DE2756331A1 - AZO DYES - Google Patents
AZO DYESInfo
- Publication number
- DE2756331A1 DE2756331A1 DE19772756331 DE2756331A DE2756331A1 DE 2756331 A1 DE2756331 A1 DE 2756331A1 DE 19772756331 DE19772756331 DE 19772756331 DE 2756331 A DE2756331 A DE 2756331A DE 2756331 A1 DE2756331 A1 DE 2756331A1
- Authority
- DE
- Germany
- Prior art keywords
- printing
- dyes
- transfer printing
- printed
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 claims description 16
- 238000007639 printing Methods 0.000 claims description 13
- 238000010023 transfer printing Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000000987 azo dye Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000000976 ink Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000002657 fibrous material Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- VFZOPOZDIBQSJG-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzonitrile Chemical compound NC1=CC(Cl)=C(C#N)C=C1Cl VFZOPOZDIBQSJG-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- -1 Dichloro-4-cyananiline Chemical compound 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HHSPVTKDOHQBKF-UHFFFAOYSA-J calcium;magnesium;dicarbonate Chemical compound [Mg+2].[Ca+2].[O-]C([O-])=O.[O-]C([O-])=O HHSPVTKDOHQBKF-UHFFFAOYSA-J 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
Description
AzofarbstoffeAzo dyes
5090 Leverkusen, Bayerwprk K/bC5090 Leverkusen, Bayerwprk K / bC
16.Uez.W716.Uec.W7
-N S ·-N S
(D(D
Gegenstand der Erfindung sind Azofarbstoffe der FormelThe invention relates to azo dyes of the formula
/—<C1
NC-// \^~N=N- / - < C1
NC - // \ ^ ~ N = N-
Cl
worinCl
wherein
R H, CH3, C2H5, Cl, Br oder CF3; R1 C1-C„-Alkyl undRH, CH 3 , C 2 H 5 , Cl, Br or CF 3 ; R 1 C 1 -C "-alkyl and
R2 H, C1-C4-AIkYl, C2H4Cl, C2H4Br, C3H4F oder C2H4OCH3 bedeuten sowie deren Verwendung zum Bedrucken von flächenförmigen Gebilden aus synthetischen oder teilsynthetischen polymeren Materialien nach dem Transferdruckprinzip.R 2 H, C 1 -C 4 -AlkYl, C 2 H 4 Cl, C 2 H 4 Br, C 3 H 4 F or C 2 H 4 OCH 3 and their use for printing flat structures made of synthetic or partially synthetic polymers Materials based on the transfer printing principle.
Bevorzugte Farbstoffe sind solche der Formel (I), worin R H, CH3 oder ClPreferred dyes are those of the formula (I) in which RH, CH 3 or Cl
R1 C2Hc undR 1 C 2 Hc and
R2 C2H5 oder C2H4ClR 2 C 2 H 5 or C 2 H 4 Cl
bedeuten.mean.
Die neuen Farbstoffe erhält man nach an sich bekannten Methoden, vorzugsweise durch Umsetzung von diazotierten» 2,5-The new dyes are obtained by methods known per se, preferably by reacting diazotized »2.5-
Le A 18 632Le A 18 632
909825/0364909825/0364
-I»-I »
Dichlor-4-cyananilin mit entsprechenden Kupplungskomponenten, wie z.B. in der DE-OS 25 000 71 beschrieben.Dichloro-4-cyananiline with corresponding coupling components, as described, for example, in DE-OS 25 000 71.
Ein weiterer Gegenstand der Erfindung sind Drucktinten bzw. Druckpasten für den Transferdruck, die mit derartigen Farbstoffen bedruckten bzw. imprägnierten Hilfsträger und die Substrate, die mit derartigen Farbstoffen nach dem Transferdruckprinzip gefärbt worden sind.The invention also relates to printing inks or printing pastes for transfer printing which contain such dyes printed or impregnated auxiliary carrier and the substrates with such dyes according to the transfer printing principle have been colored.
Das Transferdruckverfahren ist allgemein bekannt (vgl. z.B. Colour Index, 3. Ausgabe, Bd. 2, Seite 2480) und beispielsweise detailliert in den französischen Patentschriften 1 223 330, 1 334 829 und 1 585 119) beschrieben.The transfer printing process is generally known (see e.g. Color Index, 3rd edition, Vol. 2, page 2480) and, for example described in detail in French patents 1,223,330, 1,334,829 and 1,585,119).
