CA1038863A - Water-soluble diazo dyestuffs derived from 4,4'-diamino-benzanilide - Google Patents
Water-soluble diazo dyestuffs derived from 4,4'-diamino-benzanilideInfo
- Publication number
- CA1038863A CA1038863A CA218,885A CA218885A CA1038863A CA 1038863 A CA1038863 A CA 1038863A CA 218885 A CA218885 A CA 218885A CA 1038863 A CA1038863 A CA 1038863A
- Authority
- CA
- Canada
- Prior art keywords
- parts
- water
- benzanilide
- diamino
- acid
- 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
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 2
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 title 1
- 239000000835 fiber Substances 0.000 abstract description 5
- 238000004043 dyeing Methods 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- -1 amino- Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
- C09B35/32—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O— from two different coupling components
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE:
Sulfonated azo dyestuffs of the formula wherein A is , or
Sulfonated azo dyestuffs of the formula wherein A is , or
Description
~C~38~363 ~ he present invention relates to a new class of æulfonated azo dyestuffs which are well suited for the direot dyeing of co-tton and other cellulosic fibers such as linen~
regenerated cellulose fibers, hemp and the llke~
~he invention provides a new class of water-soluble diazo dyestu~fs of the formula:
~2 ~ - N = ~ ~ - CO ~,3~
1 ~1/~
SO~H
wherein A is OH
~ NO ~ s03H H
(see ~extbook of Org. Chemistry by G.H. Richter pages 520-527 and 531)~
~hese dyestuffs have characteristics which are similar to those of the conventional direct dyestuffs of the benzidine ~eries~ but the process for their manufacture does not involve any toxicological risks. Actually, benzidine and its deriva-tives~ which are used in preparing conventional dyestuffs ha~ing charac-teristics which are similar to those accord-ing to the invention~ are hazardous substnnces, i.e., they are carcino-genio~ and conseguently the use and preparation thereof are extremely harmful to personnel handling them.
~ hese dye~ can be prepared by tetrazotization of ~94~-diamino-benzanilide followed by acid coupling of the tetraazo derivative with 2-amino-8-naphthol-6-sulfonic acid, a~ter which it is further coupled in a substantiall~ alkaline medium with the selected coupling agent A, that i9~ with H
. ' ' '' ' ~''"~.i ~38~63 acid or 5-naphthol-4-amino-2,7-disulphonic acid, phenol~ or
regenerated cellulose fibers, hemp and the llke~
~he invention provides a new class of water-soluble diazo dyestu~fs of the formula:
~2 ~ - N = ~ ~ - CO ~,3~
1 ~1/~
SO~H
wherein A is OH
~ NO ~ s03H H
(see ~extbook of Org. Chemistry by G.H. Richter pages 520-527 and 531)~
~hese dyestuffs have characteristics which are similar to those of the conventional direct dyestuffs of the benzidine ~eries~ but the process for their manufacture does not involve any toxicological risks. Actually, benzidine and its deriva-tives~ which are used in preparing conventional dyestuffs ha~ing charac-teristics which are similar to those accord-ing to the invention~ are hazardous substnnces, i.e., they are carcino-genio~ and conseguently the use and preparation thereof are extremely harmful to personnel handling them.
~ hese dye~ can be prepared by tetrazotization of ~94~-diamino-benzanilide followed by acid coupling of the tetraazo derivative with 2-amino-8-naphthol-6-sulfonic acid, a~ter which it is further coupled in a substantiall~ alkaline medium with the selected coupling agent A, that i9~ with H
. ' ' '' ' ~''"~.i ~38~63 acid or 5-naphthol-4-amino-2,7-disulphonic acid, phenol~ or
2-amino-5-naphthol-7-sulfonio acid according to conventional techni~ues.
These dyestuffs dye cellulosic fibers in dark shades ranging ~rom violet to red.
