benzene-1,2-diol Chemical compound CC(O)=O.OC1=CC=CC=C1O GZZSZTGDQJSEQK-UHFFFAOYSA-N 0.000 description 1
- CGCDNJQZBOKSRN-UHFFFAOYSA-N acetic acid;benzene-1,3,5-triol Chemical compound CC(O)=O.OC1=CC(O)=CC(O)=C1 CGCDNJQZBOKSRN-UHFFFAOYSA-N 0.000 description 1
- LZKPUVULVAMJGR-UHFFFAOYSA-N acetic acid;benzene-1,4-diol Chemical compound CC(O)=O.OC1=CC=C(O)C=C1 LZKPUVULVAMJGR-UHFFFAOYSA-N 0.000 description 1
- ZUQXNLCTJRBSAC-UHFFFAOYSA-N acetic acid;naphthalen-1-ol Chemical compound CC(O)=O.C1=CC=C2C(O)=CC=CC2=C1 ZUQXNLCTJRBSAC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- 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
-
- 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
- D06P3/34—Material containing ester groups
- D06P3/36—Material containing ester groups 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
S 62204 IVc/8mS 62204 IVc / 8m
BEKANNTMACHUNG DER ANMELDUNG UNDAUSGABE DER AUSLEGESCHRIFT: 7. MÄRZ 1963NOTICE THE REGISTRATION AND ISSUE OF EDITORIAL: MARCH 7, 1963
Es wurde gefunden, daß Anthrachinonfarbstoffe der FormelIt has been found that anthraquinone dyes of the formula
OH O NH2 OH O NH 2
-R-R
NH1 NH 1
OHOH
worin R für einen gegebenenfalls, mit Ausnahme von durch Nitro- oder Aminogruppen oder zur O — X-Gruppe paraständigen Halogenatomen, substituierten Arylrest steht, welcher in dem an den Anthrachinonrest gebundenen Kern mindestens eine — O — X-Gruppe trägt, wobei X ein Wasserstoffatom oder einen gegebenenfalls weitersubstituierten Alkyl-, Cycloalkyl- oder Arylrest bedeutet, allein oder im Gemisch miteinander sich vorzüglich zum Färben von Polyamidfasern, Celluloseesterfasern und Polyterephthalsäureesterfasern aus wäßriger Suspension eignen.where R is optionally, with the exception of by nitro or amino groups or to the O - X group para halogen atoms, substituted aryl radical, which is in the anthraquinone radical bonded core carries at least one - O - X group, where X is a hydrogen atom or a optionally further substituted alkyl, cycloalkyl or aryl radical, alone or in admixture with one another excellent for dyeing polyamide fibers, cellulose ester fibers and polyterephthalic acid ester fibers from aqueous suspension are suitable.
In manchen Fällen weisen Farbstoffgemische ein besseres Ziehvermögen als die einzelnen Komponenten auf.In some cases, dye mixtures have a better draw power than the individual components on.
Die erhaltenen Färbungen auf Acetatkunstseide zeichnen sich durch vorzügliche Lichtechtheit und gute Wasch-, Schweiß- und Rauchgasechtheit aus. Die Färbungen auf Triacetatkunstseide und auf Polyesterfasern besitzen sehr gute Licht-, Thermofixier- und Plissierechtheit sowie gute Wasch- und Schweißechtheit. Der Farbstoff reserviert Wolle, Baumwolle und Viskose gut.The dyeings on acetate artificial silk obtained are distinguished by excellent lightfastness and good quality Wash, sweat and smoke gas fastness. The dyeings on triacetate artificial silk and on polyester fibers have very good fastness to light, heat-setting and pleating as well as good fastness to washing and perspiration. The dye reserves wool, cotton, and viscose well.
Die Färbungen auf Polyamidfasern sind licht-, schweiß- und waschecht.The dyeings on polyamide fibers are light, perspiration and washfast.
In der angegebenen Formel bedeutet R vorzugsweise einen Mono-, Di- oder Trihydroxyphenylrest, einen Monohydroxy-, Monomethoxy- oder Monoäthoxynaphthylrest, einen Mono- oder Dialkoxyarylrest, z. B. einen Mono- oder Dimethoxy- oder -äthoxyphenylrest oder einen Monohydroxymonoalkoxyarylrest, z. B. einen Monohydroxymonomethoxy- oder -monoäthoxyphenylrest. In the formula given, R preferably denotes a mono-, di- or trihydroxyphenyl radical, a Monohydroxy, monomethoxy or monoethoxynaphthyl radical, a mono- or dialkoxyaryl radical, e.g. B. a mono- or dimethoxy or ethoxyphenyl radical or a monohydroxymonoalkoxyaryl radical, e.g. B. a monohydroxymonomethoxy or monoethoxyphenyl radical.
