USRE22133E - Azo dyes - Google Patents
Azo dyes Download PDFInfo
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- USRE22133E USRE22133E US22133DE USRE22133E US RE22133 E USRE22133 E US RE22133E US 22133D E US22133D E US 22133DE US RE22133 E USRE22133 E US RE22133E
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- 239000000987 azo dye Substances 0.000 title description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 28
- 238000005859 coupling reaction Methods 0.000 description 20
- 230000001808 coupling Effects 0.000 description 19
- 238000010168 coupling process Methods 0.000 description 19
- -1 diazo imino compound Chemical class 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000004043 dyeing Methods 0.000 description 16
- 239000002562 thickening agent Substances 0.000 description 16
- 229920000742 Cotton Polymers 0.000 description 15
- 229920000297 Rayon Polymers 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002964 rayon Substances 0.000 description 14
- WXWCDTXEKCVRRO-UHFFFAOYSA-N Para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 150000003931 anilides Chemical class 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003086 colorant Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N Meglumine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 230000003381 solubilizing Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- YJISHJVIRFPGGN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 YJISHJVIRFPGGN-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229940116362 Tragacanth Drugs 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 229940100445 WHEAT STARCH Drugs 0.000 description 2
- 230000000397 acetylating Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 1
- JSCNDCWUFHAJQL-UHFFFAOYSA-N 2-hydroxy-9H-carbazole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(O)C(C(=O)O)=C2 JSCNDCWUFHAJQL-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- LCZDCKMQSBGXAH-AWEZNQCLSA-N 3-[[3-[(2S)-2-amino-2-carboxyethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl]-5-phenylthiophene-2-carboxylic acid Chemical compound O=C1C(C)=CN(C[C@H](N)C(O)=O)C(=O)N1CC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 LCZDCKMQSBGXAH-AWEZNQCLSA-N 0.000 description 1
- PHQKCVOZVPSTAF-UHFFFAOYSA-N 3-hydroxyanthracene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C=C(C(C(=O)O)=C3)O)C3=CC2=C1 PHQKCVOZVPSTAF-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- CYFSLNORDOJCNJ-UHFFFAOYSA-N N-chloro-4-ethoxyaniline Chemical compound CCOC1=CC=C(NCl)C=C1 CYFSLNORDOJCNJ-UHFFFAOYSA-N 0.000 description 1
- 210000004940 Nucleus Anatomy 0.000 description 1
- 229940043230 Sarcosine Drugs 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 229960003080 Taurine Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N Taurine Natural products NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine zwitterion Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 230000000087 stabilizing Effects 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
Definitions
- a coupling component commonly used was 2:3- hydroxy-naphthoic acid.
- cresidines are readily available aryl amines, combinations of anilides of 2:3-hydroxy-naphthoic acid with these amines, havin sufficient merit for commercial purposes, have not been found, in so far as I am aware. It has now been discovered that diazotized cresidine can be stabilized and used to make colored compounds and dyeings of commercial merit by the ice color processes and particularly for the dyeing of cellulosic fibres, such as cotton and regenerated cellulose.
- other object of the invention is to provide compositions for dyeing which contain an azo dye coupling component and diazotized cresidine which is stabilized against coupling until developing agents are applied.
- Another object of the invention is to provide fabrics dyed with the composition.
- Another object of the invention is to provide processes for making said compounds and dyeings. Still other objects of the invention will be apparent from the following more detailed description.
- the objects of the invention may be attained in general by diazotizing cresidine and combining the diazotized cresidine with a stabilizing compound which will stabilize the diazo compound against coupling in alkaline medium but will permit the coupling reaction in acidic media, such as water soluble diazoimino compounds or antidiazotates which can be prepared by methods well known in the art. impregnated with these alkaline compositions and the dye is developed by hydrolysis of the sta bilized diazo as by treatment with acid whereupon the color is developed.
- a stabilizing compound which will stabilize the diazo compound against coupling in alkaline medium but will permit the coupling reaction in acidic media, such as water soluble diazoimino compounds or antidiazotates which can be prepared by methods well known in the art. impregnated with these alkaline compositions and the dye is developed by hydrolysis of the sta bilized diazo as by treatment with acid whereupon the color is developed.
- Example 1 A printing paste was prepared by mixing 2 parts of the diazo imino compound represented by the formula *OClls which was obtained by the action of diazotized cresidine on methyl glucamine, 2 parts of the 2:5-dimethyl-4-chlor-anilide of 2:3-hydroxynaphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of a thickener.
