US1590042A - Trisazo dyestuffs and process of making same - Google Patents
Trisazo dyestuffs and process of making same Download PDFInfo
- Publication number
- US1590042A US1590042A US45695A US4569525A US1590042A US 1590042 A US1590042 A US 1590042A US 45695 A US45695 A US 45695A US 4569525 A US4569525 A US 4569525A US 1590042 A US1590042 A US 1590042A
- Authority
- US
- United States
- Prior art keywords
- parts
- making same
- trisazo
- dyestuffs
- naphthylenediamin
- 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
- 238000000034 method Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004043 dyeing Methods 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CXENHBSYCFFKJS-OXYODPPFSA-N (Z,E)-alpha-farnesene Chemical compound CC(C)=CCC\C(C)=C\C\C=C(\C)C=C CXENHBSYCFFKJS-OXYODPPFSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011734 sodium Substances 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
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
Definitions
- the new dyestuffs are, when dry, bluish black bodies, soluble in water to a deep dark solution, yielding upon reduction with stannous chloride an arylamin, the l-hydroxy-2. 7.8-triaminonaphthalene-3.6.-disulfonic acid, a para diamin base and a triaminonaphthalene, dyeing cotton and wool in bluish black shades and therefore especially adapted for dyeing mixed fabrics of cotton and wool.
- the dyestuffs where the diamin base used belongs to the diphenyl series and the naphthylenediamin used is 1.5-naphthylenediamin, are especially valuable.
- the new dyestulfs may be obtained by combining at first one molecular proportion of the tetrazo compound of a para-diamin base in mineral acid solution with the 1.8 aminonaphthol-3.6-disulfonie acid and then combining the intermediate body, thus formed, in the usual manner with a monodiazo compound and a heteronuclear alph anaphthylenediamin, this term including 1.5- and 1.8-naphthylenediamin.
- the intermediate body may be at first combined with the na hthylenediamin and then with the monodiazo compound.
- the new products are distinguished by the diiferenoe of shades and by dyeing half-woollen goods in shades of fuller overshine, retaining the beautiful bluish tone and not changin like those to a reddish black under artificial light.
- diamin base and atriaminonaphthalene dye ing cotton and --wool in bluish black shades and therefore especially adapted for dyeing mixed :fabrics of cotton and wool.
- a process of making trisazo dyestulfs' consistingin combining at first one molecular proportion of a tetrazo compound in mineral acid solution -w1th the 1.8-aminonaphthol-3.6-disulfonic acid and then combining the intermediate product, thus formed, with a monodiazo compound and a .heteronuclear alpha naphthylenediamin.
- a process of making a trisazo dyestufl? consisting in combining at first one molecular proportion of tetrazotized benzidin in mineral acid solution with the 1.8-aminonaphthol-3.6-disulfonic acid and then combining the intermediate roduct,thus formed,
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented June 22, 1926.
UNITED- STATES PATENT OFFICE.
AUGUS'I LEOPOLD LASKA AND FRITZ WEBER, 0F OFFENBACH-ON-Tfllfd-MAIN, GER- MANY, ASSIGNORS TO CORPORATION OF CHEMISCHE FABRIK GRIESHEIIMI-ELEK TRON, OF FRANKFORT-ON-THE-MAIN, GERMANY. v
TRISAZO DYESTUFFS AND PROCESS OF MAKINGL'SAME.
Ho Drawing. Application filed July 23, 1925, Serial No. 45,695, and in Germany November 15, 1924.
BOgN
The new dyestuffs are, when dry, bluish black bodies, soluble in water to a deep dark solution, yielding upon reduction with stannous chloride an arylamin, the l-hydroxy-2. 7.8-triaminonaphthalene-3.6.-disulfonic acid, a para diamin base and a triaminonaphthalene, dyeing cotton and wool in bluish black shades and therefore especially adapted for dyeing mixed fabrics of cotton and wool.
The dyestuffs, where the diamin base used belongs to the diphenyl series and the naphthylenediamin used is 1.5-naphthylenediamin, are especially valuable.
