USRE18758E - Dyesttjff derived from indoline bases and process of preparing same - Google Patents
Dyesttjff derived from indoline bases and process of preparing same Download PDFInfo
- Publication number
- USRE18758E USRE18758E US18758DE USRE18758E US RE18758 E USRE18758 E US RE18758E US 18758D E US18758D E US 18758DE US RE18758 E USRE18758 E US RE18758E
- Authority
- US
- United States
- Prior art keywords
- indoline
- yellow
- bases
- derived
- dyesttjff
- 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 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 7
- 229920002955 Art silk Polymers 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 235000018553 tannin Nutrition 0.000 description 6
- 229920001864 tannin Polymers 0.000 description 6
- 239000001648 tannin Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Definitions
- the present invention relates to new dyestufl's derived from indoline bases and a process of preparing same.
- benzene nucleus may be substituted or not or a salt thereof of the formula:
- I alkyl wherein the benzene nucleus may be substituted or not and 00 stands for an organic or inorganic acid ra-dicle with an ester or a salt of nitrous acid in the presence of an organic acid anhydride, as for example acetic anhydride which serves as a condensing agent, there are produced new yellow to orange-red dyestuffs, which correspond probably to the general formula:
- benzene nuclei may be substituted or not and :0 stands for an organic or inorganic acid radicle.
- the new dyestuffs are yellow to orange-red crystalline powders soluble in water with light yellow to orange-red color. They dye natural and artificial silk and cotton when Serial No. 594,383.
- tannin or other mordants in beautiful greenish yellow to reddish-orange shades of good fastness to light.
- Example 1 Onepart of 1.3.3-trimethyl- Q-methylene indoline (see Berichte der Deutschen Chem. Gese-llschaft, volume 23, page 2630, volume 31, page 612 and page 614) is dissolved in at least 1 part of acetic acid anhydride and 2 parts of sodium nitrite are gradually added with stirring. The solution soon becomes intensely yellow colored, which process may be accelerated by heating. When the indoline has disappeared, the re action mass is run into water in order to destroy the acetic acid anhydride, and the dyestuff is salted out with sodium chloride and zinc chloride, if necessary, with the addition of sodium bisulfite, in order to destroy theexcess of sodium nitrite.
- the new dyestuff has probably the formula:
- Example 2.1 part of 5-amido-1.3.3-trimethyl-Q-methylene indoline are mixed with 1 part of powdered dry sodium nitrite and the mixture is slowly brought into 2 parts of acetic acid anhydride while stirring. Stirring is continued until the indoline has disappeared, then the reaction mass is run into water and the dyestufl, which dissolves in 90 water with yellow-red color is salted out. It
- a stands for an organic or inorganic acid radicle and wherein the benzene nuclei may be substituted,said products being in the dry state yellow to orange-red crystalline powders, soluble in water withlight yellow to orange-red color, and which dye natural and artificial silk and cotton,'when using tannin or other mordants beautiful greenishyellow to reddish-yellow shades of good fastness to light.
- m stands for an organic or inorganic acid radicle, which is in a dry state an orangered crystalline powder, easily soluble in water and diluted acids, and which dyes natural and artificial silk and cotton when using tannin as a mordant in reddish-yellow shades of 'quite good fastness to light.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Reissued Mar. 7, 1933 UNITED STATES PATENT OFFICE OTTMAR WAHL, OF LEVERKUSEN, GERMANY; ASSIGNOR TO GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE DYESTUFF DERIVED FROM INDOLINE BASES AND PROCESS OF PREPARING SAME N0 Drawing. Original N0. 1,755,678, dated April 22, 1930, Serial No. 186,829, filed April 26, 1927.
Application for reissue filed February 20, 1932.
The present invention relates to new dyestufl's derived from indoline bases and a process of preparing same.
I have found that by treating a 1.3.3-tr alkyl-Q-methylene indoline (such as 1.3.3-tr1- methyLQ-methylene indoline) of the formula:
alkyl all:
wherein the benzene nucleus may be substituted or not or a salt thereof of the formula:
alkyl i a1kyl N/ CH| I alkyl wherein the benzene nucleus may be substituted or not and 00 stands for an organic or inorganic acid ra-dicle with an ester or a salt of nitrous acid in the presence of an organic acid anhydride, as for example acetic anhydride which serves as a condensing agent, there are produced new yellow to orange-red dyestuffs, which correspond probably to the general formula:
wherein the benzene nuclei may be substituted or not and :0 stands for an organic or inorganic acid radicle.
