US2277544A - Process of producing fast dyeings - Google Patents
Process of producing fast dyeings Download PDFInfo
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- US2277544A US2277544A US2277544DA US2277544A US 2277544 A US2277544 A US 2277544A US 2277544D A US2277544D A US 2277544DA US 2277544 A US2277544 A US 2277544A
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- 238000004043 dyeing Methods 0.000 title description 14
- 238000000034 method Methods 0.000 title description 10
- 239000000835 fiber Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 18
- 229920003043 Cellulose fiber Polymers 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002657 fibrous material Substances 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- PSIKAQNVARWEFI-UHFFFAOYSA-N 3-phenyldiazenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(N=NC=2C=CC=CC=2)=C1 PSIKAQNVARWEFI-UHFFFAOYSA-N 0.000 description 1
- ANWCFOBHFNQQSV-UHFFFAOYSA-N 5-[(4-aminobenzoyl)amino]-2-hydroxybenzoic acid Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=C(O)C(C(O)=O)=C1 ANWCFOBHFNQQSV-UHFFFAOYSA-N 0.000 description 1
- FORCWSNQDMPPOC-UHFFFAOYSA-N 5-methyl-4-(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)-2-phenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1C(C1=O)C(C)=NN1C1=CC=CC=C1 FORCWSNQDMPPOC-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- -1 metal complex compound Chemical class 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Description
Patented Mar. 24, 1942 U ITED; STATES PATENT Q F E',
PROCESS OF PRODUCING FAST DYEINGS ANDTHE BY FIBER OBTAINED THERE- Erich Fischer and Walter Gmelin, Bad Soden in Taunus, and Werner Kirst, Konigstein in Taunus, Germany, asslgnors to General Aniline & Film Corporation, New York, N. .Y., a corpo-" ration of Delaware No Drawing. Application November 21, 1940, serial No. 367,379. In Germany July 24, 1939 g f 8 Claims. The present invention relates to a process oi producing fast dyeings on cellulose fibers or mix-. tures of cellulose fibers with animal fibers, and
to the dyed fiber obtained thereby.
We have found that drains of very good properties of i'astness may be obtained 'on cellulose fibers or mixtures of cellulose fibers with animal fibers, for instance: staple fiber from I thus obtained to a treatment with an agent,
yielding metal.
The'tollowin'g examples serve \to illustrate the invention, but they are not intended to' limit it thereto:
, (1) 1 kilo of a mixed fabric made from 50 parts of wool and 50 parts oistaple fiber from viscose I is dyed for one hour at 95 C. in a bath containing 40 grams of thegazo-dyestufl. obtainable by coupling diazotized 1-(4-amino-benzoylamino) 4-hydroxybenzene-3-carboxylic acid with 1-(3'- aminophenyl) -5-pyrazolone-3-carboxylic acid, 40 grams of ammonium sulfate, and
600 grams'orsodium sulfate in 30 liters of water..
The temperature is allowed to fall to 80 C. within30 to 45 minutes, whereuponthe material is rinsed and treated for half an hour in the cold with a solution containing 25 grams of sodium nitrite,
grams of sodium 'dibutylnaphthalenesulionate and '75 cc. oi hydrochloric acid of 2i)"v B6. in
} 3i) liters of cold water.
,The dyestufl is then developed for ha l an hour in a bath containing 75 cc. of ammonia of per cent strength and 5 grams of the product obtained by condensation of 1 moi of octodecyl alcohol with 20 mols of ethylene oxide in '5 liters oi cold water.
The material is then after-treated for one h at 90 'C. with a solution containing 2 0 1 grams of chromic fluoride,
10 10 grams of glacial acetic acid and i 5 grams of the product obtained by condensation. of 1 mol of octodecyl alcohol with 20 mole ethylene oxide in 30 liters of water,v 1
rinsed and dried. A g olden yellow dyeing oi 800d properties of iastnessis obtained.
