US2117426A - Azo dyes - Google Patents
Azo dyes Download PDFInfo
- Publication number
- US2117426A US2117426A US155042A US15504237A US2117426A US 2117426 A US2117426 A US 2117426A US 155042 A US155042 A US 155042A US 15504237 A US15504237 A US 15504237A US 2117426 A US2117426 A US 2117426A
- Authority
- US
- United States
- Prior art keywords
- amino
- acid
- benzidine
- group
- pab
- 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 - Lifetime
Links
- 239000000987 azo dye Substances 0.000 title description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- GMJHZZCVWDJKFB-UHFFFAOYSA-N 4-(4-aminophenyl)benzene-1,3-diamine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1N GMJHZZCVWDJKFB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 229950011260 betanaphthol Drugs 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 5
- 235000010980 cellulose Nutrition 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000001302 tertiary amino group Chemical group 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ILCCKGWFMOINFU-UHFFFAOYSA-L dipotassium;7-aminonaphthalene-1,3-disulfonate Chemical compound [K+].[K+].C1=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=CC(N)=CC=C21 ILCCKGWFMOINFU-UHFFFAOYSA-L 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
Definitions
- This invention relates to azo dyes. Particularly the invention relates to a method of applying compounds of the type described in Jordan et a1.
- aryl has a single nucleus from the group consisting of benzene and naphthalene, coupling it to, preferably, beta naphthol, or to other azo dyestufi coupling components.
- Example I The objects lgif the inventionare accomplished, Five tenths t of cotton piece goods are generally dlazoflzmg the compound dyed in the usual manner, known to those skilled represented Y the in the art, with ten hundredths part of 3 4-amino-azobenzene-4-sodium-sulfonate+ l5 NHOG- 2-amino-benzidine (PAB)3
- PAB 4-amino-azobenzene-4-sodium-sulfonate+ l5 NHOG- 2-amino-benzidine (PAB)3
- PAB 2-amino-benzidine
- the dyed fabric is rinsed in cold water and put in 200 parts of water at 20 C. Add three tenths part of sodium nitrite and four tenths part of sulfuric acid. Stir minutes. Rinse with cold Nm water.
- zidine when dyed on the fiber and developed with beta-naphthol, as in Example II above, gives a brown shade dyeing.
- the probable formula of the dyestuff on the fiber is:
- Iglfi-fulfonic acid Z-amino-benzidine 2. 8 Sulfanilic acid Z-amlno-5-hydroxy-naphtha- Mete-tolylene diamine Red brown. lg iggsulfonic acid 2-amino-benzidine a. 9 4-Amino-azobenzene-4-sodium-sulfonate 2- Beta-naphthol Red orange.
- PAB amino-benzidine
- PAB amino-benzidine
- PAB amino-benzidine
- cresidine 2-amino-benzidine PAB:4.
- 14 Sulfauilic acid 2-amino-benzidine PABh. Brown.
- PAB toluidine meta-toluidine Zaminobenzidine
- PAB (pata-amino-benzoyl).
- a rylN N and v Y Y
- aryl has a single nucleus from the group consisting of benzene and naphthalene, and coupling it with a compound from the group consisting of beta-naphthol, meta-tolylene-diamine, 1-phenyl-3-methyl-5-pyrazolone, and acetoacetaniline.
- NBC 0 in which X is one of a group consisting of hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented May 17, 1938 AZO PATENT OFFICE DYES Henry Jordan and Swanie S. Rossander, Wilmington, Del., assignors to E. I. du Pont de Nemours & Company, poration of Delaware Wilmington, DeL, a cor- No Drawing. Application July 22, 1937, Serial No. 155,042
6 Claims.
This invention relates to azo dyes. Particularly the invention relates to a method of applying compounds of the type described in Jordan et a1. application for Azo dyes, filed of even date herewith, Serial #155,041 to cellulose, within which term is meant the celluloses and regenerated cellulose.
It is an object of the invention to produce new dyes which have exceptional fastness to washing.
amino, tertiary amino, carboxy, and sulfonic acid, and aryl has a single nucleus from the group consisting of benzene and naphthalene, coupling it to, preferably, beta naphthol, or to other azo dyestufi coupling components.
The following examples illustrate but do not limit the invention. In these examples parts are by weight.
