DE1021826B - Process for dyeing polyester fibers - Google Patents
Process for dyeing polyester fibersInfo
- Publication number
- DE1021826B DE1021826B DEF17706A DEF0017706A DE1021826B DE 1021826 B DE1021826 B DE 1021826B DE F17706 A DEF17706 A DE F17706A DE F0017706 A DEF0017706 A DE F0017706A DE 1021826 B DE1021826 B DE 1021826B
- Authority
- DE
- Germany
- Prior art keywords
- phosphoric acid
- dye
- dyeing
- esters
- formula
- 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.)
- Granted
Links
- 238000004043 dyeing Methods 0.000 title claims description 17
- 239000000835 fiber Substances 0.000 title claims description 11
- 229920000728 polyester Polymers 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 235000011007 phosphoric acid Nutrition 0.000 claims description 16
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000003016 phosphoric acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 27
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 14
- 239000007859 condensation product Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 8
- 150000005374 primary esters Chemical class 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 5
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960002903 benzyl benzoate Drugs 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 229940055577 oleyl alcohol Drugs 0.000 description 4
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 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 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001584775 Tunga penetrans Species 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229940095102 methyl benzoate Drugs 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 150000008027 tertiary esters Chemical class 0.000 description 3
- AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229940081735 acetylcellulose Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000008028 secondary esters Chemical class 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Chemical class 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- -1 aryl benzoate Chemical compound 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000009970 yarn dyeing Methods 0.000 description 1
Classifications
-
- 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
- D06P1/60—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 polyethers
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
-
- 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
- D06P1/60—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 polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
-
- 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
- D06P1/60—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 polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6138—Polymerisation products of glycols, e.g. Carbowax, Pluronics
-
- 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
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65125—Compounds containing ester groups
-
- 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
- D06P1/651—Compounds without nitrogen
- D06P1/6515—Hydrocarbons
- D06P1/65156—Halogen-containing hydrocarbons
-
- 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
- D06P1/667—Organo-phosphorus compounds
-
- 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
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
DEUTSCHESGERMAN
Zum Färben von Polyesterfasergut werden hauptsächlich Dispersionsfarbstoffe verwendet, wie sie seit langem zum Färben von Celluloseacetatfasern benutzt werden. Beispielsweise seien als derartige Farbstoffe genannt: das 2,4-Dinitro-4'-oxydiphenylamin, einfache Azofarbstoffe, wie p-Nitranilin ->~ Anilin, Mono-N-acetyl-p-phenylendiamin ->- p-Kresol, Derivate des Anthrachinone oder Naphthochinons, wie 1-Methylamino-/?-oxyäthylamino-anthrachinon, bromiertes 1-Oxy-4-amino-5,8-monochinonimin und ähnliche.For dyeing polyester fiber material, disperse dyes are mainly used, as they have been since have long been used for dyeing cellulose acetate fibers. Examples of such dyes are called: 2,4-dinitro-4'-oxydiphenylamine, simple azo dyes such as p-nitroaniline -> ~ aniline, mono-N-acetyl-p-phenylenediamine -> - p-cresol, derivatives of anthraquinone or naphthoquinone, such as 1-methylamino - /? - oxyäthylamino-anthraquinone, brominated 1-oxy-4-amino-5,8-monoquinone imine and the like.