Dyeing of fibers with the dyestuffs of the in~entlon is carried out using the same methods as are used with conventional direct dyestuffs, i.e., at a temperature ordinarily ranging from 50 to 100C from a water-bath containing adequate quantities e.gO from 0,01 g to 2-3g% about or according to the user~s exi-gence of dyestuffs and from 5 to 20% (with respect to the weight o~ the fiber) of anhydrous Na2SO~ or NaClO
~he following example~ are gi~en to illus-trate the invention~ all parts being understood as par-t~ by weight unless otherwise indicated.
~ 1 22.7 part~ of 4-4~-diamino-benzanilide suspended in 50 parts of water and 52 parts of 20 Bé hydroohloric acid were tetrazotized, after cooling with 150 parts of ice, by adding dropwise, at 0-5C over a period of 30 minutes~ a solution of 14 parts o~ NaN02 in 60 parts of H20- After 60 minutes stixring~
the exoess nitrous acid was remoYed using sulfamic acidO ~he resulting mass was neutrali~ed to weak Congo Red with 7 parts of calcium carbonateO The tetrazotization mass was poured over a few minutes onto a mass of 24 partæ of 2-amino-8-naphthol-6-sulfonic acid dissolved in 100 parts o~ water and 13,~ parts of 36 Bé NaOH and reprecipitated ~t a pH of 3.5 wi-th 28 parts of 20 Be ~Cl.
The coupling mass ~as kept at a pH of 305 for about 3o 4 hours with 30 parts of sodium acetate. 3 H20 at a temperature of 0-5C~ ~he pH was raised to 7.5 with 16 parts of ~a2C03 in the form of a 20~ solution (w/v).
16~3~3~363 The solu-tion was then added to 32 parts of H acid as previously defined dissolved in 1QO parts of water and 13.3 par-ts o~ 36 Bé NaOH brought to a pH of 8.5-9 with 10 parts of Ma2C03 and cooled to O-5C with 100 parts of ioeO
~he coupling mass was kept urlder stirring over night, while keeping the pH at 8.5-9 with smal]. additions of ~a2C~.
The following morning, the whole mass was heated to 60C for 4 hours and salted with 110 parts of roc~-salt.
The whole was filtered under Yacuum and completely squeezed dry.
The product was dried at 70~80C for 24 hours. ~his product dyes cellulose fibers in a violet shade with fair uni-~ormity and fa~tnessO
EXA~PIE 2 22.7 parts of 4~4~-diamino benzanilide were tetra-zotized as described in ~xample 1, after which the excess ni-trous acid V~9 removed with sulfamic acid.
~he tetrazotized mass was added, over a period of 40 minute~ to a solution o~ 22.8 parts of 2-amino-8-naphthol-6-~ulfonic acid dissolved in 125 parts of H20 and 13.3 parts of 36 Bé ~aOHO
~he whole mass was kept under sitrring over night at a pH of 1.8-2. It was then cooled to about 100a with 100 parts of ice and the solution was added~ in the form o~ a ~ine stream to 9.4 parts o~ phenol in 50 parts of water and 13.~ parts of 36 ~é ~aO~. ~he mass was kept under stirring for 2 hours at a pH of 9-9.5 and at a temperature of about 15Co At the end of the coupling~ the whole was acidified to light Congo red with 35 parts of 20 Bé HCl. ~he precipitated dyestuff was filtered under vacuum and completely dried off.
It was dried at 95C.
, ~ 1)3~3863 The obtained product dyes cellulose fibers in a yellowish red shade and fair fastness to moisture and light.
E ~
2207 parts of 4-4~-diamino-benzanilide were tetra zotized as described in Example 1 and the coupling with 2 amino-; 8-naphthol-6-sulfonio acid waæ carried out as described in ~xample 2. At the e~d of the couplingS the diazomonoazoic ma~s was added w~th 22.6 parts of 2-amino-5-naphthol-7-sul~onic acid in 150 parts f ~2~ 1~.3 parts of 36 Bé ~a3~ and 5 parts of ~a2C03. ~he whole mas5 wa~ ~ept under s-tirri~g for 2 hours at a pH of 9-9.5 and at a temperature of 15C. The dye~tuf~ was oomp~etel~ precipitated.