Example I l The objects lgif the inventionare accomplished, Five tenths t of cotton piece goods are generally dlazoflzmg the compound dyed in the usual manner, known to those skilled represented Y the in the art, with ten hundredths part of 3 4-amino-azobenzene-4-sodium-sulfonate+ l5 NHOG- 2-amino-benzidine (PAB)3 The dyed fabric is rinsed in cold water and put in 200 parts of water at 20 C. Add three tenths part of sodium nitrite and four tenths part of sulfuric acid. Stir minutes. Rinse with cold Nm water. Dissolve one tenth part of beta-naphthol NHOO 5 in 200 parts of water and one twentieth part of caustic soda. Stir the solution rapidly while Ary =N adding the above rinsed piece goods. Stir 15 I minutes. Rinse in cold water and dry. The 3 dyeing is a red orange shade. The probable formula of the dye on the fiber is:
-NHo0-C N= NaOaS -N== C N=N Hoin wh1ch X is one of a group consisting of hydro- E p I gen i Aryl-N=N 50 and Y is at least one of a group consisting of hydro- 55 gen, halogen, alkyl, alkoxy, hydroxy, secondary Five tenths part of cotton piece goods is dyed in the usual manner, known to those skilled in the art, with ten hundredths part of metanilic acid 1,6-Cleves acid- Z-amino-benzidine (PAB)2 The dyed fabric is rinsed in cold water and put in 200 parts of water at 20 C. Add three tenths part of sodium nitrite and four tenths part of sulfuric acid. Stir 15 minutes. Rinse with cold water. Dissolve one tenth part of beta-naphthol in 200 parts of water and one twentieth part of caustic soda. Stir the solution rapidly while S OaNaadding the above rinsed piece goods. Stir 15 minutes. Rinse in cold Water and dry. The dyeing is a brown shade. The probable formula of the dye on the fiber is:
zidine (PAB): when dyed on the fiber and developed with beta-naphthol, as in Example II above, gives a brown shade dyeing. The probable formula of the dyestuff on the fiber is:
N H c o N [I N v I Ezcample IV The dye amino G salt meta-toluidine meta toluidine 2-amino-benzidine (PAB): is dyed on the fiber per procedure of Example I or II above.
S OzNa Example III The dye amino G salt aniline-+2-amino-ben- OH OH It gives a yellow brown shade dyeing. The probable formula of the dye on the fiber is:
SO5Na CH (EH3 trating the invention:
tively little use.
Shade on Ex. Diazo component Coupling component cellulose SuJIanilic acid- 2-amino-5-hydroxy-naphtha- Beta-naphthol Red brown.
l eig-lgsulfonic acid 2-amino-benzidine s- 6 Sulfanilic acid- 2ramino-5-hydroxy-naphtha- 1-phenyl-3-methylfi-pyrazo- Yellow brown.
1(61;1Xil3-)Sl1lf0ni0 acid Z-amino-benzidine lone.
a. 7 Sulfanilic acid Z-amino-5-hydroxy-naphtha- Acetoaoet-anilide Do.
Iglfi-fulfonic acid Z-amino-benzidine 2. 8 Sulfanilic acid Z-amlno-5-hydroxy-naphtha- Mete-tolylene diamine Red brown. lg iggsulfonic acid 2-amino-benzidine a. 9 4-Amino-azobenzene-4-sodium-sulfonate 2- Beta-naphthol Red orange.
amino-benzidine (PAB)3. 10 Z-Naphthylamine-fi, S-disulfonio acid 2- do Bordeaux.
amino-benzidine (PAB)a. 11 2'Napht11y1amine-6, 8-disulfonicacid)cresid- Brown.
ine Z-amino-benzidine (PABh. 12 Metanilic acid 1, 6-Cleves acid 2- Do.
amino-benzidine (PAB);. 13 8-A1m'no-l-naphthol-3, fi-disulfonic acid -z Violet.
cresidine 2-amino-benzidine (PAB):4. 14 Sulfauilic acid 2-amino-benzidine (PABh. Brown. 15 Z-Naphthylamine-fi, 8-disulfonio acid ani- Do.
line 2-amino-benzidine (PABh. 16 Z-Naphthylamine-G, 8-disulfonic acid meta- Yellow brown.
toluidine meta-toluidine Zaminobenzidine (PAB)3.
In the above table (PAB) stands for (pata-amino-benzoyl).
used.
To be of greatest advantage the products of this invention should be produced on the fiber, other- SOzNa SOINE S OaNa We claim:
NHCO
wise their insolubility renders them of compara- As many apparently widely different embodimentsof this invention may be made without departing from the spirit and scope thereof, it is to be understood that we do not limit ourselves to the specific embodiments thereof except as defined in the appended claims.
