US2666757A - Azo dyes for cellulosic fibers - Google Patents
Azo dyes for cellulosic fibers Download PDFInfo
- Publication number
- US2666757A US2666757A US170950A US17095050A US2666757A US 2666757 A US2666757 A US 2666757A US 170950 A US170950 A US 170950A US 17095050 A US17095050 A US 17095050A US 2666757 A US2666757 A US 2666757A
- Authority
- US
- United States
- Prior art keywords
- cellulosic fibers
- dyes
- naphthylamine
- anisidine
- azo dyes
- 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
- 239000000835 fiber Substances 0.000 title description 8
- 239000000987 azo dye Substances 0.000 title description 3
- 239000000975 dye Substances 0.000 description 20
- 239000002253 acid Substances 0.000 description 14
- 229920000297 Rayon Polymers 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 229920013685 Estron Polymers 0.000 description 5
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 229960003399 estrone Drugs 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 4
- 239000002964 rayon Substances 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 238000004855 creaseproofing Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-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
- 238000002360 preparation method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Definitions
- the present invention relates to azo dyes for cellulosic fibers obtained by diazotizing a Z-naphthylamine disulfonic acid, coupling the same with S-methyl-O-anisidine, and phosgenating the resulting azo dyestuff.
- the dyes yield tan or mustard shades instead of shades of orange.
- the urea derivatives from l-naphthylamine disulfonic acids and o-anisidine are obtained in no appreciable yields. If the o-anisidine be replaced by -methyl-o-anisidine, either inappre- For instance, fabricsmade from fibers I 4 Claims. (01. 260-175) ciable yields of the dyeare obtained or the dyes produce tan or mustard shades in lieu of a pleasant orange shade.
- I v The urea derivatives from 2-naphthylaminedisulfoni'c' acids and 'o-anisidine give low yields as well as undesired shades.
- urea anisidine dye cotton andregenen ated cellulose bright orange-yellow to orange. shades distinguished by good dischargeability.
- RN N NH 1. l; OH... I in which R. is 4,8-disulfonaphthy fonaphthylene or 5,7-disulfonaphthylene, the naphthylene radical being linked to the azo bridge in the 2-position. 7
- R. is 4,8-disulfonaphthy fonaphthylene or 5,7-disulfonaphthylene, the naphthylene radical being linked to the azo bridge in the 2-position. 7
- These products are prepared by diazotizing the desired 2-naphthylamine disulfonic acid and coupling it in acid solution with a molecular proportion of fi-methyl-o-anisidine.
- the resulting monazo dye is transformed into the urea by reacting it with phosgene at a temperature ranging from about 20 to C. in a solution with a pH from slightly acid to slightly alkaline.
- Example I 22 grams of 2-naphthylamine-4,8-disulfonic acid are dissolved at room temperature in 250' ml. of water to neutral reaction with about 25 m1. of sodium hydroxide solution (40% weight by volume). To this solution. are added 10.5
- derivf atives of azo dyestuffs possessing all of the above prerequisites may be obtain'ed 'by phosgenating the ewe dyestuffs resulting from the diaZotiZa-J. tion of 2 naphthy1amine-4,8-disulfonic acid,-F2-" eiie. a isiii ml. of hydrochloric acid (23 B.). This solution is run while stirring into a mixture of 250 m1. of water, ice, 5 grams of sodium nitrite and 5 m1. of hydrochloric acid (23 B.). 10.4 grams of 5- methyl-o-anisidine are dissolved in a solution of 60 ml.
- Phosgene is run into the reaction mixture at a temperature between 20 and zfififlnrwhile maintaining the pH of the mixture between 'I -and 8 by adding about 200 ml. of sodium hydroxide solution (40% weight by volume). The product .is salted out and isolated by filtration. The weight of the dry dye is 45 grams. The dye dves cotton and viscose rayon a bright orangefthe dyeings being very fast to light and having the ability to leave :estron effects completely unstained.
- Example II action "to estronefiects are similar to :the dye of Example I.