Die. Dispersionsfarbstoffe werden auf die Polyesterfasern in möglichst feinverteiltem Zustand entweder unter Druck bei Temperaturen um etwa 120° oder bei Kochtemperatur mit Farbstoffträgern (Dispersionen bzw. Emulsionen von z. B. Diphenyl, Chlorbenzol, Oxydiphenyl, Benzoesäure, Benzoesäurealkyl-, -aralkyl- oder -arylester, ζ. B. Benzoesäuremethyl- oder -benzylester, Salicylsäureester u. dgl.) aufgefärbt. Nicht nur die Reib-, Schweiß- und Waschechtheit, sondern vor allem die Egalität der Färbungen hängen weitgehend von dem Verteilungszustand des Farbstoffes während des Färbens ab. Es bereitet aber große Schwierigkeiten, die Farbstoffdispersionen während einer längeren Färbedauer gleichmäßig zu erhalten. Vielfach brechen die Dispersionen vorzeitig. Dies führt in vielen Fällen zur Ablagerung schmieriger Produkte an den Gefäßwänden, zur Fleckenbildung auf den zu färbenden Materialien, zu geringerer Ausnutzung der Färbebäder und vor allen Dingen zu ungleichmäßigen Färbungen.The. Disperse dyes are applied to the polyester fibers in as finely divided a state as possible either under pressure at temperatures around 120 ° or at Cooking temperature with color carriers (dispersions or emulsions of e.g. diphenyl, chlorobenzene, oxydiphenyl, Benzoic acid, alkyl, aralkyl or aryl benzoate, ζ. B. methyl or benzyl benzoate, Salicylic acid esters and the like) colored. Not only the rub, sweat and wash fastness, but above all that Levels of dyeing depend largely on the state of distribution of the dye during dyeing away. However, it is very difficult to keep the dye dispersions uniform over a long period of dyeing to obtain. In many cases, the dispersions break prematurely. In many cases this leads to deposits greasy products on the vessel walls, causing stains on the materials to be colored, to less Utilization of the dye baths and, above all, uneven dyeing.
Es wurde nun gefunden, daß man zu erheblich beständigeren Farbstoffdispersionen und damit zu gleichmäßigeren Färbungen von Polyesterfasergut gelangt, wenn man beim Färben oberflächenaktive Ester der Phosphorsäure, insbesondere der Orthophosphorsäure, mitverwendet.It has now been found that dye dispersions that are considerably more stable and thus more uniform can be obtained Dyeing of polyester fiber material is achieved if the surface-active ester of the dyeing process is used Phosphoric acid, especially orthophosphoric acid, is also used.
Das vorliegende Verfahren eignet sich sowohl für das Färben von Gespinsten und Geweben aus Polyesterfaser allein oder von Mischungen mit anderen natürlichen oder synthetischen Fasern, wie z. B. Wolle, Baumwolle, Seide, Leinen, Regeneratcellulose- oder Regenerateiweißfasern, Acetylcellulose, insbesondere Triacetylcellulose, vollsynthetische Fasern, wobei zwischen polykondensierten und polymerisierten Fasern grundsätzlich kein Unterschied ist. Als besonderes Merkmal tritt bei solchen Fasergemischen, insbesondere beim Färben dunkler Töne, die ausgezeichnete Reibechtheit in Erscheinung.The present process is suitable for dyeing spun threads and fabrics made of polyester fibers alone or of mixtures with other natural or synthetic fibers, such as. B. wool, cotton, silk, Linen, regenerated cellulose or regenerated white fibers, acetyl cellulose, especially triacetyl cellulose, fully synthetic Fibers, with basically no difference between polycondensed and polymerized fibers is. A special feature of such fiber mixtures, especially when dyeing dark shades, is the excellent rub fastness in appearance.
