DE1110609B - Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates - Google Patents
Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalatesInfo
- Publication number
- DE1110609B DE1110609B DEF30024A DEF0030024A DE1110609B DE 1110609 B DE1110609 B DE 1110609B DE F30024 A DEF30024 A DE F30024A DE F0030024 A DEF0030024 A DE F0030024A DE 1110609 B DE1110609 B DE 1110609B
- Authority
- DE
- Germany
- Prior art keywords
- dyeing
- aromatic polyesters
- shaped structures
- linear aromatic
- polyethylene terephthalates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004043 dyeing Methods 0.000 title claims description 8
- 125000003118 aryl group Chemical group 0.000 title claims description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims description 6
- -1 polyethylene terephthalates Polymers 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 229920000728 polyester Polymers 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 206010039587 Scarlet Fever Diseases 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
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000271 synthetic detergent 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
-
- 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
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Es wurde gefunden, daß man echte Färbungen und Drucke auf geformten Gebilden, wie Fasern, Geweben oder Folien, aus linearen aromatischen Polyestern, insbesondere Polyäthylenterephthalaten, erhält, wenn man hierzu wäßrige Dispersionen von Farbstoffen der nachstehenden allgemeinen FormelIt has been found that real dyeings and prints can be produced on shaped structures such as fibers and fabrics or films made from linear aromatic polyesters, especially polyethylene terephthalates, if one for this purpose aqueous dispersions of dyes of the following general formula
OHOH
CO-NHCO-NH
CHo-O'CHo-O '
CH,CH,
Verfahren zum FärbenMethod of dyeing
und Bedrucken von geformten Gebildenand printing of shaped structures
aus linearen aromatischen Polyestern,made of linear aromatic polyesters,
insbesondere Polyäthylenterephthalatenin particular polyethylene terephthalates
Anmelder:Applicant:
Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,
Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45
Dr. Rudolf Kühne, Frankfurt/M.-Unterliederbach,
Dr. Helmut Lindner, Frankfurt/M.-Sindlingen,Dr. Rudolf Kühne, Frankfurt / M.-Unterliederbach,
Dr. Helmut Lindner, Frankfurt / M.-Sindlingen,
und Dr. Wilhelm Happe,and Dr. Wilhelm Happe,
Schwalbach über Frankfurt/M.-Höchst,Schwalbach via Frankfurt / M.-Höchst,
sind als Erfinder genannt wordenhave been named as inventors
in welcher R1 ein Wasserstoffatom, eine Alkyl-, Aryl-, Alkoxy-, Aryloxy-, Trifluormethyl- oder Carbonsäurealkylestergruppe und R2 ein Wasserstoffatom, eine Alkylgruppe, Alkoxygruppe oder ein Halogenatom bedeutet, verwendet. Das Färben erfolgt zweckmäßig in Gegenwart oder Abwesenheit von Carriern bei Temperaturen zwischen etwa 95 und 1050C, vorzugsweise von etwa 1000C, oder nach dem Hochtemperaturverfahren in Abwesenheit von Carriern bei Temperaturen zwischen etwa 120 und 140° C, vorzugsweise zwischen etwa 125 und 130° C, während man beim Drucken die bedruckte Ware zweckmäßig kurzfristig einer trockenen Hitzebehandlung bei höheren Temperaturen, beispielsweise bei etwa 2000C, unterwirft.in which R 1 denotes a hydrogen atom, an alkyl, aryl, alkoxy, aryloxy, trifluoromethyl or carboxylic acid alkyl ester group and R 2 denotes a hydrogen atom, an alkyl group, alkoxy group or a halogen atom. The dyeing is carried out advantageously in the presence or absence of carriers at temperatures between about 95 and 105 0 C, preferably from about 100 0 C, or after the high-temperature process in the absence of carriers at temperatures between about 120 and 140 ° C, preferably between about 125 and 130 ° C, while during printing the printed product useful for shipping a dry heat treatment at higher temperatures, for example at about 200 0 C, is subjected.
Die genannten Farbstoffe werden durch Kuppeln der Diazoniumverbindungen der aus der vorstehend genannten allgemeinen Formel ersichtlichen Struktur mit dem N-[2'-Oxy-3'-naphthoyl]-6-aminobenzdioxanoxan-1,3 in bekannter Weise hergestellt.The dyes mentioned are obtained by coupling the diazonium compounds of the above mentioned general formula with the N- [2'-oxy-3'-naphthoyl] -6-aminobenzdioxanoxane-1,3 produced in a known manner.
