US2277551A - Process of producing fast dyeings and the dyed fiber obtained thereby - Google Patents

Process of producing fast dyeings and the dyed fiber obtained thereby Download PDF

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US2277551A
US2277551A US367377A US36737740A US2277551A US 2277551 A US2277551 A US 2277551A US 367377 A US367377 A US 367377A US 36737740 A US36737740 A US 36737740A US 2277551 A US2277551 A US 2277551A
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Kirst Werner
Fischer Erich
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GAF Chemicals Corp
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General Aniline and Film Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/64Natural or regenerated cellulose using mordant dyes or metallisable dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/20Wool using mordant dyes using metallisable dyes
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/907Nonionic emulsifiers for dyeing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile

Description

Patented Mar. 24, 1942' AND THE DYED FIBER OBTAINED THERE- Werner Kirst, Konigstein in Taunus, and Erich Fischer, Bad Soden in 'l'aunus, Germany, assignors to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing Application November 27, 1940, I Serial No. 367,377. In Germany July 4, 1939 .13 Claims.
The present invention relates to a proces of producing fast dyeings on cellulose fibers or mixtures of cellulose fibers withanimal fibers and to the dyed fiber obtained thereby.
A known method of producing fast dyeings on wool consists in applying to the fiber water-soluble azo-dyestufis containing a grouping capable of forming a metal complex compound, and subsequently treating the dyeings with an agent yielding chromium. In the practice of dyeing cotton only disazo-dyestufis or polyazo-dyestuffs which contain a salicylic acid grouping or are derivatives of 1.8-dihydroxynaphthalene-4-sulfonic acid, have been after-treated with agents yielding chromium.
Now, we have found that dyeings of very good properties of fastness can be produced on cellulose fibers or mixtures of cellulose fibers with animal fibers, for instance staple fiber from viscose or cuprammonium cellulose and wool, by applying to th fiber a water-soluble azo-dyestuff side the said oxidizing agent and cobalt salt one containing at least one free amino-group and at v least once the following grouping:
x being ma, NH.alk yl, N(alkyl)z or on, and
then treating the dyeing obtained with a mixture of cobalt salts and chromates, hydrogen peroxide, alkali-persulfates or alkali perborates.
In general it is not possible to produce on celing agents named above. Removal of the dyestuff from mixed fibers occurs to a much smaller extent so that it ispossible, by selection of appropriate methods of dyeing, to produce even dyeings on mixed fibers.
The dyeing is after-treated with the mixture of the metal salts in a neutral or acid solution at a raised temperature. The mixture may contain any chromate or bichromate or any other of the above-named oxidizing agents, and a cobalt salt, as for instance, cobalt sulfate, cobaltous chloride, cobalt acetate or cobalt chromate. By varying the amount of the salt mixture applied and the mixing proportion between the cobalt salt and the oxidizing agent, the shade may be displaced within certain limits and the velocity of the reaction on the fiber may be influenced.
To the mixture of the oxidizing agents andcobalt salts may be added a dispersing agent, as for instance the condensation product from 1 mol of octodecyl alcohol and 20.mols of ethylene oxide, as well as a protective colloid, whereby the fastness to rubbing oi the dyeings is improved. It is also possible to treat the material in the same process of after-treatment with a moth preventive agent, as for instance the product obtained by condensation of 1 mol of benzaldehyde-ortho-sulfonic acid with 2 mols of 2.4- dichloro-l-hydroxybenzene.
The after-treatment baths may contain beor' more other metal salts, as for instance chromic salts. A chromic salt favorably influmixes the properties of fastness of the dyeings, especially when the molecule of the dyestufi contains a salicylic acid grouping.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto:
(1) 1 kilo of a fabric made from 50 parts of wool and 50 parts of "staple fiber from viscose is dyed for one hour at-85 C. in a bath contain-. ing 70 grams of the sodium salt of the reduced I-amino-Z-hydroxy 4 nitrobenzene' '3"-aminobenzoyl '-3'- aminobenzoyl-2-amino-S-hydroxynaphthalene 7 -sulfonic acid, 8 grams of the product obtained by condensation of 1 mol of octodecyl alcohol with 20 mols of ethylene oxide, grams of ammonium sulfate and 600 grams of sodium sulfate in 30,000 cc. of water. The material is then further dyed for one hour at a temperature falling to 70 C., rinsed well and treated for one hour at (L- C. in a fresh bath containing 50 grams of a mixture of 20 grams of potassium bichromate, 10 grams of cobaltous chloride and 20 grams of the neutralized condensation product from betanaphthalenesulfonic' acid and formaldehyde, and 20 cc. of acetic acid oi. 50 per cent strength in 30,000 cc. of water, rinsed again and dried.