Als Phosphorsäure, wie sie den in Frage kommenden Estern zugrunde liegt, kommt vorzugsweise Orthophosphorsäure
in Betracht, jedoch können auch Ester der wasserärmeren Formen derselben, nämlich der Pyro-,
Meta- oder Polyphosphorsäuren verwendet werden. Als oberflächenaktive Ester der Phosphorsäuren kommen
sowohl primäre, sekundäre oder tertiäre Ester in Frage, die mindestens einen hydrophoben Kohlenwasserstoffrest
Verfahren zum Färben
von PolyesterfasernOrthophosphoric acid is preferably used as the phosphoric acid, as it is based on the esters in question, but esters of the lower-water forms thereof, namely pyro-, meta- or polyphosphoric acids, can also be used. Primary, secondary or tertiary esters, which contain at least one hydrophobic hydrocarbon radical, can be used as surface-active esters of phosphoric acids
of polyester fibers
Anmelder:Applicant:
Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,
Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45
Dr. Joseph Nüsslein, Frankfurt/M.,Dr. Joseph Nüsslein, Frankfurt / M.,
und Dr. Wilhelm Happe, Schwalbach (Taunus),and Dr. Wilhelm Happe, Schwalbach (Taunus),
sind als Erfinder genannt wordenhave been named as inventors
von 7 oder mehr Kohlenstoffatomen enthalten. Die Ester können sich von ein- oder mehrwertigen Hydroxylverbindungen ableiten, die einen derartigen Kohlenwasserstoffrest enthalten. Beispielsweise kommen gesättigte oder ungesättigte aliphatische, aromatische, araliphatische, aliphatisch-aromatische, alicyclische oder heterocyclische Hydroxylverbindungen in Frage. Neben den direkten Estern, bei denen der hydrophobe Kohlenwasserstoffrest über ein Sauerstoffatom direkt mit dem Phosphoratom verbunden ist, können auch indirekte Ester verwendet werden, bei denen der hydrophobe Kohlenwasserstoffrest über eine Brücke von einer oder mehreren hydrophilen Gruppe(n) an das Phosphorsäureradikal gebunden ist. Als hydrophiles Brückenglied kommen beispielsweise mehrwertige Alkohole, wie Sorbit, Erythrit, Glycerin, Glykol oder Polyglykole, Aminoalkohole oder deren Polyäther, in Frage. In diesem Fall kann der hydrophobe Rest ätherartig an das Brückenglied geknüpft sein. Er kann jedoch auch esterartig oder amidartig eingebaut sein.of 7 or more carbon atoms. The esters can be derived from mono- or polyvalent hydroxyl compounds derive that contain such a hydrocarbon radical. For example, there are saturated ones or unsaturated aliphatic, aromatic, araliphatic, aliphatic-aromatic, alicyclic or heterocyclic Hydroxyl compounds in question. In addition to the direct esters, in which the hydrophobic hydrocarbon residue is directly connected to the phosphorus atom via an oxygen atom, indirect esters can also be used in which the hydrophobic hydrocarbon radical is bridged by one or more hydrophilic Group (s) is bound to the phosphoric acid radical. As a hydrophilic bridge member, for example polyhydric alcohols such as sorbitol, erythritol, glycerol, glycol or polyglycols, amino alcohols or their Polyether, in question. In this case, the hydrophobic residue can be linked to the pontic in an ethereal manner. He however, it can also be incorporated in an ester-like or amide-like manner.
Ferner kommen Verbindungen in Frage, die durch Polykondensation von mehrfach veresterungsfähigen Phosphorsäurederivaten, beispielsweise Phosphoroxychlorid, mit mehrwertigen Alkoholen entstanden sind.Compounds that are capable of being esterified more than once by polycondensation are also suitable Phosphoric acid derivatives, for example phosphorus oxychloride, have arisen with polyhydric alcohols.
Die genannten Ester der Phosphorsäuren könnenThe mentioned esters of phosphoric acids can
sowohl auf Polyesterflocke als auch beim Färben von Polyestergarn im Garnfärbeapparat oder beim Färben von Stückware auf der Haspelkufe sowie auf dem offenen oder geschlossenen Jigger und anderen zum Färben der genannten Kunstfasern üblichen Apparaten und Systemen eingesetzt werden.both on polyester flakes and when dyeing polyester yarn in the yarn dyeing machine or when dyeing of piece goods on the reel skid as well as on the open or closed jigger and others for dyeing the mentioned synthetic fibers usual apparatus and systems can be used.
709 847/316709 847/316
Die Wirksamkeit der Phosphorsäureester in bezug auf Egalität und Reinheit der Färbungen wird besonders deutlich, wenn Farbstoffe verwendet werden, die z. B. auf Grund ihrer Kristallisations- oder Agglomerierfreudigkeit sehr leicht zum Teeren neigen, was auch mit einer gewissen Schwerverträglichkeit solcher Farbstoffe mit den benutzten Carriers zusammenhängen kann.The effectiveness of the phosphoric acid esters with regard to the levelness and purity of the dyeings is particularly important clearly when dyes are used which e.g. B. due to their tendency to crystallize or agglomerate tend to tar very easily, which is also due to a certain intolerance of such dyes may be related to the carriers used.