At the end of the coupling~ the whole was ~lltered under ~acuum and sgueezed dry. ~he product was dried at 95C.
~ he obtained product dyes cellulose fibers in bluei~h red shades with ~air fastne~s to moisture and light.
Modifications and ~ariations can9 of course, be made without departing from the ~pirit and scope of the invention.
. .
-- 4 ~
These dyestuffs dye cellulosic fibers in dark shades ranging ~rom violet to red.
Dyeing of fibers with the dyestuffs of the in~entlon is carried out using the same methods as are used with conventional direct dyestuffs, i.e., at a temperature ordinarily ranging from 50 to 100C from a water-bath containing adequate quantities e.gO from 0,01 g to 2-3g% about or according to the user~s exi-gence of dyestuffs and from 5 to 20% (with respect to the weight o~ the fiber) of anhydrous Na2SO~ or NaClO
~he following example~ are gi~en to illus-trate the invention~ all parts being understood as par-t~ by weight unless otherwise indicated.
~ 1 22.7 part~ of 4-4~-diamino-benzanilide suspended in 50 parts of water and 52 parts of 20 Bé hydroohloric acid were tetrazotized, after cooling with 150 parts of ice, by adding dropwise, at 0-5C over a period of 30 minutes~ a solution of 14 parts o~ NaN02 in 60 parts of H20- After 60 minutes stixring~
the exoess nitrous acid was remoYed using sulfamic acidO ~he resulting mass was neutrali~ed to weak Congo Red with 7 parts of calcium carbonateO The tetrazotization mass was poured over a few minutes onto a mass of 24 partæ of 2-amino-8-naphthol-6-sulfonic acid dissolved in 100 parts o~ water and 13,~ parts of 36 Bé NaOH and reprecipitated ~t a pH of 3.5 wi-th 28 parts of 20 Be ~Cl.
The coupling mass ~as kept at a pH of 305 for about 3o 4 hours with 30 parts of sodium acetate. 3 H20 at a temperature of 0-5C~ ~he pH was raised to 7.5 with 16 parts of ~a2C03 in the form of a 20~ solution (w/v).
16~3~3~363 The solu-tion was then added to 32 parts of H acid as previously defined dissolved in 1QO parts of water and 13.3 par-ts o~ 36 Bé NaOH brought to a pH of 8.5-9 with 10 parts of Ma2C03 and cooled to O-5C with 100 parts of ioeO
~he coupling mass was kept urlder stirring over night, while keeping the pH at 8.5-9 with smal]. additions of ~a2C~.
The following morning, the whole mass was heated to 60C for 4 hours and salted with 110 parts of roc~-salt.
The whole was filtered under Yacuum and completely squeezed dry.
The product was dried at 70~80C for 24 hours. ~his product dyes cellulose fibers in a violet shade with fair uni-~ormity and fa~tnessO
EXA~PIE 2 22.7 parts of 4~4~-diamino benzanilide were tetra-zotized as described in ~xample 1, after which the excess ni-trous acid V~9 removed with sulfamic acid.
~he tetrazotized mass was added, over a period of 40 minute~ to a solution o~ 22.8 parts of 2-amino-8-naphthol-6-~ulfonic acid dissolved in 125 parts of H20 and 13.3 parts of 36 Bé ~aOHO
~he whole mass was kept under sitrring over night at a pH of 1.8-2. It was then cooled to about 100a with 100 parts of ice and the solution was added~ in the form o~ a ~ine stream to 9.4 parts o~ phenol in 50 parts of water and 13.~ parts of 36 ~é ~aO~. ~he mass was kept under stirring for 2 hours at a pH of 9-9.5 and at a temperature of about 15Co At the end of the coupling~ the whole was acidified to light Congo red with 35 parts of 20 Bé HCl. ~he precipitated dyestuff was filtered under vacuum and completely dried off.
