USRE18643E - Vat dyestttff and process of making same - Google Patents
Vat dyestttff and process of making same Download PDFInfo
- Publication number
- USRE18643E USRE18643E US18643DE USRE18643E US RE18643 E USRE18643 E US RE18643E US 18643D E US18643D E US 18643DE US RE18643 E USRE18643 E US RE18643E
- Authority
- US
- United States
- Prior art keywords
- vat
- ortho
- carboxylic acid
- dyestttff
- making same
- 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
- 238000000034 method Methods 0.000 title description 7
- 239000000047 product Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- HHXVJSCSDJBUGP-UHFFFAOYSA-N 4-chloro-1$l^{3},2-dithia-3,5-diazacyclopenta-3,5-diene Chemical class ClC1=NS[S]=N1 HHXVJSCSDJBUGP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000160765 Erebia ligea Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- JNIGYQOBELCEIZ-MAKDUZDQSA-L barium(2+);5-chloro-4-methyl-2-[(2Z)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O JNIGYQOBELCEIZ-MAKDUZDQSA-L 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Definitions
- vat dyestuffs are obtainable by condensing the dianhydride of 1.4.5.8-naphthalenetetra-carboxylic acid, or this acid itself or its substitution products, with an ortho-d1- amine or a salt of it.
- the new dyestufi' mixtures are distinguished by the beautiful shades they give, and their excellent properties as to fastness.
- vat-dyestuffs are obtainable by means of naphthalenetetra-carboxylic acid, because 1.4.5.8-napthalenetetra-carboxylic acid used as parent product is a perfectly White body to which, even if it is transformed into the di-imide, cannot be imparted the characteristic properties of a dyestuif.
- naphthalenetetra-carboxylic acid are heated in parts of nitrobenezene with 20 parts of ortho-phenylenediamine until the product resulting from the reaction is entirely sepa- 25 rated.
- This product is filtered off by suction and washed with alcohol until the excess of ortho-phenylenediamine is entirely eliminated.
- the new product forms, when dry, a bright red powder which dissolves in concentrated sulfuric acid to a yellowishbrown solution. It gives a green vat which dyes cotton the same color which, when the material is exposed to the air, changes to a brilliant red tint with a yellow hue.
- a product is obtainable as a. brown powder, which dissolves in concentrated sulfuric acid to a yellow solution with an intense green fluorescence.
- the vat prepared therefrom is of a green'color and dyes cotton the same color which, when the material is exposed to the air, changes to a grey to black tint.
- condensation products partially containing or not containing halogen may afterwards be halogenated.
- the halogenation may be effected by suspending the condensation prodnot in a diluent, such as nitrobenzene, and introducing for instance a gentle current of chlorine into the mass while heating to about l-180 0. Finally the mass is isolated in the usual manner.
- the chlorinated product thus obtained dissolves in concentrated sulfuric acid with a red color and dyes cotton from a green vat a reddish-brown tint.
- the condensation may also be efi'ected in absence of a solvent or diluent with the same result by melting together for a short time both components.
- vat dyestuffs consistlng 1n condensing a 1..5.8-napthalenetetracarboxylic 'acidwith an ortho-diamine V and halogenating the condensation product. ,5.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Reissuecl Nov. 1, 1932 UNITED STATES 'WILHELM ECKERT AND HEINRICH GRETTTNE, OF FRANKFORT-ON-THE-MAIN-HOCHST,
GERMANY, ASSIGNOR T GENERAL ANILINE DELAWARE WORKS, INC., A CORPORATION OF VAT DYES'I'UFF AND PROCESS OF MAKING SAME No Drawing. Original No, 1,588,451, dated June 15, 1926, Serial No. 44,369, filed July 17, 1925, and in Germany July 21, 1924. Application for reissue filed April 8, 1930. Serial No. 442,678.
We have found that new valuable mixtures of vat dyestuffs are obtainable by condensing the dianhydride of 1.4.5.8-naphthalenetetra-carboxylic acid, or this acid itself or its substitution products, with an ortho-d1- amine or a salt of it. The new dyestufi' mixtures are distinguished by the beautiful shades they give, and their excellent properties as to fastness.
It could not be expected that mixtures of vat-dyestuffs are obtainable by means of naphthalenetetra-carboxylic acid, because 1.4.5.8-napthalenetetra-carboxylic acid used as parent product is a perfectly White body to which, even if it is transformed into the di-imide, cannot be imparted the characteristic properties of a dyestuif.