Polyäthylenglykolterephthalatfasergewirk dem Jigger im Flottenverhältnis 1 0Knitted polyethylene glycol terephthalate fiber the jigger in a fleet ratio of 1 0
NH OHNH OH
-ι—Br.- I - Br.
wird auf 20 mit einer Flotte 2 °/0 becomes on 20 with a fleet 2 ° / 0
JggJgg
gefärbt, die 6 % einer Emulsion aus etwa 80 Teilen Benzoesäurebenzylester und etwa 20 Teilen eines Kondensationsproduktes aus Dodecylphenol und 13 Mol Äthylenoxyd als Carrier und 2% des Farbstoffes der Formelcolored, the 6% of an emulsion of about 80 parts of benzyl benzoate and about 20 parts of a condensation product from dodecylphenol and 13 mol of ethylene oxide as a carrier and 2% of the dye of the formula
O NH · CH3 O NH • CH 3
des Farbstoffes der Formelof the dye of the formula
NH.NH.
OHOH
NH-CO-CH, CHoNH-CO-CH, CHo
O NH-CH.-CHo-OHO NH-CH.-CHo-OH
0,2 % des Farbstoffes der Formel0.2% of the dye of the formula
NH2 NH 2
O2N 0 NH2 sowie 0,3% des Farbstoffes der FormelO 2 N 0 NH 2 and 0.3% of the dye of the formula
OHOH
und 2% des primären Esters aus Orthophosphorsäure und dem Kondensationsprodukt von Oleylalkohol mit 4 Mol Äthylenoxyd enthält. Die Färbung wird in der im Beispiel 1 beschriebenen Weise vorgenommen. Die erhaltene Grünfärbung ist beträchtlich ruhiger und ein wenig blauer als eine entsprechend ohne Mitverwendung des Phosphorsäureesters hergestellte Färbung.and 2% of the primary ester of orthophosphoric acid and the condensation product of oleyl alcohol with Contains 4 moles of ethylene oxide. The coloring is carried out in the manner described in Example 1. the The green color obtained is considerably quieter and a little bluer than a corresponding one without use the coloration produced by the phosphoric acid ester.
An Stelle des Salicylsäuremethylesters kann man auch andere Carrier, beispielsweise Benzoesäuremethylester, verwenden.Instead of the methyl salicylate, other carriers can also be used, for example methyl benzoate, use.
In der im Beispiel 1 beschriebenen Weise färbt man Polyesterfasergewirk mit einer Flotte, die folgende Komponenten enthält: 6% einer 80°/0igen Chlornaphthalindispersion, 0,5% des Farbstoffes der FormelIn the manner described in Example 1 is dyed Polyesterfasergewirk with a liquor which contains the following components: 6% of a 80 ° / 0 Chlornaphthalindispersion strength, 0.5% of the dye of the formula
NHoNHo
NH,NH,
■ /■ /
4040
4545
NH · CO · CH3 CH3 NH • CO • CH 3 CH 3
enthält.contains.
Durch etwa fünf Passagen des gut vorgewaschenen Materials durch die kochende Flotte netzt man gut vor, kühlt die Flotte auf etwa 40° ab und gibt die Farbstoffdispersion zu. Anschließend wird langsam aufgeheizt, wobei bei 70° 2 bis 10 g pro Liter des technischen tertiären Phosphorsäureesters aus dem Kondensationsprodukt von Dodecylalkohol und 4 Mol Äthylenoxyd, das noch Anteile des entsprechenden primären und sekundären Esters enthalten kann, zusammen mit dem Carrier zugegeben werden. Die Temperatur wird langsam auf fast 100° gesteigert und das Material 3 Stunden bei dieser Temperatur gefärbt.By about five passages of the well-pre-washed material through the boiling liquor, one pre-wets well, cools the liquor to about 40 ° and adds the dye dispersion. Then it is slowly heated up, wherein at 70 ° 2 to 10 g per liter of the technical tertiary phosphoric acid ester from the condensation product of Dodecyl alcohol and 4 moles of ethylene oxide, which still contains proportions of the corresponding primary and secondary ester can be added together with the carrier. The temperature is slowly increased to almost 100 ° and dyed the material for 3 hours at that temperature.
