US2211149A - Process for the production of azo dyestuffs on the fiber - Google Patents
Process for the production of azo dyestuffs on the fiber Download PDFInfo
- Publication number
- US2211149A US2211149A US260338A US26033839A US2211149A US 2211149 A US2211149 A US 2211149A US 260338 A US260338 A US 260338A US 26033839 A US26033839 A US 26033839A US 2211149 A US2211149 A US 2211149A
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- Prior art keywords
- amino
- hydroxynaphthalene
- chlorobenzene
- red
- methyl
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- 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
- C09B39/00—Other azo dyes prepared by diazotising and coupling
Definitions
- Patented-Mala 1940 UNITED STATES PATENT OFFICE- Heinrich Mhrschei and Ludwig Niissler,.l.everkusen, Rhine, and
- Thepresent invention relates to a process of dyeing mixtures of wool and cellulosic fibers and to fibers dyed according to this process.
- aqueous solutions of weak alkalis for instance, of 10 go 8 mixed Ya consisting o 7 0 W001 alkali metal carbonates,- ammonia and similar d f aple fi e a o e for an hour compounds;
- the arylamides go from these soluaft M (3-, if d in the P n of W ttions uniformly on wool and regenerated cels agent in bath which o ta pe l ter $5 lulose.
- the weak alkalinity of the 5 8. 0 y p ne-ii' solutions practically no damage i d t th -carboylaminc)-diphenyl (dissolvedwith addition animal fiber of the mixture.
- the modification which comprises employing as coupling components 6 sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the aryiamide portion of which is derived from aromatic diamines and applying these components from a neutral to weakly alkaline bath.
- the modification which comprises employing as coupling com- 6 sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion of which is derived from bi-cyclic diamines and applyingv these components from a neutral to weakly alkaline bath.
- the modification which comprises employing as. coupling components 6 sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion of which being connected by one of the group consisting of the diphenyl linkage -0', CO-. CH2--, -NH-, CO.NH-- and HN.CO.NH and applying these components from a neutral to weakly alkaline bath.
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Description
Patented-Mala, 1940 UNITED STATES PATENT OFFICE- Heinrich Mhrschei and Ludwig Niissler,.l.everkusen, Rhine, and
Wolfgang Alt,
Hans Krzikalla and Ludwigshaien, Rhine, Germany,
assignors to General Aniline & Film Corporation, a. corporation of Delaware No Drawing. Application March '8,
No. 260,338. in Germany March 10 Claims.
Thepresent invention relates to a process of dyeing mixtures of wool and cellulosic fibers and to fibers dyed according to this process. t
It has been found that mixtures of wool and 1939, Serial mi.- e- -zei Example 1 10 g. of a mixed fabric consisting of ma, of wool and 30% of staple fiber are treated for one g hour at '35- 80" 0., if desired, in the presence of cellulosic fibers can be uniformly dyed b y apply a wetting agent, in a grounding bath, which ing to these mixtures arylamides of 6 sulio 2 t 1 4 f 4 dim mi by hydroxynaphthalene-3-carboxylic acid, which are 1 1 1 derived from aromatic diamines or polycyclic 5: gfl i g x p i y monoamines and developing them to azo dyestufis W a e o ,P um m with diazo compounds of aromatic amines on thecarbonate per 1 part naphtha and of m fibers thus pre treated sodium sulfate (bath ratio 1:20). After ground- Arylamides of the I'nentioned type are com ing the material is squeezed and developed in the densation products of ,6 su1fo 2 hymxynaph cold for 45 minutes with a diazo solution prethalene-S-earboxylio acid with, for instanceldiia? 5 a g 'i g t ted h f amino compounds of benzene and monoand e eve ope o yemg S I for a] 35 diammes of diphenyl diphemnether, dipheny1 an hour at -90 C. in the presence of a neutral amine, naphthalene,- fiuor ene, carbazole, dizigf or washing agent A yglowish red of phenyleneoxide, benzothiazoleand so on. g mess pmpemes is Obtain These arylamides of 6-sulfo-2-hydr0xynaph- Example 2 thalene-3-carboxyl1c acid are easily soluble in c w. aqueous solutions of weak alkalis, for instance, of 10 go 8 mixed Ya consisting o 7 0 W001 alkali metal carbonates,- ammonia and similar d f aple fi e a o e for an hour compounds; The arylamides go from these soluaft M (3-, if d in the P n of W ttions uniformly on wool and regenerated cels agent in bath which o ta pe l ter $5 lulose. On account of the weak alkalinity of the 5 8. 0 y p ne-ii' solutions practically no damage i d t th -carboylaminc)-diphenyl (dissolvedwith addition animal fiber of the mixture. The development of O S d um r fl fl n 20 of So um te dyestuffs on the fiber with diazotized aromatic (bath ratiolfifih Then the y issqueezed d amines is carried out in the usual way. By this developed 45 minutes in the 0016 w a m process dyeings of even shades ranging from (11820 S ut -QD pr p from Y 3o orange to black are obtained which-are distin- 5-chlorobenzene. The aftertreatme S t e guishecl in general bygood fastness to water, same as described in Example 1. A red of good rubbing and light. iastness properties lsobtained. I
- The followingv examples illustrate the invention In the following table; further dyeings obtainwithout, however, restricting it thereto. able inthe same way are arranged.
