US1970661A - Azodyestuff and process of making same - Google Patents
Azodyestuff and process of making same Download PDFInfo
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- US1970661A US1970661A US472483A US47248330A US1970661A US 1970661 A US1970661 A US 1970661A US 472483 A US472483 A US 472483A US 47248330 A US47248330 A US 47248330A US 1970661 A US1970661 A US 1970661A
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- diazo
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- 238000000034 method Methods 0.000 title description 10
- 125000000217 alkyl group Chemical group 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 125000004104 aryloxy group Chemical group 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 150000001555 benzenes Chemical class 0.000 description 11
- 150000008049 diazo compounds Chemical class 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical class COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-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
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000025814 Inflammatory myopathy with abundant macrophages Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- -1 aromatic diazo compound Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003796 beauty Effects 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
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XRYSCSFJNUNNAU-UHFFFAOYSA-N n-chloro-n-phenylaniline Chemical compound C=1C=CC=CC=1N(Cl)C1=CC=CC=C1 XRYSCSFJNUNNAU-UHFFFAOYSA-N 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229960001407 sodium bicarbonate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 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
Definitions
- the new dyestuffs may be produced in substance, or on a fillerin order to prepare color lakes. They are of an especial importance for the production of ice colors. They yield when produced on the fiber brown shades which are of a particular value for the batic industry because of the beauty and brightness of these shades. According to the diazo-compounds used, the shades vary from the different brownsto brownish black and black.
- the arylamides used by the present process show so great an afiinity to the vegetable and animal fiber, that the goods padded therewith may be developed with diazo-compounds without being previously dried.
- Example- 1 Well boiled and dried cotton yarn is impregnated with a solution containing per liter 20 grs. of '3-hydroXy-diphenylaminel-carboxylic acid anilide, cc. of caustic soda solution of 34 Be.
- Example 4 Cotton yarn previously treated'in the appropriate manner is impregnated in a solution containing per liter 15 grs. of the beta-naphthylamide of 3-hydroxy-diphenylaminel-carboxylic acid, 30 cc. of caustic soda solution of 34 B. and 10 cc. of Turkey red oil. Then the goods are well wrung out and developed in a diazo solution neutralized with. sodium-bicarbonate and corresponding per liter 1 to 1.28 grs. of 3- chloro-aniline. Then they are rinsed and soaped at the boil.
- Example 7 Viscose silk is padded with the solution containing per liter 3 grs. of the para-nitranilide of 3 hydroxy 4'-chloro-diphenylamine-4-carboxylic acid, 4.5 cc. of caustic soda solution of 34 B. and 3 cc. of Turkey red oil; Then the material is squeezed off and developed with the diazo-solution neutralized with sodium acetate and containing per liter 2 grs. of l-amino-azobenzene. After working up in the usual maner a dark violet-red dyeing is obtained. The dyestuif thus produced on the fiber corresponds to the formula:
- Example 8 Acetate silk is impregnated with the solution containing per liter 0.5 gr. of 4-amino-azo-benzene and 1 cc. of hydrochloric acid of,20 B. After rinsing the material is treated in the customary manner in the bath of nitrite and hydrochloric acid. Then it is again rinsed and developed in a solution containing per liter 2 grs. of the ortho-anisidide of 3-hydroxy-4-chlorodiphenylamine 4-carboxylic acid and 2 cc. of caustic soda solution of 34 B. In this manner a full red dyeing is obtained.
- the dyestuff thus produced on the fiber corresponds to the formula:
- Example 9 Wool is impregnated with the solution containing per liter 3 grs. of the 2.5-dichloro-anilide of 3-hydroxy-4'-chloro diphenylaminei-carboxy I I he acid 4.5 cc of Caustic: soda Solution of 0 B' Diazocompound of Oomblmng component Shade obtalned 3 cc. of Turkey red oil and 50 grs. of common salt.
- the material is well squeezed and developed with g g i t z g blackish 8 m the diazo-solution neutralized with sodium-acey enzene 3,.;;?5.,,5;2fg car my F 80 t t d t i i per lit L62 grs. f 25.. 2-nitro-aniline; 3-hydroxy-4'-phenoxy-di- Yellowish brown.
- substituents 1 bemoyhmmo gg-ggg; fggzg i g gn D0 of this kind are, for instance, the sulionic acid and amino-5.5mmplienylszlmine-i-caribgxthe cerboxylic d group this oxy-benzene- Y ic-flci r i
- the structural formulae given for our new azobl r iline 3 h drox -'4-chloro-di- Yellowlshb n. 2 5 0 an i phgnyllgmineamrbok r dyestufis are correct to the best of our knowledge a gig;- pamphenetlc and belief.