Von den zu verwendenden Anthrachinonfarbstoffen sind diejenigen bekannt, welche der angegebenen
Formel entsprechen, worin R für einen Hydroxyphenyl-, Hydroxynaphthyl-, Methoxyphenyl- oder
Dihydroxyphenylrest steht.
Sie werden dadurch erhalten, daß man z. B.
1. an den in konzentrierter Schwefelsäure gelösten Borsäureester der l,5-Dihydroxy-4,8-diaminoanthrachinon-2,6-disulfonsäure
Phenol anlagert (deutsches Patent 445 269),Of the anthraquinone dyes to be used, those are known which correspond to the formula given, in which R is a hydroxyphenyl, hydroxynaphthyl, methoxyphenyl or dihydroxyphenyl radical.
They are obtained by z. B.
1. phenol is added to the boric acid ester of l, 5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulfonic acid dissolved in concentrated sulfuric acid (German patent 445 269),
Färben von Polyamid-, Celluloseester-Dyeing of polyamide, cellulose ester
und Polyterephthalsäureesterfasernand polyterephthalic acid ester fibers
aus wäßriger Suspensionfrom aqueous suspension
Anmelder:
Sandoz A. G., Basel (Schweiz)Applicant:
Sandoz AG, Basel (Switzerland)
Vertreter: Dr. W. Schalk, Dipl.-Ing. P. Wirth,Representative: Dr. W. Schalk, Dipl.-Ing. P. Wirth,
Dipl.-Ing. G. E. M. DannenbergDipl.-Ing. G. E. M. Dannenberg
und Dr. V. Schmied-Kowarzik, Patentanwälte,and Dr. V. Schmied-Kowarzik, patent attorneys,
Frankfurt/M., Große Eschenheimer Str. 39Frankfurt / M., Große Eschenheimer Str. 39
Beanspruchte Priorität:Claimed priority:
Schweiz vom 19. März 1958 und 9. März 1959
(Nr. 57 206 und Nr. 70 513)Switzerland from March 19, 1958 and March 9, 1959
(No. 57 206 and No. 70 513)
Dr. Paul Bücheier, Reinach (Schweiz),
ist als Erfinder genannt wordenDr. Paul Bücheier, Reinach (Switzerland),
has been named as the inventor
2. das Anlagerungsprodukt in saurer wäßriger Lösung kocht oder in alkalischer Lösung auf 20 bis 60° C erwärmt, wobei eine Sulfonsäuregruppe abgespalten wird (deutsches Patent 446 563), und2. the addition product boils in acidic aqueous solution or in alkaline solution Heated 20 to 60 ° C, with a sulfonic acid group is split off (German Patent 446 563), and
3. aus letzterer die noch vorhandene Sulfonsäuregruppe reduktiv abspaltet (deutsches Patent 456 235).3. reductively splits off the sulfonic acid group that is still present from the latter (German patent 456 235).
In entsprechender Weise können die anderen erfindungsgemäß zu verwendenden Anthrachinonfarbstoffe hergestellt werden.The other anthraquinone dyes to be used according to the invention can be used in a corresponding manner getting produced.
Färbungen mit den vorgeschlagenen Farbstoffen auf Polyterephthalsäureesterfasern sind plissierechter als die mit den nächstvergleichbaren Farbstoffen der deutschen Patentschrift 864 425 und des USA.-Patents 2 773 071 hergestellten Färbungen. Mit den vorgeschlagenen Farbstoffen erhaltene Färbungen auf Polyamidfasern sind thermofixierechter als Färbungen mit den nächstvergleichbaren bekannten Farbstoffen.Dyeings with the proposed dyes on polyterephthalic acid ester fibers are not pleated than those with the closest comparable dyes of the German patent specification 864 425 and the USA patent 2,773,071 dyeings produced. Colorations obtained with the proposed dyes Polyamide fibers are more heat-set than dyeings with the closest comparable known dyes.