Azo component Diazo component Shade 4,4-dia": 1i -2"-h (nhthal aw ammgydiillllegyll y oxynap one 3 carboyl l-ainino-a-chlorobenzenel J Strongly yellowishred 40 Do 1-methyl-2-amino-4-chlorobenzene 1 0-.
1-methyl-2-amino-5-chlorobenzene Yell0wish red. D 0 ..l 2-amhio+chloro-diphenylethcr Do. 3,3-d1methoxy-4,4-d1;(6-sulfo-2"hydroxynaphthalene- .l-mothyl-z-aminol-chlorobenwne Strongly reddish brown. 3"-carboylamino)-diphenyl.,
Do 1-amino-2-chlorobenzena Reddish brown.
' 1-methyl-2-amino-4-nitrobenzene Fullred brown. i-amino-4-methory-diphenylamine. Black. a ht one. I t, l,id(6eulfo-2 hyd!oxynaphthalene-y-carboylaminoy l-metnoxy-z-amlnor'i-chlorobenwne.; Reddisli Bordeaux. 61126116. Do .1 '1-methoxy-2-amino-5-nitrobonzeno Brownishred bordeaux.
Do 4-ammo-4' 1nethoxy-dipnenylaniincm Black- 4 2-(6'-sulfo-2-hydroxynaphthalene-3'-carboylamino)- l-amino-z-chlorobenzenafli Scarlet. 50
naphthalene. f c Dc. A l-amlno-3-chlorobenzene .Do.
Do. l-methyl-2-amino-4-chlorobenzcne Red. 4o sg t-hydroxynsphthalene-3'-carboylamino)- 1-trifluoromethyl-3-amino-4-chlorobenmne Reddish orange. 1 1 )o l-omino-a-chlorobenzene Scarlet. 65 .Do... 1, :diethoxy-Zmnino-b-bencoylaminobenzene Reddish black.
' ponents Azo component Dluo component Shade 2-[4-(6-suiio-2-hydroxynaphthalene-3"-carboyl-trifluoromethyl-B-amlno-4-chlorobenzene Reddlsh orange.
lamino)-phenyl] o-methyl-benzothiazol.
Do l-methyl-Z-omino-B-chlorobenzene Scarlet. Dn l-methoxy-2-amino-4-chlorobenzene. Red. Do l-methoxy-Z-emlno-t-nitrobenaene. Strongly bluish red. Do 4-cmino-4-methoxy-diphenylamine m. Black. 2, 2'-dlchloro-4, 4'-dl-(6-sulio-2-hydroxynaphthalenel-amino-Zi-chlorobenzenc Strongly reddish orange.
3-carboylamlno)-diphenyl.
Do l-amino-Z-methyl-i-chlorobenzene Red. 4,4-di-(6-sulfo-2"-hydroxynaphthalene-3"-carboylamil-amino-2-methyl4l-chlorobenzene Yellowish scarlet.
no)-dlphenylmethane.
Do l-emino-2-methoxy-benzene-B-auliodiethylamide-.- Yellowish red. 3,3- ;li)(6"-suliifi;i2 -hydroxynaphthalenee carboylaml- I-amino-Z-methoxy-B-chlorobenzcne; Bluish red.
no enzan e.
Do l-amino-Z-methyl+chlorobenzene .L Strongly yellowish rod. 2,4'-dit-i(16'gsullo-z hydroxynaphthalene-3"-carboylamil-amino-2-methyl-4-chlorobenacne Do.
no p any o a-amino 4-methoxy-dlphenylamlne Greenish dark blue. 4,4'-di-(6-sulio-2"-hydroxynaphthalene-3"-carboylamil-amino-B-chlorobenzene Reddish orange.
no)diphenyl-3-sulronic acid. 4,44S1li,(6"-sugo-2"-hydroxynaphthalene-lW-carboylami- 1-emino-2,6-dichlorobenzene D- no enzop enone. 4,4'-di-(6"-sulio-2"-hydroxynaphthalene-.'i-carboylamil-eml'no-2-chlorobenzeno Do.
no)-diphenyl-ether.