Besonders geeignete Druckverfahren zur Herstellung von bedruckten Papierhilfsträgern sind der Tiefdruck und der Rotationsfilmdruck. Particularly suitable printing processes for the production of printed auxiliary paper carriers are gravure printing and rotary film printing.
Geeignete flächenförmige Gebilde sind Vliese, Filze, Pelze, Folien und vor allem Gewebe aus synthetischen Polyamiden und vor allem aus aromatischen Polyestern und Cellulosetriacetat sowie deren Mischungen mit Baumwolle.Suitable sheet-like structures are fleeces, felts, furs, Films and especially fabrics made from synthetic polyamides and especially from aromatic polyesters and cellulose triacetate and their blends with cotton.
Bei den letztgenannten teilsynthetischen Fasermaterialien sowie bei Fasermaterialien aus reinen Cellulosefaser^, wie etwa Baumwolle, empfiehlt es sich, das Substrat vor dem eigentlichen Transferdruck mit einer die Faser hydrophobierenden reaktionsfähigen Substanz, beispielsweise mit Reaktantharzen, und/oder Faserquellmitteln zu behandeln (vgl. DE-OS 24 18 519, 24 17 774, 24 24 949, 24 36 783, 24 53 362, 24 58 660, 25 02 590, 26 16 993)With the last-mentioned partially synthetic fiber materials and with fiber materials made of pure cellulose fiber ^, such as For example cotton, it is recommended that the substrate be coated with a hydrophobizing agent for the fiber before the actual transfer printing reactive substance, for example with reactant resins, and / or fiber swelling agents (cf. DE-OS 24 18 519, 24 17 774, 24 24 949, 24 36 783, 24 53 362, 24 58 660, 25 02 590, 26 16 993)
Nach dem beanspruchten Verfahren erhält man auf den genannten Substraten farbstarke Drucke mit guten Gebrauchsechtheiten.The claimed process gives prints of strong color and good fastness properties on the substrates mentioned.
Le A 18 632 - 2 -Le A 18 632 - 2 -
909825/0364909825/0364
A) 75 g des Farbstoffs der FormelA) 75 g of the dye of the formula
3
50 g eines anionischen Dispergiermittels, z.B. eines Ligninsulfonates oder eines Kondensationsproduktes aus Naphthalinsulf
onsäure und Formaldehyd, und 100 ml Wasser werden vermischt und in einer Kugelmühle durch 10-stündiges
Mahlen in eine fein verteilte Form übergeführt.3
50 g of an anionic dispersant, for example a lignin sulfonate or a condensation product of naphthalenesulfonic acid and formaldehyde, and 100 ml of water are mixed and converted into a finely divided form by grinding for 10 hours in a ball mill.
Die so erhaltene, ca. 30 %ige Rohfarbe enthaltende Dispersion ist lagerstabil.The dispersion thus obtained, containing about 30% raw paint, is storage-stable.
B) Die nach A) erhaltene wäßrige Dispersion kann wie folgt zu einer Druckpaste verarbeitet werden.B) The aqueous dispersion obtained according to A) can be processed into a printing paste as follows.
50 bis 200 g werden mit 400 g einer 10 %igen Johannisbrotkernmehl ätherverd ickung und 550 bis 400 ml Wasser angeteigt. 50 to 200 g are mixed with 400 g of a 10% carob gum ether thickening and make a paste with 550 to 400 ml of water.
C) Mit dieser Druckpaste wird ein Papier im Tiefdruckverfahren bedruckt. Verpreßt man dieses Papier währendC) This printing paste is used to print a paper using the gravure printing process. If you press this paper during
15 bis 60 Sekunden bei 200°C mit einem Textil aus Polyesterfasern, so erhält man einen klaren roten Druck.15 to 60 seconds at 200 ° C. with a textile made of polyester fibers, a clear red color is obtained Pressure.