- the diazo imino compound represented by the formula *OClls which was obtained by the action of diazotized cresidine on methyl glucamine
- 2 parts of the 2:5-dimethyl-4-chlor-anilide of 2:3-hydroxynaphthoic acid 4 parts of the mono ethyl ether of ethylene glycol
- 24 parts of water 24 parts of water
- 3 parts of sodium hydroxide solution (30%) 65 parts of a thickener.
- the thickener was made by mixing 60 parts of wheat starch, 580 parts of water and 360 parts of tragacanth 6% solution.
- Example 2 A printing paste was prepared by mixing 2.3 parts of the diazo imino compound mentioned in Example 1, 1.7 parts of the aceto acct-3 chlor-4 ethoxy-aniline, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of sodium hydroxide solution (30%) and 65 parts of the thickener mentioned in Example 1.
- Example 3 A printing paste was prepared by mixing 1.9 parts of the diazo imino compound mentioned in Example 1, 2.1 parts of the 2:4-dimethyl-5-nitroanilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts sodium hydroxide solution (30%) and 65 parts of the thickener mentioned in Example 1.
- N N CH
- Example 4 A printing paste was prepared by mixing 2.2 parts of the diazo imino compound mentioned in Example 1, 1.8 parts of the anilide of 2:3-hydroxy-naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts water, 3 parts sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
- a printing paste was prepared by mixing 2.2 parts of the diazo imino compound mentioned in Example 1, 1.8 parts of the Z-methyl anilide of 2:3-hydroxy-naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of Water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener mentioned in Example 1.
- Example 7 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the 4-chlor-anilide of 2:3-hydroxy-naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
- Example 8 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the 2:4-dimethyl anilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of Water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
- Example 9 obtained of good general fastness properties.
- the new color had the following probable formula:
- Example A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the 2:5-dimethyl-anilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution and 65 parts of thickener as mentioned in Example 1.
- Example 11 A printing paste was prepared by mixing 2.4 parts of the diazo imino compound mentioned in Example 1, 1.6 parts of the aceto acet para phenetidine, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30 and 65 parts of thickener as mentioned in Example 1.
- a printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the coupling component obtained by diazotizing 5-nitro-2-amino-anisole and coupling in acid solution with l-amino-7- naphthol, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and parts of thickener as mentioned in Example 1.
- Example 13 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the coupling component obtained by diazotizing meta-nitro aniline and coupling with lz'l-amino naphthol and acetylating the product, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
- Example 14 A printing paste was prepared by mixing 2 parts of the diazo imino compound mentioned in Example 1, 2 parts of the coupling component obtained by diazotizing 5-nitro-2-amino anisole and coupling with lz'l-amino naphthol and acetylating the product, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of Water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
- Example 1 5 A printing paste was prepared by mixing 1.8 parts of the diazo imino compound of the following formula:
- Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A Bordeaux dyeing was obtained of good general fastness properties.
- Example 16 A printing paste was prepared by mixing 2 parts of the diazo imino compound of the formula:
- the thickener was made by mixing parts of wheat starch, 580 parts of water and 360 parts of tragacanth 6% solution.
- Cotton and rayon piece goods were printed on an engraved roller with the above printing paste.
- the printed fabric was dried in the air and then subjected to the action of live steam containing the vapors of acetic acid. A color development took place.
- the printed goods were rinsed with water, boiled for 5 minutes in a 0.5% soap solution, again rinsed and dried. A deep Bordeaux dyeing of better fastness properties and brighter in shade than the products of the preceding examples was obtained.
- the new color is represented by the formula:
- a very large number of other coupling components which are free from solubilizing groups can be used.
- the most suitable type of coupling components are the aryl-amides of ortho-hydroxy-aryl-amides, of carboxylic acids and of beta-keto-carboxylic acids.
- the colors may be applied by any of the processes for the application of ice colors. These are well known in the art but they find their most important use in printing according to which alkaline compositions containing the stabilized diazo component and the coupling components is printed on the fibre and developed by hydrolysis of the diazo imino compounds.
- the fibres are padded with the arylamide and then immersed in a solution of diazotized aryl amine.
- the fibres are impregnated with the arylamide and printed with pastes containing the diazotized aryl amine.