- aniline (2 molecw 0mm diphenyl um be substituted by alkyl, alko: y, ary-o y or halogen. m proportions) in? 4 carboxylic 2.
- Process which comprises combining an arcgg g g 0% a g y matic diazo compound of the benzene series which M, e IX; f 4-chloro- 1Z-amincz- Bishl- (a -dhygrox31 4' Yellowish brown. may be substltuted y l, xy, ryl xy,
- boxylic acid ortho I V anisidide U OH 1 amino anthra 3 iihylgiroxy 4 methyl Fgll r eddish quinone. ip eny -amine-4-csrrown.
- X stands for alkyl, alkoxy or halogen andwherein the benzene nucleus 'III may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro.
- R stands for a radical of a mononuclear or polynuclear isocyclic aromatic compound
- benzene nucleus signified by I may be substituted by alkyl, alkoxy, aryloxy or halogen.
- benzene nucleus I may besubstituted by alkyl, alkoxy, aryloxy or halogen, the benzene nucleus III may be substituted by nitro, alkyl,
- 1,970,661 may be substituted by alkyl, 'alkoxy, aryloxy,ha1-
- alkoxy, aryloxy or halogen, and the benzene nucleus IV may be substituted by alkyl, alkoxy,
- X means alkyl, alkoxy or halogen and the nuclei III and. IV may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro, which com- 1 pounds yield when produced on a substratum brown shades.
- nuclei III andiIV may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro, which compounds yield when produced on a substratum brown shades.
- nucleus IV may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro, which compounds yield when produced on a substratum brown shades.
Description
Patented Aug. 21, 1934 UNITED STATES FYFICE PA NT 1,970,661- AZODYESTUFF AND PROCESS F .MAKING SAME . Leopold Laska and Arthur Zitscher, Oifenbachon-the-Main, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application August l, 1930, Serial No. 472,483. In Germany September 26, 1929 Claims. (01. 260-97) wherein the benzene nucleus signified by I and the aryl-radical may be substituted, only such components being used as do not contain any group rendering the dyestuffs soluble in water and alkalies, such as the 'sulfonic or carboxylic acid group. 1
The combining components used inthis process may be produced in the manner described in U. S. Patent No. 1,868,612.
The new dyestuffs may be produced in substance, or on a fillerin order to prepare color lakes. They are of an especial importance for the production of ice colors. They yield when produced on the fiber brown shades which are of a particular value for the batic industry because of the beauty and brightness of these shades. According to the diazo-compounds used, the shades vary from the different brownsto brownish black and black. The arylamides used by the present process show so great an afiinity to the vegetable and animal fiber, that the goods padded therewith may be developed with diazo-compounds without being previously dried.
In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees, but it is however to be understood, that our invention is not limited to the particular products or the reaction conditions mentioned therein.
Example- 1 Well boiled and dried cotton yarn is impregnated with a solution containing per liter 20 grs. of '3-hydroXy-diphenylaminel-carboxylic acid anilide, cc. of caustic soda solution of 34 Be.
and 20 cc. of Turkey red oil. Then it is well wrung obtained. {Ihe dyestuff' thus produced-on, the fiber corresponds to the. iormula:
Gaga-NE Example 2 OH OCH;
mQ aGWEG I Example 3 In order to'impregnate cotton with hydroxydiaryl-amine-carboxylic acid aryl-amides in a bath containing sodium chloride, one may work as follows:
4 grs. of the para-nitroariilide of 3-hydroxy- 4.-chloro-diphenylamine-4carboxylic acid, 10 cc/bi' Turkey red oil of 50% strength and 8 cc. of a caustic'soda solution of 34 B. are made to a paste. This paste is warmed slightly a'nddise solved while boiling with the addition of 20cc. of hot soft water. By the admixture of cold water the mass is made up to '1000 cc. and then mixed with 10 grs. of common salt. In this solution the material to be dyed is impregnated at 30"for 30 mirutes. Then the paddedand dehydrated material is developed by agitating it for half an hour in a diazo solution.
Example 4 Cotton yarn previously treated'in the appropriate manner is impregnated in a solution containing per liter 15 grs. of the beta-naphthylamide of 3-hydroxy-diphenylaminel-carboxylic acid, 30 cc. of caustic soda solution of 34 B. and 10 cc. of Turkey red oil. Then the goods are well wrung out and developed in a diazo solution neutralized with. sodium-bicarbonate and corresponding per liter 1 to 1.28 grs. of 3- chloro-aniline. Then they are rinsed and soaped at the boil.