Do l-amlno2-methoxy-4-nitrobenzene Brownian red. 2-nitro-4,4'-di-(6-sullo-2"-hydroxynaphthalene -3"- 4-amiuo-4-meth0xy-diphenylamine Bluish black.
carboylamino)-diphenyl.
Do l-emino-Z-methyl-lichlorobenzene Scarlet. 2,2'-dimethyl-4,4"-di-(6"sulio-2"-hydroxy-naphthalenel-amlnoQ-methyl-3-chlorobenzene Yellowish scarlet.
3"-carboylamino)-diphenyl-methane.
Do l-amino-2-methoxy-5-chlorobenzene Red. 2,2'-dichloro-4,4'-dl- 6-sullo-2"-hydroxynaphthalenel-amlno-2,5-dichloro-benmne Yellowish scarlet.
3"-carboylamlno) phenylmethane. Do l-amino-2-methyl-4-chlorobensene Red. 4,3-di-(6-sulio-2"-hydroxynaphtha1ene-3"-carboyl- 1-amlno-2-meth0xy-5-chlorobenzene Red bordeaux.
amino)-benzanilide.
o l-amino-2-chlorobenzene Yellowish scarlet. l-E6-sulio-2-hydroxynaphthalene-3-carboylamln0)'3- 1-amino-2,6-dichloro-benzene Orange.
b2: hydroxy 3 methyl 5 chlorobenzoylamino nzene. Do 1-amlno-2-methoxy-4-bcnzoylamino-5-mothyl-ben- Blulsh bordeeux.
zone. D0 4,4'-dlchlor0-2-aminodiphenylether Yellowish red.
We claim: is derived from bi-cyclic diamines the two nuclei 1. In-the process of producing azo dyestufis on mixtures consisting of wool-and regenerated cellulose by combining coupling components and diazo compounds on the fibers, the modification which comprises employing as coupling components 6 sulto-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion 01 which is derived from the group consisting of aromatic diamines and polycyclic monamines and applying these components from a neutral to weakly alkaline bath.
2. In the process of producing azo dyestuffs on mixtures consisting of wool and regenerated cellulose by combining coupling components and diazo compounds on the fibers, the modification which comprises employing as coupling components 6 sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the aryiamide portion of which is derived from aromatic diamines and applying these components from a neutral to weakly alkaline bath.
3. In the process of producing azo dyestuffs on mixtures consisting of wool and regenerated cellulose by combining coupling components and diazo compounds-on the fibers, the modification which comprises employing as coupling com- 6 sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion of which is derived from bi-cyclic diamines and applyingv these components from a neutral to weakly alkaline bath.
4. 'In the process of producing azo dyestuffs on mixtures consisting of wool and regenerated cellulose by combining coupling components and diazo compounds on the fibers, the modification .which comprises employing as. coupling components 6 sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion of which being connected by one of the group consisting of the diphenyl linkage -0', CO-. CH2--, -NH-, CO.NH-- and HN.CO.NH and applying these components from a neutral to weakly alkaline bath.
5. In the process of producing azo dyestufis on lulose by combining coupling components and diazo compounds on the fibers, the modification which comprises employing 2.2'-dichloro-4.4'-di- (6"-sulto-2' -hydroxynaphthalene 3"- carboylamino) -diphenyl-methane and applying the same from a neutral to weakly alkaline bath.
7. Mixtures consisting of wool and regenerated cellulose dyed according to a process as claimed in claim 1.
8. Mixtures consisting of wool and regenerated cellulose dyed according to a process as claimed in claim 4. I
9. Mixtures consisting of wool and regenerated cellulose dyed accordingto a process as claimed in claim 5. v
10. Mixtures consisting of wool and'regenerated cellulose dyed accord ns to a process as claimed in claim 6. I I
i HEINRICH MORSCI-IEL.
' LUDWIG Ntissnna.
HANS WOLFGANG ALT.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2211149X | 1938-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2211149A true US2211149A (en) | 1940-08-13 |
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ID=7990306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US260338A Expired - Lifetime US2211149A (en) | 1938-03-14 | 1939-03-07 | Process for the production of azo dyestuffs on the fiber |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2211149A (en) |
-
1939
- 1939-03-07 US US260338A patent/US2211149A/en not_active Expired - Lifetime
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