A black tone-in-tone dyeing of very ood properties of fastness is obtained. I (2) 1 kilo of skein of artificial silk staple fiber is dyed for one hour at 70 C .-90 C. in abath containing in 20,000 cc. of water 60 grams of the sodium salt of the reduced azo-dyestuff l-amino- 2-hydroxy-4-nitrobenzene 2-amino-5-hydroxynaphthalene-7-sulfonic acid i amino-2-hydroxy-5- nitrobenzene 3 sulfonic acid and 400 grams of sodium sulfate. The material is then rinsed and treated for 45 minutes at 90 C. in a fresh bath containing-50 grams of a mixture of 20 grams of potassium bichromate, 10 grams of cobaltous chloride and 20 grams of a neutralized condensation product from betanaphthalenesulfonic acid and formaldehyde, and 20 cc. ofacetic acid of 50 per cent strength in 20,000 cc. of water, rinsed again and dried. A black dyeing of very good properties of fastness is obtained.
If the dyeing is produced on a fabric which contains eflects of acetate silk. these effects are not dyed.
(3) 1 kilo of mixed yarn consisting of 50 parts of wool and 50 parts of staple fiber from viscose is treated for one hour at 85 C. in a bath containing in 24,000 cc. of water 50 grams of the sodium salt of the reduced azo-dyestufl l-amino- 2 -hydroxy-4-nitrobenzene 2-acetylamino-5-hydroxynaphthaiene-7-sulfonic acid, 8 grams of the condensation product from 1 mol of octodecyl al-. cohol and 20 mols of ethylene oxide, and 80 grams of ammonium sulfate. To this solution are added 600 grams of sodium sulfate, dissolved in 6000 cc. of water, and the material is further dyed for half an hour at about 70 C., rinsed well and treated for one hour at 90 C. to 95 C. in a fresh bath containing in 30,000 cc. 01 water 60 grams of a mixture of 20 grams of potassium bichromate, 20 grams of cobaltous chloride and 20 grams of the condensation product from 1 mol of octodecyl alcohol and 20 mols of ethylene oxide. A black dyeing of very good properties of fastness, especially of a very good fastness to wet-processing is obtained.
When the dyeing is after-treated in a bath containing in 30,000 cc. of water 60 grams of a mixture of 10 grams of potassium bichromate, 10 grams of chromic fluoride, 20 grams of cobaltous chloride, and 20 grams of the condensation product from 1 mol of octodecyl alcohol and 20 mols of ethylene oxide.
A black dyeing. having similar properties of fastness is likewise obtained.
(4) 1 kilo of a mixed fabric consisting of 50 parts of staple fiber from viscose and 50 parts of wool is dyed for one hour at 85 C., in a bath containing in 30,000 cc. of water '70 grams of the sodium salt of the reduced azo-dyestui'f l-amino- 2-hydroxy-5-chlorobenzene acid 2-amino-5-hydroxynaphthalene-7-sulfonic acid alkaline 1-amino-2-hydroxy-3- nitrobenzene 7 sulfonic acid, grams of the condensation product from 1 mol of octodecyl alcohol and mols of ethylene oxide, and 80 grams of ammonium sulfate, 600 grams of sodium sulfate are then added and the fabric is further dyed for about half an hour at a temperature falling to 70 C., rinsed and treated for one hour at 90 C.-95 C. in a bath containing in 30,000 cc. of water 50 grams of a mixture of 20 grams of potassium bichromate, 10 grams of cobaltous chloride and 20 grams of the neutralized condensation product from betanaphthalene-sulfonic acid and formaldehyde, and 10 cc. of glacial acetic acid.
A blue-black dyeing of very good properties of fastness is obtained. I
(5) A mixed fabric from cotton and viscose artificial silk is impregnated on the foulard at 80 C. to 90 C. with a solution containing per liter 40 grams of the sodium salt of the reduced azo-dyestufl 1-amino-2-hydroxy-4-nitrobenzene acid 2-amino-5-hydroxynaphthalene-7-sulfonic acid.
The fabric is then dried and padded on the foulard at 80 C.-90 C. with a solution containing per liter of water 24 grams of potassium bichromate, 12 grams of cobaltous chloride and 5 cc.