- ExampleIII The procedure'is the same as in Example I excepting that the 2-naphthylamine- 4g8-disulioni'c acid is replaced by an identical amount of '2- naphthylamine-6,8-disulfonic acid. After isolation-and drying, the yield is 37.9 grams. The material dyes cotton and viscose rayon somewhat redder-than the .dye of Example I.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA528484A CA528484A (en) | 1950-06-28 | Azo dyes for cellulosic fibers | |
| IT491804D IT491804A (enrdf_load_stackoverflow) | 1950-06-28 | ||
| US170950A US2666757A (en) | 1950-06-28 | 1950-06-28 | Azo dyes for cellulosic fibers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US170950A US2666757A (en) | 1950-06-28 | 1950-06-28 | Azo dyes for cellulosic fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2666757A true US2666757A (en) | 1954-01-19 |
Family
ID=22621942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US170950A Expired - Lifetime US2666757A (en) | 1950-06-28 | 1950-06-28 | Azo dyes for cellulosic fibers |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2666757A (enrdf_load_stackoverflow) |
| CA (1) | CA528484A (enrdf_load_stackoverflow) |
| IT (1) | IT491804A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2936305A (en) * | 1956-11-29 | 1960-05-10 | Sandoz Ag | Water-insoluble disazo dyestuffs |
| US3621008A (en) * | 1968-10-03 | 1971-11-16 | Du Pont | Direct disazo and tetraazo urea dyes and method of preparation |
| US3643269A (en) * | 1967-10-25 | 1972-02-22 | Sandor Ltd | Dyeing synthetic polyamide fibers with disulfonated diaryl bis axo carbonilides |
| FR2124463A2 (enrdf_load_stackoverflow) * | 1971-02-05 | 1972-09-22 | Sandoz Sa |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US935018A (en) * | 1909-05-04 | 1909-09-28 | Farbenfab Vorm Bayer F & Co | Azo dye. |
| CH49515A (de) * | 1909-05-07 | 1911-03-01 | Farbenfab Vorm Bayer F & Co | Verfahren zur Darstellung eines orangen Baumwollfarbstoffes |
| GB191021202A (en) * | 1910-09-12 | 1911-07-20 | Philip Arthur Newton | Manufacture and Production of New Azodyestuffs. |
| US999944A (en) * | 1911-04-25 | 1911-08-08 | Farbenfab Vorm Bayer F & Co | Yellow disazo dye. |
| US1538934A (en) * | 1924-04-28 | 1925-05-26 | Nat Aniline & Chem Co Inc | Disazo dyes containing a diphenylurea nucleus |
-
0
- IT IT491804D patent/IT491804A/it unknown
- CA CA528484A patent/CA528484A/en not_active Expired
-
1950
- 1950-06-28 US US170950A patent/US2666757A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US935018A (en) * | 1909-05-04 | 1909-09-28 | Farbenfab Vorm Bayer F & Co | Azo dye. |
| CH49515A (de) * | 1909-05-07 | 1911-03-01 | Farbenfab Vorm Bayer F & Co | Verfahren zur Darstellung eines orangen Baumwollfarbstoffes |
| GB191021202A (en) * | 1910-09-12 | 1911-07-20 | Philip Arthur Newton | Manufacture and Production of New Azodyestuffs. |
| US999944A (en) * | 1911-04-25 | 1911-08-08 | Farbenfab Vorm Bayer F & Co | Yellow disazo dye. |
| US1538934A (en) * | 1924-04-28 | 1925-05-26 | Nat Aniline & Chem Co Inc | Disazo dyes containing a diphenylurea nucleus |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2936305A (en) * | 1956-11-29 | 1960-05-10 | Sandoz Ag | Water-insoluble disazo dyestuffs |
| US3643269A (en) * | 1967-10-25 | 1972-02-22 | Sandor Ltd | Dyeing synthetic polyamide fibers with disulfonated diaryl bis axo carbonilides |
| US3621008A (en) * | 1968-10-03 | 1971-11-16 | Du Pont | Direct disazo and tetraazo urea dyes and method of preparation |
| FR2124463A2 (enrdf_load_stackoverflow) * | 1971-02-05 | 1972-09-22 | Sandoz Sa |
Also Published As
| Publication number | Publication date |
|---|---|
| CA528484A (en) | 1956-07-31 |
| IT491804A (enrdf_load_stackoverflow) |
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