Während sich beim Färben bei dem genannten tieferen Temperaturbereich in Gegenwart von Carriern und beim genannten höheren Temperaturbereich in Abwesenheit von Carriern farbtiefe echte Färbungen erzielen lassen, erhält man beim Arbeiten bei demWhile dyeing at the lower temperature range mentioned in the presence of carriers and at the higher temperature range mentioned, in the absence of carriers, depth of color and true colorations can be achieved when working with the
CHS CH S
genannten tieferen Temperaturbereich in Abwesenheit von Carriern ebenfalls echte, wenn auch hellere Farbtöne, die je nach Verwendungszweck des Färbegutes als Pastelltöne sehr geschätzt sind.mentioned lower temperature range in the absence of carriers also real, albeit lighter shades, which, depending on the intended use of the dyed material, are highly valued as pastel shades.
Je nach Wahl der Substituenten R1 und R2 in der vorstehenden allgemeinen Formel erhält man bei Verwendung der entsprechenden Farbstoffe Färbungen in gelborangen bis blauroten Farbtönen. Auch eine kombinierte Anwendung von Farbstoffen, die der vorstehenden allgemeinen Formel entsprechen, ist möglich. Die verfahrensgemäß zur Anwendung gelangenden Farbstoffe zeichnen sich gegenüber den aus der Literatur bekannten Farbstoffen ähnlicher Struktur, jedoch ohne die Dioxangruppierung im Arylidrest der Azokomponente, durch ein besseres Ziehvermögen auf linearen aromatischen Polyestern aus.Depending on the choice of the substituents R 1 and R 2 in the above general formula, dyeings in yellow-orange to blue-red shades are obtained when the corresponding dyes are used. A combined use of dyes which correspond to the above general formula is also possible. The dyes used in accordance with the process are distinguished from the dyes known from the literature of a similar structure, but without the dioxane grouping in the arylide radical of the azo component, by better drawability on linear aromatic polyesters.
5 g Polyäthylenterephthalatfasern in Form eines Gewirkes werden 1 Stunde bei 12O0C in einem Bad gefärbt, das 1 Gewichtsprozent des feindispergierten Farbstoffes der Formel5 g of polyethylene terephthalate fibers in the form of a knitted fabric are dyed for 1 hour at 12O 0 C in a bath containing 1 weight percent of finely dispersed dye of the formula
CH2 CH 2
CH2-OCH 2 -O
109 647/455109 647/455
(erhältlich durch Kuppeln von diazotiertem p-Toluidin mit N-[2'-Oxy-3'-naphthoyl]-6-aminobenzdioxan-l,3) in 200 ml Wasser enthält. Die erhaltene Rotfärbung wird zur Verbesserung der Reibechtheit in einem Bad, das 2 g Natriumdithionit, 2 ml Natronlauge (38° Be) und 0,5 g eines synthetischen Waschmittels (Polyglykoläther) im Liter enthält, 15 Minuten bei 85°C nachbehandelt. Die erhaltene Rotf ärbungzeichnet sich durch ausgeprägte Farbtiefe aus und besitzt gute Echtheiten. Eine Färbung ähnlicher Farbtiefe von praktisch(obtainable by coupling diazotized p-toluidine with N- [2'-oxy-3'-naphthoyl] -6-aminobenzdioxane-1,3) in 200 ml of water. The red coloration obtained is used to improve the rub fastness in a bath, the 2 g sodium dithionite, 2 ml sodium hydroxide solution (38 ° Be) and 0.5 g of a synthetic detergent (polyglycol ether) per liter, post-treated for 15 minutes at 85 ° C. The red coloration obtained is characterized by pronounced depth of color and has good fastness properties. A coloring of a similar depth of color of practical
gleichen Echtheitseigenschaften erhält man, wenn manthe same authenticity properties are obtained if one
bei 1000C färbt und 4 g eines dispergierten Carrierscolors at 100 0 C and 4 g of a dispersed carrier
auf der Basis von o-Phenylphenol im Liter einsetzt,on the basis of o-phenylphenol used per liter,
sonst aber wie vorstehend beschrieben verfährt.otherwise proceed as described above.