60 grams of the sodium salt of the reduced azodyestufl 1 -amino-2 -hydroxy-4 -nitrobenzene acid I 1-amino-B-hydroxynaphthalene 4.6-disulfonic acid alkaline l-aminoi-nitrobenzene,
. 7.5 grams of the condensation product from 1 mol of octodecylalcohol and 20 mols of ethylene oxide,
grams oiammonium sulfate, and
600 grams of sodium sulfate.
The fabric is then further treated for half an hour at a temperature falling to 80 C., rinsed and treated for 1 hour at 0. in 30 liters of water containing 40 grams of the sodium salt of the reduced azodyestufl' 1-amino-2rhydroxy-4-nitrobenzene z-ziimino 5 hydroxynaphthalene 7 sulfonic ac d,
10 cc. of caustic soda solution of 34 Be. and
50 grams of tragacanth thickening 6:100.
The material is then dried and treated on the foulard at 90 C. with a solution containing in 1000 cc. of water 10 grams of cobaltous chloride, 12 cc. of acetic acid of 50 per cent strength and 5 cc. of hydrogen peroxide of 30 per cent strength. It is then rinsed, soaped at boiling temperature with a solution containing per liter of water 3 grams of soap and 2 grams of sodium carbonate, rinsed again and dried.
A blue-black dyeing of very good properties of fastness is obtained. 0
' 12 cc. of acetic acid of 50 per cent strength.
The material is then further treated for about hour at a temperature falling to 70 C. and rinsed. The Bordeaux-red dyeing thus obtained is after-treated for /4 hour at 90 C.95 C. in a bath containing in 30 liters of water 20 cc. of hydrogen peroxide of 30 per cent strength,
30 cc. of acetic acid of 30 per cent strength and 20 grams of cobaltous chloride.
A dark-violet tone-in-tone dyeing of very good properties of fastness is obtained.
(9) 1 kilo of staple fiber from viscose is dyed for one hour at about 90 C. in a bath containing in 20 liters of water 50 grams of the sodium salt of the reduced azodyestuii 1-amino-2-hydroxy-4-nitrobenzene acid 2-amino-5-hydroxynaphthalene-7-sulfonic acid alkaline -l -amino-2-hydroxy'- E-nitrobenzene-B -sulfonic acidand 400 grams of sodium sulfate. The material is then rinsed and treated for /4 hour at 90 C. in a bath containing in 30 liters of water 20 grams of cobaltous chloride, 30 cc. of acetic acid of 30 per. cent strength and 20 cc. of hydrogen peroxide of 30 per cent strength.
A black dyeing of very good properties of fastness is obtained. 1
If in the foregoing example instead of the 9.20-
dyestufi named therein 50 grams of the sodium salt of the reduced azo-dy'estufi 1-amino-2-hydroxy-4-nitrobenzene alkaline 2-amino-5-hydroxynaphthalene-7 sulfonic acid or 50 grams of the sodium salt of the reduced azo-dyestufi l-amino 2 hydroxy 5 nitrobenzene 4' amino C phenyl-1.2-(N)-imidazolo-5- hydroxynaphthalene-7-sulfonic acid are used, there are. likewise obtained black dyeings of very I goodproperties of f astness.
(10) The cotton goods padded as-indicated in Example 7 with the hot solution of the dyestufi and dried are padded at 90 C. on the foulard with a solution containing in 1000 cc. of water 5 grams of cobaltous chloride, grams of sodium persulfate and cc. of hydrogen peroxide of 30 percent The material isthen rinsed, soaped, rinsed again and dried.
A blue-black dyeing of very good properties of fastnessisobtained.
(11) The cotton goods impregnated with the dyestufi-solution as indicated in Example 7 are dried and padded at 90 C. with a solution containing in 1000 cc. of water 5 grams of cobaltous chloride, 15 grams of sodium perborate and 12 cc. of acetic acid of per cent strength.
The material is then rinsed, soaped and dried.
A blue-black dyeing of very good properties of fastness is obtained.
(12) 1 kilo of staple fiber from viscose is dyed for one hour at 70 C.-80 C. in a bath containing in 20 liters of water grams of the sodium salt of the reduced az odyestufi 1-amino-3-nitrobenzene acid 2-amino 5 hydroxynaphthalene '7 sulfonic acid \ alkaline l-amino-2-liydroxy-5-nitrobenzene-3 sulfonic cid, 20 grams of sodium carbonate and 400 grams of sodium sulfate.
The "material is then rinsed and treated for hour at 80 C.90 C. in a bath containing in 30 liters of water 20 grams of cobaltous chloride,
20 cc. of hydrogen peroxide of 30 per cen strength and 20 cc. of acetic acid of 50 per cent strength.