The following example illustrates our invention, the parts being by weight:
10 parts of the dianhydride of 1.4.5.8-
naphthalenetetra-carboxylic acid are heated in parts of nitrobenezene with 20 parts of ortho-phenylenediamine until the product resulting from the reaction is entirely sepa- 25 rated. This product is filtered off by suction and washed with alcohol until the excess of ortho-phenylenediamine is entirely eliminated. The new product forms, when dry, a bright red powder which dissolves in concentrated sulfuric acid to a yellowishbrown solution. It gives a green vat which dyes cotton the same color which, when the material is exposed to the air, changes to a brilliant red tint with a yellow hue.
If for the ortho-phenylenediamine is substituted 4-chloro-1.Q-diaminobenzene and the further operations are carried out as above indicated, a product is obtainable which dyes cotton from a green vat a green tint which, when the material is exposed to the air,
changes to a bright reddish brown shade of excellent fastness.
From 4-nitro-1.Q-diaminobenzene and 1.4.- 5.8.-naphthalenetetra-carboxylic acid or its anhydride a product is obtainable as a. brown powder, which dissolves in concentrated sulfuric acid to a yellow solution with an intense green fluorescence. The vat prepared therefrom is of a green'color and dyes cotton the same color which, when the material is exposed to the air, changes to a grey to black tint.
In the same manner there may be condensed instead of the bases themselves their salts, particularly the hydrochlorides, with naphthalene-1.4.5.8-tetra-carboxylic acid or its anhydride.
Instead of condensing a naphthalene- 1.t.5.8-tetra-carboxylic acid halogenated or not, with a halogenated ortho-phenylenediamine substituted or not, the finally formed condensation products partially containing or not containing halogen, may afterwards be halogenated. The halogenation may be effected by suspending the condensation prodnot in a diluent, such as nitrobenzene, and introducing for instance a gentle current of chlorine into the mass while heating to about l-180 0. Finally the mass is isolated in the usual manner.
The chlorinated product thus obtained dissolves in concentrated sulfuric acid with a red color and dyes cotton from a green vat a reddish-brown tint.
As 1.4.5.8-naphthalenetetra-carboxylic acid reacts in essentially the same manner as the anhydride, we understand by the term 1.4.5.8 naphthalenetetra carboxylic' acid, used in the following claims, not only this acid itself but also its anhydride, and by an grtho-diamine we understand also the salts o it.
The condensation may also be efi'ected in absence of a solvent or diluent with the same result by melting together for a short time both components.
Our experiments have shown that the products obtainable by the above described process are not products of uniform chemical composition but represent in many cases mix- :ence of the substituent. p
tures of isomeric compounds formed by the reaction. When condensing for instance the dianhydride LL58 naphthalenetetra-carboxylic acid with ortho-phenylenediamine a product is obtained which represents a mixture of the two isomeric dyestuffs of the following formulae:
\Vhen using instead of ortho-phenylenediamine a substitution product thereof in most cases likewise a mixture of two isomeric compounds is obtained, althoughgenerally when using a substituted ortho-diphenylene compound the formation of the one or of the other of the two isomeric compounds preponderates according to the directing infiu- We claim: V
1. The process which comprises condensing a 1.4.5.8-naptha1enetetra-carboxylic acid with an ortho-diamine.
2. The process which comprises condensing a 1.4.5.8napthalenetetra-carboxylic acid with an ortho-diaminein presence of a dil- I uent.
,3. Process of preparing Vat dyestuffs, con sisting in condensing 1.4.5.8-naphthalenetetracarboxylic acid with a nitrated 1.2-diaminobenzene. V V
4. Process of preparing vat dyestuffs, consistlng 1n condensing a 1..5.8-napthalenetetracarboxylic 'acidwith an ortho-diamine V and halogenating the condensation product. ,5. The products which are obtainable by condensing a 1.45.8-napthalenetetra-carboxylic acid with an ortho-diamine the said products representmg a mixture of the two isomerlc dyestuffs of the following compositionsz -wherein X represents hydrogen or any substituent and R stands for hydrocarbon sub-' stituted or not.
6. The products which are obtainable by condensing a 1.4.5.8-napthalenetetracarboxylic acid with an ortho-diam'inojcompound of the benzene series the said products representing a mixture of the two isomeric dyestufis of the following formulae:
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE18643E true USRE18643E (en) | 1932-11-01 |
Family
ID=2082126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US18643D Expired USRE18643E (en) | Vat dyestttff and process of making same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE18643E (en) |
-
0
- US US18643D patent/USRE18643E/en not_active Expired
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