It was dried at 95C.
, ~ 1)3~3863 The obtained product dyes cellulose fibers in a yellowish red shade and fair fastness to moisture and light.
E ~
2207 parts of 4-4~-diamino-benzanilide were tetra zotized as described in Example 1 and the coupling with 2 amino-; 8-naphthol-6-sulfonio acid waæ carried out as described in ~xample 2. At the e~d of the couplingS the diazomonoazoic ma~s was added w~th 22.6 parts of 2-amino-5-naphthol-7-sul~onic acid in 150 parts f ~2~ 1~.3 parts of 36 Bé ~a3~ and 5 parts of ~a2C03. ~he whole mas5 wa~ ~ept under s-tirri~g for 2 hours at a pH of 9-9.5 and at a temperature of 15C. The dye~tuf~ was oomp~etel~ precipitated.
At the end of the coupling~ the whole was ~lltered under ~acuum and sgueezed dry. ~he product was dried at 95C.
~ he obtained product dyes cellulose fibers in bluei~h red shades with ~air fastne~s to moisture and light.
Modifications and ~ariations can9 of course, be made without departing from the ~pirit and scope of the invention.
. .
-- 4 ~
Claims
1. Sulfonated azo dyestuffs of the formula:
wherein A is , or .
wherein A is , or .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1996274A IT1009601B (en) | 1974-01-30 | 1974-01-30 | WATER-SOLUBLE DIAZOIC DYES DE RIVATI OF 4.4 DIAMINOBENZANILS DE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038863A true CA1038863A (en) | 1978-09-19 |
Family
ID=11162668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,885A Expired CA1038863A (en) | 1974-01-30 | 1975-01-29 | Water-soluble diazo dyestuffs derived from 4,4'-diamino-benzanilide |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS50108326A (en) |
| BE (1) | BE825019A (en) |
| CA (1) | CA1038863A (en) |
| CH (1) | CH606313A5 (en) |
| DE (1) | DE2503653A1 (en) |
| ES (1) | ES434213A1 (en) |
| FR (1) | FR2259139B1 (en) |
| GB (1) | GB1444339A (en) |
| IT (1) | IT1009601B (en) |
| NL (1) | NL7500860A (en) |
-
1974
- 1974-01-30 IT IT1996274A patent/IT1009601B/en active
-
1975
- 1975-01-24 NL NL7500860A patent/NL7500860A/en not_active Application Discontinuation
- 1975-01-27 GB GB343375A patent/GB1444339A/en not_active Expired
- 1975-01-27 CH CH95675A patent/CH606313A5/xx not_active IP Right Cessation
- 1975-01-28 FR FR7502503A patent/FR2259139B1/fr not_active Expired
- 1975-01-28 ES ES434213A patent/ES434213A1/en not_active Expired
- 1975-01-29 CA CA218,885A patent/CA1038863A/en not_active Expired
- 1975-01-29 DE DE19752503653 patent/DE2503653A1/en not_active Withdrawn
- 1975-01-30 BE BE152913A patent/BE825019A/en unknown
- 1975-01-30 JP JP1197175A patent/JPS50108326A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES434213A1 (en) | 1976-12-01 |
| CH606313A5 (en) | 1978-10-31 |
| JPS50108326A (en) | 1975-08-26 |
| GB1444339A (en) | 1976-07-28 |
| FR2259139A1 (en) | 1975-08-22 |
| DE2503653A1 (en) | 1975-07-31 |
| IT1009601B (en) | 1976-12-20 |
| FR2259139B1 (en) | 1977-04-15 |
| BE825019A (en) | 1975-07-30 |
| NL7500860A (en) | 1975-08-01 |
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