US1034173A - Red-violet triphenylmethane dye. - Google Patents
Red-violet triphenylmethane dye. Download PDFInfo
- Publication number
- US1034173A US1034173A US64819211A US1911648192A US1034173A US 1034173 A US1034173 A US 1034173A US 64819211 A US64819211 A US 64819211A US 1911648192 A US1911648192 A US 1911648192A US 1034173 A US1034173 A US 1034173A
- Authority
- US
- United States
- Prior art keywords
- violet
- red
- acid
- triphenylmethane dye
- methylene
- 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
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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/22—Amino derivatives of triarylmethanes containing OH groups bound to an aryl nucleus and their ethers and esters
Definitions
- rnmnnfmmnuwoo or ELBEBFELD
- GERMANY A oon'rone'rlon or GERMANY.
- the present-invention relates to the manufacture and production of new and aluable triphenylniethane'dyestuffs capable of being chromed after-dyeing having the following gene'r'al formulae I T-COOH '(XZH or CH3,-.Y:CH3 or halogen, 2:11
- the new dyes are after being dried and pulverized red powders soluble in dilute caustic soda lye with vfrom a redviolet to bluish-red coloration; dyeing wool after chroming red-Violet to blue-violet shades.
- the process fortheir production consists in condensing in the presence.
- oxidizing agents methylene-di-salicylic acid or its derivatives with such derivatives of the salicylic ac d wh ch possess a free para contain one or two indifferent substituents in meta position to the hydroxy group.
- page M8 canalso be oxidized at first tothe formaur1ndl-carboxylic acids, these compounds condensed with the above mentioned components and the leuco acids their OXl-, dized to the dyestuffs.
- the dyestuffs can also be dyed on Wool mordanted with chromium compounds or can be dyed according" to the one-loath method directly with chrome mordants.
- Methylene-di-ortho-cresotinic acid may be replaced by methylene-di-salicylic acid or by its symmetrical and unsymmetrical derivatives.
- the symmetrical xylenol-ortho-carboxylic acid also meta-' cresotinic acid, meta-chloro-salicylic acid meta-chloro-ortho-cresot1n1c' acid etc, can he used.
- Methylene-dtoi'tho-eres0ti1 lie acid meta-chloi'o-ottlioeresotinic acid ..l Dilheulty MHUlQl-l'ktl bluish-red. Violet.
- X and Z include hydrogen and l 3 methyl group and Y ,ai substituent in meta position to the ()Ilgroup, which are soluble in dilute caustic soda lye with from ⁇ Vitnesses L. NUFER,
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
- position to the hydroxygroup and which [1131"WEILER5.QFVELBEBFELDLGERMANY, ASSIGNQB, T0 FARBENFABRIKEN vomu.
rnmnnfmmnuwoo, or ELBEBFELD, GERMANY, A oon'rone'rlon or GERMANY.
nun-Vienna. rarruuurmvmrnaun DYE.
1.03 m. f llo'm'awlng.
To dl l z'o'hom it may concern! Be 'itknownthat I, MAX Wanna, doctor of pliilbs'ophy, chemist, citizen of the Ger man Empire, residing at Elberfelrh- German have inventednewand useful Improvementsin Red vifoletTriphenylmethane Dye, of which thefollowingis a specification. I
The present-invention relates to the manufacture and production of new and aluable triphenylniethane'dyestuffs capable of being chromed after-dyeing having the following gene'r'al formulae I T-COOH '(XZH or CH3,-.Y:CH3 or halogen, 2:11
or CH "The new dyes are after being dried and pulverized red powders soluble in dilute caustic soda lye with vfrom a redviolet to bluish-red coloration; dyeing wool after chroming red-Violet to blue-violet shades. The process fortheir production consists in condensing in the presence. of
oxidizing agents methylene-di-salicylic acid or its derivatives with such derivatives of the salicylic ac d wh ch possess a free para contain one or two indifferent substituents in meta position to the hydroxy group.
' In order to illustrate the new process more fully the following example is given, the parts being by Weight:--23.7 parts of methylene-diortho-cresotinic acid and 13.7
Specification of, Letters Patent.
Patented July 30, 1912.
- Application filed. September 7, 1911. Serial no. 648,192.