1. A compound represented by the formula:
3. A compound represented by the formula:
in which X is one of a group consisting of hydrogen,
A rylN=N and v Y Y A ry1N=NA ry1 N=N Y is at least one of a group consisting of hydrogen, halogen, alkyl, alkoxy, hydroxy, secondary amino, tertiary amino, carboxy, and sulfonic acid, and aryl has a single nucleus from the group consisting of benzene and naphthalene.
5. The process which comprises diazotizing a compound represente'dby the formula:
in which X is one of a group consisting of hydrogen,
Aryl-N=NArylN=N- Y is at least one of a group consisting of hydrogen, halogen, alkyl, alkoxy, hydroxy, secondary amino, tertiary amino, carboxy, and sulfonic acid,
7 and and aryl has a single nucleus from the group consisting of benzene and naphthalene, and coupling it with a compound from the group consisting of beta-naphthol, meta-tolylene-diamine, 1-phenyl-3-methyl-5-pyrazolone, and acetoacetaniline.
6. Cellulose dyed with the product produced by impregnating the cellulose with the compound represented by the formula:
NHa
NBC 0 in which X is one of a group consisting of hydrogen,
A ry1N==N- Y Y A ry1-N=NA 1ylN=N Y is at least one of a group consisting of hydrogen, halogen, alkyl, alkoxy, hydroxy, secondary amino, tertiary amino, carboxy, and sulfonic acid, and aryl has a single nucleus from the group consisting of benzene and naphthalene, diazotizing it on the fiber, and coupling it to one of a group of compounds consisting of beta-naphthol, metatolylene diamine, 1-pheny1-3-methyl-5-pyrazolone, and acetoacet-anilide.
HENRY JORDAN. SWANLE S. ROSSANDER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US155042A US2117426A (en) | 1937-07-22 | 1937-07-22 | Azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US155042A US2117426A (en) | 1937-07-22 | 1937-07-22 | Azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2117426A true US2117426A (en) | 1938-05-17 |
Family
ID=22553900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US155042A Expired - Lifetime US2117426A (en) | 1937-07-22 | 1937-07-22 | Azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2117426A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969339A (en) * | 1972-09-14 | 1976-07-13 | Produits Chimiques Ugine Kuhlmann | Water-soluble pentakis-azo dyestuffs derived from 4,4'-diaminoazobenzene |
-
1937
- 1937-07-22 US US155042A patent/US2117426A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969339A (en) * | 1972-09-14 | 1976-07-13 | Produits Chimiques Ugine Kuhlmann | Water-soluble pentakis-azo dyestuffs derived from 4,4'-diaminoazobenzene |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2082156A (en) | Azo dyestuffs | |
| US2170262A (en) | Derivatives of dyestuffs containing hydroxyl groups and process of making same | |
| US2673201A (en) | Cobaltiferous azo-dyestuffs | |
| US2245971A (en) | Azo dyestuffs | |
| GB197809A (en) | Improvements in the preparation of azo compounds | |
| US2117426A (en) | Azo dyes | |
| US2192153A (en) | Azo dyestuffs | |
| US2159542A (en) | Azo dyestuffs | |
| US2154981A (en) | Dyestuffs containing simultaneously radicals of anthraquinone dyestuffs and azo dyestuffs and process of making the same | |
| US2228416A (en) | Azo dyes | |
| US2195089A (en) | Polyazo dyestuffs | |
| US2178757A (en) | Azo dyes | |
| US2160448A (en) | Metal azo dyestuffs and a process for their manufacture | |
| US2633462A (en) | Complex copper compounds of disazo | |
| US2191801A (en) | Polyazo dye compounds | |
| US2103804A (en) | Azo dyestuffs and process for their manufacture | |
| US2157876A (en) | Polyazo dyestuffs | |
| US2275124A (en) | Azo dye | |
| US2155685A (en) | Azo dyes | |
| US2027897A (en) | Azo-dyestuff | |
| US2362548A (en) | Trisazo dyestuffs | |
| US1951815A (en) | Azo-dyestuffs insoluble in water and fiber dyed therewith | |
| US2137810A (en) | Direct dyes, process, and product | |
| US1579121A (en) | Producing fast dyeings on wool | |
| USRE21476E (en) | Naoss |