The new dyestuffs are yellow to orange-red crystalline powders soluble in water with light yellow to orange-red color. They dye natural and artificial silk and cotton when Serial No. 594,383.
using tannin or other mordants, in beautiful greenish yellow to reddish-orange shades of good fastness to light.
The following examples will illustrate my invention, all parts being by weight:
Example 1.-Onepart of 1.3.3-trimethyl- Q-methylene indoline (see Berichte der Deutschen Chem. Gese-llschaft, volume 23, page 2630, volume 31, page 612 and page 614) is dissolved in at least 1 part of acetic acid anhydride and 2 parts of sodium nitrite are gradually added with stirring. The solution soon becomes intensely yellow colored, which process may be accelerated by heating. When the indoline has disappeared, the re action mass is run into water in order to destroy the acetic acid anhydride, and the dyestuff is salted out with sodium chloride and zinc chloride, if necessary, with the addition of sodium bisulfite, in order to destroy theexcess of sodium nitrite. The new dyestuff has probably the formula:
It is a clear, greenish-yellow body, which dyes natural and artificial silk and cotton when using tannin or other mordants, in beautiful greenish-yellow shades of good fastness to light, to acids and to alkalies. Instead of sodium nitrite for example, amyl nitrite can be employed; the reaction can also be carried out in the presence of a solvent.
Example 2.1 part of 5-amido-1.3.3-trimethyl-Q-methylene indoline are mixed with 1 part of powdered dry sodium nitrite and the mixture is slowly brought into 2 parts of acetic acid anhydride while stirring. Stirring is continued until the indoline has disappeared, then the reaction mass is run into water and the dyestufl, which dissolves in 90 water with yellow-red color is salted out. It
yellow to reddish-yellow shades of good fast-- wherein m stands for an organic or inorganic acid radical.
' It is in a dry state an orange-red crystalline powder, easily soluble in water and diluted acids. It dyes natural and artificial silk and cotton when using tannin asmordant in reddish-yellow shades of quite good fastnessto light. a 4
I wish it to be understood that inthe following claims one may use instead of a salt of the nitrous acid also an ester of the nitrous acid, and instead of a 1.3.3-trialkyl-2-methylene indoline a salt thereof.
I claim: 4
1. The process which consists in reacting with a salt of nitrous acid upon a 13.3-
trialkyl-Q-methylene indoline of the general formula:
alkyl (Jalkyl N :CH:
a lkyl wherein the benzene nucleus may be substituted in the presence of acetic acid anhydrlde. 2. The process which consists in reacting with sodium nitrite upon 5-amino- 1.3.3-trimethyl-Q-methylene indoline of the probable formula:
N :CHI
in the presence of acetic acid anhydride.
3. As new products dyestufl's corresponding probably to the general formula:
alkyl wherein the benzene nuclei may be substituted or not and 0: stands for an organic or inorganic acid radicle,which are in a dry state yellow to orange-red crystalline powders, soluble in water with light yellow to V orange-red color, and which dye natural and artificial silk and cotton when using tannin or other morda'nts' in beautiful greenish- As newff pi'oducts the dyestuffs corresponding probably to the general formula:
wherein a stands for an organic or inorganic acid radicle and wherein the benzene nuclei may be substituted,said products being in the dry state yellow to orange-red crystalline powders, soluble in water withlight yellow to orange-red color, and which dye natural and artificial silk and cotton,'when using tannin or other mordants beautiful greenishyellow to reddish-yellow shades of good fastness to light.
5. As a new product a dyestufi corresponding probably to the general formula:
:H, mo LIIH CUHx 11,o t NH oH, oo a L to orn z I OH: CH:
wherein m stands for an organic or inorganic acid radicle, which is in a dry state an orangered crystalline powder, easily soluble in water and diluted acids, and which dyes natural and artificial silk and cotton when using tannin as a mordant in reddish-yellow shades of 'quite good fastness to light.
In testimony whereof I aflix my signature.
OTTMAR WAHL,
Publications (1)
Publication Number | Publication Date |
---|---|
USRE18758E true USRE18758E (en) | 1933-03-07 |
Family
ID=2082323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US18758D Expired USRE18758E (en) | Dyesttjff derived from indoline bases and process of preparing same |
Country Status (1)
Country | Link |
---|---|
US (1) | USRE18758E (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2556516A (en) * | 1948-01-02 | 1951-06-12 | Eastman Kodak Co | 2-acylated arylamino-2-thioethylidene derivatives of heterocyclic nitrogen bases |
-
0
- US US18758D patent/USRE18758E/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2556516A (en) * | 1948-01-02 | 1951-06-12 | Eastman Kodak Co | 2-acylated arylamino-2-thioethylidene derivatives of heterocyclic nitrogen bases |
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