The new dyestulfs may be obtained by combining at first one molecular proportion of the tetrazo compound of a para-diamin base in mineral acid solution with the 1.8 aminonaphthol-3.6-disulfonie acid and then combining the intermediate body, thus formed, in the usual manner with a monodiazo compound and a heteronuclear alph anaphthylenediamin, this term including 1.5- and 1.8-naphthylenediamin. As an alternative, the intermediate body may be at first combined with the na hthylenediamin and then with the monodiazo compound.
Compared with the analogous dyestufis described in the U. S. Letters Patent No. 688,478, dated December 10, 1901, containing meta-diamins of the benzene series as' the final component, the new products are distinguished by the diiferenoe of shades and by dyeing half-woollen goods in shades of fuller overshine, retaining the beautiful bluish tone and not changin like those to a reddish black under artificial light.
temperatures in Centigrade degrees.
Example.
18.4: parts of benzidin are diazotized in the usual manner with 57 parts of hydrochloric acid of 20 B. and 13.8 parts of sodium nitrite. While stirring and cooling, a neutral solution of 34.1 parts of 1.8.3.6 amino-naphtholdisulfonic acid (monosodium-salt) is slowly poured in. When the combination is complete, the intermediate body or product, thus obtained, is combined with a solution of diazo-benzene, prepared from 9.3 parts of anilin, 150 parts of water, 28.5 parts of hydrochloric acid of 20 B. 6.9 parts of sodium nitrite and ice, and made alkaline with carbonate of soda. hen no more unchanged diazobenzene can be detected, a solution of 16.55 parts of 1.5- naphthylenediamin in 700 parts of water and 24 parts of hydrochloric acid of 20 N B. are poured in. After stirring for about five hours at 10-15 O. the combination is complete. The dyestufi', corresponding probably to the formula: j
naphthylenediamin. All these d estuffs yield upon half-woollen goods bluis black shades of a full overshine.
'Now what we claim and desire to secure by Letters Patent .is the following:
1. As "new compounds trisazo dyestuffs having probably the general formula:
which are, when dry, bluish black bodies, soluble in water to a deep dark solution,
yielding upon reduction withstannous chloride an arylamin, the 1-hydroxy-2.7.8-tri- 'aminonaphthalene-ii.G-disulfonic acid, a para,
diamin base and atriaminonaphthalene, dye ing cotton and --wool in bluish black shades and therefore especially adapted for dyeing mixed :fabrics of cotton and wool.
.2. A process of making trisazo dyestulfs' consistingin combining at first one molecular proportion of a tetrazo compound in mineral acid solution -w1th the 1.8-aminonaphthol-3.6-disulfonic acid and then combining the intermediate product, thus formed, with a monodiazo compound and a .heteronuclear alpha naphthylenediamin.
3. As new compounds trisazo dyestuffs having probably the general formula:
which are, when dry, bluish black bodies, soluble in water to a deep dark solution, yielding upon reduction with stannous chlonix, on- Nu}: LII-NU S0;Na OiNa Nn-N which is,when dry,a bluish black body soluble in water toa deep dark solution, yielding upon reduction with stannous chloride, anilin, the l-hydroxy-2.7.8-triaminonaphthalene-3.6-disultonic acid, benzidin and a triaminonaphtlialene dyeing cotton and wool in bluish black sha es and therefore especially adapted for dyeing mixed fabrics of cotton and wool.
6. A process of making a trisazo dyestufl? consisting in combining at first one molecular proportion of tetrazotized benzidin in mineral acid solution with the 1.8-aminonaphthol-3.6-disulfonic acid and then combining the intermediate roduct,thus formed,
with diazobenzene an 1.5-naphthylenediamin.
In testimony, that we claim the foregoing as our invention we have signed our names, this 7th day of u1y1925.
AUGUST LEOPOLD LASKA. FRITZ WEBER.
rec
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1590042X | 1924-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1590042A true US1590042A (en) | 1926-06-22 |
Family
ID=7736617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US45695A Expired - Lifetime US1590042A (en) | 1924-11-15 | 1925-07-23 | Trisazo dyestuffs and process of making same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1590042A (en) |
-
1925
- 1925-07-23 US US45695A patent/US1590042A/en not_active Expired - Lifetime
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