A) 50 g des Farbstoffs der Formel
.ClA) 50 g of the dye of the formula
.Cl
Cl
Le A 18 632 - 3 -Cl
Le A 18 632 - 3 -
909825/036A909825 / 036A
werden mit 5 bis 10 g eines Emulgatorgemisches aus äthoxyliertem Nonylphenol (4 bis 12 Mol Äthylenoxid) in Wasser angeteigt. Man setzt 10 g Äthylcellulose N 4 (Hercules Powder) und 30 bis 40 Teile eines Maleinatharzes zu, das durch Kondensation von Colophonium mit Maleinsäure hergestellt wurde. Man knetet bei 80 bis 100°C ca. 2 Stunden und mahlt anschließend auf einer der üblichen Mühlen. Man erhält ein feinkörniges Farbstoffpulver.are with 5 to 10 g of an emulsifier mixture of ethoxylated nonylphenol (4 to 12 moles of ethylene oxide) in water made into a paste. 10 g of ethyl cellulose N 4 (Hercules Powder) and 30 to 40 parts of a maleinate resin are added by condensation of rosin with maleic acid. It is kneaded at 80 to 100 ° C for about 2 hours and then grinds on one of the usual mills. A fine-grained dye powder is obtained.
B) 200 g des nach A) erhaltenen Farbstoffpulvers gibt man unter Rühren in ein Gemisch ausB) 200 g of the dye powder obtained according to A) are added with stirring into a mixture
730 g Äthanol
50 g Äthylenglykol und
20 g Äthylcellulose N 22 (Hercules Powder).730 g of ethanol
50 g ethylene glycol and
20 g ethyl cellulose N 22 (Hercules Powder).
C) Mit der so erhaltenen Druckfarbe kann man im Tiefdruck
Papiere bedrucken. Von diesen bedruckten Papieren kann man im Transfer-Verfahren Textilien aus Cellulosetriacetat,
z.B. Gewirke, bedrucken und erhält ebenfalls
klare, rote Drucke.C) The printing ink thus obtained can be used for gravure printing on papers. Textiles made of cellulose triacetate, for example knitted fabrics, can be printed from these printed papers in the transfer process and are also obtained
clear, red prints.
g des Farbstoffs der Formelg of the dye of the formula
ClCl
werden zusammen mit 50 g eines Kondensationsproduktes aus Naphthalinsulfonsäure und Formaldehyd und 100 g Wasser in einer Kugelmühle fein dispergiert. Die so erhaltene Farb-are together with 50 g of a condensation product of naphthalenesulfonic acid and formaldehyde and 100 g of water in finely dispersed in a ball mill. The resulting color
Le A 18 632 - 4 -Le A 18 632 - 4 -
909825/0364909825/0364
Stoffdispersion rührt man in eine Verdickung ein, die ausSubstance dispersion is stirred into a thickening that results from
21 Teilen Wasser21 parts of water
7 Teilen Diacetonalkohol7 parts of diacetone alcohol
41,3 Teilen Microdol x ' extra (natürliches Calcium-Magnesium-Carbonat) 41.3 parts Microdol x ' extra (natural calcium-magnesium-carbonate)
0,2 Teilen Natriumhexamethaphosphat0.2 part sodium hexamethaphosphate
0,5 Teilen Naphthalinsulfonsäure/Formaldehyd-Kondensationsprodukt 0.5 part of naphthalenesulfonic acid / formaldehyde condensation product
8 Teilen Bentone (R) EW 3 %ig (Quellton)8 parts Bentone (R) EW 3% (swelling clay)
12 Teilen Acrylatbinder DA (50 %ige Lösung des Ammonium-Salzes
eines Polyacrylates in 33 %igem wäßrigem Äthylalkohol. Das Polyacrylat ist ein Copolymerisat aus
60 Acrylsäureäthylester
25 Methacrylsäureäthylester
15 Acrylsäure).12 parts of acrylate binder DA (50% solution of the ammonium salt of a polyacrylate in 33% aqueous ethyl alcohol. The polyacrylate is a copolymer of 60 acrylic acid ethyl esters
25 ethyl methacrylate
15 acrylic acid).
Diese Druckpaste druckt man mit Siebdruckschablonen oder mit Rundschablonen auf einen Zwischenträger, vorzugsweiseThis printing paste is printed with screen printing stencils or with round stencils on an intermediate carrier, preferably
2 Papier mit einem Quadratmetergewicht von ca. 60 bis 80 g/cm und einem Cobbgo-Wert von etwa 80. Man erhält einen glatten Druck.2 Paper with a weight per square meter of approx. 60 to 80 g / cm and a Cobb go value of approx. 80. A smooth print is obtained.
Mit dem so hergestellten Papier kann man Textilien aus Polyester/Baumwolle in der Weise bedrucken, daß man das Textil mit dem Papier während 15 bis 60 Sekunden in Kontakt bringt und auf Temperaturen von 190 bis 2000C erhitzt.With the thus prepared paper can textiles made of polyester / cotton in the manner of printing, by bringing the fabric with the paper for 15 to 60 seconds in contact and heated to temperatures from 190 to 200 0 C.