After rinsing a black dyeing of good properties of fastness is obtained.
(13) 1 kilo of a mixed fabric consisting of 50 parts of wool and 50 parts of staple fiber from viscose is dyed for one hour at about 80 C. in a bath containing in 30,000 cc. of water 80 grams of the sodium salt of the reduced azodyestufi 1-amino-2-hydroxy-4-nitrobenzene alkaline l amino8-hydroxynaphthalene-4.6-disu1fonic acid, 80 grams of ammonium sulfate and 600 grams of sodium sulfate;
The fabric is then further dyed for hour at a temperature falling to about C.- C., rinsed and treated for one hour near boiling temperature in a bath containing in 30 liters of water 20 grams of cobaltous chloride,
strength, and 30 cc. of acetic acid of 30 per cent strength.
It is then rinsed and dried.
A black dyeing of very good properties of fastness is obtained.
(14) If in Example 13 the 'dyestuff used therein is replaced by grams of. the sodium salt of the reduced azo-dyestuff 1-amino-2-hydroxy-4-nitro-5-chlorobenzene alkaline 2-amino-8-hydroxynaphthalene-6 sulfonic acid,
a black dyeing of very good properties of fastness is obtained.
(15) If in Example 6 instead of the dyestufi described therein 60 grams of the sodium salt of 1130 A OaH (obtainable by coupling 1 mol of the bispyrazolone from 4.4'-bishydrazino-dlphenyl-zydisulionic acid and aceto-acetic ester with 1 mol of dlazotized l-ammo-Z-hydrox -4- mtrobem zene and 1 mol of dlazotized 4-amino-4-hydroxy-l.l-azobenzene-li'wboxylic acid and subsegiuently r ucmg the Intro-group to the amm' o'group).
Shade oi'the dyeing, treated withamixture bii i d c roma an Parent dyestufl oobaltous chloride, on mixtures of wool and artificial silk staple fiber (50:50)
37. l-amino-2-hydroxy-B-nitrobenzene-3-sulionic acid .4-amlnobenzoyl-4-aminobenzoyl-2-amino-5-hydroxynaph- Currant.
thalene-7-sulfonic acid. 3g b n -5- 1iomc 801d l-(2',3-hydroxynaphthoylamino)+aminobenzene Dark violet. 39. l-ammo-2-hydroxy-3-mtrobenzene-5sullomc acid 4-aminobenzoyl-4-aminobenzoyl-2-amino-5-hydroxynaph- C rra t,
thalenefl-sulionic acid, reduced. 40. 1-atnino-2-hydroxy-3-nitrobenzene-5-sulfomc acid 3mmnobcnzoyl-3-aminobenzoyl-2-amino-5-hydroxynaph- Dark vi l t,
' thalene-7-sulfonic acid, reduced.
801d. alkaline 41. 1-amino-2-hydroxy-4-nitrobenzeno z-amino-chy wi'ynaphthalene-7-sulionic acid 1-aminobenzene- Violet-brown.
si-sulfonic acid, reduced. 42. l-amino-2-hydroxy-c-nitrobenzened-suliomc acid 4-aminobenzoyl-4"ammobenzoyl-2-amino-5-hydroxynaph- Violet-bro th816119-7-Sl11f0111fifl0ii19du09d. 43. 2 mp5s 0g l-ammd 0-2-hydroxy-5-mtrobenzene 4.4 -b1s-[5oxo-3-methy -A-pyrazohnyl-(l)]-stilbene2,2-disulfonic Orange-brown.
am to uce acid alkaline 44. l-amino-3-nitrobenzene 2-ammo-5hydroxynaphthalene-7-sullomc acid l-amino-2-hydroxy-5-nitro- Black.
benzenew'i-sulfonicacid, reduced. 45. 1agiling-izmydiroxzl-i-mgrobenzenec-sulfonlc acid benzoyl-4-amin0benzoyl-2-amino-J-hydroxy-naphthalene-7- Dark violet.
a to caci,re uce. 46. l-amin0-2-11ydroxy-4-nitrobenzene-5-sulionic acid 4"ammo-benzoyl-4'-aminobenzoyl-2-amino-5-hydrcxynaph- Currant.
thaIencT-sullonic acid, reduced. I
acid I alkaline 47 l-amino-2-hydg-oxy-4-nitrobenzene' 1-amm08-hydroxynaphthalene-4;6-d1sulfonic acid l-amino-4- Black..