(2) 1 kilo of a mixture from 50 parts of wool and 50 parts of staple fiber from viscose is treated for one hour at 95 C. in a solution containing 40 grams of the azo-dyestufi oi the following constitution:
(obtainable by coupling 1 molof 4.4'-bis- [5-oxo- 3-methyl A pyrazolinyl -(1) ]-stllbene-2.2-disulfonic acid which may be obtained from 4.4- dihydrazino-stilbene-2.2'-disulfonlo acid. and
acetoacetic ester, with 1 mol of dlazotized 1- aminobenzene-Z-carboxylic acidandl mol of diazotized l-amino-4-nitrobenzene and reducing the nitro-group to the aminogroup),
40 10 grams of the product obtained by condensation or 1 .mol oi octodecyl alcohol with 20 mole of ethylene oxide and l i 80 grams of ammonium sulfate in 3o liters of water.
600 grams of sodium sulfate are then added and the materiaiisallowed to stand for .45 minutes.
atja temperature ialling to 10 C. rinsed and fur-- ther treated. in the manner indicated in Example 1. A yellow .dyeing or good properties of fastness is obtained.
(3) 1 kilo oia mixture of 50 parts of wool and 50 parts oi. staple'fiber from viscose is dyed i'or '45 minutes at C.. in a bath containing I ing constitution:
CH: C H:
3 Dell 4 l l C} 110 H i NH:
(obtainable by coupling diazotized l-l' -nitroe The material is then allowed to stand for 45 benzoylamino] -4-aminobenzene-3-sulfonic acid minutes at a temperature falling to 70 C., rinsed with 1- [2'-hydroxy-3'-carboxy-5'-sulfophenylland further treated for half an hour in the cold 3-methyl-5-pyrazolone, reducing the nitro-group with to the amino-group, further diazotizing the ami- 15 no-monoazo-dyestufi? obtained and coupling it 25 grams ofisodPlm f m with 1 [3' aminopheny1] 3 methy1 5 pyrazm 1O grgms of sodium d1butylnaphthalenesulfonate lone), an
5 h hl f 20 grams of the product obtained by condensa- 2 m g: gglz one acld o B in tion of 1 mol of octodecyl alcohol with 20 mols of ethylene oxide, and the dyestufi is developed for half an hour 40 grams of ammonium sulfate and in a t containing 600 grams of sodium sulfate in 30 liters of water. '75 cc. of ammonia of 25'per cent strength and I The material is allowecl to stand for 45 minutes 5 grams of the product obtamed condensatmn at a temperature falling to C" rinsed, diazm of 1 mol of octodecyl alcohol with 20 mols of tized, developed and after-chromed in the manethylene oxide in ner indicated in Example 1. liters of cold wateris g igfig ng 0 good properties of fastness The material is then after-treated for one hour (4) 1 kilo of a mixture of 50 parts of wool and at with a solution containing 50 parts of staple fiber from viscose is dyed for 20 o grams of chromic fluoride, 45 minutes at 90 C. in a bath containing. 10 grams of glacial acetic acid and r 30 grams o t y fi described in 5 grams of the product obtained by condensation ample 3,
30 grams of the azo-dyestufi: l-amino-5-hydroxy-naphthalene-"l-sulfonie acid l-aminonaphthalene-'l-sulfonic acid l-amino-nap'nof 1 mole! octodecyl alcohol with 20 mols of ethylene oxide in 30 liters of water,
thalene-7-sulfonic acid, rinsed d dried 10 grams 'of the product obtained by condensa- A brown dyeing of good Properties of fastness tion of 1" mol of 'octodecyl alcohol with 20 rnols is Obtainedp of ethylene i I a- The following table indicates the shades of a. grams f amm ium lfat and number 0! other dyeings obtainable by this in- 600 grams of sodium sulfate in 'vention:
30 liters of water.
Patent oompment Shade oi the dyeing treated with metal salts on mixtures of wool and artificial silk staple fiber- (obtainable by coupling 1 mol of 4.4'-bis-[5-oxo-3-metlgl-A'-pymzolln l-(1)]-etilbene-2.2'- disulionic acid (see Example 2) with 1 mol 0! diam zed l-amino-4- ydroxybenzene-B- carboxylic. acid and l min] or diazotized l-amino-2-hydroxy-4-nitrobonzene and reducing the nitro-group to the amino-group).