Man erhält einen kräftigen roten Umdruck mit guten Gebrauchsechtheiten. Ähnliche Ergebnisse erzielt man, wenn man solche Farbstoffe der Formel (I) einsetzt, die durch die in nachstehender Tabelle aufgeführten Komponenten durch Diazotieren und Kuppeln erhältlich sind:A strong red transfer print with good fastness properties is obtained. You get similar results if you have such Dyes of the formula (I) are used, which are identified by the in the following The components listed in the table can be obtained by diazotizing and coupling:
Le A 18 632 - 5 -Le A 18 632 - 5 -
909825/0364909825/0364
DiazokomponenteDiazo component
KupplungskomponenteCoupling component
ClCl
NC~\J/~NH NC ~ \ J / ~ NH
ClCl
1010
1212th
1414th
CH-CH-
C)-N(C3H7)C) -N (C 3 H 7 )
CHCH
NHiC3H7 NHiC 3 H 7
CH3 CH 3
^-NUC4H9)^ -NUC 4 H 9 )
Le Ά 18Le Ά 18
909825/0364909825/0364
Tabelle (Fortsetzung) Table (continued)
DiazokomponenteDiazo component
,Cl 1 5 NC-^ xVnH., Cl 1 5 NC- ^ x VnH.
KupplungskomponenteCoupling component
C4H5 C 4 H 5
1616
CH-CH-
C3H7 C 3 H 7
CH.CH.
17 18 19 20 2117 18 19 20 21
C2H5 C 2 H 5
ClCl
Λ-Ν (C2H5) 2 Λ-Ν (C 2 H 5 ) 2
CF,CF,
BrBr
C2H5 C2H4ClC 2 H 5 C 2 H 4 Cl
2222nd
C2H5 C2H4FC 2 H 5 C 2 H 4 F
2323
CHCH
Le A 18 Le A 18
909825/0364909825/0364
Tabelle (Fortsetzung) Diazokomponente Table (continued) Diazo component
λθ-λθ-
KupplungskomponenteCoupling component
Cl 24 NC-/7 N>-NH.Cl 24 NC- / 7 N > -NH.
C2H5 C2H4BrC 2 H 5 C 2 H 4 Br
2525th
2727
CH-CH-
C2H5 C 2 H 5
CH.CH.
.C2H5 C2H4F.C 2 H 5 C 2 H 4 F
Le A 18Le A 18
909825/0 364909825/0 364
Der in Beispiel 1 verwendete Farbstoff wurde wie folgt hergestellt:The dye used in Example 1 was prepared as follows:
187 g 2,5-Dichlor-4-cyananilin werden unter Rühren und Kühlung auf O0C in 1000 g konz. Schwefelsäure eingetragen. Es wird 1 Stunde nachgerührt. Dann werden bei 0 bis 3°C unter gutem Rühren innerhalb von 1 Stunde 315 g Nitrosylschwefelsäure eingetropft. Es wird 1 Stunde nachgerührt und dann auf 30OO g Eis gegossen, wobei kräftig gerührt wird, überschüssige Salpetrige Säure wird durch etwas Amidosulfonsäure zerstört. Zu der so hergestellten Diazoniumsalzlösung gibt man die Lösung von 163 g 3-N,N-Diäthylaminotoluol in einer Mischung aus 300 ml konz. Salzsäure und 3000 ml Wasser. Die sofort einsetztende Kupplung wird durch Zutropfen von konz. NaOH bis zu einem pH-Wert von 5 vervollständigt. Durch Zugabe von Eis wird dabei die Temperatur unter 10°C gehalten. Nach beendeter Kupplung wird der Farbstoff auf einer Nutsche abfiltriert und wiederholt mit Wasser gewaschen. Man erhält nach dem Trocknen 343 g eines roten Pulvers. 187 g of 2,5-dichloro-4-cyananiline are concentrated in 1000 g with stirring and cooling to 0 ° C. Sulfuric acid entered. It is stirred for 1 hour. 315 g of nitrosylsulfuric acid are then added dropwise at 0 to 3 ° C. with thorough stirring over the course of 1 hour. The mixture is stirred for 1 hour and then poured onto 300 g of ice, stirring vigorously, excess nitrous acid is destroyed by a little sulfamic acid. The solution of 163 g of 3-N, N-diethylaminotoluene in a mixture of 300 ml of conc. Hydrochloric acid and 3000 ml of water. The immediately onset of coupling is achieved by the dropwise addition of conc. NaOH completed to pH 5. The temperature is kept below 10 ° C. by adding ice. After the coupling has ended, the dye is filtered off on a suction filter and washed repeatedly with water. After drying, 343 g of a red powder are obtained.