In this manner a full dark brown dyeing is obtained. The dyestufl thus produced on the fiber corresponds to the formula:
V t. Example 5 Well boiled and dried cotton yarn is impregnated with a solution containing per liter 10 grs. of the dianisidide of 3-hydroXy-diphenylamine--carboxylic acid, 15 cc. of caustic soda solution of 34 B. and 10 cc.Turkey red oil. Then it is dehydrated well and developed with the A diazo solution neutralized with sodium acetate and containing per liter 1.52 grs. of 5-nitro-2- amino-l-methyl-benzene. It is then rinsed andsoaped at the boil. In this manner a dark brown dyeing is obtained. The dyestuff thus produced on the fiber corresponds to the formula:
is made up to 1 liter liquor.
- Q Degummed spun silk is padded in, this solution, squeezed offand developed with the diazo-solurtion neutralized with sodium acetate and containing per liter 1.62 grs. of 2.5-dichloro-aniline with the addition of a small amount of acetic acid. After rinsing, acidifying and hot soaping a full yellowish brown dyeing is obtained. The dyestuff thus produced on the fiber corresponds to the formula:
By starting with the para-nitranilide of 3- hydroxy 4' chloro diphenylamine 4 car boxylic acid and with the same diazo-compound a dark yellowish brown dyeing is obtained, While with the 2.5-dichloro-anilide an olive-brown dyeing is obtained. Whenthe diazo-compound is replaced by diazotized Q-amino-azo-benzene and the same arylamides are used, claret red shades are obtained.
Example 7 Viscose silk is padded with the solution containing per liter 3 grs. of the para-nitranilide of 3 hydroxy 4'-chloro-diphenylamine-4-carboxylic acid, 4.5 cc. of caustic soda solution of 34 B. and 3 cc. of Turkey red oil; Then the material is squeezed off and developed with the diazo-solution neutralized with sodium acetate and containing per liter 2 grs. of l-amino-azobenzene. After working up in the usual maner a dark violet-red dyeing is obtained. The dyestuif thus produced on the fiber corresponds to the formula:
In the same manner a claret red dyeing is obtained by replacing the para-nitranilide by the corresponding ortho-anisidide.
Example 8 Acetate silk is impregnated with the solution containing per liter 0.5 gr. of 4-amino-azo-benzene and 1 cc. of hydrochloric acid of,20 B. After rinsing the material is treated in the customary manner in the bath of nitrite and hydrochloric acid. Then it is again rinsed and developed in a solution containing per liter 2 grs. of the ortho-anisidide of 3-hydroxy-4-chlorodiphenylamine 4-carboxylic acid and 2 cc. of caustic soda solution of 34 B. In this manner a full red dyeing is obtained. The dyestuff thus produced on the fiber corresponds to the formula:
By replacing the ortho-anisidide by the corresponding 2-5-dichloro-anilide and working otherwise in-the same way a brown dyeing is obtained.
Example 9 Wool is impregnated with the solution containing per liter 3 grs. of the 2.5-dichloro-anilide of 3-hydroxy-4'-chloro diphenylaminei-carboxy I I he acid 4.5 cc of Caustic: soda Solution of 0 B' Diazocompound of Oomblmng component Shade obtalned 3 cc. of Turkey red oil and 50 grs. of common salt. The material is well squeezed and developed with g g i t z g blackish 8 m the diazo-solution neutralized with sodium-acey enzene 3,.;;?5.,,5;2fg car my F 80 t t d t i i per lit L62 grs. f 25.. 2-nitro-aniline; 3-hydroxy-4'-phenoxy-di- Yellowish brown.
phenylamine-4-carboxyldlchloro-anihne. Thereafter it is rinsed and macid.pam nitm.am1ide, soaped as usual. In this manner a brown dye- Z' 1 & Black- 7 0x -amn -a mg'isobtamed. The dyestuff thus produced on g 1 M0 3,333,5 5, 5 OXY n th fib corresponds t th f l 4-amino-3.2-d1meth- 3-hydroxy-2-methy1-5- Reddishbrown. 8,5
' yl-azo-benzenc. chloro-diphenylaminei- O H 01 carboxylic-acid para-nitro-anilide.