Treated with chromic fluoride or potassium biehromate: brown.
on, I on. =;N\ I /N=( .3 l 1 2. N=NC=C- c= -N=N.C0.HN on 5 1103s SOaH I H OH NH: 7 00B (obtainable by couplingl mol of the bis-pyrazolone from 4.4-bis hydrazino-l.l'-diphenyl- Treated with chromic fluoride or potassium 2.2-disulfonic acid and aeetoacetie ester with 1 mol of diazotized l-amino-Zi-nit'mbenzene bichromate: yellow. and 1 mol of diazotized 1-[4'-eminobenzoylaminoH-hydroxybenzeneii-earboxyhc acid and subsequently reducing the nitro-group to the amino-group).
e I i r Shade of the dyeing treated with metal salts n Pam! mipmni mixtures oi wool and artificial silk staple liber v cm I am C=N\ /N=C r l 3. NH N= -c=c 4 c= -N= N N=N on I H038 80:11 I OH OH C O OH O O H (obtainable by cou link 1 mol oi the bis-pyrazoione from 4.4-bis-hydrazino-1. l'- Treated with chromic fluoride or potassium I dipheny1-2.2'-disul onle acid and acetoaeetic ester. with 1 mol oi diaz'otized l-aminobichromate: brown-orange. 4-nitrobenzene-2-carboxylic acid and 1 mol 0! diazotized 4-amino-4'-hydroxy-l.1-
azobenzene-3-carboxylic acid and reducing the nitro-group to the amino-grou 4. 4-amino-l.l'-azobenzene-3-carboxylic aci-y-sulioniciacid 1(3'-aminophcnyl)- Treated with ehromic fluoride: orange.
6-pyrazolone-3-carb03llc acid. I 0H v (obtainable by con ling 1 moi of the pyrazolone irom the hydrazine oi dehydrothioto- Treated with chromic fluoride: ycllowish-brown. luidinesulionic ac d and acetoacetic ester, with 1 mol oidiazotized I-am no-Z-hydroxy- 4-nitrobenzene and reducing the nitro-group to the amino-group).
6. 4-arnino-4'-hydroxs -1.1'-azobenzene-3-mrboxylic acid 1- -amino-phenyl)-5- Treated with chromic fluoride: red.
pyrazoionee-carboxyllc acid. I 7
c 0 011 v c 0 or! (obtainable by coupling 1 mol of 4.4'-bis-[5-oXc-3-methyl-N-p razolinyl-(i)l-stilbene- Treated with gotassium hichroniate: orange,
2.2'-disulionic acid (see Example 2) with 1 moi of diazotized l-ammo-a-hydroxybcnzene- I with chromic uoride: yellow. 3-carboxylic acid and l moi oi-diazotized l-arn1no-4-nitrobenzene-2-carboxylic acid and reducing the nitroqzrouptc the amino-grogp). v
. 1 ac: 8. 1-(4'-aminophenyl)-3-methyl-5-pyrazoione 2-amino-5-hydroxy-naphthelene-7- Treated with chromic'fluoride: brown.
,1 sulionic acid l-amino-4-hydroxybenzene-3mrboxylic acid.
(obtainable by coupling 2 mols of diazotized 5-nitro-2-arniuo-l-hydroxybenzene-Q Treated with copper sulfate: brownish red.
sulionic acid with 1 mol oi the urea irorn 1-(4'-amino;iil;enyl)-3-methyl-5-pyrewwne and subsequently reducing the nitro-zroups. or by coup g 1 mol oi dtazotized B'n tro- 2-amino-l-hydroxybenzene-4-sulionic acid with 1 moi of l-(4f-aminophenyD-3-met hyl- 5-pyrazolone, phosgenating and reducing the urea thus obtained).