Le A 18 632 - 9 -Le A 18 632 - 9 -
909825/0364909825/0364
Claims (7)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772756331 DE2756331A1 (en) | 1977-12-17 | 1977-12-17 | AZO DYES |
| GB7848256A GB2010304B (en) | 1977-12-17 | 1978-12-13 | Azo dyestuffs |
| ES476047A ES476047A1 (en) | 1977-12-17 | 1978-12-15 | Azo dyestuffs |
| BR7808430A BR7808430A (en) | 1977-12-17 | 1978-12-15 | AZOIC DYES, PROCESS FOR PRINTING PLANT STRUCTURES, AUXILIARY VEHICLES, INKS AND PRINTING AND POLYESTER FIBER MATERIALS |
| JP15429178A JPS5490336A (en) | 1977-12-17 | 1978-12-15 | Azo dye |
| IT7830898A IT7830898A0 (en) | 1977-12-17 | 1978-12-15 | AZO DYES. |
| FR7835368A FR2411864A1 (en) | 1977-12-17 | 1978-12-15 | NITROGEN COLORANTS AND THEIR APPLICATION IN TRANSFER PRINTING |
| BE192338A BE872789A (en) | 1977-12-17 | 1978-12-15 | NITROGEN COLORANTS AND THEIR APPLICATION IN TRANSFER PRINTING |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772756331 DE2756331A1 (en) | 1977-12-17 | 1977-12-17 | AZO DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2756331A1 true DE2756331A1 (en) | 1979-06-21 |
Family
ID=6026404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772756331 Pending DE2756331A1 (en) | 1977-12-17 | 1977-12-17 | AZO DYES |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5490336A (en) |
| BE (1) | BE872789A (en) |
| BR (1) | BR7808430A (en) |
| DE (1) | DE2756331A1 (en) |
| ES (1) | ES476047A1 (en) |
| FR (1) | FR2411864A1 (en) |
| GB (1) | GB2010304B (en) |
| IT (1) | IT7830898A0 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384225A1 (en) * | 1989-02-23 | 1990-08-29 | CASSELLA Aktiengesellschaft | Use of dyestuffs in the sublimation-transfer process |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3841505A1 (en) * | 1988-12-09 | 1990-06-13 | Cassella Ag | WATER-INSOLUBLE MONOAZO DYES, MIXTURES OF THESE MONOAZO DYES, THEIR PRODUCTION AND USE |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2500071A1 (en) * | 1975-01-02 | 1976-07-08 | Basf Ag | AZO DYES FOR TRANSFER PRINTING |
-
1977
- 1977-12-17 DE DE19772756331 patent/DE2756331A1/en active Pending
-
1978
- 1978-12-13 GB GB7848256A patent/GB2010304B/en not_active Expired
- 1978-12-15 BR BR7808430A patent/BR7808430A/en unknown
- 1978-12-15 IT IT7830898A patent/IT7830898A0/en unknown
- 1978-12-15 JP JP15429178A patent/JPS5490336A/en active Pending
- 1978-12-15 ES ES476047A patent/ES476047A1/en not_active Expired
- 1978-12-15 FR FR7835368A patent/FR2411864A1/en not_active Withdrawn
- 1978-12-15 BE BE192338A patent/BE872789A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384225A1 (en) * | 1989-02-23 | 1990-08-29 | CASSELLA Aktiengesellschaft | Use of dyestuffs in the sublimation-transfer process |
| US5093307A (en) * | 1989-02-23 | 1992-03-03 | Cassella Aktiengesellschaft | Use of water-insoluble monoazo dyes of the formula i |
Also Published As
| Publication number | Publication date |
|---|---|
| ES476047A1 (en) | 1979-10-16 |
| GB2010304A (en) | 1979-06-27 |
| IT7830898A0 (en) | 1978-12-15 |
| JPS5490336A (en) | 1979-07-18 |
| BR7808430A (en) | 1979-08-21 |
| BE872789A (en) | 1979-06-15 |
| GB2010304B (en) | 1982-04-07 |
| FR2411864A1 (en) | 1979-07-13 |
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| OD | Request for examination | ||
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