' parts of symmetrical- Xylenol-ortho-carboxylic acid- (OIrDCH :CH :GOOH=1:3:5:2)
are stirred with 320 parts of strong sulfuric acid and the necessary quantity of nitrite at 20-40 C; until the evolution of nitrogen oxid ceases and the quantity of the dyestutl' produced no longer increases, The product of the reaction is poured on ice and the dyestuff is filtered off. It is a red orange powder soluble in hot Water with a scarlet-red coloration and in caustic soda lye with a f red-violet coloration. It has the formula:
The shades 011 wool, when after-treated with chrome mordants are blue-violet. Other oxidizing agents can also be used. The methanes obtained according to the Bem'chte derDeuzlschen chemz'schen Gesellschaft 31,
page M8 canalso be oxidized at first tothe formaur1ndl-carboxylic acids, these compounds condensed with the above mentioned components and the leuco acids their OXl-, dized to the dyestuffs. The dyestuffs can also be dyed on Wool mordanted with chromium compounds or can be dyed according" to the one-loath method directly with chrome mordants. v
Methylene-di-ortho-cresotinic acid may be replaced by methylene-di-salicylic acid or by its symmetrical and unsymmetrical derivatives. Instead of the symmetrical xylenol-ortho-carboxylic acid also meta-' cresotinic acid, meta-chloro-salicylic acid meta-chloro-ortho-cresot1n1c' acid etc, can he used.
Metfhglene-dborthocresotinie acid symmetrical xy]enel-ortho-i-nrlioxylic i Rather dlllienliy senrlet.... l i
In the following table the properties of some of the new dyes are given l SOlHUOH in Dyes wool caustic sodn lye.
chrome 'lreu led with Red-violet.
Rod-violet.
Methylene-orthomumcresotinic acid tsymnietrienl xylonol-orthoenrboxy lie acid. 1
Blne-vlolut.
Red'violet. Blue-violet. ne 1 lvietliylene-di-ortho-creso tinieacid metn-eresotiniencid Ratherdinleullyredomnge BlUiSlI-IUl. liedylolet.
Methylene di-ortlimeresotinic acid meta-chloin-salicylic acid Diil'n-uhy senrleru-d Blnish-ied. Violet.
Methylene-dtoi'tho-eres0ti1lie acid meta-chloi'o-ottlioeresotinic acid ..l Dilheulty MHUlQl-l'ktl bluish-red. Violet.
I claim a recl-violet to bluish-red coloration; dyeing 1. The herein described new triphenylmethane dyestuffs having the following general formulziz Y tiolly ns'deseribed.
\\'ool. :il'tur chi-owing red-violet l0 hlnevioleb shades, suhslanlially as described.
The herein described new triphenylmethane dye having the formula:
which is soluble in dilute caustic soda lye \Vllll tl lJlHB-VlOlOtcoloration; dyeing wool hatter ehronnn blue-violet shades, substan- In'; testimony whereof I have hereunto set iny'huncl in the presence of two subscribing witnesses. I
in which X and Z include hydrogen and l 3 methyl group and Y ,ai substituent in meta position to the ()Ilgroup, which are soluble in dilute caustic soda lye with from \Vitnesses L. NUFER,
ALBERT F. \Ui-"nn.
MAX WEILER. 1 8.]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64819211A US1034173A (en) | 1911-09-07 | 1911-09-07 | Red-violet triphenylmethane dye. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64819211A US1034173A (en) | 1911-09-07 | 1911-09-07 | Red-violet triphenylmethane dye. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1034173A true US1034173A (en) | 1912-07-30 |
Family
ID=3102455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US64819211A Expired - Lifetime US1034173A (en) | 1911-09-07 | 1911-09-07 | Red-violet triphenylmethane dye. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1034173A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2971013A (en) * | 1957-03-13 | 1961-02-07 | Diamond Alkali Co | Polychlorobenzhydryl cresol |
| US4152341A (en) * | 1975-12-29 | 1979-05-01 | Imperial Chemical Industries Limited | Triaryl or diarylpyridyl methanes |
| USRE31467E (en) * | 1975-12-29 | 1983-12-20 | Imperial Chemical Industries Plc | Triaryl or diarylpyridyl methanes |
| US11115711B2 (en) | 2012-08-17 | 2021-09-07 | Flextronics Ap, Llc | Thumbnail cache |
-
1911
- 1911-09-07 US US64819211A patent/US1034173A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2971013A (en) * | 1957-03-13 | 1961-02-07 | Diamond Alkali Co | Polychlorobenzhydryl cresol |
| US4152341A (en) * | 1975-12-29 | 1979-05-01 | Imperial Chemical Industries Limited | Triaryl or diarylpyridyl methanes |
| USRE31467E (en) * | 1975-12-29 | 1983-12-20 | Imperial Chemical Industries Plc | Triaryl or diarylpyridyl methanes |
| US11115711B2 (en) | 2012-08-17 | 2021-09-07 | Flextronics Ap, Llc | Thumbnail cache |
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