, 1 benzoylamino 4 3 -hydroxy- 3' -methyl -4 Violet-brown. g NH. ammo 2.5 diethchloro-diphenyl amineoxy-benzenc. 41;]carbozxy1ict-h acid g5- C1 0 010- -me oxy-p 8- i 1 1 nyl) -amide. (9U) l-amino-anthraquin- 3 hydroxy 3 methyl 4- Brown. N:N one. methoxy diphenylamine-4-carboxylic-acidpara-nitro-anilido.
01 v The following table shows the shades of some Since an object of the present invention is to other dyestuffs of this series: provide dyestuffs of good. fastness properties,
which dyestuffs are insoluble in water and alka- Diazocompound of Combining component Shade obtained 1t 15 to be understood that j aromatlc numel of the general formula appearing 11). the appended claims do not contain any substituents which are 11m '1' ls-11d -4-hl -d'- alchmoamme .Z Bmwn known to render organic compounds soluble in y acideorthotoluididewater or alkalies and to tend to depreciate the -2- a-ndi -4-11 -d'- d'- i 4 filt at -at??? Z f$nnei3 3 Re bmwn fastness of the dyestuffs to alkalies. substituents 1 bemoyhmmo gg-ggg; fggzg i g gn D0 of this kind are, for instance, the sulionic acid and amino-5.5mmplienylszlmine-i-caribgxthe cerboxylic d group this oxy-benzene- Y ic-flci r i The structural formulae given for our new azobl r iline 3 h drox -'4-chloro-di- Yellowlshb n. 2 5 0 an i phgnyllgmineamrbok r dyestufis are correct to the best of our knowledge a gig;- pamphenetlc and belief. However, it has not yet been possible 1. Brown to definitely determine the exact structure of g gg i n g g g these new a-zo-dyestuffs. For example, it is conw gf p p ceivable that the azo group is attached toithe 4-amino ll-megh- 3-hgdro1xy-4 -chl2ro-di- Reddish brown. phenyl nucleus II in ortho-position to the hyi 16H en -am1ne- -(31X' 323 I y goxyfleacidmawchlow droxyl group instead of 111 para-posit1on as indianilide. cated in the structural formula given 'Conse '1' -hd -4'-h1 -d'- 1 h (110mm 3 ii en y i amin car Yelowls brown quently we wish it understood that when such 15 g g aeid para I structural formulae are employed in the appended Reddish brown claims, they are intended to define the new azod i men ec i er, Darklet dyestuiifs which we have described and which may i f be obtained in accordance with our disclosure. Meta dichloro Reddishbrown. We claim: 6 g benzidine. a Brown 1. Process which comprises combining an aro- 321518.; m 0 am 7 Y 11 brown matic diazo compound of the benzene or anthra- 9 quinone series, with a 3-hydroXy-diphenylamine- 4' nitro 2.5 di 3- y yf oro- Vio et-b ac v l-carboxylic-acid-aryl-amide of the formula:
methoxy -4 ami phenyl amine 4 car V f no-azo-bcnzene boxylic acid (4 OH 7 25 chloro 2 methoxy t a l d 111 4 a il i hl 6 Y 11 hb V i 2.5 ic or'o y roxyoroie owis rown.
amino-l-toluene. phenyl amine -4 car I NH C0-NH.R
boxylic acid -ace11aph thyl-amide 4-ch1oro-2-amino- 3-hydroxy-4 -chloro-di- Brown. 7 wherein R stands for a radical of a mono-nuclear we diphenyl-etherfix ng-2 3 39;? :5: V V or polynuclear isocyclic aromatic compound and thraquinonyl-amide. wherein the benzene nucleus signified by I may 2 -chl0ro -4-nitro Bis (3 hydroxy 4' Deep brown. f
aniline (2 molecw 0mm diphenyl um be substituted by alkyl, alko: y, ary-o y or halogen. m proportions) in? 4 carboxylic 2. Process which comprises combining an arcgg g g 0% a g y matic diazo compound of the benzene series which M, e IX; f 4-chloro- 1Z-amincz- Bishl- (a -dhygrox31 4' Yellowish brown. may be substltuted y l, xy, ryl xy,
dipheny -ether 2 0 etc ip eny am a m molecular proporine-4-carboxylicacid)- yla arylamln? nltlo groups 0r 1131.0 gen tions). (2.5 dichloro phenyl) atoms, or a further diazo or an azo group, with a 1.4-diamide. v -h ro h. 1' e- 5 -nitro-2-amin0- -3-hydroxy-2-chloro-di- Reddishbrown. 3 yd F W 4 carboxyhc acid 1 methoxy ben Imam. mine. 4 car alYl-Etflllde of the foimula. zcne. boxylic acid ortho I V anisidide. U OH 1 amino anthra 3 iihylgiroxy 4 methyl Fgll r eddish quinone. ip eny -amine-4-csrrown.
boxylic acid ortho M @NH I I Q0.NH@ anisidide.