- the diazotized aryl amine is converted to its antidiazotate (nitrosamine) and the fibres are printed with pastes containing the antidiazotate and the arylamide.
- the color is then developed by treatment with a mild acid, desirably at an elevated temperature.
- the diazotized aryl amine is reacted with one of various aliphatic, isocyclicl or heterocyclic amines which desirably contains a water solubilizing group and a diazo imino derivative is formed.
- the fibre to be dyed is printed with a paste containing the diazo imino derivative and the arylamide.
- the color is then developed by hydrolyzing the diazo imino compound, such as by acting upon the printed goods with an acid, whereupon the coupling is immediately effected.
- the desirable stabilizing agents are, methyl glucamine, diethanolamine, sarcosine, ethyl taurine, proline and 4-sulfo-2-amino-benzoic acid.
- the rate of color development will vary among the different derivatives of the stabilizing agents but for a given stabilizing agent, it has been found that the rapidity of development of the diazo imino compounds is rapid.
- the preferred dyes are those made by coupling diazotized cresidine and the anilides of 2:3-hydroxy naphthoic acid.
- the anilide nucleus may be unsubstituted or it may be substituted by alkyl, alkoxy, halogen or nitro such as chloro, bromo, methyl, ethyl, propyl, butyl and the corresponding alkoxy groups.
- the anilides of 2:3-hydroxy-naphthoic acids in which the benzene ring of the anilide is substituted by two alkyl groups and a nitro or ohloro group or by three methyl groups in the 2:4:5-positions with respect to the amino group are preferred.
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Description
Reissued July 14, 1942 UNITED STATES PATENT OFFICE AZO DYES Frithjof Zwilgmcyer, Wilmington, DeL, assignor to E. I. du Pont de Nemours & Company, Wilmington, Del, a corporation of Delaware No Drawing. Original No. 2,167,142, dated July 25, 1939, Serial No. 151,966, July 3, 1937.
plication for reissue April 11, 1942, Serial No.
5 Claims.
aryl amines with azo dye coupling components.
A coupling component commonly used was 2:3- hydroxy-naphthoic acid. Although the cresidines are readily available aryl amines, combinations of anilides of 2:3-hydroxy-naphthoic acid with these amines, havin sufficient merit for commercial purposes, have not been found, in so far as I am aware. It has now been discovered that diazotized cresidine can be stabilized and used to make colored compounds and dyeings of commercial merit by the ice color processes and particularly for the dyeing of cellulosic fibres, such as cotton and regenerated cellulose.
It is an object of this invention to provide azo compounds which are obtained by coupling azo dye coupling components which are free from solubilizing groups to diazotized cresidine. other object of the invention is to provide compositions for dyeing which contain an azo dye coupling component and diazotized cresidine which is stabilized against coupling until developing agents are applied. Another object of the invention is to provide fabrics dyed with the composition. Another object of the invention is to provide processes for making said compounds and dyeings. Still other objects of the invention will be apparent from the following more detailed description.
The objects of the invention may be attained in general by diazotizing cresidine and combining the diazotized cresidine with a stabilizing compound which will stabilize the diazo compound against coupling in alkaline medium but will permit the coupling reaction in acidic media, such as water soluble diazoimino compounds or antidiazotates which can be prepared by methods well known in the art. impregnated with these alkaline compositions and the dye is developed by hydrolysis of the sta bilized diazo as by treatment with acid whereupon the color is developed.
In the following more detailed description ref- The material to be dyed is erence will be made to the examples which illustrate the invention but the invention i not limited thereto. In the examples the quantities are given in parts by weight unless otherwise specifled.
Example 1 A printing paste was prepared by mixing 2 parts of the diazo imino compound represented by the formula *OClls which was obtained by the action of diazotized cresidine on methyl glucamine, 2 parts of the 2:5-dimethyl-4-chlor-anilide of 2:3-hydroxynaphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of a thickener.
The thickener was made by mixing 60 parts of wheat starch, 580 parts of water and 360 parts of tragacanth 6% solution.