Die erhaltene blaustichige Grünfärbung ist wesentlich ruhiger als die gleiche Färbung, die ohne den Zusatz des genannten Phosphorsäureesters hergestellt wird.The bluish green coloration obtained is much quieter than the same coloration obtained without the addition of the called phosphoric acid ester is produced.
Polyäthylenglykolterephthalatfasergewirk wird auf dem Jigger im Flottenverhältnis 1:20 mit einer Flotte gefärbt, die als Carrier 6% einer 80°/0igen Emulsion von Salicylsäuremethylester, 2°/0 des Farbstoffes der FormelPolyäthylenglykolterephthalatfasergewirk colored on the jigger liquor ratio of 1:20, with a liquor which contains as carriers 6% of a 80 ° / 0 emulsion of methyl salicylate, 2 ° / 0 of the dye of the formula
NO»NO »
0,045% des Farbstoffes der Formel
NO,0.045% of the dye of the formula
NO,
O0N-O 0 N-
NHNH
>— OH> - OH
0,0045% des Farbstoffes der Formel0.0045% of the dye of the formula
0 NH · CH3 0 NH • CH 3
6060
6565
0 NH-CHo-CH2-OH0 NH-CHo-CH 2 -OH
und 2% des primären Esters aus Orthophosphorsäure und dem Kondensationsprodukt aus Olevlalkohol und 8 Mol Glykol.and 2% of the primary ester of orthophosphoric acid and the condensation product of oleic alcohol and 8 moles of glycol.
Die ohne den Zusatz des Phosphorsäureesters durchgeführte Beigefärbung ist wesentlich rußiger und un-The beige coloring carried out without the addition of the phosphoric acid ester is significantly more sooty and un-
ruhiger als die gemäß der vorstehend angegebenen Arbeitsweise erhaltene Färbung.quieter than the dyeing obtained according to the procedure given above.
10 g Polyäthylenglykolterephthalatfasergewirk werden im Flottenverhältnis 1: 40 1 x/2 Stunden bei einer Temperatur nahe dem Kochpunkt mit einer Flotte gefärbt, die 6 °/0 des im Beispiel 1 beschriebenen Carriers, 2 °/0 des Farbstoffes der Formel10 g Polyäthylenglykolterephthalatfasergewirk be in a liquor ratio 1: x stained 2 hours at a temperature close to the boiling point with a liquor 40 1/6 ° / 0 of the carrier described in Example 1, 2 ° / 0 of the dye of the formula
Polyäthylenglykolterephthalatfasergewirk wird in der im Beispiel 4 beschriebenen Arbeitsweise mit einer Flotte gefärbt, die 6 % einer 80%igen Benzoesäuremethylesteremulsion, 2% des Farbstoffes der FormelPolyethylene glycol terephthalate knitted fabric is in the procedure described in Example 4 with a liquor colored, the 6% of an 80% methyl benzoate emulsion, 2% of the dye of the formula
OHOH
NH,NH,
NH,NH,
NO2 NO 2
und 20I0 des im Beispiel2 genannten Phosphorsäureesters enthält.and 2 0 I 0 of the phosphoric acid ester mentioned in Example 2 contains.
Die erhaltene Färbung ist voller und reiner als die ohne den Zusatz des Phosphorsäurederivates hergestellte Färbung.The coloration obtained is fuller and purer than that produced without the addition of the phosphoric acid derivative Coloring.