Ersetzt man den in diesem Beispiel genannten Farbstoff durch die in der nachfolgenden Tabelle aufgeführten Farbstoffe, so erhält man ebenfalls Färbungen mit guten Echtheitseigenschaften.If the dye mentioned in this example is replaced by that in the table below dyes listed, dyeings with good fastness properties are likewise obtained.
Farbstoff FarbtonDye hue
CO NHCO NH
CH2 CH 2
OHn CO NHOH n CO NH
N=NN = N
CH^O-CH2-CH2-OCH ^ O-CH 2 -CH 2 -O
OHOH
CH3 CH 3
OHOH
CH3O-CH2-CH2-O-CH 3 O-CH 2 -CH 2 -O-
X-N = N-X-N = N-
OHOH
CH3O-CH2-CH2-OOCCH 3 O-CH 2 -CH 2 -OOC
OHOH
CH3O-CH 3 O-
N=NN = N
OCH,OCH,
OHOH
CH2-OCH8X /CH 2 -OCH 8 X /
CR9 CR 9
CH2-O'CH 2 -O '
O,O,
CH2 CH 2
CO-NH-/CO-NH- /
CO NHCO NH
O >O>
CH,-(CH, - (
O,O,
CH2 CH 2
:ch.: ch.
r CH2 r CH 2
CO NH <CO NH <
CH8 CH 8
CH2-(CH 2 - (
NH-NH-
CH2 CH 2
CH2-OCH 2 -O
Orangeorange
ScharlachScarlet fever
OrangerotOrange red
ScharlachScarlet fever
Orangeorange
BordorotBordo red
Orangeorange
25 g Polyäthylenterephthalatgewebe werden mit einer Druckpaste bedruckt, die 50 g des Farbstoffes der Formel25 g of polyethylene terephthalate fabric are printed with a printing paste, the 50 g of the dye the formula
Cl-ςCl-ς
OH,OH,
V-N = Ν—.V-N = Ν—.
CO NH O , CO NH O,
,CH,, CH,
CH2-O'CH 2 -O '
200 g Nafkagummi, 50 g Naphtholdiglykoläther und 700 g Wasser im Kilogramm enthält. Nach dem Trocknen wird 30 Sekunden bei 200° C fixiert und schließlich gemäß Beispiel 1 reduktiv nachbehandelt. Man erhält einen orangefarbenen Druck von guten Echtheitseigenschaften. Contains 200 g Nafka gum, 50 g naphthol diglycol ether and 700 g water per kilogram. After drying is fixed for 30 seconds at 200 ° C and finally reductively aftertreated according to Example 1. You get an orange print with good fastness properties.
Claims (1)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30024A DE1110609B (en) | 1959-12-08 | 1959-12-08 | Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates |
| CH1364660A CH369111A (en) | 1959-12-08 | 1960-12-06 | Process for dyeing and printing textile structures made of linear aromatic polyesters, in particular polyethylene terephthalates |
| BE597951A BE597951A (en) | 1959-12-08 | 1960-12-08 | Dyeing and printing of polyester articles. |
| GB4235460A GB961446A (en) | 1959-12-08 | 1960-12-08 | Process for dyeing or printing shaped structures of linear aromatic polyesters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30024A DE1110609B (en) | 1959-12-08 | 1959-12-08 | Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1110609B true DE1110609B (en) | 1961-07-13 |
Family
ID=7093567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30024A Pending DE1110609B (en) | 1959-12-08 | 1959-12-08 | Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE597951A (en) |
| CH (1) | CH369111A (en) |
| DE (1) | DE1110609B (en) |
| GB (1) | GB961446A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH619584GA3 (en) | 1975-03-26 | 1980-10-15 |
-
1959
- 1959-12-08 DE DEF30024A patent/DE1110609B/en active Pending
-
1960
- 1960-12-06 CH CH1364660A patent/CH369111A/en unknown
- 1960-12-08 BE BE597951A patent/BE597951A/en unknown
- 1960-12-08 GB GB4235460A patent/GB961446A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH1364660A4 (en) | 1963-01-31 |
| GB961446A (en) | 1964-06-24 |
| CH369111A (en) | 1963-06-29 |
| BE597951A (en) | 1961-06-08 |
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