, 2.4,5- trichloro -ani- 3 hydroxy 2; methyl Yellowish brown. I p a gggfi i-gga figg wherein the benzene'nucleus I may be substituted naphthglidg, by alkyl, a1kcxy,.aryloxy or halogen and the ben- "3 zene nucleus III may be substituted by nitroalkyl phenylamme-4-carboxylv r l icacid-betanaphthalide. alkoxy, aryloxyor a n. gg' g gg g zi ?gg g Reddlshbrqwn- 3. Process which comprises combining an aroi ci nmd matic diazo compoundof the benzene series which T1501 may contain alkyl, alkoxy, aryloxy or nitroogen or nitro, with a 3-hydroXy-diphenylamine4- carboxylic acid arylamide of the formula:
wherein X stands for alkyl, alkoxy or halogen andwherein the benzene nucleus 'III may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro.
5. Process which comprises combining an arcmatic diazo-compound of the benzene series which groups or halogen-atoms, with a 4f-chloro-3- hydroXy-diphenyL-amine 4 carboxylic acid-nitranilide of the formula:
on I
6. Process which comprises combining an arcmatic diazo-compound of the benzene series which i may contain alkyl, alkoxy, aryloxy or nitrogroups or halogen-atoms, with a 4-chloro-3- hydroxy diphenyl amine 4 carboxylic acidpara-nitranilide of the formula:
'7. Process which comprises combining the diazocompound of 2-5-dichloro-aniline with lchloro-3-hydroXy-dipheny1 amine--carboxylicacid-para-nitranilide of the formula:
8. The 'azo dyestuffs which are obtainable by combining an aromatic diazo compound of the benzene or anthraquinone series with a 3-hydroxydiphenylamine carboxylic acid-arylamide of the formula:
wherein R stands for a radical of a mononuclear or polynuclear isocyclic aromatic compound, and
wherein the benzene nucleus signified by I may be substituted by alkyl, alkoxy, aryloxy or halogen.
9. The azo dyestuffs of the general formula:
wherein the benzene nucleus I may besubstituted by alkyl, alkoxy, aryloxy or halogen, the benzene nucleus III may be substituted by nitro, alkyl,
1,970,661: may be substituted by alkyl, 'alkoxy, aryloxy,ha1-
alkoxy, aryloxy or halogen, and the benzene nucleus IV may be substituted by alkyl, alkoxy,
' aryloxy, acylamino, arylamino, nitro groups or halogen atoms ora further diazo or an azo group.
10. The azo-dyestufis of the general formula:
wherein X means alkyl, alkoxy or halogen and the nuclei III and. IV may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro, which com- 1 pounds yield when produced on a substratum brown shades.
11. The azo-dyestuffs of the general formula:
wherein the nuclei III andiIV may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro, which compounds yield when produced on a substratum brown shades.
12. The azo-dyestulfs of the general formula:
wherein the nucleus IV may be substituted by alkyl, alkoxy, aryloxy, halogen or nitro, which compounds yield when produced on a substratum brown shades. r
13, The azo -dyestuffs of the general formula:
. OH G G Q wherein the nucleus IV may be substituted by alkyl, alkoxy', aryloxy, halogen or nitro,- which compounds yield when produced on a substratum brown shades. 14. The azo-dyestuff of the formula:
whichcompound yields when produced on a substratum yellowish brown shades.-
15. The azordyestufi? of the formula:.
- I-w c] which compound yields when produced on a substratum brown shades.
16. The azo-dyestufi of the formula:
OH 0 CH3 i O N which compound yields when produced on a substratum full reddish-brown shades.
17. Fiber dyed by means of the azodyestuffs claimed in claim 8.
of the of the azodyestuffs of the azodyestuffs of the azodyestuffs of the azodyestufis LEOPOLD LASKA. ARTHUR ZITSCHER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1970661X | 1929-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1970661A true US1970661A (en) | 1934-08-21 |
Family
ID=7820865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US472483A Expired - Lifetime US1970661A (en) | 1929-09-26 | 1930-08-01 | Azodyestuff and process of making same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1970661A (en) |
-
1930
- 1930-08-01 US US472483A patent/US1970661A/en not_active Expired - Lifetime
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