Zu ähnlichen Ergebnissen gelangt man, wenn man an Stelle des Phosphorsäureesters des Kondensationsproduktes aus Oleylalkohol und 4 Mol Äthylenoxyd den entsprechenden Ester auf Dodecylalkoholbasis einsetzt.Similar results are obtained if, instead of the phosphoric acid ester, the condensation product of oleyl alcohol and 4 moles of ethylene oxide is used corresponding esters based on dodecyl alcohol are used.
ν γν γ
NH-CO-CH3 CH3 NH-CO-CH 3 CH 3
und 2 % des primären Phosphorsäureesters des Kondensationsproduktes aus Oleylalkohol und 4 Mol Glykol enthält. Die erhaltene Gelbfärbung ist voller und reiner als die ohne den Zusatz des Phosphorsäureesters hergestellte Färbung.and 2% of the primary phosphoric acid ester of the condensation product from oleyl alcohol and 4 moles of glycol. The yellow color obtained is fuller and purer than the color produced without the addition of the phosphoric acid ester.
An Stelle des vorstehend genannten Phosphorsäureesters kann man auch die gleiche Menge des sekundären Esters aus Orthophosphorsäure und Dodecylalkohol verwenden.Instead of the above-mentioned phosphoric acid ester, the same amount of the secondary Use esters made from orthophosphoric acid and dodecyl alcohol.
a5 Beispiel 7 a 5 Example 7
In der im Beispiel 4 beschriebenen Arbeitsweise färbt manPolyäthylenglykolterephthalatfasern mit einer Flotte, die 2 °/0 eines Farbstoffgemisches, das 88,38 % des Farbstoffes der FormelIn the manner described in Example 4 Operation manPolyäthylenglykolterephthalatfasern dyed with a liquor containing 2 ° / 0 of a dye mixture containing 88.38% of the dye of the formula
NH2 OHNH 2 OH
In der im Beispiel 4 beschriebenen Weise färbt man Polyäthylenglykolterephthalatfasergewirk mit einer Flotte, die 6 % einer 80°/0igen Chlorbenzolemulsion, 2 °/0 des Farbstoffes der FormelIn the manner described in Example 4 is dyed Polyäthylenglykolterephthalatfasergewirk with a liquor containing 6% of a 80 ° / 0 emulsion strength chlorobenzene, 2 ° / 0 of the dye of the formula
NH OHNH OH
NH-CO-CHo CHoNH-CO-CHo CHo
Br0 Br 0
2,52 % des Farbstoffes der Formel2.52% of the dye of the formula
NH2 NH,NH 2 NH,
O NH2 O NH 2
2% des Farbstoffes der Formel
NHo2% of the dye of the formula
NHo
4545
OHOH
NH-CO-CH3 CH3 NH-CO-CH 3 CH 3
und 4% des primären Esters aus Orthophosphorsäure und dem Kondensationsprodukt aus Dodecylalkohol und 4 Mol Glykol enthält.and 4% of the primary ester of orthophosphoric acid and the condensation product of dodecyl alcohol and Contains 4 moles of glycol.
Die erhaltene Grünfärbung ist etwas lebhafter und ruhiger als die ohne Mitverwendung des Phosphorsäureesters erzielte Färbung. An Stelle des vorstehend genannten primären Esters kann man auch den tertiären Ester der Orthophosphorsäure mit dem Kondensationsprodukt aus Oleylalkohol und 8 Mol Äthylenoxyd oder 2% eines tertiären polykondensierten Phosphorsäureesters verwenden, der durch Kondensation von 1 Mol Phosphoroxychlorid mit 1 Mol Polyäthylenglykol vom Durchschnittsmolekulargewicht 300 in der ersten Phase und 1 Mol des Kondensationsproduktes aus Dodecylalkohol und Diglykol in der zweiten Phase hergestellt ist. NO2 The green color obtained is somewhat livelier and quieter than the color obtained without the use of the phosphoric ester. Instead of the above-mentioned primary ester, the tertiary ester of orthophosphoric acid with the condensation product of oleyl alcohol and 8 moles of ethylene oxide or 2% of a tertiary polycondensed phosphoric acid ester can be used, which is obtained by condensation of 1 mole of phosphorus oxychloride with 1 mole of polyethylene glycol with an average molecular weight of 300 in the first Phase and 1 mole of the condensation product is made from dodecyl alcohol and diglycol in the second phase. NO 2
und 9,10 % Salz aufweist, und 2 % des primären Esters aus Orthophosphorsäure und dem Kondensationsprodukt aus Dodecylalkohol und 4 Mol Äthylenoxyd enthält. Die so erhaltene Gelbfärbung ist stärker und reiner als die ohne den Zusatz des Phosphorsäureesters erhaltene Färbung.and 9.10% salt, and 2% of the primary ester from orthophosphoric acid and the condensation product of dodecyl alcohol and 4 moles of ethylene oxide. the The yellow coloration obtained in this way is stronger and purer than that obtained without the addition of the phosphoric acid ester Coloring.