Man bereitet ein Färbebad aus 1 Teil des mit HiHe von Türkischrotöl dispergierten Farbstoffes 1,5-Dihydroxy - 4,8 - diamino - 2 - (4' - hydroxy) - phenylanthrachinon, 6 Teilen eines Fettalkoholsulfonates undA dye bath is prepared from 1 part of the dye 1,5-dihydroxy dispersed with HiHe from Turkish red oil - 4,8 - diamino - 2 - (4 '- hydroxy) - phenylanthraquinone, 6 parts of a fatty alcohol sulfonate and
309'538/530309,538 / 530
3000 Teilen Wasser zu. Man geht bei Zimmertemperatur mit 100 Teilen Triacetkunstseide in das Bad ein, erwärmt dieses innerhalb von einer Stunde auf 100° C und hält es während einer Stunde bei 100° C. Nach dieser Zeit ist der Färbeprozeß beendigt. Man nimmt das Färbegut aus dem Bad heraus, spült es und trocknet es. Man erhält eine blaue Färbung von guter Wasch- und Rauchgas-, Thermofixier- und Plissierechtheit und von sehr guter Lichtechtheit. Der Farbstoff reserviert die Wolle gut. Zur Verbesserung der Dispersion kann der Farbstoff Vorgängig des Färbeprozesses mit geeigneten Netzmitteln, Dispergiermitteln oder Emulgatoren vermählen wreden. Er kann auch als wäßrige Paste innig mit einem Dispergiermittel vermischt und durch Trocknung in ein Farbstoffpulver übergeführt werden.3000 parts of water. One enters the bath at room temperature with 100 parts of triacet silk, heats this up to 100 ° C within one hour and keeps it at 100 ° C for one hour this time the dyeing process is finished. The dyed material is taken out of the bath, rinsed and dried it. A blue dyeing of good fastness to washing, flue gas, heat setting and pleating is obtained and very good lightfastness. The dye reserves the wool well. To improve dispersion The dye can be used prior to the dyeing process with suitable wetting agents, dispersants or Wreden wreden emulsifiers. It can also be intimately mixed with a dispersant as an aqueous paste and converted into a dye powder by drying.
1 Teil l,5-Dihydroxy-4,8-diamino-2-(4'-methoxy)-phenylanthrachinon, 1 Teil Natriumsalz der Dinaph- ao thyhnethandisulfonsäure und 8 Teile Wasser werden bis zur Erreichung einer feinen Dispersion vermählen. Man gießt dieses Gemisch in ein aus 3000 Teilen Wasser und 6 Teilen Marseülaner Seife bestehendes Färbebad. Nach Einführen von 100 Teilen eines Gewebes aus Acetatkunstseide wird das Färbebad in einer halben Stunde auf 80° C erwärmt und während einer Stunde bei dieser Temperatur gehalten. Hierauf wird das Gewebe aus der Flotte herausgenommen, mit Wasser gespült und getrocknet. Man erhält eine klare blaue Färbung von ausgezeichneter Lichtechtheit und guter Wasch-, Schweiß- und Rauchgasechtheit.1 part l, 5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone, 1 part of sodium salt of Dinaph- ao thyhnethandisulfonsäure and 8 parts of water grind until a fine dispersion is achieved. This mixture is poured into one of 3000 parts Dye bath consisting of water and 6 parts of Marseilles soap. After introducing 100 parts of a Acetate rayon fabric is heated to 80 ° C in half an hour and during kept at this temperature for one hour. The fabric is then taken out of the liquor, rinsed with water and dried. A clear blue dyeing of excellent lightfastness is obtained and good fastness to washing, sweat and smoke gas.
3535
100 Teile Polyäthylenterephthalatfaser werden bei 60° C in ein Färbebad gebracht, welches aus 3000 Teilen Wasser, 2 Teilen des im Beispiel 1 verwendeten Farbstoffes und l,5Teilen 2-Hydroxy-l,l'-diphenyl besteht. Das Färbebad wird innerhalb von 20 Minuten auf Kochtemperatur erhitzt. Das Färbegut wird während 60 Minuten bei 100° C gefärbt, aus dem Färbebad herausgenommen, mit Wasser gespült und getrocknet. Die Polyesterfaser ist in einem schönen blauen, waschechten und sehr licht-, thermofixier- und plissierechten Ton gefärbt. Mitbehandelte Baumwolle wird gut reserviert.100 parts of polyethylene terephthalate fibers are placed in a dyebath at 60 ° C., which consists of 3,000 parts Water, 2 parts of the dye used in Example 1 and 1.5 parts of 2-hydroxy-l, l'-diphenyl consists. The dyebath is heated to boiling temperature within 20 minutes. The dyed material is Dyed for 60 minutes at 100 ° C, removed from the dyebath, rinsed with water and dried. The polyester fiber is in a beautiful blue, washable and very light, heat-setting colored and pleated clay. Treated cotton is well reserved.