nitrobenzene, reduced. v 1
acid alkaline 48. l-amino--nitrobenzcne-Z-carboxyhc 801d. 2,-am1no-5-hydroxynaphthalene-7-sulfonic aci 1-amino-2- Black.
hydroxy-a-nitrobenzene, reduced. alkaline 4 49.'l-amino-2-hydroxy-4'nltrobenzene 2-amino-8-hydroxynaphthalenc-6-sulionic acid, reduced Bla k,
a v 50. 1-amino-2-hydroxy-4-nitrobenzene 1-8 in0 -hydr Xyn D h8lenB-6-disu1ionic acid, reduced Blue-gfey me 51. 1-amino-2-hydroxy-4-nitrobenzeue fl g iihydmxynaphtlmlene-7-sulfonic acid, reduced. Black me l 52. l-amino-2-hydroxy-4-nitro-5-ohlorobenzengl 2-am1n' o-8-hydroxynaphthalene-csulfonic acid, reduced Black me 53. l-amino-2-hydroxy-3.5-dinitrobenzene 2-amin0-5-hydr0 yn D halene-7-sulionic acid, re -h. Black.
alkaline 54. l-amino-2-hydroxy-3.5-dinitrobenzene 2-amino-8-hydroxynaphthalene-6-s'ulfonic'acid,reduced Bl k,
a 1 v 55. l-aimina-2-hydroxy-3.5-dinitrobenzene 3'-aminobenzoy 11 in y phtbalene-7-sulfonic acid, re- Black.
uce
alkaline '56.1-amino-2-hydroxy4-nitrobenzene i-ESJ Y O Y-MPM R CHH-Wsulionic acid, reduced Gley ma v 57. l-arnino-2-hydroxy-4-nitro-5-chlorobenzene l-amino-5-hydroxynaphthalene-7-suli'onicacid, reduced Black.' 58. l-amino-fiydgxy-fl-mtro-beuzcne 4"-ammo-benzoyl-4-ammobenzoyl-2-amm' o-8-hydroxynaphthalene-flsul- Black.
onic 801 ,r uce 59. l-amino-2-hydr0xy-4-nitro-benzene 2-(N-methyl-4-hydroxy-5'-carboxy-phen l-sulfon l-amino -8-h d naphthalene-G-snlionic acid, reduced.- y y y foxy Grey alkaline acid 60. lamino-241ydroxyi-nitro-benzcne l-amlno-S-hydroxynaphthalemH-sulronicacid 1-amino-4-nitro-- Olive-brown.
benzene, reduced. g
alkaline alkaline 61. 1-amlno-2-l1ydroxy-5-mtro-benzene 3esuli'onlcacid 2-ammo-5-hydroxymaphthaleneJsulfonic acid, Dark blue,
2-amino-5-hydroxy-napththaIenc7-aulion1c acid. 62. l-amino-ahydroxyi-mtrobenzene o 4-aminobenzoyl-2-amino-5-hydroxynaphthalene-7-sulfonic acid 4- Currant. hydroxy-Smrboxy-phcnylsullonytizxlno-ihydroxynaphthalene-7-sulfonic acid, reduced. 1k
. me a alinc 63. l-amino-2-hydroxy-4-nltrobenzene 2-amino-5-hydroxynaphthalene-7-suli'onic acid 2-amin0-5-hy- Black droxyna hthalene-7-sulionlc acid, reduced. m dyoxy-Q-mtro-bemne afix-k 31i;enyl-l.2-(N)-ir:nidazol0-5-11ydroxynaphthalene-7-sulionic acid, reduced. Grey.
me 65. 1-amlno-2-hydroxy-4-nitro-5-chlorobenzene 2-emiuo-5-hydroxynaphthalene-7-sulronic acid, reduced Gum ac a5, 1-amino-2-hydroxy-3.5-dinltro-benzEirgrm QE' Yd OXY P a EHMSU-HOMC acid, reduced Olive,
a me e7. 1-amin -2-hydroxy-4-nitr0benzene 2-emirxodhydroxy-naphthalenefi-sulronic acid, reduced Black,
Orange-brown.
