USRE19527E - Azo dyestuff and process of making - Google Patents
Azo dyestuff and process of making Download PDFInfo
- Publication number
- USRE19527E USRE19527E US19527DE USRE19527E US RE19527 E USRE19527 E US RE19527E US 19527D E US19527D E US 19527DE US RE19527 E USRE19527 E US RE19527E
- Authority
- US
- United States
- Prior art keywords
- red
- nitro
- bordeaux
- chloro
- toluidine
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 6
- 210000004940 Nucleus Anatomy 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- BKFXSOCDAQACQM-UHFFFAOYSA-N 3-chlorophthalic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(O)=O BKFXSOCDAQACQM-UHFFFAOYSA-N 0.000 description 1
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 240000000800 Allium ursinum Species 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H Aluminium sulfate Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N Roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 229940116362 Tragacanth Drugs 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- IGQFKZCLTLAWLO-HYNBPGMHSA-M sodium;4-[(2E)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N\N=C\1C2=CC=CC=C2C=CC/1=O IGQFKZCLTLAWLO-HYNBPGMHSA-M 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 229940013123 stannous chloride Drugs 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth 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
Definitions
- nucleus in which the nucleus may be substituted by one ormore substituents selected from the group consisting of halogen, alkyl, alkoxy and nitro groups but which does not contain any group causing solubility, such as the sulfonic acid or carboxylic acid group, with an othro-alkoxyarylide of the 2, 3-hydroxynaphthoic acid of the general formula:
- COAQHQ Alkyl wherein the nucleus R may be substituted by a substituent selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.
- the new dyestuiis are represented by the general formula:
- nuclei R and R1 may be substituted by substituents selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.
- the dyestuffs can be used for the production of color lakes of an excellent fastness to light and give, when produced on the fiber, orange to red and Bordeaux shades of asingularfastness tolight, they are when dry, orange to red and brownish powders, insoluble in water, soluble in sulfuric acid to a violet to green solution yielding upon reduction with stannous chloride an amine and an ortho-alkoxyarylamide'of the l-amino-2-hydroxy-3-naphthoic acid. 1
- a diazo-solution prepared in the usual manner from 16.2 parts of 2,5-dichloroaniline, is poured, while stirring well, into an aqueous suspension of 30.7 parts of ortho-anisidide of the 2,3-
- hydroxynaphthoic acid prepared by dissolving it in dilute caustic soda lye and precipitating with dilute acetic acid.
- the dyestuff separates in brightly reddish flakes, it is filtered, when the combination is complete, washed until neutral and advantageously used in the form of a paste.
- Mixed with the usual substrata it forms color lakes of an excellent fastness to light.
- the dyestufi has the following structural formula:
- ortho-anisidide instead of ortho-anisidide we may use orthophenetidide of the 2,3-hydroxynaphthoic acid.
- the dyed goods are rinsed, as usually, with cold and warm water, then soaped, while boiling well, rinsed again and dried.
- Printing-directions Printing-color 4500 cc. of the diazo solution
- a substituent selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.
- an object of the present invention is; to provide dyestuffs of goodfastness properties, which dyestuffs are insoluble. in water and all kalies, it is to be understood 'tl'mt the aromatic nuclei of the general formulae appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkaliesand to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are ⁇ for instance, the sulfonic acid and the earboxylic acid group.-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Reissued Apr. 9, 1935 UNITED STATES PATENTS OFFICE 19,527 AZO DYESTUFF AND PROCESS orv MAKING SAME August Leopold Laska and Arthur Zitscher, f-
fenbach -,0'n the Main, Germany, assignors to I. G. Farbenindustrie Aktiengesellschalt, Frankfort-on-the-Main, Germany No Drawing. Original No. 1,457,114, dated May 29, 1923, Serial No. 611,503, January 8, 1923. Application for reissue August 28, 1932, Serial 3 (,laims.
aromatic amine in which the nucleus may be substituted by one ormore substituents selected from the group consisting of halogen, alkyl, alkoxy and nitro groups but which does not contain any group causing solubility, such as the sulfonic acid or carboxylic acid group, with an othro-alkoxyarylide of the 2, 3-hydroxynaphthoic acid of the general formula:
, COAQHQ Alkyl wherein the nucleus R may be substituted by a substituent selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.