N=N NH 10 OH Sol-NH SOaH Hons N I v OOH (ob tainablc by coupling the tetrazo-compou nd lrorn 1 mol of para-amino-benzoyl- Treated with chromic fluoride: red. pamphenylenediamineinan acid medium, with lznol of 1- -amino-4'-suliophenyl)- A fi-pyrazolone-ii-carboxylio acid and subsequently coupling the compound obtained with s 1 mol oi 2-(4'-hydroxy-a'mrboxy-phenyl-sul onyl)-amino-5-hydroxy-na h. 'thalene-7-sulionlcacid in the presence of sodium carbonate).
We claim: 4 A v I aninial fibers, which comprises applying to the 1. A process of producing iast-" dyeings. on fiber a water-soluble pyrazolone-azo-dyestufise- -fibrous material of the group consisting of cellulected from the group consisting of monoand lose fibers and mixtures oicelluloce fibers with diaazo-dyestufls which contains in the molecule 4- aerate; g at least one amino-group capable-of being diazo the dyeingsthus obtained to a treatment with tized and at least one grouping capable of forman agentyielding chromium. ing a metal complex compound, but noihydroxyl 4. A process of producing iast brownish-red group rendering coupling possible, then diazodyeings' on fibrous material of the group consisttizing, developing thedyestufl by means or an 1 ing of cellulose fibers and mixtures of cellulose alkaline treatment and subjecting the 'dyeings fibers withenimal-fibers i h co p ise appl thus obtained to a treatment with an agent yielding to the .fiber a water-soluble pyrazolone-azomg metal. 5 dyestufl o! the following constitution: A H v f O NH N N-Q= I on SOzH
2. A process of. producing fast yellow dyeings then diazotizing, developing the dyestufi "by on fibrous material of the group consisting oimeans of an alkaline'treatment-and subjecting cellulose fibers and mixtures of cellulose fibers the dyeings thus obtained to a treatment with arr with animal fibers which comprises applying to agent yielding copper. j
the fiber a water-soluble pyrazolone-azo-dyestuif 5. Fibrous material of the group consisting of of the following constitution:
SOaH
then diazQtiz ing, developing the dyestufl by with animal fibers, dyed with a water-soluble means of an alkaline treatment and subiecting 'pyra lon -a y s uff selected from the grou the dyeings thus obtained to a treatment with an consisting of monoand disazo-dyestufis by the cellulose fibers and mixtures of cellulose fibers agent yielding chromium. process claimed in claim 1. v
3. A process of producing fast golden-yellow 6. Fibrous material of the group consisting of .dyeings on fibrous material of the group consist-- cellulose fibers'and mixtures of cellulose fibers ing of cellulose fibers and mixtures of cellulose wi h an mal fibe s, dyed h a Water-sol ble fibers withanimal fibers, which comprises appy o fl y y the Process a m plying to the fiber a water soluble pyrazolonein cl i l azo-dyestufl of the following constitution: i rous t al of t e oup consisting of P N'Hft p cellulose'fibers and mixtures of cellulose fibers o g with animal fibers,-dyed with a water-soluble- I pyrazolone-azo-dyestufl by the process claimed in claim 3 v 8. Fibrous material of the group consisting "of N i cellulose fibers and mixtures of cellulose fibers with animal fibers; dyed with-a water-soluble W V COO'H 5o 7 ERICH FISCHER. I 1 l I s WAL'I'ER-GMEHN. then diazotizmg. developing the dyestufl .by' I WERNER KIRST. means of an alkaline treatment and subjecting l
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2277544A true US2277544A (en) | 1942-03-24 |
Family
ID=3432518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2277544D Expired - Lifetime US2277544A (en) | Process of producing fast dyeings |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2277544A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538180A (en) * | 1946-04-16 | 1951-01-16 | Ciba Ltd | Polyazo dyestuffs |
| US2753333A (en) * | 1952-10-27 | 1956-07-03 | Ciba Ltd | Cupriferous trisazo-dyestuffs |
-
0
- US US2277544D patent/US2277544A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538180A (en) * | 1946-04-16 | 1951-01-16 | Ciba Ltd | Polyazo dyestuffs |
| US2753333A (en) * | 1952-10-27 | 1956-07-03 | Ciba Ltd | Cupriferous trisazo-dyestuffs |
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