Man bereitet eine feine Farbstoffdispersion aus 1 Teil 1,5 - Dihydroxy - 4,8 - diamino - 2 - (4'-äthoxy>phenylanthrachinon, 1 Teil Sulfitcellulose-Ablaugepulver und 8 Teilen Wasser. Man gießt diese Paste in eine aus 3000 Teilen Wasser und 3 Teilen eines Dispergiermittels bestehende Färbeflotte, die sich in einem Hochtemperaturfärbeapparat befindet, fügt 100 Teile Polyäthylenterephthalatfaser hinzu, verschließt den Färbeapparate und erhitzt ihn, bis die Innentemperatur 102° C beträgt. Nach einer Stunde bei 120°C ist die Färbung beendet. Man nimmt das gefärbte Gut aus dem Apparat heraus, spült es und trocknet es. Die erhaltene blaue Färbung ist gut wasch- und schweißecht sowie sehr gut licht-, thermofixier- und plissierecht. Führt man die Färbung in Gegenwart von Wolle aus, so bleibt letztere ungefärbt.A fine dye dispersion is prepared from 1 part 1,5 - dihydroxy - 4,8 - diamino - 2 - (4'-ethoxy> phenylanthraquinone, 1 part sulphite cellulose liquor powder and 8 parts water. This paste is poured into one of 3,000 parts of water and 3 parts of one Dispersing agent existing dye liquor, which is located in a high-temperature dyeing machine, adds 100 parts of polyethylene terephthalate fiber added, closes the dyeing machine and heated it until the Internal temperature is 102 ° C. After one hour at 120 ° C., the dyeing has ended. You take that dyed goods out of the apparatus, rinses it and dries it. The blue color obtained is good wash- and sweat-proof as well as very good light, heat-setting and pleating fast. If you carry out the staining in Presence of wool, the latter remains undyed.
1 Teil l,5-Dihydroxy-4,8-diamino-2-(4'-methoxy)-phenylanthrachinon, 1 Teil Natriumsalz der DinaphthyhnethandisuÜOnsäure und 8 Teile Wasser werden gemahlen, bis eine feine Dispersion erreicht ist. Dieses Gemisch gießt man in ein Färbebad, das aus 4000 Teilen Wasser und 4 Teilen eines hochsulf onierten Ricinusöls besteht. In dieses Bad führt man 100 Teile Polyamidgewebe ein und steigert die Temperatur im Laufe von 45 Minuten auf 100° C. Man färbt während einer Stunde bei 95 bis 100° C. Hierauf wird das Gewebe wann und kalt gespült und getrocknet. Man erhält eine klare blaue Färbung von sehr guter Wasch- und Schweißechtheit sowie guter Lichtechtheit.1 part l, 5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone, 1 part of the sodium salt of DinaphthyhnethandisuÜOnsäure and 8 parts of water ground until a fine dispersion is achieved. This mixture is poured into a dyebath that is made from 4000 parts of water and 4 parts of a highly sulfonated castor oil. One leads into this bathroom 100 parts of polyamide fabric and the temperature is increased to 100 ° C. in the course of 45 minutes dyes for one hour at 95 to 100 ° C. The fabric is then rinsed cold and cold and then dried. A clear blue dyeing of very good wash and perspiration fastness and good fastness is obtained Lightfastness.
Die folgende Tabelle enthält weitere Farbstoffe der angegebenen Formel, welche sich zum Färben von Acetatkunstseide, Triacetatkunstseide und Polyesterfasern sehr gut eignen. In der Tabelle sind sie durch den dem Rest R zugrunde liegenden Kohlenwasserstoff RH, das zu färbende Material und den Farbton der Färbung gekennzeichnet.The following table contains other dyes of the formula given which are used for dyeing of acetate rayon, triacetate rayon and polyester fibers are very suitable. They are in the table by the hydrocarbon RH on which the radical R is based, the material to be colored and the Hue of the coloring marked.