The new dyestuiis are represented by the general formula:
wherein the nuclei R and R1 may be substituted by substituents selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.
The dyestuffs can be used for the production of color lakes of an excellent fastness to light and give, when produced on the fiber, orange to red and Bordeaux shades of asingularfastness tolight, they are when dry, orange to red and brownish powders, insoluble in water, soluble in sulfuric acid to a violet to green solution yielding upon reduction with stannous chloride an amine and an ortho-alkoxyarylamide'of the l-amino-2-hydroxy-3-naphthoic acid. 1
The invention is illustrated by the following examples:
1'. A diazo-solution, prepared in the usual manner from 16.2 parts of 2,5-dichloroaniline, is poured, while stirring well, into an aqueous suspension of 30.7 parts of ortho-anisidide of the 2,3-
hydroxynaphthoic acid, prepared by dissolving it in dilute caustic soda lye and precipitating with dilute acetic acid. The dyestuff separates in brightly reddish flakes, it is filtered, when the combination is complete, washed until neutral and advantageously used in the form of a paste. Mixed with the usual substrata it forms color lakes of an excellent fastness to light.
The dyestufi has the following structural formula:
CHI.
Instead of ortho-anisidide we may use orthophenetidide of the 2,3-hydroxynaphthoic acid.
2. PRODUCTION OF THE DYESTUFFS ON II-IE FIBER Padding bath 10 rams of ortho-anisidide of 2,3-hydroxynapht oic acid are well stirred with 20 cc. of caustic soda lye of 34 B. and 20 cc. of Turkey red oil, dissolved with 200 cc. of hot water and made up to 1 liter.
The cotton goods, which are impregnated with this solution, are well wrung out and then developed in the following:
3 grams of 4-chloro-1,2-toluidine are diazotized in the usual manner, the solution is diluted with cold water to I liter, neutralized with sodium acetate and 50 grams of common salt are added.
The dyed goods are rinsed, as usually, with cold and warm water, then soaped, while boiling well, rinsed again and dried.
Printing-directions Printing-color 4500 cc. of the diazo solution,
4000 grams of tragacanth thickening 1:20, 1000 cc; of aluminium sulfate 1:1, I
500 ec.-. of sodium: acetate 1 :1, 1 a.
by a substituent selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.
2. The water-insoluble azo dyestuffs of the general formula: I
10 After printing the goods are dried-at 40 (Lto 5p? 0., soaped with a warm and fbly alkalifieso'lii x tion of soap and rinsed with hot water.
The following table gives the-tints o r =number of the dyestuffs, prepared according to the" present: 6 ONH@ process, and of the color lakes obtained there from: m -1 Diazo compiflifidofz r I Combined with: Shades:
1 3-chloroaniline Ortho-anisidide of 2 fi-liydroxynaphthoic acid--- Orange. 2 2-ch1oroaniline. a o Yellowish red. 3 2, -dicl1loroaniline Yellowish red. 4 4-chloro-l, 2-toluidine. Red. 5 5-chlol'0-1; 2-toluldin Blulsli'red 6 6'chloro-1, Z-toluidin ed. 7 Yellowish red. 8 Bluish red. 9 Bordeaux 10 Red. 11 Yellowish red 12 Bordeaux. 13 Bordeaux. 14 Bordeaux. 15 3-nitro-l, 4-toluidiue Red.
16 40hl0lO-2-filti'0B-l1llltl8; Y Bluish red. 17 Dianisidine Reddish blue. 18 Ortho-phenetole-azo-a]pha-naphtliylamine Black. 19 4-cl1loro-l, 2-toluidine d- 20 5-cl1loro-l, 2-toluidine Bluish red. 21 fi-chloro-l, 2-toluidine Red; 22 2-chloro-l, 4-toluidine Red. 23 3-chloro-1, 4 toliiidine. Red. 24 4-chl0ro-2-nitroan1line: Bluish red. 25 4-chloro-l, 2-anisidine- Bordeaux. 26 5-chloro-1, 2-anisidine. Reddisli Bordeaux. 27 4-nitro-l, z-anisidine Bluish red. 28 E-nitro-l, Z-toluidine Red. 29 3-nitro l, 4=toluidjne Reddish Bordeaux. 30 m-aminoazptoluene Like garnet. 31 5chloro-1, 2-toluid1'ne. Bluish red. 32 6-chloro-1, 2-toluidilge Yellowish red. 33 4-chloro-l, Z-aniSidln. Bordeaux. 34 3-nitrol, 4-to1uidine Bordeaux. 35 S-nitro-l, 4-to1uidine. Bluish red. V 36 5'-nitro-1, 2-anisldine; Reddish Bordeaux. 37 2, 5-dichlofoaniline Yellowish red. 3s 3-nitro-l, 4-toluidine 'Blui s'h red. 39 5-nitro-l, 2-toluidin 0.; Bordeaux. 40 2, S-diChIoib-aniline. 2, Flo-5ydroxynaphthoyl-3-ammo-l, 4-creso1ethyl- Yellowlsh red.