Polyäthylenglykolterephthalatware wird im Flottenverhältnis 1 : 40 1 1I2 Stunden kochend mit einer Flotte gefärbt, die 2% eines Farbstoffgemisches, das 88,38 % des Farbstoffes der FormelPolyethylene glycol terephthalate ware is dyed in a liquor ratio of 1: 40 1 1 I for 2 hours at the boil with a liquor containing 2% of a dye mixture and 88.38% of the dye of the formula
NHoNHo
OHOH
70 NH-CO-CHo CH, 70 NH-CO-CHo CH,
2,52 % des Farbstoffes der Formel2.52% of the dye of the formula
NH2 NH2 NH 2 NH 2
NO9 NO 9
H2NH 2 N
NH,NH,
16,66 °/o der Verbindung
NH,16.66 ° / o of the compound
NH,
NH-CHo-CH-O-HNH-CHo-CH-O-H
NO2
6,67 °/0 der VerbindungNO 2
6.67 ° / 0 of the compound
und 9,10 °/0 Salz aufweist, 6 % des Carriers auf Basis von Benzylbenzoat und 2 % eines tertiären polykondensierten Phosphorsäureesters enthält, der durch Kondensation von 1 Mol Phosphoroxychlorid mit 1 Mol Polyäthylenglykol vom Durchschnittsmolekulargewicht 300 in der ersten Reaktionsstufe und 1 Mol des Kondensationsproduktes von Dibutylkresol und 4 Mol Äthylenoxyd in der zweiten Stufe erhalten wird. Die erhaltene Gelbfärbung ist erheblich reiner als die ohne den Zusatz des Phosphorsäurederivates hergestellte Färbung.and 9.10 ° / 0 salt, 6% of the carrier based on benzyl benzoate and 2% of a tertiary polycondensed phosphoric acid ester, which by condensation of 1 mole of phosphorus oxychloride with 1 mole of polyethylene glycol with an average molecular weight of 300 in the first reaction stage and 1 mole of the condensation product is obtained from dibutyl cresol and 4 moles of ethylene oxide in the second stage. The yellow coloration obtained is considerably purer than the coloration produced without the addition of the phosphoric acid derivative.
Polyäthylenglykolterephthalatfasern werden nach der im Beispiel 8 beschriebenen Arbeitsweise mit einer Flotte gefärbt, die 10% eines Farbstoffgemisches, das 44,45% der VerbindungPolyethylene glycol terephthalate fibers are made according to the procedure described in Example 8 with a liquor colored, the 10% of a dye mixture, the 44.45% of the compound
NH,NH,
NO2 NO 2
und 101V0 der Verbindungand 10 1 V 0 of the connection
O NH,O NH,
O, NO, N
NH,NH,
H-N O NH,H-N O NH,
22,22% der Verbindung22.22% of the compound
HO 0 NH-CH9-CH-OHHO 0 NH-CH 9 -CH-OH
aufweist, 8 % Benzylbenzoatemulsion, 0,5 % des tertiären Esters aus Orthophosphorsäure und dem Kondensationsprodukt aus Dodecylalkohol, 4 Mol Äthylenoxyd und I % des im Beispiel 8 genannten polykondensierten Phosphorsäureesters enthält. Man erhält eine etwas vollere und blaustichigere Schwarzfärbung, als sie ohne den Zusatz der genannten Phosphorsäureester erzielt wird.has, 8% benzyl benzoate emulsion, 0.5% of the tertiary Esters of orthophosphoric acid and the condensation product of dodecyl alcohol, 4 moles of ethylene oxide and I% of the polycondensed phosphoric acid ester mentioned in Example 8 contains. You get a something fuller and more bluish black coloration than is achieved without the addition of the phosphoric acid ester mentioned.