spielat
game
spielat
game
100 Teile Polyäthylenterephthalatfaser werden bei 600C in ein Färbebad gebracht, welches aus 3000 Teilen Wasser, 1 Teil des im Beispiel 1 verwendeten Farbstoffs, 1 Teil des im Beispiel 2 verwendeten as Farbstoffs und 1,5 Teilen 2-Hydroxy-l,l'-diphenyl besteht. Das Färbebad wird innerhalb von 20 Minuten auf Kochtemperatur erhitzt. Das Färbegut wird während 60 Minuten bei 1000C gefärbt, aus dem Färbebad herausgenommen, mit Wasser gespült und getrocknet. Die Polyesterfaser ist in einem schönen blauen, waschechten und sehr licht-, thermofixier- und plissierechten Ton gefärbt. Mitbehandelte Wolle und Baumwolle werden gut reserviert.100 parts Polyäthylenterephthalatfaser be brought at 60 0 C in a dye bath consisting of 3000 parts of water, 1 part of the dye used in Example 1, 1 part of the dye as used in Example 2 and 1.5 parts of 2-hydroxy-l, l ' -diphenyl. The dyebath is heated to boiling temperature within 20 minutes. The material to be dyed is dyed at 100 ° C. for 60 minutes, taken out of the dyebath, rinsed with water and dried. The polyester fiber is colored in a beautiful blue, washable and very light, heat-setting and pleating-fast shade. Co-treated wool and cotton are well reserved.
Andere zum Färben von Acetat- und Triacetatkunstseide und Polyesterfasern gut geeignete Mischungen sind z. B. l,5-Dihydroxy-4,8-diamino-2-(4'-methoxy)-phenylanthrachinon und l,5-Dihydroxy-4,8-diamino - 2 - (2' - hydroxy - 5' - amyl) - phenylanthrachinon, 1,5 - Dihydroxy - 4,8 - diamino - 2 - (4'-methoxy)-phenylanthrachinon und l,5-Dihydroxy-4,8-diamino-2-(4'-äthoxy)-phenylanthrachinon sowie 1,5-Dihydroxy - diamino - 2 - (4' - hydroxy) - phenylanthrachinon und l,5-Dihydroxy-4,8-diamino-2-(4'-äthoxy)-phenylanthrachinon. In gleicher Konzentration angewandt, ergeben diese Gemische stärkere Färbungen alsderFarbstoffl,5-Dihydroxy-4,8-diamino-2-(4'-methoxy)-phenylanthrachinon allein. In hellen Färbungen bleiben die Nachzüge weiß.Other blends well suited for dyeing acetate and triacetate rayon and polyester fibers are z. B. 1,5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone and 1,5-dihydroxy-4,8-diamino - 2 - (2 '- hydroxy - 5' - amyl) - phenylanthraquinone, 1,5 - dihydroxy - 4,8 - diamino - 2 - (4'-methoxy) phenylanthraquinone and 1,5-dihydroxy-4,8-diamino-2- (4'-ethoxy) phenylanthraquinone as well as 1,5-dihydroxy-diamino-2- (4'-hydroxy) -phenylanthraquinone and 1,5-dihydroxy-4,8-diamino-2- (4'-ethoxy) -phenylanthraquinone. Used in the same concentration, these mixtures give stronger colors than the dye, 5-dihydroxy-4,8-diamino-2- (4'-methoxy) -phenylanthraquinone alone. The stripes remain white in light colors.