Cotton and rayon piece goods were printed on an engraved roller with the above printing paste. The printed fabric was dried in the air and then subjected to the action of live steam containing the vapors of acetic acid. A color development took place. The printed goods were rinsed with water, boiled for 5 minutes in a 0.5% soap solution, again rinsed and dried. A deep Bordeaux dyeing of good fastness properties was obtained. The new color is represented by the formula Example 2 A printing paste was prepared by mixing 2.3 parts of the diazo imino compound mentioned in Example 1, 1.7 parts of the aceto acct-3 chlor-4 ethoxy-aniline, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of sodium hydroxide solution (30%) and 65 parts of the thickener mentioned in Example 1.
Cotton or rayon piece goods were printed with the above composition and developed as described in Example 1. A bright yellow dyeing was obtained of good general fastness properties. The new color had the following probable formula:
CH5 OCH:
CO Cl N:NCH
C ONE Calls Example 3 A printing paste was prepared by mixing 1.9 parts of the diazo imino compound mentioned in Example 1, 2.1 parts of the 2:4-dimethyl-5-nitroanilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts sodium hydroxide solution (30%) and 65 parts of the thickener mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A Bordeaux dyeing was obtained of good general fastness properties. The new color had the following probable formula:
N=N CH;
0 OH ONH CH3 CH3 N02 Example 4 A printing paste was prepared by mixing 2.2 parts of the diazo imino compound mentioned in Example 1, 1.8 parts of the anilide of 2:3-hydroxy-naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts water, 3 parts sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A bluish red dyeing was obtained of good general fastness properties. The new color had the following probable formula:
on o ONE-O Example 5 A printing paste was prepared by mixing 2.2 parts of the diazo imino compound mentioned in Example 1, 1.8 parts of the Z-methyl anilide of 2:3-hydroxy-naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of Water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A bluish red dyeing was obtained of good general fastness properties. The new color had the following probable formula:
OCIIa on CONIIC Example 6 OH coma-O Example 7 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the 4-chlor-anilide of 2:3-hydroxy-naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A bluish red dyeing was obtained of good general fastness properties. The new color had the following probable formula:
OCHa
Example 8 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the 2:4-dimethyl anilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of Water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A bluish red dyeing was obtained of good general fastness properties. The new color had the following probable formula:
OH CONE CH;
Example 9 obtained of good general fastness properties.
The new color had the following probable formula:
OH CONHQCB3 Example A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the 2:5-dimethyl-anilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution and 65 parts of thickener as mentioned in Example 1.
Cotton or rayon piece goods were printed with the above composition and developed and described in Example 1. obtained of good general fastness properties. The new color had the following probable formula:
CKCH;
Example 11 A printing paste was prepared by mixing 2.4 parts of the diazo imino compound mentioned in Example 1, 1.6 parts of the aceto acet para phenetidine, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30 and 65 parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1.
A bluish red dyeing was A yellow dyeing was ob- OCHa Example 12 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the coupling component obtained by diazotizing 5-nitro-2-amino-anisole and coupling in acid solution with l-amino-7- naphthol, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A black dyeing was obtained of good general fastness properties. The new color had the following probable formula:
0 on; on
CH3 N N 0 mn- N=NC NO1 Example 13 A printing paste was prepared by mixing 2.1 parts of the diazo imino compound mentioned in Example 1, 1.9 parts of the coupling component obtained by diazotizing meta-nitro aniline and coupling with lz'l-amino naphthol and acetylating the product, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A brown dyeing was obtained of good general fastness properties. The new color had the following probable formula:
0 0 H3 on (:0 CH3 I N02 Example 14 A printing paste was prepared by mixing 2 parts of the diazo imino compound mentioned in Example 1, 2 parts of the coupling component obtained by diazotizing 5-nitro-2-amino anisole and coupling with lz'l-amino naphthol and acetylating the product, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of Water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A dark brown dyeing was obtained of good general fastness properties. The new color had the following probable formula:
0 Ha (I) H N=N (I) 0 Ha C 0 0 HI I Example 1 5 A printing paste was prepared by mixing 1.8 parts of the diazo imino compound of the following formula:
Cll;
which was obtained by the action of diazotized cresidine on diethanol amine, 2.2 parts of m-nitro anilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solu tion and 65 parts of a thickener as mentioned in Example 1.
Cotton and rayon piece goods were printed with the above composition and developed as described in Example 1. A Bordeaux dyeing was obtained of good general fastness properties.