Claims (2)
Deutsche Patentschriften Nr. 605 973,667 744,694 178.Considered publications:
German patent specification No. 605 973,667 744,694 178.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE548539D BE548539A (en) | 1955-06-10 | ||
| DEF17706A DE1021826B (en) | 1955-06-10 | 1955-06-10 | Process for dyeing polyester fibers |
| GB1786856A GB828924A (en) | 1955-06-10 | 1956-06-08 | Process for dyeing polyester fibres |
| FR1151353D FR1151353A (en) | 1955-06-10 | 1956-06-11 | Poly-ester fiber dyeing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF17706A DE1021826B (en) | 1955-06-10 | 1955-06-10 | Process for dyeing polyester fibers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1021826B true DE1021826B (en) | 1958-01-02 |
| DE1021826C2 DE1021826C2 (en) | 1958-06-12 |
Family
ID=7088675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF17706A Granted DE1021826B (en) | 1955-06-10 | 1955-06-10 | Process for dyeing polyester fibers |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE548539A (en) |
| DE (1) | DE1021826B (en) |
| FR (1) | FR1151353A (en) |
| GB (1) | GB828924A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0445709A3 (en) * | 1990-03-08 | 1992-02-26 | Hoechst Aktiengesellschaft | Process for the one-bath dyeing and for impacting flame resistance to plane textile materials |
| EP1469121A1 (en) * | 2003-02-28 | 2004-10-20 | Dr. Th. Böhme KG Chem. Fabrik GmbH & Co. | Levelling agent |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3099513A (en) * | 1960-11-01 | 1963-07-30 | Bayer Ag | Process for the dyeing of polyester fibre materials |
| GB1107267A (en) * | 1963-09-23 | 1968-03-27 | Ici Ltd | Method of improving acid dyeability of fibre-forming polymers |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE605973C (en) * | 1930-11-30 | 1934-11-22 | I G Farbenindustrie Akt Ges | Process for the production of ethers from hydroxyl-containing organic compounds and ethylene oxide |
| DE667744C (en) * | 1930-11-30 | 1938-11-19 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
| DE694178C (en) * | 1930-11-30 | 1940-07-27 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
-
0
- BE BE548539D patent/BE548539A/xx unknown
-
1955
- 1955-06-10 DE DEF17706A patent/DE1021826B/en active Granted
-
1956
- 1956-06-08 GB GB1786856A patent/GB828924A/en not_active Expired
- 1956-06-11 FR FR1151353D patent/FR1151353A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE605973C (en) * | 1930-11-30 | 1934-11-22 | I G Farbenindustrie Akt Ges | Process for the production of ethers from hydroxyl-containing organic compounds and ethylene oxide |
| DE667744C (en) * | 1930-11-30 | 1938-11-19 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
| DE694178C (en) * | 1930-11-30 | 1940-07-27 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0445709A3 (en) * | 1990-03-08 | 1992-02-26 | Hoechst Aktiengesellschaft | Process for the one-bath dyeing and for impacting flame resistance to plane textile materials |
| EP1469121A1 (en) * | 2003-02-28 | 2004-10-20 | Dr. Th. Böhme KG Chem. Fabrik GmbH & Co. | Levelling agent |
Also Published As
| Publication number | Publication date |
|---|---|
| BE548539A (en) | |
| DE1021826C2 (en) | 1958-06-12 |
| FR1151353A (en) | 1958-01-29 |
| GB828924A (en) | 1960-02-24 |
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