Claims (1)
Deutsche Patentschrift Nr. 864425;
USA.-Patentschrift Nr. 2 773 071.Considered publications:
German Patent No. 864425;
U.S. Patent No. 2,773,071.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH894338X | 1958-03-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1144678B true DE1144678B (en) | 1963-03-07 |
Family
ID=4546083
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DES62204A Pending DE1144678B (en) | 1958-03-19 | 1959-03-18 | Dyeing of polyamide, cellulose ester and polyterephthalic acid ester fibers from aqueous suspension |
Country Status (5)
Country | Link |
---|---|
US (1) | US3043646A (en) |
CH (2) | CH351253A (en) |
DE (1) | DE1144678B (en) |
FR (1) | FR1218936A (en) |
GB (1) | GB894338A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1266263B (en) * | 1965-06-04 | 1968-04-18 | Hansjoachim Von Hippel Dr Ing | Face conveyor anchoring station with support device for the extension of the line at the passage of the conveyor from the face into the line |
DE1278639B (en) * | 1963-04-10 | 1968-09-26 | Ici Ltd | Process for the production of water-insoluble anthraquinone dyes |
US4255151A (en) | 1978-10-24 | 1981-03-10 | Bayer Aktiengesellschaft | Process for dyeing and printing cellulose fibres |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3265460A (en) * | 1960-03-22 | 1966-08-09 | Allied Chem | Dyeing of synthetic fibers |
DE1184878B (en) * | 1961-12-23 | 1965-01-07 | Bayer Ag | Process for the preparation of anthraquinone dyes |
NL287697A (en) * | 1962-01-12 | |||
NL292479A (en) * | 1962-05-11 | |||
BE636100A (en) * | 1962-08-13 | |||
DE1228734B (en) * | 1963-07-04 | 1966-11-17 | Bayer Ag | Process for the preparation of anthraquinone dyes |
BE661652A (en) * | 1964-03-25 | |||
GB1081890A (en) * | 1965-07-19 | 1967-09-06 | Ici Ltd | Anthraquinone dyestuffs |
GB1317281A (en) * | 1970-03-04 | 1973-05-16 | Ici Ltd | Colouration of polyesters |
NL7204838A (en) * | 1971-04-14 | 1972-10-17 | ||
DE3040102A1 (en) * | 1980-10-24 | 1982-06-03 | Merck Patent Gmbh, 6100 Darmstadt | DICHROITIC ANTHRACHINONE DYES, THIS CONTAINING LIQUID CRYSTALINE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT |
DE3115762A1 (en) * | 1981-04-18 | 1982-11-11 | Merck Patent Gmbh, 6100 Darmstadt | "DICHROITIC ANTHRACHINONE DYES, THIS CONTAINING LIQUID CRYSTAL DIELECTRICS AND ELECTROOPRIC DISPLAY ELEMENT" |
DE19813139C1 (en) | 1998-03-25 | 1999-09-23 | Schober Werkzeug & Maschbau | Work conveyor for punch |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE864425C (en) * | 1951-01-30 | 1953-01-26 | Gen Aniline & Film Corp | Process for the production of anthraquinone dyes which are resistant to gas shrinkage and are particularly suitable for dyeing acetate silk |
US2773071A (en) * | 1954-01-26 | 1956-12-04 | Interchem Corp | Anthraquinone dyes |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE446563C (en) * | 1925-04-17 | 1927-07-06 | I G Farbenindustrie Akt Ges | Process for the preparation of dyes of the anthraquinone series |
US2922691A (en) * | 1955-08-02 | 1960-01-26 | Ciba Ltd | Anthraquinone dyes and polyethylene terephthalate fibers dyed therewith |
GB800606A (en) * | 1957-12-30 | 1958-08-27 | Ici Ltd | Process for colouring aromatic polyester fibres |
-
1958
- 1958-03-19 CH CH351253D patent/CH351253A/en unknown
-
1959
- 1959-03-09 CH CH355126D patent/CH355126A/en unknown
- 1959-03-16 US US799442A patent/US3043646A/en not_active Expired - Lifetime
- 1959-03-17 FR FR789596A patent/FR1218936A/en not_active Expired
- 1959-03-18 GB GB9446/59A patent/GB894338A/en not_active Expired
- 1959-03-18 DE DES62204A patent/DE1144678B/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE864425C (en) * | 1951-01-30 | 1953-01-26 | Gen Aniline & Film Corp | Process for the production of anthraquinone dyes which are resistant to gas shrinkage and are particularly suitable for dyeing acetate silk |
US2773071A (en) * | 1954-01-26 | 1956-12-04 | Interchem Corp | Anthraquinone dyes |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1278639B (en) * | 1963-04-10 | 1968-09-26 | Ici Ltd | Process for the production of water-insoluble anthraquinone dyes |
DE1266263B (en) * | 1965-06-04 | 1968-04-18 | Hansjoachim Von Hippel Dr Ing | Face conveyor anchoring station with support device for the extension of the line at the passage of the conveyor from the face into the line |
US4255151A (en) | 1978-10-24 | 1981-03-10 | Bayer Aktiengesellschaft | Process for dyeing and printing cellulose fibres |
Also Published As
Publication number | Publication date |
---|---|
GB894338A (en) | 1962-04-18 |
CH351253A (en) | 1961-01-15 |
US3043646A (en) | 1962-07-10 |
CH355126A (en) | 1961-06-30 |
FR1218936A (en) | 1960-05-13 |
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