ac inc 69. l-amino-2-hydroxy-4-nitrobenzene 2-amino-5-hydroxynaphihaleneJ-suli'onic acid 1-amm -2 hyd 3. Cum-ant chlorobenzene, reduced. yd 0 y-4-nit obenzene:3 '-d111yd1'0xy-2.2'-d1naphthylamineqj di lf i reduced Grey We claim: dyestufi containing at least one free amino- 1. A process of producing Iast dyeings on fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers which comprises applying to the l fiber an alkali metal salt of a water-soluble 2120- x 05 group and at least; once the following grouping:
wherein X stands for a member of the group consisting of NH2, NH.alkyl, N(alkyl)z and OH, and then aftertreating the dyeing obtained with a mixture of a cobalt salt and an oxidizing agent of the group consisting of chromates, hydrogen peroxide, alkali persulfates and alkali perborates.
a e; i
wherein X stands for a member of the group consisting of NH2, NH.alkyl, N(alkyl)z and OH, and then aftertreating the dyeing obtained with amixture of a cobalt salt and a chromate.
3. A process of producing fast black dyein gs the fiber an alkali metal salt of a water-soluble azo-dyestuff of the following constitution:
NH: H03 S NH:
and then aftertreating the dyeing obtained with a mixture of cobaltous chloride and potassium bichromate.
. '7. A process of producing fast blue-black dyeings on fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers on fibrous material of the group consisting of v cellulose fibers and mixtures of cellulose fibers with animal fibers which comprises applying to the fiber an alkali metal salt of a. water-soluble azo-dyestuff of the following constitution:
H O a S NH: HQNQN:
and then after-treating the dyeing obtained with r a mixture of a cobalt salt and a chromate.
4. A process of producing fast black dyeings on fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers which comprises applying to the fiber an alkali metal salt of a water-soluble azo-dy'estuff of the following constitution:
HO: S NH: nmQu:
and then after-treating the dyeing obtained with a mixture of cobaltous chloride and potassium bichromate.
5. A process of producing fast black dyeings on fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers which comprises applying to the fiber an alkali metal salt of a water-soluble azo-dyestufi of the following constitution:
N=NQNHI NH: HO: S NH:
H 035" II 0 H and then aftertreating the dyeing obtained with a mixture of a cobalt salt and a chromate.
6. A process of producing fast black dyeings on fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers which comprises applying to with animal fibers which comprises applying to the fiber an alkali metal salt of a water-soluble azo-dyestufi' of the following constitution:
NH: on n azo-dyestufi of the following constitution:
NH: 6H
HOJS
and then aftertreating the dyeing obtained with a mixture of cobaltous chloride and potassium bichromate.
9. Fibrous material of the group consisting of cellulose fibers and. mixtures of cellulose fibers with animal fibers dyed with a water-soluble azodyestufl by the process claimed in claim 1. l
10. Fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers dyed with a water-soluble azo-dyestuflf by the process claimed in claim 3.
11', Fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers dyed with a water-soluble a zodyestufi! by the process claimed in claim 5.
12. Fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers dyed with a water-soluble azodyestufi' by the process claimed in claim 7.
13. Fibrous material of the group consisting of cellulose fibers and mixtures of cellulose fibers with animal fibers dyed with a water-soluble azodyestuif by the process claimed in claim' 8.
. WERNER KIRST. ERICH FISCHER.
US367377A 1939-07-04 1940-11-27 Process of producing fast dyeings and the dyed fiber obtained thereby Expired - Lifetime US2277551A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2529444A (en) * 1947-12-03 1950-11-07 Gen Aniline & Film Corp Metalized ortho-hydroxy, ortho amino monoazo dyestuffs
US2539178A (en) * 1947-11-06 1951-01-23 Gen Aniline & Film Corp Metallized azo dyestuff and process of producing the same
US2583925A (en) * 1947-12-03 1952-01-29 Gen Aniline & Film Corp Metallized ortho-hydroxy, ortho amino monoazo dyestuffs
US2624653A (en) * 1947-12-03 1953-01-06 Gen Aniline & Film Corp Metallized ortho-hydroxy, orthoamino monoazo dyestuffs and their use in dyeing nylon

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2539178A (en) * 1947-11-06 1951-01-23 Gen Aniline & Film Corp Metallized azo dyestuff and process of producing the same
US2529444A (en) * 1947-12-03 1950-11-07 Gen Aniline & Film Corp Metalized ortho-hydroxy, ortho amino monoazo dyestuffs
US2583925A (en) * 1947-12-03 1952-01-29 Gen Aniline & Film Corp Metallized ortho-hydroxy, ortho amino monoazo dyestuffs
US2624653A (en) * 1947-12-03 1953-01-06 Gen Aniline & Film Corp Metallized ortho-hydroxy, orthoamino monoazo dyestuffs and their use in dyeing nylon

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