' e er. 41 3-nitro-l, 4-toluidine'. do Bluish red. 42 5-nitro-1, 2-toluidine. do Bluish red. 43 4-nitro-l 2-anisidine. Red.
44 4-"chloio-l, 2-anlsidine 'Bluish red. 45 2, .5-dichloroaniline; Brownish orange.
Since an object of the present invention is; to provide dyestuffs of goodfastness properties, which dyestuffs are insoluble. in water and all kalies, it is to be understood 'tl'mt the aromatic nuclei of the general formulae appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkaliesand to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are} for instance, the sulfonic acid and the earboxylic acid group.-
1. The water-insoluble 'a'zo" dyestuffs of the general formula: I 1 Y wherein the nuclei R aiid fumayue substituted oo-NH OCH;
suorus'r LEQPOLDV ARTHUR ZITSCHER.
Publications (1)
Publication Number | Publication Date |
---|---|
USRE19527E true USRE19527E (en) | 1935-04-09 |
Family
ID=2083718
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US19527D Expired USRE19527E (en) | Azo dyestuff and process of making |
Country Status (1)
Country | Link |
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US (1) | USRE19527E (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2436697A (en) * | 1944-07-31 | 1948-02-24 | American Cyanamid Co | Sulfofluorides of azoic dyestuffs |
US2468600A (en) * | 1945-12-29 | 1949-04-26 | American Cyanamid Co | Water-insoluble monoazo dye |
US2477661A (en) * | 1943-03-13 | 1949-08-02 | Interchem Corp | Disazo dianisidine pigments |
US2502911A (en) * | 1947-08-07 | 1950-04-04 | Edward L Wolfram | Method of cleaning azo printed regenerated cellulose gel with hydrated alumina |
US2518077A (en) * | 1946-03-08 | 1950-08-08 | Ciba Ltd | Azo-dyestuffs |
US2540705A (en) * | 1946-10-29 | 1951-02-06 | Du Pont | Modified azo dyestuffs |
US2573851A (en) * | 1947-11-10 | 1951-11-06 | American Cyanamid Co | Light fast azoic pigments |
US2899420A (en) * | 1959-08-11 | Water insoluble monoazo dyestotfs | ||
US2899421A (en) * | 1959-08-11 | Monoazo-dyestuffs insoluble in water |
-
0
- US US19527D patent/USRE19527E/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2899420A (en) * | 1959-08-11 | Water insoluble monoazo dyestotfs | ||
US2899421A (en) * | 1959-08-11 | Monoazo-dyestuffs insoluble in water | ||
US2477661A (en) * | 1943-03-13 | 1949-08-02 | Interchem Corp | Disazo dianisidine pigments |
US2436697A (en) * | 1944-07-31 | 1948-02-24 | American Cyanamid Co | Sulfofluorides of azoic dyestuffs |
US2468600A (en) * | 1945-12-29 | 1949-04-26 | American Cyanamid Co | Water-insoluble monoazo dye |
US2518077A (en) * | 1946-03-08 | 1950-08-08 | Ciba Ltd | Azo-dyestuffs |
US2540705A (en) * | 1946-10-29 | 1951-02-06 | Du Pont | Modified azo dyestuffs |
US2502911A (en) * | 1947-08-07 | 1950-04-04 | Edward L Wolfram | Method of cleaning azo printed regenerated cellulose gel with hydrated alumina |
US2573851A (en) * | 1947-11-10 | 1951-11-06 | American Cyanamid Co | Light fast azoic pigments |
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