The now color had the following probable p formula:
Example 16 A printing paste was prepared by mixing 2 parts of the diazo imino compound of the formula:
OCHi
which was obtained by the action of diazotized cresidine on methyl glucamine, 2 parts of the 2:4:5-trimethyl-anilide of 2:3-hydroxy naphthoic acid, 4 parts of the mono ethyl ether of ethylene glycol, 24 parts of water, 3 parts of sodium hydroxide solution (30%) and 65 parts of thickener.
The thickener was made by mixing parts of wheat starch, 580 parts of water and 360 parts of tragacanth 6% solution.
Cotton and rayon piece goods were printed on an engraved roller with the above printing paste. The printed fabric was dried in the air and then subjected to the action of live steam containing the vapors of acetic acid. A color development took place. The printed goods were rinsed with water, boiled for 5 minutes in a 0.5% soap solution, again rinsed and dried. A deep Bordeaux dyeing of better fastness properties and brighter in shade than the products of the preceding examples was obtained. The new color is represented by the formula:
OCHa
A very large number of other coupling components which are free from solubilizing groups can be used. The most suitable type of coupling components are the aryl-amides of ortho-hydroxy-aryl-amides, of carboxylic acids and of beta-keto-carboxylic acids. Among these types are the arylides of 2:3-hydroxy-naphthoic acid, of 2-hydroxy-anthracene-3-carboxylic acid, of 2-hydroxy-carbazole-3-carboxylic acid, of 7-hydroxy-alphanaphtho-carbazole-6-carboxy1ic acid, of 2-hydroxy-diphenylene oxide-3-carboxylic acid, of aceto acetic acid, of benzoyl acetic acid, and of terephthaloyl-bis-acetic acid.
The colors may be applied by any of the processes for the application of ice colors. These are well known in the art but they find their most important use in printing according to which alkaline compositions containing the stabilized diazo component and the coupling components is printed on the fibre and developed by hydrolysis of the diazo imino compounds.
The following methods of imparting the colors to the fibres are mentioned.
1. The fibres are padded with the arylamide and then immersed in a solution of diazotized aryl amine.
2. The fibres are impregnated with the arylamide and printed with pastes containing the diazotized aryl amine.
3. The diazotized aryl amine is converted to its antidiazotate (nitrosamine) and the fibres are printed with pastes containing the antidiazotate and the arylamide. The color is then developed by treatment with a mild acid, desirably at an elevated temperature.
4. The diazotized aryl amine is reacted with one of various aliphatic, isocyclicl or heterocyclic amines which desirably contains a water solubilizing group and a diazo imino derivative is formed. The fibre to be dyed is printed with a paste containing the diazo imino derivative and the arylamide. The color is then developed by hydrolyzing the diazo imino compound, such as by acting upon the printed goods with an acid, whereupon the coupling is immediately effected.
Among the desirable stabilizing agents are, methyl glucamine, diethanolamine, sarcosine, ethyl taurine, proline and 4-sulfo-2-amino-benzoic acid. The rate of color development will vary among the different derivatives of the stabilizing agents but for a given stabilizing agent, it has been found that the rapidity of development of the diazo imino compounds is rapid.
According to the present invention a large number of new ice colors of desired shade and fastness properties are produced by processes and from components which are not costly. It is evident that the shade may be varied by varying the azo dye coupling components.
The preferred dyes are those made by coupling diazotized cresidine and the anilides of 2:3-hydroxy naphthoic acid. The anilide nucleus may be unsubstituted or it may be substituted by alkyl, alkoxy, halogen or nitro such as chloro, bromo, methyl, ethyl, propyl, butyl and the corresponding alkoxy groups. From considerations of cost, brightness of color, fastness and general excellence, the anilides of 2:3-hydroxy-naphthoic acids in which the benzene ring of the anilide is substituted by two alkyl groups and a nitro or ohloro group or by three methyl groups in the 2:4:5-positions with respect to the amino group are preferred.
Since from the foregoing description of the invention it will be apparent to those skilled in the art that many embodiments of the invention may be made without departing from the spirit and scope thereof, it is to be understood that no limitations are intended in the annexed claims except those which are specifically recited or are imposed by the prior art.
I claim:
1. A compound represented by the formula:
(F CH A compound of claim 1 in which X is methyl. The compound represented by the formula:
oom
N:N (EH9 on c o NH O Cl 1 r The compound represented by the formula:
l CH3 The compound represented by the formula:
OCHa
FRITHJ OF ZWILGMEYER.
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USRE22133E true USRE22133E (en) | 1942-07-14 |
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